#------------------------------------------------------------------------------ #$Date: 2012-07-05 09:29:12 +0100 (Thu, 05 Jul 2012) $ #$Revision: 61654 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105113.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_2105113 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_coeditor_code GP5050 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 287 _journal_page_last 296 _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 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 114.586(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.9110(7) _cell_length_b 20.922(3) _cell_length_c 10.2744(15) _cell_measurement_reflns_used 3307 _cell_measurement_temperature 300(2) _cell_measurement_theta_max 29.15 _cell_measurement_theta_min 1.97 _cell_volume 960.0(3) _computing_cell_refinement 'STOE X-AREA (Stoe & Cie, 2006)' _computing_data_collection 'STOE X-AREA (Stoe & Cie, 2006)' _computing_data_reduction 'STOE X-RED (Stoe & Cie, 2006)' _computing_molecular_graphics 'Mercury (Macrae et al., 2006)' _computing_publication_material ; Mercury (Macrae et al., 2006), PLATON (Spek, 2009), enCIFer (Allen et al., 2004) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, 2008) and X-STEP32 (Stoe & Cie, 2000) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 300(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _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 0.0455 _diffrn_reflns_av_sigmaI/netI 0.0713 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 6828 _diffrn_reflns_theta_full 29.20 _diffrn_reflns_theta_max 29.20 _diffrn_reflns_theta_min 1.95 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.191 _refine_diff_density_min -0.172 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.888 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 130 _refine_ls_number_reflns 2578 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.888 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0475 _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^)+(0.0419P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.0955 _reflns_number_gt 1421 _reflns_number_total 2578 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.91100 20.92160 10.27440 90.00000 114.58600 90.00000 ZERR 4 0.00070 0.00260 0.00150 0.00000 0.01000 0.00000 LATT 1 SYMM -X, Y+ 0.50000, -Z+ 0.50000 SFAC C H N O UNIT 28 52 4 24 TEMP 27 PLAN 30 FMAP 2 L.S. 100 BOND CONF ACTA EQIV $1 1-X,-1/2+Y,1/2-Z EQIV $2 X,1.5-Y,0.5+Z EQIV $3 -X,0.5+Y,0.5-Z EQIV $4 1-X,1-Y,-Z HTAB N1 O3_$1 HTAB N1 O3_$2 HTAB N1 O5 HTAB O4 O1_$3 HTAB O6 O2_$4 BOND $H WGHT 0.041900 FVAR 1.29340 O1 4 0.130346 0.445531 0.333534 11.00000 