#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105120.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_2105120 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 85.518(11) _cell_angle_beta 113.088(9) _cell_angle_gamma 88.264(11) _cell_formula_units_Z 4 _cell_length_a 4.8952(6) _cell_length_b 20.151(3) _cell_length_c 10.1585(13) _cell_measurement_reflns_used 8370 _cell_measurement_temperature 125(2) _cell_measurement_theta_max 29.61 _cell_measurement_theta_min 2.07 _cell_volume 917.0(2) _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 125(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.886 _diffrn_measured_fraction_theta_max 0.886 _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 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0641 _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 9997 _diffrn_reflns_theta_full 29.18 _diffrn_reflns_theta_max 29.18 _diffrn_reflns_theta_min 2.03 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.501 _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 0.229 _refine_diff_density_min -0.195 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 4391 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.899 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0391 _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^)+(0.0331P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.0754 _reflns_number_gt 2935 _reflns_number_total 4391 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.89520 20.15080 10.15850 85.51800 113.08800 88.26400 ZERR 4 0.00060 0.00290 0.00130 0.01100 0.00900 0.01100 LATT 1 SFAC C H N O UNIT 28 52 4 24 TEMP -148 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 0.033100 FVAR 0.75432 O23 4 0.187852 0.589107 0.450290 11.00000 0.01992 0.01387 = 0.01941 -0.00431 0.00868 -0.00227 O25 4 0.655728 0.848150 0.753016 11.00000 0.02629 0.01677 = 0.01758 -0.00413 0.01261 -0.00361 O26 4 0.856418 0.905068 0.624770 11.00000 0.02645 0.01629 = 0.01972 -0.00496 0.01326 -0.00692 AFIX 147 H26 2 0.881158 0.902601 0.547971 11.00000 -1.50000 AFIX 0 O21 4 0.127657 1.055644 0.824289 11.00000 0.01986 0.01878 = 0.01589 -0.00122 0.00922 0.00283 O22 4 0.004650 1.090417 0.593112 11.00000 0.01885 0.02159 = 0.01799 0.00414 0.00850 0.00371 O13 4 0.771469 0.087585 1.015449 11.00000 0.01822 0.01303 = 0.01701 -0.00070 0.00665 0.00006 O24 4 0.074685 0.654731 0.590450 11.00000 0.02906 0.01564 = 0.02820 -0.00724 0.02100 -0.00914 AFIX 147 H24 2 -0.003687 0.620371 0.607419 11.00000 -1.50000 AFIX 0 O16 4 0.179161 0.404789 0.907484 11.00000 0.03015 0.01749 = 0.01946 0.00075 0.01256 0.00634 AFIX 147 H16 2 0.169313 0.404562 0.988229 11.00000 -1.50000 AFIX 0 O14 4 0.785652 