#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:21:57 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229075 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229946.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_7229946 loop_ _publ_author_name 'Nisar, Madiha' 'Sung, Herman H.-Y.' 'Puschmann, Horst' 'Lakerveld, Richard' 'Haynes, Richard K.' 'Williams, Ian D.' _publ_section_title ; 11-Azaartemisinin cocrystals with preserved lactam : acid heterosynthons ; _journal_issue 9 _journal_name_full CrystEngComm _journal_page_first 1205 _journal_paper_doi 10.1039/C7CE01875D _journal_volume 20 _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety '2(C15 H23 N O4), C4 H6 O5' _chemical_formula_sum 'C34 H52 N2 O13' _chemical_formula_weight 696.77 _chemical_name_common 11-Aza:D-Mal _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _audit_creation_date 2017-07-17 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2017-08-15 deposited with the CCDC. 2018-01-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.43733(12) _cell_length_b 18.04445(19) _cell_length_c 18.6345(2) _cell_measurement_reflns_used 12158 _cell_measurement_temperature 99.97(10) _cell_measurement_theta_max 75.4300 _cell_measurement_theta_min 3.3990 _cell_volume 3509.54(7) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.97(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _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 39.00 141.00 1.00 8.00 -- 110.57 -30.00 60.00 102 2 \w -71.00 36.00 1.00 4.00 -- -40.57 77.00 120.00 107 3 \w -70.00 33.00 1.00 4.00 -- -40.57 57.00 30.00 103 4 \w -70.00 32.00 1.00 4.00 -- -40.57 57.00 -90.00 102 5 \w 130.00 178.00 1.00 8.00 -- 110.57 30.00 120.00 48 6 \w 122.00 178.00 1.00 8.00 -- 110.57 111.00 90.00 56 7 \w 80.00 118.00 1.00 8.00 -- 110.57 30.00 120.00 38 8 \w 53.00 141.00 1.00 8.00 -- 110.57 -30.00 150.00 88 9 \w 45.00 115.00 1.00 8.00 -- 110.57-111.00 60.00 70 10 \w 33.00 139.00 1.00 8.00 -- 110.57 -30.00 -60.00 106 11 \w 33.00 115.00 1.00 8.00 -- 110.57-111.00 -90.00 82 12 \w 32.00 130.00 1.00 8.00 -- 110.57 -77.00 90.00 98 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0679821000 _diffrn_orient_matrix_UB_12 0.0525212000 _diffrn_orient_matrix_UB_13 -0.0529089000 _diffrn_orient_matrix_UB_21 -0.1049696000 _diffrn_orient_matrix_UB_22 0.0150924000 _diffrn_orient_matrix_UB_23 0.0563410000 _diffrn_orient_matrix_UB_31 0.0782247000 _diffrn_orient_matrix_UB_32 0.0657088000 _diffrn_orient_matrix_UB_33 0.0292547000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_unetI/netI 0.0219 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 19371 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.500 _diffrn_reflns_theta_min 3.409 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90752 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.319 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1496 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.183 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.032 _refine_ls_abs_structure_details ; Flack x determined using 2581 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.06(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 487 _refine_ls_number_reflns 6284 _refine_ls_number_restraints 26 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0284 _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^)+(0.0420P)^2^+0.4980P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.0725 _reflns_Friedel_coverage 0.783 _reflns_Friedel_fraction_full 0.994 _reflns_Friedel_fraction_max 0.994 _reflns_number_gt 6062 _reflns_number_total 6284 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block cpd7_madiha30cult _cod_depositor_comments 'Adding full bibliography for 7229939--7229946.cif.' _cod_original_cell_volume 3509.55(7) _cod_database_code 7229946 _shelx_shelxl_version_number 2014/7 _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. ; _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Restrained distances O22A-C23 1.38 with sigma of 0.02 O22A-C23A 1.4 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C23) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.003 4. Rigid body (RIGU) restrains O22A, C22, C23A, C24 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001 5. Others Fixed Sof: O22(0.9) H22(0.9) O22A(0.1) H22A(0.1) H22C(0.1) C23(0.9) H23A(0.9) H23B(0.9) C23A(0.1) H23C(0.1) 6.a Riding coordinates: C22(H22C,H22B), C23(H23A,H23B) 6.b Ternary CH refined with riding coordinates: C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C2A(H2A), C6A(H6A), C9A(H9A), C11A(H11C), C12A(H12A), C23A(H23C) 6.c Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C4A(H4AA,H4AB), C5A(H5AA, H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB) 6.