#------------------------------------------------------------------------------ #$Date: 2008-02-04 17:24:24 +0000 (Mon, 04 Feb 2008) $ #$Revision: 87 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204184.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_2204184 loop_ _publ_author_name 'Tong, Yi-Ping' 'Li, Wei' _publ_section_title ; 2-(2-Ethoxyphenyl)-1-ethyl-1H-benzimidazole ; _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1563 _journal_page_last o1565 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C17 H18 N2 O' _chemical_formula_moiety 'C17 H18 N2 O' _chemical_formula_sum 'C17 H18 N2 O' _chemical_formula_weight 266.33 _chemical_name_systematic ; 2-(2-Ethoxyphenyl)-1-ethyl-1H-benzimidazole ; _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.3305(8) _cell_length_b 12.4070(10) _cell_length_c 12.7422(10) _cell_measurement_reflns_used 1432 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.75 _cell_measurement_theta_min 2.29 _cell_volume 1475.1(2) _computing_cell_refinement 'SAINT (Bruker, 2001)' _computing_data_collection 'SMART (Bruker, 2001)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 2000)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_device_type 'Bruker APEX area-detector' _diffrn_measurement_method '\f and \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 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9232 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.29 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_correction_T_min 0.9759 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.149 _refine_diff_density_min -0.156 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 1922 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0499 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0455P)^2^+0.2012P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1031 _refine_ls_wR_factor_ref 0.1097 _reflns_number_gt 1582 _reflns_number_total 1922 _reflns_threshold_expression I>2\s(I) _[local]_cod_original_file hg6076.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N1 0.0603(2) 0.23129(16) 0.73990(17) 0.0405(5) Uani d . 1 N N2 0.0707(2) 0.38970(16) 0.65627(17) 0.0416(5) Uani d . 1 N O1 0.1413(2) 0.38910(18) 0.92994(16) 0.0588(6) Uani d . 1 O C1 0.2718(3) 0.3787(2) 0.8844(2) 0.0438(6) Uani d . 1 C C2 0.4010(3) 0.3977(2) 0.9339(2) 0.0553(8) Uani d . 1 C H2 0.4026 0.4211 1.0033 0.066 Uiso calc R 1 H C3 0.5273(3) 0.3819(3) 0.8804(3) 0.0601(8) Uani d . 1 C H3 0.6138 0.3934 0.9148 0.072 Uiso calc R 1 H C4 0.5283(3) 0.3494(3) 0.7773(3) 0.0591(8) Uani d . 1 C H4 0.6144 0.3387 0.7421 0.071 Uiso calc R 1 H C5 0.3992(3) 0.3330(2) 0.7272(2) 0.0516(7) Uani d . 1 C H5 0.3989 0.3122 0.6571 0.062 Uiso calc R 1 H C6 0.2702(3) 0.34703(19) 0.7789(2) 0.0407(6) Uani d . 1 C C7 0.1327(3) 0.32553(19) 0.7244(2) 0.0384(6) Uani d . 1 C C8 -0.0501(3) 0.33360(19) 0.6239(2) 0.0387(6) Uani d . 