#------------------------------------------------------------------------------ #$Date: 2021-03-24 04:35:24 +0200 (Wed, 24 Mar 2021) $ #$Revision: 263279 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242509.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_7242509 loop_ _publ_author_name 'Yang, Jingxiang' 'Reiter, Ethan' 'Hu, Chunhua Tony' 'Kahr, Bart' _publ_section_title ; Ambient L-Lactic Acid Crystal Polymorphism ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D1CE00285F _journal_year 2021 _chemical_absolute_configuration syn _chemical_formula_sum 'C3 H6 O3' _chemical_formula_weight 90.08 _chemical_properties_physical Hygroscopic _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-10-30 deposited with the CCDC. 2021-03-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 5.7323(3) _cell_length_b 9.0190(5) _cell_length_c 17.3597(10) _cell_measurement_reflns_used 5183 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.22 _cell_measurement_theta_min 2.35 _cell_volume 897.49(9) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT (Sheldrick 2015)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_unetI/netI 0.0202 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 14087 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.294 _diffrn_reflns_theta_min 2.545 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.333 _exptl_crystal_description slab _exptl_crystal_F_000 384 _exptl_crystal_recrystallization_method 'From the Melt' _exptl_crystal_size_max 0.540 _exptl_crystal_size_mid 0.290 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.224 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.037 _refine_ls_abs_structure_details ; Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.6(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 126 _refine_ls_number_reflns 2237 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0283 _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^)+(0.0446P)^2^+0.0360P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.0717 _reflns_Friedel_coverage 0.691 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.998 _reflns_number_gt 2104 _reflns_number_total 2237 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ce00285f2.cif _cod_data_source_block 18bek42h _cod_database_code 7242509 _shelx_shelxl_version_number 2018/3 _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 0.938 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; TITL 18bek42h in P2(1)2(1)2(1) 18bek42h.res created by SHELXL-2018/3 at 23:25:57 on 06-Apr-2018 CELL 0.71073 5.73230 9.01900 17.35970 90.0000 90.0000 90.0000 ZERR 8.00 0.00030 0.00050 0.00100 0.0000 0.0000 0.0000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H O UNIT 24 48 24 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! SIZE 0.06 0.29 0.54 TEMP -173.150 OMIT 0 0 2 ! Affected by the beamstop L.S. 5 ACTA BOND $H HTAB FMAP 2 PLAN -20 WGHT 0.044600 0.036000 FVAR 0.25746 MOLE 1 O1 3 0.519848 0.670203 0.406024 11.00000 0.01423 0.02635 = 0.01715 0.00235 -0.00089 -0.00146 O2 3 0.664004 0.541831 0.505227 11.00000 0.01010 0.03059 = 0.02512 0.00715 -0.00054 0.00105 H2O 2 0.791323 0.570540 0.488874 11.00000 0.02862 O3 3 0.073038 0.623338 0.453382 11.00000 0.01116 0.02636 = 0.01544 -0.00030 -0.00141 