#------------------------------------------------------------------------------ #$Date: 2017-10-13 06:28:26 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201972 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105116.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_2105116 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 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 114.648(9) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 4.8888(6) _cell_length_b 20.859(2) _cell_length_c 10.2664(13) _cell_measurement_reflns_used 3782 _cell_measurement_temperature 225(2) _cell_measurement_theta_max 29.50 _cell_measurement_theta_min 1.95 _cell_volume 951.5(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 225(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0645 _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 6775 _diffrn_reflns_theta_full 29.16 _diffrn_reflns_theta_max 29.16 _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 1.446 _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 0.210 _refine_diff_density_min -0.181 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.878 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 130 _refine_ls_number_reflns 2558 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.878 _refine_ls_R_factor_all 0.0834 _refine_ls_R_factor_gt 0.0415 _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^)+(0.0370P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0727 _refine_ls_wR_factor_ref 0.0811 _reflns_number_gt 1594 _reflns_number_total 2558 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL CELL 0.71073 4.88880 20.85950 10.26640 90.00000 114.64800 90.00000 ZERR 4 0.00060 0.00240 0.00130 0.00000 0.00900 0.00000 LATT 1 SYMM -X, Y+ 0.50000, -Z+ 0.50000 SFAC C H N O UNIT 28 52 4 24 TEMP -48 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 FVAR 1.26796 WGHT 0.03700 0.00000 O1 4 0.129710 0.445190 0.334413 11.000000 0.038200 0.031680 = 0.032270 -0.005200 0.022460 -0.011260 O5 4 0.625280 0.640460 0.222185 11.000000 0.051210 0.027690 = 0.033760 0.005130 0.026560 0.003670 O3 4 0.203287 0.915612 -0.033955 11.000000 0.037580 0.021710 = 0.033230 0.001590 0.018340 0.000200 N1 3 0.559364 0.524769 0.337232 11.000000 0.030780 0.023400 = 0.029520 0.000580 0.017350 -0.005400 AFIX 137 H1A 2 0.665154 0.556090 0.319013 11.000000 -1.500000 H1B 2 0.685945 0.498723 0.405763 11.000000 -1.500000 H1C 2 0.427533 0.542241 0.367348 11.000000 -1.500000 AFIX 0 C2 1 0.394410 0.487449 0.205273 11.000000 0.025850 0.026870 = 0.025530 0.000210 0.013630 -0.000500 AFIX 23 H2A 2 0.538655 0.463299 0.180941 11.000000 -1.200000 H2B 2 0.286387 0.516953 0.126091 11.000000 -1.200000 AFIX 0 O6 4 0.826765 0.593500 0.092911 11.000000 0.051500 0.027300 = 0.037620 0.004420 0.025130 0.012090 AFIX 147 H6 2 0.856341 0.601163 0.020491 11.000000 -1.500000 AFIX 0 O2 4 0.040202 0.402719 0.121333 11.000000 0.043150 0.042700 = 0.042120 -0.018200 0.024880 -0.017270 C1 1 0.171462 0.441195 0.222039 11.000000 0.023710 0.023060 = 0.029550 -0.001160 0.013270 0.001520 C7 1 0.682026 0.641905 0.117636 11.000000 0.028210 0.020730 = 0.026800 -0.001130 0.012440 -0.002200 O4 4 0.106109 0.846241 0.104784 11.000000 0.064720 0.028040 = 0.056510 0.012500 0.047550 0.015560 AFIX 147 H4 2 0.040653 0.879045 0.127715 11.000000 -1.500000 AFIX 0 C5 1 0.471882 0.753338 0.068441 11.000000 0.040240 0.024930 = 0.029410 0.003800 0.019100 0.007260 AFIX 23 H5A 2 0.640303 0.772729 0.149282 11.000000 -1.200000 H5B 2 0.326703 0.737730 0.104094 11.000000 -1.200000 AFIX 0 C6 1 0.587988 0.696887 0.013342 11.000000 0.034730 0.023440 = 0.029390 0.002730 0.018090 0.003730 AFIX 23 H6B 2 0.430111 0.682334 -0.077750 11.000000 -1.200000 H6A 2 0.760444 0.710719 -0.004861 11.000000 -1.200000 AFIX 0 C3 1 0.207202 0.860820 0.008684 11.000000 0.026340 0.026190 = 0.026490 0.002320 0.012300 0.001670 C4 1 0.322312 0.804350 -0.044097 11.000000 0.043430 0.027210 = 0.032180 0.006240 0.022500 0.008860 AFIX 23 H4A 2 0.467464 0.819618 -0.080101 11.000000 -1.200000 H4B 2 0.153740 0.784851 -0.124684 11.000000 -1.200000 HKLF 4 REM REM R1 0.0415 FOR 1594 FO > 4SIG(FO) AND 0.0834 FOR ALL 2558 DATA REM 130 PARAMETERS REFINED USING 0 RESTRAINTS REM HIGHEST DIFFERENCE PEAK 0.210, DEEPEST HOLE -0.181, 1-SIGMA LEVEL 0.041 END ; _cod_data_source_file gp5050.cif _cod_data_source_block 225 _cod_original_cell_volume 951.6(2) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2105116 _cod_database_fobs_code 2105116 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 0.1297(3) 0.44519(5) 0.33441(10) 0.0314(3) Uani d . 1 1 O O5 0.6253(3) 0.64046(5) 0.22218(10) 0.0346(3) Uani d . 1 1 O O3 0.2033(3) 0.91561(5) -0.03396(10) 0.0296(3) Uani d . 1 1 N N1 0.5594(3) 0.52477(6) 0.33723(12) 0.0263(3) Uani d . 1 1 H H1A 0.6652 0.5561 0.3190 0.039 Uiso calc R 1 1 H H1B 0.6859 0.4987 0.4058 0.039 Uiso calc R 1 1 H H1C 0.4275 0.5422 0.3673 0.039 Uiso calc R 1 1 C C2 0.3944(3) 0.48745(7) 0.20527(14) 0.0251(3) Uani d . 1 1 H H2A 0.5387 0.4633 0.1809 0.030 Uiso calc R 1 1 H H2B 0.2864 0.5170 0.1261 0.030 Uiso calc R 1 1 O O6 0.8268(3) 0.59350(5) 0.09291(11) 0.0366(3) Uani d . 1 1 H H6 0.8563 0.6012 0.0205 0.055 Uiso calc R 1 1 O O2 0.0402(3) 0.40272(6) 0.12133(12) 0.0403(3) Uani d . 1 1 C C1 0.1715(3) 0.44119(7) 0.22204(14) 0.0247(3) Uani d . 1 1 C C7 0.6820(4) 0.64190(7) 0.11764(14) 0.0249(3) Uani d . 1 1 O O4 0.1061(3) 0.84624(5) 0.10478(13) 0.0423(3) Uani d . 1 1 H H4 0.0407 0.8790 0.1277 0.063 Uiso calc R 1 1 C C5 0.4719(4) 0.75334(7) 0.06844(14) 0.0300(4) Uani d . 1 1 H H5A 0.6403 0.7727 0.1493 0.036 Uiso calc R 1 1 H H5B 0.3267 0.7377 0.1041 0.036 Uiso calc R 1 1 C C6 0.5880(4) 0.69689(7) 0.01334(15) 0.0276(3) Uani d . 