#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003734.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_2003734 loop_ _publ_author_name 'Kowalski, A.' _publ_section_title ; 2-Methyl-4-nitro-1-phenylimidazole and 2-Methyl-1-(p-methylphenyl)-4-nitroimidazole ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1670 _journal_page_last 1672 _journal_paper_doi 10.1107/S0108270195001831 _journal_volume 51 _journal_year 1995 _chemical_formula_sum 'C11 H11 N3 O2' _chemical_formula_weight 217.23 _chemical_name_systematic ; 2-methyl-1-(p-methylphenyl)-4-nitroimidazole ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 103.58(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.259(2) _cell_length_b 7.805(2) _cell_length_c 16.774(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29 _cell_measurement_theta_min 14 _cell_volume 1051.0(4) _computing_data_collection 'Kuma KM4 software (1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 295(2) _diffrn_measurement_device 'Kuma KM4 automated four-circle \k-axis diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.1703 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 2014 _diffrn_reflns_theta_max 82 _diffrn_reflns_theta_min 5 _diffrn_standards_decay_% 2 _diffrn_standards_interval_count 50 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.808 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.373(1) _exptl_crystal_density_meas 1.40 _exptl_crystal_density_method flotation _exptl_crystal_description 'irregularly shaped' _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.175 _refine_diff_density_min -0.161 _refine_ls_extinction_coef 0.033(7) _refine_ls_extinction_method 'F~c~^*^ = kF~c~[1+0.001\xF~c~^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_obs 1.266 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 1783 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.136 _refine_ls_restrained_S_obs 1.266 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_obs 0.0466 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ;calc w = 1/[\s^2^(F~o~^2^) + (0.0959P)^2^ + 0.0352P] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1640 _refine_ls_wR_factor_obs 0.1369 _reflns_number_observed 1044 _reflns_number_total 1856 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ab1197.cif _cod_data_source_block II _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2003734 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 O1 0.0798(13) 0.0126(12) 0.0191(10) 0.0970(15) -0.0089(10) 0.0623(12) O2 0.0651(12) -0.0010(11) -0.0030(10) 0.107(2) -0.0016(10) 0.0565(11) N1 0.0425(11) 0.0030(9) 0.0044(8) 0.0561(10) 0.0021(8) 0.0463(10) N2 0.0464(11) 0.0054(10) 0.0056(10) 0.0648(12) 0.0034(9) 0.0594(13) N3 0.0516(13) -0.0041(11) 0.0081(11) 0.0708(13) -0.0008(10) 0.0505(12) C1 0.0445(13) 0.0023(11) 0.0049(11) 0.0589(13) 0.0002(10) 0.0514(14) C2 0.0444(13) -0.0030(10) 0.0078(11) 0.0594(13) 0.0022(9) 0.0486(13) C3 0.0437(13) 0.0040(11) 0.0112(12) 0.0583(12) 0.0006(10) 0.0531(13) C4 0.0445(12) 0.0000(10) 0.0048(10) 0.0493(11) 0.0002(9) 0.0496(12) C5 0.0493(15) -0.0048(11) 0.0102(13) 0.0611(14) 0.0003(11) 0.0580(15) C6 0.0435(14) -0.0079(12) 0.0018(12) 0.0665(15) -0.0032(12) 0.068(2) C7 0.0511(14) -0.0028(11) 0.0027(11) 0.0522(12) -0.0045(10) 0.0537(13) C8 0.0510(15) -0.0029(11) 0.0113(12) 0.0669(14) 0.0013(10) 0.0535(14) C9 0.0418(14) -0.0017(11) 0.0043(11) 0.0646(14) -0.0007(10) 0.0529(14) C10 0.062(2) 0.019(2) 0.009(2) 0.078(2) -0.0036(15) 