#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:53:41 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105121.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_2105121 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 85.486(13) _cell_angle_beta 113.065(10) _cell_angle_gamma 88.263(12) _cell_formula_units_Z 4 _cell_length_a 4.8884(7) _cell_length_b 20.136(3) _cell_length_c 10.1518(15) _cell_measurement_reflns_used 8917 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 29.60 _cell_measurement_theta_min 2.06 _cell_volume 914.5(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 100(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.857 _diffrn_measured_fraction_theta_max 0.857 _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 0.0520 _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 8816 _diffrn_reflns_theta_full 29.20 _diffrn_reflns_theta_max 29.20 _diffrn_reflns_theta_min 2.03 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.505 _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 0.309 _refine_diff_density_min -0.290 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 4247 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.977 _refine_ls_R_factor_all 0.1030 _refine_ls_R_factor_gt 0.0529 _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^)+(0.0367P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.0971 _reflns_number_gt 2766 _reflns_number_total 4247 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.88840 20.13560 10.15180 85.48600 113.06500 88.26300 ZERR 4 0.00070 0.00300 0.00150 0.01300 0.01000 0.01200 LATT 1 SFAC C H N O UNIT 28 52 4 24 TEMP -173 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 0.036700 FVAR 0.71749 O23 4 0.187505 0.589070 0.449681 11.00000 0.01657 0.01086 = 0.01533 -0.00449 0.00709 -0.00321 O25 4 0.655452 0.848270 0.753438 11.00000 0.02147 0.01363 = 0.01528 -0.00365 0.01131 -0.00300 O26 4 0.858107 0.905250 0.625565 11.00000 0.02026 0.01338 = 0.01492 -0.00366 0.00988 -0.00548 AFIX 147 H26 2 0.896134 0.901155 0.552660 11.00000 -1.50000 AFIX 0 O21 4 0.127955 1.055796 0.824343 11.00000 0.01660 0.01543 = 0.01320 -0.00084 0.00805 0.00242 O22 4 0.001822 1.090185 0.592273 11.00000 0.01557 0.01773 = 0.01526 0.00222 0.00742 0.00298 O13 4 0.771160 0.087551 1.016034 11.00000 0.01392 0.01039 = 0.01348 -0.00038 0.00457 0.00010 O24 4 0.075391 0.654770 0.590625 11.00000 0.02264 0.01247 = 0.02256 -0.00614 0.01659 -0.00788 AFIX 147 H24 2 0.008340 0.619565 0.612497 11.00000 -1.50000 AFIX 0 O16 4 0.178206 0.405006 0.906762 11.00000 0.02436 0.01418 = 0.01468 0.00009 0.01086 0.00479 AFIX 147 H16 2 0.173741 0.405642 0.988533 