#------------------------------------------------------------------------------ #$Date: 2016-02-14 04:40:26 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008209.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_2008209 loop_ _publ_author_name 'Foces-Foces, C.' 'Llamas-Saiz, A.L.' 'Lorente, P' 'Golubev, N.S.' 'Limbach, H.-H.' _publ_section_title ; Three 2,4,6-trimethylpyridine--benzoic acid complexes at 150K ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 377 _journal_page_last 381 _journal_paper_doi 10.1107/S0108270198013766 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C8 H12 N +C7 H4 N O4 -' _chemical_formula_sum 'C15 H16 N2 O4' _chemical_formula_weight 288.302 _chemical_melting_point 423 _chemical_name_systematic '2,4,6-Trymethylpyridinium ortho-nitro-benzoate' _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method from_xtal_archive_file_using_CIFIO _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 90.00000 _cell_formula_units_Z 8 _cell_length_a 25.732(3) _cell_length_b 7.8359(4) _cell_length_c 13.9540(10) _cell_measurement_reflns_used 85 _cell_measurement_temperature 150 _cell_measurement_theta_max 45 _cell_measurement_theta_min 2 _cell_volume 2813.6(4) _computing_cell_refinement 'LSUCRE (Appleman, 1984)' _computing_data_collection 'Philips PW1100 (Hornstra & Vossers, 1973)' _computing_data_reduction 'xtal_DIFDAT_SORTRF_ADDREF (Hall et al., 1992)' _computing_molecular_graphics xtal_ORTEP _computing_publication_material xtal_BONDLA_CIFIO _computing_structure_refinement 'xtal CRYLSQ' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 150 _diffrn_measurement_device 'Philips PW1100 diffractometer' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'scaled tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .000 _diffrn_reflns_av_sigmaI/netI .011 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2396 _diffrn_reflns_reduction_process perpendicular_monochr_Lp _diffrn_reflns_theta_max 65.07 _diffrn_reflns_theta_min 3.44 _diffrn_standards_decay_% 2 _diffrn_standards_interval_time 90 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.8305 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.33 _refine_diff_density_max .24 _refine_diff_density_min -.36 _refine_ls_abs_structure_details 'not applicable' _refine_ls_extinction_coef '9.6(3) x 10^2^' _refine_ls_extinction_method Zachariasen _refine_ls_goodness_of_fit_all .944 _refine_ls_goodness_of_fit_obs .947 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 195 _refine_ls_number_reflns 1977 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .068 _refine_ls_R_factor_obs .059 _refine_ls_shift/esd_max .025 _refine_ls_shift/esd_mean .009 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = k{(A + BFo)^2^[C + D(sin\q)/\l]}^-1^' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .077 _refine_ls_wR_factor_obs .07 _reflns_number_observed 