#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105119.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_2105119 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 85.540(11) _cell_angle_beta 113.122(10) _cell_angle_gamma 88.270(11) _cell_formula_units_Z 4 _cell_length_a 4.9021(7) _cell_length_b 20.167(3) _cell_length_c 10.1686(15) _cell_measurement_reflns_used 7886 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.61 _cell_measurement_theta_min 2.07 _cell_volume 919.7(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 150(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.889 _diffrn_measured_fraction_theta_max 0.889 _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 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0685 _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 10066 _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 1.496 _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 0.214 _refine_diff_density_min -0.199 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 4417 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.883 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0392 _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^)+(0.0327P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.0767 _reflns_number_gt 2840 _reflns_number_total 4417 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.90210 20.16680 10.16860 85.54000 113.12200 88.27000 ZERR 4 0.00070 0.00290 0.00150 0.01100 0.01000 0.01100 LATT 1 SFAC C H N O UNIT 28 52 4 24 TEMP -123 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 0.032700 FVAR 0.75638 O23 4 0.187380 0.589143 0.450780 11.00000 0.02432 0.01607 = 0.02282 -0.00503 0.01119 -0.00293 O25 4 0.654562 0.848117 0.752419 11.00000 0.03210 0.01921 = 0.02130 -0.00539 0.01602 -0.00430 O26 4 0.854944 0.904756 0.624119 11.00000 0.03210 0.01923 = 0.02227 -0.00577 0.01505 -0.00878 AFIX 147 H26 2 0.875504 0.902825 0.546267 11.00000 -1.50000 AFIX 0 O21 4 0.127621 1.055513 0.824099 11.00000 0.02260 0.02120 = 0.01901 -0.00138 0.00997 0.00411 O22 4 0.007133 1.090626 0.593871 11.00000 0.02219 0.02671 = 0.02067 0.00467 0.01021 0.00512 O13 4 0.771573 0.087662 1.015068 11.00000 0.02159 0.01542 = 0.01985 -0.00037 0.00830 0.00023 O24 4 0.073728 0.654651 0.590165 11.00000 0.03391 0.01844 = 0.03286 -0.00901 0.02466 -0.01058 AFIX 147 H24 2 -0.005740 0.620406 0.606515 11.00000 -1.50000 AFIX 0 O16 4 0.180901 0.404388 0.908022 11.00000 0.03538 0.02083 = 0.02289 0.00112 0.01553 0.00773 AFIX 147 H16 2 0.170726 0.403956 0.988639 11.00000 -1.50000 AFIX 0 O14 4 0.788017 0.153466 0.832937 11.00000 0.03091 0.01998 = 0.02291 0.00351 0.01678 