#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2206720.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_2206720 loop_ _publ_author_name 'Mehmet Akkurt' 'Sema \"Ozt\"urk Y\?ild\?ir\?im' 'Ersin Orhan' 'Hasan K\"u\,c\"ukbay' 'Orhan B\"uy\"ukg\"ung\"or' _publ_section_title ; 1-Methoxyethyl-5-nitrobenzimidazole ; _journal_coeditor_code HK6034 _journal_issue 9 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o2804 _journal_page_last o2805 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C10 H11 N3 O3' _chemical_formula_moiety 'C10 H11 N3 O3' _chemical_formula_sum 'C10 H11 N3 O3' _chemical_formula_weight 221.22 _chemical_name_systematic ; 1-Methoxyethyl-5-nitrobenzimidazole ; _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 97.350(12) _cell_angle_beta 94.854(12) _cell_angle_gamma 101.266(12) _cell_formula_units_Z 2 _cell_length_a 4.7940(7) _cell_length_b 8.4531(13) _cell_length_c 13.411(2) _cell_measurement_reflns_used 7061 _cell_measurement_temperature 296 _cell_measurement_theta_max 27.86 _cell_measurement_theta_min 2.72 _cell_volume 525.25(14) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296 _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device '2-circle goniometer' _diffrn_measurement_device_type 'Stoe IPDS-II' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8616 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 27.68 _diffrn_reflns_theta_max 27.68 _diffrn_reflns_theta_min 2.48 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.920 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description plate _exptl_crystal_F_000 232 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.141 _refine_diff_density_min -0.200 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 2443 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.978 _refine_ls_R_factor_all 0.1032 _refine_ls_R_factor_gt 0.0487 _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^)+(0.0607P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1048 _refine_ls_wR_factor_ref 0.1236 _reflns_number_gt 1327 _reflns_number_total 2443 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hk6034.cif loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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_thermal_displace_type _atom_site_occupancy _atom_site_type_symbol O1 0.6727(5) 0.7623(3) 0.40810(15) 0.1142(9) Uani 1.000 O O2 0.2956(4) 0.5922(3) 0.42843(12) 0.1031(8) Uani 1.000 O O3 0.2278(4) 0.47209(17) 0.89320(11) 0.0773(6) Uani 1.000 O N1 0.4909(5) 0.7079(3) 0.46004(14) 0.0760(7) Uani 1.000 N N2 0.5574(4) 0.9718(2) 0.86513(13) 0.0683(6) Uani 1.000 N N3 0.1970(3) 0.75853(18) 0.80550(11) 0.0543(5) Uani 1.000 N C1 0.5115(5) 0.7834(2) 0.56586(14) 0.0594(7) Uani 1.000 C C2 0.7353(6) 0.9169(3) 0.60125(18) 0.0706(8) Uani 1.000 C C3 0.7654(5) 0.9889(3) 0.70051(18) 0.0697(8) Uani 1.000 C C4 0.5711(4) 0.9250(2) 0.76324(14) 0.0561(6) Uani 1.000 C C5 0.3478(4) 0.7912(2) 0.72494(13) 0.0505(6) Uani 1.000 C C6 0.3109(5) 0.7164(2) 0.62499(14) 