#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:21:57 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229075 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229944.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_7229944 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:L-Mal _space_group_crystal_system orthorhombic _space_group_IT_number 18 _space_group_name_Hall 'P 2 2ab' _space_group_name_H-M_alt 'P 21 21 2' _symmetry_space_group_name_Hall 'P 2 2ab' _symmetry_space_group_name_H-M 'P 21 21 2' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _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 2 _cell_length_a 17.7811(3) _cell_length_b 10.3174(2) _cell_length_c 9.49693(15) _cell_measurement_reflns_used 3703 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 75.1850 _cell_measurement_theta_min 4.9790 _cell_volume 1742.26(5) _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _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 94.00 178.00 1.00 5.00 -- 110.57 45.00 0.00 84 2 \w 36.00 136.00 1.00 5.00 -- 110.57 -61.00-150.00 100 3 \w 33.00 108.00 1.00 5.00 -- 110.57 -94.00 60.00 75 4 \w 36.00 108.00 1.00 5.00 -- 110.57-111.00 30.00 72 5 \w 25.00 97.00 1.00 1.00 -- 40.57-125.00 60.00 72 6 \w -114.00 -3.00 1.00 1.00 -- -40.57 -19.00 -30.00 111 ; _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 -0.0718188000 _diffrn_orient_matrix_UB_12 -0.0820565000 _diffrn_orient_matrix_UB_13 -0.0169375000 _diffrn_orient_matrix_UB_21 0.0458874000 _diffrn_orient_matrix_UB_22 -0.1240724000 _diffrn_orient_matrix_UB_23 0.0275833000 _diffrn_orient_matrix_UB_31 -0.0156953000 _diffrn_orient_matrix_UB_32 0.0126916000 _diffrn_orient_matrix_UB_33 0.1589443000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 4942 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.415 _diffrn_reflns_theta_min 5.280 _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 0.848 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88351 _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 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 748 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.179 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.029 _refine_ls_abs_structure_details ; Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.01(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 3094 _refine_ls_number_restraints 58 _refine_ls_restrained_S_all 1.002 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0258 _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^)+(0.0595P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0743 _refine_ls_wR_factor_ref 0.0752 _reflns_Friedel_coverage 0.725 _reflns_Friedel_fraction_full 0.981 _reflns_Friedel_fraction_max 0.980 _reflns_number_gt 3011 _reflns_number_total 3094 