#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/23/2202330.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_2202330 loop_ _publ_author_name 'Reck, G\"unter' 'Orgzall, Ingo' 'Schulz, Burkhard' _publ_section_title ; 2,5-Di-p-tolyl-1,3,4-oxadiazole ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1135 _journal_page_last o1136 _journal_paper_doi 10.1107/S1600536803014867 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C16 H14 N2 O' _chemical_formula_moiety 'C16 H14 N2 O' _chemical_formula_sum 'C16 H14 N2 O' _chemical_formula_weight 250.29 _chemical_name_systematic ; 2,5-Di-p-tolyl-1,3,4-oxadiazole ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 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 116.62(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.404(2) _cell_length_b 11.751(2) _cell_length_c 10.8700(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 12 _cell_volume 1302.3(4) _computing_cell_refinement 'CAD-4 Operations Manual' _computing_data_collection 'CAD-4 Operations Manual (Enraf-Nonius, 1977)' _computing_data_reduction 'PROCESS_in MoLEN (Fair, 1990)' _computing_molecular_graphics 'SHELXTL-NT (Sheldrick, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method 2\q-\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.1213 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 1207 _diffrn_reflns_theta_full 25.05 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_min 2.64 _diffrn_standards_decay_% 0.8 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 528 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.265 _refine_diff_density_min -0.187 _refine_ls_extinction_coef 0.005(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 89 _refine_ls_number_reflns 1155 _refine_ls_number_restraints 23 _refine_ls_restrained_S_all 0.897 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0531 _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^)+(0.1082P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1528 _refine_ls_wR_factor_ref 0.1562 _reflns_number_gt 606 _reflns_number_total 1155 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6298.cif _cod_data_source_block I _cod_original_cell_volume 1302.3(3) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2202330 _cod_database_fobs_code 2202330 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.0000 -0.00372(17) 0.2500 0.0600(6) Uani d SU 1 . . O N3 0.04729(18) 0.17335(17) 0.31948(18) 0.0669(6) Uani d U 1 . . N C2 0.0712(2) 0.06886(19) 0.3552(2) 0.0560(6) Uani d U 1 . . C C6 0.15820(18) 0.01850(18) 0.4872(2) 0.0538(6) Uani d U 1 . . C C7 0.2450(2) 0.08726(19) 0.5929(2) 0.0624(6) Uani d U 1 . . C H7 0.2469 0.1652 0.5793 0.081 Uiso calc R 1 . . H C8 0.3282(2) 0.0399(2) 0.7179(2) 0.0669(7) Uani d U 1 . . C H8 0.3862 0.0866 0.7878 0.087 Uiso calc R 1 . . H C9 0.3274(2) -0.0756(2) 0.7415(2) 0.0626(7) Uani d U 1 . . C C10 0.2400(2) -0.1417(2) 0.6365(3) 0.0729(7) Uani d U 1 . . C H10 0.2374 -0.2196 0.6504 0.081(8) Uiso calc R 1 . . H C11 0.1559(2) -0.0959(2) 0.5107(3) 0.0703(7) Uani d U 1 . . C H11 0.0974 -0.1429 0.4416 0.091 Uiso calc R 1 . . H C12 0.4204(2) -0.1279(3) 0.8760(2) 0.0845(9) Uani d U 1 . . C H121 0.4742 -0.0695 0.9369 0.110 Uiso calc R 1 . . H H122 0.4752 -0.1823 0.8604 0.110 Uiso calc R 1 . . H H123 0.3715 -0.1654 0.9166 0.110 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 O1 0.0650(12) 0.0550(13) 0.0596(12) 0.000 0.0275(10) 0.000 N3 0.0822(14) 0.0590(13) 0.0583(11) -0.0002(9) 0.0304(10) -0.0006(9) C2 0.0584(11) 0.0596(14) 0.0575(12) -0.0044(10) 0.0327(10) -0.0060(10) C6 0.0533(12) 0.0585(13) 0.0557(12) -0.0015(9) 0.0299(10) -0.0026(10) C7 0.0742(13) 0.0562(14) 0.0611(13) 0.0003(10) 0.0343(11) 0.0026(10) C8 0.0764(14) 0.0685(15) 0.0595(14) -0.0045(12) 0.0338(11) -0.0052(11) C9 0.0612(13) 0.0747(16) 0.0640(14) 0.0071(10) 0.0389(12) 0.0085(11) C10 0.0825(15) 0.0557(14) 0.0859(17) -0.0019(12) 0.0424(14) 0.0103(13) C11 0.0739(14) 0.0624(15) 0.0718(15) -0.0065(11) 0.0302(12) 0.0023(12) C12 0.0837(17) 0.103(2) 0.0730(17) 0.0117(16) 0.0401(14) 0.0208(15) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle C2 O1 C2 2 102.6(2) C2 N3 N3 2 106.39(12) N3 C2 O1 . 112.29(19) N3 C2 C6 . 130.4(2) O1 C2 C6 . 117.3(2) C11 C6 C7 . 118.8(2) C11 C6 C2 . 121.4(2) C7 C6 C2 . 119.8(2) C8 C7 C6 . 120.0(2) C8 C7 H7 . 120.0 C6 C7 H7 . 120.0 C7 C8 C9 . 121.4(2) C7 C8 H8 . 119.3 C9 C8 H8 . 119.3 C10 C9 C8 . 117.7(2) C10 C9 C12 . 120.8(2) C8 C9 C12 . 121.5(2) C9 C10 C11 . 121.8(2) C9 C10 H10 . 119.1 C11 C10 H10 . 119.1 C6 C11 C10 . 120.3(2) C6 C11 H11 . 119.9 C10 C11 H11 . 119.9 C9 C12 H121 . 109.5 C9 C12 H122 . 109.5 H121 C12 H122 . 109.5 C9 C12 H123 . 109.5 H121 C12 H123 . 109.5 H122 C12 H123 . 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 . 1.365(2) ? O1 C2 2 1.365(2) ? N3 C2 . 1.280(3) ? N3 N3 2 1.409(4) ? C2 C6 . 1.455(3) ? C6 C11 . 1.371(3) ? C6 C7 . 1.390(3) ? C7 C8 . 1.379(3) ? C7 H7 . 0.9300 ? C8 C9 . 1.382(3) ? C8 H8 . 0.9300 ? C9 C10 . 1.372(3) ? C9 C12 . 1.500(3) ? C10 C11 . 1.380(3) ? C10 H10 . 0.9300 ? C11 H11 . 0.9300 ? C12 H121 . 0.9600 ? C12 H122 . 0.9600 ? C12 H123 . 0.9600 ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 17227