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C13A(H13D,H13E, H13F), C14A(H14D,H14E,H14F), C15A(H15D,H15E,H15F) 6.e Idealised tetrahedral OH refined as rotating group: O22A(H22A) ; _shelx_res_file ; madiha30cult.res created by SHELXL-2014/7 TITL madiha30 solution in P212121 CELL 1.54184 10.43733 18.04445 18.63452 90 90 90 ZERR 4 0.00012 0.00019 0.0002 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 136 208 8 52 EQIV $1 1+X,+Y,+Z EQIV $2 -1+X,+Y,+Z DFIX 1.38 O22A C23 DFIX 1.4 O22A C23A RIGU 0.003 0.001 O22A C22 C23A C24 ISOR 0.02 0.003 C23 L.S. 6 PLAN 25 TEMP -173 HTAB N11 O20_$1 HTAB N11A O24 HTAB O21 O10_$2 HTAB O23 O10A HTAB CONF BOND fmap 2 acta 133 OMIT 0 135 OMIT 1 5 0 OMIT 4 0 5 OMIT 0 3 1 OMIT 3 0 4 OMIT 0 8 2 OMIT 0 1 10 OMIT 0 9 1 OMIT 0 8 3 OMIT 0 3 6 OMIT 3 0 3 OMIT -2 1 5 OMIT 2 7 0 OMIT 4 0 7 OMIT 1 2 3 OMIT -1 2 3 OMIT 0 7 6 OMIT -2 4 10 OMIT -2 1 4 OMIT 8 11 8 OMIT 0 5 3 OMIT 0 1 6 OMIT 2 4 0 OMIT 5 1 0 OMIT 2 3 8 OMIT 1 0 6 OMIT 0 12 4 OMIT 2 6 0 OMIT -2 8 4 OMIT 0 0 2 OMIT 3 1 2 OMIT 3 13 0 OMIT -3 2 7 OMIT 0 7 4 OMIT 3 2 7 OMIT 5 7 0 OMIT -3 1 2 OMIT 2 3 9 OMIT -2 6 2 OMIT 0 2 6 OMIT -2 3 8 OMIT -2 3 9 OMIT 2 8 4 OMIT 3 4 3 OMIT 1 1 6 OMIT -1 1 6 OMIT 3 7 0 OMIT 5 0 15 OMIT -4 4 15 OMIT 0 3 7 OMIT 6 1 15 OMIT 0 12 7 OMIT -1 11 2 OMIT -6 1 15 OMIT 3 6 0 REM REM REM WGHT 0.042000 0.498000 FVAR 3.07458 O1 4 0.724683 0.732641 0.338500 11.00000 0.02497 0.02041 = 0.02979 0.00145 0.00233 -0.00604 O2 4 0.854405 0.703025 0.329308 11.00000 0.02348 0.03250 = 0.02934 -0.00485 0.00484 -0.00787 O3 4 0.796304 0.579399 0.326436 11.00000 0.02401 0.02609 = 0.02707 -0.00632 0.00637 -0.00144 O10 4 0.817394 0.660603 0.550601 11.00000 0.02591 0.03042 = 0.02084 -0.00193 -0.00325 0.00374 N11 3 0.763654 0.607559 0.446328 11.00000 0.02008 0.01972 = 0.02460 0.00038 -0.00205 0.00270 H11 2 0.819319 0.575740 0.453912 11.00000 0.04296 C1 1 0.633432 0.673870 0.355765 11.00000 0.02191 0.01763 = 0.02090 0.00119 -0.00024 -0.00533 C2 1 0.701911 0.602485 0.376456 11.00000 0.01963 0.01979 = 0.02011 -0.00243 0.00120 -0.00151 AFIX 13 H2 2 0.635908 0.562427 0.379372 11.00000 -1.20000 AFIX 0 C3 1 0.847119 0.639723 0.284656 11.00000 0.03007 0.03527 = 0.02567 -0.00767 0.00749 -0.00729 C4 1 0.763841 0.652498 0.218243 11.00000 0.03953 0.04683 = 0.02061 -0.00293 0.00692 -0.01133 AFIX 23 H4A 2 0.764355 0.706056 0.206723 11.00000 -1.20000 H4B 2 0.802772 0.625974 0.177166 11.00000 -1.20000 AFIX 0 C5 1 0.624851 0.627049 0.226224 11.00000 0.03701 0.03525 = 0.02133 -0.00259 -0.00180 -0.00740 AFIX 23 H5A 2 0.624423 0.572560 0.232430 11.00000 -1.20000 H5B 2 0.579085 0.638192 0.180958 11.00000 -1.20000 AFIX 0 C6 1 0.429125 0.615662 0.306507 11.00000 0.02527 0.02110 = 0.02809 0.00132 -0.00714 -0.00307 AFIX 13 H6 2 0.458173 0.565317 0.321949 11.00000 -1.20000 AFIX 0 C7 1 0.356576 0.650337 0.368669 11.00000 0.02160 0.02562 = 0.03166 0.00399 -0.00316 -0.00214 AFIX 23 H7A 2 0.280733 0.619525 0.379969 11.00000 -1.20000 H7B 2 0.325859 0.700094 0.354350 11.00000 -1.20000 AFIX 0 C8 1 0.440132 0.657388 0.435632 11.00000 0.02212 0.02421 = 0.02534 0.00049 0.00144 -0.00035 AFIX 23 H8A 2 0.467474 0.607531 0.451670 11.00000 -1.20000 H8B 2 0.389958 0.680412 0.474819 11.00000 -1.20000 AFIX 0 C9 1 0.647984 0.719108 0.484177 11.00000 0.02207 0.02148 = 0.02135 -0.00305 0.00001 0.00241 AFIX 13 H9 2 0.696041 0.765607 0.472868 11.00000 -1.20000 AFIX 0 C10 1 0.748366 0.659567 0.495872 11.00000 0.02019 0.02132 = 0.01922 0.00096 0.00201 -0.00074 C11 1 0.549289 0.661783 0.288633 11.00000 0.02751 0.02131 = 0.02137 