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block cpd6_madiha16a _cod_depositor_comments 'Adding full bibliography for 7229939--7229946.cif.' _cod_database_code 7229944 _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 99.20 _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 2. Restrained distances O23-H23 0.9 with sigma of 0.02 O21-H21 = O23-H23 0.9 with sigma of 0.05 C22-C24 \\sim C21-C23 with sigma of 0.02 3. Rigid body (RIGU) restrains O20, O21, H21, O22, O23, H23, O24, C21, C22, C23, C24 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001 4. Others Fixed Sof: O20(0.5) O21(0.5) H21(0.5) O22(0.5) H22(0.5) O23(0.5) H23(0.5) O24(0.5) C21(0.5) C22(0.5) H22A(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) 5.a Ternary CH refined with riding coordinates: C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C22(H22A) 5.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C23(H23A,H23B) 5.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _shelx_res_file ; madiha16a.res created by SHELXL-2014/7 TITL madiha16a in P21212 #18 REM reset to P21212 #18 CELL 1.54184 17.78107 10.31743 9.49693 90 90 90 ZERR 2 0.0003 0.0002 0.00015 0 0 0 LATT -1 SYMM -X,-Y,+Z SYMM 0.5+X,0.5-Y,-Z SYMM 0.5-X,0.5+Y,-Z SFAC C H N O UNIT 68 104 4 26 EQIV $1 1-X,-Y,+Z DFIX 0.9 O23 H23 DFIX 0.9 0.05 O21 H21 O23 H23 SADI C22 C24 C21 C23 RIGU 0.001 0.001 O20 O21 H21 O22 O23 H23 O24 C21 C22 C23 C24 L.S. 8 PLAN 20 TEMP -173 HTAB O21 O10 HTAB N11 O20 HTAB N11 O24_$1 HTAB O23 O10_$1 FREE C23 C21_$1 CONF BOND fmap 2 acta 133 OMIT 0 135 OMIT 2 0 1 OMIT 0 1 3 OMIT 7 1 0 OMIT 0 2 4 OMIT 2 0 0 OMIT 2 4 0 OMIT 1 0 3 OMIT 1 1 0 OMIT 0 5 8 OMIT 0 4 0 OMIT 0 2 1 OMIT 2 5 8 OMIT 3 4 2 OMIT 2 2 0 OMIT 0 3 1 OMIT -2 5 8 OMIT 0 1 2 REM REM REM WGHT 0.059500 FVAR 8.43434 O1 4 0.269000 0.498178 0.325468 11.00000 0.01747 0.02297 = 0.02897 0.00075 0.00346 0.00059 O2 4 0.294454 0.363087 0.337814 11.00000 0.02450 0.02316 = 0.02920 0.00414 0.00011 -0.00035 O3 4 0.421919 0.408011 0.333431 11.00000 0.01983 0.02471 = 0.02030 0.00156 -0.00124 0.00320 O10 4 0.334640 0.420066 -0.108393 11.00000 0.03159 0.02346 = 0.01892 -0.00057 -0.00322 0.00651 N11 3 0.390287 0.451696 0.100928 11.00000 0.01931 0.01970 = 0.01993 -0.00215 0.00070 0.00449 H11 2 0.418895 0.390395 0.083364 11.00000 0.03186 C1 1 0.330817 0.584598 0.288118 11.00000 0.01527 0.02214 = 0.02259 -0.00354 -0.00003 0.00049 C2 1 0.400226 0.508505 0.239928 11.00000 0.01701 0.02102 = 0.02021 -0.00121 -0.00103 0.00153 AFIX 13 H2 2 0.443077 0.571029 0.233880 11.00000 -1.20000 AFIX 0 C3 1 0.361049 0.361570 0.419669 11.00000 0.02575 0.03116 = 0.02184 0.00297 -0.00016 0.00098 C4 1 0.354690 0.443461 0.552909 11.00000 0.03667 0.04617 = 0.01985 0.00047 0.00188 0.00722 AFIX 23 H4A 2 0.382806 0.399828 0.629387 11.00000 -1.20000 H4B 2 0.301179 0.447112 0.581429 