#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/48/2004807.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_2004807 loop_ _publ_author_name 'Jones, R. H.' 'Lothian, A. P.' 'Ramsden, C. A.' _publ_section_title ; 5-Amino-1,2-dimethylimidazole ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 982 _journal_page_last 984 _journal_paper_doi 10.1107/S0108270195011711 _journal_volume 52 _journal_year 1996 _chemical_formula_analytical 'C5 H9 N3' _chemical_formula_moiety 'C5 H9 N3' _chemical_formula_structural 'C5 H9 N3' _chemical_formula_sum 'C5 H9 N3' _chemical_formula_weight 111.15 _chemical_melting_point '120-140 softening' _chemical_name_common 5-Amino-1,2-dimethylimidazole _chemical_name_systematic 5-Amino-1,2-dimethylimidazole _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 5.892(3) _cell_length_b 8.480(3) _cell_length_c 11.509(9) _cell_measurement_reflns_used 206 _cell_measurement_temperature 120 _cell_measurement_theta_max 20 _cell_measurement_theta_min 2 _cell_volume 575.0(6) _computing_cell_refinement MADNESS _computing_data_collection 'MADNESS (Pflugrath & Messerschmidt, 1990)' _computing_data_reduction MADNESS _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXS93 _computing_structure_refinement 'SHELXS93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 120 _diffrn_measurement_device 'Enraf-Nonius FAST TV area detector' _diffrn_measurement_method 'Data collection: MADNESS (Pflugrath & Messerschmidt, 1990)' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.1539 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2527 _diffrn_reflns_theta_max 24.95 _diffrn_reflns_theta_min 2.98 _diffrn_standards_decay_% ' See exptl special details' _diffrn_standards_interval_count ' See exptl special details' _diffrn_standards_interval_time ' See exptl special details' _diffrn_standards_number no _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.284 _exptl_crystal_description plates _exptl_crystal_F_000 240 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.156 _refine_diff_density_min -0.165 _refine_ls_abs_structure_details 'Flack parameter (Flack, 1983) = 1.56(559)' _refine_ls_abs_structure_Flack 2.(6) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.623 _refine_ls_goodness_of_fit_obs 0.708 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 104 _refine_ls_number_reflns 904 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.623 _refine_ls_restrained_S_obs 0.708 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_obs 0.0365 _refine_ls_shift/esd_max 0.139 _refine_ls_shift/esd_mean 0.028 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.0159P)^2^] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.0723 _refine_ls_wR_factor_obs 0.0569 _reflns_number_observed 484 _reflns_number_total 904 _reflns_observed_criterion >2sigma(I) _cod_data_source_file pa1207.cif _cod_data_source_block s072 _cod_database_code 2004807 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 N1 0.025(2) 0.025(2) 0.022(2) 0.002(2) 0.0024(15) 0.0016(14) C2 0.030(2) 0.022(2) 0.020(2) -0.004(2) -0.003(2) -0.002(2) N3 0.028(2) 0.028(2) 0.022(2) 0.0012(14) 0.0031(15) -0.0024(15) C4 0.030(2) 0.027(2) 0.024(2) 0.005(2) 0.003(2) -0.005(2) C5 0.025(2) 0.017(2) 0.028(2) 0.000(2) -0.001(2) -0.001(2) N6 0.038(2) 0.023(2) 0.028(2) 0.0037(15) -0.001(2) -0.002(2) C7 0.036(2) 0.026(2) 0.027(3) 0.010(2) -0.003(2) -0.007(2) C8 0.033(2) 0.043(3) 0.029(2) 0.006(2) 0.009(2) 0.002(2) loop_ _atom_site_label _atom_site_occupancy _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_type_symbol N1 1 0.0189(4) 0.4987(3) 1.0352(2) 0.0240(7) Uani d N C2 1 0.0005(6) 0.5661(4) 0.9274(3) 0.0239(8) Uani d C N3 1 0.1620(4) 0.5155(3) 0.8570(3) 0.0261(7) Uani d N C4 1 0.2933(6) 0.4120(4) 0.9238(3) 0.0270(9) Uani d C C5 1 0.2094(5) 0.4017(4) 1.0334(3) 0.0230(8) Uani d C N6 1 0.2700(5) 0.3119(3) 1.1306(3) 0.0298(8) Uani d N C7 1 -0.1765(7) 0.6848(4) 0.8987(3) 0.0298(10) Uani d C C8 1 -0.1284(7) 0.5249(5) 1.1357(4) 0.0353(11) Uani d C H4 1 0.4131(53) 0.3673(36) 0.8855(32) 0.037(11) Uiso d H H6A 1 0.3645(67) 0.2283(48) 1.1178(33) 0.070(10) Uiso d H H6B 1 0.2803(55) 0.3768(45) 1.2017(39) 0.070(10) Uiso d H H7A 1 -0.1405(50) 0.7270(39) 0.8117(30) 0.044(6) Uiso d H H7B 1 -0.3422(52) 0.6491(39) 0.8977(27) 0.044(6) Uiso d H H7C 1 -0.1666(47) 0.7790(40) 0.9491(33) 0.044(6) Uiso d H H8A 1 -0.2795(60) 0.5101(49) 1.1065(36) 0.074(9) Uiso d H H8B 1 -0.0812(60) 0.4599(48) 1.2055(37) 0.074(9) Uiso d H H8C 1 -0.1478(69) 0.6164(52) 1.1417(41) 0.074(9) Uiso d H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.0016 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.0000 N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.0033 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 C2 N1 C5 107.3(3) yes C2 N1 C8 127.3(3) yes C5 N1 C8 125.4(3) yes N3 C2 N1 111.2(3) yes N3 C2 C7 126.1(3) yes N1 C2 C7 122.7(3) yes C2 N3 C4 105.4(3) yes C5 C4 N3 110.4(3) yes C4 C5 N1 105.6(3) yes C4 C5 N6 133.2(3) yes N1 C5 N6 121.0(3) yes C5 N6 H6A 117.(3) ? C5 N6 H6B 112.(2) ? C5 C4 H4 135.(2) ? N3 C4 H4 115.(2) ? H6A N6 H6B 122.(3) ? C2 C7 H7A 107.0(18) ? C2 C7 H7B 118.(2) ? H7A C7 H7B 106.(3) ? C2 C7 H7C 112.0(19) ? H7A C7 H7C 105.(3) ? H7B C7 H7C 108.(2) ? N1 C8 H8A 105.(3) ? N1 C8 H8B 112.(2) ? H8A C8 H8B 118.(3) ? N1 C8 H8C 108.(3) ? H8A C8 H8C 91.(4) ? H8B C8 H8C 120.(4) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.370(4) yes N1 C5 1.391(3) yes N1 C8 1.463(5) yes C2 N3 1.321(4) yes C2 C7 1.486(5) yes N3 C4 1.400(4) yes C4 C5 1.358(5) yes C5 N6 1.400(4) yes N6 H6A 0.91(4) ? N6 H6B 0.99(4) ? C4 H4 0.91(3) ? C7 H7A 1.08(3) ? C7 H7B 1.02(3) ? C7 H7C 0.99(4) ? C8 H8A 0.96(4) ? C8 H8B 1.01(4) ? C8 H8C 0.79(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 117821 2 PubChem 133566