#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/29/2002981.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_2002981 loop_ _publ_author_name 'Rychlewska, Urszula' 'Szarecka, Agnieszka' 'Rychlewski, Jacek' 'Mota\/la, Rafa\/l' _publ_section_title ; A mediated hydrogen bond in an \a-hydroxycarboxyl group: X-ray structure of (R,R)-N-methyltartramic acid monohydrate and an ab initio study of model systems ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 617 _journal_page_last 625 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C5 H9 N1 O5,H2 O' _chemical_formula_sum 'C5 H11 N O6' _chemical_formula_weight 181.15 _chemical_name_common ; (R,R)-Tartaric Acid Mono (N-Methylamide) Monohydrate ; _chemical_name_systematic ; (R,R)-Tartaric Acid Mono (N-Methylamide) Monohydrate ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.3010(10) _cell_length_b 7.658(2) _cell_length_c 13.855(3) _cell_measurement_reflns_used 36 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.825 _cell_measurement_theta_min 8.42 _cell_volume 774.6(3) _computing_cell_refinement KM4 _computing_data_collection KM4 _computing_data_reduction DATARED _computing_molecular_graphics 'SIEMENS STEREOCHEMICAL WORKSTATION' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device KM-4 _diffrn_measurement_method theta-2theta _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 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2066 _diffrn_reflns_theta_max 28.06 _diffrn_reflns_theta_min 2.94 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type none _exptl_crystal_colour transparent _exptl_crystal_density_diffrn 1.553 _exptl_crystal_density_meas 1.533 _exptl_crystal_density_method 'flotation in KI' _exptl_crystal_description prism _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.183 _refine_diff_density_min -0.165 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.7(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.065 _refine_ls_goodness_of_fit_obs 1.063 _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1874 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.068 _refine_ls_restrained_S_obs 1.063 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_obs 0.0310 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.0586P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.0839 _refine_ls_wR_factor_obs 0.0737 _reflns_number_observed 1485 _reflns_number_total 1875 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file cf0006.cif _[local]_cod_data_source_block mma _[local]_cod_chemical_formula_sum_orig 'C5 H11 N1 O6' _cod_database_code 2002981 loop_ _symmetry_equiv_pos_as_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_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_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C1 0.2930(2) 0.4182(2) 0.41106(12) 0.0259(3) Uani d . 1 . C C2 0.5003(2) 0.4140(2) 0.40321(11) 0.0228(3) Uani d . 1 . C H2 0.5490(2) 0.3583(2) 0.45972(11) 0.027 Uiso d R 1 . H C3 0.5602(2) 0.3101(2) 0.31528(12) 0.0239(3) Uani d . 1 . C H3 0.5291(2) 0.1897(2) 0.32537(12) 0.029 Uiso d R 1 . H C4 0.7664(2) 0.3249(2) 0.30344(12) 0.0244(3) Uani d . 1 . C C40 1.0165(3) 0.3828(3) 0.19197(15) 0.0399(5) Uani d . 