11.00000 -1.20000 AFIX 0 C5 1 0.384185 0.581995 0.538133 11.00000 0.03438 0.04051 = 0.02231 -0.01202 -0.00524 0.00777 AFIX 23 H5A 2 0.439074 0.577774 0.521264 11.00000 -1.20000 H5B 2 0.376492 0.627087 0.629016 11.00000 -1.20000 AFIX 0 C6 1 0.398077 0.783954 0.387273 11.00000 0.02287 0.02660 = 0.04717 -0.01651 -0.00768 0.00424 AFIX 13 H6 2 0.448952 0.751900 0.358954 11.00000 -1.20000 AFIX 0 C7 1 0.365897 0.862018 0.264874 11.00000 0.02563 0.02145 = 0.05418 -0.00865 -0.00436 0.00178 AFIX 23 H7A 2 0.401166 0.933000 0.241217 11.00000 -1.20000 H7B 2 0.317773 0.901782 0.294577 11.00000 -1.20000 AFIX 0 C8 1 0.352293 0.779815 0.133586 11.00000 0.02204 0.02029 = 0.04000 0.00089 0.00034 0.00095 AFIX 23 H8A 2 0.400835 0.745805 0.098350 11.00000 -1.20000 H8B 2 0.329803 0.834258 0.058785 11.00000 -1.20000 AFIX 0 C9 1 0.278726 0.580588 0.040714 11.00000 0.01934 0.02085 = 0.02320 -0.00032 -0.00219 0.00336 AFIX 13 H9 2 0.232842 0.531338 0.069774 11.00000 -1.20000 AFIX 0 C10 1 0.337772 0.479477 0.005918 11.00000 0.02209 0.01590 = 0.02011 0.00182 0.00103 -0.00002 C11 1 0.348587 0.665212 0.420707 11.00000 0.02166 0.02932 = 0.02783 -0.00995 -0.00251 0.00597 AFIX 13 H11A 2 0.299645 0.698662 0.457723 11.00000 -1.20000 AFIX 0 C12 1 0.299627 0.666932 0.167184 11.00000 0.01574 0.01977 = 0.02684 -0.00182 0.00018 0.00251 AFIX 13 H12 2 0.251630 0.706004 0.201970 11.00000 -1.20000 AFIX 0 C13 1 0.376056 0.218743 0.446310 11.00000 0.03373 0.03243 = 0.03114 0.00940 -0.00095 0.00207 AFIX 137 H13A 2 0.372737 0.171010 0.357311 11.00000 -1.50000 H13B 2 0.338619 0.184892 0.512514 11.00000 -1.50000 H13C 2 0.426493 0.208169 0.486293 11.00000 -1.50000 AFIX 0 C14 1 0.407549 0.869520 0.518271 11.00000 0.03479 0.04012 = 0.06081 -0.02916 -0.01587 0.00968 AFIX 137 H14A 2 0.436669 0.946917 0.493657 11.00000 -1.50000 H14B 2 0.434089 0.820757 0.591571 11.00000 -1.50000 H14C 2 0.357938 0.895524 0.553233 11.00000 -1.50000 AFIX 0 C15 1 0.256561 0.656211 -0.091407 11.00000 0.03830 0.02727 = 0.02803 0.00158 -0.00465 0.01204 AFIX 137 H15A 2 0.217958 0.720285 -0.067341 11.00000 -1.50000 H15B 2 0.236661 0.596187 -0.162175 11.00000 -1.50000 H15C 2 0.300858 0.700624 -0.129377 11.00000 -1.50000 AFIX 0 PART -1 O20 4 0.469595 0.220766 0.022239 10.50000 0.02446 0.02715 = 0.04621 -0.01107 -0.01247 0.00943 O21 4 0.394390 0.198012 -0.172385 10.50000 0.03334 0.01984 = 0.03964 -0.00434 -0.01396 0.00759 H21 2 0.370079 0.273562 -0.138296 10.50000 0.02765 O22 4 0.398143 -0.058700 -0.154910 10.50000 0.03343 0.02532 = 0.03778 -0.00235 -0.01214 0.00219 H22 2 0.382115 -0.006331 -0.217919 10.50000 0.09186 O23 4 0.606175 -0.205048 -0.163434 10.50000 0.02953 0.02593 = 0.02725 0.00821 0.00866 0.00888 H23 2 0.618856 -0.288276 -0.140511 10.50000 0.06139 O24 4 0.537740 -0.208105 0.026485 10.50000 0.03121 0.03144 = 0.03070 0.00880 