#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105118.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_2105118 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 85.571(13) _cell_angle_beta 113.118(10) _cell_angle_gamma 88.306(12) _cell_formula_units_Z 4 _cell_length_a 4.9098(7) _cell_length_b 20.194(3) _cell_length_c 10.1777(15) _cell_measurement_reflns_used 7461 _cell_measurement_temperature 175(2) _cell_measurement_theta_max 29.56 _cell_measurement_theta_min 2.05 _cell_volume 923.3(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 175(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 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0917 _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 9568 _diffrn_reflns_theta_full 29.22 _diffrn_reflns_theta_max 29.22 _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 1.490 _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 0.221 _refine_diff_density_min -0.234 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 4319 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.889 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0487 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.0881 _reflns_number_gt 2580 _reflns_number_total 4319 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.90980 20.19440 10.17770 85.57100 113.11800 88.30600 ZERR 4 0.00070 0.00310 0.00150 0.01300 0.01000 0.01200 LATT 1 SFAC C H N O UNIT 28 52 4 24 TEMP -98 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 0.032900 FVAR 0.75397 O23 4 0.186997 0.588984 0.451138 11.00000 0.02761 0.01547 = 0.02655 -0.00618 0.01284 -0.00378 O25 4 0.653172 0.848105 0.751562 11.00000 0.03640 0.02074 = 0.02440 -0.00741 0.01829 -0.00619 O26 4 0.853719 0.904325 0.623318 11.00000 0.03460 0.02130 = 0.02448 -0.00652 0.01509 -0.01031 AFIX 147 H26 2 0.873069 0.902337 0.545270 11.00000 -1.50000 AFIX 0 O21 4 0.128010 1.055365 0.823971 11.00000 0.02722 0.02305 = 0.02170 -0.00141 0.01300 0.00571 O22 4 0.010227 1.090915 0.594712 11.00000 0.02588 0.02857 = 0.02468 0.00656 0.01254 0.00730 O13 4 0.772109 0.087621 1.014787 11.00000 0.02332 0.01589 = 0.02223 -0.00007 0.00893 0.00009 O24 4 0.073068 0.654627 0.590039 11.00000 0.03940 0.01941 = 0.03703 -0.00971 0.02862 -0.01214 AFIX 147 H24 2 0.001087 0.619874 0.609632 11.00000 -1.50000 AFIX 0 O16 4 0.182495 0.404138 0.908579 11.00000 0.03810 0.02254 = 0.02536 0.00183 0.01601 0.00854 AFIX 147 H16 2 0.171399 0.403576 0.988938 11.00000 -1.50000 AFIX 0 O14 4 0.790210 0.153540 0.833520 11.00000 0.03392 0.02207 = 0.02686 0.00411 0.01866 0.00893 AFIX 147 H14 2 0.895899 0.120885 0.829638 