#------------------------------------------------------------------------------ #$Date: 2019-11-17 09:21:57 +0200 (Sun, 17 Nov 2019) $ #$Revision: 229075 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229943.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_7229943 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 'C15 H23 N O4, C8 H8 O3' _chemical_formula_sum 'C23 H31 N O7' _chemical_formula_weight 433.49 _chemical_name_common 11-Aza:D-Man _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 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 4 _cell_length_a 10.00907(10) _cell_length_b 10.09992(10) _cell_length_c 20.9254(2) _cell_measurement_reflns_used 9723 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 75.5490 _cell_measurement_theta_min 4.2190 _cell_volume 2115.37(4) _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 0.979 _diffrn_measured_fraction_theta_max 0.979 _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 40.00 130.00 1.00 3.00 -- 110.57 -45.00-150.00 90 2 \w 21.00 48.00 1.00 1.00 -- 40.57 -99.00 0.00 27 3 \w 88.00 178.00 1.00 3.00 -- 110.57 45.00 30.00 90 4 \w 93.00 178.00 1.00 3.00 -- 110.57 45.00 150.00 85 5 \w 97.00 178.00 1.00 3.00 -- 110.57 125.00 -30.00 81 6 \w -94.00 -5.00 1.00 1.00 -- -40.57 125.00-120.00 89 7 \w -104.00 -17.00 1.00 1.00 -- -40.57 -37.00 30.00 87 8 \w -67.00 36.00 1.00 1.00 -- -40.57 37.00-150.00 103 9 \w 96.00 178.00 1.00 3.00 -- 110.57 82.00 -96.00 82 10 \w 57.00 144.00 1.00 3.00 -- 110.57 -77.00 -60.00 87 11 \w 32.00 84.00 1.00 3.00 -- 110.57-111.00-150.00 52 12 \w 104.00 147.00 1.00 3.00 -- 110.57 111.00-150.00 43 13 \w 47.00 115.00 1.00 3.00 -- 110.57-111.00 -90.00 68 14 \w 33.00 112.00 1.00 3.00 -- 110.57-111.00 120.00 79 ; _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 -0.0917488000 _diffrn_orient_matrix_UB_12 -0.0045249000 _diffrn_orient_matrix_UB_13 0.0590989000 _diffrn_orient_matrix_UB_21 0.0749120000 _diffrn_orient_matrix_UB_22 -0.1233285000 _diffrn_orient_matrix_UB_23 0.0243883000 _diffrn_orient_matrix_UB_31 0.0983599000 _diffrn_orient_matrix_UB_32 0.0895369000 _diffrn_orient_matrix_UB_33 0.0365218000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_unetI/netI 0.0189 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 12213 _diffrn_reflns_point_group_measured_fraction_full 0.981 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.500 _diffrn_reflns_theta_min 4.226 _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 0.830 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71696 _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_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.176 