#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2008656.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_2008656 loop_ _publ_author_name 'Foces-Foces, C.' 'Cabildo, P.' 'Claramunt, R. M.' 'Elguero, J.' _publ_section_title ; 4-(1H-1,2,4-Triazol-1-yl)phenol ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1160 _journal_page_last 1163 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C8 H7 N3 O' _chemical_formula_sum 'C8 H7 N3 O' _chemical_formula_weight 161.163 _chemical_melting_point 528 _chemical_name_systematic 4-(1H-1,2,4-triazol-1-yl)phenol _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' _audit_creation_method from_xtal_archive_file_using_CIFIO _cell_angle_alpha 90.00000 _cell_angle_beta 94.960(10) _cell_angle_gamma 90.00000 _cell_formula_units_Z 4 _cell_length_a 18.409(2) _cell_length_b 7.2898(6) _cell_length_c 5.6649(4) _cell_measurement_reflns_used 44 _cell_measurement_temperature 293 _cell_measurement_theta_max 45 _cell_measurement_theta_min 2 _cell_volume 757.37(12) _computing_cell_refinement 'LSUCRE (Appleman, 1994)' _computing_data_collection 'CRYSOM (Seifert, 1996)' _computing_data_reduction 'xtal3.2 (Hall et al., 1992)' _computing_molecular_graphics xtal3.2 _computing_publication_material xtal3.2 _computing_structure_refinement xtal3.2 _computing_structure_solution 'SIR97 (Altomare et al., 1997)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Seifert XRD 3000-S' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source xray_tube _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.01 _diffrn_reflns_av_sigmaI/netI 0.018 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 1657 _diffrn_reflns_reduction_process equatorial_monochr_Lp _diffrn_reflns_theta_max 67.47 _diffrn_reflns_theta_min 4.82 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 100 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.31 _refine_diff_density_min -0.29 _refine_ls_abs_structure_details none _refine_ls_extinction_coef '5.7(3) \\times 10^2^' _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_goodness_of_fit_all 0.903 _refine_ls_goodness_of_fit_obs 0.895 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 138 _refine_ls_number_reflns 1104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.061 _refine_ls_R_factor_obs 0.051 _refine_ls_shift/esd_max 0.006 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme 'w = k/[(A+B Fo)^2^(C+D(sin\q)/\l)]' _refine_ls_wR_factor_all 0.044 _refine_ls_wR_factor_obs 0.039 _reflns_number_observed 1104 _reflns_number_total 1324 _reflns_observed_criterion I>\s(I) _[local]_cod_data_source_file bm1323.cif _[local]_cod_data_source_block tzphoh _[local]_cod_cif_authors_sg_H-M P_1_21/n_1 _[local]_cod_cif_authors_sg_Hall -P_2yn _cod_original_cell_volume 757.40(10) _cod_database_code 2008656 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+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 .0313(7) .0475(9) .0395(9) -.0002(7) .0061(7) -.0011(7) N2 .0402(9) .0640(10) .0460(10) -.0019(8) .0123(7) .0020(8) C3 .0380(10) .0620(10) .0620(10) -.0008(9) .0130(10) .0020(10) N4 .0335(8) .0660(10) .0610(10) -.0041(8) .0041(8) -.0073(9) C5 .0350(10) .0660(10) .0470(10) -.0035(9) .0036(9) -.0080(10) C6 .0327(9) .0380(10) .0390(10) .0020(7) .0051(7) -.0022(8) C7 .0380(10) .0430(10) .0370(10) .0008(8) .0059(8) .0009(8) C8 .0374(9) .0450(10) .0350(10) .0021(8) .0015(8) -.0021(8) C9 .0327(9) .0360(10) .0430(10) .0003(7) .0056(8) -.0062(8) C10 .0390(10) .0440(10) .0400(10) -.0003(8) .0089(8) .0057(9) C11 .0400(10) .0470(10) .0400(10) .0036(9) .0021(8) .0068(9) O12 .0303(7) .0616(9) .0536(9) -.0017(6) .0066(6) .0027(7) 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 N1 .43675(7) .2069(2) .5584(3) .0393(8) Uani N2 .47453(8) .2201(3) .3621(3) .0500(10) Uani C3 .53950(10) .2711(3) .4528(4) .0530(10) Uani N4 .54636(8) .2907(3) .6906(3) .0530(10) Uani C5 .48070(10) .2496(3) .7494(4) .0500(10) Uani C6 .36086(9) .1616(2) .5425(3) .0365(9) Uani C7 .31620(9) .2142(3) .3463(3) .0390(10) Uani C8 .24220(10) .1807(3) .3377(3) .0390(10) Uani C9 .21293(9) .0951(2) .5266(3) .0372(9) Uani C10 .25840(10) .0399(3) .7206(3) .0410(10) Uani C11 .33250(10) .0719(3) .7296(3) .0420(10) Uani O12 .14021(7) .0613(2) .5320(3) .0483(8) Uani H3 .5770(10) .301(3) .351(4) .031(6) Uiso H5 .4640(10) .253(3) .907(4) .028(6) Uiso H7 .3380(10) .273(3) .216(4) .025(6) Uiso H8 .2100(10) .217(3) .201(4) .018(5) Uiso H10 .2380(10) -.019(3) .852(4) .023(5) Uiso H11 .3650(10) .031(3) .867(4) .016(5) Uiso H12 .112(2) .119(4) .391(5) .057(8) Uiso loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C .017 .009 'Int. Tables (1974, Vol IV)' H 0 0 'Int. Tables (1974, Vol IV)' N .029 .018 'Int. Tables (1974, Vol IV)' O .047 .032 'Int. Tables (1974, Vol IV)' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 6 0 0 -6 0 0 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 N2 N1 C5 109.20(10) yes N2 N1 C6 121.90(10) yes C5 N1 C6 128.8(2) yes N1 N2 C3 102.3(2) yes N2 C3 N4 115.1(2) yes N2 C3 H3 121.0(10) ? N4 C3 H3 124.0(10) ? C3 N4 C5 102.7(2) yes N1 C5 N4 110.8(2) yes N1 C5 H5 123.0(10) ? N4 C5 H5 127.0(10) ? N1 C6 C7 119.8(2) ? N1 C6 C11 119.4(2) ? C7 C6 C11 120.7(2) yes C6 C7 C8 119.8(2) ? C6 C7 H7 119.0(10) ? C8 C7 H7 121.0(10) ? C7 C8 C9 120.0(2) ? C7 C8 H8 121.0(10) ? C9 C8 H8 119.0(10) ? C8 C9 C10 119.7(2) yes C8 C9 O12 123.0(2) ? C10 C9 O12 117.2(2) ? C9 C10 C11 120.6(2) ? C9 C10 H10 120.0(10) ? C11 C10 H10 120.0(10) ? C6 C11 C10 119.2(2) ? C6 C11 H11 120.0(10) ? C10 C11 H11 120.0(10) ? C9 O12 H12 110(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 N2 1.365(2) yes N1 C5 1.331(2) yes N1 C6 1.431(2) yes N2 C3 1.314(2) yes C3 N4 1.350(3) yes C3 H3 0.97(2) ? N4 C5 1.316(3) yes C5 H5 0.96(2) ? C6 