11.00000 -1.50000 AFIX 0 O14 4 0.783892 0.153359 0.831511 11.00000 0.02138 0.01193 = 0.01719 0.00270 0.01181 0.00453 AFIX 147 H14 2 0.891633 0.120774 0.828166 11.00000 -1.50000 AFIX 0 O15 4 0.403006 0.345431 0.801738 11.00000 0.03149 0.01332 = 0.02072 0.00074 0.01804 0.00186 N21 3 0.581072 0.971989 0.845918 11.00000 0.01461 0.01002 = 0.01313 -0.00061 0.00647 0.00186 AFIX 137 H21A 2 0.707400 0.940235 0.836904 11.00000 -1.50000 H21B 2 0.455222 0.952175 0.880950 11.00000 -1.50000 H21C 2 0.688139 1.001087 0.907519 11.00000 -1.50000 AFIX 0 C22 1 0.405780 1.008612 0.703106 11.00000 0.01210 0.01133 = 0.01078 -0.00136 0.00658 -0.00082 AFIX 23 H22A 2 0.316771 0.976092 0.632381 11.00000 -1.20000 H22B 2 0.540570 1.034789 0.671036 11.00000 -1.20000 AFIX 0 C13 1 0.695154 0.140243 0.936754 11.00000 0.00955 0.01014 = 0.01158 -0.00354 0.00346 -0.00245 C25 1 0.480609 0.745044 0.578657 11.00000 0.00997 0.01338 = 0.01096 -0.00202 0.00417 -0.00219 AFIX 23 H25A 2 0.334255 0.761041 0.616216 11.00000 -1.20000 H25B 2 0.637641 0.716260 0.657031 11.00000 -1.20000 AFIX 0 C23 1 0.189868 0.643577 0.496903 11.00000 0.00902 0.01349 = 0.00977 -0.00109 0.00275 0.00022 C21 1 0.158586 1.055545 0.706691 11.00000 0.00897 0.00948 = 0.01415 -0.00169 0.00574 -0.00333 C26 1 0.620644 0.804859 0.534220 11.00000 0.01450 0.00974 = 0.01300 -0.00254 0.00752 -0.00183 AFIX 23 H26A 2 0.797686 0.788956 0.518161 11.00000 -1.20000 H26B 2 0.475817 0.827870 0.442378 11.00000 -1.20000 AFIX 0 C24 1 0.323835 0.703673 0.452361 11.00000 0.01567 0.01303 = 0.01195 -0.00295 0.00702 -0.00377 AFIX 23 H24A 2 0.164255 0.732243 0.374753 11.00000 -1.20000 H24B 2 0.469329 0.688429 0.413589 11.00000 -1.20000 AFIX 0 C16 1 0.495249 0.308587 1.047292 11.00000 0.01352 0.01120 = 0.01282 -0.00297 0.00239 -0.00016 AFIX 23 H16A 2 0.335477 0.291490 1.074935 11.00000 -1.20000 H16B 2 0.619378 0.335420 1.123807 11.00000 -1.20000 AFIX 0 C14 1 0.500331 0.195531 0.952681 11.00000 0.01444 0.01014 = 0.01324 -0.00121 0.00740 -0.00011 AFIX 23 H14A 2 0.378118 0.176978 1.003004 11.00000 -1.20000 H14B 2 0.363566 0.215801 0.856217 11.00000 -1.20000 AFIX 0 C15 1 0.688274 0.249479 1.037926 11.00000 0.01284 0.01546 = 0.01572 -0.00382 0.00183 0.00205 AFIX 23 H15A 2 0.815578 0.229638 1.136349 11.00000 -1.20000 H15B 2 0.820626 0.265617 0.991064 11.00000 -1.20000 AFIX 0 C27 1 0.712151 0.853579 0.646597 11.00000 0.00868 0.00912 = 0.01147 0.00020 0.00176 0.00158 C17 1 0.355323 0.353120 0.907659 11.00000 0.01271 0.00941 = 0.01554 -0.00170 0.00628 -0.00316 O11 4 0.838635 0.551775 0.653259 11.00000 0.01689 0.01392 = 0.01364 -0.00332 0.00833 -0.00498 O12 4 0.942005 0.586471 0.870264 11.00000 