#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105117.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2105117 loop_ _publ_author_name 'Zakharov, Boris A.' 'Losev, Evgeniy A.' 'Kolesov, Boris A.' 'Drebushchak, Valeri A.' 'Boldyreva, Elena V.' _publ_section_title ; Low-temperature phase transition in glycine--glutaric acid co-crystals studied by single-crystal X-ray diffraction, Raman spectroscopy and differential scanning calorimetry ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 287 _journal_page_last 296 _journal_paper_doi 10.1107/S0108768112015972 _journal_volume 68 _journal_year 2012 _chemical_formula_moiety 'C5 H8 O4, C2 H5 N O2' _chemical_formula_sum 'C7 H13 N O6' _chemical_formula_weight 207.18 _chemical_name_common 'glutaric acid--glycine (1/1)' _chemical_name_systematic ; Propane-1,3-dicarboxylic acid -- Aminoethanoic acid (1/1) ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 85.578(14) _cell_angle_beta 113.133(11) _cell_angle_gamma 88.301(13) _cell_formula_units_Z 4 _cell_length_a 4.9155(7) _cell_length_b 20.215(3) _cell_length_c 10.1862(16) _cell_measurement_reflns_used 6919 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 29.59 _cell_measurement_theta_min 2.04 _cell_volume 926.0(3) _computing_cell_refinement 'STOE X-AREA (Stoe & Cie, 2006)' _computing_data_collection 'STOE X-AREA (Stoe & Cie, 2006)' _computing_data_reduction 'STOE X-RED (Stoe & Cie, 2006)' _computing_molecular_graphics 'Mercury (Macrae et al., 2006)' _computing_publication_material ; Mercury (Macrae et al., 2006), PLATON (Spek, 2009), enCIFer (Allen et al., 2004) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, 2008) and X-STEP32 (Stoe & Cie, 2000) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 200(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.864 _diffrn_measured_fraction_theta_max 0.864 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0916 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 9663 _diffrn_reflns_theta_full 29.18 _diffrn_reflns_theta_max 29.18 _diffrn_reflns_theta_min 2.03 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.191 _refine_diff_density_min -0.208 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.891 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 4312 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.891 _refine_ls_R_factor_all 0.1096 _refine_ls_R_factor_gt 0.0491 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.0805 _reflns_number_gt 2491 _reflns_number_total 4312 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.91550 20.21550 10.18620 85.57800 