C7 1.379(2) ? C6 C11 1.385(3) ? C7 C8 1.382(3) ? C7 H7 0.97(2) ? C8 C9 1.387(3) ? C8 H8 0.97(2) ? C9 C10 1.382(2) ? C9 O12 1.364(2) yes C10 C11 1.381(3) ? C10 H10 0.96(2) ? C11 H11 0.98(2) ? O12 H12 1.00(3) ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 N4 H12 1.72(3) 4 C9 H12 1.95(3) . N2 H3 1.99(2) . N1 H5 2.02(2) . C6 H7 2.03(2) . C9 H10 2.04(2) . C11 H10 2.04(2) . N4 H5 2.04(2) . C9 H8 2.05(2) . C7 H8 2.05(2) . N4 H3 2.06(2) . C10 H11 2.06(2) . C8 H7 2.06(2) . C6 H11 2.06(2) . C3 C5 2.082(3) . N1 C3 2.085(3) . N1 N4 2.178(2) . N2 C5 2.197(3) . N2 N4 2.247(2) . H8 H12 2.29(4) . C10 O12 2.344(2) . H10 H11 2.36(3) . H7 H8 2.38(3) . C6 C10 2.386(3) . C6 C8 2.388(2) . C8 C10 2.395(3) . C7 C9 2.397(3) . C9 C11 2.400(2) . C7 C11 2.402(3) . C8 O12 2.418(2) . N1 C7 2.431(2) . N1 C11 2.432(2) . H5 H11 2.44(3) . O12 H3 2.44(2) 4_455 N2 C6 2.444(2) . C8 H12 2.48(3) . C5 C6 2.491(3) . O12 H10 2.51(2) . O12 H7 2.58(2) 2_545 N2 H5 2.58(2) 1_554 N1 H7 2.59(2) . N2 H7 2.61(2) . N1 H11 2.62(2) . O12 H8 2.62(2) . C5 H12 2.66(3) 4 H8 H10 2.70(3) 1_554 N4 O12 2.704(2) 4 H7 H11 2.73(3) 1_554 C6 C9 2.760(2) . C7 C10 2.763(3) . C6 H5 2.76(2) . H7 H12 2.77(4) 2 C8 C11 2.772(3) . C5 H11 2.79(2) . H3 H12 2.79(4) 4_554 C8 H10 2.81(2) 2_556 C7 H10 2.83(2) 2_556 C3 H12 2.83(3) 4 C9 H7 2.84(2) 2_545 C11 H5 2.87(2) . H5 H12 2.89(4) 4 N2 C7 2.909(2) . H3 H11 2.96(3) 3_656 O12 H5 3.00(2) 2_546 N4 H8 3.01(2) 4 C5 C11 3.013(3) . H3 H8 3.01(3) 4 N1 H3 3.02(2) . C9 H10 3.02(2) 2_556 C5 H3 3.02(2) . C3 H5 3.03(2) . H5 H7 3.04(3) 1_556 C6 H10 3.04(2) 2_556 C8 H10 3.11(2) 1_554 N2 H5 3.12(2) . C11 H7 3.12(2) 1_556 H3 H12 3.13(4) 4 H3 H5 3.14(3) 1_554 C10 H12 3.19(3) . C10 H8 3.21(2) 1_556 C7 H11 3.22(2) 1_554 C11 H3 3.24(2) 3_656 C10 H10 3.24(2) 2_556 H8 H10 3.26(3) 2_556 C6 H10 3.26(2) . C8 H10 3.26(2) . C11 H7 3.27(2) . C10 H8 3.27(2) . C6 H8 3.27(2) . C11 H10 3.27(2) 2_556 H5 H12 3.27(4) 2_556 C3 H5 3.28(2) 1_554 C9 H7 3.28(2) . C9 H11 3.29(2) . H7 H10 3.29(3) 2_556 C7 H11 3.29(2) . C9 H3 3.31(2) 4_455 H11 H12 3.31(4) 2_546 C8 H7 3.32(2) 2_545 C3 H8 3.33(2) 4 H3 H10 3.35(3) 4_554 C3 O12 3.373(3) 4_554 H7 H10 3.40(3) 1_554 H7 H8 3.40(3) 2 C9 H8 3.40(2) 2_545 C3 H11 3.44(2) 3_656 C10 H8 3.44(2) 2_545 C7 O12 3.455(2) 2 C3 C6 3.464(3) . C5 H3 3.47(2) 3_666 O12 H11 3.48(2) 2_556 C7 H10 3.48(2) 1_554 H10 H12 3.48(3) . C5 O12 3.483(3) 2_556 N2 C5 3.489(3) 1_554 C10 H7 3.49(2) 1_556 C7 C9 3.503(3) 2 C8 H8 3.50(2) 2_545 C5 O12 3.503(2) 4 C10 H7 3.51(2) 2_545 N1 C3 3.513(3) 3_656 O12 H5 3.53(2) 4_454 N1 N2 3.526(2) 3_656 C7 H12 3.54(3) 2 C9 H11 3.56(2) 2_556 N2 H12 3.56(3) 2 N4 C9 3.565(2) 4 C9 C10 3.565(3) 2_556 N4 C6 3.572(2) . N2 H11 3.59(2) 1_554 N2 C5 3.590(3) 3_656 C11 H8 3.59(2) 2_545 C6 H3 3.60(2) 3_656 N2 N4 3.596(3) 3_666 H3 H5 3.62(3) 3_666 C11 O12 3.620(2) . C8 C10 3.622(3) 2_556 C3 N4 3.625(3) 3_666 N1 H3 3.63(2) 3_666 N4 C8 