#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/73/2207344.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_2207344 loop_ _publ_author_name 'Qiong Chen' 'Yuan-Xiang Li' 'Xiao-Wei Hu' 'Guang-Fu Yang' _publ_section_title ; Ethyl 2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-yloxy)benzoate ; _journal_coeditor_code SJ6136 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3842 _journal_page_last o3843 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C16 H16 N4 O3' _chemical_formula_moiety 'C16 H16 N4 O3' _chemical_formula_sum 'C16 H16 N4 O3' _chemical_formula_weight 312.33 _chemical_name_systematic ; Ethyl 2-(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidin-2-yloxy)benzoate ; _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' _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 102.038(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.0013(13) _cell_length_b 10.5217(15) _cell_length_c 17.152(3) _cell_measurement_reflns_used 2092 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 21.57 _cell_measurement_theta_min 2.28 _cell_volume 1588.7(4) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1997)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 4K 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 0.0650 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 9593 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.28 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.259 _refine_diff_density_min -0.242 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3470 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.914 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0508 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0644P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1147 _refine_ls_wR_factor_ref 0.1280 _reflns_number_gt 2093 _reflns_number_total 3470 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sj6136.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 1588.8(4) _cod_database_code 2207344 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 0.0016 '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_ _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 C1 0.3764(2) -0.15737(17) 1.05091(13) 0.0723(6) Uani d . 1 C H1A 0.3357 -0.2160 1.0090 0.108 Uiso calc R 1 H H1B 0.3807 -0.1974 1.1016 0.108 Uiso calc R 1 H H1C 0.4768 -0.1324 1.0463 0.108 Uiso calc R 1 H C2 0.2764(2) -0.04238(16) 1.04429(11) 0.0529(5) Uani d . 1 C C3 0.1942(2) -0.01446(17) 1.10334(10) 0.0554(5) Uani d . 1 C H3 0.2067 -0.0659 1.1483 0.066 Uiso calc R 1 H C4 0.0970(2) 0.08568(16) 1.09658(9) 0.0495(4) Uani d . 1 C C5 0.0020(2) 0.12361(19) 1.15375(10) 0.0652(5) Uani d . 1 C H5A 0.0405 0.2012 1.1797 0.098 Uiso calc R 1 H H5B 0.0048 0.0579 1.1929 0.098 Uiso calc R 1 H H5C -0.1009 0.1362 1.1256 0.098 Uiso calc R 1 H C6 0.17278(19) 0.12849(15) 0.97284(9) 0.0455(4) Uani d . 1 C C7 0.03910(19) 0.28673(15) 0.93792(9) 0.0457(4) Uani d . 1 C C8 0.0403(2) 0.43507(16) 0.83608(10) 0.0489(4) Uani d . 1 C C9 0.1316(2) 0.53948(18) 0.85550(11) 0.0633(5) Uani d . 1 C H9 0.1477 0.5734 0.9067 0.076 Uiso calc R 1 H C10 0.1994(2) 0.59379(18) 0.79864(13) 0.0682(6) Uani d . 