1977 _reflns_number_total 2396 _reflns_observed_criterion refl_observed_if_I____>2.000_sigma(I___) _cod_data_source_file bm1262.cif _cod_data_source_block II _cod_depositor_comments ; 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 'w = k{(A + BFo)^2^[C + D(sin\q)/\l]}^-1^' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = k{(A + BFo)^2^[C + D(sin\q)/\l]}^-1^'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 2813.6(5) _cod_original_sg_symbol_Hall -P_2ac_2ab _cod_database_code 2008209 _cod_database_fobs_code 2008209 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,+y,1/2-z 1/2-x,1/2+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 N1 .0240(10) .0360(10) .0380(10) .0020(10) -.0004(9) .0000(10) C2 .0280(10) .0370(10) .0360(10) .0000(10) -.0020(10) -.0010(10) C3 .0290(10) .0370(10) .043(2) .0020(10) -.0030(10) -.0010(10) C4 .0250(10) .047(2) .0400(10) .0010(10) -.0030(10) -.0030(10) C5 .0270(10) .041(2) .044(2) -.0040(10) -.0010(10) -.0020(10) C6 .0300(10) .0410(10) .0370(10) -.0030(10) -.0010(10) -.0020(10) C7 .0280(10) .041(2) .051(2) -.0030(10) .0020(10) .0020(10) C8 .0260(10) .056(2) .061(2) .0050(10) -.0020(10) -.001(2) C9 .0380(10) .037(2) .060(2) -.0010(10) .0010(10) .0020(10) C10 .0250(10) .041(2) .0410(10) .0000(10) .0010(10) .0030(10) C11 .0260(10) .0390(10) .0340(10) .0010(10) .0000(10) .0000(10) C12 .0300(10) .042(2) .0400(10) -.0040(10) -.0010(10) .0010(10) C13 .046(2) .040(2) .039(2) -.0020(10) -.0040(10) .0010(10) C14 .040(2) .041(2) .046(2) .0100(10) .0020(10) -.0010(10) C15 .0270(10) .048(2) .046(2) .0040(10) .0030(10) -.0010(10) C16 .0270(10) .0370(10) .0380(10) -.0020(10) .0000(10) .0000(10) O17 .0310(10) .0530(10) .075(2) .0104(9) .0170(10) .0130(10) O18 .0340(10) .0390(10) .081(2) .0056(9) .0110(10) .0090(10) N19 .0240(10) .0460(10) .0460(10) .0010(10) .0000(10) .0010(10) O20 .0430(10) .0580(10) .0590(10) -.0120(10) .0070(10) .0080(10) O21 .0530(10) .0490(10) .0600(10) -.0070(10) -.0050(10) -.0090(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 _atom_site_calc_flag _atom_site_calc_attached_atom N1 .56563(8) .2536(3) .3404(2) .0320(10) Uani ? ? C2 .57310(10) .0842(3) .3487(2) .0340(10) Uani ? ? C3 .62260(10) .0197(4) .3368(2) .0360(10) Uani ? ? C4 .66410(10) .1271(4) .3168(2) .0380(10) Uani ? ? C5 .65420(10) .3002(4) .3077(2) .0370(10) Uani ? ? C6 .60460(10) .3638(4) .3205(2) .0360(10) Uani ? ? C7 .52690(10) -.0239(4) .3718(2) .040(2) Uani ? ? C8 .71820(10) .0572(4) .3069(2) .048(2) Uani ? ? C9 .59180(10) .5488(4) .3131(2) .045(2) Uani ? ? C10 .43670(10) .3739(4) .4065(2) .0360(10) Uani ? ? C11 .39820(10) .5186(4) .4171(2) .0330(10) Uani ? ? C12 .41490(10) .6879(4) .4140(2) .0370(10) Uani ? ? C13 .38080(10) .8226(4) .4267(2) .042(2) Uani ? ? C14 .32870(10) .7902(4) .4435(2) .042(2) Uani ? ? C15 .31070(10) .6250(4) .4480(2) .040(2) Uani ? ? C16 .34550(10) .4931(4) .4349(2) .0340(10) Uani ? ? O17 .47778(7) .4115(3) .3628(2) .0530(10) Uani ? ? O18 .42497(8) .2342(3) .4418(2) .0510(10) Uani ? ? N19 .32380(8) .3189(3) .4376(2) .0390(10) Uani ? ? O20 .30812(8) .2654(3) .5147(2) .0530(10) Uani ? ? O21 .31958(9) .2408(3) .3621(2) .0540(10) Uani ? ? H1 .5320(10) .301(4) .350(3) .021(8) Uiso ? ? H3 .62857 -.10144 .34526 .03629 Uiso ? ? H5 .68211 .37995 .29356 .03699 Uiso ? ? H71 .53712 -.10418 .42353 .04040 Uiso ? ? H72 .51841 -.08733 .31144 .04040 Uiso ? ? H73 .49572 .04757 .39051 .04040 Uiso ? ? H81 .71880 -.07608 .30290 .04794 Uiso ? ? H82 .73700 .10417 .25398 .04794 Uiso ? ? H83 .73735 .08114 .36535 .04794 Uiso ? ? H91 .61870 .61333 .29079 .04575 Uiso ? ? H92 .58328 .59811 .37486 .04575 Uiso ? ? H93 .56431 .57268 .27177 .04575 Uiso ? ? H12 .45070 .70531 .40379 .03716 Uiso ? ? H13 .39437 .94471 .42728 .04164 Uiso ? ? H14 .30422 .88380 .45403 .04223 Uiso ? ? H15 .27439 .60098 .45956 .04032 Uiso ? ? loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 International_Tables_for_Crystallography_(1974) H 0 0 International_Tables_for_Crystallography_(1974) N .029 .018 International_Tables_for_Crystallography_(1974) O .047 .032 International_Tables_for_Crystallography_(1974) loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -3 -1 3 3 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 H1 N1 C2 120(2) ? H1 N1 C6 117(2) ? C2 N1 C6 122.8(2) yes N1 C2 C3 118.8(2) ? N1 C2 C7 117.7(2) ? C3 C2 C7 123.5(2) ? H3 C3 C2 119.3(3) ? H3 C3 C4 119.8(3) ? C2 C3 C4 120.8(3) ? C5 C4 C3 118.1(2) ? C5 C4 C8 121.3(3) ? C3 C4 C8 120.7(3) ? H5 C5 C6 118.5(3) ? H5 C5 C4 120.8(3) ? C6 C5 C4 120.7(3) ? N1 C6 C5 118.8(3) ? N1 C6 C9 118.1(2) ? C5 C6 C9 123.1(3) ? H71 C7 H72 110.8(3) ? H71 C7 H73 111.9(3) ? H71 C7 C2 107.8(2) ? H72 C7 H73 108.5(3) ? H72 C7 C2 105.9(3) ? H73 C7 C2 111.8(3) ? H82 C8 H83 108.4(3) ? H82 C8 H81 109.6(3) ? H82 C8 C4 113.5(3) ? H83 C8 H81 103.3(3) ? H83 C8 C4 108.8(3) ? H81 C8 C4 112.6(3) ? H92 C9 H91 104.9(3) ? H92 C9 H93 107.6(3) ? H92 C9 C6 112.3(3) ? H91 C9 H93 104.6(3) ? H91 C9 C6 113.2(3) ? H93 C9 C6 114.0(3) ? O18 C10 O17 127.3(3) yes O18 C10 C11 117.7(2) yes O17 C10 C11 115.0(3) yes C16 C11 C12 116.2(2) yes C16 C11 C10 123.2(2) ? C12 C11 C10 120.6(2) ? H12 C12 C13 121.9(3) ? H12 C12 C11 116.3(3) ? C13 C12 C11 121.8(2) ? H13 C13 C12 120.0(3) ? H13 C13 C14 120.2(3) ? C12 C13 C14 119.7(3) ? H14 C14 C15 118.9(3) ? H14 C14 C13 120.7(3) ? C15 C14 C13 120.4(3) ? H15 C15 C14 121.1(3) ? H15 C15 C16 120.3(3) ? C14 C15 C16 118.7(3) ? C15 C16 C11 123.2(3) yes C15 C16 N19 116.3(2) yes C11 C16 N19 120.4(2) yes O21 N19 O20 123.9(3) yes O21 N19 C16 118.4(2) yes O20 N19 C16 117.6(2) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 H1 . . .95(4) ? N1 C2 . . 1.346(4) yes N1 C6 . . 1.352(4) yes C2 C3 . . 1.382(4) ? C2 C7 . . 1.494(4) ? C3 H3 . . .969(3) ? C3 C4 . . 1.388(4) ? C4 C5 . . 1.386(4) ? C4 C8 . . 