#------------------------------------------------------------------------------ #$Date: 2012-07-05 09:29:12 +0100 (Thu, 05 Jul 2012) $ #$Revision: 61654 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105114.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_2105114 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_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 114.600(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.9022(7) _cell_length_b 20.901(3) _cell_length_c 10.2730(15) _cell_measurement_reflns_used 3205 _cell_measurement_temperature 275(2) _cell_measurement_theta_max 29.18 _cell_measurement_theta_min 1.96 _cell_volume 957.0(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 275(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _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 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0695 _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 6792 _diffrn_reflns_theta_full 29.21 _diffrn_reflns_theta_max 29.21 _diffrn_reflns_theta_min 1.95 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.438 _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 0.157 _refine_diff_density_min -0.175 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.870 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 130 _refine_ls_number_reflns 2570 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.870 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_gt 0.0431 _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^)+(0.0364P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.0854 _reflns_number_gt 1461 _reflns_number_total 2570 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.90220 20.90060 10.27300 90.00000 114.60000 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 2 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 0.036400 FVAR 0.69344 O1 4 0.130238 0.445343 0.333844 11.00000 0.04769 0.03939 = 0.04012 -0.00682 0.02813 -0.01472 O5 4 0.620450 0.640847 0.221109 11.00000 0.06654 0.03423 = 0.04164 0.00649 0.03460 0.00487 O3 4 0.202115 0.915592 -0.033399 11.00000 0.04739 0.02665 = 0.04142 0.00206 0.02341 0.00010 N1 3 0.557523 0.525197 0.336588 11.00000 0.03771 0.02915 = 0.03688 0.00009 0.02178 -0.00790 AFIX 137 H1A 2 0.661340 0.556169 0.318405 11.00000 -1.50000 H1B 2 0.682710 0.499573 0.404323 11.00000 -1.50000 H1C 2 0.427397 0.542367 0.366397 11.00000 -1.50000 AFIX 0 C2 1 0.393664 0.487882 0.205076 11.00000 0.03142 0.03116 = 0.03102 -0.00057 0.01584 -0.00206 AFIX 23 H2A 2 0.536392 0.464335 0.180650 11.00000 -1.20000 H2B 2 0.285672 0.516955 0.126867 11.00000 -1.20000 AFIX 0 O6 4 0.820241 0.594201 0.091606 11.00000 0.06599 0.03231 = 0.04618 0.00583 0.03215 0.01552 AFIX 147 H6 2 0.848796 0.601804 0.019957 11.00000 -1.50000 AFIX 0 O2 4 0.047022 0.402448 0.122625 11.00000 0.05402 0.04979 = 0.05252 -0.02310 0.03180 -0.02234 C1 1 0.173594 0.441304 0.222191 11.00000 0.02935 0.02690 = 0.03794 -0.00053 0.01684 0.00161 C7 1 0.676810 0.642425 0.116816 11.00000 0.03493 0.02506 = 0.03400 -0.00158 0.01531 -0.00198 O4 4 0.106389 0.846594 0.105540 11.00000 0.07866 0.03458 = 0.06941 0.01488 0.05795 0.01796 AFIX 147 H4 2 0.037962 0.878835 0.126403 11.00000 -1.50000 AFIX 0 C5 1 0.467437 0.753607 0.067809 