0.00711 AFIX 147 H14 2 0.887178 0.120078 0.826569 11.00000 -1.50000 AFIX 0 O15 4 0.403852 0.345468 0.802006 11.00000 0.04796 0.02007 = 0.03002 0.00101 0.02807 0.00204 N21 3 0.579342 0.971418 0.845837 11.00000 0.02047 0.01632 = 0.01793 -0.00172 0.00914 0.00304 AFIX 137 H21A 2 0.703662 0.939436 0.836443 11.00000 -1.50000 H21B 2 0.453129 0.951960 0.880731 11.00000 -1.50000 H21C 2 0.687937 1.000210 0.907637 11.00000 -1.50000 AFIX 0 C22 1 0.405431 1.008333 0.703551 11.00000 0.01647 0.01704 = 0.01592 -0.00255 0.00758 -0.00203 AFIX 23 H22A 2 0.315149 0.976088 0.632496 11.00000 -1.20000 H22B 2 0.540727 1.034260 0.671824 11.00000 -1.20000 AFIX 0 C13 1 0.698162 0.140324 0.937285 11.00000 0.01532 0.01511 = 0.01586 -0.00378 0.00473 -0.00267 C25 1 0.476756 0.745073 0.577498 11.00000 0.02052 0.01648 = 0.01626 -0.00368 0.00963 -0.00409 AFIX 23 H25A 2 0.330682 0.761342 0.614609 11.00000 -1.20000 H25B 2 0.632849 0.716443 0.656229 11.00000 -1.20000 AFIX 0 C23 1 0.188600 0.643615 0.497154 11.00000 0.01446 0.01743 = 0.01496 -0.00175 0.00455 -0.00134 C21 1 0.161061 1.055472 0.707776 11.00000 0.01509 0.01462 = 0.01822 -0.00288 0.00776 -0.00366 C26 1 0.617755 0.804487 0.533727 11.00000 0.02127 0.01607 = 0.01684 -0.00301 0.00953 -0.00314 AFIX 23 H26A 2 0.794066 0.788359 0.517807 11.00000 -1.20000 H26B 2 0.473840 0.827516 0.441946 11.00000 -1.20000 AFIX 0 C24 1 0.320524 0.703369 0.452895 11.00000 0.02493 0.01935 = 0.01778 -0.00471 0.01085 -0.00651 AFIX 23 H24A 2 0.160633 0.731672 0.375281 11.00000 -1.20000 H24B 2 0.465255 0.688164 0.413988 11.00000 -1.20000 AFIX 0 C16 1 0.498649 0.308348 1.047241 11.00000 0.02208 0.01621 = 0.02134 -0.00446 0.00717 -0.00011 AFIX 23 H16A 2 0.340197 0.291100 1.075249 11.00000 -1.20000 H16B 2 0.622990 0.335094 1.123724 11.00000 -1.20000 AFIX 0 C14 1 0.504120 0.195550 0.953136 11.00000 0.01901 0.01545 = 0.02230 -0.00270 0.00914 -0.00093 AFIX 23 H14A 2 0.383066 0.177081 1.003814 11.00000 -1.20000 H14B 2 0.366797 0.215525 0.856749 11.00000 -1.20000 AFIX 0 C15 1 0.690427 0.249675 1.037308 11.00000 0.01850 0.02062 = 0.02524 -0.00508 0.00254 0.00313 AFIX 23 H15A 2 0.819140 0.230065 1.135494 11.00000 -1.20000 H15B 2 0.820846 0.265922 0.989798 11.00000 -1.20000 AFIX 0 C27 1 0.710248 0.853181 0.645577 11.00000 0.01531 0.01277 = 0.01841 -0.00034 0.00563 0.00130 C17 1 0.357269 0.352937 0.908638 11.00000 0.02468 0.01427 = 0.02411 -0.00308 0.01389 -0.00385 O11 4 0.839194 0.551718 0.653684 11.00000 0.02427 0.02068 = 0.01985 -0.00433 0.01236 -0.00859 O12 4 0.938108 0.587011 0.869436 11.00000 0.02470 0.02605 = 0.02327 -0.01171 0.01235 -0.01033 N11 3 0.427454 0.470639 0.663030 11.00000 0.02141 0.01632 = 0.01853 -0.00218 0.01101 -0.00634 AFIX 137 H11A 2 0.313740 0.439941 0.683352 11.00000 -1.50000 H11B 2 0.565309 0.449683 0.638584 11.00000 -1.50000 H11C 2 0.309702 0.500197 0.588519 11.00000 -1.50000 AFIX 0 C12 1 0.579678 0.506568 0.790904 11.00000 0.01575 0.01763 = 0.01635 -0.00234 0.00777 -0.00150 AFIX 23 H12A 2 0.683730 0.473844 0.875309 11.00000 -1.20000 H12B 2 0.430076 0.533376 0.810751 11.00000 -1.20000 AFIX 0 C11 1 0.803463 0.552274 0.769152 11.00000 0.01360 0.01357 = 0.01848 -0.00089 0.00771 0.00112 HKLF 4 REM REM R1 = 0.0392 for 2840 Fo > 4sig(Fo) and 0.0816 for all 4417 data REM 259 parameters refined using 0 restraints END WGHT 0.0327 0.0000 REM Highest difference peak 0.214, deepest hole -0.199, 1-sigma level 0.044 Q1 1 0.6384 0.8288 0.5866 11.00000 0.05 0.21 Q2 1 0.5481 0.3488 0.8511 11.00000 0.05 0.17 Q3 1 0.5871 0.1688 0.9324 11.00000 0.05 0.16 Q4 1 0.0020 1.0833 0.8126 11.00000 0.05 0.16 Q5 1 0.5523 0.8769 0.8033 11.00000 0.05 0.16 Q6 1 0.2658 1.0231 0.7204 11.00000 0.05 0.16 Q7 1 0.3977 0.7274 0.4991 11.00000 0.05 0.16 Q8 1 0.4134 0.3311 0.9776 11.00000 0.05 0.16 Q9 1 0.4986 0.6493 0.4205 11.00000 0.05 0.16 Q10 1 0.9524 0.1981 0.8775 11.00000 0.05 0.15 Q11 1 0.5518 0.7820 0.5550 11.00000 0.05 0.15 Q12 1 0.8043 0.2182 0.8782 11.00000 0.05 0.15 Q13 1 0.5490 0.8262 0.7734 11.00000 0.05 0.15 Q14 1 0.6682 0.5349 0.7633 11.00000 0.05 0.15 Q15 1 0.4922 0.1529 1.0670 11.00000 0.05 0.15 Q16 1 0.7833 0.0892 0.7159 11.00000 0.05 0.15 Q17 1 0.7522 1.0472 0.9030 11.00000 0.05 0.14 Q18 1 0.7795 0.5855 0.5958 11.00000 0.05 0.14 Q19 1 -0.0869 1.0963 0.4831 11.00000 0.05 0.14 Q20 1 0.3080 0.3869 0.7349 11.00000 0.05 0.14 Q21 1 0.3493 0.1185 0.9802 11.00000 0.05 0.14 Q22 1 0.2596 0.2333 0.7499 11.00000 0.05 0.14 Q23 1 0.4117 0.1873 1.0898 11.00000 0.05 0.14 Q24 1 0.5023 0.0923 0.9592 11.00000 0.05 0.14 Q25 1 0.7248 0.5702 0.6804 11.00000 0.05 0.14 Q26 1 0.5804 0.2802 1.0219 11.00000 0.05 0.14 Q27 1 0.7683 0.4982 0.6001 11.00000 0.05 0.14 Q28 1 0.5730 0.2228 0.9881 11.00000 0.05 0.14 Q29 1 0.7448 0.3431 1.0974 11.00000 0.05 0.13 Q30 1 0.3462 0.2953 0.7444 11.00000 0.05 0.13 Q31 1 0.8569 0.2610 1.0567 11.00000 0.05 0.13 Q32 1 -0.0144 1.0544 0.5412 11.00000 0.05 0.13 Q33 1 0.2246 0.2011 0.6833 11.00000 0.05 0.13 Q34 1 0.3165 0.1466 1.0917 11.00000 0.05 0.13 Q35 1 0.2513 0.1804 0.7438 11.00000 0.05 0.13 Q36 1 0.5458 0.4519 0.9558 11.00000 0.05 0.13 Q37 1 0.8835 0.9420 0.6768 11.00000 0.05 0.13 Q38 1 0.4489 0.4008 0.5400 11.00000 0.05 0.13 Q39 1 0.2166 0.3136 0.6629 11.00000 0.05 0.13 Q40 1 0.4976 0.3169 0.7284 11.00000 0.05 0.13 Q41 1 0.6460 0.3721 0.8995 11.00000 0.05 0.13 Q42 1 0.6099 0.5843 0.6153 11.00000 