1 C H10 0.2614 0.6646 0.8116 0.082 Uiso calc R 1 H C11 0.1761(2) 0.54420(18) 0.72316(12) 0.0638(5) Uani d . 1 C H11 0.2223 0.5812 0.6850 0.077 Uiso calc R 1 H C12 0.0839(2) 0.43939(17) 0.70397(10) 0.0560(5) Uani d . 1 C H12 0.0691 0.4056 0.6528 0.067 Uiso calc R 1 H C13 0.01232(19) 0.38311(15) 0.75992(10) 0.0481(4) Uani d . 1 C C14 -0.0934(2) 0.27458(17) 0.73765(11) 0.0572(5) Uani d . 1 C C15 -0.1682(3) 0.1073(2) 0.64504(13) 0.0827(7) Uani d . 1 C H15A -0.2725 0.1364 0.6298 0.099 Uiso calc R 1 H H15B -0.1623 0.0439 0.6867 0.099 Uiso calc R 1 H C16 -0.1190(4) 0.0519(3) 0.57549(17) 0.1243(10) Uani d . 1 C H16A -0.1134 0.1177 0.5374 0.186 Uiso calc R 1 H H16B -0.1908 -0.0114 0.5514 0.186 Uiso calc R 1 H H16C -0.0208 0.0136 0.5925 0.186 Uiso calc R 1 H N1 0.26752(16) 0.02903(13) 0.97933(8) 0.0519(4) Uani d . 1 N N2 0.08897(16) 0.15618(12) 1.02918(7) 0.0444(3) Uani d . 1 N N3 -0.00021(16) 0.26124(13) 1.00644(8) 0.0473(4) Uani d . 1 N N4 0.14090(16) 0.21337(13) 0.91347(8) 0.0492(4) Uani d . 1 N O1 -0.02912(14) 0.38772(11) 0.89632(7) 0.0581(4) Uani d . 1 O O2 -0.19345(18) 0.24522(13) 0.77099(8) 0.0815(5) Uani d . 1 O O3 -0.06801(16) 0.21351(12) 0.67368(8) 0.0734(4) Uani d . 1 O 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 C1 0.0623(13) 0.0614(13) 0.0899(15) 0.0051(10) 0.0082(11) 0.0141(11) C2 0.0466(10) 0.0465(11) 0.0619(11) -0.0081(8) 0.0031(9) 0.0021(9) C3 0.0609(12) 0.0545(12) 0.0487(10) -0.0128(9) 0.0066(9) 0.0093(9) C4 0.0558(11) 0.0501(11) 0.0423(9) -0.0136(9) 0.0098(8) 0.0021(8) C5 0.0787(14) 0.0738(14) 0.0481(11) -0.0082(11) 0.0245(10) 0.0047(9) C6 0.0454(10) 0.0495(10) 0.0427(9) -0.0039(8) 0.0120(8) -0.0021(8) C7 0.0501(10) 0.0475(10) 0.0411(9) -0.0009(8) 0.0134(8) 0.0002(8) C8 0.0526(11) 0.0511(11) 0.0467(10) 0.0124(8) 0.0185(8) 0.0093(8) C9 0.0701(13) 0.0624(13) 0.0588(12) 0.0013(10) 0.0168(10) -0.0041(10) C10 0.0695(14) 0.0617(13) 0.0766(14) -0.0056(10) 0.0224(11) -0.0014(11) C11 0.0637(13) 0.0662(13) 0.0678(13) 0.0037(10) 0.0280(10) 0.0161(10) C12 0.0616(12) 0.0616(12) 0.0470(10) 0.0090(9) 0.0165(9) 0.0088(9) C13 0.0492(10) 0.0474(10) 0.0484(10) 0.0086(8) 0.0120(8) 0.0076(8) C14 0.0607(13) 0.0570(12) 0.0517(11) 0.0084(10) 0.0068(9) 0.0124(9) C15 0.0890(17) 0.0633(14) 0.0860(16) -0.0039(12) -0.0044(13) -0.0054(12) C16 0.125(2) 0.121(2) 0.124(2) -0.0128(19) 0.0178(19) -0.0581(19) N1 0.0509(9) 0.0508(9) 0.0549(9) 0.0002(7) 0.0130(7) 0.0032(7) N2 0.0504(8) 0.0448(8) 0.0389(7) -0.0064(6) 0.0116(6) -0.0001(6) N3 0.0551(9) 0.0482(9) 0.0410(7) -0.0002(7) 0.0156(6) 0.0001(6) N4 0.0563(9) 0.0521(9) 0.0428(8) 0.0049(7) 0.0183(7) 0.0044(6) O1 0.0666(8) 0.0623(8) 0.0516(7) 0.0172(6) 0.0264(6) 0.0147(6) O2 0.0862(11) 0.0899(11) 0.0721(9) -0.0229(8) 0.0251(9) 0.0091(8) O3 0.0740(10) 0.0682(9) 0.0777(9) -0.0038(7) 0.0153(8) -0.0166(7) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.498(2) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 C2 N1 1.332(2) C2 C3 1.404(2) C3 C4 1.359(2) C3 H3 0.9300 C4 N2 1.3627(19) C4 C5 1.484(2) C5 H5A 0.9600 C5 H5B 0.9600 C5 H5C 0.9600 C6 N1 1.340(2) C6 N4 1.3399(19) C6 N2 1.3755(19) C7 N3 1.324(2) C7 N4 1.331(2) C7 O1 1.3537(19) C8 C9 1.371(2) C8 C13 