113.13300 88.30100 ZERR 4 0.00070 0.00330 0.00160 0.01400 0.01100 0.01300 LATT 1 SFAC C H N O UNIT 28 52 4 24 TEMP -73 PLAN 100 FMAP 2 L.S. 30 BOND CONF ACTA EQIV $1 1-X,2-Y,1-Z EQIV $2 X,1+Y,Z EQIV $3 1-X,1-Y,2-Z EQIV $4 1+X,-1+Y,Z EQIV $5 1-X,1-Y,2-Z EQIV $6 -1+X,Y,Z EQIV $7 1-X,1-Y,1-Z HTAB O14 O21_$4 HTAB O16 O12_$5 HTAB N11 O15 HTAB N11 O23_$7 HTAB N11 O23 HTAB O24 O11_$6 HTAB O26 O22_$1 HTAB N21 O25 HTAB N21 O13_$3 HTAB N21 O13_$2 BOND $H WGHT 0.026600 FVAR 0.75160 O23 4 0.187129 0.588955 0.451665 11.00000 0.03224 0.01970 = 0.02982 -0.00673 0.01529 -0.00346 O25 4 0.652399 0.848150 0.750645 11.00000 0.04193 0.02308 = 0.02832 -0.00796 0.02128 -0.00675 O26 4 0.851063 0.904098 0.622468 11.00000 0.03922 0.02422 = 0.02953 -0.00738 0.01894 -0.01161 AFIX 147 H26 2 0.878794 0.901077 0.546807 11.00000 -1.50000 AFIX 0 O21 4 0.128214 1.055137 0.824243 11.00000 0.03076 0.02633 = 0.02392 -0.00090 0.01444 0.00631 O22 4 0.012362 1.091227 0.595386 11.00000 0.02790 0.03389 = 0.02680 0.00681 0.01274 0.00779 O13 4 0.771930 0.087688 1.014314 11.00000 0.02935 0.01920 = 0.02642 0.00033 0.01175 0.00138 O24 4 0.071810 0.654526 0.590010 11.00000 0.04532 0.02337 = 0.04279 -0.01149 0.03280 -0.01471 AFIX 147 H24 2 0.001991 0.619683 0.610527 11.00000 -1.50000 AFIX 0 O16 4 0.184462 0.403815 0.909212 11.00000 0.04577 0.02506 = 0.03046 0.00215 0.02006 0.01071 AFIX 147 H16 2 0.180897 0.404200 0.990924 11.00000 -1.50000 AFIX 0 O14 4 0.792725 0.153543 0.834290 11.00000 0.03961 0.02447 = 0.03085 0.00429 0.02216 0.00938 AFIX 147 H14 2 0.894942 0.120589 0.829083 11.00000 -1.50000 AFIX 0 O15 4 0.407294 0.345545 0.803361 11.00000 0.06385 0.02482 = 0.03721 0.00240 0.03624 0.00473 N21 3 0.577898 0.970954 0.845611 11.00000 0.02640 0.02075 = 0.02252 -0.00293 0.01212 0.00360 AFIX 137 H21A 2 0.695727 0.937975 0.835119 11.00000 -1.50000 H21B 2 0.452017 0.952918 0.882180 11.00000 -1.50000 H21C 2 0.692620 0.999238 0.906446 11.00000 -1.50000 AFIX 0 C22 1 0.404143 1.007982 0.704040 11.00000 0.02015 0.02201 = 0.01946 -0.00331 0.00926 -0.00141 AFIX 23 H22A 2 0.311915 0.975936 0.633055 11.00000 -1.20000 H22B 2 0.539383 1.033516 0.671966 11.00000 -1.20000 AFIX 0 C13 1 0.701979 0.140246 0.938098 11.00000 0.01826 0.01913 = 0.02212 -0.00618 0.00746 -0.00445 C25 1 0.471847 0.745115 0.576727 11.00000 0.02576 0.02154 = 0.02147 -0.00427 0.01194 -0.00613 AFIX 23 H25A 2 0.325577 0.761480 0.613268 11.00000 -1.20000 H25B 2 0.627493 0.716785 0.655727 11.00000 -1.20000 AFIX 0 C23 1 0.186295 0.643260 0.497236 11.00000 0.01844 0.02174 = 0.02026 -0.00261 0.00658 -0.00314 C21 1 0.163327 1.055435 