#------------------------------------------------------------------------------ #$Date: 2016-02-14 04:40:26 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176432 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008208.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_2008208 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 H11 N.C7 H6 O2' _chemical_formula_sum 'C15 H17 N O2' _chemical_formula_weight 243.305 _chemical_melting_point 339 _chemical_name_systematic '2,4,6-Trymethylpyridine benzoic acid' _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 from_xtal_archive_file_using_CIFIO _cell_angle_alpha 90.00000 _cell_angle_beta 92.702(7) _cell_angle_gamma 90.00000 _cell_formula_units_Z 4 _cell_length_a 7.4875(6) _cell_length_b 14.4756(14) _cell_length_c 12.1879(12) _cell_measurement_reflns_used 66 _cell_measurement_temperature 150 _cell_measurement_theta_max 45 _cell_measurement_theta_min 2 _cell_volume 1319.5(2) _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 .054 _diffrn_reflns_av_sigmaI/netI .014 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2482 _diffrn_reflns_reduction_process perpendicular_monochr_Lp _diffrn_reflns_theta_max 64.47 _diffrn_reflns_theta_min 4.75 _diffrn_standards_decay_% 9 _diffrn_standards_interval_time 90 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.6489 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.37 _refine_diff_density_max .30 _refine_diff_density_min -.39 _refine_ls_abs_structure_details ' not applicable ' _refine_ls_extinction_coef 204(11) _refine_ls_extinction_method Zachariasen _refine_ls_goodness_of_fit_all .992 _refine_ls_goodness_of_fit_obs 1.00 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 168 _refine_ls_number_reflns 1723 _refine_ls_number_restraints 0 _refine_ls_R_factor_all .083 _refine_ls_R_factor_obs .068 _refine_ls_shift/esd_max .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 .103 _refine_ls_wR_factor_obs .091 _reflns_number_observed 1723 _reflns_number_total 2202 _reflns_observed_criterion refl_observed_if_I____>2.000_sigma(I___) _cod_data_source_file bm1262.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'None' changed to 'none' 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_values 1715 2011-07-08 13:25:40Z adriana 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_sg_symbol_Hall -P_2ybc _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2008208 _cod_database_fobs_code 2008208 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 N1 .0300(10) .038(2) .0330(10) -.0020(10) -.0060(10) .0010(10) C2 .030(2) .044(2) .032(2) -.0010(10) -.0050(10) .0000(10) C3 .035(2) .042(2) .034(2) -.0010(10) -.0030(10) .0050(10) C4 .040(2) .039(2) .040(2) .0010(10) -.0090(10) .004(2) C5 .037(2) .044(2) .035(2) .002(2) -.0070(10) .0000(10) C6 .031(2) .044(2) .031(2) -.0030(10) -.0080(10) .0020(10) C7 .045(2) .048(2) .042(2) .003(2) .002(2) -.004(2) C8 .072(3) .041(2) .058(3) .003(2) .001(2) .003(2) C9 .052(2) .048(2) .036(2) -.002(2) .002(2) .005(2) C10 .033(2) .039(2) .039(2) .0020(10) -.0060(10) -.002(2) C11 .030(2) .036(2) .035(2) .0030(10) -.0080(10) -.0030(10) C12 .036(2) .040(2) .038(2) .0030(10) -.0080(10) -.0020(10) C13 .044(2) .040(2) .043(2) .000(2) -.002(2) .005(2) C14 .034(2) .037(2) .057(2) .001(2) -.002(2) .002(2) C15 .034(2) .042(2) .053(2) -.001(2) -.010(2) -.011(2) C16 .039(2) .043(2) .038(2) .004(2) -.0100(10) -.002(2) O17 .054(2) .0390(10) .0450(10) -.0060(10) -.0180(10) -.0010(10) O18 .076(2) .046(2) .0380(10) -.0040(10) -.0170(10) .0060(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 .6489(4) .4047(2) .0938(2) .0340(10) Uani ? ? C2 .5842(4) .3525(3) .1755(3) .035(2) Uani ? ? C3 .5832(5) .2581(3) .1708(3) .038(2) Uani ? ? C4 .6507(5) .2121(3) .0811(3) .040(2) Uani ? ? C5 .7161(5) .2667(3) -.0024(3) .039(2) Uani ? ? C6 .7133(4) .3614(3) .0058(3) .036(2) Uani ? ? C7 .5177(5) .4049(3) .2715(3) .045(2) Uani ? ? C8 .6549(7) .1088(3) .0758(4) .057(2) Uani ? ? C9 .7822(5) .4223(3) -.0825(3) .045(2) Uani ? ? C10 .7835(5) .6221(3) .1766(3) .037(2) Uani ? ? C11 .8345(4) .7200(2) .1567(3) .034(2) Uani ? ? C12 .8023(5) .7617(3) .0541(3) .038(2) Uani ? ? C13 .8574(5) .8525(3) .0369(3) .043(2) Uani ? ? C14 .9416(5) .9018(3) .1209(3) .043(2) Uani ? ? C15 .9721(5) .8615(3) .2238(3) .044(2) Uani ? ? C16 .9200(5) .7708(3) .2407(3) .040(2) Uani ? ? O17 .6935(4) .5837(2) .0938(2) .0470(10) Uani ? ? O18 .8236(4) .5819(2) .2622(2) .054(2) Uani ? ? H3 .54370 .22205 .23307 .03734 Uiso ? ? H5 .75489 .23645 -.06710 .03843 Uiso ? ? H71 .41444 .43830 .24861 .04491 Uiso ? ? H72 .59226 .46078 .29356 .04491 Uiso ? ? H73 .48284 .36302 .33714 .04491 Uiso ? ? H81 .54546 .08706 .08836 .05735 Uiso ? ? H82 .69721 .07957 .00600 .05735 Uiso ? ? H83 .72300 .08236 .13212 .05735 Uiso ? ? H91 .89889 .45631 -.05228 .04539 Uiso ? ? H92 .70817 .47354 -.10347 .04539 Uiso ? ? H93 .80274 .38648 -.15235 .04539 Uiso ? ? H12 .74816 .72552 .00166 .03781 Uiso ? ? H13 .83783 .88505 -.03382 .04252 Uiso ? ? H14 .97733 .96618 .11303 .04260 Uiso ? ? H15 1.03261 .89483 .28428 .04298 Uiso ? ? H16 .93771 .73705 .30892 .03994 Uiso ? ? H17 .681(6) .509(3) .098(4) .030(10) 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 1 -1 2 -1 1 -2 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 N1 C2 118.5(3) yes N1 C2 C3 121.8(3) ? N1 C2 C7 115.8(3) ? C3 C2 C7 122.5(3) ? H3 C3 C2 120.1(3) ? H3 C3 C4 119.2(4) ? C2 C3 C4 120.5(3) ? C3 C4 C5 117.0(3) ? C3 C4 C8 121.3(4) ? C5 C4 C8 121.7(4) ? H5 C5 C6 121.4(4) ? H5 C5 C4 118.2(4) ? C6 C5 C4 120.3(3) ? N1 C6 C5 121.8(3) ? N1 C6 C9 116.4(3) ? C5 C6 C9 121.8(3) ? H71 C7 H73 107.0(4) ? H71 C7 H72 95.8(4) ? H71 C7 C2 109.1(3) ? H73 C7 H72 114.4(4) ? H73 C7 C2 114.1(3) ? H72 C7 C2 114.3(4) ? H81 C8 H83 101.9(5) ? H81 C8 H82 108.7(4) ? H81 C8 C4 108.8(4) ? H83 C8 H82 105.6(4) ? H83 C8 C4 113.3(4) ? H82 C8 C4 117.5(4) ? H92 C9 H93 106.3(3) ? H92 C9 H91 101.1(4) ? H92 C9 C6 115.7(4) ? H93 C9 H91 112.1(4) ? H93 C9 C6 111.9(3) ? H91 C9 C6 109.4(3) ? O18 C10 O17 123.6(3) yes O18 C10 C11 122.6(3) yes O17 C10 C11 113.8(3) yes C16 C11 C12 118.9(3) yes C16 C11 C10 119.6(3) ? C12 C11 C10 121.4(3) ? H12 C12 C13 124.3(4) ? H12 C12 C11 115.7(4) ? C13 C12 C11 120.1(3) ? H13 C13 C14 116.5(4) ? H13 C13 C12 123.2(4) ? C14 C13 C12 120.3(3) ? H14 C14 C13 122.7(4) ? H14 C14 C15 117.0(4) ? C13 C14 C15 120.2(3) ? H15 C15 C16 118.7(4) ? H15 C15 C14 121.7(4) ? C16 C15 C14 119.6(3) ? H16 C16 C15 125.2(4) ? H16 C16 C11 113.9(4) ? C15 C16 C11 120.9(3) ? H17 O17 C10 115(2) ? 