#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202396.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_2202396 loop_ _publ_author_name 'Takeo Fukunaga' 'Hiroyuki Ishida' _publ_section_title ; Imidazolium hydrogen tartronate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1869 _journal_page_last o1871 _journal_paper_doi 10.1107/S1600536803024723 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C3 H5 N2 1+, C3 H3 O5 1- ' _chemical_formula_sum 'C6 H8 N2 O5' _chemical_formula_weight 188.14 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yab' _symmetry_space_group_name_H-M 'P 1 21/a 1' _atom_type_scat_source IntTabC _cell_angle_alpha 90 _cell_angle_beta 91.64(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.5516(15) _cell_length_b 10.2077(17) _cell_length_c 9.392(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298 _cell_measurement_theta_max 11.5 _cell_measurement_theta_min 11.1 _cell_volume 819.5(3) _computing_cell_refinement ; MSC/AFC Diffractometer Control Software ; _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990) ; _computing_data_reduction ; TEXSAN for Windows (Molecular Structure Corporation, 1997--1999) ; _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'TEXSAN for Windows' _computing_structure_refinement 'TEXSAN for Windows' _computing_structure_solution ; SIR92 (Altomare et al., 1994) ; _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'Rigaku AFC-5R' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.021 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 6785 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_full 31.00 _diffrn_reflns_theta_max 31.0 _diffrn_reflns_theta_min 2.17 _diffrn_standards_decay_% 4.2 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.13 _exptl_absorpt_correction_T_max 0.95 _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_meas ? _exptl_crystal_description prismatic _exptl_crystal_F_000 392.00 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.36 _refine_diff_density_min -0.27 _refine_ls_extinction_coef 1.43E-5(12) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) 24, p. 213.' _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_all 1.01 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 151 _refine_ls_number_reflns 2617 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.065 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00181|Fo|^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_all 0.120 _refine_ls_wR_factor_ref 0.120 _reflns_number_gt 2032 _reflns_number_total 2617 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6367.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 819.6(3) _cod_original_sg_symbol_H-M 'P 21/a' _cod_original_formula_sum 'C6 H8 N2 O5 ' _cod_database_code 2202396 _cod_database_fobs_code 2202396 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y, -z' ' -x, -y, -z' '1/2+x,1/2-y, +z' loop_ _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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy O1 0.59735(10) 0.28719(8) 0.24917(9) 0.0351(2) Uani d ? . 1.000 O2 0.43495(10) 0.06705(8) 0.21603(8) 0.0364(2) Uani d ? . 1.000 O3 0.34469(10) 0.12441(7) -0.00186(7) 0.03182(19) Uani d ? . 1.000 O4 0.31606(10) 0.41559(8) 0.00493(7) 0.0355(2) Uani d ? . 1.000 O5 0.34176(11) 0.43865(8) 0.23900(8) 0.0378(2) Uani d ? . 1.000 N1 0.37412(14) 0.34483(11) 0.50833(10) 0.0396(3) Uani d ? . 1.000 N2 0.35097(14) 0.31784(11) 0.73300(10) 0.0397(3) Uani d ? . 1.000 C1 0.34872(16) 0.40520(12) 0.62979(12) 0.0388(3) Uani d ? . 1.000 C2 0.3781(3) 0.19715(14) 0.67617(14) 0.0563(4) Uani d ? . 1.000 C3 0.3926(2) 0.21421(13) 0.53549(14) 0.0547(4) Uani d ? . 1.000 C4 0.50116(11) 0.27806(9) 0.12526(10) 0.0243(2) Uani d ? . 1.000 C5 0.42193(11) 0.14398(9) 0.11786(10) 0.0244(2) Uani d ? . 1.000 C6 0.37693(11) 0.38707(9) 0.12497(9) 0.0236(2) Uani d ? . 1.000 H1 0.378(2) 0.3793(17) 0.4202(16) 0.059(5) Uiso d ? . 1.000 H2 0.329(2) 0.4929(18) 0.6482(14) 0.054(5) Uiso d ? . 