11.00000 -1.50000 AFIX 0 O15 4 0.404987 0.345529 0.802421 11.00000 0.05437 0.02149 = 0.03303 0.00180 0.03087 0.00284 N21 3 0.578346 0.971363 0.845763 11.00000 0.02394 0.01651 = 0.01994 -0.00193 0.01131 0.00237 AFIX 137 H21A 2 0.699897 0.938977 0.835899 11.00000 -1.50000 H21B 2 0.452452 0.952507 0.881473 11.00000 -1.50000 H21C 2 0.689487 0.999989 0.907050 11.00000 -1.50000 AFIX 0 C22 1 0.404438 1.008189 0.703882 11.00000 0.01718 0.01876 = 0.01669 -0.00279 0.00704 -0.00252 AFIX 23 H22A 2 0.313458 0.975977 0.632971 11.00000 -1.20000 H22B 2 0.539504 1.033950 0.671901 11.00000 -1.20000 AFIX 0 C13 1 0.699109 0.140258 0.937185 11.00000 0.01722 0.01587 = 0.01759 -0.00361 0.00711 -0.00300 C25 1 0.474436 0.744959 0.577427 11.00000 0.01975 0.01871 = 0.01946 -0.00238 0.00876 -0.00395 AFIX 23 H25A 2 0.328344 0.761196 0.614355 11.00000 -1.20000 H25B 2 0.630397 0.716471 0.656131 11.00000 -1.20000 AFIX 0 C23 1 0.187858 0.643424 0.497345 11.00000 0.01736 0.01840 = 0.01613 -0.00080 0.00645 -0.00179 C21 1 0.161807 1.055364 0.708296 11.00000 0.01643 0.01582 = 0.02196 -0.00358 0.00996 -0.00441 C26 1 0.614876 0.804397 0.532802 11.00000 0.02192 0.01656 = 0.01786 -0.00410 0.00943 -0.00264 AFIX 23 H26A 2 0.790226 0.788303 0.516335 11.00000 -1.20000 H26B 2 0.470445 0.827392 0.441367 11.00000 -1.20000 AFIX 0 C24 1 0.318908 0.703273 0.452340 11.00000 0.02542 0.02015 = 0.01961 -0.00550 0.01205 -0.00695 AFIX 23 H24A 2 0.159000 0.731423 0.374807 11.00000 -1.20000 H24B 2 0.463631 0.688167 0.413534 11.00000 -1.20000 AFIX 0 C16 1 0.499711 0.308202 1.047116 11.00000 0.02166 0.01851 = 0.02027 -0.00517 0.00425 0.00005 AFIX 23 H16A 2 0.341344 0.290739 1.074700 11.00000 -1.20000 H16B 2 0.622909 0.334941 1.123784 11.00000 -1.20000 AFIX 0 C14 1 0.506406 0.195357 0.953305 11.00000 0.01992 0.01734 = 0.02498 -0.00349 0.01079 -0.00092 AFIX 23 H14A 2 0.385901 0.176948 1.004173 11.00000 -1.20000 H14B 2 0.368946 0.215255 0.857091 11.00000 -1.20000 AFIX 0 C15 1 0.693251 0.249631 1.037409 11.00000 0.02109 0.02234 = 0.02618 -0.00599 0.00306 0.00447 AFIX 23 H15A 2 0.822133 0.230181 1.135504 11.00000 -1.20000 H15B 2 0.822929 0.265945 0.989704 11.00000 -1.20000 AFIX 0 C27 1 0.708576 0.853012 0.645082 11.00000 0.01590 0.01466 = 0.01920 -0.00048 0.00522 0.00199 C17 1 0.359045 0.352704 0.909201 11.00000 0.02351 0.01547 = 0.02504 -0.00274 0.01279 -0.00397 O11 4 0.839093 0.551650 0.653704 11.00000 0.02780 0.02262 = 0.02169 -0.00507 0.01436 -0.01009 O12 4 0.935849 0.587296 0.868807 11.00000 0.02777 0.02936 = 0.02586 -0.01407 0.01362 -0.01257 N11 3 0.427689 0.470528 0.663056 11.00000 0.02333 0.01713 = 0.01923 -0.00246 