0.05 0.13 Q43 1 1.1325 0.8610 0.7917 11.00000 0.05 0.13 Q44 1 0.3358 0.5671 0.5850 11.00000 0.05 0.13 Q45 1 0.7831 0.8762 0.8184 11.00000 0.05 0.13 Q46 1 0.7299 0.8345 0.8609 11.00000 0.05 0.13 Q47 1 0.4137 0.5524 0.8839 11.00000 0.05 0.13 Q48 1 0.7577 0.4035 0.9653 11.00000 0.05 0.13 Q49 1 -0.0348 0.5913 0.3520 11.00000 0.05 0.13 Q50 1 -0.2577 1.1017 0.5201 11.00000 0.05 0.13 Q51 1 1.0891 0.5029 0.9157 11.00000 0.05 0.13 Q52 1 0.9688 0.6186 0.8166 11.00000 0.05 0.13 Q53 1 0.7410 0.1389 1.1322 11.00000 0.05 0.12 Q54 1 0.7699 0.0693 0.8348 11.00000 0.05 0.12 Q55 1 1.1636 0.5682 0.9691 11.00000 0.05 0.12 Q56 1 0.8193 0.3603 1.1731 11.00000 0.05 0.12 Q57 1 1.1815 0.5877 0.8786 11.00000 0.05 0.12 Q58 1 0.2370 0.3013 0.7777 11.00000 0.05 0.12 Q59 1 0.9679 0.3280 1.1637 11.00000 0.05 0.12 Q60 1 0.2664 0.3420 0.6958 11.00000 0.05 0.12 Q61 1 0.1860 0.7815 0.5253 11.00000 0.05 0.12 Q62 1 0.6025 0.1260 0.7059 11.00000 0.05 0.12 Q63 1 0.7973 0.2024 0.7864 11.00000 0.05 0.12 Q64 1 0.8589 0.6488 0.7567 11.00000 0.05 0.12 Q65 1 1.3068 0.5937 0.9824 11.00000 0.05 0.12 Q66 1 -0.2289 1.0911 0.5994 11.00000 0.05 0.12 Q67 1 0.8605 1.0107 0.7550 11.00000 0.05 0.12 Q68 1 0.4276 0.5995 0.8207 11.00000 0.05 0.12 Q69 1 0.0905 0.6797 0.7101 11.00000 0.05 0.12 Q70 1 0.3461 0.8510 0.7986 11.00000 0.05 0.12 Q71 1 0.8317 0.0625 0.7995 11.00000 0.05 0.12 Q72 1 0.2890 1.0374 0.9064 11.00000 0.05 0.12 Q73 1 0.6545 0.1876 0.7611 11.00000 0.05 0.12 Q74 1 0.4904 0.7485 0.6630 11.00000 0.05 0.12 Q75 1 0.2283 0.5504 0.8063 11.00000 0.05 0.12 Q76 1 0.1542 0.6081 0.3361 11.00000 0.05 0.12 Q77 1 0.4462 0.3730 0.7618 11.00000 0.05 0.12 Q78 1 0.5103 1.1010 0.6407 11.00000 0.05 0.12 Q79 1 0.5533 0.6868 0.6386 11.00000 0.05 0.12 Q80 1 0.8046 0.1508 0.9212 11.00000 0.05 0.12 Q81 1 -0.0093 0.4137 0.7795 11.00000 0.05 0.11 Q82 1 0.6238 0.5292 0.9679 11.00000 0.05 0.11 Q83 1 -0.0621 1.0353 0.8722 11.00000 0.05 0.11 Q84 1 0.8104 0.7426 0.7166 11.00000 0.05 0.11 Q85 1 0.8322 0.9609 0.5851 11.00000 0.05 0.11 Q86 1 0.6313 0.3856 0.6349 11.00000 0.05 0.11 Q87 1 0.5822 0.0696 1.0137 11.00000 0.05 0.11 Q88 1 0.7967 0.6120 0.8373 11.00000 0.05 0.11 Q89 1 0.8474 0.4550 0.7558 11.00000 0.05 0.11 Q90 1 0.2692 0.6355 0.2937 11.00000 0.05 0.11 Q91 1 0.8157 0.2086 1.2443 11.00000 0.05 0.11 Q92 1 0.9650 0.9895 0.9223 11.00000 0.05 0.11 Q93 1 0.1569 0.4968 0.4796 11.00000 0.05 0.11 Q94 1 0.3012 0.2920 0.8367 11.00000 0.05 0.11 Q95 1 0.1816 1.0005 0.8667 11.00000 0.05 0.11 Q96 1 0.9490 0.5719 0.6064 11.00000 0.05 0.11 Q97 1 0.9158 0.8266 0.5247 11.00000 0.05 0.11 Q98 1 0.8083 0.1801 1.2380 11.00000 0.05 0.11 Q99 1 0.5103 0.3023 0.8381 11.00000 0.05 0.11 Q100 1 0.6946 0.2215 1.1479 11.00000 0.05 0.11 ; _cod_data_source_file gp5050.cif _cod_data_source_block 150 _cod_database_code 2105119 _cod_database_fobs_code 2105119 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 0.1874(3) 0.58914(5) 0.45078(12) 0.0203(3) Uani d . 