0.708947 11.00000 0.01805 0.01723 = 0.02408 -0.00359 0.01021 -0.00501 C26 1 0.612037 0.804234 0.532026 11.00000 0.02513 0.01944 = 0.02013 -0.00350 0.01066 -0.00366 AFIX 23 H26A 2 0.786479 0.788025 0.515142 11.00000 -1.20000 H26B 2 0.467437 0.827289 0.440834 11.00000 -1.20000 AFIX 0 C24 1 0.317395 0.703272 0.452563 11.00000 0.03071 0.02337 = 0.02178 -0.00561 0.01373 -0.00826 AFIX 23 H24A 2 0.157561 0.731286 0.374886 11.00000 -1.20000 H24B 2 0.462256 0.688221 0.413942 11.00000 -1.20000 AFIX 0 C16 1 0.501463 0.308151 1.047135 11.00000 0.02677 0.02051 = 0.02352 -0.00546 0.00714 0.00040 AFIX 23 H16A 2 0.343474 0.290715 1.074842 11.00000 -1.20000 H16B 2 0.624957 0.334815 1.123749 11.00000 -1.20000 AFIX 0 C14 1 0.508340 0.195457 0.953445 11.00000 0.02271 0.01910 = 0.03004 -0.00369 0.01219 -0.00095 AFIX 23 H14A 2 0.387686 0.177189 1.004215 11.00000 -1.20000 H14B 2 0.371332 0.215181 0.857099 11.00000 -1.20000 AFIX 0 C15 1 0.694277 0.249637 1.036952 11.00000 0.02285 0.02662 = 0.02803 -0.00662 0.00083 0.00449 AFIX 23 H15A 2 0.823794 0.230237 1.134885 11.00000 -1.20000 H15B 2 0.823117 0.265976 0.988948 11.00000 -1.20000 AFIX 0 C27 1 0.707318 0.852715 0.644169 11.00000 0.02092 0.01612 = 0.02113 0.00044 0.00769 0.00318 C17 1 0.360472 0.352698 0.909195 11.00000 0.03240 0.01632 = 0.02976 -0.00321 0.01708 -0.00499 O11 4 0.839977 0.551586 0.654155 11.00000 0.03051 0.02646 = 0.02485 -0.00693 0.01550 -0.01228 O12 4 0.933456 0.587584 0.868472 11.00000 0.03309 0.03334 = 0.03058 -0.01630 0.01652 -0.01491 N11 3 0.428800 0.470274 0.663081 11.00000 0.02540 0.02136 = 0.02182 -0.00281 0.01277 -0.00765 AFIX 137 H11A 2 0.313696 0.440039 0.683211 11.00000 -1.50000 H11B 2 0.566447 0.448889 0.639558 11.00000 -1.50000 H11C 2 0.313079 0.499677 0.588168 11.00000 -1.50000 AFIX 0 C12 1 0.580910 0.506543 0.790911 11.00000 0.01870 0.02076 = 0.01900 -0.00196 0.00882 -0.00147 AFIX 23 H12A 2 0.685796 0.474065 0.875270 11.00000 -1.20000 H12B 2 0.431417 0.533104 0.810840 11.00000 -1.20000 AFIX 0 C11 1 0.802275 0.552393 0.768633 11.00000 0.01582 0.01693 = 0.02384 -0.00091 0.00844 0.00048 HKLF 4 REM REM R1 = 0.0491 for 2491 Fo > 4sig(Fo) and 0.1096 for all 4312 data REM 259 parameters refined using 0 restraints END WGHT 0.0266 0.0000 REM Highest difference peak 0.191, deepest hole -0.208, 1-sigma level 0.044 Q1 1 0.6861 0.5320 0.7759 11.00000 0.05 0.19 Q2 1 0.7921 0.8702 0.8188 11.00000 0.05 0.19 Q3 1 0.5226 0.6406 0.4209 11.00000 0.05 0.19 Q4 1 0.6722 0.8233 0.6010 11.00000 0.05 0.19 Q5 1 0.3982 0.3210 0.9744 11.00000 0.05 0.18 Q6 1 0.8942 0.2473 1.0783 11.00000 0.05 0.17 Q7 1 