#------------------------------------------------------------------------------ #$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $ #$Revision: 853 $ #$URL: svn://www.crystallography.net/cod/cif/2/2205086.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_2205086 _space_group_IT_number 9 _symmetry_space_group_name_Hall 'C -2yc' _symmetry_space_group_name_H-M 'C 1 c 1' _[local]_cod_cif_authors_sg_H-M 'C c' loop_ _publ_author_name 'Fa-Qian Liu' 'Wei-Hua Li' 'Hai-Bin Song' 'Lu-De Lu' 'Xu-Jie Yang' 'Xin Wang' _publ_section_title ; 1-(4-Hydroxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o400 _journal_page_last o401 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C11 H11 N3 O2' _chemical_formula_moiety 'C11 H11 N3 O2' _chemical_formula_sum 'C11 H11 N3 O2' _chemical_formula_weight 217.23 _chemical_name_systematic ; 1-(4-Hydroxyphenyl)-3-(1H-1,2,4-triazol-1-yl)propan-1-one ; _symmetry_cell_setting Monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.929(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 22.759(4) _cell_length_b 5.5729(9) _cell_length_c 8.3902(14) _cell_measurement_reflns_used 1098 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.71 _cell_measurement_theta_min 3.58 _cell_volume 1064.0(3) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0216 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 3413 _diffrn_reflns_theta_full 27.85 _diffrn_reflns_theta_max 27.85 _diffrn_reflns_theta_min 1.79 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_T_max 0.981 _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.121 _refine_diff_density_min -0.131 _refine_ls_abs_structure_details none _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 149 _refine_ls_number_reflns 1271 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0296 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.0744P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0710 _refine_ls_wR_factor_ref 0.0761 _reflns_number_gt 1006 _reflns_number_total 1271 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hg6135.cif loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol N1 0.14909(8) 0.2545(3) 0.1435(2) 0.0422(4) Uani d . 1 N N2 0.17183(8) 0.0500(3) 0.0831(2) 0.0547(5) Uani d . 1 N N3 0.21645(8) 0.3727(3) -0.0190(2) 0.0518(5) Uani d . 1 N O1 0.03756(7) 0.5294(3) 0.0556(2) 0.0598(5) Uani d . 1 O O2 -0.21274(6) 0.1802(3) -0.17034(17) 0.0532(4) Uani d D 1 O H2 -0.2324(10) 0.073(4) -0.120(3) 0.069(9) Uiso d D 1 H C1 0.01373(9) 0.3386(4) 0.0832(2) 0.0429(5) Uani d . 1 C C2 0.04437(9) 0.1561(4) 0.1890(3) 0.0470(5) Uani d . 1 C H2A 0.0519 0.0125 0.1273 0.056 Uiso calc R 1 H H2B 0.0185 0.1126 0.2751 0.056 Uiso calc R 1 H C3 0.10210(10) 0.2470(4) 0.2596(2) 0.0504(5) Uani d . 1 C H3A 0.0962 0.4069 0.3021 0.060 Uiso calc R 1 H H3B 0.1140 0.1435 0.3474 0.060 Uiso calc R 1 H C4 0.21187(10) 0.1313(4) -0.0136(3) 0.0564(6) Uani d . 1 C H4 0.2353 0.0305 -0.0738 0.068 Uiso calc R 1 H C5 0.17636(9) 0.4422(4) 0.0827(2) 0.0463(5) Uani d . 1 C H5 0.1683 0.6011 0.1082 0.056 Uiso calc R 1 H C6 -0.04500(8) 0.2822(4) 0.0161(2) 0.0384(4) Uani d . 1 C C7 -0.07716(9) 0.0807(4) 0.0587(2) 0.0462(5) Uani d . 1 C H7 -0.0606 -0.0310 0.1284 0.055 Uiso calc R 1 H C8 -0.13323(9) 0.0440(4) -0.0007(3) 0.0480(5) Uani d . 1 C H8 -0.1543 -0.0905 0.0306 0.058 Uiso calc R 1 H C9 -0.15838(8) 0.2058(4) -0.1068(2) 0.0413(5) Uani d . 1 C C10 -0.12644(9) 0.4057(4) -0.1531(3) 0.0477(5) Uani d . 1 C H10 -0.1425 0.5136 -0.2262 0.057 Uiso calc R 1 H C11 -0.07100(9) 0.4437(4) -0.0906(2) 0.0456(5) Uani d . 