#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/02/2010271.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_2010271 loop_ _publ_author_name 'Meyers, Cal Y.' 'Lutfi, Hisham G.' 'Kolb, Vera M.' 'Robinson, Paul D.' _publ_section_title ; Racemic 1-methyl-1,2,4-triazolidine-3,5-dione (1-methylurazole). Definitive characterization of pyramidal hydrazide N atoms and racemate intermolecular hydrogen bonding ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1925 _journal_page_last 1928 _journal_volume 50 _journal_year 1994 _chemical_formula_moiety 'C3 H5 N3 O2' _chemical_formula_sum 'C3 H5 N3 O2' _chemical_formula_weight 115.09 _chemical_name_common 1-methylurazole _chemical_name_systematic ; 1-methyl-1,2,4-triazolidine-3,5-dione ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 19.132(2) _cell_length_b 6.7170(10) _cell_length_c 3.891(2) _cell_measurement_reflns_used 24 _cell_measurement_temperature 296 _cell_measurement_theta_max 21.8 _cell_measurement_theta_min 19.0 _cell_volume 500.0(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction ; TEXSAN PROCESS (Molecular Structure Corporation, 1985) ; _computing_molecular_graphics 'ORTEP (Johnson, 1965) TEXSAN' _computing_publication_material 'FINISH TEXSAN' _computing_structure_refinement 'LS TEXSAN' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 296 _diffrn_measurement_device 'Rigaku AFC5S diffractometer' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source x-ray_tube _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 997 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 1.75 _diffrn_standards_decay_% -2.7 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.528 _exptl_crystal_description tabular _exptl_crystal_F_000 240 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.11 _refine_diff_density_min -0.10 _refine_ls_abs_structure_details ; The absolute configuration of the structure was not determined. ; _refine_ls_extinction_coef 0.8E-5(1) _refine_ls_extinction_method 'Zachariasen (1963) type 2 Gaussian isotropic' _refine_ls_goodness_of_fit_obs 1.47 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 81 _refine_ls_number_reflns 448 _refine_ls_R_factor_obs 0.026 _refine_ls_shift/esd_max 0.0002 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = 4F~o~^2^/\s^2^(F~o~^2^)' _refine_ls_wR_factor_obs 0.032 _reflns_number_observed 448 _reflns_number_total 513 _reflns_observed_criterion '[I > 3.0\s(I)]' _[local]_cod_data_source_file cr1122.cif _[local]_cod_data_source_block default _cod_original_cell_volume 500.1(3) _cod_database_code 2010271 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,1/2+z 1/2-x,1/2+y,1/2+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_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O7 0.06337(7) 0.3279(2) 0.2987 0.0460(10) Uani ? ? O8 0.24426(8) 0.6602(3) 0.8160(10) 0.0530(10) Uani ? ? N1 0.12581(8) 0.7240(3) 0.7610(10) 