0.071(2) C11 0.062(2) -0.004(2) -0.005(2) 0.082(2) 0.0010(14) 0.060(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 O1 1 0.2281(3) 0.5272(3) 0.59776(12) 0.0793(7) Uani d O O2 1 0.4628(3) 0.3992(3) 0.63850(13) 0.0790(6) Uani d O N1 1 0.2384(2) 0.3150(2) 0.37683(11) 0.0493(5) Uani d N N2 1 0.4369(2) 0.2593(3) 0.48751(13) 0.0580(6) Uani d N N3 1 0.3395(3) 0.4348(3) 0.58565(13) 0.0583(6) Uani d N C1 1 0.3848(3) 0.2285(3) 0.40852(15) 0.0527(6) Uani d C C2 1 0.3213(3) 0.3667(3) 0.50573(14) 0.0513(6) Uani d C C3 1 0.1979(3) 0.4022(3) 0.43919(15) 0.0517(6) Uani d C C4 1 0.1448(3) 0.3201(3) 0.29307(14) 0.0489(6) Uani d C C5 1 -0.0223(3) 0.2822(3) 0.2752(2) 0.0566(6) Uani d C C6 1 -0.1135(4) 0.2940(4) 0.1949(2) 0.0611(7) Uani d C C7 1 -0.0403(3) 0.3417(3) 0.1327(2) 0.0539(6) Uani d C C8 1 0.1291(3) 0.3760(3) 0.1525(2) 0.0573(7) Uani d C C9 1 0.2210(3) 0.3662(3) 0.23210(15) 0.0542(6) Uani d C C10 1 0.4672(5) 0.1143(5) 0.3607(2) 0.0713(8) Uani d C C11 1 -0.1412(5) 0.3599(5) 0.0463(2) 0.0712(8) Uani d C H1 1 0.1032(29) 0.4734(31) 0.4338(14) 0.046(6) Uiso d H H2 1 -0.0802(33) 0.2604(35) 0.3159(18) 0.064(8) Uiso d H H3 1 -0.2261(43) 0.2668(38) 0.1828(19) 0.071(8) Uiso d H H4 1 0.1904(31) 0.3988(31) 0.1085(17) 0.056(6) Uiso d H H5 1 0.3391(37) 0.3952(34) 0.2454(17) 0.062(7) Uiso d H H6 1 0.5197(46) 0.0151(57) 0.3958(24) 0.103(11) Uiso d H H7 1 0.3810(48) 0.0746(48) 0.3075(28) 0.097(10) Uiso d H H8 1 0.5440(49) 0.1728(50) 0.3433(23) 0.092(12) Uiso d H H9 1 -0.0829(52) 0.3210(56) 0.0104(30) 0.110(13) Uiso d H H10 1 -0.1626(44) 0.4832(65) 0.0338(25) 0.107(12) Uiso d H H11 1 -0.2436(54) 0.3165(49) 0.0447(23) 0.088(11) 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' 0.0181 0.0091 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' 0.0311 0.0180 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0492 0.0322 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 C3 N1 C1 107.6(2) y C3 N1 C4 124.6(2) y C1 N1 C4 127.8(2) y C1 N2 C2 105.0(2) y O2 N3 O1 123.2(2) y O2 N3 C2 119.3(2) y O1 N3 C2 117.5(2) y N2 C1 N1 110.4(2) y N2 C1 C10 125.2(2) y N1 C1 C10 124.3(2) y C3 C2 N2 112.0(2) y C3 C2 N3 126.6(2) y N2 C2 N3 121.4(2) y C2 C3 N1 105.0(2) no C2 C3 H1 130.2(14) no N1 C3 H1 124.7(14) no C9 C4 C5 120.5(2) y C9 C4 N1 120.2(2) y C5 C4 N1 119.3(2) y C4 C5 C6 119.2(2) y C4 C5 H2 122.6(17) no C6 C5 H2 117.9(17) no C7 C6 C5 121.4(2) y C7 C6 H3 119.5(19) no C5 C6 H3 119.1(19) no C6 C7 C8 118.0(2) y C6 C7 C11 121.0(3) y C8 C7 C11 120.9(3) y C9 C8 C7 121.2(2) y C9 C8 H4 117.8(15) no C7 C8 H4 120.8(15) no C4 C9 C8 119.6(2) y C4 C9 H5 120.0(16) no C8 C9 H5 120.3(17) no C1 C10 H6 110.(2) no C1 C10 H7 110.(2) no H6 C10 H7 113.(3) no C1 C10 H8 109.(3) no H6 C10 H8 110.(3) no H7 C10 H8 106.(3) no C7 C11 H9 110.(3) no C7 C11 H10 109.(2) no H9 C11 H10 106.(4) no C7 C11 H11 107.(2) no H9 C11 H11 120.(4) no H10 C11 H11 104.(3) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N3 1.223(3) y O2 N3 1.215(3) y N1 C3 1.354(3) y N1 C1 1.378(3) y N1 C4 1.436(3) y N2 C1 1.315(3) y N2 C2 1.359(3) y N3 C2 1.417(3) y C1 C10 1.469(4) y C2 C3 1.352(4) y C3 H1 0.95(2) no C4 C9 1.369(4) y C4 C5 1.374(4) y C5 C6 1.383(4) y C5 H2 0.94(3) no C6 C7 1.374(4) y C6 H3 0.93(3) no C7 C8 1.386(4) y C7 C11 1.500(4) y C8 C9 1.374(4) y C8 H4 1.01(3) no C9 H5 0.97(3) no C10 H6 1.01(4) no C10 H7 1.05(4) no C10 H8 0.88(4) no C11 H9 0.91(5) no C11 H10 0.99(5) no C11 H11 0.91(4) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21138844 2 PubChem 14906222