1 C H11 -0.0504 0.5802 -0.1203 0.055 Uiso calc R 1 H 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 0.0343(8) 0.0424(9) 0.0498(9) -0.0005(7) -0.0046(7) -0.0051(7) N2 0.0485(11) 0.0427(9) 0.0730(14) -0.0028(9) 0.0049(10) -0.0103(9) N3 0.0374(9) 0.0585(11) 0.0595(11) -0.0056(9) -0.0024(8) 0.0010(9) O1 0.0462(9) 0.0521(9) 0.0807(11) -0.0142(7) -0.0069(7) 0.0130(8) O2 0.0383(9) 0.0641(10) 0.0572(9) -0.0041(7) -0.0025(7) 0.0040(8) C1 0.0385(11) 0.0434(10) 0.0469(12) -0.0021(9) 0.0043(9) -0.0003(9) C2 0.0386(11) 0.0506(11) 0.0518(12) 0.0009(9) 0.0043(9) 0.0063(10) C3 0.0414(11) 0.0658(13) 0.0439(11) 0.0032(10) -0.0009(9) 0.0016(10) C4 0.0429(12) 0.0578(13) 0.0686(15) -0.0013(11) 0.0063(11) -0.0145(12) C5 0.0389(11) 0.0419(10) 0.0579(14) -0.0015(9) -0.0073(10) 0.0003(10) C6 0.0352(11) 0.0406(11) 0.0395(11) -0.0012(8) 0.0041(8) 0.0013(8) C7 0.0426(12) 0.0432(11) 0.0529(13) -0.0036(9) -0.0003(10) 0.0080(9) C8 0.0426(12) 0.0439(11) 0.0575(13) -0.0073(10) 0.0016(9) 0.0076(10) C9 0.0346(11) 0.0459(11) 0.0435(11) -0.0006(9) 0.0038(8) -0.0051(9) C10 0.0441(12) 0.0474(12) 0.0517(13) 0.0020(10) 0.0002(10) 0.0107(10) C11 0.0416(11) 0.0426(11) 0.0527(12) -0.0073(9) 0.0053(9) 0.0076(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 1.323(3) ? N1 N2 1.354(2) ? N1 C3 1.459(3) yes N2 C4 1.311(3) ? N3 C5 1.317(3) ? N3 C4 1.350(3) ? O1 C1 1.218(2) yes O2 C9 1.347(2) yes O2 H2 0.857(10) ? C1 C6 1.476(3) yes C1 C2 1.513(3) yes C2 C3 1.519(3) ? C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 H3A 0.9700 ? C3 H3B 0.9700 ? C4 H4 0.9300 ? C5 H5 0.9300 ? C6 C7 1.390(3) ? C6 C11 1.395(3) ? C7 C8 1.378(3) ? C7 H7 0.9300 ? C8 C9 1.384(3) ? C8 H8 0.9300 ? C9 C10 1.389(3) ? C10 C11 1.375(3) ? C10 H10 0.9300 ? C11 H11 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C5 N1 N2 109.66(17) C5 N1 C3 129.36(18) N2 N1 C3 120.98(17) C4 N2 N1 102.39(17) C5 N3 C4 102.49(18) C9 O2 H2 111.2(18) O1 C1 C6 121.13(18) O1 C1 C2 119.75(18) C6 C1 C2 119.12(17) C1 C2 C3 113.09(18) C1 C2 H2A 109.0 C3 C2 H2A 109.0 C1 C2 H2B 109.0 C3 C2 H2B 109.0 H2A C2 H2B 107.8 N1 C3 C2 112.83(17) N1 C3 H3A 109.0 C2 C3 H3A 109.0 N1 C3 H3B 109.0 C2 C3 H3B 109.0 H3A C3 H3B 107.8 N2 C4 N3 114.9(2) N2 C4 H4 122.6 N3 C4 H4 122.6 N3 C5 N1 110.61(19) N3 C5 H5 124.7 N1 C5 H5 124.7 C7 C6 C11 117.82(17) C7 C6 C1 123.46(17) C11 C6 C1 118.66(17) C8 C7 C6 121.02(19) C8 C7 H7 119.5 C6 C7 H7 119.5 C7 C8 C9 120.4(2) C7 C8 H8 119.8 C9 C8 H8 119.8 O2 C9 C8 123.56(19) O2 C9 C10 117.12(17) C8 C9 C10 119.31(18) C11 C10 C9 119.90(18) C11 C10 H10 120.1 C9 C10 H10 120.1 C10 C11 C6 121.48(18) C10 C11 H11 119.3 C6 C11 H11 119.3 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 C5 N1 N2 C4 -0.6(2) ? C3 N1 N2 C4 -179.81(19) ? O1 C1 C2 C3 4.1(3) yes C6 C1 C2 C3 -175.41(17) ? C5 N1 C3 C2 112.7(2) yes N2 N1 C3 C2 -68.2(2) yes C1 C2 C3 N1 -74.4(2) ? N1 N2 C4 N3 0.1(2) ? C5 N3 C4 N2 0.3(3) ? C4 N3 C5 N1 -0.7(2) ? N2 N1 C5 N3 0.9(2) ? C3 N1 C5 N3 179.99(19) ? O1 C1 C6 C7 -172.0(2) yes C2 C1 C6 C7 7.5(3) ? O1 C1 C6 C11 5.2(3) ? C2 C1 C6 C11 -175.30(18) ? C11 C6 C7 C8 -1.0(3) ? C1 C6 C7 C8 176.2(2) ? C6 C7 C8 C9 1.1(3) ? C7 C8 C9 O2 179.5(2) ? C7 C8 C9 C10 0.2(3) ? O2 C9 C10 C11 179.09(19) ? C8 C9 C10 C11 -1.5(3) ? C9 C10 C11 C6 1.6(3) ? C7 C6 C11 C10 -0.4(3) ? C1 C6 C11 C10 -177.7(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 O2 H2 N3 3_445 0.857(10) 1.834(11) 2.685(2) 172(3) yes C3 H3A O1 2_565 0.97 2.55 3.162(3) 120 yes C3 H3B N2 2_555 0.97 2.59 3.534(3) 163 yes C4 H4 O2 3_545 0.93 2.43 3.327(3) 162 yes C5 H5 N2 1_565 0.93 2.51 3.389(5) 157 yes