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.029 _refine_ls_abs_structure_details ; Flack x determined using 1564 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.03(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 3723 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.000 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0227 _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^)+(0.0360P)^2^+0.2670P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.0576 _reflns_Friedel_coverage 0.746 _reflns_Friedel_fraction_full 0.985 _reflns_Friedel_fraction_max 0.983 _reflns_number_gt 3677 _reflns_number_total 3723 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block cpd4_madiha27cult _cod_depositor_comments 'Adding full bibliography for 7229939--7229946.cif.' _cod_database_code 7229943 _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 99.96 _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, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12), C22(H22A) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B) 2.c Aromatic/amide H refined with riding coordinates: C24(H24), C25(H25), C26(H26), C27(H27), C28(H28) 2.d Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) ; _shelx_res_file ; madiha27cult.res created by SHELXL-2014/7 TITL madiha27CuLT in P212121 #19 REM reset to P212121 #19 CELL 1.54184 10.00907 10.09992 20.92544 90 90 90 ZERR 4 0.0001 0.0001 0.00023 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 92 124 4 28 EQIV $1 -X,0.5+Y,0.5-Z L.S. 6 PLAN 20 TEMP -173 HTAB O22 O10 HTAB N11 O20 HTAB O21 O22_$1 HTAB CONF BOND fmap 2 acta 133 OMIT 0 135 OMIT 0 5 7 OMIT 0 2 24 OMIT 4 0 4 OMIT 2 9 2 OMIT 3 0 11 OMIT 1 1 11 OMIT 0 0 8 OMIT 1 9 5 OMIT -1 1 4 OMIT 2 9 0 OMIT 6 0 5 OMIT 2 9 4 OMIT 0 5 4 OMIT -4 3 22 OMIT 2 3 0 OMIT 7 5 0 OMIT 3 3 3 OMIT -3 3 3 OMIT -1 9 5 OMIT 0 8 6 OMIT 8 6 0 OMIT 5 10 5 OMIT -2 9 4 OMIT 1 0 2 OMIT -6 10 1 OMIT 5 2 0 OMIT 1 0 13 OMIT 0 3 3 OMIT 4 2 20 OMIT 4 11 5 OMIT 0 3 4 OMIT 6 10 1 OMIT 5 2 21 OMIT 1 10 0 OMIT 1 1 4 OMIT 0 0 4 OMIT 3 0 1 OMIT 1 0 6 OMIT 0 5 1 OMIT 0 4 0 OMIT 1 0 5 OMIT 0 1 3 OMIT 2 10 5 OMIT 10 4 0 OMIT 2 3 11 OMIT 4 2 2 OMIT -7 4 13 OMIT -7 5 1 OMIT 0 3 1 OMIT -2 10 3 OMIT -1 1 11 OMIT -4 2 20 OMIT 2 10 3 OMIT -6 4 6 OMIT -2 10 5 OMIT 0 5 3 OMIT 0 5 6 OMIT -4 11 5 OMIT 7 3 3 OMIT 4 3 8 OMIT -4 3 8 OMIT 0 1 13 OMIT 4 3 1 OMIT -7 3 3 OMIT 3 1 11 OMIT -4 2 2 OMIT 6 4 6 OMIT -4 3 1 REM REM REM WGHT 0.036000 0.267000 FVAR 5.37166 O1 4 0.317566 0.690465 0.050581 11.00000 0.01077 0.02060 = 0.01646 -0.00074 0.00121 -0.00142 O2 4 