0.00244 -0.00345 -0.00251 AFIX 13 H11A 2 0.519328 0.711653 0.272318 11.00000 -1.20000 AFIX 0 C12 1 0.558373 0.704914 0.419542 11.00000 0.02011 0.01717 = 0.02313 0.00077 -0.00014 0.00098 AFIX 13 H12 2 0.525581 0.754522 0.404216 11.00000 -1.20000 AFIX 0 C13 1 0.985173 0.620696 0.268390 11.00000 0.03059 0.05500 = 0.03855 -0.01141 0.01383 -0.00859 AFIX 137 H13A 2 1.034190 0.619091 0.313218 11.00000 -1.50000 H13B 2 1.021627 0.658464 0.236587 11.00000 -1.50000 H13C 2 0.989185 0.572201 0.244820 11.00000 -1.50000 AFIX 0 C14 1 0.341556 0.605987 0.241232 11.00000 0.03333 0.02868 = 0.03467 0.00158 -0.01268 -0.00496 AFIX 137 H14A 2 0.266286 0.576751 0.254903 11.00000 -1.50000 H14B 2 0.388349 0.580266 0.203042 11.00000 -1.50000 H14C 2 0.313997 0.654754 0.223982 11.00000 -1.50000 AFIX 0 C15 1 0.576042 0.734033 0.554542 11.00000 0.02810 0.04444 = 0.02495 -0.00903 -0.00034 0.00907 AFIX 137 H15A 2 0.531749 0.688828 0.569845 11.00000 -1.50000 H15B 2 0.513247 0.773660 0.547038 11.00000 -1.50000 H15C 2 0.637193 0.749141 0.591671 11.00000 -1.50000 AFIX 0 O1A 4 0.661994 0.279117 0.332105 11.00000 0.02194 0.01703 = 0.02842 -0.00197 -0.00175 0.00018 O2A 4 0.532464 0.310894 0.332171 11.00000 0.02110 0.02178 = 0.02713 0.00125 -0.00110 -0.00227 O3A 4 0.595644 0.433304 0.340330 11.00000 0.02050 0.01868 = 0.02234 0.00030 -0.00435 0.00096 O10A 4 0.618276 0.332198 0.558135 11.00000 0.02672 0.02809 = 0.02026 0.00227 0.00090 0.00426 N11A 3 0.650377 0.393687 0.454958 11.00000 0.02297 0.01733 = 0.02151 -0.00132 -0.00031 0.00256 H11B 2 0.601523 0.430102 0.471553 11.00000 0.02716 C1A 1 0.758870 0.333913 0.351086 11.00000 0.02080 0.01696 = 0.02223 -0.00233 -0.00123 -0.00062 C2A 1 0.697932 0.404305 0.382229 11.00000 0.01749 0.01793 = 0.02169 -0.00001 -0.00286 0.00042 AFIX 13 H2A 2 0.766232 0.443110 0.384322 11.00000 -1.20000 AFIX 0 C3A 1 0.536335 0.378931 0.294512 11.00000 0.02465 0.01962 = 0.02247 0.00046 -0.00433 -0.00466 C4A 1 0.610079 0.374026 0.223415 11.00000 0.02592 0.02676 = 0.02132 0.00108 -0.00286 -0.00192 AFIX 23 H4AA 2 0.603872 0.322622 0.205173 11.00000 -1.20000 H4AB 2 0.567773 0.406774 0.187983 11.00000 -1.20000 AFIX 0 C5A 1 0.751621 0.395322 0.227923 11.00000 0.02533 0.02718 = 0.02209 0.00194 0.00004 -0.00011 AFIX 23 H5AA 2 0.757150 0.448496 0.240640 11.00000 -1.20000 H5AB 2 0.789919 0.389395 0.179659 11.00000 -1.20000 AFIX 0 C6A 1 0.961481 0.390631 0.296568 11.00000 0.02125 0.02572 = 0.02980 0.00393 0.00262 0.00101 AFIX 13 H6A 2 0.942153 0.441299 0.315419 11.00000 -1.20000 AFIX 0 C7A 1 1.038271 0.348940 0.353870 11.00000 0.02017 0.03157 = 0.03319 0.00174 0.00016 0.00194 AFIX 23 H7AA 2 1.063440 0.299863 0.334756 11.00000 -1.20000 H7AB 2 1.117612 0.376911 0.364546 11.00000 -1.20000 AFIX 0 C8A 1 0.962793 0.338126 0.423153 11.00000 0.02177 0.02802 = 0.02940 0.00379 -0.00212 0.00260 AFIX 23 H8AA 2 0.940469 0.386983 0.443840 11.00000 -1.20000 H8AB 2 1.015900 0.311041 0.458506 11.00000 -1.20000 AFIX 0 C9A 1 0.758255 0.274157 0.473634 11.00000 0.02494 0.02024 = 0.02250 0.00094 0.00028 0.00374 AFIX 13 H9A 2 0.700457 0.233074 0.457849 11.00000 -1.20000 AFIX 0 C10A 1 0.671344 0.336125 0.498659 11.00000 0.02033 0.02074 = 0.02177 -0.00118 -0.00360 -0.00100 C11A 1 0.833207 0.351226 0.281749 11.00000 0.02376 0.02205 = 0.02232 -0.00175 0.00175 0.00194 AFIX 13 H11C 2 0.854001 0.302670 0.258654 11.00000 -1.20000 AFIX 0 C12A 1 0.840559 0.294329 0.407729 11.00000 0.02313 0.01991 = 0.02266 0.00112 0.00024 0.00379 AFIX 13 H12A 2 0.868308 0.246369 0.385785 11.00000 -1.20000 AFIX 0 C13A 1 0.396962 0.399753 0.286139 11.00000 0.02285 0.03190 = 0.03176 0.00334 -0.00522 -0.00231 AFIX 137 H13D 2 0.354878 0.398442 0.333134 11.00000 -1.50000 H13E 2 0.354920 0.364509 0.253788 11.00000 -1.50000 H13F 2 0.390664 0.449817 0.266062 11.00000 -1.50000 AFIX 0 C14A 1 1.041413 0.399261 0.227966 11.00000 0.02595 0.03923 = 0.03454 0.00608 0.00619 0.00172 AFIX 137 H14D 2 1.063018 0.350158 0.209030 11.00000 -1.50000 H14E 2 1.120355 0.426376 0.238979 11.00000 -1.50000 H14F 2 0.991916 0.426759 0.192075 11.00000 -1.50000 AFIX 0 C15A 1 0.835601 0.243527 0.536860 11.00000 0.03288 0.03441 = 0.02516 0.00674 0.00289 0.01203 