0.01617 0.01825 = 0.01561 -0.00785 0.00746 -0.00673 N11 3 0.424729 0.471047 0.662519 11.00000 0.01586 0.01157 = 0.01227 -0.00161 0.00824 -0.00398 AFIX 137 H11A 2 0.304460 0.441599 0.681736 11.00000 -1.50000 H11B 2 0.562303 0.448564 0.639970 11.00000 -1.50000 H11C 2 0.312914 0.500978 0.587059 11.00000 -1.50000 AFIX 0 C12 1 0.578722 0.506892 0.790901 11.00000 0.01210 0.01167 = 0.00967 -0.00204 0.00582 -0.00172 AFIX 23 H12A 2 0.681613 0.473976 0.875381 11.00000 -1.20000 H12B 2 0.429457 0.534053 0.810712 11.00000 -1.20000 AFIX 0 C11 1 0.805318 0.552221 0.769531 11.00000 0.00918 0.00916 = 0.01366 -0.00042 0.00613 0.00113 HKLF 4 REM REM R1 = 0.0529 for 2766 Fo > 4sig(Fo) and 0.1030 for all 4247 data REM 259 parameters refined using 0 restraints END WGHT 0.0367 0.0000 REM Highest difference peak 0.309, deepest hole -0.290, 1-sigma level 0.064 Q1 1 0.5170 0.7775 0.5392 11.00000 0.05 0.31 Q2 1 0.0797 0.5508 0.5467 11.00000 0.05 0.27 Q3 1 0.3752 0.3262 0.9737 11.00000 0.05 0.27 Q4 1 0.8958 0.6528 0.7486 11.00000 0.05 0.25 Q5 1 0.7739 0.8751 0.8207 11.00000 0.05 0.24 Q6 1 0.6031 0.1722 0.9471 11.00000 0.05 0.24 Q7 1 0.3123 0.8392 0.7665 11.00000 0.05 0.23 Q8 1 0.6560 0.8174 0.6119 11.00000 0.05 0.23 Q9 1 0.8333 0.1925 1.2753 11.00000 0.05 0.23 Q10 1 0.6058 0.7997 0.7263 11.00000 0.05 0.23 Q11 1 0.7990 0.5862 0.6014 11.00000 0.05 0.22 Q12 1 0.7947 0.2297 0.9460 11.00000 0.05 0.22 Q13 1 0.3173 0.6724 0.5012 11.00000 0.05 0.22 Q14 1 0.6234 0.7078 0.7581 11.00000 0.05 0.22 Q15 1 0.3620 0.4688 0.5213 11.00000 0.05 0.22 Q16 1 0.6558 0.6066 0.8026 11.00000 0.05 0.21 Q17 1 0.0418 0.6718 0.5071 11.00000 0.05 0.21 Q18 1 0.6926 0.5313 0.7784 11.00000 0.05 0.21 Q19 1 0.3163 0.1786 0.7360 11.00000 0.05 0.21 Q20 1 0.8546 0.0525 1.0174 11.00000 0.05 0.21 Q21 1 1.0089 0.5738 0.6563 11.00000 0.05 0.21 Q22 1 -0.1221 0.6721 0.4126 11.00000 0.05 0.21 Q23 1 0.5782 0.3509 0.8380 11.00000 0.05 0.21 Q24 1 0.8336 0.2861 0.9195 11.00000 0.05 0.20 Q25 1 0.8386 0.9403 0.6809 11.00000 0.05 0.20 Q26 1 0.4931 0.4921 0.7238 11.00000 0.05 0.20 Q27 1 0.5281 0.1360 1.0919 11.00000 0.05 0.20 Q28 1 0.4976 0.8376 0.8376 11.00000 0.05 0.20 Q29 1 0.3085 0.3386 0.8383 11.00000 0.05 0.20 Q30 1 0.2757 0.6027 0.5241 11.00000 0.05 0.20 Q31 1 0.3986 0.9326 0.9526 11.00000 0.05 0.20 Q32 1 0.9895 0.1564 0.7062 11.00000 0.05 0.19 Q33 1 0.7246 0.1421 1.1421 11.00000 0.05 0.19 Q34 1 0.8260 0.6194 0.8552 11.00000 0.05 0.19 Q35 1 0.5793 0.6539 0.4664 11.00000 0.05 0.19 Q36 1 0.7469 1.0108 0.7785 11.00000 0.05 0.19 Q37 1 0.5483 0.2289 0.9632 11.00000 0.05 0.19 Q38 1 -0.0492 1.0706 0.8293 11.00000 0.05 0.19 Q39 1 0.8499 1.0018 1.0225 11.00000 0.05 