0.01161 -0.00690 AFIX 137 H11A 2 0.311697 0.440388 0.682990 11.00000 -1.50000 H11B 2 0.565196 0.448988 0.639522 11.00000 -1.50000 H11C 2 0.312555 0.500079 0.588167 11.00000 -1.50000 AFIX 0 C12 1 0.580297 0.506600 0.791004 11.00000 0.01642 0.01858 = 0.01573 -0.00178 0.00745 -0.00159 AFIX 23 H12A 2 0.684842 0.474000 0.875315 11.00000 -1.20000 H12B 2 0.431098 0.533304 0.811057 11.00000 -1.20000 AFIX 0 C11 1 0.803056 0.552384 0.768617 11.00000 0.01643 0.01432 = 0.02087 -0.00034 0.00915 0.00074 HKLF 4 REM REM R1 = 0.0487 for 2580 Fo > 4sig(Fo) and 0.1078 for all 4319 data REM 259 parameters refined using 0 restraints END WGHT 0.0329 0.0000 REM Highest difference peak 0.221, deepest hole -0.234, 1-sigma level 0.051 Q1 1 0.6848 0.5303 0.7710 11.00000 0.05 0.22 Q2 1 0.3164 0.8610 0.7518 11.00000 0.05 0.19 Q3 1 0.5756 0.3974 0.6199 11.00000 0.05 0.18 Q4 1 0.7728 0.8788 0.8169 11.00000 0.05 0.18 Q5 1 0.5822 0.6421 0.4531 11.00000 0.05 0.18 Q6 1 0.6607 0.8223 0.6004 11.00000 0.05 0.18 Q7 1 0.5409 0.5938 0.6057 11.00000 0.05 0.18 Q8 1 1.0015 0.0952 0.7980 11.00000 0.05 0.18 Q9 1 0.3360 0.6625 0.4627 11.00000 0.05 0.18 Q10 1 0.6087 0.1813 0.9284 11.00000 0.05 0.18 Q11 1 0.7252 0.1477 1.1219 11.00000 0.05 0.18 Q12 1 0.2341 1.0219 0.7016 11.00000 0.05 0.17 Q13 1 0.8773 0.6030 0.7883 11.00000 0.05 0.17 Q14 1 0.2999 0.6814 0.5183 11.00000 0.05 0.17 Q15 1 0.5376 0.8231 0.8225 11.00000 0.05 0.17 Q16 1 0.3560 0.2337 0.8977 11.00000 0.05 0.17 Q17 1 0.4147 0.9283 0.9672 11.00000 0.05 0.17 Q18 1 0.3639 0.3263 0.9777 11.00000 0.05 0.17 Q19 1 0.1064 0.5558 0.4985 11.00000 0.05 0.17 Q20 1 0.8463 0.3256 0.9334 11.00000 0.05 0.17 Q21 1 0.1095 0.4206 0.5630 11.00000 0.05 0.17 Q22 1 0.8076 0.5819 0.5841 11.00000 0.05 0.17 Q23 1 0.8673 0.5288 0.5426 11.00000 0.05 0.17 Q24 1 0.5065 0.1804 1.1262 11.00000 0.05 0.16 Q25 1 0.1491 0.8203 0.6806 11.00000 0.05 0.16 Q26 1 0.5126 0.1575 1.0660 11.00000 0.05 0.16 Q27 1 0.9482 0.9694 0.8895 11.00000 0.05 0.16 Q28 1 0.9657 0.1486 1.1657 11.00000 0.05 0.16 Q29 1 0.8306 0.9431 0.6995 11.00000 0.05 0.16 Q30 1 0.5710 0.5502 0.5805 11.00000 0.05 0.16 Q31 1 0.9148 0.3213 1.1330 11.00000 0.05 0.16 Q32 1 0.9956 0.5016 0.6642 11.00000 0.05 0.16 Q33 1 0.5256 0.7699 0.5487 11.00000 0.05 0.15 Q34 1 0.2764 0.2125 0.7022 11.00000 0.05 0.15 Q35 1 0.5737 0.2231 0.9859 11.00000 0.05 0.15 Q36 1 0.5784 0.5812 0.5425 11.00000 0.05 0.15 Q37 1 0.7083 0.6777 0.6817 11.00000 0.05 0.15 Q38 1 0.0877 0.5287 0.5361 11.00000 0.05 0.15 Q39 1 0.8119 0.6085 0.8738 11.00000 0.05 0.15 Q40 1 0.5723 0.5153 0.9644 11.00000 0.05 0.15 Q41 1 0.4557 0.1017 0.8348 11.00000 0.05 0.15 Q42 1 