1 1 H H6B 0.4301 0.6823 -0.0778 0.033 Uiso calc R 1 1 H H6A 0.7604 0.7107 -0.0049 0.033 Uiso calc R 1 1 C C3 0.2072(3) 0.86082(7) 0.00868(14) 0.0259(3) Uani d . 1 1 C C4 0.3223(4) 0.80435(7) -0.04410(15) 0.0320(4) Uani d . 1 1 H H4A 0.4675 0.8196 -0.0801 0.038 Uiso calc R 1 1 H H4B 0.1537 0.7849 -0.1247 0.038 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 0.0382(7) 0.0317(6) 0.0323(5) -0.0113(5) 0.0225(5) -0.0052(4) O5 0.0512(8) 0.0277(6) 0.0338(5) 0.0037(5) 0.0266(5) 0.0051(4) O3 0.0376(7) 0.0217(5) 0.0332(5) 0.0002(5) 0.0183(5) 0.0016(4) N1 0.0308(7) 0.0234(6) 0.0295(6) -0.0054(6) 0.0173(5) 0.0006(5) C2 0.0259(8) 0.0269(7) 0.0255(6) -0.0005(7) 0.0136(6) 0.0002(6) O6 0.0515(8) 0.0273(6) 0.0376(6) 0.0121(6) 0.0251(6) 0.0044(5) O2 0.0431(8) 0.0427(7) 0.0421(6) -0.0173(6) 0.0249(6) -0.0182(5) C1 0.0237(8) 0.0231(7) 0.0296(7) 0.0015(6) 0.0133(6) -0.0012(6) C7 0.0282(9) 0.0207(7) 0.0268(6) -0.0022(6) 0.0124(6) -0.0011(5) O4 0.0647(9) 0.0280(6) 0.0565(7) 0.0156(6) 0.0475(7) 0.0125(5) C5 0.0402(10) 0.0249(8) 0.0294(7) 0.0073(7) 0.0191(7) 0.0038(6) C6 0.0347(9) 0.0234(7) 0.0294(7) 0.0037(7) 0.0181(6) 0.0027(6) C3 0.0263(8) 0.0262(7) 0.0265(7) 0.0017(7) 0.0123(6) 0.0023(6) C4 0.0434(11) 0.0272(8) 0.0322(7) 0.0089(7) 0.0225(7) 0.0062(6) 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 111.98(11) 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 125.24(14) O2 C1 C2 117.27(12) O1 C1 C2 117.49(12) O5 C7 O6 119.33(13) O5 C7 C6 122.19(13) O6 C7 C6 118.47(12) C3 O4 H4 109.5 C6 C5 C4 113.44(11) C6 C5 H5A 108.9 C4 C5 H5A 108.9 C6 C5 H5B 108.9 C4 C5 H5B 108.9 H5A C5 H5B 107.7 C7 C6 C5 112.19(11) C7 C6 H6B 109.2 C5 C6 H6B 109.2 C7 C6 H6A 109.2 C5 C6 H6A 109.2 H6B C6 H6A 107.9 O3 C3 O4 122.19(14) O3 C3 C4 123.87(13) O4 C3 C4 113.93(12) C3 C4 C5 114.22(11) C3 C4 H4A 108.7 C5 C4 H4A 108.7 C3 C4 H4B 108.7 C5 C4 H4B 108.7 H4A C4 H4B 107.6 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.2554(16) O5 C7 1.2159(17) O3 C3 1.2212(17) N1 C2 1.4766(18) N1 H1A 0.9000 N1 H1B 0.9000 N1 H1C 0.9000 C2 C1 1.518(2) C2 H2A 0.9800 C2 H2B 0.9800 O6 C7 1.3170(17) O6 H6 0.8300 O2 C1 1.2536(17) C7 C6 1.5042(19) O4 C3 1.3103(17) O4 H4 0.8300 C5 C6 1.515(2) C5 C4 1.516(2) C5 H5A 0.9800 C5 H5B 0.9800 C6 H6B 0.9800 C6 H6A 0.9800 C3 C4 1.501(2) C4 H4A 0.9800 C4 H4B 0.9800 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 0.90 2.11 2.9420(16) 154.0 N1 H1C O3 4_576 0.90 1.98 2.8716(16) 169.5 N1 H1A O5 . 0.90 1.99 2.7641(15) 143.2 O4 H4 O1 2 0.83 1.74 2.5650(15) 174.7 O6 H6 O2 3_665 0.83 1.73 2.5417(15) 164.9 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 -173.27(13) N1 C2 C1 O1 7.84(19) O5 C7 C6 C5 10.6(2) O6 C7 C6 C5 -170.43(14) C4 C5 C6 C7 -169.30(14) O3 C3 C4 C5 146.60(16) O4 C3 C4 C5 -34.2(2) C6 C5 C4 C3 -179.71(14) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654321