1.501(4) ? C5 H5 . . .971(3) ? C5 C6 . . 1.382(4) ? C6 C9 . . 1.490(4) ? C7 H71 . . .993(3) ? C7 H72 . . 1.002(3) ? C7 H73 . . 1.013(3) ? C8 H82 . . .957(3) ? C8 H83 . . .972(3) ? C8 H81 . . 1.046(3) ? C9 H92 . . .966(3) ? C9 H91 . . .913(3) ? C9 H93 . . .932(3) ? C10 O18 . . 1.238(4) yes C10 O17 . . 1.256(3) yes C10 C11 . . 1.512(4) yes C11 C16 . . 1.393(4) ? C11 C12 . . 1.395(4) ? C12 H12 . . .943(3) ? C12 C13 . . 1.384(4) ? C13 H13 . . 1.019(3) ? C13 C14 . . 1.385(4) ? C14 H14 . . .977(3) ? C14 C15 . . 1.376(4) ? C15 H15 . . .966(3) ? C15 C16 . . 1.380(4) ? C16 N19 . . 1.475(4) yes N19 O21 . . 1.223(4) yes N19 O20 . . 1.224(3) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O17 . .94(4) 1.65(4) 2.596(3) 171(3) yes C9 H93 O17 . .93 2.86 3.200(4) 103 no C7 H73 O18 . 1.01 2.44 3.453(4) 176 yes C13 H13 O18 1_565 1.02 2.41 3.426(4) 176 yes C7 H72 O17 4_645 1.00 2.43 3.314(4) 146 yes C8 H83 O20 3_556 0.97 2.75 3.672(4) 159 yes C9 H91 O21 4_655 0.91 2.84 3.668(4) 151 yes C8 H81 O21 4_645 1.05 2.89 3.557(4) 122 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C6 N1 C2 C3 .3(4) ? C6 N1 C2 C7 179.5(3) ? H1 N1 C2 C3 -178(2) ? H1 N1 C2 C7 1(2) ? C2 N1 C6 C5 .2(4) ? C2 N1 C6 C9 -179.9(3) ? H1 N1 C6 C5 178(2) ? H1 N1 C6 C9 -2(2) ? N1 C2 C3 C4 .1(4) ? N1 C2 C3 H3 177.5(3) ? C7 C2 C3 C4 -179.0(3) ? C7 C2 C3 H3 -1.7(4) ? N1 C2 C7 H71 -133.7(3) ? N1 C2 C7 H72 107.7(3) ? N1 C2 C7 H73 -10.4(4) ? C3 C2 C7 H71 45.4(4) ? C3 C2 C7 H72 -73.2(3) ? C3 C2 C7 H73 168.8(3) ? C2 C3 C4 C5 -1.0(4) ? C2 C3 C4 C8 178.1(3) ? H3 C3 C4 C5 -178.3(3) ? H3 C3 C4 C8 .8(4) ? C3 C4 C5 C6 1.5(4) ? C3 C4 C5 H5 -179.8(3) ? C8 C4 C5 C6 -177.6(3) ? C8 C4 C5 H5 1.1(5) ? C3 C4 C8 H81 11.5(4) ? C3 C4 C8 H82 136.8(3) ? C3 C4 C8 H83 -102.4(3) ? C5 C4 C8 H81 -169.5(3) ? C5 C4 C8 H82 -44.2(4) ? C5 C4 C8 H83 76.6(4) ? C4 C5 C6 N1 -1.1(4) ? C4 C5 C6 C9 179.0(3) ? H5 C5 C6 N1 -179.8(3) ? H5 C5 C6 C9 .3(5) ? N1 C6 C9 H91 -171.3(3) ? N1 C6 C9 H92 70.4(4) ? N1 C6 C9 H93 -51.8(4) ? C5 C6 C9 H91 8.6(5) ? C5 C6 C9 H92 -109.6(3) ? C5 C6 C9 H93 128.1(3) ? O17 C10 C11 C12 -24.1(4) yes O17 C10 C11 C16 159.2(3) ? O18 C10 C11 C12 155.2(3) yes O18 C10 C11 C16 -21.5(4) ? C10 C11 C12 C13 -177.7(3) ? C10 C11 C12 H12 1.2(4) ? C16 C11 C12 C13 -.8(4) ? C16 C11 C12 H12 178.2(3) ? C10 C11 C16 C15 177.6(3) ? C10 C11 C16 N19 -4.4(4) ? C12 C11 C16 C15 .7(4) ? C12 C11 C16 N19 178.7(2) ? C11 C12 C13 C14 .3(4) ? C11 C12 C13 H13 177.1(3) ? H12 C12 C13 C14 -178.6(3) ? H12 C12 C13 H13 -1.8(5) ? C12 C13 C14 C15 .3(5) ? C12 C13 C14 H14 178.7(3) ? H13 C13 C14 C15 -176.5(3) ? H13 C13 C14 H14 1.9(5) ? C13 C14 C15 C16 -.4(5) ? C13 C14 C15 H15 -179.9(3) ? H14 C14 C15 C16 -178.8(3) ? H14 C14 C15 H15 1.7(5) ? C14 C15 C16 C11 -.2(4) ? C14 C15 C16 N19 -178.2(3) ? H15 C15 C16 C11 179.3(3) ? H15 C15 C16 N19 1.3(4) ? C11 C16 N19 O20 112.5(3) ? C11 C16 N19 O21 -71.9(3) yes C15 C16 N19 O20 -69.4(3) yes C15 C16 N19 O21 106.2(3) ?