0.174008 0.661205 0.057670 11.00000 0.01073 0.02003 = 0.02132 -0.00271 -0.00029 -0.00159 O3 4 0.159076 0.731105 0.162236 11.00000 0.01105 0.01725 = 0.01757 0.00090 0.00043 0.00260 O10 4 0.343947 0.330178 0.163165 11.00000 0.01785 0.01127 = 0.03295 0.00196 0.00359 -0.00027 N11 3 0.289729 0.542682 0.178430 11.00000 0.01310 0.01243 = 0.01864 0.00294 0.00371 -0.00032 H11 2 0.232106 0.516234 0.205848 11.00000 -1.20000 C1 1 0.381996 0.722537 0.111423 11.00000 0.01230 0.01160 = 0.01513 -0.00001 -0.00075 0.00021 C2 1 0.292997 0.685025 0.167869 11.00000 0.01128 0.01195 = 0.01737 0.00038 -0.00014 0.00122 AFIX 13 H2 2 0.332195 0.726629 0.206971 11.00000 -1.20000 AFIX 0 C3 1 0.118106 0.759713 0.097968 11.00000 0.01418 0.01817 = 0.01878 -0.00092 -0.00140 0.00384 C4 1 0.160404 0.899825 0.078439 11.00000 0.01640 0.01612 = 0.02438 0.00394 -0.00330 0.00542 AFIX 23 H4A 2 0.083665 0.960292 0.084702 11.00000 -1.20000 H4B 2 0.182379 0.899680 0.032310 11.00000 -1.20000 AFIX 0 C5 1 0.280497 0.954284 0.115530 11.00000 0.01636 0.01147 = 0.02564 0.00209 0.00030 0.00131 AFIX 23 H5A 2 0.255052 0.961877 0.161102 11.00000 -1.20000 H5B 2 0.299578 1.044752 0.099771 11.00000 -1.20000 AFIX 0 C6 1 0.509493 0.913038 0.164274 11.00000 0.01507 0.01291 = 0.01973 -0.00061 0.00004 -0.00066 AFIX 13 H6 2 0.464942 0.899399 0.206538 11.00000 -1.20000 AFIX 0 C7 1 0.634398 0.826505 0.162284 11.00000 0.01516 0.01542 = 0.02489 -0.00003 -0.00461 -0.00062 AFIX 23 H7A 2 0.683478 0.844133 0.122099 11.00000 -1.20000 H7B 2 0.693526 0.850852 0.198344 11.00000 -1.20000 AFIX 0 C8 1 0.602361 0.679552 0.166267 11.00000 0.01491 0.01459 = 0.02522 0.00123 -0.00249 0.00179 AFIX 23 H8A 2 0.558211 0.660051 0.207544 11.00000 -1.20000 H8B 2 0.686129 0.627615 0.164155 11.00000 -1.20000 AFIX 0 C9 1 0.476961 0.490981 0.106888 11.00000 0.01435 0.01237 = 0.02233 -0.00133 0.00238 0.00078 AFIX 13 H9 2 0.442287 0.475717 0.062679 11.00000 -1.20000 AFIX 0 C10 1 0.366226 0.448135 0.151974 11.00000 0.01362 0.01360 = 0.02055 0.00150 -0.00180 0.00019 C11 1 0.409968 0.872463 0.111278 11.00000 0.01318 0.01301 = 0.01693 0.00186 0.00115 -0.00010 AFIX 13 H11A 2 0.452822 0.894087 0.069390 11.00000 -1.20000 AFIX 0 C12 1 0.510128 0.639411 0.111044 11.00000 0.01194 0.01167 = 0.01856 0.00040 0.00213 -0.00013 AFIX 13 H12 2 0.558528 0.662355 0.070731 11.00000 -1.20000 AFIX 0 C13 1 -0.031571 0.737354 0.095418 11.00000 0.01371 0.02292 = 0.02776 -0.00052 -0.00236 0.00200 AFIX 137 H13A 2 -0.050722 0.643080 0.101660 11.00000 -1.50000 H13B 2 -0.065791 0.765617 0.053713 11.00000 -1.50000 H13C 2 -0.074956 0.788910 0.129233 11.00000 -1.50000 AFIX 0 C14 1 