#------------------------------------------------------------------------------ #$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176768 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/10/54/2105494.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_2105494 loop_ _publ_author_name 'Herman, Christelle' 'Vermylen, Val\'erie' 'Norberg, Bernadette' 'Wouters, Johan' 'Leyssens, Tom' _publ_section_title ; The importance of screening solid-state phases of a racemic modification of a chiral drug: thermodynamic and structural characterization of solid-state phases of etiracetam ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 371 _journal_page_last 378 _journal_paper_doi 10.1107/S2052519213015054 _journal_volume 69 _journal_year 2013 _chemical_formula_moiety 'C8 H14 N2 O2, H2 O' _chemical_formula_sum 'C8 H16 N2 O3' _chemical_formula_weight 188.23 _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 85.293(5) _cell_angle_beta 76.031(6) _cell_angle_gamma 70.023(6) _cell_formula_units_Z 2 _cell_length_a 7.2006(5) _cell_length_b 7.9639(5) _cell_length_c 9.5468(6) _cell_measurement_reflns_used 2333 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.5884 _cell_measurement_theta_min 3.3543 _cell_volume 499.30(6) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.3712 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.900 _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5863 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 32.66 _diffrn_reflns_theta_min 3.36 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 204 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.242 _refine_diff_density_min -0.206 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 135 _refine_ls_number_reflns 3290 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.939 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0470 _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^)+(0.0762P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1243 _refine_ls_wR_factor_ref 0.1337 _reflns_number_gt 2015 _reflns_number_total 3290 _reflns_threshold_expression >2sigma(I) _cod_data_source_file zb5029.cif _cod_data_source_block Etiracetam_Hydrate _cod_database_code 2105494 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 C C1 0.64229(18) 0.12134(16) 0.59858(13) 0.0423(3) Uani d . 1 1 C C2 0.7691(2) -0.06906(18) 0.61925(17) 0.0581(4) Uani d . 1 1 H H2A 0.9090 -0.0918 0.5675 0.070 Uiso calc R 1 1 H H2B 0.7170 -0.1513 0.5849 0.070 Uiso calc R 1 1 C C3 0.7538(2) -0.08979(18) 0.78088(17) 0.0565(4) Uani d . 1 1 H H3A 0.8850 -0.1570 0.8010 0.068 Uiso calc R 1 1 H H3B 0.6581 -0.1506 0.8247 0.068 Uiso calc R 1 1 C C4 0.68020(19) 0.10033(17) 0.83719(14) 0.0450(3) Uani d . 1 1 H H4A 0.5826 0.1134 0.9290 0.054 Uiso calc R 1 1 H H4B 0.7926 0.1345 0.8488 0.054 Uiso calc R 1 1 C C5 0.48294(15) 0.39969(14) 0.73852(11) 0.0329(2) Uani d . 1 1 H H5 0.4541 0.4428 0.6443 0.039 Uiso calc R 1 1 C C6 0.27817(15) 0.44750(15) 0.84804(12) 0.0343(2) Uani d . 1 1 C C7 0.61868(17) 0.49527(16) 0.77067(14) 0.0431(3) Uani d . 1 1 H H7A 0.6497 0.4566 0.8639 0.052 Uiso calc R 1 1 H H7B 0.5464 0.6229 0.7759 0.052 Uiso calc R 1 1 C C8 0.8161(2) 0.4582(2) 0.65597(17) 0.0574(4) Uani d . 1 1 H H8A 0.8912 0.3326 0.6537 0.086 Uiso calc R 1 1 H H8B 0.8954 0.5233 0.6786 0.086 Uiso calc R 1 1 H H8C 0.7861 0.4954 0.5634 0.086 Uiso calc R 1 1 N N1 0.58525(13) 0.20777(12) 0.72503(9) 0.0328(2) Uani d . 