11.00000 0.05167 0.03032 = 0.03818 0.00484 0.02564 0.00924 AFIX 23 H5A 2 0.323363 0.738199 0.102634 11.00000 -1.20000 H5B 2 0.633515 0.772518 0.148159 11.00000 -1.20000 AFIX 0 C6 1 0.582934 0.697333 0.013018 11.00000 0.04377 0.02848 = 0.03679 0.00347 0.02337 0.00527 AFIX 23 H6B 2 0.427126 0.682974 -0.077027 11.00000 -1.20000 H6A 2 0.753023 0.711001 -0.005118 11.00000 -1.20000 AFIX 0 C3 1 0.206790 0.860868 0.009397 11.00000 0.03465 0.03166 = 0.03259 0.00373 0.01660 0.00331 C4 1 0.320678 0.804674 -0.043069 11.00000 0.05251 0.03448 = 0.04097 0.00731 0.02795 0.01094 AFIX 23 H4A 2 0.464638 0.819717 -0.078327 11.00000 -1.20000 H4B 2 0.154290 0.785671 -0.123122 11.00000 -1.20000 HKLF 4 REM REM R1 = 0.0431 for 1461 Fo > 4sig(Fo) and 0.1002 for all 2570 data REM 130 parameters refined using 0 restraints END WGHT 0.0364 0.0000 REM Highest difference peak 0.157, deepest hole -0.175, 1-sigma level 0.041 Q1 1 1.1526 0.6422 0.1950 11.00000 0.05 0.16 Q2 1 0.0282 0.9711 -0.0874 11.00000 0.05 0.15 Q3 1 0.0587 0.7252 0.0818 11.00000 0.05 0.13 Q4 1 0.7576 0.7822 0.0807 11.00000 0.05 0.13 Q5 1 0.4310 0.7831 0.0174 11.00000 0.05 0.13 Q6 1 0.2963 0.8245 -0.1393 11.00000 0.05 0.13 Q7 1 0.1153 0.7283 0.0041 11.00000 0.05 0.13 Q8 1 0.4972 0.7521 0.1775 11.00000 0.05 0.12 Q9 1 0.4909 0.7215 0.0360 11.00000 0.05 0.12 Q10 1 0.5666 0.8304 -0.0150 11.00000 0.05 0.12 Q11 1 0.6375 0.8775 0.0073 11.00000 0.05 0.12 Q12 1 0.7989 0.6311 0.3486 11.00000 0.05 0.12 Q13 1 0.6809 0.6740 0.0771 11.00000 0.05 0.12 Q14 1 -0.0318 0.7890 -0.1565 11.00000 0.05 0.11 Q15 1 0.0473 0.7578 -0.2013 11.00000 0.05 0.11 Q16 1 0.7963 0.8071 0.1513 11.00000 0.05 0.11 Q17 1 0.0166 0.4526 0.2604 11.00000 0.05 0.11 Q18 1 0.1762 0.4068 0.3783 11.00000 0.05 0.11 Q19 1 0.6956 0.7059 -0.0888 11.00000 0.05 0.11 Q20 1 0.2114 0.6586 -0.1030 11.00000 0.05 0.11 Q21 1 0.6301 0.6647 -0.1385 11.00000 0.05 0.11 Q22 1 0.3486 0.7268 0.2235 11.00000 0.05 0.11 Q23 1 0.4592 0.6352 -0.1982 11.00000 0.05 0.10 Q24 1 0.2921 0.9070 0.0222 11.00000 0.05 0.10 Q25 1 -0.2476 0.3990 0.0829 11.00000 0.05 0.10 Q26 1 0.0513 0.8647 -0.2131 11.00000 0.05 0.10 Q27 1 -0.2008 0.4465 0.0331 11.00000 0.05 0.10 Q28 1 0.6294 0.6918 -0.0559 11.00000 0.05 0.10 Q29 1 -0.2893 0.8577 0.1416 11.00000 0.05 0.10 Q30 1 0.7186 0.7701 -0.0778 11.00000 0.05 0.10 ; _[local]_cod_data_source_file gp5050.cif _[local]_cod_data_source_block 275 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_original_cell_volume 957.0(2) _cod_database_code 2105114 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 0.1302(3) 0.44534(6) 0.33384(11) 0.0391(3) Uani d . 1 1 O O5 0.6205(3) 0.64085(6) 0.22111(12) 0.0434(3) Uani d . 1 1 O O3 0.2021(3) 0.91559(5) -0.03340(11) 0.0368(3) Uani d . 1 1 N N1 0.5575(3) 0.52520(6) 0.33659(13) 0.0325(3) Uani d . 1 1 H H1A 0.6613 0.5562 0.3184 0.049 Uiso calc R 1 1 H H1B 0.6827 0.4996 0.4043 0.049 Uiso calc R 1 1 H H1C 0.4274 0.5424 0.3664 0.049 Uiso calc R 1 1 C C2 0.3937(4) 0.48788(8) 0.20508(15) 0.0302(4) Uani d . 1 1 H H2A 0.5364 0.4643 0.1807 0.036 Uiso calc R 1 1 H H2B 0.2857 0.5170 0.1269 0.036 Uiso calc R 1 1 O O6 0.8202(3) 0.59420(6) 0.09161(12) 0.0452(3) Uani d . 1 1 H H6 0.8488 0.6018 0.0200 0.068 Uiso calc R 1 1 O O2 0.0470(3) 0.40245(6) 0.12262(13) 0.0489(4) Uani d . 