#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010306.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_2010306 loop_ _publ_author_name 'Xu, Shimin' 'Gantzel, Peter K.' 'Clark, Leigh B.' _publ_section_title ; Glycoluril ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1988 _journal_page_last 1989 _journal_paper_doi 10.1107/S0108270194006955 _journal_volume 50 _journal_year 1994 _chemical_formula_sum 'C4 H6 N4 O2' _chemical_formula_weight 142.12 _chemical_name_common glycoluril _chemical_name_systematic ; tetrahydroimidazo [4,5-d] imidazole-2,5 (1H, 3H)-dione ; _space_group_IT_number 63 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-C 2c 2' _symmetry_space_group_name_H-M 'C m c m' _audit_creation_method SHELXL _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 7.373(2) _cell_length_b 7.546(3) _cell_length_c 10.579(3) _cell_measurement_reflns_used 16 _cell_measurement_temperature 299 _cell_measurement_theta_max 13.5 _cell_measurement_theta_min 4 _cell_volume 588.6(3) _computing_cell_refinement SHELXTL-Plus _computing_data_collection 'SHELXTL-Plus (Sheldrick, year?)' _computing_data_reduction SHELXTL-Plus _computing_molecular_graphics SHELXTL-Plus _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1994)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _diffrn_ambient_temperature 299 _diffrn_measurement_device 'Siemens R3m/V diffractometer' _diffrn_measurement_method Wyckoff _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 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 550 _diffrn_reflns_theta_max 29.94 _diffrn_reflns_theta_min 3.85 _diffrn_standards_decay_% 0.35 _diffrn_standards_interval_count 197 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.604 _exptl_crystal_description prism _exptl_crystal_F_000 296 _exptl_crystal_size_max 1.0 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _refine_diff_density_max 0.268 _refine_diff_density_min -0.264 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.081 _refine_ls_goodness_of_fit_obs 1.114 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 31 _refine_ls_number_reflns 486 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_restrained_S_obs 1.114 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_obs 0.0405 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^)+(0.0785P)^2^+0.1473P] where P = (F~o~^2^+2Fc^2^)/3 ; _refine_ls_wR_factor_all 0.1246 _refine_ls_wR_factor_obs 0.1163 _reflns_number_observed 403 _reflns_number_total 486 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ka1088.cif _cod_data_source_block glyc _cod_database_code 2010306 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,z+1/2 -x,y,-z+1/2 x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,-z -x,-y,-z x,y,-z-1/2 x,-y,z-1/2 -x,y,z -x+1/2,-y+1/2,-z x+1/2,y+1/2,-z-1/2 x+1/2,-y+1/2,z-1/2 -x+1/2,y+1/2,z 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 0.0250(6) 0.0651(8) 0.0277(6) 0.000 0.000 -0.0136(5) N2 0.0189(5) 0.0625(7) 0.0260(5) -0.0012(4) 0.0007(3) -0.0096(4) C3 0.0227(6) 0.0374(7) 0.0221(6) -0.0028(5) 0.000 0.000 C4 0.0213(6) 0.0414(8) 0.0226(7) 0.000 0.000 -0.0002(6) 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 O1 0.0000 0.2245(2) 0.46658(11) 0.0393(4) Uani d S 1 . O N2 0.14924(12) 0.3510(2) 0.63534(9) 0.0358(3) Uani d . 1 . N H2A 0.26281(12) 0.3271(2) 0.60926(9) 0.046(4) Uiso d R 1 . H C3 0.1059(2) 0.4450(2) 0.7500 0.0274(4) Uani d S 1 . C H3A 0.1551(2) 0.5628(2) 0.7500 0.031(5) Uiso d SR 1 . H C4 0.0000 0.3016(2) 0.57014(15) 0.0285(4) Uani d S 1 . C 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 N2 C3 . . 112.64(11) yes N2 C3 N2 10_557 . 114.67(13) yes N2 C3 C3 10_557 3_556 102.82(7) yes N2 C3 C3 . 3_556 102.82(7) ? O1 C4 N2 . . 125.47(7) yes O1 C4 N2 . 12 125.47(7) ? N2 C4 N2 . 12 109.05(14) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C4 . 1.241(2) yes N2 C4 . 1.3512(13) yes N2 C3 . 1.4409(13) yes C3 N2 10_557 1.4409(13) ? C3 C3 3_556 1.561(3) yes C4 N2 12 1.3512(13) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 62347