0.05369 0.04173 = 0.04536 -0.00628 0.03195 -0.01534 O5 4 0.618020 0.641129 0.220437 11.00000 0.07610 0.03837 = 0.04803 0.00670 0.04053 0.00491 O3 4 0.201693 0.915495 -0.033139 11.00000 0.05364 0.02931 = 0.04731 0.00272 0.02749 0.00038 N1 3 0.556630 0.525539 0.336237 11.00000 0.04223 0.03210 = 0.03956 0.00002 0.02277 -0.00840 AFIX 137 H1A 2 0.659866 0.556527 0.317931 11.00000 -1.50000 H1B 2 0.681928 0.499983 0.403929 11.00000 -1.50000 H1C 2 0.426766 0.542630 0.366145 11.00000 -1.50000 AFIX 0 C2 1 0.393209 0.488233 0.204907 11.00000 0.03483 0.03504 = 0.03444 -0.00019 0.01864 -0.00213 AFIX 23 H2A 2 0.535714 0.464893 0.180163 11.00000 -1.20000 H2B 2 0.284315 0.517225 0.126793 11.00000 -1.20000 AFIX 0 O6 4 0.816735 0.594631 0.091058 11.00000 0.07264 0.03603 = 0.05104 0.00608 0.03492 0.01634 AFIX 147 H6 2 0.841827 0.601815 0.018352 11.00000 -1.50000 AFIX 0 O2 4 0.051025 0.402461 0.123454 11.00000 0.06115 0.05560 = 0.05752 -0.02365 0.03585 -0.02426 C1 1 0.175315 0.441490 0.222595 11.00000 0.03311 0.03064 = 0.03889 -0.00146 0.01799 0.00137 C7 1 0.674006 0.642811 0.116205 11.00000 0.04076 0.02768 = 0.03773 -0.00200 0.01836 -0.00273 O4 4 0.106331 0.846766 0.105981 11.00000 0.08526 0.03777 = 0.07579 0.01597 0.06269 0.01946 AFIX 147 H4 2 0.035577 0.878831 0.125978 11.00000 -1.50000 AFIX 0 C5 1 0.464456 0.753757 0.067209 11.00000 0.05870 0.03347 = 0.04189 0.00566 0.02798 0.01029 AFIX 23 H5A 2 0.319480 0.738291 0.101232 11.00000 -1.20000 H5B 2 0.629528 0.772479 0.148119 11.00000 -1.20000 AFIX 0 C6 1 0.580992 0.697516 0.012766 11.00000 0.04826 0.03247 = 0.03981 0.00367 0.02518 0.00477 AFIX 23 H6B 2 0.426143 0.683143 -0.077414 11.00000 -1.20000 H6A 2 0.751152 0.711236 -0.004995 11.00000 -1.20000 AFIX 0 C3 1 0.206365 0.861071 0.010033 11.00000 0.03736 0.03280 = 0.03674 0.00411 0.01892 0.00410 C4 1 0.320408 0.804834 -0.042452 11.00000 0.05808 0.03894 = 0.04608 0.00872 0.03178 0.01285 AFIX 23 H4A 2 0.465060 0.819870 -0.077110 11.00000 -1.20000 H4B 2 0.154613 0.786061 -0.122950 11.00000 -1.20000 HKLF 4 REM REM R1 = 0.0475 for 1421 Fo > 4sig(Fo) and 0.1059 for all 2578 data REM 130 parameters refined using 0 restraints END WGHT 0.0419 0.0000 REM Highest difference peak 0.191, deepest hole -0.172, 1-sigma level 0.040 Q1 1 0.3149 0.8116 -0.1199 11.00000 0.05 0.19 Q2 1 0.6102 0.6957 -0.0780 11.00000 0.05 0.17 Q3 1 0.4844 0.7509 0.1698 11.00000 0.05 0.14 Q4 1 0.2048 0.4006 0.1953 11.00000 0.05 0.14 Q5 1 0.3179 0.9007 0.0200 11.00000 0.05 0.13 Q6 1 0.0101 0.4486 0.2711 11.00000 0.05 0.13 Q7 1 0.4220 0.6421 0.1607 11.00000 0.05 0.13 Q8 1 0.9676 0.5107 0.5195 11.00000 0.05 0.12 Q9 1 0.2021 0.9462 0.0072 11.00000 0.05 0.12 Q10 1 0.5848 0.8378 -0.0188 11.00000 0.05 0.12 Q11 1 0.9977 0.7192 0.1609 11.00000 0.05 0.12 Q12 1 0.0966 0.3899 0.0561 11.00000 0.05 0.12 Q13 1 0.3153 0.8388 -0.0121 11.00000 0.05 0.12 Q14 1 0.3296 0.9195 -0.0812 11.00000 0.05 0.12 Q15 1 1.0196 0.7190 0.0691 11.00000 0.05 0.12 Q16 1 0.0933 0.4012 0.3080 11.00000 0.05 0.11 Q17 1 0.7582 0.7844 0.1129 11.00000 0.05 0.11 Q18 1 0.1913 0.7219 0.0333 11.00000 0.05 0.11 Q19 1 0.4863 0.6121 0.2023 11.00000 0.05 0.11 Q20 1 0.0861 0.3812 0.1951 11.00000 0.05 0.11 Q21 1 0.0438 0.9032 -0.1351 11.00000 0.05 0.10 Q22 1 0.5170 0.6815 0.2115 11.00000 0.05 0.10 Q23 1 0.7195 0.7618 0.2673 11.00000 0.05 0.10 Q24 1 0.4049 0.8614 -0.1139 11.00000 0.05 0.10 Q25 1 0.8692 0.7803 0.2145 11.00000 0.05 0.10 Q26 1 0.2351 0.3906 0.3457 11.00000 0.05 0.10 Q27 1 0.2952 0.7462 -0.2051 11.00000 0.05 0.10 Q28 1 -0.0057 0.3699 0.1430 11.00000 0.05 0.10 Q29 1 0.0263 0.9462 -0.0063 11.00000 0.05 0.10 Q30 1 0.9406 0.5089 0.4076 11.00000 0.05 0.10 ; _[local]_cod_data_source_file gp5050.cif _[local]_cod_data_source_block 300 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 959.9(2) _cod_database_code 2105113 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 _atom_site_symmetry_multiplicity O O1 0.1303(3) 0.44553(6) 0.33353(12) 0.0431(3) Uani d . 1 1 O O5 0.6180(3) 0.64113(6) 0.22044(13) 0.0492(4) Uani d . 1 1 O O3 0.2017(3) 0.91549(6) -0.03314(12) 0.0412(3) Uani d . 1 1 N N1 0.5566(4) 0.52554(7) 0.33624(14) 0.0360(4) Uani d . 1 1 H H1A 0.6599 0.5565 0.3179 0.054 Uiso calc R 1 1 H H1B 0.6819 0.5000 0.4039 0.054 Uiso calc R 1 1 H H1C 0.4268 0.5426 0.3661 0.054 Uiso calc R 1 1 C C2 0.3932(4) 0.48823(8) 0.20491(17) 0.0334(4) Uani d . 1 1 H H2A 0.5357 0.4649 0.1802 0.040 Uiso calc R 1 1 H H2B 0.2843 0.5172 0.1268 0.040 Uiso calc R 1 1 O O6 0.8167(4) 0.59463(6) 0.09106(14) 0.0501(4) Uani d . 1 1 H H6 0.8418 0.6018 0.0184 0.075 Uiso calc R 1 1 O O2 0.0510(3) 0.40246(7) 0.12345(14) 0.0543(4) Uani d . 1 1 C C1 0.1753(4) 0.44149(8) 0.22259(17) 0.0332(4) Uani d . 1 1 C C7 0.6740(4) 0.64281(8) 0.11621(17) 0.0347(4) Uani d . 1 1 O O4 0.1063(4) 0.84677(6) 0.10598(16) 0.0565(4) Uani d . 1 1 H H4 0.0356 0.8788 0.1260 0.085 Uiso calc R 1 1 C C5 0.4645(5) 0.75376(9) 0.06721(18) 0.0423(5) Uani d . 1 1 H H5A 0.3195 0.7383 0.1012 0.051 Uiso calc R 1 1 H H5B 0.6295 0.7725 0.1481 0.051 Uiso calc R 1 1 C C6 0.5810(5) 0.69752(8) 0.01277(18) 0.0379(4) Uani d . 1 1 H H6B 0.4261 0.6831 -0.0774 0.045 Uiso calc R 1 1 H H6A 0.7512 0.7112 -0.0050 0.045 Uiso calc R 1 1 C C3 0.2064(4) 0.86107(8) 0.01003(17) 0.0345(4) Uani d . 1 1 C C4 0.3204(5) 0.80483(9) -0.04245(19) 0.0443(5) Uani d . 