0.547368 1.058919 0.158773 11.00000 0.01895 0.01487 = 0.02478 -0.00122 0.00094 -0.00254 AFIX 137 H14A 2 0.583558 1.076272 0.116070 11.00000 -1.50000 H14B 2 0.614956 1.080400 0.191032 11.00000 -1.50000 H14C 2 0.467917 1.113788 0.165683 11.00000 -1.50000 AFIX 0 C15 1 0.599880 0.402462 0.113852 11.00000 0.01633 0.01174 = 0.03913 0.00075 0.00505 0.00205 AFIX 137 H15A 2 0.632868 0.407051 0.157891 11.00000 -1.50000 H15B 2 0.669850 0.432709 0.084525 11.00000 -1.50000 H15C 2 0.575767 0.310847 0.103607 11.00000 -1.50000 AFIX 0 O20 4 0.082299 0.455530 0.263129 11.00000 0.01392 0.01482 = 0.02002 -0.00116 -0.00025 -0.00137 O21 4 -0.128126 0.458934 0.227457 11.00000 0.01485 0.01281 = 0.02380 -0.00371 -0.00251 0.00299 H21 2 -0.127590 0.531911 0.246176 11.00000 -1.50000 O22 4 0.123963 0.204650 0.219682 11.00000 0.01185 0.01256 = 0.02188 0.00282 0.00065 0.00067 H22 2 0.180775 0.243810 0.203236 11.00000 -1.50000 C21 1 -0.010257 0.402676 0.235279 11.00000 0.01410 0.01093 = 0.01423 0.00215 0.00218 -0.00076 C22 1 -0.001693 0.264351 0.205679 11.00000 0.01232 0.01015 = 0.01964 0.00085 0.00080 0.00112 AFIX 13 H22A 2 -0.071630 0.209087 0.226968 11.00000 -1.20000 AFIX 0 C23 1 -0.034207 0.265781 0.134976 11.00000 0.01331 0.01272 = 0.01849 -0.00063 0.00094 0.00379 C24 1 0.018044 0.361934 0.094285 11.00000 0.02182 0.01661 = 0.02184 0.00038 0.00044 -0.00024 AFIX 43 H24 2 0.076472 0.427769 0.110726 11.00000 -1.20000 AFIX 0 C25 1 -0.014808 0.361995 0.029945 11.00000 0.03011 0.01918 = 0.01987 0.00386 0.00250 0.00352 AFIX 43 H25 2 0.020558 0.428339 0.002567 11.00000 -1.20000 AFIX 0 C26 1 -0.099231 0.265469 0.005302 11.00000 0.02853 0.02335 = 0.01916 -0.00247 -0.00346 0.00902 AFIX 43 H26 2 -0.122391 0.266199 -0.038723 11.00000 -1.20000 AFIX 0 C27 1 -0.149544 0.167955 0.045382 11.00000 0.02044 0.02001 = 0.02517 -0.00538 -0.00396 0.00237 AFIX 43 H27 2 -0.206439 0.101125 0.028649 11.00000 -1.20000 AFIX 0 C28 1 -0.116842 0.167876 0.109987 11.00000 0.01652 0.01436 = 0.02224 -0.00083 0.00049 0.00073 AFIX 43 H28 2 -0.151102 0.100638 0.137177 11.00000 -1.20000 AFIX 0 HKLF 4 REM madiha27CuLT in P212121 #19 REM R1 = 0.0227 for 3677 Fo > 4sig(Fo) and 0.0231 for all 3723 data REM 292 parameters refined using 0 restraints END WGHT 0.0345 0.2440 REM Instructions for potential hydrogen bonds HTAB N11 O20 EQIV $2 x-1/2, -y+3/2, -z HTAB C13 O1_$2 HTAB O21 O22_$1 HTAB O22 O10 EQIV $3 -x, y-1/2, -z+1/2 HTAB C22 O3_$3 HTAB C22 O20_$3 REM Highest difference peak 0.176, deepest hole -0.152, 1-sigma level 0.029 Q1 1 -0.0045 0.3347 0.2172 11.00000 0.05 0.18 Q2 1 0.4459 0.6817 0.1157 11.00000 0.05 0.17 Q3 1 0.4906 0.5639 0.1114 11.00000 0.05 0.15 Q4 1 0.5171 0.9924 0.1642 11.00000 0.05 0.15 Q5 1 0.4014 0.7989 0.1121 11.00000 0.05 0.14 Q6 1 0.4702 0.8977 0.1351 11.00000 0.05 0.12 Q7 1 0.5633 0.8753 0.1589 11.00000 0.05 0.12 Q8 1 0.2817 0.7351 0.2654 11.00000 0.05 0.12 Q9 1 0.3313 0.7063 0.1358 11.00000 0.05 0.12 Q10 1 0.3019 0.6104 0.1703 11.00000 0.05 0.12 Q11 1 0.3418 0.9145 0.1102 11.00000 0.05 0.11 Q12 1 -0.0806 0.3302 0.0218 11.00000 0.05 0.11 Q13 1 0.6126 0.7567 0.1654 11.00000 0.05 0.11 Q14 1 0.4218 0.4768 0.1299 11.00000 0.05 0.11 Q15 1 0.1458 0.8344 0.0840 11.00000 0.05 0.11 Q16 1 -0.0196 0.3231 0.1178 11.00000 0.05 0.11 Q17 1 0.0838 0.5419 0.2644 11.00000 0.05 0.10 Q18 1 0.5561 0.6689 0.1354 11.00000 0.05 0.10 Q19 1 -0.0168 0.3607 0.0672 11.00000 0.05 0.10 Q20 1 0.5329 0.4464 0.1180 11.00000 0.05 0.10 ; _shelx_res_checksum 1233 _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 1.303 _oxdiff_exptl_absorpt_empirical_full_min 0.712 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 O1 O 0.31757(10) 0.69046(11) 0.05058(5) 0.0159(2) Uani 1 1 d . O2 O 0.17401(11) 0.66120(11) 0.05767(5) 0.0174(2) Uani 1 1 d . O3 O 0.15908(10) 0.73110(10) 0.16224(5) 0.0153(2) Uani 1 1 d . O10 O 0.34395(11) 0.33018(10) 0.16316(6) 0.0207(2) Uani 1 1 d . N11 N 0.28973(12) 0.54268(13) 0.17843(6) 0.0147(3) Uani 1 1 d . H11 H 0.232(2) 0.516(2) 0.2058(9) 0.018 Uiso 1 1 d R C1 C 0.38200(14) 0.72254(14) 0.11142(7) 0.0130(3) Uani 1 1 d . C2 C 0.29300(14) 0.68502(14) 0.16787(7) 0.0135(3) Uani 1 1 d . H2 H 0.3322 0.7266 0.2070 0.016 Uiso 1 1 calc R C3 C 0.11811(15) 0.75971(16) 0.09797(7) 0.0170(3) Uani 1 1 d . C4 C 0.16040(15) 0.89982(16) 0.07844(8) 0.0190(3) Uani 1 1 d . H4A H 0.0837 0.9603 0.0847 0.023 Uiso 1 1 calc R H4B H 0.1824 0.8997 0.0323 0.023 Uiso 1 1 calc R C5 C 0.28050(15) 0.95428(15) 0.11553(8) 0.0178(3) Uani 1 1 d . H5A H 0.2551 0.9619 0.1611 0.021 Uiso 1 1 calc R H5B H 0.2996 1.0448 0.0998 0.021 Uiso 1 1 calc R C6 C 0.50949(15) 0.91304(15) 0.16427(7) 0.0159(3) Uani 1 1 d . H6 H 0.4649 0.8994 0.2065 0.019 Uiso 1 1 calc R C7 C 0.63440(16) 0.82650(15) 0.16228(8) 0.0185(3) Uani 1 1 d . H7A H 0.6835 0.8441 0.1221 0.022 Uiso 1 1 calc R H7B H 0.6935 0.8509 0.1983 0.022 Uiso 1 1 calc R C8 C 0.60236(15) 0.67955(15) 0.16627(8) 0.0182(3) Uani 1 1 d . H8A H 0.5582 0.6601 0.2075 0.022 Uiso 1 1 calc R H8B H 0.6861 0.6276 0.1642 0.022 Uiso 1 1 calc R C9 C 0.47696(15) 0.49098(14) 0.10689(8) 0.0164(3) Uani 1 1 d . H9 H 0.4423 0.4757 0.0627 0.020 Uiso 1 1 calc R C10 C 0.36623(15) 0.44813(15) 0.15197(7) 0.0159(3) Uani 1 1 d . C11 C 0.40997(14) 0.87246(14) 0.11128(7) 0.0144(3) Uani 