0.00832 0.00907 C21 1 0.437855 0.155366 -0.064445 10.50000 0.01519 0.02102 = 0.03085 -0.00234 -0.00122 0.00391 C22 1 0.451064 0.007667 -0.071959 10.50000 0.01963 0.02072 = 0.02134 -0.00216 -0.00041 0.00452 AFIX 13 H22A 2 0.446663 -0.026817 0.026102 10.50000 -1.20000 AFIX 0 C23 1 0.530957 -0.018742 -0.121289 10.50000 0.02305 0.02322 = 0.02522 0.00249 0.00192 0.00414 AFIX 23 H23A 2 0.533810 -0.007192 -0.224637 10.50000 -1.20000 H23B 2 0.565548 0.044498 -0.077106 10.50000 -1.20000 AFIX 0 C24 1 0.555403 -0.154242 -0.083693 10.50000 0.02215 0.02584 = 0.02591 0.00394 0.00393 0.00452 HKLF 4 REM madiha16a in P21212 #18 REM R1 = 0.0258 for 3011 Fo > 4sig(Fo) and 0.0268 for all 3094 data REM 281 parameters refined using 58 restraints END WGHT 0.0357 0.1685 REM Highest difference peak 0.179, deepest hole -0.144, 1-sigma level 0.029 Q1 1 0.3620 0.5424 0.2598 11.00000 0.05 0.18 Q2 1 0.3136 0.5357 0.0208 11.00000 0.05 0.17 Q3 1 0.3739 0.7220 0.3908 11.00000 0.05 0.16 Q4 1 0.3424 0.6271 0.3473 11.00000 0.05 0.15 Q5 1 0.3655 0.6244 0.4780 11.00000 0.05 0.13 Q6 1 0.2942 0.6194 0.1033 11.00000 0.05 0.13 Q7 1 0.3169 0.6306 0.2289 11.00000 0.05 0.13 Q8 1 0.3317 0.7187 0.1497 11.00000 0.05 0.12 Q9 1 0.3533 0.5180 0.5428 11.00000 0.05 0.12 Q10 1 0.3599 0.4037 0.4874 11.00000 0.05 0.12 Q11 1 0.3850 0.8273 0.3206 11.00000 0.05 0.12 Q12 1 0.3736 0.2817 0.4327 11.00000 0.05 0.11 Q13 1 0.5459 -0.0767 -0.1007 11.00000 0.05 0.10 Q14 1 0.4055 0.8240 0.4443 11.00000 0.05 0.10 Q15 1 0.3082 0.7049 0.4220 11.00000 0.05 0.10 Q16 1 0.3500 0.4375 0.1018 11.00000 0.05 0.09 Q17 1 0.3781 0.4082 -0.1371 11.00000 0.05 0.09 Q18 1 0.3675 0.8210 0.1944 11.00000 0.05 0.09 Q19 1 0.3624 0.9223 0.5052 11.00000 0.05 0.09 Q20 1 0.3902 0.5080 0.0295 11.00000 0.05 0.09 ; _shelx_res_checksum 59946 _olex2_date_sample_data_collection 2017-05-16 _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 1.269 _oxdiff_exptl_absorpt_empirical_full_min 0.770 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, 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 O1 O 0.26900(6) 0.49818(11) 0.32547(12) 0.0231(3) Uani 1 1 d . . . . . O2 O 0.29445(7) 0.36309(12) 0.33781(13) 0.0256(3) Uani 1 1 d . . . . . O3 O 0.42192(7) 0.40801(12) 0.33343(12) 0.0216(3) Uani 1 1 d . . . . . O10 O 0.33464(7) 0.42007(12) -0.10839(12) 0.0247(3) Uani 1 1 d . . . . . N11 N 0.39029(8) 0.45170(14) 0.10093(14) 0.0196(3) Uani 1 1 d . . . . . H11 H 0.4189(15) 0.390(3) 0.083(3) 0.032(6) Uiso 1 1 d . . . . . C1 C 0.33082(9) 0.58460(17) 0.28812(16) 0.0200(3) Uani 1 1 d . . . . . C2 C 0.40023(9) 0.50850(15) 0.23993(16) 0.0194(3) Uani 1 1 d . . . . . H2 H 0.4431 0.5710 0.2339 0.023 Uiso 1 1 calc R . . . . C3 C 0.36105(10) 0.36157(18) 0.41967(18) 0.0262(4) Uani 1 1 d . . . . . C4 C 0.35469(12) 0.4435(2) 0.55291(18) 0.0342(4) Uani 1 1 d . . . . . H4A