0.00236 H3O 2 0.087775 0.595391 0.405946 11.00000 -1.50000 C1 1 0.492189 0.596530 0.463832 11.00000 0.01291 0.01782 = 0.01599 -0.00283 0.00006 -0.00066 C2 1 0.254557 0.553951 0.496085 11.00000 0.01044 0.02026 = 0.01517 -0.00030 -0.00055 0.00084 AFIX 13 H2 2 0.245976 0.591705 0.550174 11.00000 -1.20000 AFIX 0 C3 1 0.226306 0.386213 0.498853 11.00000 0.01889 0.02024 = 0.02681 0.00037 0.00076 -0.00130 AFIX 137 H3A 2 0.241816 0.345528 0.446758 11.00000 -1.50000 H3B 2 0.071924 0.361530 0.519436 11.00000 -1.50000 H3C 2 0.346992 0.343593 0.532147 11.00000 -1.50000 AFIX 0 MOLE 2 O4 3 0.064458 0.531881 0.304124 11.00000 0.02542 0.02664 = 0.01696 -0.00062 -0.00115 -0.00531 O5 3 0.052830 0.534502 0.175606 11.00000 0.02862 0.03096 = 0.01664 -0.00310 0.00014 -0.00948 H5O 2 -0.034040 0.459939 0.185281 11.00000 0.03732 O6 3 0.242147 0.815497 0.304143 11.00000 0.02653 0.01989 = 0.01867 -0.00032 -0.00707 0.00302 H6O 2 0.313505 0.770977 0.337952 11.00000 0.02737 C4 1 0.113292 0.589184 0.242820 11.00000 0.01363 0.02271 = 0.01840 -0.00309 -0.00125 0.00175 C5 1 0.255245 0.731065 0.235146 11.00000 0.02271 0.02140 = 0.01572 0.00056 -0.00329 -0.00090 AFIX 13 H5 2 0.186329 0.791416 0.192516 11.00000 -1.20000 AFIX 0 C6 1 0.506943 0.694327 0.213710 11.00000 0.02169 0.03535 = 0.02546 -0.00131 0.00368 -0.00613 AFIX 137 H6A 2 0.508953 0.635943 0.166103 11.00000 -1.50000 H6B 2 0.579027 0.636986 0.255337 11.00000 -1.50000 H6C 2 0.594445 0.786466 0.205927 11.00000 -1.50000 AFIX 0 HKLF 4 REM 18bek42h in P2(1)2(1)2(1) REM wR2 = 0.0717, GooF = S = 1.051, Restrained GooF = 1.051 for all data REM R1 = 0.0283 for 2104 Fo > 4sig(Fo) and 0.0304 for all 2237 data REM 126 parameters refined using 0 restraints END WGHT 0.0449 0.0348 REM Instructions for potential hydrogen bonds EQIV $1 x+1, y, z HTAB O2 O3_$1 HTAB O3 O4 EQIV $2 x-1/2, -y+3/2, -z+1 HTAB C2 O1_$2 EQIV $3 -x, y-1/2, -z+1/2 HTAB O5 O6_$3 HTAB O6 O1 EQIV $4 -x, y+1/2, -z+1/2 HTAB C5 O4_$4 HTAB C6 O1 REM Highest difference peak 0.224, deepest hole -0.171, 1-sigma level 0.037 Q1 1 0.3737 0.5735 0.4805 11.00000 0.05 0.22 Q2 1 0.1834 0.6670 0.2409 11.00000 0.05 0.21 Q3 1 0.2505 0.4705 0.5033 11.00000 0.05 0.16 Q4 1 0.0357 0.6070 0.3390 11.00000 0.05 0.15 Q5 1 0.6411 0.7059 0.3971 11.00000 0.05 0.14 Q6 1 -0.1367 0.3554 0.1846 11.00000 0.05 0.14 Q7 1 0.3754 0.6925 0.2327 11.00000 0.05 0.14 Q8 1 0.0330 0.4378 0.3022 11.00000 0.05 0.13 Q9 1 0.6404 0.6681 0.3834 11.00000 0.05 0.13 Q10 1 0.6524 0.4769 0.5380 11.00000 0.05 0.12 Q11 1 0.3938 0.6835 0.4030 11.00000 0.05 0.11 Q12 1 0.0440 0.5298 0.8069 11.00000 0.05 0.11 Q13 1 0.9572 0.6142 0.4728 11.00000 0.05 0.11 Q14 1 0.3459 0.3084 0.4056 11.00000 0.05 0.11 Q15 1 0.2636 0.6327 0.5401 11.00000 0.05 0.10 Q16 1 0.1206 0.7205 0.4472 11.00000 0.05 0.10 Q17 1 0.1336 0.4457 0.1780 11.00000 0.05 0.10 Q18 1 0.8294 0.6659 0.3944 11.00000 0.05 0.10 Q19 1 0.2482 0.7637 0.2592 11.00000 0.05 0.09 Q20 1 -0.2101 0.4091 0.1949 11.00000 0.05 0.09 ; _shelx_res_checksum 11471 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.51985(17) 0.67020(12) 0.40602(6) 0.0192(2) Uani 1 1 d . . . . . O2 O 0.66400(19) 0.54183(14) 0.50523(6) 0.0219(3) Uani 1 1 d . . . . . H2O H 0.791(4) 0.571(2) 0.4889(12) 0.029(5) Uiso 1 1 d . . . . . O3 O 0.07304(17) 0.62334(12) 