1 1 d . H11A H 0.4528 0.8941 0.0694 0.017 Uiso 1 1 calc R C12 C 0.51013(14) 0.63941(14) 0.11104(7) 0.0141(3) Uani 1 1 d . H12 H 0.5585 0.6624 0.0707 0.017 Uiso 1 1 calc R C13 C -0.03157(15) 0.73735(17) 0.09542(8) 0.0215(3) Uani 1 1 d . H13A H -0.0507 0.6431 0.1017 0.032 Uiso 1 1 calc GR H13B H -0.0658 0.7656 0.0537 0.032 Uiso 1 1 calc GR H13C H -0.0750 0.7889 0.1292 0.032 Uiso 1 1 calc GR C14 C 0.54737(16) 1.05892(15) 0.15877(8) 0.0195(3) Uani 1 1 d . H14A H 0.5836 1.0763 0.1161 0.029 Uiso 1 1 calc GR H14B H 0.6150 1.0804 0.1910 0.029 Uiso 1 1 calc GR H14C H 0.4679 1.1138 0.1657 0.029 Uiso 1 1 calc GR C15 C 0.59988(16) 0.40246(16) 0.11385(9) 0.0224(3) Uani 1 1 d . H15A H 0.6329 0.4071 0.1579 0.034 Uiso 1 1 calc GR H15B H 0.6698 0.4327 0.0845 0.034 Uiso 1 1 calc GR H15C H 0.5758 0.3108 0.1036 0.034 Uiso 1 1 calc GR O20 O 0.08230(10) 0.45553(11) 0.26313(5) 0.0163(2) Uani 1 1 d . O21 O -0.12813(11) 0.45893(11) 0.22746(5) 0.0172(2) Uani 1 1 d . H21 H -0.128(2) 0.532(2) 0.2462(10) 0.026 Uiso 1 1 d R O22 O 0.12396(11) 0.20465(10) 0.21968(5) 0.0154(2) Uani 1 1 d . H22 H 0.181(2) 0.244(2) 0.2032(10) 0.023 Uiso 1 1 d R C21 C -0.01026(14) 0.40268(15) 0.23528(6) 0.0131(3) Uani 1 1 d . C22 C -0.00169(14) 0.26435(14) 0.20568(7) 0.0140(3) Uani 1 1 d . H22A H -0.0716 0.2091 0.2270 0.017 Uiso 1 1 calc R C23 C -0.03421(14) 0.26578(14) 0.13498(7) 0.0148(3) Uani 1 1 d . C24 C 0.01804(17) 0.36193(16) 0.09428(8) 0.0201(3) Uani 1 1 d . H24 H 0.0765 0.4278 0.1107 0.024 Uiso 1 1 calc R C25 C -0.01481(18) 0.36199(16) 0.02994(8) 0.0231(3) Uani 1 1 d . H25 H 0.0206 0.4283 0.0026 0.028 Uiso 1 1 calc R C26 C -0.09923(17) 0.26547(18) 0.00530(8) 0.0237(4) Uani 1 1 d . H26 H -0.1224 0.2662 -0.0387 0.028 Uiso 1 1 calc R C27 C -0.14954(17) 0.16796(16) 0.04538(8) 0.0219(3) Uani 1 1 d . H27 H -0.2064 0.1011 0.0286 0.026 Uiso 1 1 calc R C28 C -0.11684(15) 0.16788(15) 0.10999(8) 0.0177(3) Uani 1 1 d . H28 H -0.1511 0.1006 0.1372 0.021 Uiso 1 1 calc 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 O1 0.0108(5) 0.0206(5) 0.0165(5) -0.0007(4) 0.0012(4) -0.0014(4) O2 0.0107(5) 0.0200(5) 0.0213(5) -0.0027(4) -0.0003(4) -0.0016(4) O3 0.0111(5) 0.0172(5) 0.0176(5) 0.0009(4) 0.0004(4) 0.0026(4) O10 0.0179(5) 0.0113(5) 0.0330(6) 0.0020(4) 0.0036(5) -0.0003(4) N11 0.0131(6) 0.0124(6) 0.0186(6) 0.0029(5) 0.0037(5) -0.0003(5) C1 0.0123(7) 0.0116(7) 0.0151(7) 0.0000(5) -0.0008(6) 0.0002(5) C2 0.0113(7) 0.0120(7) 0.0174(7) 0.0004(6) -0.0001(6) 0.0012(5) C3 0.0142(7) 0.0182(8) 0.0188(7) -0.0009(6) -0.0014(6) 0.0038(6) C4 0.0164(7) 0.0161(7) 0.0244(7) 0.0039(6) -0.0033(6) 0.0054(6) C5 0.0164(7) 0.0115(6) 