H 0.3828 0.3998 0.6294 0.041 Uiso 1 1 calc R . . . . H4B H 0.3012 0.4471 0.5814 0.041 Uiso 1 1 calc R . . . . C5 C 0.38419(12) 0.5820(2) 0.53813(18) 0.0324(4) Uani 1 1 d . . . . . H5A H 0.4391 0.5778 0.5213 0.039 Uiso 1 1 calc R . . . . H5B H 0.3765 0.6271 0.6290 0.039 Uiso 1 1 calc R . . . . C6 C 0.39808(10) 0.78395(18) 0.3873(2) 0.0322(4) Uani 1 1 d . . . . . H6 H 0.4490 0.7519 0.3590 0.039 Uiso 1 1 calc R . . . . C7 C 0.36590(11) 0.86202(18) 0.2649(2) 0.0338(4) Uani 1 1 d . . . . . H7A H 0.4012 0.9330 0.2412 0.041 Uiso 1 1 calc R . . . . H7B H 0.3178 0.9018 0.2946 0.041 Uiso 1 1 calc R . . . . C8 C 0.35229(10) 0.77982(17) 0.1336(2) 0.0274(4) Uani 1 1 d . . . . . H8A H 0.4008 0.7458 0.0983 0.033 Uiso 1 1 calc R . . . . H8B H 0.3298 0.8343 0.0588 0.033 Uiso 1 1 calc R . . . . C9 C 0.27873(9) 0.58059(16) 0.04071(16) 0.0211(3) Uani 1 1 d . . . . . H9 H 0.2328 0.5313 0.0698 0.025 Uiso 1 1 calc R . . . . C10 C 0.33777(9) 0.47948(15) 0.00592(16) 0.0194(3) Uani 1 1 d . . . . . C11 C 0.34859(10) 0.66521(17) 0.42071(19) 0.0263(4) Uani 1 1 d . . . . . H11A H 0.2996 0.6987 0.4577 0.032 Uiso 1 1 calc R . . . . C12 C 0.29963(8) 0.66693(15) 0.16718(18) 0.0208(3) Uani 1 1 d . . . . . H12 H 0.2516 0.7060 0.2020 0.025 Uiso 1 1 calc R . . . . C13 C 0.37606(12) 0.2187(2) 0.44631(19) 0.0324(4) Uani 1 1 d . . . . . H13A H 0.3727 0.1710 0.3573 0.049 Uiso 1 1 calc GR . . . . H13B H 0.3386 0.1849 0.5125 0.049 Uiso 1 1 calc GR . . . . H13C H 0.4265 0.2082 0.4863 0.049 Uiso 1 1 calc GR . . . . C14 C 0.40755(13) 0.8695(2) 0.5183(3) 0.0452(6) Uani 1 1 d . . . . . H14A H 0.4367 0.9469 0.4937 0.068 Uiso 1 1 calc GR . . . . H14B H 0.4341 0.8208 0.5916 0.068 Uiso 1 1 calc GR . . . . H14C H 0.3579 0.8955 0.5532 0.068 Uiso 1 1 calc GR . . . . C15 C 0.25656(12) 0.65621(18) -0.09141(19) 0.0312(4) Uani 1 1 d . . . . . H15A H 0.2180 0.7203 -0.0673 0.047 Uiso 1 1 calc GR . . . . H15B H 0.2367 0.5962 -0.1622 0.047 Uiso 1 1 calc GR . . . . H15C H 0.3009 0.7006 -0.1294 0.047 Uiso 1 1 calc GR . . . . O20 O 0.4696(12) 0.2208(16) 0.022(2) 0.033(2) Uani 0.5 1 d . U P A -1 O21 O 0.3944(19) 0.198(2) -0.172(2) 0.031(4) Uani 0.5 1 d D U P A -1 H21 H 0.370(5) 0.274(7) -0.138(9) 0.03(2) Uiso 0.5 1 d D U P B -1 O22 O 0.39814(15) -0.0587(3) -0.1549(3) 0.0322(6) Uani 0.5 1 d . U P A -1 H22 H 0.382(5) -0.006(8) -0.218(9) 0.09(3) Uiso 0.5 1 d . . P C -1 O23 O 0.6062(18) -0.205(3) -0.163(2) 0.028(3) Uani 0.5 1 d D U P A -1 H23 H 0.619(6) -0.288(5) -0.141(13) 0.06(4) Uiso 0.5 1 d D U P D -1 O24 O 0.5377(12) -0.2081(16) 0.0265(19) 0.031(2) Uani 0.5 1 d . U P A -1 C21 C 0.4379(10) 0.1554(16) -0.0644(14) 0.0224(18) Uani 0.5 1 d D U P A -1 C22 C 0.4511(2) 0.0077(4) -0.0720(5) 0.0206(8) Uani 0.5 1 d D U P A -1 H22A H 0.4467 -0.0268 0.0261 0.025 Uiso 0.5 1 calc R . P A -1 C23 C 0.5310(3) -0.0187(4) -0.1213(5) 