0.153456 0.832228 11.00000 0.02682 0.01639 = 0.02013 0.00231 0.01444 0.00563 AFIX 147 H14 2 0.888468 0.120398 0.827079 11.00000 -1.50000 AFIX 0 O15 4 0.403042 0.345427 0.801762 11.00000 0.04123 0.01782 = 0.02460 0.00060 0.02380 0.00148 N21 3 0.580400 0.971711 0.846094 11.00000 0.01729 0.01439 = 0.01479 -0.00142 0.00755 0.00229 AFIX 137 H21A 2 0.702419 0.939149 0.836579 11.00000 -1.50000 H21B 2 0.454193 0.952960 0.882108 11.00000 -1.50000 H21C 2 0.691731 1.000501 0.907100 11.00000 -1.50000 AFIX 0 C22 1 0.405903 1.008392 0.703584 11.00000 0.01383 0.01510 = 0.01229 -0.00162 0.00520 -0.00070 AFIX 23 H22A 2 0.316396 0.975988 0.632709 11.00000 -1.20000 H22B 2 0.540788 1.034490 0.671655 11.00000 -1.20000 AFIX 0 C13 1 0.696672 0.140316 0.937112 11.00000 0.01295 0.01277 = 0.01410 -0.00326 0.00490 -0.00267 C25 1 0.478059 0.745094 0.577831 11.00000 0.01829 0.01492 = 0.01525 -0.00352 0.00940 -0.00402 AFIX 23 H25A 2 0.331502 0.761306 0.614898 11.00000 -1.20000 H25B 2 0.634369 0.716441 0.656613 11.00000 -1.20000 AFIX 0 C23 1 0.189431 0.643652 0.497098 11.00000 0.01174 0.01596 = 0.01347 -0.00141 0.00362 -0.00077 C21 1 0.160135 1.055320 0.707661 11.00000 0.01290 0.01266 = 0.01681 -0.00324 0.00686 -0.00400 C26 1 0.619072 0.804689 0.533766 11.00000 0.01780 0.01441 = 0.01406 -0.00161 0.00795 -0.00218 AFIX 23 H26A 2 0.795545 0.788629 0.517649 11.00000 -1.20000 H26B 2 0.474774 0.827814 0.442058 11.00000 -1.20000 AFIX 0 C24 1 0.322407 0.703495 0.452883 11.00000 0.02104 0.01573 = 0.01639 -0.00333 0.00990 -0.00496 AFIX 23 H24A 2 0.162805 0.731876 0.375083 11.00000 -1.20000 H24B 2 0.467835 0.688241 0.414244 11.00000 -1.20000 AFIX 0 C16 1 0.497508 0.308488 1.047299 11.00000 0.01856 0.01468 = 0.01718 -0.00471 0.00545 -0.00039 AFIX 23 H16A 2 0.338691 0.291381 1.075438 11.00000 -1.20000 H16B 2 0.622287 0.335246 1.123730 11.00000 -1.20000 AFIX 0 C14 1 0.502207 0.195505 0.952981 11.00000 0.01591 0.01403 = 0.01820 -0.00157 0.00765 -0.00008 AFIX 23 H14A 2 0.380687 0.176966 1.003526 11.00000 -1.20000 H14B 2 0.365051 0.215584 0.856533 11.00000 -1.20000 AFIX 0 C15 1 0.688887 0.249618 1.037598 11.00000 0.01612 0.01803 = 0.02057 -0.00478 0.00187 0.00200 AFIX 23 H15A 2 0.816849 0.229913 1.135933 11.00000 -1.20000 H15B 2 0.820396 0.265761 0.990430 11.00000 -1.20000 AFIX 0 C27 1 0.711722 0.853307 0.646383 11.00000 0.01242 0.01154 = 0.01517 -0.00066 0.00312 0.00121 C17 1 0.356235 0.353108 0.908466 11.00000 0.02060 0.01197 = 0.02042 -0.00335 0.01089 -0.00455 O11 4 0.839171 0.551705 0.653479 11.00000 0.02097 0.01790 = 0.01694 -0.00408 0.01106 -0.00711 O12 4 0.939759 0.586712 0.869767 11.00000 0.02000 0.02290 = 0.01965 -0.00937 0.00974 -0.00785 N11 3 0.425022 0.470847 