AFIX 137 H15D 2 0.889091 0.282995 0.557047 11.00000 -1.50000 H15E 2 0.890331 0.202896 0.520185 11.00000 -1.50000 H15F 2 0.776877 0.225089 0.573808 11.00000 -1.50000 AFIX 0 O20 4 -0.011513 0.523029 0.469109 11.00000 0.03656 0.04435 = 0.07459 -0.02985 -0.02206 0.01682 O21 4 0.040659 0.600883 0.557203 11.00000 0.02570 0.03479 = 0.02674 -0.00584 -0.00297 0.00524 H21 2 -0.043859 0.614602 0.557509 11.00000 0.04232 PART 1 O22 4 0.223564 0.480823 0.445617 10.90000 0.04232 0.05995 = 0.03824 -0.02138 -0.00278 0.01409 H22 2 0.151615 0.473054 0.426530 10.90000 0.04918 PART 0 PART 2 O22A 4 0.165959 0.418975 0.567299 10.10000 0.03193 0.03507 = 0.03839 0.00435 0.00444 0.00404 AFIX 147 H22A 2 0.131672 0.417508 0.526541 10.10000 -1.50000 AFIX 0 PART 0 O23 4 0.407160 0.396984 0.593740 11.00000 0.03180 0.03267 = 0.03158 0.00956 0.00639 0.00951 H23 2 0.484512 0.380247 0.581872 11.00000 0.04837 O24 4 0.468378 0.495484 0.529967 11.00000 0.03107 0.02997 = 0.05365 0.01096 0.00989 0.00642 C21 1 0.066191 0.550353 0.509838 11.00000 0.02906 0.02204 = 0.02768 -0.00029 -0.00349 0.00102 C22 1 0.205970 0.527398 0.505326 11.00000 0.02757 0.02989 = 0.02406 -0.00100 0.00275 0.00437 PART 2 AFIX 3 H22C 2 0.217880 0.493888 0.463786 10.10000 -1.20000 PART 0 H22B 2 0.259260 0.571998 0.497296 11.00000 -1.20000 AFIX 0 PART 1 C23 1 0.249852 0.490107 0.573139 10.90000 0.03103 0.04146 = 0.03111 0.00840 0.01045 0.01427 AFIX 3 H23A 2 0.250902 0.527397 0.612119 10.90000 -1.20000 H23B 2 0.191942 0.448897 0.586459 10.90000 -1.20000 AFIX 0 PART 0 PART 2 C23A 1 0.259338 0.476672 0.568929 10.10000 0.03104 0.02924 = 0.01272 0.00602 0.00471 0.00656 AFIX 13 H23C 2 0.246826 0.504676 0.614704 10.10000 -1.20000 AFIX 0 PART 0 C24 1 0.387464 0.461806 0.562805 11.00000 0.02899 0.03205 = 0.02524 0.00294 0.00197 0.00521 HKLF 4 REM madiha30 solution in P212121 REM R1 = 0.0284 for 6062 Fo > 4sig(Fo) and 0.0298 for all 6284 data REM 487 parameters refined using 26 restraints END WGHT 0.0395 0.4618 REM Instructions for potential hydrogen bonds HTAB N11 O20_$1 HTAB C2 O3A EQIV $3 -x+3/2, -y+1, z-1/2 HTAB C4 O10A_$3 HTAB N11A O24 EQIV $4 x+1/2, -y+1/2, -z+1 HTAB C12A O23_$4 HTAB O21 O10_$2 HTAB O22 O20 HTAB O22A O20 HTAB O23 O10A REM Highest difference peak 0.183, deepest hole -0.160, 1-sigma level 0.032 Q1 1 0.4247 0.4731 0.4870 11.00000 0.05 0.18 Q2 1 0.1927 0.4420 0.4788 11.00000 0.05 0.18 Q3 1 -0.0480 0.4999 0.5261 11.00000 0.05 0.17 Q4 1 0.5857 0.6648 0.3263 11.00000 0.05 0.15 Q5 1 0.7638 0.5022 0.0921 11.00000 0.05 0.14 Q6 1 0.6547 0.6378 0.3700 11.00000 0.05 0.14 Q7 1 0.4973 0.6797 0.4257 11.00000 0.05 0.12 Q8 1 0.5812 0.3781 0.2577 11.00000 0.05 0.12 Q9 1 0.8092 0.3426 0.3205 11.00000 0.05 0.12 Q10 1 0.8007 0.3181 0.3801 11.00000 0.05 0.12 Q11 1 0.4768 0.5999 0.5564 11.00000 0.05 0.12 Q12 1 0.1945 0.5236 0.5530 11.00000 0.05 0.11 Q13 1 0.6593 0.2383 0.3669 11.00000 0.05 0.11 Q14 1 0.8967 0.3214 0.4166 11.00000 0.05 0.11 Q15 1 0.8003 0.6468 0.2502 11.00000 0.05 0.11 Q16 1 0.4567 0.3853 0.2905 11.00000 0.05 0.11 Q17 1 0.3970 0.6578 0.4046 11.00000 0.05 0.11 Q18 1 0.1476 0.5743 0.6212 11.00000 0.05 0.10 Q19 1 0.0467 0.5526 0.5590 11.00000 0.05 0.10 Q20 1 0.5924 0.6886 0.3877 11.00000 0.05 0.10 Q21 1 1.0290 0.4348 0.1832 11.00000 0.05 0.10 Q22 1 0.6585 0.2480 0.2953 11.00000 0.05 0.10 Q23 1 0.6592 0.2752 0.2795 11.00000 0.05 0.10 Q24 1 0.6770 0.3869 0.2272 11.00000 0.05 0.10 Q25 1 0.7842 0.3779 0.2683 11.00000 0.05 0.10 ; _shelx_res_checksum 53549 _olex2_date_sample_data_collection 2017-06-19 _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 1.356 _oxdiff_exptl_absorpt_empirical_full_min 0.866 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 O1 O 0.72468(13) 0.73264(8) 0.33850(8) 0.0251(3) Uani 1 1 d . . . . . O2 O 0.85440(14) 0.70303(8) 0.32931(8) 0.0284(3) Uani 1 1 d . . . . . O3 O 0.79630(13) 0.57940(8) 0.32644(8) 0.0257(3) Uani 1 1 d . . . . . O10 O 0.81739(14) 0.66060(8) 0.55060(7) 0.0257(3) Uani 1 1 d . . . . . N11 N 0.76365(16) 0.60756(9) 0.44633(9) 0.0215(3) Uani 1 1 d . . . . . H11 H 0.819(3) 0.5757(17) 0.4539(16) 0.043(8) Uiso 1 1 d . . . . . C1 C 0.63343(18) 0.67387(10) 0.35576(10) 0.0201(4) Uani 