0.0238(9) Uani 0.5 1 d D U P A -1 H23A H 0.5338 -0.0072 -0.2246 0.029 Uiso 0.5 1 calc R . P A -1 H23B H 0.5655 0.0445 -0.0771 0.029 Uiso 0.5 1 calc R . P A -1 C24 C 0.5554(10) -0.1542(16) -0.0837(14) 0.025(2) Uani 0.5 1 d D U P A -1 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 0.0175(5) 0.0230(5) 0.0290(6) 0.0007(5) 0.0035(4) 0.0006(5) O2 0.0245(6) 0.0232(6) 0.0292(6) 0.0041(5) 0.0001(5) -0.0003(5) O3 0.0198(5) 0.0247(6) 0.0203(5) 0.0016(5) -0.0012(4) 0.0032(5) O10 0.0316(6) 0.0235(6) 0.0189(5) -0.0006(5) -0.0032(4) 0.0065(5) N11 0.0193(6) 0.0197(6) 0.0199(6) -0.0021(5) 0.0007(5) 0.0045(5) C1 0.0153(7) 0.0221(7) 0.0226(7) -0.0035(6) 0.0000(6) 0.0005(6) C2 0.0170(7) 0.0210(7) 0.0202(7) -0.0012(6) -0.0010(6) 0.0015(6) C3 0.0257(8) 0.0312(9) 0.0218(8) 0.0030(7) -0.0002(7) 0.0010(7) C4 0.0367(10) 0.0462(12) 0.0198(8) 0.0005(7) 0.0019(7) 0.0072(9) C5 0.0344(10) 0.0405(10) 0.0223(8) -0.0120(7) -0.0052(7) 0.0078(8) C6 0.0229(8) 0.0266(9) 0.0472(11) -0.0165(8) -0.0077(7) 0.0042(7) C7 0.0256(8) 0.0215(8) 0.0542(11) -0.0086(8) -0.0044(8) 0.0018(7) C8 0.0220(8) 0.0203(8) 0.0400(9) 0.0009(7) 0.0003(7) 0.0009(6) C9 0.0193(8) 0.0209(7) 0.0232(7) -0.0003(6) -0.0022(6) 0.0034(6) C10 0.0221(7) 0.0159(7) 0.0201(7) 0.0018(6) 0.0010(6) 0.0000(6) C11 0.0217(8) 0.0293(9) 0.0278(8) -0.0100(7) -0.0025(7) 0.0060(7) C12 0.0157(7) 0.0198(8) 0.0268(8) -0.0018(6) 0.0002(6) 0.0025(6) C13 0.0337(10) 0.0324(10) 0.0311(9) 0.0094(7) -0.0010(8) 0.0021(8) C14 0.0348(11) 0.0401(11) 0.0608(14) -0.0292(11) -0.0159(10) 0.0097(9) C15 0.0383(10) 0.0273(8) 0.0280(9) 0.0016(7) -0.0046(8) 0.0120(7) O20 0.024(3) 0.027(3) 0.046(3) -0.011(2) -0.012(3) 0.009(2) O21 0.033(6) 0.020(3) 0.040(5) -0.004(3) -0.014(5) 0.008(3) O22 0.0334(13) 0.0253(12) 0.0378(13) -0.0024(10) -0.0121(11) 0.0022(10) O23 0.030(5) 0.026(4) 0.027(3) 0.008(2) 0.009(3) 0.009(3) O24 0.031(5) 0.031(3) 0.031(2) 0.009(2) 0.008(2) 0.009(3) C21 0.015(3) 0.0210(17) 0.031(4) -0.0023(18) -0.001(3) 0.0039(14) C22 0.0196(15) 0.0207(14) 0.0213(19) -0.0022(13) -0.0004(12) 0.0045(11) C23 0.0231(16) 0.0232(16) 0.025(2) 0.0025(13) 0.0019(12) 0.0041(12) C24 0.022(4) 0.0258(18) 0.026(3) 0.004(2) 0.004(3) 0.005(2) 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 111.52(11) C3 O2 O1 108.16(12) C2 O3 C3 113.27(12) C10 N11 C2 127.88(14) O1 C1 C2 111.48(13) O1 C1 C11 106.59(13) O1 C1 C12 104.38(12) C2 C1 C11 110.80(13) C12 C1 C2 110.58(13) C12 C1 C11 112.78(14) O3 C2 N11 107.85(12) O3 C2 C1 113.98(13) N11 C2 C1 112.30(12) O2 C3 O3 108.22(13) O2 C3 C4 112.77(15) O2 C3 C13 104.42(15) O3 C3 C4 110.08(15) O3 C3 C13 106.60(15) C13 C3 C4 114.34(15) C3 C4 C5 114.59(15) C4 C5 C11 116.47(16) C7 C6 C11 111.25(15) C7 C6 C14 110.80(16) C14 C6 C11 110.66(18) C6 C7 C8 112.85(15) C7 C8 C12 110.48(15) C10 C9 C12 113.61(13) C10 C9 C15 110.53(13) C15 