1.000 H3 0.335(2) 0.333(2) 0.8282(19) 0.072(5) Uiso d ? . 1.000 H4 0.380(3) 0.116(2) 0.7324(19) 0.081(6) Uiso d ? . 1.000 H5 0.414(2) 0.1576(18) 0.4577(17) 0.063(5) Uiso d ? . 1.000 H6 0.5608(16) 0.2867(13) 0.0383(14) 0.029(3) Uiso d ? . 1.000 H7 0.616(2) 0.208(2) 0.2794(19) 0.074(6) Uiso d ? . 1.000 H8 0.300(2) 0.0466(17) -0.0009(15) 0.052(4) Uiso d ? . 1.000 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 0.0334(4) 0.0333(4) 0.0377(4) 0.0012(3) -0.0137(3) -0.0020(3) O2 0.0468(5) 0.0279(4) 0.0341(4) 0.0025(3) -0.0050(3) 0.0071(3) O3 0.0440(5) 0.0261(4) 0.0251(3) -0.0073(3) -0.0032(3) -0.0019(3) O4 0.0534(5) 0.0317(4) 0.0210(3) 0.0143(3) -0.0066(3) -0.0006(3) O5 0.0505(5) 0.0414(4) 0.0217(3) 0.0169(4) 0.0002(3) -0.0024(3) N1 0.0550(6) 0.0413(5) 0.0224(4) -0.0055(5) -0.0011(4) 0.0025(4) N2 0.0560(6) 0.0423(5) 0.0210(4) 0.0017(5) 0.0019(4) -0.0023(4) C1 0.0499(7) 0.0359(6) 0.0305(5) 0.0008(5) -0.0019(5) -0.0013(4) C2 0.0999(13) 0.0369(6) 0.0326(6) 0.0043(7) 0.0140(7) 0.0045(5) C3 0.0977(13) 0.0368(6) 0.0303(6) -0.0043(7) 0.0150(7) -0.0051(5) C4 0.0247(4) 0.0241(4) 0.0241(4) 0.0000(3) -0.0013(3) -0.0009(3) C5 0.0256(4) 0.0224(4) 0.0252(4) 0.0035(3) 0.0021(3) -0.0022(3) C6 0.0286(4) 0.0207(4) 0.0215(4) -0.0005(3) -0.0010(3) 0.0016(3) loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 0 0 -4 0 0 0 -4 2 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C4 O1 H7 107.7(13) no C5 O3 H8 109.9(10) no C1 N1 C3 108.38(10) yes C1 N1 H1 128.6(11) no C3 N1 H1 123.0(11) no C1 N2 C2 108.80(10) yes C1 N2 H3 127.1(13) no C2 N2 H3 124.1(13) no N1 C1 N2 108.71(11) yes N1 C1 H2 130.3(9) no N2 C1 H2 121.0(9) no N2 C2 C3 106.82(12) yes N2 C2 H4 123.4(11) no C3 C2 H4 129.7(11) no N1 C3 C2 107.28(12) yes N1 C3 H5 118.2(11) no C2 C3 H5 134.5(11) no O1 C4 C5 110.15(8) yes O1 C4 C6 109.90(8) no O1 C4 H6 112.2(8) no C5 C4 C6 110.03(8) no C5 C4 H6 106.5(8) no C6 C4 H6 108.0(8) no O2 C5 O3 126.13(9) yes O2 C5 C4 120.93(9) no O3 C5 C4 112.94(8) yes O4 C6 O5 124.77(9) yes O4 C6 C4 115.82(8) no O5 C6 C4 119.40(8) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C4 . . 1.4089(12) yes O1 H7 . . 0.87(2) no O2 C5 . . 1.2138(12) yes O3 C5 . . 1.3031(12) yes O3 H8 . . 0.883(18) no O4 C6 . . 1.2622(12) yes O5 C6 . . 1.2383(12) yes N1 C1 . . 1.3200(15) yes N1 C3 . . 1.3659(18) yes N1 H1 . . 0.901(15) no N2 C1 . . 1.3169(15) yes N2 C2 . . 1.3651(18) yes N2 H3 . . 0.920(18) no C1 H2 . . 0.927(18) no C2 C3 . . 1.3420(18) yes C2 H4 . . 0.98(2) no C3 H5 . . 0.953(17) no C4 C5 . . 1.5279(13) yes C4 C6 . . 1.5384(13) yes C4 H6 . . 0.980(13) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 H1 2.672(17) . no O1 C5 3.1489(14) 4 no O1 N1 3.1909(16) . no O1 C6 3.2250(13) 4 no O1 C3 3.335(2) . no O2 H2 2.734(17) 2_546 no O2 C2 3.2806(18) 3_656 no O3 H6 2.629(13) 4_455 no O3 H3 2.66(2) 1_554 no O3 N2 3.1798(15) 1_554 no O3 C6 3.2669(12) 2_545 no O3 C4 3.3538(14) 4_455 no O4 C5 3.2822(13) 2 no O5 H4 2.64(2) 2_556 no O5 H8 2.742(15) 2 no O5 C1 3.2983(17) 3_666 no O5 C2 3.3493(19) 2_556 no 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 _geom_hbond_publ_flag O1 H7 O2 . 0.87(2) 2.18(2) 2.6552(12) 113.8(16) yes O1 H7 O5 4 0.87(2) 2.48(2) 3.1150(16) 130.2(17) yes O3 H8 O4 2_545 0.882(17) 1.665(17) 2.5361(14) 169.0(17) yes N1 H1 O5 . 0.901(15) 1.825(16) 2.7116(15) 167.3(17) yes N2 H3 O4 1_556 0.920(18) 1.875(19) 2.7662(14) 162.5(19) yes C1 H2 O1 3_666 0.928(18) 2.516(18) 3.3667(18) 152.5(13) yes C2 H4 O2 3_656 0.98(2) 2.49(2) 3.280(2) 137.6(19) yes C2 H4 O3 1_556 0.98(2) 2.524(18) 3.1347(18) 120.2(14) yes C3 H5 O2 . 0.953(17) 2.462(16) 3.3841(19) 162.7(15) yes 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 C4 C5 O2 6.25(12) no O1 C4 C5 O3 -173.06(8) no O1 C4 C6 O4 159.04(9) no O1 C4 C6 O5 -22.06(12) no O2 C5 C4 C6 -115.07(10) no O3 C5 C4 C6 65.62(10) no O4 C6 C4 C5 -79.49(11) no O5 C6 C4 C5 99.40(11) no N1 C1 N2 C2 -0.24(17) no N1 C3 C2 N2 0.0(2) no N2 C1 N1 C3 0.22(17) no C1 N1 C3 C2 -0.1(2) no C1 N2 C2 C3 0.2(2) no