1 1 d . . . . . C2 C 0.70191(18) 0.60248(11) 0.37646(10) 0.0198(4) Uani 1 1 d . . . . . H2 H 0.6359 0.5624 0.3794 0.024 Uiso 1 1 calc R . . . . C3 C 0.8471(2) 0.63972(13) 0.28466(11) 0.0303(5) Uani 1 1 d . . . . . C4 C 0.7638(2) 0.65250(14) 0.21824(11) 0.0357(5) Uani 1 1 d . . . . . H4A H 0.7644 0.7061 0.2067 0.043 Uiso 1 1 calc R . . . . H4B H 0.8028 0.6260 0.1772 0.043 Uiso 1 1 calc R . . . . C5 C 0.6249(2) 0.62705(13) 0.22622(11) 0.0312(5) Uani 1 1 d . . . . . H5A H 0.6244 0.5726 0.2324 0.037 Uiso 1 1 calc R . . . . H5B H 0.5791 0.6382 0.1810 0.037 Uiso 1 1 calc R . . . . C6 C 0.4291(2) 0.61566(11) 0.30651(11) 0.0248(4) Uani 1 1 d . . . . . H6 H 0.4582 0.5653 0.3219 0.030 Uiso 1 1 calc R . . . . C7 C 0.3566(2) 0.65034(11) 0.36867(11) 0.0263(4) Uani 1 1 d . . . . . H7A H 0.2807 0.6195 0.3800 0.032 Uiso 1 1 calc R . . . . H7B H 0.3259 0.7001 0.3543 0.032 Uiso 1 1 calc R . . . . C8 C 0.44013(19) 0.65739(11) 0.43563(11) 0.0239(4) Uani 1 1 d . . . . . H8A H 0.4675 0.6075 0.4517 0.029 Uiso 1 1 calc R . . . . H8B H 0.3900 0.6804 0.4748 0.029 Uiso 1 1 calc R . . . . C9 C 0.64798(18) 0.71911(11) 0.48418(10) 0.0216(4) Uani 1 1 d . . . . . H9 H 0.6960 0.7656 0.4729 0.026 Uiso 1 1 calc R . . . . C10 C 0.74837(19) 0.65957(10) 0.49587(10) 0.0202(4) Uani 1 1 d . . . . . C11 C 0.5493(2) 0.66178(11) 0.28863(10) 0.0234(4) Uani 1 1 d . . . . . H11A H 0.5193 0.7117 0.2723 0.028 Uiso 1 1 calc R . . . . C12 C 0.55837(18) 0.70491(10) 0.41954(10) 0.0201(4) Uani 1 1 d . . . . . H12 H 0.5256 0.7545 0.4042 0.024 Uiso 1 1 calc R . . . . C13 C 0.9852(2) 0.62070(16) 0.26839(14) 0.0414(6) Uani 1 1 d . . . . . H13A H 1.0342 0.6191 0.3132 0.062 Uiso 1 1 calc GR . . . . H13B H 1.0216 0.6585 0.2366 0.062 Uiso 1 1 calc GR . . . . H13C H 0.9892 0.5722 0.2448 0.062 Uiso 1 1 calc GR . . . . C14 C 0.3416(2) 0.60599(13) 0.24123(12) 0.0322(5) Uani 1 1 d . . . . . H14A H 0.2663 0.5768 0.2549 0.048 Uiso 1 1 calc GR . . . . H14B H 0.3883 0.5803 0.2030 0.048 Uiso 1 1 calc GR . . . . H14C H 0.3140 0.6548 0.2240 0.048 Uiso 1 1 calc GR . . . . C15 C 0.5760(2) 0.73403(14) 0.55454(12) 0.0325(5) Uani 1 1 d . . . . . H15A H 0.5317 0.6888 0.5698 0.049 Uiso 1 1 calc GR . . . . H15B H 0.5132 0.7737 0.5470 0.049 Uiso 1 1 calc GR . . . . H15C H 0.6372 0.7491 0.5917 0.049 Uiso 1 1 calc GR . . . . O1A O 0.66199(13) 0.27912(7) 0.33211(7) 0.0225(3) Uani 1 1 d . . . . . O2A O 0.53246(13) 0.31089(7) 0.33217(8) 0.0233(3) Uani 1 1 d . . . . . O3A O 0.59564(13) 0.43330(7) 0.34033(7) 0.0205(3) Uani 1 1 d . . . . . O10A O 0.61828(14) 0.33220(8) 0.55814(7) 0.0250(3) Uani 1 1 d . . . . . N11A N 0.65038(16) 0.39369(9) 0.45496(9) 0.0206(3) Uani 1 1 d . . . . . H11B H 0.602(3) 0.4301(14) 0.4716(14) 0.027(6) Uiso 1 1 d . . . . . C1A C 0.75887(19) 0.33391(10) 0.35109(10) 0.0200(4) Uani 1 1 d . . . . . C2A C 0.69793(18) 0.40431(10) 0.38223(10) 0.0190(4) Uani 1 1 d . . . . . H2A H 0.7662 0.4431 0.3843 0.023 Uiso 1 1 calc R . . . . C3A C 0.5363(2) 0.37893(10) 0.29451(10) 0.0222(4) Uani 1 1 d . . . . . C4A C 0.6101(2) 0.37403(11) 0.22341(11) 0.0247(4) Uani 1 1 d . . . . . H4AA H 0.6039 0.3226 0.2052 0.030 Uiso 1 1 calc R . . . . H4AB H 0.5678 0.4068 0.1880 0.030 Uiso 1 1 calc R . . . . C5A C 0.7516(2) 0.39532(11) 0.22792(10) 0.0249(4) Uani 1 1 d . . . . . H5AA H 0.7572 0.4485 0.2406 0.030 Uiso 1 1 calc R . . . . H5AB H 0.7899 0.3894 0.1797 0.030 Uiso 1 1 calc R . . . . C6A C 0.96148(19) 0.39063(12) 0.29657(11) 0.0256(4) Uani 1 1 d . . . . . H6A H 0.9422 0.4413 0.3154 0.031 Uiso 1 1 calc R . . . . C7A C 1.0383(2) 0.34894(12) 0.35387(12) 0.0283(4) Uani 1 1 d . . . . . H7AA H 1.0634 0.2999 0.3348 0.034 Uiso 1 1 calc R . . . . H7AB H 1.1176 0.3769 0.3645 0.034 Uiso 1 1 calc R . . . . C8A C 0.9628(2) 0.33813(12) 0.42315(11) 0.0264(4) Uani 1 1 d . . . . . H8AA H 0.9405 0.3870 0.4438 0.032 Uiso 1 1 calc R . . . . H8AB H 1.0159 0.3110 0.4585 0.032 Uiso 1 1 calc R . . . . C9A C 0.7583(2) 0.27416(11) 0.47363(10) 0.0226(4) Uani 1 1 d . . . . . H9A H 0.7005 0.2331 0.4578 0.027 Uiso 1 1 calc R . . . . C10A C 0.67134(18) 0.33613(11) 0.49866(10) 0.0209(4) Uani 1 1 d . . . . . C11A C 0.83321(19) 0.35123(11) 0.28175(10) 0.0227(4) Uani 1 1 d . . . . . H11C H 0.8540 0.3027 0.2587 0.027 Uiso 1 1 calc R . . . . C12A C 0.84056(19) 0.29433(10) 0.40773(10) 0.0219(4) Uani 1 1 d . . . . . H12A H 0.8683 0.2464 0.3858 0.026 Uiso 1 1 calc R . . . . C13A C 0.3970(2) 0.39975(12) 0.28614(12) 0.0288(4) Uani 1 1 d . . . . . H13D H 0.3549 0.3984 0.3331 0.043 Uiso 1 1 calc GR . . . . H13E H 0.3549 0.3645 0.2538 0.043 Uiso 1 1 calc GR . . . . H13F H 0.3907 0.4498 0.2661 0.043 Uiso 1 1 calc GR . . . . C14A C 1.0414(2) 0.39926(13) 0.22797(12) 0.0332(5) Uani 1 1 d . . . . . H14D H 1.0630 0.3502 0.2090 0.050 Uiso 1 1 calc GR . . . . H14E H 1.1204 0.4264 0.2390 0.050 Uiso 1 1 calc GR . . . . H14F H 0.9919 0.4268 0.1921 0.050 Uiso 1 1 calc GR . . . . C15A C 0.8356(2) 0.24353(13) 0.53686(11) 0.0308(5) Uani 1 1 d . . . . . H15D H 0.8891 0.2830 0.5570 0.046 Uiso 1 1 calc GR . . . . H15E H 0.8903 0.2029 0.5202 0.046 Uiso 1 1 calc GR . . . . H15F H 0.7769 0.2251 0.5738 0.046 Uiso 1 1 calc GR . . . . O20 O -0.01151(18) 0.52303(10) 0.46911(12) 0.0518(5) Uani 1 1 d . . . . . O21 O 0.04066(15) 0.60088(8) 0.55720(8) 0.0291(3) Uani 1 1 d . . . . . H21 H -0.044(3) 0.6146(16) 0.5575(16) 0.042(8) Uiso 1 1 d . . . . . O22 O 0.2236(2) 0.48082(13) 0.44562(11) 0.0468(5) Uani 0.9 1 d . . P A 1 H22 H 0.152(4) 0.473(2) 0.4265(19) 0.049(10) Uiso 0.9 1 d . . P B 1 O22A O 0.1660(14) 0.4190(8) 0.5673(9) 0.035(3) Uani 0.1 1 d D U P A 2 H22A H 0.1317 0.4175 0.5265 0.053 Uiso 0.1 1 calc GR . P A 2 O23 O 0.40716(16) 0.39698(9) 0.59374(8) 0.0320(3) Uani 1 1 d . . . . . H23 H 0.485(3) 0.3802(17) 0.5819(16) 0.048(8) Uiso 1 1 d . . . . . O24 O 0.46838(16) 0.49548(9) 0.52997(10) 0.0382(4) Uani 1 1 d . . . . . C21 C 0.0662(2) 0.55035(11) 0.50984(11) 0.0263(4) Uani 1 1 d . . . . . C22 C 0.2060(2) 0.52740(13) 0.50533(11) 0.0272(4) Uani 1 1 d . U . . . H22C H 0.2179 0.4939 0.4638 0.033 Uiso 0.1 1 d R . P A 2 H22B H 0.2593 0.5720 0.4973 0.033 Uiso 1 1 d R . . A . C23 C 0.2499(5) 0.4901(2) 0.5731(4) 0.0345(11) Uani 0.9 1 d D U P A 1 H23A H 0.2509 0.5274 0.6121 0.041 Uiso 0.9 1 d R . P A 1 H23B H 0.1919 0.4489 0.5865 0.041 Uiso 0.9 1 d R . P A 1 C23A C 0.259(5) 0.477(2) 0.569(4) 0.024(5) Uani 0.1 1 d D U P A 2 H23C H 0.2468 0.5047 0.6147 0.029 Uiso 0.1 1 calc R . P A 2 C24 C 0.3875(2) 0.46181(12) 0.56281(11) 0.0288(4) Uani 1 1 d . U . . . 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 O1 0.0250(7) 0.0204(7) 0.0298(7) 0.0015(5) 0.0023(6) -0.0060(6) O2 0.0235(7) 0.0325(8) 0.0293(7) -0.0048(6) 0.0048(6) -0.0079(6) O3 0.0240(7) 0.0261(7) 0.0271(7) -0.0063(6) 0.0064(6) -0.0014(6) O10 0.0259(7) 0.0304(7) 0.0208(7) -0.0019(6) -0.0032(5) 0.0037(6) N11 0.0201(8) 0.0197(8) 0.0246(8) 0.0004(6) -0.0020(7) 0.0027(7) C1 0.0219(9) 0.0176(9) 0.0209(9) 0.0012(7) -0.0002(7) -0.0053(8) C2 0.0196(8) 0.0198(9) 0.0201(9) -0.0024(7) 0.0012(7) -0.0015(8) C3 0.0301(11) 0.0353(11) 0.0257(10) -0.0077(9) 0.0075(9) -0.0073(9) C4 0.0395(12) 0.0468(13) 0.0206(9) -0.0029(9) 0.0069(9) -0.0113(11) C5 0.0370(12) 0.0352(11) 0.0213(9) -0.0026(9) -0.0018(9) -0.0074(10) C6 0.0253(10) 0.0211(9) 0.0281(10) 0.0013(8) -0.0071(8) -0.0031(8) C7 0.0216(10) 0.0256(10) 0.0317(11) 0.0040(8) -0.0032(8) -0.0021(8) C8 0.0221(9) 0.0242(9) 0.0253(9) 0.0005(8) 0.0014(8) -0.0004(8) C9 0.0221(9) 0.0215(9) 0.0213(9) -0.0031(7) 0.0000(8) 0.0024(8) C10 0.0202(8) 0.0213(9) 0.0192(8) 0.0010(7) 0.0020(7) -0.0007(8) C11 0.0275(10) 0.0213(9) 0.0214(9) 0.0024(8) -0.0034(8) -0.0025(8) C12 0.0201(9) 0.0172(8) 0.0231(9) 0.0008(7) -0.0001(7) 0.0010(7) C13 0.0306(12) 0.0550(15) 0.0385(13) -0.0114(12) 0.0138(10) -0.0086(11) C14 0.0333(11) 0.0287(11) 0.0347(11) 0.0016(9) -0.0127(9) -0.0050(9) C15 0.0281(10) 0.0444(13) 0.0249(10) -0.0090(9) -0.0003(8) 0.0091(9) O1A 0.0219(7) 0.0170(6) 0.0284(7) -0.0020(5) -0.0018(5) 0.0002(5) O2A 0.0211(7) 0.0218(7) 0.0271(7) 0.0012(6) -0.0011(6) -0.0023(5) O3A 0.0205(6) 0.0187(6) 0.0223(6) 0.0003(5) -0.0043(5) 0.0010(5) O10A 0.0267(7) 0.0281(7) 0.0203(6) 0.0023(6) 0.0009(5) 0.0043(6) N11A 0.0230(8) 0.0173(7) 0.0215(8) -0.0013(6) -0.0003(6) 0.0026(7) C1A 0.0208(9) 0.0170(8) 0.0222(9) -0.0023(7) -0.0012(7) -0.0006(7) C2A 0.0175(8) 0.0179(9) 0.0217(9) 0.0000(7) -0.0029(7) 0.0004(7) C3A 