#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006113.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_2006113 loop_ _publ_author_name 'Ojala, W. H.' 'Iyer, R. A.' 'Hanna, P. E.' 'Gleason, W. B.' _publ_section_title ; Heterocyclic N-Acetoxyarylamines, Models for the Putative Ultimate Carcinogens of Aromatic Amines: 2-Acetoxyamino-5-phenylpyridine and 2-Acetoxyaminopyridine ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 634 _journal_page_last 637 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C13 H12 N2 O2 ' _chemical_formula_sum 'C13 H12 N2 O2' _chemical_formula_weight 228.25 _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 TEXSAN _cell_angle_alpha 90 _cell_angle_beta 90.463(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.246(2) _cell_length_b 5.524(2) _cell_length_c 19.9730(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 24 _cell_volume 1130.4(5) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1985)' _computing_publication_material 'TEXSAN, PLUTON92 (Spek, 1992), ORTEPII (Johnson, 1976)' _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 173.2 _diffrn_measurement_device AFC6S _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .025 _diffrn_reflns_limit_h_max '12; 0' _diffrn_reflns_limit_h_min '0; -10' _diffrn_reflns_limit_k_max '6; 0' _diffrn_reflns_limit_k_min '0; -5' _diffrn_reflns_limit_l_max '24; 19' _diffrn_reflns_limit_l_min '-24; -19' _diffrn_reflns_number 3873 _diffrn_reflns_reduction_process TEXSAN _diffrn_reflns_theta_max 70.08 _diffrn_reflns_theta_min 5 _diffrn_standards_decay_% -0.63 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.715 _exptl_absorpt_correction_T_max 0.918 _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_type '\y scans (North, Phillips & Mathews, 1968)' _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 480.00 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.20 _refine_diff_density_min -0.19 _refine_ls_extinction_coef 8.58e-6 _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_goodness_of_fit_obs 2.165 _refine_ls_hydrogen_treatment refxyz _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 1443 _refine_ls_R_factor_obs 0.0369 _refine_ls_shift/esd_max 0.0320 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme ' w = 4Fo^2^/\s^2^(Fo^2^) ' _refine_ls_wR_factor_obs 0.0464 _reflns_number_observed 1443 _reflns_number_total 2317 _reflns_observed_criterion '[I > 3\s (I)]' _[local]_cod_data_source_file fr1017.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c ' _[local]_cod_chemical_formula_sum_orig 'C13 H12 N2 O2 ' _cod_original_cell_volume 1130.3(3) _cod_database_code 2006113 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y,1/2-z' ' -x, -y, -z' ' +x,1/2-y,1/2+z' 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 0.0387(7) 0.0267(7) 0.0370(7) -0.0006(6) 0.0076(6) 0.0021(6) O2 0.0564(10) 0.0381(9) 0.1010(10) -0.0067(8) 0.0419(10) -0.0140(9) N1 0.0369(8) 0.0269(8) 0.0335(8) -0.0025(7) 0.0032(7) -0.0030(7) N2 0.0366(8) 0.0252(8) 0.0343(8) -0.0045(7) 0.0045(7) -0.0011(7) C1 0.0291(8) 0.0260(9) 0.0277(8) 0.0021(8) -0.0026(7) 0.0009(7) C2 0.0367(9) 0.0300(10) 0.0341(9) -0.0075(8) 0.0001(8) -0.0024(8) C3 0.0385(10) 0.0300(10) 0.0308(9) -0.0027(8) -0.0017(8) -0.0050(8) C4 0.0276(8) 0.0272(9) 0.0275(8) 0.0018(8) -0.0047(7) 0.0008(7) C5 0.0334(9) 0.0272(10) 0.0336(9) -0.0034(8) 0.0010(7) -0.0004(8) C6 0.0294(9) 0.0340(10) 0.0404(10) 0.0006(8) 0.0010(8) -0.0018(9) C7 0.0380(10) 0.0350(10) 0.0480(10) -0.0041(10) 0.0014(9) 0.0039(10) C8 0.0284(8) 0.0310(10) 0.0292(8) 0.0034(8) -0.0047(7) 0.0018(8) C9 0.0355(10) 0.0430(10) 0.0394(10) -0.0047(9) 0.0038(8) -0.0096(9) C10 0.0440(10) 0.0540(10) 0.0390(10) 