0.662489 11.00000 0.01816 0.01393 = 0.01555 -0.00157 0.00911 -0.00477 AFIX 137 H11A 2 0.307344 0.440896 0.682104 11.00000 -1.50000 H11B 2 0.562517 0.448987 0.639027 11.00000 -1.50000 H11C 2 0.310850 0.500686 0.587524 11.00000 -1.50000 AFIX 0 C12 1 0.579105 0.506726 0.791187 11.00000 0.01313 0.01452 = 0.01374 -0.00209 0.00577 -0.00156 AFIX 23 H12A 2 0.682344 0.473857 0.875569 11.00000 -1.20000 H12B 2 0.430097 0.533817 0.811123 11.00000 -1.20000 AFIX 0 C11 1 0.804752 0.552071 0.769368 11.00000 0.01296 0.01192 = 0.01615 -0.00098 0.00635 0.00039 HKLF 4 REM REM R1 = 0.0391 for 2935 Fo > 4sig(Fo) and 0.0764 for all 4391 data REM 259 parameters refined using 0 restraints END WGHT 0.0331 0.0000 REM Highest difference peak 0.229, deepest hole -0.195, 1-sigma level 0.045 Q1 1 0.6455 0.5357 0.7668 11.00000 0.05 0.23 Q2 1 0.3984 0.3271 0.9772 11.00000 0.05 0.21 Q3 1 0.3804 0.7309 0.5098 11.00000 0.05 0.20 Q4 1 0.6630 0.8296 0.5859 11.00000 0.05 0.18 Q5 1 0.3328 1.0401 0.7273 11.00000 0.05 0.18 Q6 1 0.2649 0.6770 0.4771 11.00000 0.05 0.18 Q7 1 0.1973 0.5603 0.5334 11.00000 0.05 0.17 Q8 1 0.5435 0.8701 0.8168 11.00000 0.05 0.16 Q9 1 0.4567 0.2606 0.7699 11.00000 0.05 0.16 Q10 1 0.7347 0.2258 1.1715 11.00000 0.05 0.16 Q11 1 0.5525 0.2287 0.9745 11.00000 0.05 0.15 Q12 1 0.6219 0.1708 0.9545 11.00000 0.05 0.15 Q13 1 0.2681 0.1798 0.7464 11.00000 0.05 0.15 Q14 1 0.0840 1.1079 0.5524 11.00000 0.05 0.15 Q15 1 0.8759 0.6041 0.9242 11.00000 0.05 0.15 Q16 1 0.7360 0.7556 0.3753 11.00000 0.05 0.15 Q17 1 0.7499 0.8832 0.7982 11.00000 0.05 0.15 Q18 1 0.6113 0.1888 1.1261 11.00000 0.05 0.15 Q19 1 0.5529 0.9378 0.6144 11.00000 0.05 0.15 Q20 1 1.1178 0.5722 0.9927 11.00000 0.05 0.15 Q21 1 0.8148 0.2821 0.8753 11.00000 0.05 0.14 Q22 1 0.5309 0.1492 1.0844 11.00000 0.05 0.14 Q23 1 -0.0553 0.5818 0.6277 11.00000 0.05 0.14 Q24 1 0.5356 0.8214 0.8044 11.00000 0.05 0.14 Q25 1 0.6540 0.1877 0.7763 11.00000 0.05 0.14 Q26 1 0.7048 0.1884 1.2354 11.00000 0.05 0.14 Q27 1 0.4905 0.4935 0.7284 11.00000 0.05 0.14 Q28 1 0.7744 0.8160 0.4219 11.00000 0.05 0.14 Q29 1 0.3375 0.5695 0.5604 11.00000 0.05 0.14 Q30 1 -0.0326 0.6988 0.5450 11.00000 0.05 0.14 Q31 1 0.2453 0.3824 0.7346 11.00000 0.05 0.14 Q32 1 1.0310 0.9098 0.7227 11.00000 0.05 0.14 Q33 1 0.4312 0.5928 0.8171 11.00000 0.05 0.13 Q34 1 0.2840 0.6980 0.7119 11.00000 0.05 0.13 Q35 1 -0.0824 1.1286 0.5846 11.00000 0.05 0.13 Q36 1 0.6995 0.5680 0.6555 11.00000 0.05 0.13 Q37 1 0.7762 0.9691 0.5595 11.00000 0.05 0.13 Q38 1 0.6016 0.5121 0.9560 11.00000 0.05 0.13 Q39 1 0.3170 0.1594 1.0840 11.00000 0.05 0.13 Q40 1 0.5355 0.0696 0.9219 11.00000 0.05 0.13 Q41 1 0.9907 0.2747 0.8684 11.00000 0.05 0.13 Q42 1 0.0703 1.1001 