#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/36/2203653.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_2203653 loop_ _publ_author_name 'Li, Dong-Hong' 'Tong, Hong-Bo' 'Huang, Shuping' 'Hao, Junsheng' 'Zhang, Yongbin' 'Xia, Chi-Zhong' _publ_section_title ; 3-(4-Methoxyphenyl)-1,2-dimethyl-4,5-dihydroimidazolium iodide ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o855 _journal_page_last o856 _journal_paper_doi 10.1107/S1600536804009213 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C12 H17 N2 O +, I -' _chemical_formula_moiety 'C12 H17 N2 O +, I -' _chemical_formula_sum 'C12 H17 I N2 O' _chemical_formula_weight 332.18 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 110.014(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.4580(17) _cell_length_b 7.5134(12) _cell_length_c 16.307(3) _cell_measurement_reflns_used 3377 _cell_measurement_temperature 183(2) _cell_measurement_theta_max 26.947 _cell_measurement_theta_min 2.653 _cell_volume 1319.1(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 183(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \w _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 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 5195 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.0 _diffrn_reflns_theta_min 1.90 _diffrn_standards_decay_% 3.99 _exptl_absorpt_coefficient_mu 2.411 _exptl_absorpt_correction_T_max 0.7945 _exptl_absorpt_correction_T_min 0.4456 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description block _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.920 _refine_diff_density_min -0.286 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 2324 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0258 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0347P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.0627 _reflns_number_gt 2083 _reflns_number_total 2324 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6363.cif _cod_data_source_block I _cod_original_cell_volume 1319.0(4) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2203653 _cod_database_fobs_code 2203653 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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_refinement_flags _atom_site_occupancy _atom_site_type_symbol I1 0.824322(19) 0.61571(3) 0.074678(13) 0.04332(10) Uani d . 1 I O1 -0.00046(19) 0.3319(3) 0.39323(14) 0.0441(5) Uani d . 1 O N1 0.3857(2) 0.4250(3) 0.26500(15) 0.0348(6) Uani d . 1 N N2 0.5660(2) 0.5051(3) 0.25886(16) 0.0400(6) Uani d . 1 N C1 0.0256(3) 0.2767(5) 0.4815(2) 0.0489(8) Uani d . 1 C H1A 0.0656 0.1626 0.4903 0.073 Uiso calc R 1 H H1B -0.0506 0.2684 0.4935 0.073 Uiso calc R 1 H H1C 0.0793 0.3621 0.5202 0.073 Uiso calc R 1 H C2 0.0985(3) 0.3491(4) 0.3655(2) 0.0355(7) Uani d . 1 C C3 0.0721(3) 0.4118(4) 0.28075(19) 0.0374(7) Uani d . 1 C H3 -0.0095 0.4375 0.2467 0.045 Uiso calc R 1 H C4 0.1655(3) 0.4359(4) 0.24714(19) 0.0363(7) Uani d . 1 C H4 0.1472 0.4785 0.1906 0.044 Uiso calc R 1 H C5 0.2873(3) 0.3966(4) 0.29774(18) 0.0317(7) Uani d . 1 C C6 0.3133(3) 0.3262(4) 0.38034(18) 0.0329(6) Uani d . 1 C H6 0.3942 0.2938 0.4129 0.039 Uiso calc R 1 H C7 0.2198(3) 0.3038(4) 0.41475(18) 0.0345(7) Uani d . 1 C H7 0.2380 0.2584 0.4708 0.041 Uiso calc R 1 H C8 0.3796(3) 0.3685(4) 0.17596(19) 0.0415(8) Uani d . 1 C H8A 0.3251 0.4449 0.1312 0.050 Uiso calc R 1 H H8B 0.3524 0.2460 0.1642 0.050 Uiso calc R 1 H C9 0.5138(3) 0.3905(4) 0.1828(2) 0.0478(9) Uani d . 1 C H9A 0.5560 0.2765 0.1914 0.057 Uiso calc R 1 H H9B 0.5199 0.4461 0.1307 0.057 Uiso calc R 1 H C10 0.4920(3) 0.5088(4) 0.30454(18) 0.0339(7) Uani d . 1 C C11 0.5237(3) 0.6000(4) 0.39062(19) 0.0388(7) Uani d . 1 C H11A 0.5746 0.5231 0.4357 0.058 Uiso calc R 1 H H11B 0.4487 0.6277 0.4018 0.058 Uiso calc R 1 H H11C 0.5681 0.7079 0.3897 0.058 Uiso calc R 1 H C12 0.6938(3) 0.5683(5) 0.2871(2) 0.0557(10) Uani d . 