1 C C9 -0.1559(3) 0.3607(2) 0.5509(2) 0.0490(7) Uani d . 1 C H9 -0.1531 0.4262 0.5154 0.059 Uiso calc R 1 H C10 -0.2638(3) 0.2882(2) 0.5331(2) 0.0540(7) Uani d . 1 C H10 -0.3351 0.3053 0.4849 0.065 Uiso calc R 1 H C11 -0.2700(3) 0.1899(2) 0.5848(2) 0.0546(8) Uani d . 1 C H11 -0.3449 0.1428 0.5704 0.065 Uiso calc R 1 H C12 -0.1673(3) 0.1608(2) 0.6572(2) 0.0496(7) Uani d . 1 C H12 -0.1707 0.0950 0.6920 0.060 Uiso calc R 1 H C13 -0.0588(3) 0.2347(2) 0.6755(2) 0.0389(6) Uani d . 1 C C14 0.1089(3) 0.1365(2) 0.7984(2) 0.0475(7) Uani d . 1 C H14A 0.0265 0.1000 0.8283 0.057 Uiso calc R 1 H H14B 0.1701 0.1595 0.8557 0.057 Uiso calc R 1 H C15 0.1897(3) 0.0594(2) 0.7299(3) 0.0628(9) Uani d . 1 C H15A 0.1290 0.0357 0.6737 0.094 Uiso calc R 1 H H15B 0.2194 -0.0017 0.7708 0.094 Uiso calc R 1 H H15C 0.2725 0.0948 0.7015 0.094 Uiso calc R 1 H C16 0.1347(4) 0.4143(3) 1.0394(3) 0.0681(10) Uani d . 1 C H16A 0.1812 0.4828 1.0528 0.082 Uiso calc R 1 H H16B 0.1832 0.3591 1.0799 0.082 Uiso calc R 1 H C17 -0.0188(4) 0.4199(3) 1.0697(3) 0.0912(13) Uani d . 1 C H17A -0.0642 0.4781 1.0329 0.137 Uiso calc R 1 H H17B -0.0262 0.4319 1.1440 0.137 Uiso calc R 1 H H17C -0.0652 0.3533 1.0519 0.137 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 N1 0.0422(12) 0.0382(10) 0.0412(12) -0.0025(10) -0.0033(10) 0.0026(10) N2 0.0468(13) 0.0352(10) 0.0427(12) 0.0014(10) 0.0000(10) 0.0009(10) O1 0.0508(12) 0.0767(14) 0.0490(12) -0.0036(11) 0.0069(10) -0.0170(11) C1 0.0463(15) 0.0409(13) 0.0441(15) 0.0007(13) 0.0001(13) -0.0035(12) C2 0.0549(18) 0.0635(18) 0.0477(17) -0.0070(15) -0.0083(15) -0.0098(15) C3 0.0483(18) 0.0622(18) 0.070(2) -0.0094(16) -0.0091(15) -0.0074(18) C4 0.0403(16) 0.066(2) 0.071(2) -0.0074(15) 0.0078(15) -0.0131(18) C5 0.0506(17) 0.0550(16) 0.0492(16) -0.0070(14) 0.0033(14) -0.0077(14) C6 0.0427(14) 0.0346(12) 0.0448(15) -0.0035(11) -0.0010(12) 0.0014(12) C7 0.0435(15) 0.0339(12) 0.0377(14) 0.0001(11) 0.0045(12) -0.0055(11) C8 0.0429(15) 0.0366(12) 0.0367(13) 0.0039(12) 0.0013(11) -0.0055(11) C9 0.0561(17) 0.0463(15) 0.0445(17) 0.0068(14) -0.0057(13) 0.0000(13) C10 0.0515(17) 0.0631(18) 0.0474(17) 0.0079(16) -0.0120(15) -0.0090(15) C11 0.0479(17) 0.0567(17) 0.0591(19) -0.0087(14) -0.0086(15) -0.0116(15) C12 0.0521(16) 0.0409(14) 0.0558(18) -0.0044(13) -0.0037(14) 0.0017(14) C13 0.0385(14) 0.0408(13) 0.0372(14) 0.0029(12) 0.0021(12) -0.0037(11) C14 0.0531(16) 0.0453(14) 0.0440(15) -0.0072(13) -0.0025(13) 0.0117(13) C15 0.067(2) 0.0511(17) 0.070(2) 0.0127(15) 0.0059(17) 0.0127(17) C16 0.079(2) 0.072(2) 0.053(2) -0.0078(18) 0.0163(18) -0.0139(17) C17 0.094(3) 0.095(3) 0.085(3) 0.001(2) 0.041(2) -0.015(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C7 1.365(3) yes N1 C13 1.382(3) yes N1 C14 1.464(3) yes N2 C7 1.312(3) yes N2 C8 1.387(3) yes O1 C1 1.355(3) yes O1 C16 1.431(4) yes C1 C2 1.381(4) ? C1 C6 1.401(4) ? C2 C3 1.375(4) ? C2 H2 0.9300 ? C3 C4 1.374(4) ? C3 H3 0.9300 ? C4 C5 1.379(4) ? C4 