0.2442 0.3095 1.0425 11.00000 0.05 0.15 Q43 1 0.8859 0.1946 0.8494 11.00000 0.05 0.15 Q44 1 1.1856 0.2286 1.1695 11.00000 0.05 0.15 Q45 1 0.8701 0.2922 1.2043 11.00000 0.05 0.15 Q46 1 0.3089 0.5672 0.5679 11.00000 0.05 0.15 Q47 1 0.5396 0.3278 0.7402 11.00000 0.05 0.15 Q48 1 0.3777 0.6008 0.8284 11.00000 0.05 0.15 Q49 1 0.3957 0.3357 1.1854 11.00000 0.05 0.15 Q50 1 0.1840 0.6912 0.7206 11.00000 0.05 0.15 Q51 1 0.1633 1.0843 0.8921 11.00000 0.05 0.15 Q52 1 0.3166 0.3811 0.7230 11.00000 0.05 0.15 Q53 1 0.7283 0.5712 0.6856 11.00000 0.05 0.14 Q54 1 0.6809 0.3470 0.8381 11.00000 0.05 0.14 Q55 1 0.4692 0.6880 0.6397 11.00000 0.05 0.14 Q56 1 0.4715 0.4476 0.9198 11.00000 0.05 0.14 Q57 1 0.3294 0.8100 0.7419 11.00000 0.05 0.14 Q58 1 0.6190 0.8892 0.7141 11.00000 0.05 0.14 Q59 1 0.9247 0.2689 0.8363 11.00000 0.05 0.14 Q60 1 0.2324 0.8069 0.5954 11.00000 0.05 0.14 Q61 1 1.1534 0.5566 0.9565 11.00000 0.05 0.14 Q62 1 0.6125 0.7613 0.7493 11.00000 0.05 0.14 Q63 1 0.6451 0.1406 0.8462 11.00000 0.05 0.14 Q64 1 0.5666 0.2840 1.0145 11.00000 0.05 0.14 Q65 1 0.4207 0.9710 0.9510 11.00000 0.05 0.14 Q66 1 0.3889 0.7289 0.4989 11.00000 0.05 0.14 Q67 1 0.4654 0.4204 0.8047 11.00000 0.05 0.14 Q68 1 0.7954 0.7277 0.4978 11.00000 0.05 0.14 Q69 1 0.0810 1.0003 0.4819 11.00000 0.05 0.14 Q70 1 0.1919 0.5080 0.4301 11.00000 0.05 0.14 Q71 1 0.6581 1.0133 0.5653 11.00000 0.05 0.14 Q72 1 0.6479 0.6581 0.7651 11.00000 0.05 0.14 Q73 1 0.4986 0.8829 0.8782 11.00000 0.05 0.14 Q74 1 0.1900 0.2184 0.7895 11.00000 0.05 0.14 Q75 1 0.7206 0.6273 0.7153 11.00000 0.05 0.14 Q76 1 0.7811 0.5040 0.6323 11.00000 0.05 0.14 Q77 1 0.0107 0.7023 0.5950 11.00000 0.05 0.14 Q78 1 0.3449 0.8748 0.4093 11.00000 0.05 0.14 Q79 1 0.8824 0.9428 1.0076 11.00000 0.05 0.14 Q80 1 0.5802 0.8006 0.7564 11.00000 0.05 0.14 Q81 1 0.0644 1.0428 0.7401 11.00000 0.05 0.13 Q82 1 0.2316 0.7005 0.6219 11.00000 0.05 0.13 Q83 1 0.3567 0.5617 0.8393 11.00000 0.05 0.13 Q84 1 0.4486 0.7906 0.5985 11.00000 0.05 0.13 Q85 1 -0.2144 1.1000 0.6144 11.00000 0.05 0.13 Q86 1 0.5860 0.9768 1.0376 11.00000 0.05 0.13 Q87 1 0.0340 0.7482 0.4731 11.00000 0.05 0.13 Q88 1 0.0461 0.5580 0.5608 11.00000 0.05 0.13 Q89 1 0.0737 0.1762 0.9679 11.00000 0.05 0.13 Q90 1 -0.0683 0.3658 0.8511 11.00000 0.05 0.13 Q91 1 0.6135 0.9317 0.7176 11.00000 0.05 0.13 Q92 1 0.6870 0.1855 1.1987 11.00000 0.05 0.13 Q93 1 0.6339 0.0743 0.9199 11.00000 0.05 0.13 Q94 1 0.9633 0.8063 0.6071 11.00000 0.05 0.13 Q95 1 0.8758 0.8198 0.7625 11.00000 0.05 0.13 Q96 1 0.2571 0.6422 0.6058 11.00000 0.05 0.13 Q97 1 0.5641 0.8267 0.3235 11.00000 0.05 0.13 Q98 1 0.7194 0.8971 0.9201 11.00000 0.05 0.13 Q99 1 0.7209 1.0660 0.8584 11.00000 0.05 0.13 Q100 1 0.2459 0.7716 0.5344 11.00000 0.05 0.13 ; _cod_data_source_file gp5050.cif _cod_data_source_block 175 _cod_database_code 2105118 _cod_database_fobs_code 2105118 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 0.1870(4) 0.58898(6) 0.45114(16) 0.0223(3) Uani d . 