C9 C12 114.00(14) O10 C10 N11 121.05(15) O10 C10 C9 119.77(14) N11 C10 C9 119.12(14) C1 C11 C5 111.97(14) C6 C11 C1 112.18(15) C6 C11 C5 110.91(15) C1 C12 C9 110.55(13) C8 C12 C1 110.93(13) C8 C12 C9 115.19(14) O20 C21 O21 127.0(19) O20 C21 C22 120.9(12) O21 C21 C22 111.8(14) O22 C22 C21 113.9(6) O22 C22 C23 111.4(3) C23 C22 C21 109.5(8) C24 C23 C22 111.3(7) O23 C24 C23 116.1(14) O24 C24 O23 119.8(15) O24 C24 C23 123.3(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 O2 1.4701(17) O1 C1 1.459(2) O2 C3 1.417(2) O3 C2 1.4186(19) O3 C3 1.439(2) O10 C10 1.248(2) N11 C2 1.455(2) N11 C10 1.330(2) C1 C2 1.533(2) C1 C11 1.542(2) C1 C12 1.532(2) C3 C4 1.526(2) C3 C13 1.519(3) C4 C5 1.529(3) C5 C11 1.543(3) C6 C7 1.526(3) C6 C11 1.541(3) C6 C14 1.535(3) C7 C8 1.527(3) C8 C12 1.528(2) C9 C10 1.516(2) C9 C12 1.541(2) C9 C15 1.529(2) O20 C21 1.205(17) O21 C21 1.36(2) O22 C22 1.405(5) O23 C24 1.29(3) O24 C24 1.226(16) C21 C22 1.544(14) C22 C23 1.520(6) C23 C24 1.507(12) 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) 2.05(3) 2.868(18) 168(2) . N11 H11 O24 0.83(3) 2.10(3) 2.908(18) 164(2) 2_655 O21 H21 O10 0.95(5) 1.66(5) 2.60(2) 168(9) . O23 H23 O10 0.91(3) 1.62(5) 2.51(3) 164(11) 2_655 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 -75.44(15) O1 O2 C3 C4 46.57(17) O1 O2 C3 C13 171.29(12) O1 C1 C2 O3 -50.33(17) O1 C1 C2 N11 72.70(16) O1 C1 C11 C5 69.35(18) O1 C1 C11 C6 -165.20(13) O1 C1 C12 C8 169.43(13) O1 C1 C12 C9 -61.51(15) O2 O1 C1 C2 12.83(15) O2 O1 C1 C11 -108.20(13) O2 O1 C1 C12 132.23(12) O2 C3 C4 C5 -94.44(19) O3 C3 C4 C5 26.5(2) C1 O1 O2 C3 46.91(15) C2 O3 C3 O2 36.40(18) C2 O3 C3 C4 -87.25(16) C2 O3 C3 C13 148.22(13) C2 N11 C10 O10 -177.92(15) C2 N11 C10 C9 -0.9(2) C2 C1 C11 C5 -52.11(19) C2 C1 C11 C6 73.34(17) C2 C1 C12 C8 -70.56(17) C2 C1 C12 C9 58.49(17) C3 O3 C2 N11 -101.19(15) C3 O3 C2 C1 24.23(18) C3 C4 C5 C11 56.7(2) C4 C5 C11 C1 -36.6(2) C4 C5 C11 C6 -162.76(15) C6 C7 C8 C12 57.2(2) C7 C6 C11 C1 50.31(19) C7 C6 C11 C5 176.34(15) C7 C8 C12 C1 -56.23(18) C7 C8 C12 C9 177.24(14) C10 N11 C2 O3 141.14(16) C10 N11 C2 C1 14.7(2) C10 C9 C12 C1 -44.76(18) C10 C9 C12 C8 81.96(17) C11 C1 C2 O3 68.21(17) C11 C1 C2 N11 -168.76(14) C11 C1 C12 C8 54.14(18) C11 C1 C12 C9 -176.81(13) C11 C6 C7 C8 -54.0(2) C12 C1 C2 O3 -165.97(13) C12 C1 C2 N11 -42.95(17) C12 C1 C11 C5 -176.69(14) C12 C1 C11 C6 -51.24(18) C12 C9 C10 O10 -166.67(14) C12 C9 C10 N11 16.2(2) C13 C3 C4 C5 146.46(17) C14 C6 C7 C8 -177.59(17) C14 C6 C11 C1 173.94(15) C14 C6 C11 C5 -60.03(19) C15 C9 C10 O10 -37.1(2) C15 C9 C10 N11 145.85(16) C15 C9 C12 C1 -172.61(14) C15 C9 C12 C8 -45.89(19) O20 C21 C22 O22 166.1(18) O20 C21 C22 C23 -68(2) O21 C21 C22 O22 -20(2) O21 C21 C22 C23 105(2) O22 C22 C23 C24 -72.6(8) C21 C22 C23 C24 160.4(8) C22 C23 C24 O23 153(2) C22 C23 C24 O24 -37(2)