0.8235 11.00000 0.05 0.13 Q43 1 0.3191 0.7374 0.6746 11.00000 0.05 0.13 Q44 1 0.7735 0.4790 0.9952 11.00000 0.05 0.13 Q45 1 1.2019 0.5936 0.8840 11.00000 0.05 0.13 Q46 1 0.1948 0.2025 1.0614 11.00000 0.05 0.12 Q47 1 0.0519 0.4294 0.8314 11.00000 0.05 0.12 Q48 1 0.5795 0.3891 0.6090 11.00000 0.05 0.12 Q49 1 0.6443 0.8093 0.3223 11.00000 0.05 0.12 Q50 1 0.5601 0.7709 0.5657 11.00000 0.05 0.12 Q51 1 0.5309 0.2806 1.0241 11.00000 0.05 0.12 Q52 1 0.4207 0.9026 0.8431 11.00000 0.05 0.12 Q53 1 0.3505 1.0897 0.8264 11.00000 0.05 0.12 Q54 1 0.3545 0.6886 0.6596 11.00000 0.05 0.12 Q55 1 0.0489 1.1493 0.6946 11.00000 0.05 0.12 Q56 1 0.3960 0.7787 0.7120 11.00000 0.05 0.12 Q57 1 0.9091 0.3219 1.1456 11.00000 0.05 0.12 Q58 1 0.3693 0.3031 0.7826 11.00000 0.05 0.12 Q59 1 0.8607 0.2000 0.8137 11.00000 0.05 0.12 Q60 1 0.5399 0.8116 0.7251 11.00000 0.05 0.12 Q61 1 0.9426 0.4990 0.6473 11.00000 0.05 0.12 Q62 1 0.8072 0.6103 0.8294 11.00000 0.05 0.12 Q63 1 0.1471 0.1919 0.8853 11.00000 0.05 0.12 Q64 1 0.5618 0.5729 0.5897 11.00000 0.05 0.12 Q65 1 0.5074 0.6830 0.6225 11.00000 0.05 0.12 Q66 1 0.3952 0.3785 0.7313 11.00000 0.05 0.12 Q67 1 0.2530 0.4524 0.9482 11.00000 0.05 0.12 Q68 1 0.6199 0.6211 0.5696 11.00000 0.05 0.12 Q69 1 0.6069 1.0020 0.6641 11.00000 0.05 0.12 Q70 1 0.2275 0.5528 0.8245 11.00000 0.05 0.12 Q71 1 0.3463 0.4794 0.8659 11.00000 0.05 0.12 Q72 1 0.3148 1.0176 0.8982 11.00000 0.05 0.12 Q73 1 0.5381 0.7583 0.3183 11.00000 0.05 0.12 Q74 1 0.4631 0.1212 1.0743 11.00000 0.05 0.12 Q75 1 0.5620 0.3507 0.8198 11.00000 0.05 0.12 Q76 1 0.4412 0.9821 0.6158 11.00000 0.05 0.11 Q77 1 0.9375 0.5290 0.5558 11.00000 0.05 0.11 Q78 1 0.2650 0.3189 1.0463 11.00000 0.05 0.11 Q79 1 0.5991 0.4193 0.9813 11.00000 0.05 0.11 Q80 1 0.8841 0.4616 0.7767 11.00000 0.05 0.11 Q81 1 0.0215 1.0691 0.5180 11.00000 0.05 0.11 Q82 1 0.6080 1.0933 0.6048 11.00000 0.05 0.11 Q83 1 0.5492 0.1530 0.7372 11.00000 0.05 0.11 Q84 1 0.4989 0.9911 0.7766 11.00000 0.05 0.11 Q85 1 0.5269 0.6476 0.4619 11.00000 0.05 0.11 Q86 1 0.9332 0.9285 0.9816 11.00000 0.05 0.11 Q87 1 0.7288 0.3949 0.9695 11.00000 0.05 0.11 Q88 1 0.0418 0.5779 0.4618 11.00000 0.05 0.11 Q89 1 0.5743 0.3447 1.2403 11.00000 0.05 0.11 Q90 1 0.9552 0.1968 0.8983 11.00000 0.05 0.11 Q91 1 0.6860 0.6495 0.7211 11.00000 0.05 0.11 Q92 1 -0.0105 0.4606 0.9816 11.00000 0.05 0.11 Q93 1 0.5079 0.1071 0.8524 11.00000 0.05 0.11 Q94 1 0.4141 1.0337 0.5083 11.00000 0.05 0.11 Q95 1 0.3871 0.4131 0.5031 11.00000 0.05 0.11 Q96 1 0.7578 0.8405 0.7229 11.00000 0.05 0.11 Q97 1 0.7361 0.5296 0.6031 11.00000 0.05 0.11 Q98 1 0.7052 0.1408 1.1955 11.00000 0.05 0.11 Q99 1 0.8922 0.7470 0.7366 11.00000 0.05 0.11 Q100 1 0.7616 0.3506 0.8657 11.00000 0.05 0.11 ; _cod_data_source_file gp5050.cif _cod_data_source_block 125 _cod_original_cell_volume 916.9(2) _cod_database_code 2105120 _cod_database_fobs_code 2105120 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 0.1879(3) 0.58911(5) 0.45029(12) 0.0173(2) Uani d . 