0.0560(7) Uani 1.000 C C7 0.3337(5) 0.8703(3) 0.88552(16) 0.0631(7) Uani 1.000 C C8 -0.0468(5) 0.6251(3) 0.80638(19) 0.0638(8) Uani 1.000 C C9 0.0397(5) 0.4632(2) 0.80549(16) 0.0620(7) Uani 1.000 C C10 0.2970(8) 0.3200(3) 0.9038(2) 0.0878(10) Uani 1.000 C H2 0.879(6) 0.960(3) 0.559(2) 0.0930 Uiso 1.000 H H3 0.927(6) 1.086(3) 0.7256(19) 0.0930 Uiso 1.000 H H6 0.165(6) 0.628(3) 0.600(2) 0.0930 Uiso 1.000 H H7 0.268(6) 0.869(3) 0.952(2) 0.0930 Uiso 1.000 H H8A -0.177(6) 0.619(3) 0.745(2) 0.0930 Uiso 1.000 H H8B -0.130(6) 0.650(3) 0.870(2) 0.0930 Uiso 1.000 H H9A -0.135(6) 0.374(3) 0.8049(19) 0.0930 Uiso 1.000 H H9B 0.135(6) 0.431(3) 0.743(2) 0.0930 Uiso 1.000 H H10A 0.370(7) 0.277(4) 0.839(3) 0.1160 Uiso 1.000 H H10B 0.118(7) 0.235(4) 0.910(2) 0.1160 Uiso 1.000 H H10C 0.423(7) 0.331(4) 0.958(3) 0.1160 Uiso 1.000 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 O1 0.1401(18) 0.1222(16) 0.0743(12) 0.0128(14) 0.0427(13) -0.0058(11) O2 0.1071(14) 0.1233(15) 0.0573(10) 0.0054(12) -0.0080(9) -0.0277(10) O3 0.0989(12) 0.0620(9) 0.0612(9) 0.0128(8) -0.0189(8) -0.0024(6) N1 0.0912(15) 0.0837(13) 0.0510(10) 0.0264(12) 0.0014(11) -0.0064(10) N2 0.0889(14) 0.0504(9) 0.0557(10) 0.0103(9) -0.0057(9) -0.0131(7) N3 0.0608(10) 0.0510(8) 0.0480(9) 0.0167(7) -0.0031(7) -0.0057(7) C1 0.0707(14) 0.0606(11) 0.0466(11) 0.0226(10) 0.0009(10) -0.0029(9) C2 0.0801(16) 0.0619(13) 0.0686(14) 0.0130(12) 0.0120(12) 0.0053(10) C3 0.0793(15) 0.0483(11) 0.0729(14) 0.0045(10) -0.0008(12) -0.0031(10) C4 0.0691(13) 0.0432(9) 0.0516(11) 0.0166(9) -0.0080(9) -0.0067(8) C5 0.0549(11) 0.0488(10) 0.0470(10) 0.0200(8) -0.0038(8) -0.0032(8) C6 0.0553(12) 0.0558(11) 0.0520(11) 0.0168(9) -0.0093(9) -0.0077(9) C7 0.0826(16) 0.0538(11) 0.0495(11) 0.0214(11) -0.0033(10) -0.0087(9) C8 0.0574(13) 0.0701(13) 0.0601(13) 0.0167(10) 0.0024(10) -0.0066(10) C9 0.0616(13) 0.0582(12) 0.0568(12) 0.0032(10) -0.0045(10) -0.0047(9) C10 0.109(2) 0.0633(15) 0.0839(18) 0.0089(14) -0.0182(16) 0.0173(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N1 1.218(3) yes O2 N1 1.217(3) yes O3 C9 1.405(3) yes O3 C10 1.410(3) yes N1 C1 1.467(3) yes N2 C4 1.384(3) yes N2 C7 1.308(3) yes N3 C5 1.377(2) yes N3 C7 1.361(3) yes N3 C8 1.459(3) yes C1 C2 1.398(3) no C1 C6 1.380(3) no C2 C3 1.375(3) no C3 C4 1.385(3) no C4 C5 1.405(3) no C5 C6 1.388(3) no C8 C9 1.505(3) no C2 H2 0.97(3) no C3 H3 1.01(3) no C6 H6 0.92(3) no C7 H7 0.97(3) no C8 H8A 0.98(3) no C8 H8B 0.99(3) no C9 H9A 1.01(3) no C9 H9B 1.02(3) no C10 H10A 1.02(4) no C10 H10B 1.02(3) no C10 H10C 0.89(4) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 C9 3.335(3) 2_566 no O3 C7 3.321(3) . no O3 N3 2.847(2) . no O1 H2 2.45(3) . no O1 H9B 2.77(3) 2_666 no O1 H2 2.82(3) 2_776 no O2 H6 2.43(3) . no O2 H9B 2.92(3) 2_566 no O2 H6 2.56(3) 2_566 no O2 H8A 2.69(3) 2_566 no O3 H10C 2.66(4) 2_667 no N2 N3 2.248(2) . no N2 C10 3.413(4) 1_565 no N2 C7 3.395(3) 2_677 no N3 O3 2.847(2) . no N3 C3 3.441(3) 1_455 no N3 N2 2.248(2) . no N2 H10A 2.94(3) 1_565 no N2 H7 2.63(3) 