0.19 Q40 1 0.3238 0.4094 0.6325 11.00000 0.05 0.19 Q41 1 0.2803 1.0304 0.7124 11.00000 0.05 0.19 Q42 1 0.6139 0.7523 0.7529 11.00000 0.05 0.19 Q43 1 0.6473 0.9213 0.9929 11.00000 0.05 0.19 Q44 1 1.1909 0.2377 1.1796 11.00000 0.05 0.19 Q45 1 0.7418 0.7626 0.5180 11.00000 0.05 0.19 Q46 1 0.5476 0.2786 1.0000 11.00000 0.05 0.18 Q47 1 0.5639 0.8289 0.7863 11.00000 0.05 0.18 Q48 1 0.5643 0.4780 0.6209 11.00000 0.05 0.18 Q49 1 0.4505 0.1063 0.8391 11.00000 0.05 0.18 Q50 1 0.5347 0.6945 0.5240 11.00000 0.05 0.18 Q51 1 0.9268 0.9856 0.8819 11.00000 0.05 0.18 Q52 1 0.2535 0.6803 0.6603 11.00000 0.05 0.18 Q53 1 0.4218 0.7131 0.6734 11.00000 0.05 0.18 Q54 1 0.7700 0.8328 0.8652 11.00000 0.05 0.18 Q55 1 0.5496 0.6064 0.5934 11.00000 0.05 0.18 Q56 1 0.3808 0.7378 0.4801 11.00000 0.05 0.17 Q57 1 0.1941 1.1106 0.7774 11.00000 0.05 0.17 Q58 1 0.7939 0.5132 0.6057 11.00000 0.05 0.17 Q59 1 0.4582 0.2584 0.7793 11.00000 0.05 0.17 Q60 1 -0.2423 1.0986 0.5290 11.00000 0.05 0.17 Q61 1 0.8110 0.9891 0.7118 11.00000 0.05 0.17 Q62 1 0.7381 0.5040 0.7206 11.00000 0.05 0.17 Q63 1 0.3048 0.2931 0.8680 11.00000 0.05 0.17 Q64 1 0.3616 0.4097 0.5805 11.00000 0.05 0.17 Q65 1 0.2805 0.5633 0.5761 11.00000 0.05 0.17 Q66 1 0.8734 0.1983 0.8301 11.00000 0.05 0.17 Q67 1 0.1595 1.0871 0.8937 11.00000 0.05 0.17 Q68 1 0.1047 1.1224 0.6093 11.00000 0.05 0.17 Q69 1 0.1962 0.5631 0.7599 11.00000 0.05 0.17 Q70 1 0.1579 0.7076 0.6935 11.00000 0.05 0.17 Q71 1 0.3959 0.6769 0.7019 11.00000 0.05 0.17 Q72 1 0.9330 0.7800 0.6003 11.00000 0.05 0.16 Q73 1 0.4108 0.8327 0.6410 11.00000 0.05 0.16 Q74 1 0.6000 0.7876 0.3459 11.00000 0.05 0.16 Q75 1 0.4927 0.9915 0.7723 11.00000 0.05 0.16 Q76 1 0.9952 0.3114 1.0178 11.00000 0.05 0.16 Q77 1 0.2129 1.1529 0.6850 11.00000 0.05 0.16 Q78 1 0.5069 0.8257 0.3579 11.00000 0.05 0.16 Q79 1 0.1939 0.2767 1.1122 11.00000 0.05 0.16 Q80 1 0.4241 0.7611 0.3281 11.00000 0.05 0.16 Q81 1 -0.1925 1.1027 0.6595 11.00000 0.05 0.16 Q82 1 0.8416 0.7314 0.7452 11.00000 0.05 0.16 Q83 1 0.0598 1.0367 0.7420 11.00000 0.05 0.16 Q84 1 0.4942 0.4627 0.7601 11.00000 0.05 0.16 Q85 1 0.4824 0.3381 1.1037 11.00000 0.05 0.16 Q86 1 0.6527 0.1299 0.8599 11.00000 0.05 0.16 Q87 1 0.3774 0.7141 0.3097 11.00000 0.05 0.16 Q88 1 0.1045 0.4205 0.5586 11.00000 0.05 0.16 Q89 1 0.0862 0.2870 0.9382 11.00000 0.05 0.16 Q90 1 0.2311 0.8065 0.5984 11.00000 0.05 0.16 Q91 1 0.7089 0.5674 0.6745 11.00000 0.05 0.16 Q92 1 0.7390 0.6147 0.6612 11.00000 0.05 0.16 Q93 1 0.9580 0.1983 1.2010 11.00000 0.05 0.16 Q94 1 0.4258 0.9222 0.5883 11.00000 0.05 0.16 Q95 1 0.5140 0.4466 0.9588 11.00000 0.05 0.16 Q96 1 0.8719 0.6857 0.7917 11.00000 0.05 0.16 Q97 