#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:08:28 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/54/2005486.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_2005486 loop_ _publ_author_name 'Bell, W.' 'Coupar, P. I.' 'Ferguson, G.' 'Glidewell, C.' _publ_section_title ; Multiple Hydrogen Bonds in Pyridine-2,6-dimethanol and Benzene-1,3,5-trimethanol ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2520 _journal_page_last 2524 _journal_paper_doi 10.1107/S0108270196006014 _journal_volume 52 _journal_year 1996 _chemical_formula_iupac 'C7 H9 N1 O2' _chemical_formula_moiety 'C7 H9 N1 O2' _chemical_formula_sum 'C7 H9 N O2' _chemical_formula_weight 139.15 _chemical_name_systematic ; Pyridine-2,5-dimethanol ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 80.41(2) _cell_angle_beta 80.27(2) _cell_angle_gamma 67.121(10) _cell_formula_units_Z 2 _cell_length_a 6.8730(10) _cell_length_b 7.2268(14) _cell_length_c 7.471(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294(1) _cell_measurement_theta_max 22.32 _cell_measurement_theta_min 11.74 _cell_volume 334.88(12) _computing_cell_refinement 'SET4 and CELDIM in CAD-4-PC Software' _computing_data_collection 'CAD-4-PC Software (Enraf-Nonius, 1992)' _computing_data_reduction 'DATRD2 in NRCVAX94 (Gabe, Le Page, Charland, Lee & White, 1989)' _computing_molecular_graphics 'NRCVAX94, PLATON and PLUTON (Spek, 1995b)' _computing_publication_material 'NRCVAX94, SHELXL93 and WordPerfect (macro PREPCIF)' _computing_structure_refinement 'NRCVAX94 and SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 294.0(10) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.0 _diffrn_reflns_av_sigmaI/netI 0.0547 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 1945 _diffrn_reflns_theta_max 30 _diffrn_reflns_theta_min 2 _diffrn_standards_decay_% none _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 148 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.249 _refine_diff_density_min -0.157 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 0.969 _refine_ls_goodness_of_fit_obs 1.203 _refine_ls_hydrogen_treatment 'H atoms riding (SHELXL93 defaults; C---H 0.93--0.97 and O---H 0.82\%A)' _refine_ls_matrix_type full _refine_ls_number_parameters 93 _refine_ls_number_reflns 1945 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.969 _refine_ls_restrained_S_obs 1.203 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_obs 0.0483 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ; calc w = 1/[\s^2^(F~o~^2^) + (0.0644P)^2^] where P = (F~o~^2^ + 2F~c~^2^)/3 ; _refine_ls_wR_factor_all 0.1328 _refine_ls_wR_factor_obs 0.1182 _reflns_number_observed 1039 _reflns_number_total 1945 _reflns_observed_criterion >2\s(I) _cod_data_source_file cf1110.cif _cod_data_source_block I _cod_original_cell_volume 334.87(11) _cod_database_code 2005486 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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 O2 0.0346(7) 0.0580(8) 0.0520(8) -0.0142(6) 0.0036(6) -0.0159(6) O6 0.0319(7) 0.0488(8) 0.0497(8) -0.0067(5) -0.0135(5) -0.0115(6) N1 0.0296(7) 0.0333(7) 0.0335(7) -0.0117(6) -0.0074(5) -0.0028(5) C2 0.0306(8) 0.0283(8) 0.0348(9) -0.0103(6) -0.0070(7) -0.0035(6) C3 0.0267(8) 0.0369(9) 0.0452(10) -0.0082(7) -0.0096(7) -0.0049(7) C4 0.0380(9) 0.0448(10) 0.0391(9) -0.0138(8) -0.0172(7) -0.0002(7) C5 0.0422(10) 0.0422(10) 0.0301(8) -0.0151(8) -0.0071(7) -0.0029(7) C6 0.0321(9) 0.0305(8) 0.0367(9) -0.0119(7) -0.0052(7) -0.0030(7) C21 0.0315(9) 0.0428(10) 0.0370(9) -0.0127(7) -0.0046(7) -0.0055(7) C61 0.0324(9) 0.0514(11) 0.0416(10) -0.0159(8) -0.0032(7) -0.0062(8) loop_ _atom_site_label _atom_site_occupancy _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_type_symbol O2 1 -0.3346(2) 0.3650(2) 0.2479(2) 0.0490(4) Uani d . O O6 1 0.5593(2) -0.1192(2) -0.2209(2) 0.0442(4) Uani d . O N1 1 0.1688(2) 0.1968(2) -0.0465(2) 0.0317(3) Uani d . N C2 1 -0.0421(2) 0.2715(2) -0.0013(2) 0.0310(4) Uani d . C C3 1 -0.1843(3) 0.3383(2) -0.1306(2) 0.0367(4) Uani d . C C4 1 -0.1060(3) 0.3254(3) -0.3126(2) 0.0401(4) Uani d . C C5 1 0.1113(3) 0.2469(3) -0.3608(2) 0.0382(4) Uani d . C C6 1 0.2450(2) 0.1841(2) -0.2243(2) 0.0329(4) Uani d . C C21 1 -0.1124(3) 0.2776(3) 0.2013(2) 0.0372(4) Uani d . C C61 1 0.4828(3) 0.0940(3) -0.2669(2) 0.0417(4) Uani d . C H2 1 -0.3885 0.2836 0.2409 0.073 Uiso calc R H H6 1 0.6430 -0.1514 -0.1447 0.066 Uiso calc R H H3 1 -0.3300 0.3909 -0.0953 0.044 Uiso calc R H H4 1 -0.1984 0.3691 -0.4019 0.048 Uiso calc R H H5 1 0.1671 0.2363 -0.4828 0.046 Uiso calc R H H21A 1 -0.0613 0.1406 0.2617 0.045 Uiso calc R H H21B 1 -0.0460 0.3531 0.2482 0.045 Uiso calc R H H61A 1 0.5220 0.1252 -0.3960 0.050 Uiso calc R H H61B 1 0.5479 0.1529 -0.1984 0.050 Uiso calc R H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 1 3 -2 1 1 2 -1 -1 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 C2 N1 C6 118.63(13) y N1 C2 C3 122.47(15) y N1 C2 C21 114.81(13) ? C3 C2 C21 122.73(15) ? C2 C3 C4 118.8(2) y C3 C4 C5 119.27(15) y C4 C5 C6 118.9(2) y N1 C6 C5 121.9(2) y N1 C6 C61 116.42(14) ? C5 C6 C61 121.7(2) ? O2 C21 C2 114.66(14) y O6 C61 C6 110.56(13) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O2 C21 1.413(2) y O6 C61 1.423(2) y N1 C2 1.339(2) y N1 C6 1.347(2) y C2 C3 1.385(2) y C2 C21 1.512(2) y C3 C4 1.380(2) y C4 C5 1.382(2) y C5 C6 1.389(2) y C6 C61 1.504(2) y 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 -0.8(2) ? C6 N1 C2 C21 179.32(13) ? N1 C2 C3 C4 0.7(2) ? C21 C2 C3 C4 -179.42(15) ? C2 C3 C4 C5 -0.1(2) ? C3 C4 C5 C6 -0.4(2) ? C2 N1 C6 C5 0.3(2) ? C2 N1 C6 C61 -178.45(14) ? C4 C5 C6 N1 0.3(2) ? C4 C5 C6 C61 178.97(15) ? N1 C2 C21 O2 177.22(14) y C3 C2 C21 O2 -2.6(2) ? N1 C6 C61 O6 74.7(2) y C5 C6 C61 O6 -104.0(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 64119