0.0247(10) 0.0196(9) 0.0225(9) 0.0005(7) -0.0043(8) -0.0047(8) C4A 0.0259(10) 0.0268(10) 0.0213(9) 0.0011(8) -0.0029(8) -0.0019(8) C5A 0.0253(9) 0.0272(10) 0.0221(9) 0.0019(8) 0.0000(8) -0.0001(9) C6A 0.0213(9) 0.0257(10) 0.0298(10) 0.0039(8) 0.0026(8) 0.0010(8) C7A 0.0202(9) 0.0316(11) 0.0332(11) 0.0017(9) 0.0002(8) 0.0019(8) C8A 0.0218(9) 0.0280(10) 0.0294(10) 0.0038(8) -0.0021(8) 0.0026(9) C9A 0.0249(9) 0.0202(9) 0.0225(9) 0.0009(7) 0.0003(8) 0.0037(8) C10A 0.0203(9) 0.0207(9) 0.0218(9) -0.0012(8) -0.0036(7) -0.0010(7) C11A 0.0238(10) 0.0220(9) 0.0223(9) -0.0017(7) 0.0017(8) 0.0019(8) C12A 0.0231(9) 0.0199(9) 0.0227(9) 0.0011(7) 0.0002(8) 0.0038(8) C13A 0.0228(10) 0.0319(10) 0.0318(10) 0.0033(9) -0.0052(8) -0.0023(9) C14A 0.0260(10) 0.0392(12) 0.0345(11) 0.0061(10) 0.0062(9) 0.0017(10) C15A 0.0329(11) 0.0344(11) 0.0252(10) 0.0067(8) 0.0029(9) 0.0120(9) O20 0.0366(9) 0.0444(10) 0.0746(13) -0.0298(10) -0.0221(9) 0.0168(8) O21 0.0257(7) 0.0348(8) 0.0267(7) -0.0058(6) -0.0030(6) 0.0052(7) O22 0.0423(12) 0.0599(13) 0.0382(10) -0.0214(10) -0.0028(9) 0.0141(10) O22A 0.032(4) 0.035(4) 0.038(7) 0.004(4) 0.004(4) 0.004(3) O23 0.0318(8) 0.0327(8) 0.0316(7) 0.0096(7) 0.0064(6) 0.0095(7) O24 0.0311(8) 0.0300(8) 0.0537(10) 0.0110(7) 0.0099(7) 0.0064(7) C21 0.0291(10) 0.0220(9) 0.0277(10) -0.0003(8) -0.0035(8) 0.0010(8) C22 0.0276(10) 0.0299(10) 0.0241(9) -0.0010(8) 0.0028(8) 0.0044(8) C23 0.0310(15) 0.041(2) 0.031(2) 0.008(2) 0.0104(13) 0.0143(16) C23A 0.031(6) 0.029(8) 0.013(10) 0.006(7) 0.005(5) 0.007(5) C24 0.0290(10) 0.0321(11) 0.0252(10) 0.0029(9) 0.0020(9) 0.0052(9) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 O2 111.30(13) C3 O2 O1 108.26(14) C2 O3 C3 112.90(15) C10 N11 C2 127.88(17) O1 C1 C2 111.33(15) O1 C1 C11 107.15(14) O1 C1 C12 103.83(14) C2 C1 C11 110.65(16) C2 C1 C12 110.70(15) C12 C1 C11 112.95(16) O3 C2 N11 107.38(15) O3 C2 C1 114.08(16) N11 C2 C1 112.40(15) O2 C3 O3 108.19(16) O2 C3 C4 112.62(19) O2 C3 C13 104.47(18) O3 C3 C4 110.01(17) O3 C3 C13 106.7(2) C13 C3 C4 114.43(19) C5 C4 C3 114.53(18) C4 C5 C11 115.95(18) C7 C6 C11 110.37(16) C7 C6 C14 110.80(17) C14 C6 C11 112.05(17) C6 C7 C8 111.88(16) C7 C8 C12 110.28(16) C10 C9 C12 114.36(15) C10 C9 C15 109.85(16) C15 C9 C12 113.49(16) O10 C10 N11 120.65(18) O10 C10 C9 120.36(17) N11 C10 C9 118.98(17) C5 C11 C1 112.23(17) C5 C11 C6 111.13(16) C6 C11 C1 111.34(15) C1 C12 C8 111.07(15) C1 C12 C9 110.86(15) C8 C12 C9 115.30(16) C1A O1A O2A 111.93(12) C3A O2A O1A 108.19(13) C2A O3A C3A 113.41(14) C10A N11A C2A 127.81(17) O1A C1A C2A 111.45(15) O1A C1A C11A 106.48(14) O1A C1A C12A 103.69(14) C2A C1A C11A 111.00(15) C12A C1A C2A 110.84(15) C12A C1A C11A 113.09(16) O3A C2A N11A 107.67(15) O3A C2A C1A 114.08(15) N11A C2A C1A 112.61(15) O2A C3A O3A 108.02(14) O2A C3A C4A 113.11(16) O2A C3A C13A 103.86(16) O3A C3A C4A 109.60(15) O3A C3A C13A 107.80(16) C13A C3A C4A 114.09(17) C5A C4A C3A 115.00(16) C4A C5A C11A 116.16(16) C7A C6A C11A 110.66(17) C7A C6A C14A 110.24(17) C14A C6A C11A 111.71(17) C8A C7A C6A 112.49(17) C7A C8A C12A 109.77(17) C10A C9A C12A 113.88(16) C10A C9A C15A 110.21(16) C15A C9A C12A 113.84(17) O10A C10A N11A 120.99(18) O10A C10A C9A 120.03(17) N11A C10A C9A 118.95(17) C1A C11A C6A 112.41(16) C5A C11A C1A 111.93(16) C5A C11A C6A 111.06(16) C1A C12A C9A 110.39(16) C8A C12A C1A 110.66(16) C8A C12A C9A 115.93(16) O20 C21 O21 125.0(2) O20 C21 C22 119.72(19) O21 C21 C22 115.27(18) O22 C22 C21 109.40(19) O22 C22 C23 111.0(3) C21 C22 C23A 116.7(19) C23 C22 C21 111.6(2) C22 C23 C24 109.2(4) O22A C23A C22 99(3) C24 C23A O22A 122(4) C24 C23A C22 113(4) O23 C24 C23 112.7(3) O23 C24 C23A 107(2) O24 C24 O23 124.0(2) O24 C24 C23 123.4(3) O24 C24 C23A 129(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 O2 1.466(2) O1 C1 1.461(2) O2 C3 1.415(3) O3 C2 1.419(2) O3 C3 1.440(3) O10 C10 1.249(2) N11 C2 1.456(2) N11 C10 1.326(3) C1 C2 1.523(3) C1 C11 1.544(3) C1 C12 1.530(3) C3 C4 1.530(3) C3 C13 1.512(3) C4 C5 1.529(3) C5 C11 1.539(3) C6 C7 1.519(3) C6 C11 1.542(3) C6 C14 1.531(3) C7 C8 1.528(3) C8 C12 1.532(3) C9 C10 1.516(3) C9 C12 1.546(3) C9 C15 1.535(3) O1A O2A 1.4685(19) O1A C1A 1.458(2) O2A