1 0.2738 0.2726 0.9935 11.00000 0.05 0.16 Q98 1 0.1520 1.0430 0.9333 11.00000 0.05 0.15 Q99 1 0.6674 0.7655 0.5996 11.00000 0.05 0.15 Q100 1 0.8086 0.8109 0.8355 11.00000 0.05 0.15 ; _cod_data_source_file gp5050.cif _cod_data_source_block 100 _cod_database_code 2105121 _cod_database_fobs_code 2105121 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 0.1875(4) 0.58907(6) 0.44968(16) 0.0138(3) Uani d . 1 O O25 0.6555(4) 0.84827(7) 0.75344(17) 0.0154(3) Uani d . 1 O O26 0.8581(4) 0.90525(7) 0.62556(17) 0.0151(3) Uani d . 1 H H26 0.8961 0.9012 0.5527 0.023 Uiso calc R 1 O O21 0.1280(4) 1.05580(7) 0.82434(16) 0.0145(3) Uani d . 1 O O22 0.0018(4) 1.09019(7) 0.59227(17) 0.0161(3) Uani d . 1 O O13 0.7712(3) 0.08755(6) 1.01603(16) 0.0129(3) Uani d . 1 O O24 0.0754(4) 0.65477(7) 0.59062(18) 0.0164(3) Uani d . 1 H H24 0.0083 0.6196 0.6125 0.025 Uiso calc R 1 O O16 0.1782(4) 0.40501(7) 0.90676(17) 0.0170(3) Uani d . 1 H H16 0.1737 0.4056 0.9885 0.025 Uiso calc R 1 O O14 0.7839(4) 0.15336(7) 0.83151(17) 0.0159(3) Uani d . 1 H H14 0.8916 0.1208 0.8282 0.024 Uiso calc R 1 O O15 0.4030(4) 0.34543(7) 0.80174(18) 0.0197(4) Uani d . 1 N N21 0.5811(4) 0.97199(8) 0.84592(19) 0.0124(4) Uani d . 1 H H21A 0.7074 0.9402 0.8369 0.019 Uiso calc R 1 H H21B 0.4552 0.9522 0.8809 0.019 Uiso calc R 1 H H21C 0.6881 1.0011 0.9075 0.019 Uiso calc R 1 C C22 0.4058(5) 1.00861(9) 0.7031(2) 0.0107(4) Uani d . 1 H H22A 0.3168 0.9761 0.6324 0.013 Uiso calc R 1 H H22B 0.5406 1.0348 0.6710 0.013 Uiso calc R 1 C C13 0.6952(5) 0.14024(9) 0.9368(2) 0.0105(4) Uani d . 1 C C25 0.4806(5) 0.74504(9) 0.5787(2) 0.0114(4) Uani d . 1 H H25A 0.3343 0.7610 0.6162 0.014 Uiso calc R 1 H H25B 0.6376 0.7163 0.6570 0.014 Uiso calc R 1 C C23 0.1899(5) 0.64358(9) 0.4969(2) 0.0111(4) Uani d . 1 C C21 0.1586(5) 1.05554(9) 0.7067(2) 0.0104(4) Uani d . 1 C C26 0.6206(5) 0.80486(9) 0.5342(2) 0.0117(4) Uani d . 1 H H26A 0.7977 0.7890 0.5182 0.014 Uiso calc R 1 H H26B 0.4758 0.8279 0.4424 0.014 Uiso calc R 1 C C24 0.3238(5) 0.70367(9) 0.4524(2) 0.0129(4) Uani d . 1 H H24A 0.1643 0.7322 0.3748 0.015 Uiso calc R 1 H H24B 0.4693 0.6884 0.4136 0.015 Uiso calc R 1 C C16 0.4952(5) 0.30859(9) 1.0473(2) 0.0133(4) Uani d . 1 H H16A 0.3355 0.2915 1.0749 0.016 Uiso calc R 1 H H16B 0.6194 0.3354 1.1238 0.016 Uiso calc R 1 C C14 0.5003(5) 0.19553(9) 0.9527(2) 0.0120(4) Uani d . 1 H H14A 0.3781 0.1770 1.0030 0.014 Uiso calc R 1 H H14B 0.3636 0.2158 0.8562 0.014 Uiso calc R 1 C C15 0.6883(5) 0.24948(10) 1.0379(2) 0.0158(4) Uani d . 1 H H15A 0.8156 0.2296 1.1363 0.019 Uiso calc R 1 H H15B 0.8206 0.2656 0.9911 0.019 Uiso calc R 1 C C27 0.7122(5) 0.85358(9) 0.6466(2) 0.0106(4) Uani d . 