0.0256(8) 0.0021(6) 0.0003(6) 0.0013(6) C6 0.0151(7) 0.0129(6) 0.0197(7) -0.0006(6) 0.0000(6) -0.0007(5) C7 0.0152(7) 0.0154(7) 0.0249(7) 0.0000(6) -0.0046(6) -0.0006(6) C8 0.0149(7) 0.0146(7) 0.0252(8) 0.0012(6) -0.0025(6) 0.0018(5) C9 0.0144(7) 0.0124(7) 0.0223(7) -0.0013(6) 0.0024(6) 0.0008(5) C10 0.0136(7) 0.0136(7) 0.0206(7) 0.0015(6) -0.0018(6) 0.0002(5) C11 0.0132(7) 0.0130(7) 0.0169(7) 0.0019(6) 0.0011(5) -0.0001(5) C12 0.0119(6) 0.0117(7) 0.0186(7) 0.0004(5) 0.0021(6) -0.0001(5) C13 0.0137(8) 0.0229(8) 0.0278(8) -0.0005(6) -0.0024(6) 0.0020(6) C14 0.0189(7) 0.0149(7) 0.0248(8) -0.0012(6) 0.0009(6) -0.0025(6) C15 0.0163(7) 0.0117(7) 0.0391(9) 0.0007(7) 0.0051(6) 0.0020(6) O20 0.0139(5) 0.0148(5) 0.0200(5) -0.0012(4) -0.0003(4) -0.0014(4) O21 0.0149(5) 0.0128(5) 0.0238(5) -0.0037(4) -0.0025(4) 0.0030(4) O22 0.0118(5) 0.0126(5) 0.0219(5) 0.0028(4) 0.0007(4) 0.0007(4) C21 0.0141(7) 0.0109(6) 0.0142(7) 0.0022(5) 0.0022(5) -0.0008(6) C22 0.0123(7) 0.0102(6) 0.0196(7) 0.0009(5) 0.0008(6) 0.0011(5) C23 0.0133(6) 0.0127(7) 0.0185(7) -0.0006(6) 0.0009(5) 0.0038(6) C24 0.0218(8) 0.0166(7) 0.0218(8) 0.0004(6) 0.0004(6) -0.0002(6) C25 0.0301(9) 0.0192(7) 0.0199(8) 0.0039(6) 0.0025(6) 0.0035(7) C26 0.0285(9) 0.0234(9) 0.0192(7) -0.0025(6) -0.0035(6) 0.0090(7) C27 0.0204(8) 0.0200(8) 0.0252(8) -0.0054(6) -0.0040(7) 0.0024(6) C28 0.0165(7) 0.0144(7) 0.0222(7) -0.0008(6) 0.0005(6) 0.0007(6) 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 112.72(10) C3 O2 O1 107.67(10) C2 O3 C3 114.35(11) C10 N11 C2 128.83(13) O1 C1 C2 111.16(11) O1 C1 C11 107.22(11) O1 C1 C12 104.06(11) C2 C1 C11 110.58(12) C2 C1 C12 110.86(12) C12 C1 C11 112.73(12) O3 C2 N11 108.33(12) O3 C2 C1 113.83(12) N11 C2 C1 112.07(12) O2 C3 O3 107.64(11) O2 C3 C4 112.33(13) O2 C3 C13 105.32(12) O3 C3 C4 110.90(12) O3 C3 C13 106.58(12) C13 C3 C4 113.65(13) C3 C4 C5 114.39(13) C4 C5 C11 115.99(13) C7 C6 C11 110.89(12) C14 C6 C7 110.33(12) C14 C6 C11 111.22(12) C8 C7 C6 112.63(13) C7 C8 C12 110.10(12) C10 C9 C12 113.59(12) C10 C9 C15 111.21(13) C15 C9 C12 113.03(13) O10 C10 N11 120.32(14) O10 C10 C9 121.65(14) N11 C10 C9 118.00(13) C1 C11 C6 112.11(12) C5 C11 C1 112.00(12) C5 C11 C6 111.02(12) C1 C12 C8 110.79(12) C1 C12 C9 110.71(12) C8 C12 C9 115.48(13) O20 C21 O21 123.42(14) O20 C21 C22 123.45(13) O21 C21 C22 113.13(12) O22 C22 C21 110.63(11) O22 C22 C23 113.23(12) C23 C22 C21 111.99(12) C24 C23 C22 121.52(14) C28 C23 C22 119.21(14) C28 C23 C24 119.26(14) C25 C24 C23 120.32(15) C24 C25 C26 120.30(16) C27 C26 C25 119.62(15) C26 C27 C28 120.15(15) C27 C28 C23 120.32(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 