C3A 1.415(2) O3A C2A 1.422(2) O3A C3A 1.440(2) O10A C10A 1.241(2) N11A C2A 1.456(2) N11A C10A 1.338(3) C1A C2A 1.535(3) C1A C11A 1.539(3) C1A C12A 1.533(3) C3A C4A 1.535(3) C3A C13A 1.511(3) C4A C5A 1.529(3) C5A C11A 1.538(3) C6A C7A 1.532(3) C6A C11A 1.541(3) C6A C14A 1.534(3) C7A C8A 1.525(3) C8A C12A 1.528(3) C9A C10A 1.513(3) C9A C12A 1.542(3) C9A C15A 1.531(3) O20 C21 1.215(3) O21 C21 1.297(3) O22 C22 1.406(3) O22A C23A 1.43(3) O23 C24 1.320(3) O24 C24 1.207(3) C21 C22 1.519(3) C22 C23 1.503(8) C22 C23A 1.60(6) C23 C24 1.536(5) C23A C24 1.37(5) 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 N11 H11 O20 0.83(3) 2.03(3) 2.831(2) 164(3) 1_655 N11A H11B O24 0.89(3) 2.12(3) 2.989(2) 165(2) . O21 H21 O10 0.92(3) 1.67(3) 2.570(2) 165(3) 1_455 O23 H23 O10A 0.89(3) 1.70(3) 2.581(2) 169(3) . 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 O1 O2 C3 O3 -75.51(19) O1 O2 C3 C4 46.3(2) O1 O2 C3 C13 171.05(17) O1 C1 C2 O3 -51.2(2) O1 C1 C2 N11 71.32(19) O1 C1 C11 C5 69.0(2) O1 C1 C11 C6 -165.67(15) O1 C1 C12 C8 168.59(15) O1 C1 C12 C9 -61.85(18) O2 O1 C1 C2 13.3(2) O2 O1 C1 C11 -107.80(16) O2 O1 C1 C12 132.45(14) O2 C3 C4 C5 -95.2(2) O3 C3 C4 C5 25.5(3) C1 O1 O2 C3 46.85(19) C2 O3 C3 O2 36.1(2) C2 O3 C3 C4 -87.3(2) C2 O3 C3 C13 148.00(17) C2 N11 C10 O10 -172.89(18) C2 N11 C10 C9 5.5(3) C2 C1 C11 C5 -52.5(2) C2 C1 C11 C6 72.8(2) C2 C1 C12 C8 -71.8(2) C2 C1 C12 C9 57.7(2) C3 O3 C2 N11 -100.28(18) C3 O3 C2 C1 25.0(2) C3 C4 C5 C11 57.4(3) C4 C5 C11 C1 -36.5(3) C4 C5 C11 C6 -161.93(19) C6 C7 C8 C12 58.9(2) C7 C6 C11 C1 53.5(2) C7 C6 C11 C5 179.42(16) C7 C8 C12 C1 -55.4(2) C7 C8 C12 C9 177.45(16) C10 N11 C2 O3 138.63(19) C10 N11 C2 C1 12.4(3) C10 C9 C12 C1 -40.4(2) C10 C9 C12 C8 86.9(2) C11 C1 C2 O3 67.8(2) C11 C1 C2 N11 -169.64(15) C11 C1 C12 C8 52.9(2) C11 C1 C12 C9 -177.58(15) C11 C6 C7 C8 -57.9(2) C12 C1 C2 O3 -166.19(15) C12 C1 C2 N11 -43.6(2) C12 C1 C11 C5 -177.24(16) C12 C1 C11 C6 -51.9(2) C12 C9 C10 O10 -172.36(17) C12 C9 C10 N11 9.2(3) C13 C3 C4 C5 145.7(2) C14 C6 C7 C8 177.41(17) C14 C6 C11 C1 177.51(17) C14 C6 C11 C5 -56.6(2) C15 C9 C10 O10 -43.4(2) C15 C9 C10 N11 138.19(19) C15 C9 C12 C1 -167.48(17) C15 C9 C12 C8 -40.2(2) O1A O2A C3A O3A -75.53(16) O1A O2A C3A C4A 45.96(19) O1A O2A C3A C13A 170.18(14) O1A C1A C2A O3A -49.4(2) O1A C1A C2A N11A 73.75(19) O1A C1A C11A C5A 70.47(19) O1A C1A C11A C6A -163.73(15) O1A C1A C12A C8A 168.88(15) O1A C1A C12A C9A -61.42(19) O2A O1A C1A C2A 12.86(19) O2A O1A C1A C11A -108.32(15) O2A O1A C1A C12A 132.15(14) O2A C3A C4A C5A -93.6(2) O3A C3A C4A C5A 27.0(2) C1A O1A O2A C3A 46.68(17) C2A O3A C3A O2A 37.4(2) C2A O3A C3A C4A -86.21(18) C2A O3A C3A C13A 149.08(16) C2A N11A C10A O10A -175.62(17) C2A N11A C10A C9A 2.6(3) C2A C1A C11A C5A -51.0(2) C2A C1A C11A C6A 74.8(2) C2A C1A C12A C8A -71.4(2) C2A C1A C12A C9A 58.3(2) C3A O3A C2A N11A -102.89(17) C3A O3A C2A C1A 22.9(2) C3A C4A C5A C11A 57.1(2) C4A C5A C11A C1A -37.9(2) C4A C5A C11A C6A -164.47(17) C6A C7A C8A C12A 59.4(2) C7A C6A C11A C1A 50.1(2) C7A C6A C11A C5A 176.33(17) C7A C8A C12A C1A -57.4(2) C7A C8A C12A C9A 175.92(16) C10A N11A C2A O3A 137.66(18) C10A N11A C2A C1A 11.0(3) C10A C9A C12A C1A -45.0(2) C10A C9A C12A C8A 81.8(2) C11A C1A C2A O3A 69.2(2) C11A C1A C2A N11A -167.74(15) C11A C1A C12A C8A 54.0(2) C11A C1A C12A C9A -176.33(15) C11A C6A C7A C8A -55.4(2) C12A C1A C2A O3A -164.30(15) C12A C1A C2A N11A -41.2(2) C12A C1A C11A C5A -176.30(16) C12A C1A C11A C6A -50.5(2) C12A C9A C10A O10A -166.76(17) C12A C9A C10A N11A 15.0(3) C13A C3A C4A C5A 147.95(18) C14A C6A C7A C8A -179.47(18) C14A C6A C11A C1A 173.29(17) C14A C6A C11A C5A -60.4(2) C15A C9A C10A O10A -37.4(3) C15A C9A C10A N11A 144.37(18) C15A C9A C12A C1A -172.47(17) C15A C9A C12A C8A -45.7(2) O20 C21 C22 O22 6.4(3) O20 C21 C22 C23 -116.8(3) O20 C21 C22 C23A -108.1(17) O21 C21 C22 O22 -171.56(19) O21 C21 C22 C23 65.3(3) O21 C21 C22 C23A 74.0(17) O22 C22 C23 C24 52.5(4) O22A C23A C24 O23 -33(6) O22A C23A C24 O24 140(3) C21 C22 C23 C24 174.8(2) C21 C22 C23A O22A 53(3) C21 C22 C23A C24 -176.7(19) C22 C23 C24 O23 -141.8(2) C22 C23 C24 O24 38.3(5) C22 C23A C24 O23 -151.3(19) C22 C23A C24 O24 22(4)