1 C C17 0.3553(5) 0.35312(9) 0.9077(2) 0.0123(4) Uani d . 1 O O11 0.8386(4) 0.55177(7) 0.65326(16) 0.0139(3) Uani d . 1 O O12 0.9420(4) 0.58647(7) 0.87026(17) 0.0158(3) Uani d . 1 N N11 0.4247(4) 0.47105(8) 0.66252(19) 0.0123(4) Uani d . 1 H H11A 0.3045 0.4416 0.6817 0.018 Uiso calc R 1 H H11B 0.5623 0.4486 0.6400 0.018 Uiso calc R 1 H H11C 0.3129 0.5010 0.5871 0.018 Uiso calc R 1 C C12 0.5787(5) 0.50689(9) 0.7909(2) 0.0106(4) Uani d . 1 H H12A 0.6816 0.4740 0.8754 0.013 Uiso calc R 1 H H12B 0.4295 0.5341 0.8107 0.013 Uiso calc R 1 C C11 0.8053(5) 0.55222(9) 0.7695(2) 0.0102(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 0.0166(8) 0.0109(7) 0.0153(8) -0.0032(5) 0.0071(7) -0.0045(5) O25 0.0215(9) 0.0136(7) 0.0153(8) -0.0030(6) 0.0113(7) -0.0037(5) O26 0.0203(9) 0.0134(7) 0.0149(8) -0.0055(6) 0.0099(7) -0.0037(5) O21 0.0166(8) 0.0154(7) 0.0132(8) 0.0024(6) 0.0080(7) -0.0008(5) O22 0.0156(8) 0.0177(7) 0.0153(8) 0.0030(6) 0.0074(7) 0.0022(5) O13 0.0139(8) 0.0104(6) 0.0135(8) 0.0001(5) 0.0046(7) -0.0004(5) O24 0.0226(9) 0.0125(7) 0.0226(9) -0.0079(6) 0.0166(7) -0.0061(6) O16 0.0244(10) 0.0142(7) 0.0147(8) 0.0048(6) 0.0109(7) 0.0001(5) O14 0.0214(9) 0.0119(7) 0.0172(8) 0.0045(6) 0.0118(7) 0.0027(5) O15 0.0315(10) 0.0133(7) 0.0207(9) 0.0019(6) 0.0180(8) 0.0007(6) N21 0.0146(9) 0.0100(7) 0.0131(9) 0.0019(6) 0.0065(8) -0.0006(6) C22 0.0121(10) 0.0113(9) 0.0108(10) -0.0008(7) 0.0066(8) -0.0014(7) C13 0.0096(10) 0.0101(8) 0.0116(10) -0.0024(7) 0.0035(9) -0.0035(7) C25 0.0100(10) 0.0134(9) 0.0110(10) -0.0022(7) 0.0042(8) -0.0020(7) C23 0.0090(10) 0.0135(9) 0.0098(10) 0.0002(7) 0.0028(8) -0.0011(7) C21 0.0090(10) 0.0095(8) 0.0142(10) -0.0033(7) 0.0057(9) -0.0017(7) C26 0.0145(11) 0.0097(8) 0.0130(10) -0.0018(7) 0.0075(9) -0.0025(7) C24 0.0157(11) 0.0130(9) 0.0120(10) -0.0038(7) 0.0070(9) -0.0030(7) C16 0.0135(11) 0.0112(9) 0.0128(10) -0.0002(7) 0.0024(9) -0.0030(7) C14 0.0144(11) 0.0101(9) 0.0132(10) -0.0001(7) 0.0074(9) -0.0012(7) C15 0.0128(11) 0.0155(9) 0.0157(11) 0.0020(8) 0.0018(9) -0.0038(7) C27 0.0087(10) 0.0091(8) 0.0115(10) 0.0016(7) 0.0018(8) 0.0002(7) C17 0.0127(11) 0.0094(9) 0.0155(11) -0.0032(7) 0.0063(9) -0.0017(7) O11 0.0169(9) 0.0139(7) 0.0136(8) -0.0050(6) 0.0083(7) -0.0033(5) O12 0.0162(8) 0.0182(7) 0.0156(8) -0.0067(6) 0.0075(7) -0.0079(6) N11 0.0159(9) 0.0116(8) 0.0123(9) -0.0040(6) 0.0082(8) -0.0016(6) C12 0.0121(11) 0.0117(9) 0.0097(10) -0.0017(7) 0.0058(8) -0.0020(7) C11 0.0092(10) 0.0092(8) 0.0137(10) 0.0011(7) 0.0061(8) -0.0004(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 112.03(17) 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 