2_677 no C2 C6 3.522(4) 1_655 no C3 N3 3.441(3) 1_655 no C3 C5 3.536(3) 1_655 no C4 C8 3.482(3) 1_655 no C5 C3 3.536(3) 1_455 no C6 C9 3.592(3) . no C6 C2 3.522(4) 1_455 no C7 C7 3.586(3) 2_677 no C7 N2 3.395(3) 2_677 no C7 O3 3.321(3) . no C8 C4 3.482(3) 1_455 no C9 O2 3.335(3) 2_566 no C9 C6 3.592(3) . no C10 N2 3.413(4) 1_545 no C4 H8A 3.05(3) 1_655 no C5 H9B 3.06(3) . no C5 H8A 2.95(3) 1_655 no C6 H8A 2.99(3) . no C6 H9B 3.07(3) . no C8 H6 3.03(3) . no C10 H3 3.08(3) 1_445 no H2 O1 2.45(3) . no H2 O1 2.82(3) 2_776 no H2 H2 2.14(4) 2_776 no H3 C10 3.08(3) 1_665 no H6 O2 2.43(3) . no H6 C8 3.03(3) . no H6 O2 2.56(3) 2_566 no H7 H8B 2.45(4) . no H7 N2 2.63(3) 2_677 no H8A C4 3.05(3) 1_455 no H8A C5 2.95(3) 1_455 no H8A C6 2.99(3) . no H8A O2 2.69(3) 2_566 no H8B H7 2.45(4) . no H9A H10A 2.46(4) 1_455 no H9A H10B 2.35(4) . no H9B C5 3.06(3) . no H9B C6 3.07(3) . no H9B H10A 2.32(4) . no H9B O1 2.77(3) 2_666 no H9B O2 2.92(3) 2_566 no H10A N2 2.94(3) 1_545 no H10A H9A 2.46(4) 1_655 no H10A H9B 2.32(4) . no H10B H9A 2.35(4) . no H10C O3 2.66(4) 2_667 no 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 C9 O3 C10 111.92(17) yes O1 N1 O2 122.9(2) yes O1 N1 C1 118.5(2) yes O2 N1 C1 118.6(2) yes C4 N2 C7 104.01(17) yes C5 N3 C7 105.68(16) yes C5 N3 C8 127.05(16) yes C7 N3 C8 127.16(18) yes N1 C1 C2 118.2(2) yes N1 C1 C6 117.88(18) yes C2 C1 C6 123.94(19) no C1 C2 C3 119.9(2) no C2 C3 C4 118.3(2) no N2 C4 C3 129.77(18) yes N2 C4 C5 110.04(16) yes C3 C4 C5 120.20(18) no N3 C5 C4 105.54(15) yes N3 C5 C6 131.64(17) yes C4 C5 C6 122.82(17) no C1 C6 C5 114.78(18) no N2 C7 N3 114.74(19) yes N3 C8 C9 112.40(19) yes O3 C9 C8 108.13(17) yes C1 C2 H2 122.7(16) no C3 C2 H2 117.3(16) no C2 C3 H3 119.6(15) no C4 C3 H3 122.1(15) no C1 C6 H6 122.4(17) no C5 C6 H6 122.8(17) no N2 C7 H7 124.7(16) no N3 C7 H7 120.6(16) no N3 C8 H8A 107.5(16) no N3 C8 H8B 106.4(16) no C9 C8 H8A 108.1(15) no C9 C8 H8B 108.4(15) no H8A C8 H8B 114(2) no O3 C9 H9A 109.7(15) no O3 C9 H9B 109.8(16) no C8 C9 H9A 110.0(16) no C8 C9 H9B 113.0(15) no H9A C9 H9B 106(2) no O3 C10 H10A 109(2) no O3 C10 H10B 111(2) no O3 C10 H10C 110(2) no H10A C10 H10B 105(3) no H10A C10 H10C 113(3) no H10B C10 H10C 110(3) no 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 C10 O3 C9 C8 173.9(2) no O1 N1 C1 C6 -177.4(2) no O2 N1 C1 C2 -179.6(2) no O1 N1 C1 C2 1.5(3) no O2 N1 C1 C6 1.5(3) no C7 N2 C4 C3 -179.8(2) no C4 N2 C7 N3 0.3(3) no C7 N2 C4 C5 -0.5(2) no C7 N3 C5 C6 179.1(2) no C7 N3 C8 C9 -101.9(2) no C5 N3 C7 N2 -0.1(3) no C8 N3 C5 C6 2.7(3) no C7 N3 C5 C4 -0.2(2) no C8 N3 C5 C4 -176.54(18) no C8 N3 C7 N2 176.3(2) no C5 N3 C8 C9 73.6(3) no C2 C1 C6 C5 -0.5(3) no N1 C1 C2 C3 -178.7(2) no N1 C1 C6 C5 178.36(19) no C6 C1 C2 C3 0.2(4) no C1 C2 C3 C4 0.5(4) no C2 C3 C4 C5 -0.8(3) no C2 C3 C4 N2 178.5(2) no C3 C4 C5 C6 0.5(3) no C3 C4 C5 N3 179.86(18) no N2 C4 C5 C6 -178.92(18) no N2 C4 C5 N3 0.4(2) no N3 C5 C6 C1 -179.01(19) no C4 C5 C6 C1 0.2(3) no N3 C8 C9 O3 61.2(2) no _cod_database_code 2206720