0.5740 0.3501 0.8553 11.00000 0.05 0.16 Q8 1 0.8080 0.5036 0.6228 11.00000 0.05 0.16 Q9 1 0.2126 0.7688 0.5456 11.00000 0.05 0.16 Q10 1 0.2680 0.2585 0.7589 11.00000 0.05 0.16 Q11 1 0.6528 0.5699 0.6467 11.00000 0.05 0.16 Q12 1 0.5815 0.8709 0.6573 11.00000 0.05 0.16 Q13 1 1.3087 0.5962 0.9970 11.00000 0.05 0.15 Q14 1 1.1535 0.5600 0.9437 11.00000 0.05 0.15 Q15 1 0.6149 0.4925 0.9623 11.00000 0.05 0.15 Q16 1 0.7219 0.9294 1.0181 11.00000 0.05 0.14 Q17 1 0.1391 0.5604 0.5200 11.00000 0.05 0.14 Q18 1 0.2537 1.0243 0.7236 11.00000 0.05 0.14 Q19 1 0.7437 0.8021 0.4534 11.00000 0.05 0.14 Q20 1 0.2378 0.8241 0.6005 11.00000 0.05 0.14 Q21 1 -0.0771 1.1248 0.6187 11.00000 0.05 0.14 Q22 1 0.1709 1.0291 0.9013 11.00000 0.05 0.14 Q23 1 0.3040 0.3440 0.7071 11.00000 0.05 0.14 Q24 1 0.6180 0.1784 0.9412 11.00000 0.05 0.14 Q25 1 0.5864 0.8673 0.8318 11.00000 0.05 0.14 Q26 1 -0.0362 1.0783 0.7950 11.00000 0.05 0.14 Q27 1 0.5015 0.9923 0.7758 11.00000 0.05 0.14 Q28 1 0.3184 0.8676 0.7791 11.00000 0.05 0.14 Q29 1 0.5468 0.8024 0.7615 11.00000 0.05 0.14 Q30 1 0.7176 0.4616 0.9435 11.00000 0.05 0.14 Q31 1 0.8335 0.3066 1.2013 11.00000 0.05 0.14 Q32 1 0.2142 0.8520 0.3595 11.00000 0.05 0.13 Q33 1 0.3471 0.5843 0.4459 11.00000 0.05 0.13 Q34 1 0.7654 0.2165 1.1874 11.00000 0.05 0.13 Q35 1 0.5428 0.3016 0.8388 11.00000 0.05 0.13 Q36 1 0.0084 0.4740 0.6827 11.00000 0.05 0.13 Q37 1 1.1159 0.8773 0.6396 11.00000 0.05 0.13 Q38 1 0.2036 0.3282 0.6314 11.00000 0.05 0.13 Q39 1 0.7317 0.1317 1.1533 11.00000 0.05 0.13 Q40 1 0.7156 0.0772 0.7550 11.00000 0.05 0.13 Q41 1 -0.0399 0.5515 0.4661 11.00000 0.05 0.13 Q42 1 0.8216 0.3220 0.8938 11.00000 0.05 0.13 Q43 1 0.5792 0.4509 0.9828 11.00000 0.05 0.13 Q44 1 0.8770 0.6020 0.7649 11.00000 0.05 0.13 Q45 1 0.1557 1.1081 0.6619 11.00000 0.05 0.12 Q46 1 0.0926 0.1824 0.8448 11.00000 0.05 0.12 Q47 1 -0.1144 0.7122 0.3597 11.00000 0.05 0.12 Q48 1 0.4246 0.5288 0.8889 11.00000 0.05 0.12 Q49 1 0.8948 0.0606 0.9830 11.00000 0.05 0.12 Q50 1 0.7571 0.2795 0.8950 11.00000 0.05 0.12 Q51 1 0.3570 0.4693 0.5003 11.00000 0.05 0.12 Q52 1 0.3005 0.5878 0.5560 11.00000 0.05 0.12 Q53 1 0.7316 1.0149 0.7014 11.00000 0.05 0.12 Q54 1 0.6596 0.0624 0.9811 11.00000 0.05 0.12 Q55 1 0.9632 0.2658 0.8991 11.00000 0.05 0.12 Q56 1 0.3977 0.7355 0.4952 11.00000 0.05 0.12 Q57 1 0.7838 0.9677 0.5547 11.00000 0.05 0.12 Q58 1 0.7336 0.3777 0.8975 11.00000 0.05 0.12 Q59 1 0.5297 0.1007 0.8006 11.00000 0.05 0.12 Q60 1 0.4963 0.9677 1.0209 11.00000 0.05 0.12 Q61 1 0.8431 0.9939 0.7568 11.00000 0.05 0.12 Q62 1 0.4162 0.3585 0.6764 11.00000 0.05 0.12 Q63 1 