#------------------------------------------------------------------------------ #$Date: 2016-06-23 06:12:01 +0300 (Thu, 23 Jun 2016) $ #$Revision: 183858 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225609.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7225609 loop_ _publ_author_name 'Losev, Evgeniy' 'Zakharov, Boris' 'Boldyreva, Elena' _publ_section_title ; Polymorphic transformations in glycine co-crystals at low temperature and high pressure: two new examples as a follow-up to a glycine -- glutaric acid study ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C6CE00561F _journal_year 2016 _chemical_formula_moiety 'C4 H6 O6, C2 H5 N O2' _chemical_formula_sum 'C6 H11 N O8' _chemical_formula_weight 225.16 _chemical_name_common 'glycine-DL-tartaric acid (1:1)' _chemical_name_systematic 'glycine-DL-tartaric acid (1:1)' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-06-02 deposited with the CCDC. 2016-06-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.494(11) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.8563(7) _cell_length_b 9.3274(9) _cell_length_c 20.671(3) _cell_measurement_reflns_used 5284 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.40 _cell_measurement_theta_min 2.04 _cell_volume 910.5(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), ; _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'image plate (34 cm diameter)' _diffrn_detector_area_resol_mean 6.67 _diffrn_detector_type STOE _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_radiation_collimation '0.5 mm diameter, monocapillary' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_polarisn_norm 0 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_unetI/netI 0.0452 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.986 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 8609 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.986 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.275 _diffrn_reflns_theta_min 2.026 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_source_current 30 _diffrn_source_power 1.500 _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.643 _exptl_crystal_description block _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.390 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.193 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef 0.022(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 0.870 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 168 _refine_ls_number_reflns 2463 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.870 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0341 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0535P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.0957 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1383 _reflns_number_total 2463 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00561f17.cif _cod_data_source_block gta293K _cod_database_code 7225609 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.942 _shelx_estimated_absorpt_t_max 0.983 _shelx_res_file ; D:\IPDS\2014\glytart\cooling\293\deposit\new\new.res created by SHELXL-2014/7 TITL CELL 0.71073 4.85630 9.32740 20.67150 90.00000 103.49400 90.00000 ZERR 4 0.00070 0.00090 0.00280 0.00000 0.01100 0.00000 LATT 1 SYMM -X, Y+ 0.50000, -Z+ 0.50000 SFAC C H N O UNIT 24 44 4 32 EQIV $1 -1+X,+Y,+Z EQIV $2 2-X,-Y,1-Z EQIV $3 3-X,1-Y,1-Z EQIV $4 +X,0.5-Y,-0.5+Z EQIV $5 1-X,0.5+Y,0.5-Z EQIV $6 2-X,0.5+Y,0.5-Z L.S. 20 PLAN 30 SIZE 0.39 0.13 0.11 HTAB O6 O5_$1 HTAB O3 O2_$1 HTAB O5 O6_$2 HTAB O7 O1_$3 HTAB N1 O6_$4 HTAB N1 O8_$4 HTAB N1 O4_$5 HTAB N1 O2_$6 BOND $H CONF MORE -1 FMAP 2 ACTA REM TRANSFORMED TO SPACE GROUP : P21/C:B1 REM TRANSFORMED TO SPACE GROUP : P21/N:B2 REM REM REM REM REM REM WGHT 0.053500 EXTI 0.021972 FVAR 0.97513 O6 4 0.759721 0.122497 0.564300 11.00000 0.02429 0.03627 = 0.03991 0.00289 -0.00181 -0.00566 H6 2 0.573321 0.134597 0.541536 11.00000 -1.20000 O3 4 0.594809 0.354107 0.433148 11.00000 0.04420 0.04001 = 0.03813 0.00423 -0.00732 0.00804 H3 2 0.459342 0.359788 0.396070 11.00000 -1.20000 O5 4 1.213338 0.144276 0.493822 11.00000 0.02876 0.04189 = 0.04400 -0.00910 -0.00128 0.00311 H5 2 1.143403 0.077598 0.470232 11.00000 -1.20000 O8 4 1.221143 0.162212 0.662187 11.00000 0.03647 0.04951 = 0.04035 0.01219 -0.00628 -0.00847 O7 4 1.324009 0.366547 0.616161 11.00000 0.04592 0.04449 = 0.04198 0.00478 -0.01133 -0.01961 AFIX 147 H7 2 1.462322 0.366665 0.647727 11.00000 -1.20000 AFIX 0 O4 4 0.742045 0.148922 0.395424 11.00000 0.04137 0.04751 = 0.03928 -0.00953 -0.00509 0.00032 O1 4 1.229506 0.582980 0.292867 11.00000 0.03460 0.03669 = 0.04621 -0.00189 -0.00889 -0.00656 C3 1 0.768037 0.247225 0.435055 11.00000 0.03156 0.03175 = 0.03058 0.00395 0.00215 -0.00367 O2 4 1.178881 0.362738 0.331486 11.00000 0.04473 0.04460 = 0.04789 0.01139 -0.01188 -0.00032 C5 1 0.915803 0.249187 0.560192 11.00000 0.02556 0.02811 = 0.03367 -0.00026 0.00012 -0.00020 H5A 2 0.807416 0.330894 0.562678 11.00000 -1.20000 C2 1 1.101486 0.466918 0.293208 11.00000 0.02633 0.03276 = 0.03155 -0.00321 0.00059 0.00258 C6 1 1.170152 0.252810 0.619266 11.00000 0.02805 0.03241 = 0.03094 -0.00359 0.00392 -0.00243 C4 1 1.016979 0.255428 0.494998 11.00000 0.02873 0.02970 = 0.03312 0.00008 0.00002 -0.00258 H4 2 1.107030 0.344774 0.492888 11.00000 -1.20000 N1 3 0.798287 0.548026 0.186584 11.00000 0.03811 0.03825 = 0.03500 -0.00315 -0.00881 0.00839 H1A 2 0.613972 0.568036 0.164451 11.00000 -1.50000 H1B 2 0.861175 0.632267 0.200761 11.00000 -1.50000 H1C 2 0.898048 0.506875 0.159703 11.00000 -1.50000 C1 1 0.820040 0.450110 0.243571 11.00000 0.02629 0.03996 = 0.03620 -0.00428 -0.00111 0.00162 H1D 2 0.676902 0.474119 0.263458 11.00000 -1.20000 H1E 2 0.793901 0.352172 0.227813 11.00000 -1.20000 HKLF 4 REM REM R1 = 0.0341 for 1383 Fo > 4sig(Fo) and 0.0774 for all 2463 data REM 168 parameters refined using 0 restraints END WGHT 0.0535 0.0000 REM Highest difference peak 0.193, deepest hole -0.215, 1-sigma level 0.045 Q1 1 0.9716 0.2586 0.5278 11.00000 0.05 0.19 Q2 