1 . C H401 1.0819(3) 0.4648(3) 0.23146(15) 0.048 Uiso d R 1 . H H402 1.0285(3) 0.4179(3) 0.12574(15) 0.048 Uiso d R 1 . H H403 1.0652(3) 0.2675(3) 0.20078(15) 0.048 Uiso d R 1 . H N4 0.8254(2) 0.3773(2) 0.21926(10) 0.0326(4) Uani d . 1 . N H4 0.7420(2) 0.4135(2) 0.17582(10) 0.039 Uiso d R 1 . H O1 0.2101(2) 0.5480(2) 0.43369(13) 0.0463(4) Uani d . 1 . O O2 0.5651(2) 0.5878(2) 0.40023(9) 0.0289(3) Uani d . 1 . O H2O 0.668(4) 0.601(4) 0.443(2) 0.070(8) Uiso d . 1 . H O3 0.4658(2) 0.3721(2) 0.23251(9) 0.0321(3) Uani d . 1 . O H3O 0.444(4) 0.284(4) 0.193(2) 0.075(9) Uiso d . 1 . H O4 0.8662(2) 0.2838(2) 0.37232(9) 0.0324(3) Uani d . 1 . O O10 0.2160(2) 0.2688(2) 0.39214(9) 0.0303(3) Uani d . 1 . O H10 0.088(5) 0.279(4) 0.377(3) 0.088(10) Uiso d . 1 . H O(W) 0.1486(2) 0.1173(2) 0.98452(10) 0.0358(3) Uani d . 1 . O H1W 0.047(4) 0.086(4) 1.005(2) 0.056(8) Uiso d . 1 . H H2W 0.138(5) 0.230(5) 0.969(3) 0.098(11) Uiso d . 1 . H 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 0.0232(8) 0.0306(9) 0.0240(8) 0.0014(7) -0.0001(6) 0.0001(7) C2 0.0219(7) 0.0246(8) 0.0218(7) 0.0011(6) -0.0025(6) 0.0000(6) C3 0.0192(7) 0.0253(8) 0.0270(8) 0.0009(6) -0.0024(7) -0.0023(6) C4 0.0208(8) 0.0232(8) 0.0294(8) 0.0009(6) 0.0012(6) -0.0044(7) C40 0.0295(9) 0.0530(12) 0.0371(10) -0.0018(9) 0.0075(8) 0.0070(9) N4 0.0238(8) 0.0443(9) 0.0296(8) 0.0010(7) 0.0000(6) 0.0033(7) O1 0.0257(7) 0.0388(8) 0.0744(11) 0.0029(6) 0.0065(7) -0.0184(7) O2 0.0253(6) 0.0257(6) 0.0358(7) -0.0029(5) -0.0058(5) -0.0049(5) O3 0.0278(7) 0.0423(8) 0.0262(6) 0.0034(6) -0.0062(5) -0.0059(6) O4 0.0203(6) 0.0462(7) 0.0309(6) 0.0019(6) -0.0017(5) 0.0048(5) O10 0.0219(6) 0.0306(6) 0.0384(7) -0.0012(5) -0.0007(5) 0.0013(5) O(W) 0.0307(7) 0.0369(8) 0.0398(7) 0.0012(7) -0.0033(6) 0.0097(6) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 C1 O10 124.1(2) O1 C1 C2 122.5(2) O10 C1 C2 113.44(14) O2 C2 C1 108.42(13) O2 C2 C3 111.93(14) C1 C2 C3 110.82(13) O2 C2 H2 108.58(8) C1 C2 H2 108.67(9) C3 C2 H2 108.35(9) O3 C3 C4 111.66(14) O3 C3 C2 109.47(13) C4 C3 C2 109.44(14) O3 C3 H3 108.89(9) C4 C3 H3 108.78(9) C2 C3 H3 108.54(9) O4 C4 N4 124.8(2) O4 C4 C3 118.7(2) N4 C4 C3 116.5(2) N4 C40 H401 110.50(11) N4 C40 H402 110.24(10) H401 C40 H402 108.5 N4 C40 H403 107.29(12) H401 C40 H403 110.2 H402 C40 H403 110.2 C4 N4 C40 124.1(2) C4 N4 H4 117.94(10) C40 N4 H4 117.97(10) C2 O2 H2O 109.8(19) C3 O3 H3O 110(2) C1 O10 H10 113(2) H1W O(W) H2W 106(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 O1 1.205(2) C1 O10 1.302(2) C1 C2 1.518(2) C2 O2 1.413(2) C2 C3 1.519(2) C2 H2 .96 C3 O3 1.419(2) C3 C4 1.519(2) C3 H3 .96 C4 O4 1.241(2) C4 N4 1.307(2) C40 N4 1.446(2) C40 H401 .96 C40 H402 .96 C40 H403 .96 N4 H4 .90 O2 H2O .96(3) O3 H3O .88(3) O10 H10 .96(3) O(W) H1W .83(3) O(W) H2W .89(4) 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 _geom_torsion_publ_flag O1 C1 C2 O2 -15.7(2) yes O10 C1 C2 O2 165.06(13) yes O1 C1 C2 C3 -138.9(2) yes O10 C1 C2 C3 41.8(2) yes O2 C2 C3 O3 -69.9(2) yes C1 C2 C3 O3 51.3(2) yes O2 C2 C3 C4 52.8(2) yes C1 C2 C3 C4 173.93(13) yes O3 C3 C4 O4 176.33(14) yes C2 C3 C4 O4 55.0(2) yes O3 C3 C4 N4 -5.1(2) yes C2 C3 C4 N4 -126.4(2) yes O4 C4 N4 C40 4.7(3) yes C3 C4 N4 C40 -173.8(2) yes