#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/71/2007140.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_2007140 loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'Gambardella, Maria Teresa do Prado' 'Valderrama-N, Jaime' _publ_section_title ; 2:1 Complex of 3-Picoline N-Oxide and Hydroquinone ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 515 _journal_page_last 517 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety '2C6 H7 N O,C6 H6 O2' _chemical_formula_sum 'C12 H13 N O3' _chemical_formula_weight 328.37 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90.00 _cell_angle_beta 105.10(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 11.2065(5) _cell_length_b 6.0273(4) _cell_length_c 12.7077(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 18.23 _cell_measurement_theta_min 10.34 _cell_volume 828.70(14) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'SDP-VAX (Frenz, 1978)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SDP-VAX _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 295 _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.0097 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1759 _diffrn_reflns_theta_max 26.29 _diffrn_reflns_theta_min 2.82 _diffrn_standards_decay_% 0.71 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_meas not_measured _exptl_crystal_description transparent_prisms _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.205 _refine_diff_density_min -0.184 _refine_ls_extinction_coef 0.032(7) _refine_ls_extinction_method SHELXL93_(Sheldrick,_1993) _refine_ls_goodness_of_fit_all 1.022 _refine_ls_goodness_of_fit_obs 0.988 _refine_ls_hydrogen_treatment H_atoms:_see_text _refine_ls_matrix_type full _refine_ls_number_parameters 113 _refine_ls_number_reflns 1683 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_restrained_S_obs 0.988 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_obs .040 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme '1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.1853P) where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1374 _refine_ls_wR_factor_obs .123 _reflns_number_observed 1446 _reflns_number_total 1683 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file bk1345.cif _[local]_cod_data_source_block global _[local]_cod_cif_authors_sg_H-M 'P 21/n' _[local]_cod_chemical_formula_sum_orig 'C12 H13 N1 O3' _cod_original_cell_volume 828.69(7) _cod_database_code 2007140 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .73492(10) -.5810(2) .83850(10) .0609(4) Uani d . 1 . O N1 .85135(10) -.5290(2) .84389(9) .0435(3) Uani d . 1 . N C7 .92121(13) -.6700(2) .80249(11) .0445(4) Uani d . 1 . C H7 .88669(13) -.8011(2) .76962(11) .076 Uiso calc R 1 . H C8 1.04303(13) -.6217(3) .80841(11) .0455(4) Uani d . 1 . C C9 1.09199(14) -.4256(3) .85758(12) .0509(4) Uani d . 1 . C H9 1.17434(14) -.3903(3) .86382(12) .076 Uiso calc R 1 . H C10 1.01846(15) -.2828(3) .89718(13) .0519(4) Uani d . 1 . C H10 1.05089(15) -.1497(3) .92927(13) .076 Uiso calc R 1 . H C11 .89745(14) -.3358(2) .88961(12) .0482(4) Uani d . 1 . C H11 .84765(14) -.2385(2) .91598(12) .076 Uiso calc R 1 . H C12 1.1184(2) -.7806(3) .76033(15) .0645(5) Uani d . 1 . C H121 1.1891(2) -.8284(3) .81614(15) .076 Uiso calc R 1 . H H122 1.1453(2) -.7075(3) .70341(15) .076 Uiso calc R 1 . H H123 1.0688(2) -.9070(3) .73081(15) .076 Uiso calc R 1 . H O2 .72068(10) -.9499(2) .94383(10) .0568(4) Uani d . 1 . O HO2 .7205(19) -.813(4) .9073(17) .076 Uiso d . 1 . H C1 .61082(12) -.9708(2) .97029(11) .0407(3) Uani d . 1 . C C2 .52438(13) -.8013(2) .95551(12) .0441(4) Uani d . 1 . C H2 .54005(13) -.6671(2) .92554(12) .076 Uiso calc R 1 . H C6 .58512(13) -1.1696(2) 1.01493(12) .0453(4) Uani d . 1 . C H6 .64219(13) -1.2849(2) 1.02513(12) .076 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 .0372(6) .0608(7) .0873(8) -.0007(5) .0209(5) .0151(6) N1 .0370(6) .0451(7) .0489(6) .0005(5) .0122(5) .0098(5) C7 .0430(8) .0438(8) .0450(7) -.0001(6) .0083(6) .0023(6) C8 .0428(7) .0557(9) .0387(7) .0040(6) .0118(5) .0070(6) C9 .0415(7) .0592(10) .0524(8) -.0077(6) .0129(6) .0070(7) C10 .0549(9) .0453(8) .0541(8) -.0076(6) .0114(7) .0010(6) C11 .0531(8) .0436(8) .0503(8) .0044(6) .0174(6) .0049(6) C12 .0563(10) .0803(12) .0598(10) .0109(9) .0201(8) -.0065(9) O2 .0427(6) .0507(7) .0830(8) .0013(5) .0275(5) .0037(6) C1 .0359(7) .0406(7) .0453(7) -.0013(5) .0104(5) -.0044(5) C2 .0434(7) .0364(7) .0522(8) .0002(5) .0119(6) .0038(6) C6 .0398(7) .0373(7) .0579(8) .0057(5) .0111(6) .0005(6) 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 N1 . 1.3262(15) y N1 C11 . 1.343(2) y N1 C7 . 1.351(2) y C7 C8 . 1.378(2) ? C8 C9 . 1.382(2) ? C8 C12 . 1.508(2) y C9 C10 . 1.374(2) ? C10 C11 . 1.372(2) ? O2 C1 . 1.364(2) y C1 C2 . 1.387(2) y C1 C6 . 1.388(2) y C2 C6 3_637 1.385(2) ? C6 C2 3_637 1.385(2) ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 International_Tables_Vol_IV_Table_2.3.1 H 0 0 International_Tables_Vol_IV_Table_2.3.1 O .047 .032 International_Tables_Vol_IV_Table_2.3.1 N .029 .018 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 -3 0 6 0 -2 -1 -1 -6 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle _geom_angle_publ_flag O1 N1 C11 . 119.32(13) y O1 N1 C7 . 119.56(13) y C11 N1 C7 . 121.12(13) y N1 C7 C8 . 120.80(14) ? C7 C8 C9 . 118.42(14) ? C7 C8 C12 . 119.7(2) y C9 C8 C12 . 121.88(14) y C10 C9 C8 . 119.72(14) ? C11 C10 C9 . 120.31(15) ? N1 C11 C10 . 119.59(14) y O2 C1 C2 . 122.82(13) y O2 C1 C6 . 118.52(13) y C2 C1 C6 . 118.66(13) y C6 C2 C1 3_637 120.46(13) ? C2 C6 C1 3_637 120.88(13) ?