0.3128 0.6690 0.4988 11.00000 0.05 0.12 Q64 1 0.9700 0.6326 0.8360 11.00000 0.05 0.12 Q65 1 0.4472 0.3397 1.1797 11.00000 0.05 0.12 Q66 1 0.4274 0.1522 1.0615 11.00000 0.05 0.12 Q67 1 -0.2837 1.0823 0.4982 11.00000 0.05 0.12 Q68 1 0.3129 0.8936 0.3873 11.00000 0.05 0.12 Q69 1 0.3620 0.5897 0.8163 11.00000 0.05 0.12 Q70 1 0.8549 0.5256 0.5444 11.00000 0.05 0.12 Q71 1 0.6472 0.7043 0.7382 11.00000 0.05 0.12 Q72 1 0.7392 0.5326 0.5617 11.00000 0.05 0.11 Q73 1 0.7231 0.1882 1.2588 11.00000 0.05 0.11 Q74 1 0.0708 1.0632 0.9206 11.00000 0.05 0.11 Q75 1 0.5000 0.5000 0.5000 10.50000 0.05 0.11 Q76 1 0.8918 0.3097 1.1349 11.00000 0.05 0.11 Q77 1 0.2284 0.6501 0.5809 11.00000 0.05 0.11 Q78 1 0.3857 0.2866 0.7604 11.00000 0.05 0.11 Q79 1 0.4039 0.4272 0.4986 11.00000 0.05 0.11 Q80 1 0.4133 0.4220 1.0005 11.00000 0.05 0.11 Q81 1 0.8445 0.2029 0.8147 11.00000 0.05 0.11 Q82 1 0.7623 0.5947 0.8180 11.00000 0.05 0.11 Q83 1 0.5374 0.7795 0.5610 11.00000 0.05 0.11 Q84 1 0.7955 0.4062 0.8142 11.00000 0.05 0.11 Q85 1 0.7401 0.8291 0.7171 11.00000 0.05 0.11 Q86 1 0.8386 1.0560 0.8798 11.00000 0.05 0.11 Q87 1 -0.0462 0.7046 0.5472 11.00000 0.05 0.11 Q88 1 0.4793 0.4109 0.9150 11.00000 0.05 0.11 Q89 1 0.6576 0.7251 0.3220 11.00000 0.05 0.11 Q90 1 1.1562 0.8653 0.5627 11.00000 0.05 0.11 Q91 1 0.3130 0.6372 0.3332 11.00000 0.05 0.11 Q92 1 -0.0733 1.1121 0.5013 11.00000 0.05 0.11 Q93 1 0.7964 0.5807 0.5804 11.00000 0.05 0.11 Q94 1 0.5021 0.3080 0.7212 11.00000 0.05 0.11 Q95 1 -0.1620 1.0757 0.4614 11.00000 0.05 0.11 Q96 1 0.9205 0.5792 0.6934 11.00000 0.05 0.11 Q97 1 0.7983 0.6978 0.4578 11.00000 0.05 0.11 Q98 1 1.0496 0.6044 0.8745 11.00000 0.05 0.11 Q99 1 0.0837 1.0322 0.7510 11.00000 0.05 0.11 Q100 1 0.5287 0.7566 0.3046 11.00000 0.05 0.11 ; _cod_data_source_file gp5050.cif _cod_data_source_block 200 _cod_original_cell_volume 926.1(2) _cod_database_code 2105117 _cod_database_fobs_code 2105117 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O23 0.1871(4) 0.58896(6) 0.45166(16) 0.0260(4) Uani d . 1 O O25 0.6524(4) 0.84815(6) 0.75064(16) 0.0284(4) Uani d . 1 O O26 0.8511(4) 0.90410(6) 0.62247(16) 0.0289(4) Uani d . 1 H H26 0.8788 0.9011 0.5468 0.043 Uiso calc R 1 O O21 0.1282(3) 1.05514(6) 0.82424(16) 0.0261(3) Uani d . 1 O O22 0.0124(4) 1.09123(7) 0.59539(16) 0.0297(4) Uani d . 1 O O13 0.7719(3) 0.08769(6) 1.01431(16) 0.0250(3) Uani d . 1 O O24 0.0718(4) 0.65453(6) 0.59001(18) 0.0316(4) Uani d . 1 H H24 0.0020 0.6197 0.6105 0.047 Uiso calc R 1 O O16 0.1845(4) 0.40381(7) 0.90921(17) 0.0328(4) Uani d . 