1 O O25 0.6532(4) 0.84810(6) 0.75156(17) 0.0248(3) Uani d . 1 O O26 0.8537(4) 0.90432(6) 0.62332(17) 0.0253(4) Uani d . 1 H H26 0.8731 0.9023 0.5453 0.038 Uiso calc R 1 O O21 0.1280(4) 1.05536(6) 0.82397(16) 0.0232(3) Uani d . 1 O O22 0.0102(4) 1.09092(7) 0.59471(17) 0.0263(4) Uani d . 1 O O13 0.7721(3) 0.08762(6) 1.01479(16) 0.0206(3) Uani d . 1 O O24 0.0731(4) 0.65463(6) 0.59004(18) 0.0271(4) Uani d . 1 H H24 0.0011 0.6199 0.6096 0.041 Uiso calc R 1 O O16 0.1825(4) 0.40414(7) 0.90858(17) 0.0281(4) Uani d . 1 H H16 0.1714 0.4036 0.9889 0.042 Uiso calc R 1 O O14 0.7902(4) 0.15354(7) 0.83352(17) 0.0262(4) Uani d . 1 H H14 0.8959 0.1209 0.8296 0.039 Uiso calc R 1 O O15 0.4050(4) 0.34553(7) 0.80242(18) 0.0324(4) Uani d . 1 N N21 0.5783(4) 0.97136(7) 0.84576(19) 0.0194(4) Uani d . 1 H H21A 0.6999 0.9390 0.8359 0.029 Uiso calc R 1 H H21B 0.4525 0.9525 0.8815 0.029 Uiso calc R 1 H H21C 0.6895 1.0000 0.9071 0.029 Uiso calc R 1 C C22 0.4044(5) 1.00819(9) 0.7039(2) 0.0174(4) Uani d . 1 H H22A 0.3135 0.9760 0.6330 0.021 Uiso calc R 1 H H22B 0.5395 1.0340 0.6719 0.021 Uiso calc R 1 C C13 0.6991(5) 0.14026(9) 0.9372(2) 0.0167(4) Uani d . 1 C C25 0.4744(5) 0.74496(9) 0.5774(2) 0.0189(4) Uani d . 1 H H25A 0.3283 0.7612 0.6144 0.023 Uiso calc R 1 H H25B 0.6304 0.7165 0.6561 0.023 Uiso calc R 1 C C23 0.1879(5) 0.64342(9) 0.4973(2) 0.0174(4) Uani d . 1 C C21 0.1618(5) 1.05536(9) 0.7083(2) 0.0172(4) Uani d . 1 C C26 0.6149(5) 0.80440(9) 0.5328(2) 0.0181(4) Uani d . 1 H H26A 0.7902 0.7883 0.5163 0.022 Uiso calc R 1 H H26B 0.4704 0.8274 0.4414 0.022 Uiso calc R 1 C C24 0.3189(5) 0.70327(9) 0.4523(2) 0.0204(4) Uani d . 1 H H24A 0.1590 0.7314 0.3748 0.025 Uiso calc R 1 H H24B 0.4636 0.6882 0.4135 0.025 Uiso calc R 1 C C16 0.4997(5) 0.30820(9) 1.0471(2) 0.0213(4) Uani d . 1 H H16A 0.3413 0.2907 1.0747 0.026 Uiso calc R 1 H H16B 0.6229 0.3349 1.1238 0.026 Uiso calc R 1 C C14 0.5064(5) 0.19536(9) 0.9533(2) 0.0201(4) Uani d . 1 H H14A 0.3859 0.1769 1.0042 0.024 Uiso calc R 1 H H14B 0.3689 0.2153 0.8571 0.024 Uiso calc R 1 C C15 0.6933(5) 0.24963(9) 1.0374(2) 0.0251(5) Uani d . 1 H H15A 0.8221 0.2302 1.1355 0.030 Uiso calc R 1 H H15B 0.8229 0.2659 0.9897 0.030 Uiso calc R 1 C C27 0.7086(5) 0.85301(8) 0.6451(2) 0.0173(4) Uani d . 