0.0000(10) 0.0041(9) -0.0120(10) C11 0.0360(10) 0.0610(10) 0.0338(10) 0.0030(10) 0.0061(8) 0.0040(10) C12 0.0480(10) 0.0540(10) 0.0540(10) -0.0140(10) 0.0150(10) -0.0030(10) C13 0.0460(10) 0.0420(10) 0.0460(10) -0.0100(10) 0.0096(9) -0.0078(10) 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 O1 -0.18350(10) 0.0245(2) 0.49089(6) 0.0341(4) Uij O2 -0.3271(2) 0.2207(3) 0.55435(9) 0.0651(5) Uij N1 0.03617(14) 0.4210(3) 0.41417(7) 0.0324(4) Uij N2 -0.1320(2) 0.2586(3) 0.47407(8) 0.0320(4) Uij C1 -0.0440(2) 0.2327(3) 0.42134(8) 0.0276(4) Uij C2 -0.0461(2) 0.0379(3) 0.37751(9) 0.0335(5) Uij C3 0.0416(2) 0.0378(4) 0.32563(9) 0.0333(5) Uij C4 0.1285(2) 0.2297(3) 0.31617(8) 0.0275(4) Uij C5 0.1186(2) 0.4167(3) 0.36225(9) 0.0314(5) Uij C6 -0.2912(2) 0.0365(4) 0.52890(9) 0.0347(5) Uij C7 -0.3545(2) -0.2045(4) 0.53502(11) 0.0401(6) Uij C8 0.2255(2) 0.2340(3) 0.26121(9) 0.0294(4) Uij C9 0.2244(2) 0.0589(4) 0.21118(10) 0.0393(5) Uij C10 0.3149(2) 0.0625(4) 0.15974(10) 0.0456(6) Uij C11 0.4082(2) 0.2410(4) 0.15683(10) 0.0434(6) Uij C12 0.4110(2) 0.4160(4) 0.20597(11) 0.0520(7) Uij C13 0.3211(2) 0.4119(4) 0.25737(11) 0.0448(6) Uij H2 -0.107(2) -0.091(4) 0.3836(9) 0.0392 Uij H2N -0.097(2) 0.330(4) 0.5108(10) 0.0373 Uij H3 0.037(2) -0.101(4) 0.2964(9) 0.0365 Uij H5 0.175(2) 0.558(4) 0.3597(9) 0.0358 Uij H7A -0.384(2) -0.220(4) 0.5790(10) 0.0453 Uij H7B -0.431(2) -0.211(4) 0.5070(10) 0.0453 Uij H7C -0.300(2) -0.334(4) 0.5207(10) 0.0453 Uij H9 0.156(2) -0.068(4) 0.2116(10) 0.0453 Uij H10 0.310(2) -0.062(4) 0.1300(10) 0.0513 Uij H11 0.470(2) 0.244(4) 0.1210(10) 0.0474 Uij H12 0.480(2) 0.546(4) 0.2050(10) 0.0572 Uij H13 0.330(2) 0.533(4) 0.2900(10) 0.0527 Uij loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.018 0.009 'International Tables' H 0.000 0.000 'International Tables' O 0.049 0.032 'International Tables' N 0.031 0.018 'International Tables' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 1 2 -1 0 4 0 1 3 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 N2 O1 C6 113.00(10) yes C1 N1 C5 117.5(2) yes O1 N2 C1 108.90(10) yes O1 N2 H2N 110.0(10) no C1 N2 H2N 113.0(10) no N1 C1 N2 113.7(2) yes N1 C1 C2 122.9(2) yes N2 C1 C2 123.2(2) yes C1 C2 C3 118.0(2) yes C1 C2 H2 120.0(10) no C3 C2 H2 121.0(10) no C2 C3 C4 121.4(2) yes C2 C3 H3 115.0(10) no C4 C3 H3 123.0(10) no C3 C4 C5 115.2(2) yes C3 C4 C8 122.8(2) yes C5 C4 C8 122.0(2) yes N1 C5 C4 125.1(2) yes N1 C5 H5 113.0(10) no C4 C5 H5 120.0(10) no O1 C6 O2 122.5(2) yes O1 C6 C7 111.3(2) yes O2 C6 C7 126.2(2) yes C6 C7 H7A 107.0(10) no C6 C7 H7B 109.0(10) no C6 C7 H7C 113.0(10) no H7A C7 H7B 106.0(10) no H7A C7 H7C 114.0(10) no H7B C7 H7C 105.0(10) no C4 C8 C9 121.2(2) yes C4 C8 C13 121.8(2) yes C9 C8 C13 117.0(2) no C8 C9 C10 121.3(2) no C8 C9 H9 119.0(10) no C10 C9 H9 119.0(10) no C9 C10 C11 120.6(2) no C9 C10 H10 116.0(10) no C11 C10 H10 123.0(10) no C10 C11 C12 118.9(2) no C10 C11 H11 120.0(10) no C12 C11 H11 120.0(10) no C11 C12 C13 120.4(2) no C11 C12 H12 120.0(10) no C13 C12 H12 119.0(10) no C8 C13 C12 121.7(2) no C8 C13 H13 121.0(10) no C12 C13 H13 116.0(10) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 N2 1.437(2) yes O1 C6 1.346(2) yes O2 C6 1.197(2) yes N1 C1 1.334(2) yes N1 C5 1.343(2) yes N2 C1 1.399(2) yes N2 H2N 0.90(2) no C1 C2 1.387(3) yes C2 C3 1.377(3) yes C2 H2 0.95(2) no C3 C4 1.398(3) yes C3 H3 0.97(2) no C4 C5 1.388(3) yes C4 C8 1.487(2) yes C5 H5 0.97(2) no C6 C7 1.486(3) yes C7 H7A 0.93(2) no C7 H7B 0.96(2) no C7 H7C 0.96(2) no C8 C9 1.390(3) no C8 C13 1.390(3) no C9 C10 1.390(3) no C9 H9 0.99(2) no C10 C11 1.375(3) no C10 H10 0.91(2) no C11 C12 1.378(3) no C11 H11 0.95(2) no C12 C13 1.385(3) no C12 H12 1.00(2) no C13 H13 0.94(2) no