3.635(2) 4 C5 C7 3.640(3) . N2 C11 3.644(3) . C3 H12 3.65(3) 4_554 C3 C11 3.646(3) 3_656 C3 C6 3.648(3) 3_656 N2 N2 3.655(3) 3_656 C10 H3 3.66(2) 4_455 C7 H8 3.66(2) 2_545 C7 O12 3.665(2) . C10 C10 3.675(3) 2_556 C10 C10 3.675(3) 2_546 C8 C10 3.680(3) 1_554 C7 C11 3.681(3) 1_554 C3 C5 3.686(3) 3_666 C7 C8 3.690(3) 2 N1 C10 3.692(2) . N1 C8 3.696(2) . C3 C3 3.697(3) 3_666 C7 H8 3.70(2) 2 C8 H11 3.71(2) 2_556 N4 H11 3.71(2) 3_657 C6 H8 3.71(2) 2_545 C5 H3 3.72(2) 1_556 C7 H10 3.73(2) . C10 H7 3.73(2) . N4 H3 3.73(2) 1_556 N4 H3 3.74(2) 3_666 C11 H8 3.74(2) . N2 C3 3.746(3) 3_656 N2 N4 3.753(3) 3_656 N1 H3 3.75(2) 3_656 C8 H11 3.75(2) . C7 C10 3.758(3) 2_556 C6 O12 3.783(2) 2_556 N1 H5 3.79(2) 1_554 C11 H8 3.79(2) 1_556 C8 C9 3.790(3) 2 C8 C8 3.796(3) 2_545 C8 C8 3.796(3) 2 C8 H11 3.80(2) 1_554 N2 H11 3.80(2) 3_656 N1 H12 3.82(3) 4 O12 H10 3.82(2) 2_556 C10 C11 3.821(3) 2_546 N1 O12 3.826(2) 2_556 C3 O12 3.827(3) 4 C7 C10 3.829(3) 1_554 N1 C3 3.832(3) 3_666 C5 H7 3.83(2) . C11 O12 3.833(2) 2_556 C3 H7 3.83(2) . N4 H7 3.84(2) 3_666 C6 C10 3.838(3) 2_556 C7 H12 3.85(3) . N2 O12 3.849(2) 2 N1 H10 3.86(2) 2_556 C9 C11 3.858(3) 2_556 C7 H5 3.86(2) 1_554 C5 H12 3.86(3) 2_556 N2 C3 3.869(3) 3_666 C5 H7 3.89(2) 1_556 N2 H11 3.89(2) . N1 N1 3.902(2) 3_656 O12 H11 3.91(2) 2_546 N1 N4 3.914(2) 3_656 C8 H3 3.92(2) 4_454 C9 H8 3.93(2) 1_556 N2 H12 3.93(3) 4 N1 N4 3.946(2) 3_666 C6 H11 3.95(2) 1_554 C6 H7 3.96(2) 1_556 C10 H3 3.96(2) 3_656 N2 H5 3.97(2) 3_656 C3 C5 3.972(3) 3_656 C9 H10 3.98(2) 1_554 C11 O12 3.976(2) 2_546 N4 C6 3.990(3) 3_656 N1 H12 3.99(3) 2 C5 H11 3.99(2) 3_657 C3 H3 4.00(2) 3_666 N2 H3 4.00(2) 3_666 C7 H5 4.01(2) . N2 C5 4.015(3) 3_666 C8 H8 4.02(2) 2 C11 H12 4.02(3) 2_546 C3 H5 4.02(2) 3_666 N4 N4 4.031(3) 3_666 C8 C11 4.031(3) 1_554 C10 H8 4.04(2) 2_546 N2 O12 4.041(2) 4_554 C3 C5 4.041(3) 1_554 C8 C11 4.075(3) 2_556 C8 C10 4.106(3) 2 N1 C5 4.108(3) 3_656 N2 C6 4.115(2) 3_656 C6 O12 4.123(2) . C3 C7 4.123(3) . C7 C10 4.132(3) 2 C10 O12 4.144(2) 2_546 C7 C8 4.144(3) 2_545 C9 C11 4.166(3) 2_546 N2 N4 4.166(2) 1_554 C3 C8 4.171(3) 4 N4 C5 4.180(3) 3_666 N1 C9 4.189(2) . C8 O12 4.190(2) 2 N2 C11 4.212(3) 3_656 C10 C11 4.242(3) 2_556 C3 C3 4.261(3) 3_656 N4 C11 4.271(3) . N2 C8 4.278(2) . C3 C9 4.279(3) 4_554 C6 C9 4.285(3) 2_556 N4 C11 4.306(3) 3_656 C9 C10 4.311(3) 2_546 C3 N4 4.333(3) 1_554 C7 O12 4.355(2) 2_556 C5 C10 4.359(3) . N1 O12 4.364(2) 2 C6 O12 4.367(2) 2 N4 O12 4.369(2) 2_556 N4 O12 4.380(2) 4_554 N2 C11 4.384(2) 1_554 C10 O12 4.410(2) 2_556 C8 C11 4.426(3) 2 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 O12 H12 N4 4_454 1.00(3) 1.72(3) 2.704(2) 166(3) yes C5 H5 N2 1_556 0.97(2) 2.58(2) 3.489(3) 157(2) yes C3 H3 O12 4_554 0.97(2) 2.44(2) 3.373(3) 161(2) yes C7 H7 O12 2_555 0.97(2) 2.58(2) 3.455(2) 151(2) 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 N2 N1 C6 C7 -31.3(2) yes