1.390(2) C8 O1 1.4056(18) C9 C10 1.378(2) C9 H9 0.9300 C10 C11 1.371(3) C10 H10 0.9300 C11 C12 1.378(2) C11 H11 0.9300 C12 C13 1.394(2) C12 H12 0.9300 C13 C14 1.485(2) C14 O2 1.203(2) C14 O3 1.332(2) C15 O3 1.456(2) C15 C16 1.476(3) C15 H15A 0.9700 C15 H15B 0.9700 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 N2 N3 1.3740(18) 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 C1 H1A 109.5 ? C2 C1 H1B 109.5 ? H1A C1 H1B 109.5 ? C2 C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? N1 C2 C3 122.45(16) ? N1 C2 C1 116.68(17) ? C3 C2 C1 120.86(17) ? C4 C3 C2 121.83(16) ? C4 C3 H3 119.1 ? C2 C3 H3 119.1 ? C3 C4 N2 114.43(16) ? C3 C4 C5 126.99(16) ? N2 C4 C5 118.58(16) ? C4 C5 H5A 109.5 ? C4 C5 H5B 109.5 ? H5A C5 H5B 109.5 ? C4 C5 H5C 109.5 ? H5A C5 H5C 109.5 ? H5B C5 H5C 109.5 ? N1 C6 N4 127.98(15) ? N1 C6 N2 122.68(15) ? N4 C6 N2 109.33(14) ? N3 C7 N4 119.43(15) ? N3 C7 O1 116.81(14) ? N4 C7 O1 123.75(14) yes C9 C8 C13 121.71(16) ? C9 C8 O1 116.19(15) yes C13 C8 O1 122.03(16) ? C8 C9 C10 119.47(18) ? C8 C9 H9 120.3 ? C10 C9 H9 120.3 ? C11 C10 C9 120.50(19) ? C11 C10 H10 119.8 ? C9 C10 H10 119.8 ? C10 C11 C12 119.74(18) ? C10 C11 H11 120.1 ? C12 C11 H11 120.1 ? C11 C12 C13 121.14(17) ? C11 C12 H12 119.4 ? C13 C12 H12 119.4 ? C8 C13 C12 117.43(17) ? C8 C13 C14 121.68(15) ? C12 C13 C14 120.86(16) ? O2 C14 O3 122.81(19) ? O2 C14 C13 125.33(18) ? O3 C14 C13 111.83(17) yes O3 C15 C16 107.8(2) yes O3 C15 H15A 110.1 ? C16 C15 H15A 110.1 ? O3 C15 H15B 110.1 ? C16 C15 H15B 110.1 ? H15A C15 H15B 108.5 ? C15 C16 H16A 109.5 ? C15 C16 H16B 109.5 ? H16A C16 H16B 109.5 ? C15 C16 H16C 109.5 ? H16A C16 H16C 109.5 ? H16B C16 H16C 109.5 ? C2 N1 C6 115.85(15) ? C4 N2 N3 127.10(14) ? C4 N2 C6 122.74(15) ? N3 N2 C6 110.16(12) ? C7 N3 N2 99.58(13) ? C7 N4 C6 101.50(13) ? C7 O1 C8 116.31(12) yes C14 O3 C15 116.58(17) 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 N1 C2 C3 C4 1.9(3) ? C1 C2 C3 C4 -176.62(16) ? C2 C3 C4 N2 -1.1(2) ? C2 C3 C4 C5 178.79(16) ? C13 C8 C9 C10 -0.9(3) ? O1 C8 C9 C10 -177.81(16) ? C8 C9 C10 C11 0.0(3) ? C9 C10 C11 C12 0.1(3) ? C10 C11 C12 C13 0.6(3) ? C9 C8 C13 C12 1.5(3) ? O1 C8 C13 C12 178.30(14) ? C9 C8 C13 C14 -176.48(16) ? O1 C8 C13 C14 0.3(2) yes C11 C12 C13 C8 -1.4(3) ? C11 C12 C13 C14 176.65(15) ? C8 C13 C14 O2 22.2(3) ? C12 C13 C14 O2 -155.71(18) ? C8 C13 C14 O3 -159.56(15) ? C12 C13 C14 O3 22.5(2) yes C3 C2 N1 C6 -1.2(2) ? C1 C2 N1 C6 177.35(15) ? N4 C6 N1 C2 -178.77(16) ? N2 C6 N1 C2 -0.1(2) ? C3 C4 N2 N3 179.29(15) ? C5 C4 N2 N3 -0.6(2) ? C3 C4 N2 C6 -0.2(2) ? C5 C4 N2 C6 179.92(15) ? N1 C6 N2 C4 0.9(2) ? N4 C6 N2 C4 179.73(14) ? N1 C6 N2 N3 -178.74(14) ? N4 C6 N2 N3 0.14(18) ? N4 C7 N3 N2 -0.15(19) ? O1 C7 N3 N2 179.56(13) ? C4 N2 N3 C7 -179.57(15) ? C6 N2 N3 C7 0.00(16) ? N3 C7 N4 C6 0.2(2) ? O1 C7 N4 C6 -179.46(15) ? N1 C6 N4 C7 178.59(16) ? N2 C6 N4 C7 -0.21(17) ? N3 C7 O1 C8 163.43(15) ? N4 C7 O1 C8 -16.9(2) yes C9 C8 O1 C7 -98.75(18) yes C13 C8 O1 C7 84.32(19) ? O2 C14 O3 C15 -0.1(3) ? C13 C14 O3 C15 -178.31(14) yes C16 C15 O3 C14 -178.88(19) 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 C3 H3 O2 3_557 0.93 2.36 3.248(2) 160 _cod_database_fobs_code 2207344