1 C H12A 0.7011 0.6747 0.3211 0.084 Uiso calc R 1 H H12B 0.7167 0.5935 0.2369 0.084 Uiso calc R 1 H H12C 0.7479 0.4784 0.3219 0.084 Uiso calc R 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 I1 0.04129(15) 0.04097(15) 0.03752(15) 0.00203(9) 0.00036(10) -0.00442(9) O1 0.0335(12) 0.0550(14) 0.0400(12) -0.0021(10) 0.0074(10) 0.0036(11) N1 0.0435(15) 0.0344(14) 0.0234(12) -0.0012(11) 0.0075(11) -0.0007(10) N2 0.0468(15) 0.0378(16) 0.0364(15) 0.0025(13) 0.0157(12) 0.0060(12) C1 0.0423(19) 0.061(2) 0.0432(19) -0.0046(17) 0.0140(15) 0.0035(17) C2 0.0350(17) 0.0265(16) 0.0378(17) -0.0041(13) 0.0034(14) -0.0033(13) C3 0.0356(16) 0.0294(16) 0.0353(17) 0.0005(13) -0.0033(14) 0.0010(13) C4 0.0435(18) 0.0272(16) 0.0283(16) -0.0048(13) -0.0007(14) 0.0012(12) C5 0.0367(16) 0.0250(15) 0.0290(15) -0.0020(12) 0.0056(13) -0.0027(11) C6 0.0333(16) 0.0287(15) 0.0291(15) 0.0012(13) 0.0009(12) -0.0001(13) C7 0.0381(16) 0.0347(17) 0.0252(15) -0.0041(13) 0.0036(13) 0.0008(13) C8 0.067(2) 0.0324(18) 0.0231(15) -0.0006(15) 0.0123(15) -0.0019(12) C9 0.067(2) 0.0367(19) 0.0416(19) 0.0031(16) 0.0207(18) 0.0011(14) C10 0.0407(16) 0.0292(16) 0.0281(15) 0.0015(13) 0.0069(13) 0.0067(12) C11 0.0434(18) 0.0362(18) 0.0314(16) -0.0066(14) 0.0056(14) -0.0007(13) C12 0.045(2) 0.068(3) 0.059(2) -0.0011(18) 0.0230(18) 0.0098(19) 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' I I -0.4742 1.8119 '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 _geom_angle_publ_flag C2 O1 C1 116.8(2) ? C10 N1 C5 127.2(2) ? C10 N1 C8 109.7(3) ? C5 N1 C8 123.0(2) ? C10 N2 C12 126.3(3) ? C10 N2 C9 109.9(3) ? C12 N2 C9 122.4(3) ? O1 C1 H1A 109.5 ? O1 C1 H1B 109.5 ? H1A C1 H1B 109.5 ? O1 C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? O1 C2 C7 124.5(3) ? O1 C2 C3 116.0(3) ? C7 C2 C3 119.5(3) ? C4 C3 C2 120.5(3) ? C4 C3 H3 119.8 ? C2 C3 H3 119.8 ? C3 C4 C5 119.9(3) ? C3 C4 H4 120.1 ? C5 C4 H4 120.1 ? C6 C5 C4 119.8(3) ? C6 C5 N1 119.4(3) ? C4 C5 N1 120.7(3) ? C7 C6 C5 120.4(3) ? C7 C6 H6 119.8 ? C5 C6 H6 119.8 ? C6 C7 C2 119.8(3) ? C6 C7 H7 120.1 ? C2 C7 H7 120.1 ? N1 C8 C9 101.0(3) ? N1 C8 H8A 111.6 ? C9 C8 H8A 111.6 ? N1 C8 H8B 111.6 ? C9 C8 H8B 111.6 ? H8A C8 H8B 109.4 ? N2 C9 C8 103.7(3) ? N2 C9 H9A 111.0 ? C8 C9 H9A 111.0 ? N2 C9 H9B 111.0 ? C8 C9 H9B 111.0 ? H9A C9 H9B 109.0 ? N2 C10 N1 112.3(3) yes N2 C10 C11 123.4(3) ? N1 C10 C11 124.3(3) ? C10 C11 H11A 109.5 ? C10 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C10 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? N2 C12 H12A 109.5 ? N2 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? N2 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.363(4) ? O1 C1 1.428(4) ? N1 C10 1.326(4) yes N1 C5 1.419(4) yes N1 C8 1.491(4) yes N2 C10 1.306(4) yes N2 C12 1.456(4) yes N2 C9 1.460(4) yes C1 H1A 0.9600 ? C1 H1B 0.9600 ? C1 H1C 0.9600 ? C2 C7 1.389(4) ? C2 C3 1.392(4) ? C3 C4 1.371(4) ? C3 H3 0.9300 ? C4 C5 1.389(4) ? C4 H4 0.9300 ? C5 C6 1.382(4) ? C6 C7 1.378(4) ? C6 H6 0.9300 ? C7 H7 0.9300 ? C8 C9 1.512(5) ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? C9 H9A 0.9700 ? C9 H9B 0.9700 ? C10 C11 1.491(4) ? C11 H11A 0.9600 ? C11 H11B 0.9600 ? C11 H11C 0.9600 ? C12 H12A 0.9600 ? C12 H12B 0.9600 ? C12 H12C 0.9600 ? 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 C1 O1 C2 C7 5.2(4) yes C1 O1 C2 C3 -176.8(3) ? O1 C2 C3 C4 179.2(3) ? C7 C2 C3 C4 -2.7(4) ? C2 C3 C4 C5 0.4(4) ? C3 C4 C5 C6 2.8(4) ? C3 C4 C5 N1 -178.3(3) ? C10 N1 C5 C6 -50.2(4) yes C8 N1 C5 C6 132.7(3) ? C10 N1 C5 C4 130.9(3) ? C8 N1 C5 C4 -46.2(4) yes C4 C5 C6 C7 -3.6(4) ? N1 C5 C6 C7 177.5(3) ? C5 C6 C7 C2 1.2(4) ? O1 C2 C7 C6 179.9(3) ? C3 C2 C7 C6 1.9(4) ? C10 N1 C8 C9 14.8(3) ? C5 N1 C8 C9 -167.6(3) ? C10 N2 C9 C8 15.9(3) ? C12 N2 C9 C8 -176.9(3) ? N1 C8 C9 N2 -17.5(3) ? C12 N2 C10 N1 -173.4(3) ? C9 N2 C10 N1 -6.8(3) ? C12 N2 C10 C11 7.6(5) ? C9 N2 C10 C11 174.2(3) ? C5 N1 C10 N2 176.9(3) ? C8 N1 C10 N2 -5.7(3) ? C5 N1 C10 C11 -4.1(5) ? C8 N1 C10 C11 173.3(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21130846 2 PubChem 139066683