#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/35/2003500.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_2003500 loop_ _publ_author_name 'Aubry, A.' 'Brembilla, A.' 'Faivre, V.' 'Lochon, P.' _publ_section_title ; 5-Dodecyl-2-(1-hydroxyethyl)benzimidazolium Chloride ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 893 _journal_page_last 894 _journal_paper_doi 10.1107/S0108270194011273 _journal_volume 51 _journal_year 1995 _chemical_compound_source 'from ethanol/nitromethane (20/80 v/v)' _chemical_formula_moiety 'C21 H35 Cl N2 O1' _chemical_formula_sum 'C21 H35 Cl N2 O' _chemical_formula_weight 366.97 _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _atom_type_scat_source IntTabIV _cell_angle_alpha 90 _cell_angle_beta 86.96(1) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.174(1) _cell_length_b 7.228(1) _cell_length_c 36.114(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 30 _cell_measurement_theta_min 20 _cell_volume 2130.7(4) _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-2\q _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3925 _diffrn_reflns_theta_max 70 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 1.563 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.144 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.22 _refine_diff_density_min -0.22 _refine_ls_goodness_of_fit_obs 1.725 _refine_ls_hydrogen_treatment refxyz _refine_ls_number_parameters 228 _refine_ls_number_reflns 1981 _refine_ls_R_factor_obs 0.0463 _refine_ls_shift/esd_max 0.05 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1.645/[\s^2^(F) + 0.0014F^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.0541 _reflns_number_observed 1981 _reflns_number_total 2042 _reflns_observed_criterion >\s(I) _cod_data_source_file pa1122.cif _cod_data_source_block pa1122a _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'w = 1.645/[\s^2^(F) + 0.0014F^2^]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1.645/[\s^2^(F) + 0.0014F^2^]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2131 _cod_original_sg_symbol_H-M 'C c' _cod_original_formula_sum 'C21 H35 Cl N2 O1' _cod_database_code 2003500 loop_ _symmetry_equiv_pos_as_xyz x,y,z x,-y,1/2+z 1/2+x,1/2+y,z 1/2+x,1/2-y,1/2+z loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv Cl .3794 .291 .3211 6.09(3) O(1) -.0046(4) .4789(5) .2688(1) 5.75(7) C(2) -.1342(4) .3599(5) .2777(1) 4.11(7) C(1) -.1220(7) .1946(7) .2524(1) 5.7(1) C(3) -.1297(4) .2992(4) .3177(1) 3.35(6) N(1) -.2615(4) .2610(4) .33960(8) 3.44(5) C(4) -.2095(4) .1951(4) .37343(9) 3.15(6) C(5) -.0389(4) .1995(4) .37054(9) 3.28(6) N(2) .0050(4) .2663(4) .33539(8) 3.48(5) C(6) .0511(4) .1377(5) .3995(1) 3.77(6) C(7) -.0358(4) .0697(5) .43021(9) 3.75(6) C(8) -.2093(4) .0651(4) .43320(9) 3.34(6) C(9) -.2970(4) .1300(4) .40424(9) 3.27(6) C(10) -.2929(4) -.0182(5) .4679(1) 4.02(7) C(11) -.4716(4) .0220(5) .4752(1) 3.90(7) C(12) -.5418(4) -.0697(5) .5105(1) 3.94(7) C(13) -.7222(5) -.0309(6) .5191(1) 4.19(7) C(14) -.7927(4) -.1267(6) .5538(1) 4.01(7) C(15) -.9724(4) -.0827(5) .5629(1) 4.21(7) C(16) -1.0433(5) -.1813(6) .5971(1) 