#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2006666.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_2006666 _journal_name_full 'Acta Crystallographica Section C' _journal_year 1997 _journal_volume 53 _journal_page_first 1634 _journal_page_last 1635 _publ_section_title ; The 1:1 Complex Formed by 3-Picoline N-Oxide and p-Toluic Acid ; _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'De Almeida Santos, Regina Helena' 'Gambardella, Maria Teresa do Prado' _chemical_formula_moiety 'C6 H7 N O , C8 H8 O2' _chemical_formula_sum 'C14 H15 N O3' _chemical_formula_weight 245.27 _symmetry_cell_setting monoclinic 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' _cell_length_a 13.6819(9) _cell_length_b 7.2379(3) _cell_length_c 14.0407(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.000(10) _cell_angle_gamma 90.00 _cell_volume 1298.11(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295 _exptl_crystal_density_diffrn 1.255 _refine_ls_R_factor_obs .0460 _refine_ls_wR_factor_obs .1324 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol C1 1.0569(2) .3623(3) .3738(2) .0559(5) Uani d . 1 . C H1 1.0392(2) .2544(3) .3355(2) .076 Uiso calc R 1 . H C2 1.1449(2) .3650(3) .4614(2) .0570(5) Uani d . 1 . C C3 1.1689(2) .5270(3) .5164(2) .0662(6) Uani d . 1 . C H3 1.2274(2) .5331(3) .5761(2) .076 Uiso calc R 1 . H C4 1.1063(2) .6797(3) .4828(2) .0713(6) Uani d . 1 . C H4 1.1227(2) .7889(3) .5200(2) .076 Uiso calc R 1 . H C5 1.0201(2) .6721(3) .3949(2) .0603(5) Uani d . 1 . C H5 .9785(2) .7762(3) .3717(2) .076 Uiso calc R 1 . H C6 1.2096(2) .1941(4) .4940(2) .0832(8) Uani d . 1 . C H61 1.1989(9) .1417(11) .5523(7) .076 Uiso calc R 1 . H H62 1.2822(2) .2246(5) .5114(10) .076 Uiso calc R 1 . H H63 1.1893(8) .1062(8) .4391(4) .076 Uiso calc R 1 . H N1 .99628(12) .5131(2) .34277(12) .0522(4) Uani d . 1 . N O1 .91213(12) .5069(2) .25798(13) .0720(5) Uani d . 1 . O C7 .77886(15) .1079(3) .2456(2) .0531(5) Uani d . 1 . C C8 .68449(14) -.0110(3) .20418(15) .0520(5) Uani d . 1 . C C9 .5855(2) .0614(4) .1565(2) .0734(7) Uani d . 1 . C H9 .5764(2) .1887(4) .1492(2) .076 Uiso calc R 1 . H C10 .5000(2) -.0546(4) .1195(2) .0811(7) Uani d . 1 . C H10 .4336(2) -.0039(4) .0887(2) .076 Uiso calc R 1 . H C11 .5108(2) -.2441(4) .1273(2) .0676(6) Uani d . 1 . C C12 .6093(2) -.3141(3) .1748(2) .0703(6) Uani d . 1 . C H12 .6183(2) -.4414(3) .1814(2) .076 Uiso calc R 1 . H C13 .6957(2) -.2006(3) .2129(2) .0627(6) Uani d . 1 . C H13 .7618(2) -.2520(3) .2447(2) .076 Uiso calc R 1 . H C14 .4172(2) -.3701(4) .0832(2) .0914(9) Uani d . 1 . C H141 .4408(2) -.4948(5) .0826(10) .076 Uiso calc R 1 . H H142 .3771(6) -.3321(13) .0148(5) .076 Uiso calc R 1 . H H143 .3744(6) -.3633(16) .1243(7) .076 Uiso calc R 1 . H O2 .76113(13) .2827(2) .21913(15) .0806(6) Uani d . 1 . O H2 .8216(19) .347(4) .2413(19) .076 Uiso d . 1 . H O3 .86361(11) .0516(2) .29953(13) .0711(5) Uani d . 1 . O 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 C1 .0619(12) .0426(11) .0600(12) .0007(9) .0180(10) .0007(9) C2 .0532(11) .0570(12) .0606(11) .0005(9) .0200(9) .0044(9) C3 .0581(12) .0697(15) .0634(13) -.0115(11) .0128(10) -.0045(11) C4 .0776(15) .0534(13) .081(2) -.0134(11) .0260(13) -.0175(11) C5 .0595(12) .0410(10) .0830(14) -.0012(9) .0289(11) -.0012(10) C6 .085(2) .074(2) .080(2) .0217(13) .0162(14) .0138(13) N1 .0480(8) .0438(9) .0616(10) -.0057(7) .0159(7) .0028(7) O1 .0582(8) .0559(9) .0803(10) -.0085(7) -.0013(7) .0117(7) C7 .0503(10) .0482(11) .0574(11) .0003(8) .0150(9) -.0047(9) C8 .0474(10) .0510(11) .0551(11) -.0019(8) .0154(8) -.0048(8) C9 .0533(12) .0569(13) .097(2) .0018(10) .0113(12) .0020(12) C10 .0453(11) .077(2) .107(2) .0003(11) .0111(12) -.0031(15) C11 .0551(12) .0736(15) .0718(13) -.0154(11) .0200(10) -.0103(11) C12 .0656(13) .0522(12) .087(2) -.0089(10) .0192(12) -.0078(11) C13 .0506(11) .0535(12) .0780(14) .0005(9) .0156(10) -.0056(10) C14 .0686(15) .093(2) .106(2) -.0293(14) .0229(14) -.014(2) O2 .0548(9) .0499(9) .1139(14) -.0047(7) .0019(9) .0077(9) O3 .0501(8) .0568(9) .0888(11) .0003(7) .0034(7) -.0020(8) 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 C1 N1 . 1.346(2) y C1 C2 . 1.379(3) ? C1 H1 . .93 ? C2 C3 . 1.377(3) ? C2 C6 . 1.494(3) y C3 C4 . 1.374(3) ? C3 H3 . .93 ? C4 C5 . 1.369(3) ? C4 H4 . .93 ? C5 N1 . 1.340(3) ? C5 H5 . .93 ? C6 H61 . .96 ? C6 H62 . .96 ? C6 H63 . .96 ? N1 O1 . 1.328(2) y C7 O3 . 1.206(2) y C7 O2 . 1.316(3) y C7 C8 . 1.486(3) y C8 C9 . 1.381(3) ? C8 C13 . 1.381(3) ? C9 C10 . 1.382(3) ? C9 H9 . .93 ? C10 C11 . 1.379(4) ? C10 H10 . .93 ? C11 C12 . 1.369(3) ? C11 C14 . 1.512(3) y C12 C13 . 1.380(3) ? C12 H12 . .93 ? C13 H13 . .93 ? C14 H141 . .96 ? C14 H142 . .96 ? C14 H143 . .96 ? O2 H2 . .90(3) y _cod_database_code 2006666