H4 0.9300 ? C5 C6 1.384(4) ? C5 H5 0.9300 ? C6 C7 1.483(4) ? C8 C13 1.394(3) ? C8 C9 1.398(4) ? C9 C10 1.369(4) ? C9 H9 0.9300 ? C10 C11 1.387(4) ? C10 H10 0.9300 ? C11 C12 1.378(4) ? C11 H11 0.9300 ? C12 C13 1.386(4) ? C12 H12 0.9300 ? C14 C15 1.498(4) yes C14 H14A 0.9700 ? C14 H14B 0.9700 ? C15 H15A 0.9600 ? C15 H15B 0.9600 ? C15 H15C 0.9600 ? C16 C17 1.485(5) yes C16 H16A 0.9700 ? C16 H16B 0.9700 ? C17 H17A 0.9600 ? C17 H17B 0.9600 ? C17 H17C 0.9600 ? 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 C7 N1 C13 106.6(2) yes C7 N1 C14 127.5(2) yes C13 N1 C14 125.1(2) yes C7 N2 C8 104.5(2) yes C1 O1 C16 118.5(2) yes O1 C1 C2 124.9(2) yes O1 C1 C6 115.3(2) yes C2 C1 C6 119.7(3) ? C3 C2 C1 119.8(3) ? C3 C2 H2 120.1 ? C1 C2 H2 120.1 ? C4 C3 C2 121.5(3) ? C4 C3 H3 119.3 ? C2 C3 H3 119.3 ? C3 C4 C5 118.7(3) ? C3 C4 H4 120.6 ? C5 C4 H4 120.6 ? C4 C5 C6 121.4(3) ? C4 C5 H5 119.3 ? C6 C5 H5 119.3 ? C5 C6 C1 118.9(3) ? C5 C6 C7 120.5(2) ? C1 C6 C7 120.6(2) ? N2 C7 N1 113.4(2) ? N2 C7 C6 125.6(2) ? N1 C7 C6 121.0(2) ? N2 C8 C13 110.4(2) ? N2 C8 C9 130.6(2) ? C13 C8 C9 119.0(2) ? C10 C9 C8 118.2(3) ? C10 C9 H9 120.9 ? C8 C9 H9 120.9 ? C9 C10 C11 122.0(3) ? C9 C10 H10 119.0 ? C11 C10 H10 119.0 ? C12 C11 C10 121.3(3) ? C12 C11 H11 119.4 ? C10 C11 H11 119.4 ? C11 C12 C13 116.6(3) ? C11 C12 H12 121.7 ? C13 C12 H12 121.7 ? N1 C13 C12 131.9(2) ? N1 C13 C8 105.1(2) ? C12 C13 C8 123.1(3) ? N1 C14 C15 111.8(2) yes N1 C14 H14A 109.3 ? C15 C14 H14A 109.3 ? N1 C14 H14B 109.3 ? C15 C14 H14B 109.3 ? H14A C14 H14B 107.9 ? C14 C15 H15A 109.5 ? C14 C15 H15B 109.5 ? H15A C15 H15B 109.5 ? C14 C15 H15C 109.5 ? H15A C15 H15C 109.5 ? H15B C15 H15C 109.5 ? O1 C16 C17 107.8(3) yes O1 C16 H16A 110.1 ? C17 C16 H16A 110.1 ? O1 C16 H16B 110.1 ? C17 C16 H16B 110.1 ? H16A C16 H16B 108.5 ? C16 C17 H17A 109.5 ? C16 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? C16 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? 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 C16 O1 C1 C2 -4.6(4) C16 O1 C1 C6 176.0(3) O1 C1 C2 C3 178.4(3) C6 C1 C2 C3 -2.2(4) C1 C2 C3 C4 1.3(5) C2 C3 C4 C5 0.3(5) C3 C4 C5 C6 -1.0(5) C4 C5 C6 C1 0.1(4) C4 C5 C6 C7 -178.0(3) O1 C1 C6 C5 -179.1(3) C2 C1 C6 C5 1.5(4) O1 C1 C6 C7 -1.0(3) C2 C1 C6 C7 179.6(3) C8 N2 C7 N1 -0.6(3) C8 N2 C7 C6 177.4(2) C13 N1 C7 N2 0.4(3) C14 N1 C7 N2 170.7(2) C13 N1 C7 C6 -177.7(2) C14 N1 C7 C6 -7.3(4) C5 C6 C7 N2 -77.6(3) C1 C6 C7 N2 104.3(3) C5 C6 C7 N1 100.2(3) C1 C6 C7 N1 -77.8(3) C7 N2 C8 C13 0.5(3) C7 N2 C8 C9 -178.8(3) N2 C8 C9 C10 179.1(3) C13 C8 C9 C10 -0.1(4) C8 C9 C10 C11 -0.2(4) C9 C10 C11 C12 0.2(4) C10 C11 C12 C13 0.2(4) C7 N1 C13 C12 178.3(3) C14 N1 C13 C12 7.7(4) C7 N1 C13 C8 0.0(3) C14 N1 C13 C8 -170.7(2) C11 C12 C13 N1 -178.6(3) C11 C12 C13 C8 -0.6(4) N2 C8 C13 N1 -0.3(3) C9 C8 C13 N1 179.1(2) N2 C8 C13 C12 -178.9(2) C9 C8 C13 C12 0.6(4) C7 N1 C14 C15 -89.0(3) C13 N1 C14 C15 79.7(3) C1 O1 C16 C17 -179.3(3)