1 O O25 0.6546(3) 0.84812(5) 0.75242(13) 0.0223(3) Uani d . 1 O O26 0.8549(3) 0.90476(5) 0.62412(13) 0.0228(3) Uani d . 1 H H26 0.8755 0.9028 0.5463 0.034 Uiso calc R 1 O O21 0.1276(3) 1.05551(5) 0.82410(12) 0.0206(2) Uani d . 1 O O22 0.0071(3) 1.09063(5) 0.59387(13) 0.0232(3) Uani d . 1 O O13 0.7716(3) 0.08766(5) 1.01507(12) 0.0190(2) Uani d . 1 O O24 0.0737(3) 0.65465(5) 0.59016(14) 0.0243(3) Uani d . 1 H H24 -0.0057 0.6204 0.6065 0.036 Uiso calc R 1 O O16 0.1809(3) 0.40439(5) 0.90802(13) 0.0255(3) Uani d . 1 H H16 0.1707 0.4040 0.9886 0.038 Uiso calc R 1 O O14 0.7880(3) 0.15347(5) 0.83294(13) 0.0232(3) Uani d . 1 H H14 0.8872 0.1201 0.8266 0.035 Uiso calc R 1 O O15 0.4039(3) 0.34547(5) 0.80201(14) 0.0290(3) Uani d . 1 N N21 0.5793(3) 0.97142(6) 0.84584(14) 0.0179(3) Uani d . 1 H H21A 0.7037 0.9394 0.8364 0.027 Uiso calc R 1 H H21B 0.4531 0.9520 0.8807 0.027 Uiso calc R 1 H H21C 0.6879 1.0002 0.9076 0.027 Uiso calc R 1 C C22 0.4054(4) 1.00833(7) 0.70355(17) 0.0160(3) Uani d . 1 H H22A 0.3151 0.9761 0.6325 0.019 Uiso calc R 1 H H22B 0.5407 1.0343 0.6718 0.019 Uiso calc R 1 C C13 0.6982(4) 0.14032(7) 0.93729(16) 0.0157(3) Uani d . 1 C C25 0.4768(4) 0.74507(7) 0.57750(17) 0.0168(3) Uani d . 1 H H25A 0.3307 0.7613 0.6146 0.020 Uiso calc R 1 H H25B 0.6328 0.7164 0.6562 0.020 Uiso calc R 1 C C23 0.1886(4) 0.64362(7) 0.49715(17) 0.0160(3) Uani d . 1 C C21 0.1611(4) 1.05547(7) 0.70778(17) 0.0155(3) Uani d . 1 C C26 0.6178(4) 0.80449(7) 0.53373(17) 0.0173(3) Uani d . 1 H H26A 0.7941 0.7884 0.5178 0.021 Uiso calc R 1 H H26B 0.4738 0.8275 0.4419 0.021 Uiso calc R 1 C C24 0.3205(4) 0.70337(7) 0.45289(18) 0.0197(3) Uani d . 1 H H24A 0.1606 0.7317 0.3753 0.024 Uiso calc R 1 H H24B 0.4653 0.6882 0.4140 0.024 Uiso calc R 1 C C16 0.4986(4) 0.30835(7) 1.04724(18) 0.0202(3) Uani d . 1 H H16A 0.3402 0.2911 1.0752 0.024 Uiso calc R 1 H H16B 0.6230 0.3351 1.1237 0.024 Uiso calc R 1 C C14 0.5041(4) 0.19555(7) 0.95314(18) 0.0186(3) Uani d . 1 H H14A 0.3831 0.1771 1.0038 0.022 Uiso calc R 1 H H14B 0.3668 0.2155 0.8567 0.022 Uiso calc R 1 C C15 0.6904(4) 0.24967(8) 1.03731(19) 0.0233(4) Uani d . 1 H H15A 0.8191 0.2301 1.1355 0.028 Uiso calc R 1 H H15B 0.8208 0.2659 0.9898 0.028 Uiso calc R 1 C C27 0.7102(4) 0.85318(7) 0.64558(17) 0.0159(3) Uani d . 1 C C17 0.3573(4) 0.35294(7) 0.90864(18) 0.0196(3) Uani d . 1 O O11 0.8392(3) 0.55172(5) 0.65368(12) 0.0202(2) Uani d . 