1 C C17 0.3590(5) 0.35270(9) 0.9092(2) 0.0202(4) Uani d . 1 O O11 0.8391(3) 0.55165(6) 0.65370(16) 0.0223(3) Uani d . 1 O O12 0.9358(4) 0.58730(7) 0.86881(17) 0.0259(4) Uani d . 1 N N11 0.4277(4) 0.47053(7) 0.66306(18) 0.0187(4) Uani d . 1 H H11A 0.3117 0.4404 0.6830 0.028 Uiso calc R 1 H H11B 0.5652 0.4490 0.6395 0.028 Uiso calc R 1 H H11C 0.3126 0.5001 0.5882 0.028 Uiso calc R 1 C C12 0.5803(5) 0.50660(9) 0.7910(2) 0.0166(4) Uani d . 1 H H12A 0.6848 0.4740 0.8753 0.020 Uiso calc R 1 H H12B 0.4311 0.5333 0.8111 0.020 Uiso calc R 1 C C11 0.8031(5) 0.55238(8) 0.7686(2) 0.0168(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 0.0276(9) 0.0155(7) 0.0266(9) -0.0038(6) 0.0128(7) -0.0062(5) O25 0.0364(10) 0.0207(7) 0.0244(9) -0.0062(6) 0.0183(8) -0.0074(5) O26 0.0346(10) 0.0213(7) 0.0245(9) -0.0103(6) 0.0151(8) -0.0065(6) O21 0.0272(9) 0.0230(7) 0.0217(8) 0.0057(6) 0.0130(7) -0.0014(6) O22 0.0259(9) 0.0286(8) 0.0247(9) 0.0073(6) 0.0125(7) 0.0066(6) O13 0.0233(9) 0.0159(6) 0.0222(8) 0.0001(5) 0.0089(7) -0.0001(5) O24 0.0394(10) 0.0194(7) 0.0370(10) -0.0121(7) 0.0286(9) -0.0097(6) O16 0.0381(11) 0.0225(7) 0.0254(9) 0.0085(6) 0.0160(8) 0.0018(6) O14 0.0339(10) 0.0221(7) 0.0269(9) 0.0089(6) 0.0187(8) 0.0041(6) O15 0.0544(12) 0.0215(7) 0.0330(10) 0.0028(7) 0.0309(9) 0.0018(6) N21 0.0239(10) 0.0165(8) 0.0199(9) 0.0024(6) 0.0113(8) -0.0019(6) C22 0.0172(11) 0.0188(9) 0.0167(10) -0.0025(7) 0.0070(8) -0.0028(7) C13 0.0172(11) 0.0159(8) 0.0176(11) -0.0030(7) 0.0071(9) -0.0036(7) C25 0.0197(11) 0.0187(9) 0.0195(10) -0.0039(7) 0.0088(9) -0.0024(7) C23 0.0174(11) 0.0184(9) 0.0161(10) -0.0018(7) 0.0065(9) -0.0008(7) C21 0.0164(11) 0.0158(9) 0.0220(11) -0.0044(7) 0.0100(9) -0.0036(7) C26 0.0219(11) 0.0166(9) 0.0179(10) -0.0026(7) 0.0094(9) -0.0041(7) C24 0.0254(12) 0.0201(9) 0.0196(11) -0.0070(8) 0.0120(10) -0.0055(7) C16 0.0217(12) 0.0185(9) 0.0203(11) 0.0000(8) 0.0043(9) -0.0052(7) C14 0.0199(11) 0.0173(9) 0.0250(11) -0.0009(7) 0.0108(9) -0.0035(7) C15 0.0211(12) 0.0223(10) 0.0262(12) 0.0045(8) 0.0031(10) -0.0060(8) C27 0.0159(10) 0.0147(8) 0.0192(11) 0.0020(7) 0.0052(9) -0.0005(7) C17 0.0235(12) 0.0155(9) 0.0250(12) -0.0040(8) 0.0128(10) -0.0027(7) O11 0.0278(9) 0.0226(7) 0.0217(8) -0.0101(6) 0.0144(7) -0.0051(5) O12 0.0278(9) 0.0294(8) 0.0259(9) -0.0126(6) 0.0136(7) -0.0141(6) N11 0.0233(10) 0.0171(8) 0.0192(9) -0.0069(7) 0.0116(8) -0.0025(6) C12 0.0164(11) 0.0186(9) 0.0157(10) -0.0016(7) 0.0075(8) -0.0018(7) C11 0.0164(10) 0.0143(8) 0.0209(11) 0.0007(7) 0.0091(9) -0.0003(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 112.08(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 122.14(18) O13 