1 O O25 0.6557(3) 0.84815(5) 0.75302(12) 0.0188(2) Uani d . 1 O O26 0.8564(3) 0.90507(5) 0.62477(12) 0.0192(2) Uani d . 1 H H26 0.8812 0.9026 0.5480 0.029 Uiso calc R 1 O O21 0.1277(3) 1.05564(5) 0.82429(12) 0.0176(2) Uani d . 1 O O22 0.0047(3) 1.09042(5) 0.59311(12) 0.0196(2) Uani d . 1 O O13 0.7715(3) 0.08758(5) 1.01545(12) 0.0163(2) Uani d . 1 O O24 0.0747(3) 0.65473(5) 0.59045(13) 0.0208(3) Uani d . 1 H H24 -0.0037 0.6204 0.6074 0.031 Uiso calc R 1 O O16 0.1792(3) 0.40479(5) 0.90748(13) 0.0218(3) Uani d . 1 H H16 0.1693 0.4046 0.9882 0.033 Uiso calc R 1 O O14 0.7857(3) 0.15346(5) 0.83223(12) 0.0199(2) Uani d . 1 H H14 0.8885 0.1204 0.8271 0.030 Uiso calc R 1 O O15 0.4030(3) 0.34543(5) 0.80176(13) 0.0248(3) Uani d . 1 N N21 0.5804(3) 0.97171(6) 0.84609(14) 0.0152(3) Uani d . 1 H H21A 0.7024 0.9391 0.8366 0.023 Uiso calc R 1 H H21B 0.4542 0.9530 0.8821 0.023 Uiso calc R 1 H H21C 0.6917 1.0005 0.9071 0.023 Uiso calc R 1 C C22 0.4059(3) 1.00839(7) 0.70358(16) 0.0137(3) Uani d . 1 H H22A 0.3164 0.9760 0.6327 0.016 Uiso calc R 1 H H22B 0.5408 1.0345 0.6717 0.016 Uiso calc R 1 C C13 0.6967(3) 0.14032(7) 0.93711(16) 0.0133(3) Uani d . 1 C C25 0.4781(4) 0.74509(7) 0.57783(16) 0.0151(3) Uani d . 1 H H25A 0.3315 0.7613 0.6149 0.018 Uiso calc R 1 H H25B 0.6344 0.7164 0.6566 0.018 Uiso calc R 1 C C23 0.1894(3) 0.64365(7) 0.49710(16) 0.0142(3) Uani d . 1 C C21 0.1601(3) 1.05532(7) 0.70766(16) 0.0136(3) Uani d . 1 C C26 0.6191(4) 0.80469(7) 0.53377(16) 0.0149(3) Uani d . 1 H H26A 0.7955 0.7886 0.5176 0.018 Uiso calc R 1 H H26B 0.4748 0.8278 0.4421 0.018 Uiso calc R 1 C C24 0.3224(4) 0.70350(7) 0.45288(17) 0.0168(3) Uani d . 1 H H24A 0.1628 0.7319 0.3751 0.020 Uiso calc R 1 H H24B 0.4678 0.6882 0.4142 0.020 Uiso calc R 1 C C16 0.4975(4) 0.30849(7) 1.04730(17) 0.0172(3) Uani d . 1 H H16A 0.3387 0.2914 1.0754 0.021 Uiso calc R 1 H H16B 0.6223 0.3352 1.1237 0.021 Uiso calc R 1 C C14 0.5022(4) 0.19550(7) 0.95298(17) 0.0158(3) Uani d . 1 H H14A 0.3807 0.1770 1.0035 0.019 Uiso calc R 1 H H14B 0.3651 0.2156 0.8565 0.019 Uiso calc R 1 C C15 0.6889(4) 0.24962(7) 1.03760(18) 0.0198(3) Uani d . 1 H H15A 0.8168 0.2299 1.1359 0.024 Uiso calc R 1 H H15B 0.8204 0.2658 0.9904 0.024 Uiso calc R 1 C C27 0.7117(3) 0.85331(7) 0.64638(16) 0.0139(3) Uani d . 1 C C17 0.3562(4) 0.35311(7) 0.90847(17) 0.0166(3) Uani d . 1 O O11 0.8392(3) 0.55171(5) 0.65348(12) 0.0172(2) Uani d . 