1 H H16 0.1809 0.4042 0.9909 0.049 Uiso calc R 1 O O14 0.7927(4) 0.15354(6) 0.83429(16) 0.0297(4) Uani d . 1 H H14 0.8949 0.1206 0.8291 0.045 Uiso calc R 1 O O15 0.4073(4) 0.34554(6) 0.80336(18) 0.0374(4) Uani d . 1 N N21 0.5779(4) 0.97095(7) 0.84561(18) 0.0225(4) Uani d . 1 H H21A 0.6957 0.9380 0.8351 0.034 Uiso calc R 1 H H21B 0.4520 0.9529 0.8822 0.034 Uiso calc R 1 H H21C 0.6926 0.9992 0.9064 0.034 Uiso calc R 1 C C22 0.4041(5) 1.00798(9) 0.7040(2) 0.0200(4) Uani d . 1 H H22A 0.3119 0.9759 0.6331 0.024 Uiso calc R 1 H H22B 0.5394 1.0335 0.6720 0.024 Uiso calc R 1 C C13 0.7020(5) 0.14025(8) 0.9381(2) 0.0197(4) Uani d . 1 C C25 0.4718(5) 0.74512(9) 0.5767(2) 0.0219(4) Uani d . 1 H H25A 0.3256 0.7615 0.6133 0.026 Uiso calc R 1 H H25B 0.6275 0.7168 0.6557 0.026 Uiso calc R 1 C C23 0.1863(5) 0.64326(9) 0.4972(2) 0.0204(4) Uani d . 1 C C21 0.1633(5) 1.05543(8) 0.7089(2) 0.0190(4) Uani d . 1 C C26 0.6120(5) 0.80423(8) 0.5320(2) 0.0209(4) Uani d . 1 H H26A 0.7865 0.7880 0.5151 0.025 Uiso calc R 1 H H26B 0.4674 0.8273 0.4408 0.025 Uiso calc R 1 C C24 0.3174(5) 0.70327(9) 0.4526(2) 0.0239(5) Uani d . 1 H H24A 0.1576 0.7313 0.3749 0.029 Uiso calc R 1 H H24B 0.4623 0.6882 0.4139 0.029 Uiso calc R 1 C C16 0.5015(5) 0.30815(9) 1.0471(2) 0.0243(5) Uani d . 1 H H16A 0.3435 0.2907 1.0748 0.029 Uiso calc R 1 H H16B 0.6250 0.3348 1.1237 0.029 Uiso calc R 1 C C14 0.5083(5) 0.19546(9) 0.9534(2) 0.0233(4) Uani d . 1 H H14A 0.3877 0.1772 1.0042 0.028 Uiso calc R 1 H H14B 0.3713 0.2152 0.8571 0.028 Uiso calc R 1 C C15 0.6943(5) 0.24964(9) 1.0370(2) 0.0286(5) Uani d . 1 H H15A 0.8238 0.2302 1.1349 0.034 Uiso calc R 1 H H15B 0.8231 0.2660 0.9889 0.034 Uiso calc R 1 C C27 0.7073(5) 0.85271(8) 0.6442(2) 0.0198(4) Uani d . 1 C C17 0.3605(5) 0.35270(9) 0.9092(2) 0.0245(5) Uani d . 1 O O11 0.8400(3) 0.55159(6) 0.65415(15) 0.0254(3) Uani d . 1 O O12 0.9335(4) 0.58758(7) 0.86847(17) 0.0301(4) Uani d . 1 N N11 0.4288(4) 0.47027(7) 0.66308(18) 0.0216(4) Uani d . 1 H H11A 0.3137 0.4400 0.6832 0.032 Uiso calc R 1 H H11B 0.5664 0.4489 0.6396 0.032 Uiso calc R 1 H H11C 0.3131 0.4997 0.5882 0.032 Uiso calc R 1 C C12 0.5809(5) 0.50654(8) 0.7909(2) 0.0191(4) Uani d . 1 H H12A 0.6858 0.4741 0.8753 0.023 Uiso calc R 1 H H12B 0.4314 0.5331 0.8108 0.023 Uiso calc R 1 C C11 0.8023(5) 0.55239(8) 0.7686(2) 0.0188(4) Uani d . 