1 1.0475 0.4169 0.1885 11.00000 0.05 0.19 Q3 1 1.1119 0.4185 0.3499 11.00000 0.05 0.18 Q4 1 1.0779 0.2186 0.5027 11.00000 0.05 0.18 Q5 1 0.9225 0.2165 0.4676 11.00000 0.05 0.17 Q6 1 1.5521 0.4276 0.6594 11.00000 0.05 0.16 Q7 1 1.2546 0.5190 0.3511 11.00000 0.05 0.16 Q8 1 1.0734 0.1068 0.6533 11.00000 0.05 0.15 Q9 1 1.0725 0.2534 0.3317 11.00000 0.05 0.15 Q10 1 0.6378 0.1271 0.4313 11.00000 0.05 0.15 Q11 1 0.2463 0.4005 0.3876 11.00000 0.05 0.15 Q12 1 0.9248 0.1602 0.6610 11.00000 0.05 0.15 Q13 1 1.1863 0.6331 0.2787 11.00000 0.05 0.14 Q14 1 0.4876 0.0517 0.4279 11.00000 0.05 0.14 Q15 1 0.4519 0.4941 0.1100 11.00000 0.05 0.14 Q16 1 1.3105 0.6568 0.3326 11.00000 0.05 0.14 Q17 1 0.7267 0.1186 0.3823 11.00000 0.05 0.14 Q18 1 0.6178 0.5063 0.1391 11.00000 0.05 0.14 Q19 1 0.4171 0.4684 0.3746 11.00000 0.05 0.14 Q20 1 0.7370 0.3655 0.4088 11.00000 0.05 0.13 Q21 1 1.0373 0.5509 0.2367 11.00000 0.05 0.13 Q22 1 0.5026 0.1217 0.3962 11.00000 0.05 0.13 Q23 1 0.9938 0.4262 0.2708 11.00000 0.05 0.13 Q24 1 1.2375 0.1286 0.6732 11.00000 0.05 0.13 Q25 1 1.2038 0.5084 0.2349 11.00000 0.05 0.13 Q26 1 1.3720 0.4796 0.6451 11.00000 0.05 0.13 Q27 1 1.2190 0.0782 0.7088 11.00000 0.05 0.13 Q28 1 0.8197 0.2272 0.2245 11.00000 0.05 0.13 Q29 1 1.1958 0.3224 0.3454 11.00000 0.05 0.13 Q30 1 0.6247 0.4608 0.3978 11.00000 0.05 0.13 ; _shelx_res_checksum 28620 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O6 O 0.7597(2) 0.12250(11) 0.56430(5) 0.0350(3) Uani 1 1 d . . H6 H 0.573(4) 0.1346(18) 0.5415(9) 0.042 Uiso 1 1 d . U O3 O 0.5948(3) 0.35411(12) 0.43315(6) 0.0436(3) Uani 1 1 d . . H3 H 0.459(4) 0.360(2) 0.3961(10) 0.052 Uiso 1 1 d . U O5 O 1.2133(2) 0.14428(13) 0.49382(6) 0.0398(3) Uani 1 1 d . . H5 H 1.143(4) 0.078(2) 0.4702(9) 0.048 Uiso 1 1 d . U O8 O 1.2211(2) 0.16221(13) 0.66219(6) 0.0446(3) Uani 1 1 d . . O7 O 1.3240(3) 0.36655(13) 0.61616(6) 0.0477(3) Uani 1 1 d . . H7 H 1.4623 0.3667 0.6477 0.057 Uiso 1 1 calc R U O4 O 0.7420(2) 0.14892(13) 0.39542(6) 0.0451(3) Uani 1 1 d . . O1 O 1.2295(2) 0.58298(12) 0.29287(6) 0.0422(3) Uani 1 1 d . . C3 C 0.7680(3) 0.24723(15) 0.43505(7) 0.0321(3) Uani 1 1 d . . O2 O 1.1789(3) 0.36274(13) 0.33149(6) 0.0495(3) Uani 1 1 d . . C5 C 0.9158(3) 0.24919(16) 0.56019(7) 0.0302(3) Uani 1 1 d . . H5A H 0.807(4) 0.3309(18) 0.5627(8) 0.036 Uiso 1 1 d . U C2 C 1.1015(3) 0.46692(15) 0.29321(7) 0.0312(3) Uani 1 1 d . . C6 C 1.1702(3) 0.25281(16) 0.61927(7) 0.0310(3) Uani 1 1 d . . C4 C 1.0170(3) 0.25543(16) 0.49500(7) 0.0317(3) Uani 1 1 d . . H4 H 1.107(4) 0.3448(19) 0.4929(8) 0.038 Uiso 1 1 d . U N1 N 0.7983(3) 0.54803(16) 0.18658(7) 0.0400(3) Uani 1 1 d . . H1A H 0.614(5) 0.568(2) 0.1645(10) 0.060 Uiso 1 1 d . U H1B H 0.861(5) 0.632(2) 0.2008(10) 0.060 Uiso 1 1 d . U H1C H 0.898(4) 0.507(2) 0.1597(10) 0.060 Uiso 1 1 d . U C1 C 0.8200(3) 0.45011(18) 0.24357(8) 0.0355(4) Uani 1 1 d . . H1D H 0.677(4) 0.4741(18) 0.2635(8) 0.043 Uiso 1 1 d . U H1E H 0.794(4) 0.352(2) 0.2278(9) 0.043 Uiso 1 1 d . U loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O6 