1 1 H H4A 0.4651 0.8199 -0.0771 0.053 Uiso calc R 1 1 H H4B 0.1546 0.7861 -0.1230 0.053 Uiso calc R 1 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 O1 0.0537(9) 0.0417(7) 0.0454(7) -0.0153(7) 0.0319(6) -0.0063(6) O5 0.0761(11) 0.0384(7) 0.0480(7) 0.0049(7) 0.0405(7) 0.0067(6) O3 0.0536(9) 0.0293(6) 0.0473(7) 0.0004(6) 0.0275(6) 0.0027(5) N1 0.0422(10) 0.0321(8) 0.0396(7) -0.0084(7) 0.0228(7) 0.0000(6) C2 0.0348(11) 0.0350(9) 0.0344(8) -0.0021(8) 0.0186(8) -0.0002(7) O6 0.0726(11) 0.0360(7) 0.0510(8) 0.0163(7) 0.0349(8) 0.0061(6) O2 0.0612(10) 0.0556(9) 0.0575(8) -0.0243(8) 0.0358(7) -0.0237(7) C1 0.0331(11) 0.0306(9) 0.0389(9) 0.0014(8) 0.0180(8) -0.0015(7) C7 0.0408(12) 0.0277(9) 0.0377(8) -0.0027(8) 0.0184(8) -0.0020(7) O4 0.0853(12) 0.0378(8) 0.0758(9) 0.0195(8) 0.0627(9) 0.0160(7) C5 0.0587(14) 0.0335(10) 0.0419(9) 0.0103(9) 0.0280(9) 0.0057(7) C6 0.0483(13) 0.0325(9) 0.0398(9) 0.0048(9) 0.0252(9) 0.0037(7) C3 0.0374(11) 0.0328(9) 0.0367(9) 0.0041(8) 0.0189(8) 0.0041(7) C4 0.0581(14) 0.0389(11) 0.0461(10) 0.0129(10) 0.0318(10) 0.0087(8) 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 C2 N1 H1A 109.5 C2 N1 H1B 109.5 H1A N1 H1B 109.5 C2 N1 H1C 109.5 H1A N1 H1C 109.5 H1B N1 H1C 109.5 N1 C2 C1 112.00(13) N1 C2 H2A 109.2 C1 C2 H2A 109.2 N1 C2 H2B 109.2 C1 C2 H2B 109.2 H2A C2 H2B 107.9 C7 O6 H6 109.5 O2 C1 O1 125.15(17) O2 C1 C2 117.00(15) O1 C1 C2 117.83(15) O5 C7 O6 119.17(15) O5 C7 C6 122.33(16) O6 C7 C6 118.49(14) C3 O4 H4 109.5 C4 C5 C6 114.14(14) C4 C5 H5A 108.7 C6 C5 H5A 108.7 C4 C5 H5B 108.7 C6 C5 H5B 108.7 H5A C5 H5B 107.6 C7 C6 C5 112.48(13) C7 C6 H6B 109.1 C5 C6 H6B 109.1 C7 C6 H6A 109.1 C5 C6 H6A 109.1 H6B C6 H6A 107.8 O3 C3 O4 122.19(16) O3 C3 C4 123.82(15) O4 C3 C4 113.98(15) C3 C4 C5 114.82(14) C3 C4 H4A 108.6 C5 C4 H4A 108.6 C3 C4 H4B 108.6 C5 C4 H4B 108.6 H4A C4 H4B 107.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.2508(19) O5 C7 1.212(2) O3 C3 1.219(2) N1 C2 1.474(2) N1 H1A 0.8900 N1 H1B 0.8900 N1 H1C 0.8900 C2 C1 1.515(2) C2 H2A 0.9700 C2 H2B 0.9700 O6 C7 1.313(2) O6 H6 0.8200 O2 C1 1.249(2) C7 C6 1.498(2) O4 C3 1.306(2) O4 H4 0.8200 C5 C4 1.500(2) C5 C6 1.514(2) C5 H5A 0.9700 C5 H5B 0.9700 C6 H6B 0.9700 C6 H6A 0.9700 C3 C4 1.497(2) C4 H4A 0.9700 C4 H4B 0.9700 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 N1 H1B O3 2_645 0.89 2.14 2.9671(19) 154.2 N1 H1C O3 4_576 0.89 2.00 2.8824(19) 169.4 N1 H1A O5 . 0.89 2.00 2.7665(18) 143.2 O4 H4 O1 2 0.82 1.75 2.5706(18) 177.5 O6 H6 O2 3_665 0.82 1.75 2.5444(18) 164.4 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 N1 C2 C1 O2 -171.95(16) N1 C2 C1 O1 9.1(2) O5 C7 C6 C5 10.4(3) O6 C7 C6 C5 -170.82(17) C4 C5 C6 C7 -170.01(18) O3 C3 C4 C5 147.7(2) O4 C3 C4 C5 -33.3(3) C6 C5 C4 C3 -179.48(18)