122.31(19) O13 C13 C14 123.72(19) O14 C13 C14 113.96(16) C26 C25 C24 111.99(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 122.71(18) O23 C23 C24 123.5(2) O24 C23 C24 113.84(17) O22 C21 O21 125.5(2) O22 C21 C22 117.20(18) O21 C21 C22 117.27(18) C27 C26 C25 111.88(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 112.07(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 113.01(18) C17 C16 H16A 109.0 C15 C16 H16A 109.0 C17 C16 H16B 109.0 C15 C16 H16B 109.0 H16A C16 H16B 107.8 C13 C14 C15 111.04(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 112.16(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 119.10(18) O25 C27 C26 123.30(17) O26 C27 C26 117.60(18) O15 C17 O16 119.60(19) O15 C17 C16 124.0(2) O16 C17 C16 116.40(19) 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 111.66(17) N11 C12 H12A 109.3 C11 C12 H12A 109.3 N11 C12 H12B 109.3 C11 C12 H12B 109.3 H12A C12 H12B 107.9 O12 C11 O11 125.93(19) O12 C11 C12 116.87(18) O11 C11 C12 117.20(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O23 C23 1.230(2) O25 C27 1.218(3) O26 C27 1.329(2) O26 H26 0.8400 O21 C21 1.261(3) O22 C21 1.251(3) O13 C13 1.232(2) O24 C23 1.309(3) O24 H24 0.8400 O16 C17 1.334(3) O16 H16 0.8400 O14 C13 1.313(3) O14 H14 0.8400 O15 C17 1.206(3) N21 C22 1.483(3) N21 H21A 0.9100 N21 H21B 0.9100 N21 H21C 0.9100 C22 C21 1.525(3) C22 H22A 0.9900 C22 H22B 0.9900 C13 C14 1.502(3) C25 C26 1.526(3) C25 C24 1.537(3) C25 H25A 0.9900 C25 H25B 0.9900 C23 C24 1.514(3) C26 C27 1.506(3) C26 H26A 0.9900 C26 H26B 0.9900 C24 H24A 0.9900 C24 H24B 0.9900 C16 C17 1.511(3) C16 C15 1.528(3) C16 H16A 0.9900 C16 H16B 0.9900 C14 C15 1.536(3) C14 H14A 0.9900 C14 H14B 0.9900 C15 H15A 0.9900 C15 H15B 0.9900 O11 C11 1.254(3) O12 C11 1.254(3) 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 1.73 2.571(2) 177.3 O16 H16 O12 2_667 0.84 1.75 2.568(2) 163.8 N11 H11A O15 . 0.91 2.14 2.824(2) 131.3 N11 H11B O23 2_666 0.91 1.96 2.851(2) 167.5 N11 H11C O23 . 0.91 2.08 2.953(2) 159.5 O24 H24 O11 1_455 0.84 1.72 2.5611(19) 174.5 O26 H26 O22 2_676 0.84 1.73 2.555(2) 167.8 N21 H21A O25 . 0.91 2.08 2.793(2) 134.6 N21 H21B O13 2_667 0.91 1.95 2.849(2) 171.4 N21 H21C O13 1_565 0.91 2.10 2.961(2) 157.7 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 178.23(17) N21 C22 C21 O21 -2.3(2) C24 C25 C26 C27 167.06(18) O23 C23 C24 C25 -142.8(2) O24 C23 C24 C25 37.3(3) C26 C25 C24 C23 178.91(18) O13 C13 C14 C15 96.8(2) O14 C13 C14 C15 -82.0(2) C17 C16 C15 C14 -74.2(2) C13 C14 C15 C16 176.23(18) C25 C26 C27 O25 -6.2(3) C25 C26 C27 O26 174.87(18) C15 C16 C17 O15 -4.0(3) C15 C16 C17 O16 178.57(17) N11 C12 C11 O12 177.91(18) N11 C12 C11 O11 -2.3(3)