1 O O12 0.9398(3) 0.58671(5) 0.86977(12) 0.0197(2) Uani d . 1 N N11 0.4250(3) 0.47085(6) 0.66249(14) 0.0150(3) Uani d . 1 H H11A 0.3073 0.4409 0.6821 0.023 Uiso calc R 1 H H11B 0.5625 0.4490 0.6390 0.023 Uiso calc R 1 H H11C 0.3109 0.5007 0.5875 0.023 Uiso calc R 1 C C12 0.5791(3) 0.50673(7) 0.79119(16) 0.0136(3) Uani d . 1 H H12A 0.6823 0.4739 0.8756 0.016 Uiso calc R 1 H H12B 0.4301 0.5338 0.8111 0.016 Uiso calc R 1 C C11 0.8048(3) 0.55207(7) 0.76937(16) 0.0135(3) 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 0.0199(6) 0.0139(5) 0.0194(6) -0.0023(4) 0.0087(5) -0.0043(4) O25 0.0263(6) 0.0168(5) 0.0176(6) -0.0036(4) 0.0126(5) -0.0041(4) O26 0.0264(7) 0.0163(5) 0.0197(6) -0.0069(4) 0.0133(5) -0.0050(4) O21 0.0199(6) 0.0188(5) 0.0159(6) 0.0028(4) 0.0092(5) -0.0012(4) O22 0.0188(6) 0.0216(5) 0.0180(6) 0.0037(4) 0.0085(5) 0.0041(4) O13 0.0182(6) 0.0130(5) 0.0170(6) 0.0001(4) 0.0066(5) -0.0007(4) O24 0.0291(7) 0.0156(5) 0.0282(6) -0.0091(5) 0.0210(6) -0.0072(4) O16 0.0301(7) 0.0175(5) 0.0195(6) 0.0063(4) 0.0126(6) 0.0007(4) O14 0.0268(7) 0.0164(5) 0.0201(6) 0.0056(4) 0.0144(5) 0.0023(4) O15 0.0412(8) 0.0178(5) 0.0246(6) 0.0015(5) 0.0238(6) 0.0006(4) N21 0.0173(7) 0.0144(6) 0.0148(6) 0.0023(5) 0.0075(5) -0.0014(4) C22 0.0138(7) 0.0151(6) 0.0123(7) -0.0007(5) 0.0052(6) -0.0016(5) C13 0.0129(7) 0.0128(6) 0.0141(7) -0.0027(5) 0.0049(6) -0.0033(5) C25 0.0183(8) 0.0149(7) 0.0152(7) -0.0040(5) 0.0094(6) -0.0035(5) C23 0.0117(7) 0.0160(7) 0.0135(7) -0.0008(5) 0.0036(6) -0.0014(5) C21 0.0129(7) 0.0127(6) 0.0168(7) -0.0040(5) 0.0069(6) -0.0032(5) C26 0.0178(8) 0.0144(7) 0.0141(7) -0.0022(5) 0.0080(6) -0.0016(5) C24 0.0210(8) 0.0157(7) 0.0164(7) -0.0050(6) 0.0099(7) -0.0033(5) C16 0.0186(8) 0.0147(7) 0.0172(8) -0.0004(5) 0.0054(6) -0.0047(5) C14 0.0159(8) 0.0140(7) 0.0182(8) -0.0001(5) 0.0077(6) -0.0016(5) C15 0.0161(8) 0.0180(7) 0.0206(8) 0.0020(6) 0.0019(7) -0.0048(6) C27 0.0124(7) 0.0115(6) 0.0152(7) 0.0012(5) 0.0031(6) -0.0007(5) C17 0.0206(8) 0.0120(6) 0.0204(8) -0.0046(5) 0.0109(7) -0.0033(5) O11 0.0210(6) 0.0179(5) 0.0169(6) -0.0071(4) 0.0111(5) -0.0041(4) O12 0.0200(6) 0.0229(5) 0.0197(6) -0.0079(4) 0.0097(5) -0.0094(4) N11 0.0182(7) 0.0139(6) 0.0156(6) -0.0048(5) 0.0091(5) -0.0016(4) C12 0.0131(7) 0.0145(6) 0.0137(7) -0.0016(5) 0.0058(6) -0.0021(5) C11 0.0130(7) 0.0119(6) 0.0161(7) 0.0004(5) 0.0064(6) -0.0010(5) 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 111.89(12) 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 122.16(14) O13 C13 C14 123.89(13) O14 C13 C14 113.94(12) C26 C25 C24 112.40(12) C26 C25 H25A 109.1 C24 C25 H25A 109.1 C26 C25 H25B 109.1 C24 C25 H25B 109.1 H25A C25 H25B 107.9 O23 C23 O24 122.54(13) O23 C23 