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O23 0.0322(10) 0.0197(7) 0.0298(9) -0.0035(6) 0.0153(8) -0.0067(6) O25 0.0419(10) 0.0231(7) 0.0283(9) -0.0067(6) 0.0213(8) -0.0080(6) O26 0.0392(10) 0.0242(7) 0.0295(9) -0.0116(6) 0.0189(8) -0.0074(6) O21 0.0308(9) 0.0263(7) 0.0239(8) 0.0063(6) 0.0144(7) -0.0009(6) O22 0.0279(9) 0.0339(8) 0.0268(9) 0.0078(6) 0.0127(7) 0.0068(6) O13 0.0293(9) 0.0192(7) 0.0264(9) 0.0014(6) 0.0118(7) 0.0003(5) O24 0.0453(11) 0.0234(7) 0.0428(10) -0.0147(7) 0.0328(9) -0.0115(6) O16 0.0458(12) 0.0251(7) 0.0305(9) 0.0107(6) 0.0201(9) 0.0021(6) O14 0.0396(11) 0.0245(7) 0.0308(9) 0.0094(6) 0.0222(8) 0.0043(6) O15 0.0639(13) 0.0248(8) 0.0372(10) 0.0047(7) 0.0362(10) 0.0024(6) N21 0.0264(10) 0.0208(8) 0.0225(9) 0.0036(7) 0.0121(8) -0.0029(6) C22 0.0201(11) 0.0220(9) 0.0195(10) -0.0014(7) 0.0093(9) -0.0033(7) C13 0.0183(11) 0.0191(9) 0.0221(11) -0.0045(7) 0.0075(9) -0.0062(7) C25 0.0258(12) 0.0215(9) 0.0215(11) -0.0061(8) 0.0119(9) -0.0043(7) C23 0.0184(11) 0.0217(9) 0.0203(11) -0.0031(7) 0.0066(9) -0.0026(7) C21 0.0180(11) 0.0172(9) 0.0241(11) -0.0050(7) 0.0102(9) -0.0036(7) C26 0.0251(12) 0.0194(9) 0.0201(11) -0.0037(7) 0.0107(9) -0.0035(7) C24 0.0307(13) 0.0234(9) 0.0218(11) -0.0083(8) 0.0137(10) -0.0056(7) C16 0.0268(12) 0.0205(9) 0.0235(11) 0.0004(8) 0.0071(10) -0.0055(7) C14 0.0227(12) 0.0191(9) 0.0300(12) -0.0010(7) 0.0122(10) -0.0037(7) C15 0.0228(12) 0.0266(10) 0.0280(12) 0.0045(8) 0.0008(10) -0.0066(8) C27 0.0209(11) 0.0161(9) 0.0211(11) 0.0032(7) 0.0077(9) 0.0004(7) C17 0.0324(13) 0.0163(9) 0.0298(12) -0.0050(8) 0.0171(11) -0.0032(8) O11 0.0305(9) 0.0265(7) 0.0249(8) -0.0123(6) 0.0155(7) -0.0069(6) O12 0.0331(10) 0.0333(8) 0.0306(9) -0.0149(7) 0.0165(8) -0.0163(6) N11 0.0254(10) 0.0214(8) 0.0218(9) -0.0076(7) 0.0128(8) -0.0028(6) C12 0.0187(11) 0.0208(9) 0.0190(10) -0.0015(7) 0.0088(9) -0.0020(7) C11 0.0158(10) 0.0169(9) 0.0238(11) 0.0005(7) 0.0084(9) -0.0009(7) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C27 O26 H26 109.5 C23 O24 H24 109.5 C17 O16 H16 109.5 C13 O14 H14 109.5 C22 N21 H21A 109.5 C22 N21 H21B 109.5 H21A N21 H21B 109.5 C22 N21 H21C 109.5 H21A N21 H21C 109.5 H21B N21 H21C 109.5 N21 C22 C21 112.13(16) N21 C22 H22A 109.2 C21 C22 H22A 109.2 N21 C22 H22B 109.2 C21 C22 H22B 109.2 H22A C22 H22B 107.9 O13 C13 O14 122.23(18) O13 C13 C14 124.05(18) O14 C13 C14 113.72(16) C26 C25 C24 112.25(16) C26 C25 H25A 109.2 C24 C25 H25A 109.2 C26 C25 H25B 109.2 C24 C25 H25B 109.2 H25A C25 H25B 107.9 O23 C23 O24 122.74(17) O23 C23 C24 123.6(2) O24 C23 C24 113.64(17) O21 C21 O22 125.30(19) O21 C21 C22 117.85(17) O22 C21 C22 116.85(17) C27 C26 C25 111.92(17) C27 C26 H26A 109.2 C25 C26 H26A 109.2 C27 C26 H26B 109.2 C25 C26 H26B 109.2 H26A C26 H26B 107.9 C23 C24 C25 112.57(17) C23 C24 H24A 109.1 C25 C24 H24A 109.1 C23 C24 H24B 109.1 C25 C24 H24B 109.1 H24A C24 H24B 107.8 C17 C16 C15 113.30(18) C17 C16 