1 O O12 0.9381(3) 0.58701(5) 0.86944(13) 0.0231(3) Uani d . 1 N N11 0.4275(3) 0.47064(6) 0.66303(14) 0.0176(3) Uani d . 1 H H11A 0.3137 0.4399 0.6834 0.026 Uiso calc R 1 H H11B 0.5653 0.4497 0.6386 0.026 Uiso calc R 1 H H11C 0.3097 0.5002 0.5885 0.026 Uiso calc R 1 C C12 0.5797(4) 0.50657(7) 0.79090(17) 0.0161(3) Uani d . 1 H H12A 0.6837 0.4738 0.8753 0.019 Uiso calc R 1 H H12B 0.4301 0.5334 0.8108 0.019 Uiso calc R 1 C C11 0.8035(3) 0.55227(7) 0.76915(17) 0.0149(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 0.0243(7) 0.0161(5) 0.0228(6) -0.0029(4) 0.0112(5) -0.0050(4) O25 0.0321(7) 0.0192(5) 0.0213(6) -0.0043(5) 0.0160(6) -0.0054(4) O26 0.0321(7) 0.0192(5) 0.0223(6) -0.0088(5) 0.0151(6) -0.0058(4) O21 0.0226(6) 0.0212(5) 0.0190(6) 0.0041(4) 0.0100(5) -0.0014(4) O22 0.0222(7) 0.0267(6) 0.0207(6) 0.0051(5) 0.0102(5) 0.0047(4) O13 0.0216(6) 0.0154(5) 0.0199(6) 0.0002(4) 0.0083(5) -0.0004(4) O24 0.0339(7) 0.0184(5) 0.0329(7) -0.0106(5) 0.0247(6) -0.0090(5) O16 0.0354(8) 0.0208(6) 0.0229(7) 0.0077(5) 0.0155(6) 0.0011(4) O14 0.0309(7) 0.0200(5) 0.0229(6) 0.0071(5) 0.0168(6) 0.0035(4) O15 0.0480(9) 0.0201(6) 0.0300(7) 0.0020(5) 0.0281(7) 0.0010(5) N21 0.0205(7) 0.0163(6) 0.0179(7) 0.0030(5) 0.0091(6) -0.0017(5) C22 0.0165(8) 0.0170(7) 0.0159(7) -0.0020(5) 0.0076(6) -0.0025(5) C13 0.0153(8) 0.0151(7) 0.0159(8) -0.0027(6) 0.0047(7) -0.0038(5) C25 0.0205(8) 0.0165(7) 0.0163(8) -0.0041(6) 0.0096(7) -0.0037(5) C23 0.0145(8) 0.0174(7) 0.0150(8) -0.0013(5) 0.0046(6) -0.0017(5) C21 0.0151(8) 0.0146(7) 0.0182(8) -0.0037(5) 0.0078(6) -0.0029(5) C26 0.0213(8) 0.0161(7) 0.0168(8) -0.0031(6) 0.0095(7) -0.0030(5) C24 0.0249(9) 0.0193(7) 0.0178(8) -0.0065(6) 0.0108(7) -0.0047(6) C16 0.0221(9) 0.0162(7) 0.0213(8) -0.0001(6) 0.0072(7) -0.0045(6) C14 0.0190(8) 0.0155(7) 0.0223(8) -0.0009(6) 0.0091(7) -0.0027(6) C15 0.0185(9) 0.0206(8) 0.0252(9) 0.0031(6) 0.0025(7) -0.0051(6) C27 0.0153(8) 0.0128(7) 0.0184(8) 0.0013(5) 0.0056(6) -0.0003(5) C17 0.0247(9) 0.0143(7) 0.0241(9) -0.0038(6) 0.0139(7) -0.0031(6) O11 0.0243(7) 0.0207(5) 0.0199(6) -0.0086(4) 0.0124(5) -0.0043(4) O12 0.0247(7) 0.0261(6) 0.0233(6) -0.0103(5) 0.0123(5) -0.0117(4) N11 0.0214(7) 0.0163(6) 0.0185(7) -0.0063(5) 0.0110(6) -0.0022(5) C12 0.0157(8) 0.0176(7) 0.0164(7) -0.0015(6) 0.0078(6) -0.0023(5) C11 0.0136(8) 0.0136(7) 0.0185(8) 0.0011(5) 0.0077(6) -0.0009(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 111.96(13) 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 122.15(14) O13 C13 C14 123.87(14) O14 C13 C14 113.97(12) C26 C25 C24 112.64(13) C26 C25 H25A 109.1 C24 C25 H25A 109.1 C26 C25 H25B 109.1 C24 C25 H25B 109.1 H25A C25 H25B 