C24 123.56(15) O24 C23 C24 113.90(13) O22 C21 O21 125.25(15) O22 C21 C22 117.00(13) O21 C21 C22 117.75(13) C27 C26 C25 111.91(12) 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 112.47(13) 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 113.34(13) 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 111.18(13) 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 112.47(13) C16 C15 H15A 109.1 C14 C15 H15A 109.1 C16 C15 H15B 109.1 C14 C15 H15B 109.1 H15A C15 H15B 107.8 O25 C27 O26 119.09(13) O25 C27 C26 123.40(13) O26 C27 C26 117.50(13) O15 C17 O16 119.43(14) O15 C17 C16 123.68(14) O16 C17 C16 116.84(13) 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 111.46(12) 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(14) O11 C11 C12 117.59(13) O12 C11 C12 116.70(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O23 C23 1.2303(18) O25 C27 1.2150(19) O26 C27 1.3299(17) O26 H26 0.8400 O21 C21 1.2561(19) O22 C21 1.2561(18) O13 C13 1.2297(17) O24 C23 1.3069(19) O24 H24 0.8400 O16 C17 1.3315(19) O16 H16 0.8400 O14 C13 1.3122(18) O14 H14 0.8400 O15 C17 1.213(2) N21 C22 1.4820(19) N21 H21A 0.9100 N21 H21B 0.9100 N21 H21C 0.9100 C22 C21 1.523(2) C22 H22A 0.9900 C22 H22B 0.9900 C13 C14 1.501(2) C25 C26 1.5256(19) C25 C24 1.530(2) C25 H25A 0.9900 C25 H25B 0.9900 C23 C24 1.5073(19) C26 C27 1.506(2) C26 H26A 0.9900 C26 H26B 0.9900 C24 H24A 0.9900 C24 H24B 0.9900 C16 C17 1.508(2) C16 C15 1.522(2) C16 H16A 0.9900 C16 H16B 0.9900 C14 C15 1.534(2) C14 H14A 0.9900 C14 H14B 0.9900 C15 H15A 0.9900 C15 H15B 0.9900 O11 C11 1.2535(18) O12 C11 1.2549(18) N11 C12 1.4860(19) N11 H11A 0.9100 N11 H11B 0.9100 N11 H11C 0.9100 C12 C11 1.525(2) 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 2.5739(16) 175.1 O16 H16 O12 2_667 0.84 1.74 2.5644(16) 165.7 N11 H11A O15 . 0.91 2.13 2.8245(15) 132.5 N11 H11B O23 2_666 0.91 1.96 2.8537(18) 168.4 N11 H11C O23 . 0.91 2.09 2.9564(17) 158.6 O24 H24 O11 1_455 0.84 1.72 2.5623(14) 176.1 O26 H26 O22 2_676 0.84 1.73 2.5539(16) 167.0 N21 H21A O25 . 0.91 2.06 2.7956(17) 136.8 N21 H21B O13 2_667 0.91 1.95 2.8522(17) 172.2 N21 H21C O13 1_565 0.91 2.11 2.9639(17) 156.0 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 O22 177.84(12) N21 C22 C21 O21 -2.58(18) C24 C25 C26 C27 167.46(13) O23 C23 C24 C25 -142.69(16) O24 C23 C24 C25 37.30(19) C26 C25 C24 C23 178.60(13) O13 C13 C14 C15 97.45(17) O14 C13 C14 C15 -81.62(16) C17 C16 C15 C14 -74.23(17) C13 C14 C15 C16 176.32(13) C25 C26 C27 O25 -6.1(2) C25 C26 C27 O26 175.42(13) C15 C16 C17 O15 -4.1(2) C15 C16 C17 O16 178.32(13) N11 C12 C11 O11 -2.49(18) N11 C12 C11 O12 177.39(13) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654321 2 PubChem 139064066