1 1 N N2 0.19197(16) 0.32228(15) 0.88046(13) 0.0457(3) Uani d . 1 1 O O1 0.59756(19) 0.19044(14) 0.48629(10) 0.0669(3) Uani d . 1 1 O O2 0.19811(12) 0.59925(11) 0.90024(10) 0.0470(2) Uani d . 1 1 O O3 0.24206(17) -0.04415(15) 0.79030(14) 0.0612(3) Uani d . 1 1 H H2C 0.074(3) 0.350(2) 0.9484(18) 0.062(4) Uiso d . 1 1 H H2D 0.244(2) 0.217(2) 0.8393(17) 0.056(4) Uiso d . 1 1 H H3C 0.219(3) -0.141(3) 0.835(2) 0.101(7) Uiso d . 1 1 H H3D 0.287(3) -0.087(3) 0.703(2) 0.080(6) Uiso d . 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 C1 0.0467(6) 0.0387(6) 0.0358(6) -0.0147(5) 0.0039(5) -0.0065(5) C2 0.0600(8) 0.0349(7) 0.0634(9) -0.0104(6) 0.0104(7) -0.0088(6) C3 0.0514(8) 0.0395(7) 0.0757(10) -0.0096(6) -0.0190(7) 0.0056(7) C4 0.0459(7) 0.0435(7) 0.0429(7) -0.0115(5) -0.0122(5) 0.0070(5) C5 0.0322(5) 0.0309(5) 0.0291(5) -0.0063(4) -0.0004(4) -0.0023(4) C6 0.0300(5) 0.0360(6) 0.0321(5) -0.0069(4) -0.0036(4) -0.0017(4) C7 0.0363(6) 0.0374(6) 0.0515(7) -0.0130(5) 0.0018(5) -0.0091(5) C8 0.0393(7) 0.0526(8) 0.0722(10) -0.0180(6) 0.0071(6) -0.0026(7) N1 0.0323(4) 0.0297(5) 0.0311(5) -0.0067(3) -0.0025(4) -0.0015(4) N2 0.0349(5) 0.0408(6) 0.0546(7) -0.0134(4) 0.0067(5) -0.0105(5) O1 0.1057(9) 0.0562(6) 0.0325(5) -0.0205(6) -0.0116(5) -0.0066(4) O2 0.0395(4) 0.0366(5) 0.0529(5) -0.0074(3) 0.0070(4) -0.0087(4) O3 0.0726(7) 0.0530(6) 0.0564(7) -0.0241(5) -0.0016(5) -0.0163(5) 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 O1 C1 N1 124.36(12) O1 C1 C2 127.01(12) N1 C1 C2 108.63(11) C1 C2 C3 105.22(11) C1 C2 H2A 110.7 C3 C2 H2A 110.7 C1 C2 H2B 110.7 C3 C2 H2B 110.7 H2A C2 H2B 108.8 C2 C3 C4 104.63(11) C2 C3 H3A 110.8 C4 C3 H3A 110.8 C2 C3 H3B 110.8 C4 C3 H3B 110.8 H3A C3 H3B 108.9 N1 C4 C3 103.67(10) N1 C4 H4A 111.0 C3 C4 H4A 111.0 N1 C4 H4B 111.0 C3 C4 H4B 111.0 H4A C4 H4B 109.0 N1 C5 C7 111.85(9) N1 C5 C6 112.16(9) C7 C5 C6 111.99(9) N1 C5 H5 106.8 C7 C5 H5 106.8 C6 C5 H5 106.8 O2 C6 N2 122.57(10) O2 C6 C5 119.90(10) N2 C6 C5 117.51(10) C5 C7 C8 112.04(10) C5 C7 H7A 109.2 C8 C7 H7A 109.2 C5 C7 H7B 109.2 C8 C7 H7B 109.2 H7A C7 H7B 107.9 C7 C8 H8A 109.5 C7 C8 H8B 109.5 H8A C8 H8B 109.5 C7 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C1 N1 C5 122.66(10) C1 N1 C4 113.10(10) C5 N1 C4 122.51(9) C6 N2 H2C 117.1(10) C6 N2 H2D 123.1(9) H2C N2 H2D 119.8(14) H3C O3 H3D 97.8(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.2265(17) C1 N1 1.3430(15) C1 C2 1.5046(19) C2 C3 1.520(2) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.5199(18) C3 H3A 0.9700 C3 H3B 0.9700 C4 N1 1.4661(15) C4 H4A 0.9700 C4 H4B 0.9700 C5 N1 1.4535(13) C5 C7 1.5234(16) C5 C6 1.5329(14) C5 H5 0.9800 C6 O2 1.2351(13) C6 N2 1.3248(16) C7 C8 1.5238(16) C7 H7A 0.9700 C7 H7B 0.9700 C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 N2 H2C 0.906(17) N2 H2D 0.877(17) O3 H3C 0.90(3) O3 H3D 0.87(2) 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 O1 C1 C2 C3 -172.82(13) N1 C1 C2 C3 7.85(15) C1 C2 C3 C4 -18.25(15) C2 C3 C4 N1 21.53(13) N1 C5 C6 O2 160.91(10) C7 C5 C6 O2 34.20(15) N1 C5 C6 N2 -20.47(14) C7 C5 C6 N2 -147.19(11) N1 C5 C7 C8 57.15(13) C6 C5 C7 C8 -175.96(10) O1 C1 N1 C5 -7.39(19) C2 C1 N1 C5 171.96(10) O1 C1 N1 C4 -172.75(12) C2 C1 N1 C4 6.60(14) C7 C5 N1 C1 -110.21(12) C6 C5 N1 C1 122.99(11) C7 C5 N1 C4 53.78(13) C6 C5 N1 C4 -73.01(12) C3 C4 N1 C1 -18.14(13) C3 C4 N1 C5 176.48(9)