C13 C14 123.87(18) O14 C13 C14 113.97(16) C26 C25 C24 112.14(17) 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 122.57(17) O23 C23 C24 123.5(2) O24 C23 C24 113.88(17) O21 C21 O22 125.3(2) O21 C21 C22 117.76(18) O22 C21 C22 116.92(18) C27 C26 C25 111.87(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 112.18(17) C23 C24 H24A 109.2 C25 C24 H24A 109.2 C23 C24 H24B 109.2 C25 C24 H24B 109.2 H24A C24 H24B 107.9 C17 C16 C15 113.39(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 111.32(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 112.01(18) 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 119.15(18) O25 C27 C26 123.38(17) O26 C27 C26 117.45(18) O15 C17 O16 119.13(18) O15 C17 C16 123.97(19) O16 C17 C16 116.85(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 111.48(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 125.87(18) O11 C11 C12 117.66(17) O12 C11 C12 116.47(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O23 C23 1.228(2) O25 C27 1.214(3) O26 C27 1.328(2) O26 H26 0.8400 O21 C21 1.252(3) O22 C21 1.253(2) O13 C13 1.228(2) O24 C23 1.305(3) O24 H24 0.8400 O16 C17 1.331(3) O16 H16 0.8400 O14 C13 1.311(2) O14 H14 0.8400 O15 C17 1.212(3) N21 C22 1.482(3) 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 1.499(3) C25 C26 1.527(3) C25 C24 1.534(3) C25 H25A 0.9900 C25 H25B 0.9900 C23 C24 1.509(3) C26 C27 1.506(3) C26 H26A 0.9900 C26 H26B 0.9900 C24 H24A 0.9900 C24 H24B 0.9900 C16 C17 1.504(3) C16 C15 1.529(3) C16 H16A 0.9900 C16 H16B 0.9900 C14 C15 1.537(3) C14 H14A 0.9900 C14 H14B 0.9900 C15 H15A 0.9900 C15 H15B 0.9900 O11 C11 1.251(2) O12 C11 1.256(2) N11 C12 1.483(3) N11 H11A 0.9100 N11 H11B 0.9100 N11 H11C 0.9100 C12 C11 1.525(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 2.579(2) 177.5 O16 H16 O12 2_667 0.84 1.74 2.567(2) 165.9 N11 H11A O15 . 0.91 2.12 2.826(2) 133.2 N11 H11B O23 2_666 0.91 1.96 2.860(2) 168.2 N11 H11C O23 . 0.91 2.10 2.967(2) 158.3 O24 H24 O11 1_455 0.84 1.73 2.5655(18) 176.3 O26 H26 O22 2_676 0.84 1.73 2.552(2) 165.7 N21 H21A O25 . 0.91 2.07 2.800(2) 136.8 N21 H21B O13 2_667 0.91 1.95 2.859(2) 171.8 N21 H21C O13 1_565 0.91 2.12 2.974(2) 156.1 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 -3.4(2) N21 C22 C21 O22 177.07(17) C24 C25 C26 C27 167.68(18) O23 C23 C24 C25 -142.6(2) O24 C23 C24 C25 37.7(3) C26 C25 C24 C23 178.32(18) O13 C13 C14 C15 98.0(2) O14 C13 C14 C15 -80.7(2) C17 C16 C15 C14 -74.9(2) C13 C14 C15 C16 176.58(18) C25 C26 C27 O25 -6.3(3) C25 C26 C27 O26 175.11(18) C15 C16 C17 O15 -3.7(3) C15 C16 C17 O16 178.74(18) N11 C12 C11 O11 -3.2(2) N11 C12 C11 O12 177.22(17)