H16A 108.9 C15 C16 H16A 108.9 C17 C16 H16B 108.9 C15 C16 H16B 108.9 H16A C16 H16B 107.7 C13 C14 C15 111.21(18) C13 C14 H14A 109.4 C15 C14 H14A 109.4 C13 C14 H14B 109.4 C15 C14 H14B 109.4 H14A C14 H14B 108.0 C16 C15 C14 112.17(19) C16 C15 H15A 109.2 C14 C15 H15A 109.2 C16 C15 H15B 109.2 C14 C15 H15B 109.2 H15A C15 H15B 107.9 O25 C27 O26 118.69(18) O25 C27 C26 123.50(17) O26 C27 C26 117.78(17) O15 C17 O16 119.58(19) O15 C17 C16 123.7(2) O16 C17 C16 116.62(18) C12 N11 H11A 109.5 C12 N11 H11B 109.5 H11A N11 H11B 109.5 C12 N11 H11C 109.5 H11A N11 H11C 109.5 H11B N11 H11C 109.5 N11 C12 C11 111.60(16) N11 C12 H12A 109.3 C11 C12 H12A 109.3 N11 C12 H12B 109.3 C11 C12 H12B 109.3 H12A C12 H12B 108.0 O11 C11 O12 125.71(18) O11 C11 C12 117.77(17) O12 C11 C12 116.51(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O23 C23 1.225(2) O25 C27 1.214(2) O26 C27 1.326(2) O26 H26 0.8400 O21 C21 1.252(2) O22 C21 1.256(2) O13 C13 1.221(2) O24 C23 1.306(2) O24 H24 0.8400 O16 C17 1.328(3) O16 H16 0.8400 O14 C13 1.313(2) O14 H14 0.8400 O15 C17 1.205(3) N21 C22 1.482(2) N21 H21A 0.9100 N21 H21B 0.9100 N21 H21C 0.9100 C22 C21 1.520(3) C22 H22A 0.9900 C22 H22B 0.9900 C13 C14 1.502(3) C25 C26 1.524(2) C25 C24 1.530(3) C25 H25A 0.9900 C25 H25B 0.9900 C23 C24 1.512(3) C26 C27 1.505(3) C26 H26A 0.9900 C26 H26B 0.9900 C24 H24A 0.9900 C24 H24B 0.9900 C16 C17 1.506(3) C16 C15 1.529(3) C16 H16A 0.9900 C16 H16B 0.9900 C14 C15 1.533(3) C14 H14A 0.9900 C14 H14B 0.9900 C15 H15A 0.9900 C15 H15B 0.9900 O11 C11 1.252(2) O12 C11 1.257(2) N11 C12 1.486(3) N11 H11A 0.9100 N11 H11B 0.9100 N11 H11C 0.9100 C12 C11 1.522(3) C12 H12A 0.9900 C12 H12B 0.9900 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O14 H14 O21 1_645 0.84 1.74 2.580(2) 176.1 O16 H16 O12 2_667 0.84 1.75 2.565(2) 163.5 N11 H11A O15 . 0.91 2.12 2.827(2) 133.5 N11 H11B O23 2_666 0.91 1.96 2.860(2) 168.1 N11 H11C O23 . 0.91 2.11 2.971(2) 158.0 O24 H24 O11 1_455 0.84 1.72 2.5636(18) 176.0 O26 H26 O22 2_676 0.84 1.73 2.555(2) 167.3 N21 H21A O25 . 0.91 2.05 2.798(2) 138.5 N21 H21B O13 2_667 0.91 1.96 2.861(2) 172.2 N21 H21C O13 1_565 0.91 2.14 2.984(2) 154.5 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 N21 C22 C21 O21 -4.0(2) N21 C22 C21 O22 176.98(16) C24 C25 C26 C27 168.16(18) O23 C23 C24 C25 -142.3(2) O24 C23 C24 C25 37.5(3) C26 C25 C24 C23 178.14(18) O13 C13 C14 C15 99.0(2) O14 C13 C14 C15 -80.7(2) C17 C16 C15 C14 -75.0(2) C13 C14 C15 C16 176.98(18) C25 C26 C27 O25 -6.6(3) C25 C26 C27 O26 175.47(18) C15 C16 C17 O15 -4.1(3) C15 C16 C17 O16 178.57(19) N11 C12 C11 O11 -3.6(2) N11 C12 C11 O12 176.97(17)