O2 1.4744(14) O1 C1 1.4635(18) O2 C3 1.4192(19) O3 C2 1.4238(18) O3 C3 1.4354(18) O10 C10 1.234(2) N11 C2 1.4549(19) N11 C10 1.343(2) C1 C2 1.527(2) C1 C11 1.5399(19) C1 C12 1.533(2) C3 C4 1.533(2) C3 C13 1.516(2) C4 C5 1.533(2) C5 C11 1.540(2) C6 C7 1.526(2) C6 C11 1.546(2) C6 C14 1.526(2) C7 C8 1.521(2) C8 C12 1.534(2) C9 C10 1.518(2) C9 C12 1.538(2) C9 C15 1.528(2) O20 C21 1.2177(19) O21 C21 1.3197(18) O22 C22 1.4252(17) C21 C22 1.531(2) C22 C23 1.515(2) C23 C24 1.393(2) C23 C28 1.391(2) C24 C25 1.386(2) C25 C26 1.389(3) C26 C27 1.388(3) C27 C28 1.391(2) 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 0.86(2) 2.02(2) 2.8682(17) 174.1(18) . O21 H21 O22 0.83(2) 1.89(2) 2.7174(16) 174(2) 4 O22 H22 O10 0.77(2) 2.03(2) 2.8025(16) 174(2) . 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 -74.95(13) O1 O2 C3 C4 47.41(14) O1 O2 C3 C13 171.62(11) O1 C1 C2 O3 -48.94(15) O1 C1 C2 N11 74.42(15) O1 C1 C11 C5 69.32(15) O1 C1 C11 C6 -165.11(11) O1 C1 C12 C8 169.98(11) O1 C1 C12 C9 -60.56(14) O2 O1 C1 C2 13.80(15) O2 O1 C1 C11 -107.17(12) O2 O1 C1 C12 133.18(11) O2 C3 C4 C5 -95.88(15) O3 C3 C4 C5 24.61(18) C1 O1 O2 C3 45.54(14) C2 O3 C3 O2 38.86(15) C2 O3 C3 C4 -84.38(14) C2 O3 C3 C13 151.44(12) C2 N11 C10 O10 -175.07(15) C2 N11 C10 C9 3.2(2) C2 C1 C11 C5 -52.01(16) C2 C1 C11 C6 73.56(15) C2 C1 C12 C8 -70.44(15) C2 C1 C12 C9 59.02(16) C3 O3 C2 N11 -103.72(13) C3 O3 C2 C1 21.66(16) C3 C4 C5 C11 58.43(18) C4 C5 C11 C1 -37.79(18) C4 C5 C11 C6 -163.96(12) C6 C7 C8 C12 58.46(17) C7 C6 C11 C1 50.69(16) C7 C6 C11 C5 176.80(12) C7 C8 C12 C1 -56.87(16) C7 C8 C12 C9 176.26(13) C10 N11 C2 O3 136.64(15) C10 N11 C2 C1 10.2(2) C10 C9 C12 C1 -45.64(17) C10 C9 C12 C8 81.27(16) C11 C1 C2 O3 70.03(15) C11 C1 C2 N11 -166.60(12) C11 C1 C12 C8 54.14(16) C11 C1 C12 C9 -176.40(12) C11 C6 C7 C8 -55.18(17) C12 C1 C2 O3 -164.17(11) C12 C1 C2 N11 -40.81(16) C12 C1 C11 C5 -176.75(12) C12 C1 C11 C6 -51.18(16) C12 C9 C10 O10 -166.64(14) C12 C9 C10 N11 15.1(2) C13 C3 C4 C5 144.66(14) C14 C6 C7 C8 -178.86(13) C14 C6 C11 C1 173.86(12) C14 C6 C11 C5 -60.03(16) C15 C9 C10 O10 -37.8(2) C15 C9 C10 N11 143.98(14) C15 C9 C12 C1 -173.56(13) C15 C9 C12 C8 -46.66(18) O20 C21 C22 O22 4.44(19) O20 C21 C22 C23 -122.90(15) O21 C21 C22 O22 -175.66(11) O21 C21 C22 C23 57.00(16) O22 C22 C23 C24 -81.42(17) O22 C22 C23 C28 97.79(16) C21 C22 C23 C24 44.52(19) C21 C22 C23 C28 -136.27(14) C22 C23 C24 C25 -179.11(14) C22 C23 C28 C27 179.20(14) C23 C24 C25 C26 -0.6(3) C24 C23 C28 C27 -1.6(2) C24 C25 C26 C27 -0.7(3) C25 C26 C27 C28 0.8(2) C26 C27 C28 C23 0.4(2) C28 C23 C24 C25 1.7(2)