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 C6 . . 1.351(4) yes N1 C2 . . 1.357(4) yes C2 C3 . . 1.369(5) ? C2 C7 . . 1.498(5) ? C3 H3 . . .978(4) ? C3 C4 . . 1.395(5) ? C4 C5 . . 1.395(5) ? C4 C8 . . 1.498(6) ? C5 H5 . . .959(4) ? C5 C6 . . 1.375(5) ? C6 C9 . . 1.500(5) ? C7 H71 . . .943(4) ? C7 H73 . . 1.047(4) ? C7 H72 . . 1.014(4) ? C8 H81 . . .898(5) ? C8 H83 . . .919(5) ? C8 H82 . . 1.014(5) ? C9 H92 . . .954(4) ? C9 H93 . . 1.015(4) ? C9 H91 . . 1.054(4) ? C10 O18 . . 1.219(5) yes C10 O17 . . 1.310(4) yes C10 C11 . . 1.491(5) yes C11 C16 . . 1.391(5) ? C11 C12 . . 1.398(5) ? C12 H12 . . .908(4) ? C12 C13 . . 1.396(5) ? C13 H13 . . .987(4) ? C13 C14 . . 1.376(5) ? C14 H14 . . .975(4) ? C14 C15 . . 1.392(6) ? C15 H15 . . .974(4) ? C15 C16 . . 1.388(5) ? C16 H16 . . .968(4) ? O17 H17 . . 1.09(5) ? 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 O17 H17 N1 . 1.09(5) 1.53(5) 2.613(4) 174(4) yes C7 H72 O18 . 1.01 2.51 3.443(5) 154 yes C13 H13 O18 4_564 0.99 2.53 3.478(5) 161 yes C14 H14 O18 2_755 0.98 2.67 3.418(5) 134 no 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 .2(5) ? C6 N1 C2 C7 179.1(3) ? C2 N1 C6 C5 -.6(5) ? C2 N1 C6 C9 179.6(3) ? N1 C2 C3 C4 .5(5) ? N1 C2 C3 H3 175.6(3) ? C7 C2 C3 C4 -178.3(3) ? C7 C2 C3 H3 -3.2(5) ? N1 C2 C7 H71 67.3(4) ? N1 C2 C7 H72 -38.7(5) ? N1 C2 C7 H73 -173.1(3) ? C3 C2 C7 H71 -113.8(4) ? C3 C2 C7 H72 140.2(4) ? C3 C2 C7 H73 5.8(5) ? C2 C3 C4 C5 -.7(5) ? C2 C3 C4 C8 178.5(4) ? H3 C3 C4 C5 -175.9(3) ? H3 C3 C4 C8 3.3(6) ? C3 C4 C5 C6 .3(5) ? C3 C4 C5 H5 -175.5(3) ? C8 C4 C5 C6 -178.9(4) ? C8 C4 C5 H5 5.3(6) ? C3 C4 C8 H81 51.7(6) ? C3 C4 C8 H82 175.6(4) ? C3 C4 C8 H83 -60.8(6) ? C5 C4 C8 H81 -129.1(4) ? C5 C4 C8 H82 -5.2(6) ? C5 C4 C8 H83 118.4(5) ? C4 C5 C6 N1 .3(5) ? C4 C5 C6 C9 -179.9(3) ? H5 C5 C6 N1 176.0(3) ? H5 C5 C6 C9 -4.3(6) ? N1 C6 C9 H91 67.7(4) ? N1 C6 C9 H92 -45.6(5) ? N1 C6 C9 H93 -167.5(3) ? C5 C6 C9 H91 -112.1(4) ? C5 C6 C9 H92 134.7(4) ? C5 C6 C9 H93 12.7(5) ? O17 C10 C11 C12 -5.9(5) yes O17 C10 C11 C16 175.7(3) ? O18 C10 C11 C12 173.7(4) yes O18 C10 C11 C16 -4.7(5) ? C11 C10 O17 H17 167(3) ? O18 C10 O17 H17 -13(3) ? C10 C11 C12 C13 -177.7(3) ? C10 C11 C12 H12 .5(5) ? C16 C11 C12 C13 .7(5) ? C16 C11 C12 H12 178.9(3) ? C10 C11 C16 C15 178.8(3) ? C10 C11 C16 H16 -1.4(5) ? C12 C11 C16 C15 .3(5) ? C12 C11 C16 H16 -179.8(3) ? C11 C12 C13 C14 -.8(6) ? C11 C12 C13 H13 -180.0(4) ? H12 C12 C13 C14 -178.8(4) ? H12 C12 C13 H13 2.0(7) ? C12 C13 C14 C15 -.2(6) ? C12 C13 C14 H14 -177.2(4) ? H13 C13 C14 C15 179.1(4) ? H13 C13 C14 H14 2.0(6) ? C13 C14 C15 C16 1.2(6) ? C13 C14 C15 H15 179.3(4) ? H14 C14 C15 C16 178.4(3) ? H14 C14 C15 H15 -3.5(6) ? C14 C15 C16 C11 -1.3(6) ? C14 C15 C16 H16 178.9(4) ? H15 C15 C16 C11 -179.4(3) ? H15 C15 C16 H16 .7(6) ?