0.0380(10) Uani ? ? N2 0.07210(10) 0.6327(3) 0.5730(10) 0.0340(10) Uani ? ? N4 0.16633(9) 0.4531(3) 0.5300(10) 0.0370(10) Uani ? ? C3 0.09660(10) 0.4564(3) 0.4520(10) 0.0330(10) Uani ? ? C5 0.18530(10) 0.6195(3) 0.7130(10) 0.0360(10) Uani ? ? C6 0.11990(10) 0.9296(4) 0.8640(10) 0.0500(10) Uani ? ? H2 0.0300(10) 0.652(3) 0.663(7) 0.052(9) Uiso ? ? H4 0.197(2) 0.359(3) 0.450(10) 0.056(8) Uiso ? ? H6a 0.0800 0.9455 1.0068 0.059 Uiso calc C6 H6b 0.1151 1.0109 0.6655 0.059 Uiso calc C6 H6c 0.1606 0.9677 0.9867 0.059 Uiso calc C6 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 O7 0.0288(7) 0.0410(10) 0.0680(10) 0.0011(7) -0.0130(10) -0.0130(10) O8 0.0287(8) 0.0470(10) 0.083(2) -0.0057(7) -0.0070(10) -0.0170(10) N1 0.0290(10) 0.0310(10) 0.0550(10) 0.0001(7) 0.0050(10) -0.0080(10) N2 0.0211(9) 0.0330(10) 0.0490(10) 0.0028(8) 0.0030(10) -0.0040(10) N4 0.0210(10) 0.0340(10) 0.055(2) 0.0028(7) -0.0001(9) -0.0070(10) C3 0.0220(10) 0.0330(10) 0.0440(10) 0.0010(10) -0.0010(10) 0.0000(10) C5 0.0300(10) 0.0340(10) 0.045(2) -0.0020(10) 0.0000(10) -0.0050(10) C6 0.060(2) 0.0340(10) 0.055(2) 0.0030(10) 0.0020(10) -0.0080(10) 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 O7 C3 . . 1.227(3) yes O8 C5 . . 1.227(3) yes N1 N2 . . 1.403(3) yes N1 C5 . . 1.350(3) yes N1 C6 . . 1.442(3) yes N2 C3 . . 1.357(3) yes N4 C3 . . 1.369(3) yes N4 C5 . . 1.375(3) yes N2 H2 . . 0.88(3) yes H2 O7 . 2_565 1.87(3) yes N2 O7 . 2_565 2.751(3) yes N4 H4 . . 0.91(3) yes H4 O8 . 3_544 1.83(3) yes N4 O8 . 3_544 2.737(3) yes C6 H6a . . 0.950 no C6 H6b . . 0.950 no C6 H6c . . 0.950 no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .002 .002 International_Tables_Vol_IV_Table_2.3.1 H 0 0 International_Tables_Vol_IV_Table_2.3.1 O .008 .006 International_Tables_Vol_IV_Table_2.3.1 N .004 .003 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -1 0 1 1 0 1 3 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N2 N1 C5 . 108.5(2) yes N2 N1 C6 . 120.4(2) yes C5 N1 C6 . 127.1(2) yes N1 N2 C3 . 108.1(2) yes N1 N2 H2 . 113(2) yes C3 N2 H2 . 125(2) yes C3 N4 C5 . 111.1(2) yes C3 N4 H4 . 124(2) yes C5 N4 H4 . 125(2) yes O7 C3 N2 . 127.2(2) yes O7 C3 N4 . 126.9(2) yes N2 C3 N4 . 105.8(2) yes O8 C5 N1 . 127.9(2) yes O8 C5 N4 . 126.4(2) yes N1 C5 N4 . 105.8(2) yes N2 H2 O7 2_565 171(2) yes N4 H4 O8 3_544 177(3) yes N1 C6 H6a . 109.46 no N1 C6 H6b . 109.46 no N1 C6 H6c . 109.46 no H6a C6 H6b . 109.49 no H6a C6 H6c . 109.48 no H6b C6 H6c . 109.48 no 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 O7 C3 N2 N1 174.0(3) O7 C3 N2 H2 37(2) O7 C3 N4 C5 -178.1(3) O7 C3 N4 H4 7(3) O8 C5 N1 N2 174.5(3) O8 C5 N1 C6 17.4(5) O8 C5 N4 C3 -179.0(3) O8 C5 N4 H4 -4(3) N1 N2 C3 N4 -7.3(3) N1 C5 N4 C3 2.3(3) N1 C5 N4 H4 177(3) N2 N1 C5 N4 -6.8(3) N2 C3 N4 C5 3.2(3) N2 C3 N4 H4 -172(3) N4 C3 N2 H2 -144(2) N4 C5 N1 C6 -163.8(3) C3 N2 N1 C5 9.0(3) C3 N2 N1 C6 167.9(2) C5 N1 N2 H2 152(2) C6 N1 N2 H2 -49(2)