#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/66/2006648.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_2006648 loop_ _publ_author_name 'Moreno-Fuquen, Rodolfo' 'Grajales-Tamayo, Mario' 'Gambardella, Maria Teresa do Prado' _publ_contact_author ; Dr Rodolfo Moreno-Fuquen Depto. Qu\'imica - Universidad del Valle Apartado 25360, Cali, Valle Colombia ; _publ_section_title ; The 1:1 Complex Formed by 2-Picoline N-Oxide and 3-Chlorobenzoic Acid ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1635 _journal_page_last 1637 _journal_paper_doi 10.1107/S0108270197007130 _journal_volume 53 _journal_year 1997 _chemical_formula_moiety 'C6 H7 N O , C7 H5 Cl O2' _chemical_formula_sum 'C13 H12 Cl N O3' _chemical_formula_weight 265.69 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 n 1' _atom_type_scat_source ; International Tables for X-ray Crystallography Vol. IV (1974, Tables 2.2.A) ; _cell_angle_alpha 90.00 _cell_angle_beta 92.210(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 3.9241(3) _cell_length_b 13.0404(8) _cell_length_c 12.4181(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 295 _cell_measurement_theta_max 18.49 _cell_measurement_theta_min 10.92 _cell_volume 634.98(7) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'VAXSDP (Frenz, 1978)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material VAXSDP _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_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.0114 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 1471 _diffrn_reflns_theta_max 26.28 _diffrn_reflns_theta_min 3.12 _diffrn_standards_decay_% 0.74 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.30 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description 'Transparent prisms' _exptl_crystal_F_000 276 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.184 _refine_diff_density_min -0.115 _refine_ls_extinction_coef 0.058(12) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 1.067 _refine_ls_goodness_of_fit_obs 1.006 _refine_ls_hydrogen_treatment 'noref except HO2 ref' _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 1471 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.066 _refine_ls_restrained_S_obs 1.006 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_obs .0293 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1175 _refine_ls_wR_factor_obs .1057 _reflns_number_observed 1352 _reflns_number_total 1471 _reflns_observed_criterion 'I > 2.0\s(I)' _cod_data_source_file bs1020.cif _cod_data_source_block default _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P n' _cod_original_formula_sum 'C13 H12 N O3 Cl' _cod_database_code 2006648 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 Cl1 .1049(7) .0823(5) .0468(4) -.0083(5) .0000(4) .0077(4) C1 .0568(15) .0486(13) .0541(14) -.0081(12) -.0056(11) .0056(12) C2 .063(2) .0496(14) .080(2) .0005(12) -.016(2) .0148(14) C3 .068(2) .0423(12) .097(2) .0064(13) -.005(2) -.0052(14) C4 .057(2) .0474(13) .073(2) .0044(12) .0045(13) -.0121(13) C5 .0488(13) .0408(12) .0495(13) -.0059(10) .0035(10) -.0030(9) C6 .0506(12) .0395(11) .0465(12) -.0026(9) .0028(10) .0023(9) C7 .0578(15) .0466(12) .0465(13) -.0060(11) .0018(11) -.0027(10) O1 .098(2) .0665(12) .0482(12) -.0035(13) .0103(11) -.0056(10) O2 .115(2) .0521(10) .0433(9) .0158(12) .0034(12) .0049(8) O3 .114(2) .0573(11) .0439(10) .0089(13) .0002(11) .0046(9) N1 .0575(13) .0466(10) .0473(11) .0083(10) .0007(9) .0070(8) C8 .066(2) .0521(13) .065(2) -.0026(14) .0018(14) .0130(13) C9 .071(2) .063(2) .077(2) -.001(2) -.017(2) -.006(2) C10 .091(3) .079(2) .048(2) .013(2) -.006(2) -.0050(14) C11 .070(2) .073(2) .0539(15) .014(2) .0113(13) .0158(14) C12 .0478(13) .0490(12) .0561(13) .0081(11) .0030(11) .0123(11) C13 .071(2) .0505(14) .083(2) .0013(14) .001(2) .0094(15) 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 Cl1 .9778(2) .16075(7) .15280(7) .0781(3) Uani d . 1 . Cl C1 1.0617(8) .1174(2) .0237(2) .0534(6) Uani d . 1 . C C2 1.2078(9) .0221(2) .0096(3) .0647(8) Uani d . 1 . C H2 1.2634(9) -.0195(2) .0685(3) .076 Uiso calc R 1 . H C3 1.2695(10) -.0099(2) -.0943(4) .0696(8) Uani d . 1 . C H3 1.3656(10) -.0740(2) -.1053(4) .076 Uiso calc R 1 . H C4 1.1899(8) .0524(2) -.1818(3) .0593(7) Uani d . 1 . C H4 1.2356(8) .0304(2) -.2510(3) .076 Uiso calc R 1 . H C5 1.0414(7) .1480(2) -.1664(2) .0463(6) Uani d . 1 . C C6 .9766(7) .1805(2) -.0621(2) .0455(5) Uani d . 1 . C H6 .8771(7) .2441(2) -.0506(2) .076 Uiso calc R 1 . H C7 .9564(7) .2141(2) -.2611(2) .0503(6) Uani d . 1 . C O1 1.0022(8) .1882(2) -.3526(2) .0706(6) Uani d . 1 . O O2 .8215(8) .3022(2) -.2345(2) .0701(7) Uani d . 1 . O HO2 .747(11) .3314(16) -.2890(4) .076 Uiso calc R 1 . H O3 .6663(8) .4313(2) -.3801(2) .0718(7) Uani d . 1 . O N1 .6364(6) .4073(2) -.4834(2) .0505(5) Uani d . 1 . N C8 .4918(10) .3175(2) -.5143(3) .0610(7) Uani d . 1 . C H8 .4208(10) .2719(2) -.4622(3) .076 Uiso calc R 1 . H C9 .4482(9) .2926(3) -.6201(3) .0709(9) Uani d . 1 . C H9 .3496(9) .2303(3) -.6403(3) .076 Uiso calc R 1 . H C10 .5510(11) .3604(3) -.6971(3) .0729(9) Uani d . 1 . C H10 .5216(11) .3448(3) -.7700(3) .076 Uiso calc R 1 . H C11 .6989(9) .4520(3) -.6646(3) .0654(8) Uani d . 1 . C H11 .7679(9) .4984(3) -.7163(3) .076 Uiso calc R 1 . H C12 .7465(7) .4761(2) -.5563(2) .0509(6) Uani d . 1 . C C13 .9073(10) .5724(2) -.5141(3) .0682(8) Uani d . 1 . C H131 .974(6) .6143(9) -.5733(3) .076 Uiso calc R 1 . H H132 1.105(4) .5557(3) -.4695(18) .076 Uiso calc R 1 . H H133 .747(3) .6092(10) -.4723(18) .076 Uiso calc R 1 . H 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 C6 C1 C2 121.9(3) y C6 C1 Cl1 118.0(2) y C2 C1 Cl1 120.1(2) y C1 C2 C3 118.5(3) y C4 C3 C2 120.8(3) y C3 C4 C5 120.0(3) y C6 C5 C4 119.5(3) y C6 C5 C7 121.0(2) y C4 C5 C7 119.5(2) y C1 C6 C5 119.3(2) y O1 C7 O2 123.9(3) y O1 C7 C5 123.1(3) y O2 C7 C5 112.9(2) y O3 N1 C8 120.2(3) y O3 N1 C12 118.1(2) y C8 N1 C12 121.6(3) y N1 C8 C9 121.2(3) y C8 C9 C10 119.4(3) y C11 C10 C9 118.9(3) y C10 C11 C12 121.3(3) y N1 C12 C11 117.6(3) y N1 C12 C13 117.6(3) y C11 C12 C13 124.8(3) y 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 Cl1 C1 . 1.743(3) y C1 C6 . 1.376(4) y C1 C2 . 1.382(5) y C2 C3 . 1.386(6) y C3 C4 . 1.383(5) y C4 C5 . 1.392(4) y C5 C6 . 1.396(4) y C5 C7 . 1.485(4) y C7 O1 . 1.206(4) y C7 O2 . 1.313(4) y O3 N1 . 1.322(3) y N1 C8 . 1.350(4) y N1 C12 . 1.357(3) y C8 C9 . 1.358(5) y C9 C10 . 1.374(6) y C10 C11 . 1.382(6) y C11 C12 . 1.387(5) y C12 C13 . 1.492(5) y