1 1 C C1 0.1736(4) 0.44130(8) 0.22219(16) 0.0304(4) Uani d . 1 1 C C7 0.6768(4) 0.64243(8) 0.11682(16) 0.0310(4) Uani d . 1 1 O O4 0.1064(4) 0.84659(6) 0.10554(15) 0.0518(4) Uani d . 1 1 H H4 0.0380 0.8788 0.1264 0.078 Uiso calc R 1 1 C C5 0.4674(4) 0.75361(8) 0.06781(16) 0.0377(4) Uani d . 1 1 H H5A 0.3234 0.7382 0.1026 0.045 Uiso calc R 1 1 H H5B 0.6335 0.7725 0.1482 0.045 Uiso calc R 1 1 C C6 0.5829(4) 0.69733(7) 0.01302(17) 0.0341(4) Uani d . 1 1 H H6B 0.4271 0.6830 -0.0770 0.041 Uiso calc R 1 1 H H6A 0.7530 0.7110 -0.0051 0.041 Uiso calc R 1 1 C C3 0.2068(4) 0.86087(8) 0.00940(16) 0.0321(4) Uani d . 1 1 C C4 0.3207(5) 0.80467(8) -0.04307(17) 0.0398(5) Uani d . 1 1 H H4A 0.4646 0.8197 -0.0783 0.048 Uiso calc R 1 1 H H4B 0.1543 0.7857 -0.1231 0.048 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 0.0477(8) 0.0394(7) 0.0401(6) -0.0147(6) 0.0281(6) -0.0068(5) O5 0.0665(10) 0.0342(7) 0.0416(6) 0.0049(7) 0.0346(7) 0.0065(5) O3 0.0474(8) 0.0267(6) 0.0414(6) 0.0001(6) 0.0234(6) 0.0021(5) N1 0.0377(9) 0.0291(7) 0.0369(7) -0.0079(7) 0.0218(6) 0.0001(6) C2 0.0314(10) 0.0312(8) 0.0310(8) -0.0021(8) 0.0158(7) -0.0006(6) O6 0.0660(10) 0.0323(7) 0.0462(7) 0.0155(7) 0.0321(7) 0.0058(5) O2 0.0540(9) 0.0498(8) 0.0525(7) -0.0223(7) 0.0318(7) -0.0231(6) C1 0.0294(10) 0.0269(8) 0.0379(8) 0.0016(8) 0.0168(7) -0.0005(7) C7 0.0349(10) 0.0251(8) 0.0340(8) -0.0020(8) 0.0153(7) -0.0016(6) O4 0.0787(11) 0.0346(7) 0.0694(8) 0.0180(7) 0.0579(8) 0.0149(6) C5 0.0517(12) 0.0303(9) 0.0382(8) 0.0092(9) 0.0256(8) 0.0048(7) C6 0.0438(12) 0.0285(8) 0.0368(8) 0.0053(8) 0.0234(8) 0.0035(7) C3 0.0347(11) 0.0317(9) 0.0326(8) 0.0033(8) 0.0166(8) 0.0037(7) C4 0.0525(13) 0.0345(10) 0.0410(9) 0.0109(9) 0.0279(9) 0.0073(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 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 112.07(12) 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 125.25(16) O2 C1 C2 117.19(14) O1 C1 C2 117.56(14) O5 C7 O6 119.35(14) O5 C7 C6 122.17(15) O6 C7 C6 118.47(13) C3 O4 H4 109.5 C4 C5 C6 113.85(13) C4 C5 H5A 108.8 C6 C5 H5A 108.8 C4 C5 H5B 108.8 C6 C5 H5B 108.8 H5A C5 H5B 107.7 C7 C6 C5 112.43(12) C7 C6 H6B 109.1 C5 C6 H6B 109.1 C7 C6 H6A 109.1 C5 C6 H6A 109.1 H6B C6 H6A 107.9 O3 C3 O4 121.90(15) O3 C3 C4 124.04(14) O4 C3 C4 114.06(14) C3 C4 C5 114.62(13) C3 C4 H4A 108.6 C5 C4 H4A 108.6 C3 C4 H4B 108.6 C5 C4 H4B 108.6 H4A C4 H4B 107.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.2534(18) O5 C7 1.2132(18) O3 C3 1.2221(19) N1 C2 1.4749(19) N1 H1A 0.8900 N1 H1B 0.8900 N1 H1C 0.8900 C2 C1 1.517(2) C2 H2A 0.9700 C2 H2B 0.9700 O6 C7 1.3149(19) O6 H6 0.8200 O2 C1 1.2499(19) C7 C6 1.502(2) O4 C3 1.3082(19) O4 H4 0.8200 C5 C4 1.507(2) C5 C6 1.512(2) C5 H5A 0.9700 C5 H5B 0.9700 C6 H6B 0.9700 C6 H6A 0.9700 C3 C4 1.494(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 2.13 2.9564(18) 154.2 N1 H1C O3 4_576 0.89 2.00 2.8789(18) 169.4 N1 H1A O5 . 0.89 2.00 2.7658(17) 143.2 O4 H4 O1 2 0.82 1.75 2.5680(17) 176.4 O6 H6 O2 3_665 0.82 1.74 2.5425(17) 164.5 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 -172.37(15) N1 C2 C1 O1 8.5(2) O5 C7 C6 C5 10.6(3) O6 C7 C6 C5 -170.55(16) C4 C5 C6 C7 -169.69(17) O3 C3 C4 C5 147.16(18) O4 C3 C4 C5 -33.7(2) C6 C5 C4 C3 -179.64(16)