107.8 O23 C23 O24 122.42(13) O23 C23 C24 123.66(15) O24 C23 C24 113.92(13) O22 C21 O21 125.27(15) O22 C21 C22 117.00(14) O21 C21 C22 117.72(13) C27 C26 C25 112.15(13) 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 112.62(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 113.27(14) 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 111.24(14) 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 112.36(14) C16 C15 H15A 109.1 C14 C15 H15A 109.1 C16 C15 H15B 109.1 C14 C15 H15B 109.1 H15A C15 H15B 107.9 O25 C27 O26 119.01(14) O25 C27 C26 123.29(13) O26 C27 C26 117.69(14) O15 C17 O16 119.42(14) O15 C17 C16 123.78(15) O16 C17 C16 116.75(14) 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 111.57(13) 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 125.60(14) O11 C11 C12 117.52(13) O12 C11 C12 116.87(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O23 C23 1.2280(18) O25 C27 1.2176(19) O26 C27 1.3279(18) O26 H26 0.8400 O21 C21 1.2563(19) O22 C21 1.2518(19) O13 C13 1.2271(17) O24 C23 1.3056(19) O24 H24 0.8400 O16 C17 1.328(2) O16 H16 0.8400 O14 C13 1.3117(19) O14 H14 0.8400 O15 C17 1.212(2) N21 C22 1.483(2) 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 1.502(2) C25 C26 1.523(2) C25 C24 1.530(2) C25 H25A 0.9900 C25 H25B 0.9900 C23 C24 1.505(2) C26 C27 1.503(2) C26 H26A 0.9900 C26 H26B 0.9900 C24 H24A 0.9900 C24 H24B 0.9900 C16 C17 1.508(2) C16 C15 1.523(2) C16 H16A 0.9900 C16 H16B 0.9900 C14 C15 1.533(2) C14 H14A 0.9900 C14 H14B 0.9900 C15 H15A 0.9900 C15 H15B 0.9900 O11 C11 1.2541(19) O12 C11 1.2557(19) N11 C12 1.480(2) N11 H11A 0.9100 N11 H11B 0.9100 N11 H11C 0.9100 C12 C11 1.524(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 2.5745(16) 173.6 O16 H16 O12 2_667 0.84 1.74 2.5658(17) 165.6 N11 H11A O15 . 0.91 2.11 2.8238(16) 134.5 N11 H11B O23 2_666 0.91 1.96 2.8554(18) 169.3 N11 H11C O23 . 0.91 2.10 2.9644(17) 157.5 O24 H24 O11 1_455 0.84 1.72 2.5626(14) 175.5 O26 H26 O22 2_676 0.84 1.73 2.5550(16) 166.1 N21 H21A O25 . 0.91 2.07 2.7944(17) 135.6 N21 H21B O13 2_667 0.91 1.95 2.8551(17) 171.1 N21 H21C O13 1_565 0.91 2.11 2.9719(18) 157.0 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 177.79(13) N21 C22 C21 O21 -2.99(18) C24 C25 C26 C27 167.31(14) O23 C23 C24 C25 -142.48(16) O24 C23 C24 C25 37.6(2) C26 C25 C24 C23 178.41(14) O13 C13 C14 C15 97.87(18) O14 C13 C14 C15 -81.22(17) C17 C16 C15 C14 -74.51(18) C13 C14 C15 C16 176.54(14) C25 C26 C27 O25 -5.9(2) C25 C26 C27 O26 175.38(14) C15 C16 C17 O15 -4.0(2) C15 C16 C17 O16 178.47(14) N11 C12 C11 O11 -2.93(19) N11 C12 C11 O12 177.57(13) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654321 2 PubChem 139064066