0.0243(5) 0.0363(6) 0.0399(6) 0.0029(5) -0.0018(5) -0.0057(5) O3 0.0442(7) 0.0400(6) 0.0381(6) 0.0042(5) -0.0073(5) 0.0080(6) O5 0.0288(6) 0.0419(6) 0.0440(6) -0.0091(5) -0.0013(5) 0.0031(5) O8 0.0365(6) 0.0495(7) 0.0404(6) 0.0122(5) -0.0063(5) -0.0085(5) O7 0.0459(7) 0.0445(7) 0.0420(6) 0.0048(5) -0.0113(5) -0.0196(6) O4 0.0414(7) 0.0475(7) 0.0393(6) -0.0095(5) -0.0051(5) 0.0003(5) O1 0.0346(6) 0.0367(6) 0.0462(7) -0.0019(5) -0.0089(5) -0.0066(5) C3 0.0316(8) 0.0317(7) 0.0306(7) 0.0040(7) 0.0022(6) -0.0037(6) O2 0.0447(7) 0.0446(7) 0.0479(7) 0.0114(6) -0.0119(6) -0.0003(6) C5 0.0256(7) 0.0281(7) 0.0337(8) -0.0003(6) 0.0001(6) -0.0002(6) C2 0.0263(7) 0.0328(7) 0.0316(7) -0.0032(6) 0.0006(6) 0.0026(6) C6 0.0280(8) 0.0324(7) 0.0309(7) -0.0036(6) 0.0039(6) -0.0024(6) C4 0.0287(8) 0.0297(7) 0.0331(7) 0.0001(6) 0.0000(6) -0.0026(6) N1 0.0381(8) 0.0382(8) 0.0350(7) -0.0031(6) -0.0088(6) 0.0084(6) C1 0.0263(7) 0.0400(9) 0.0362(8) -0.0043(7) -0.0011(6) 0.0016(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 C5 O6 H6 110.0(11) C3 O3 H3 114.6(12) C4 O5 H5 112.5(14) C6 O7 H7 109.5 O4 C3 O3 126.40(14) O4 C3 C4 121.71(13) O3 C3 C4 111.89(13) O6 C5 C6 108.41(12) O6 C5 C4 111.62(12) C6 C5 C4 109.67(12) O6 C5 H5A 111.1(10) C6 C5 H5A 107.5(11) C4 C5 H5A 108.4(10) O1 C2 O2 126.78(14) O1 C2 C1 117.25(13) O2 C2 C1 115.96(13) O8 C6 O7 125.58(14) O8 C6 C5 124.25(13) O7 C6 C5 110.17(12) O5 C4 C3 111.18(12) O5 C4 C5 109.99(12) C3 C4 C5 110.89(12) O5 C4 H4 108.9(10) C3 C4 H4 107.2(10) C5 C4 H4 108.6(10) C1 N1 H1A 113.6(12) C1 N1 H1B 109.7(14) H1A N1 H1B 102.0(19) C1 N1 H1C 106.2(13) H1A N1 H1C 112.2(18) H1B N1 H1C 113(2) N1 C1 C2 111.25(13) N1 C1 H1D 106.7(11) C2 C1 H1D 109.3(11) N1 C1 H1E 109.6(11) C2 C1 H1E 110.6(11) H1D C1 H1E 109.2(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O6 C5 1.4171(18) O6 H6 0.92(2) O3 C3 1.2991(18) O3 H3 0.89(2) O5 C4 1.4127(19) O5 H5 0.81(2) O8 C6 1.2083(18) O7 C6 1.3078(18) O7 H7 0.8200 O4 C3 1.2164(18) O1 C2 1.2492(18) C3 C4 1.518(2) O2 C2 1.2541(18) C5 C6 1.521(2) C5 C4 1.539(2) C5 H5A 0.934(17) C2 C1 1.514(2) C4 H4 0.947(18) N1 C1 1.475(2) N1 H1A 0.92(2) N1 H1B 0.87(2) N1 H1C 0.90(2) C1 H1D 0.914(18) C1 H1E 0.968(18) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6 O5 0.92(2) 1.80(2) 2.7203(16) 175.2(16) 1_455 O3 H3 O2 0.89(2) 1.67(2) 2.5538(17) 173.3(19) 1_455 O5 H5 O6 0.81(2) 2.091(19) 2.7795(16) 142.3(18) 3_756 O7 H7 O1 0.82 1.76 2.5606(16) 163.5 3_866 N1 H1C O6 0.90(2) 2.28(2) 2.9553(18) 131.8(17) 4_565 N1 H1C O8 0.90(2) 2.22(2) 2.9665(19) 140.0(17) 4_565 N1 H1A O4 0.92(2) 2.02(2) 2.9273(19) 165.7(18) 2_655 N1 H1B O2 0.87(2) 2.25(2) 2.9645(19) 140.0(18) 2_755 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 O6 C5 C6 O8 -1.2(2) C4 C5 C6 O8 -123.29(16) O6 C5 C6 O7 178.24(12) C4 C5 C6 O7 56.14(17) O4 C3 C4 O5 5.0(2) O3 C3 C4 O5 -175.83(12) O4 C3 C4 C5 -117.70(16) O3 C3 C4 C5 61.46(16) O6 C5 C4 O5 -65.36(16) C6 C5 C4 O5 54.81(16) O6 C5 C4 C3 58.04(16) C6 C5 C4 C3 178.20(12) O1 C2 C1 N1 22.8(2) O2 C2 C1 N1 -158.61(14)