4.11(7) C(17) -1.2224(5) -.1370(6) .6067(1) 4.34(7) C(18) -1.2919(5) -.2365(6) .6410(1) 4.36(7) C(19) -1.4695(5) -.1901(6) .6513(1) 4.64(8) C(20) -1.5382(6) -.2896(7) .6855(1) 5.3(1) C(21) -1.7161(7) -.2448(8) .6955(2) 6.3(1) H001 -.020(6) .581(6) .289(1) . H21 -.2490(4) .4302(5) .2743(1) . H11 -.2223(7) .1012(7) .2591(1) . H12 -.0073(7) .1242(7) .2558(1) . H13 -.1277(7) .2400(7) .2240(1) . H01 -.3873(4) .2780(4) .33249(8) . H02 .1290(4) .2888(4) .32444(8) . H61 .1833(4) .1424(5) .3979(1) . H71 .0313(4) .0178(5) .45298(9) . H91 -.4293(4) .1297(4) .40571(9) . H101 -.2297(4) .0325(5) .4913(1) . H102 -.2790(4) -.1665(5) .4659(1) . H111 -.4880(4) .1698(5) .4776(1) . H112 -.5373(4) -.0287(5) .4521(1) . H121 -.4745(4) -.0199(5) .5335(1) . H122 -.5257(4) -.2175(5) .5078(1) . H131 -.7381(5) .1166(6) .5225(1) . H132 -.7893(5) -.0772(6) .4958(1) . H141 -.7232(4) -.0837(6) .5769(1) . H142 -.7803(4) -.2744(6) .5500(1) . H151 -1.0416(4) -.1225(5) .5395(1) . H152 -.9845(4) .0645(5) .5674(1) . H161 -1.0329(5) -.3285(6) .5924(1) . H162 -.9726(5) -.1432(6) .6204(1) . H171 -1.2935(5) -.1760(6) .5836(1) . H172 -1.2333(5) .0103(6) .6113(1) . H181 -1.2827(5) -.3836(6) .6361(1) . H182 -1.2191(5) -.1993(6) .6639(1) . H191 -1.5422(5) -.2268(6) .6283(1) . H192 -1.4786(6) -.0431(6) .6562(1) . H201 -1.5282(6) -.4366(7) .6806(1) . H202 -1.4660(6) -.2521(7) .7085(1) . H211 -1.7560(7) -.3211(8) .7201(2) . H212 -1.7905(7) -.2829(8) .6729(2) . H213 -1.7284(7) -.0983(8) .7008(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 O(1) C(2) C(1) 109.0(3) yes O(1) C(2) C(3) 110.1(3) yes C(1) C(2) C(3) 110.3(3) yes C(2) C(3) N(1) 124.6(3) yes C(2) C(3) N(2) 125.2(3) yes N(1) C(3) N(2) 110.1(3) yes C(3) N(1) C(4) 108.4(3) yes N(1) C(4) C(5) 106.0(3) yes N(1) C(4) C(9) 130.9(3) yes C(5) C(4) C(9) 123.0(3) yes C(4) C(5) N(2) 106.6(3) yes C(4) C(5) C(6) 120.4(3) yes N(2) C(5) C(6) 132.9(3) yes C(3) N(2) C(5) 108.8(3) yes C(5) C(6) C(7) 116.9(3) yes C(6) C(7) C(8) 122.8(3) yes C(7) C(8) C(9) 119.5(3) yes C(7) C(8) C(10) 118.5(3) yes C(9) C(8) C(10) 122.0(3) yes C(4) C(9) C(8) 117.4(3) yes C(8) C(10) C(11) 117.4(3) yes C(10) C(11) C(12) 112.6(3) yes C(11) C(12) C(13) 114.2(3) yes C(12) C(13) C(14) 113.9(3) yes C(13) C(14) C(15) 113.7(3) yes C(14) C(15) C(16) 113.6(3) yes C(15) C(16) C(17) 114.1(3) yes C(16) C(17) C(18) 113.6(3) yes C(17) C(18) C(19) 114.1(3) yes C(18) C(19) C(20) 113.9(4) yes C(19) C(20) C(21) 113.9(4) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O(1) C(2) 1.389(5) yes C(2) C(1) 1.506(6) yes C(2) C(3) 1.511(5) yes C(3) N(1) 1.331(4) yes C(3) N(2) 1.324(5) yes N(1) C(4) 1.398(4) yes C(4) C(5) 1.394(4) yes C(4) C(9) 1.374(4) yes C(5) N(2) 1.387(4) yes C(5) C(6) 1.383(5) yes C(6) C(7) 1.377(5) yes C(7) C(8) 1.417(5) yes C(8) C(9) 1.381(5) yes C(8) C(10) 1.518(5) yes C(10) C(11) 1.499(5) yes C(11) C(12) 1.523(5) yes C(12) C(13) 1.517(5) yes C(13) C(14) 1.518(5) yes C(14) C(15) 1.522(5) yes C(15) C(16) 1.516(5) yes C(16) C(17) 1.520(5) yes C(17) C(18) 1.516(6) yes C(18) C(19) 1.517(6) yes C(19) C(20) 1.511(6) yes C(20) C(21) 1.515(7) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139054301