0.45338(6) 0.0177(2) Uani 1 1 d . . . . . H3O H 0.088(4) 0.595(2) 0.4059(12) 0.026 Uiso 1 1 d . U . . . C1 C 0.4922(2) 0.59653(15) 0.46383(8) 0.0156(3) Uani 1 1 d . . . . . C2 C 0.2546(2) 0.55395(15) 0.49609(8) 0.0153(3) Uani 1 1 d . . . . . H2 H 0.245976 0.591705 0.550174 0.018 Uiso 1 1 calc R U . . . C3 C 0.2263(3) 0.38621(17) 0.49885(9) 0.0220(3) Uani 1 1 d . . . . . H3A H 0.241816 0.345528 0.446758 0.033 Uiso 1 1 calc R U . . . H3B H 0.071924 0.361530 0.519436 0.033 Uiso 1 1 calc R U . . . H3C H 0.346992 0.343593 0.532147 0.033 Uiso 1 1 calc R U . . . O4 O 0.0645(2) 0.53188(13) 0.30412(6) 0.0230(3) Uani 1 1 d . . . . . O5 O 0.0528(2) 0.53450(14) 0.17561(6) 0.0254(3) Uani 1 1 d . . . . . H5O H -0.034(4) 0.460(3) 0.1853(12) 0.037(6) Uiso 1 1 d . . . . . O6 O 0.2421(2) 0.81550(12) 0.30414(6) 0.0217(2) Uani 1 1 d . . . . . H6O H 0.314(4) 0.771(2) 0.3380(12) 0.027(5) Uiso 1 1 d . . . . . C4 C 0.1133(2) 0.58918(17) 0.24282(8) 0.0182(3) Uani 1 1 d . . . . . C5 C 0.2552(3) 0.73106(16) 0.23515(9) 0.0199(3) Uani 1 1 d . . . . . H5 H 0.186329 0.791416 0.192516 0.024 Uiso 1 1 calc R U . . . C6 C 0.5069(3) 0.6943(2) 0.21371(10) 0.0275(3) Uani 1 1 d . . . . . H6A H 0.508953 0.635943 0.166103 0.041 Uiso 1 1 calc R U . . . H6B H 0.579027 0.636986 0.255337 0.041 Uiso 1 1 calc R U . . . H6C H 0.594445 0.786466 0.205927 0.041 Uiso 1 1 calc R 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 O1 0.0142(5) 0.0263(5) 0.0171(5) 0.0024(4) -0.0009(4) -0.0015(4) O2 0.0101(5) 0.0306(6) 0.0251(6) 0.0071(5) -0.0005(4) 0.0011(4) O3 0.0112(4) 0.0264(6) 0.0154(5) -0.0003(4) -0.0014(4) 0.0024(4) C1 0.0129(6) 0.0178(6) 0.0160(6) -0.0028(5) 0.0001(5) -0.0007(5) C2 0.0104(6) 0.0203(7) 0.0152(6) -0.0003(6) -0.0006(5) 0.0008(5) C3 0.0189(6) 0.0202(7) 0.0268(7) 0.0004(6) 0.0008(6) -0.0013(6) O4 0.0254(6) 0.0266(5) 0.0170(5) -0.0006(4) -0.0011(4) -0.0053(5) O5 0.0286(6) 0.0310(6) 0.0166(5) -0.0031(5) 0.0001(4) -0.0095(6) O6 0.0265(5) 0.0199(5) 0.0187(5) -0.0003(4) -0.0071(5) 0.0030(5) C4 0.0136(6) 0.0227(7) 0.0184(7) -0.0031(6) -0.0012(5) 0.0018(5) C5 0.0227(7) 0.0214(7) 0.0157(6) 0.0006(5) -0.0033(6) -0.0009(6) C6 0.0217(8) 0.0353(8) 0.0255(7) -0.0013(7) 0.0037(6) -0.0061(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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O2 H2O 110.9(15) . . ? C2 O3 H3O 107.2(14) . . ? O1 C1 O2 124.00(13) . . ? O1 C1 C2 123.99(12) . . ? O2 C1 C2 112.00(11) . . ? O3 C2 C1 110.60(11) . . ? O3 C2 C3 112.07(11) . . ? C1 C2 C3 110.95(11) . . ? O3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C4 O5 H5O 106.0(14) . . ? C5 O6 H6O 108.3(14) . . ? O4 C4 O5 123.87(14) . . ? O4 C4 C5 123.85(13) . . ? O5 C4 C5 112.27(13) . . ? O6 C5 C4 110.39(12) . . ? O6 C5 C6 111.82(13) . . ? C4 C5 C6 110.13(13) . . ? O6 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? C6 C5 H5 108.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2140(17) . ? O2 C1 1.3152(17) . ? O2 H2O 0.82(2) . ? O3 C2 1.4226(16) . ? O3 H3O 0.87(2) . ? C1 C2 1.5220(19) . ? C2 C3 1.522(2) . ? C2 H2 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? O4 C4 1.2157(18) . ? O5 C4 1.3133(18) . ? O5 H5O 0.85(2) . ? O6 C5 1.4213(18) . ? O6 H6O 0.82(2) . ? C4 C5 1.522(2) . ? C5 C6 1.526(2) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ?