#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/56/2005692.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_2005692 loop_ _publ_author_name 'Collins, D. J.' 'Hughes, T. C.' 'Johnson, W. M.' 'Mackay, M. F.' _publ_section_title ; 2-Methyl-3-phenyl-2,5-dihydro-1,2,4-triazin-6(1H)-one Methanol Solvate and 4-Methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 2865 _journal_page_last 2868 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C10 H11 N3 O, C H4 O' _chemical_formula_structural 'C10 H11 N3 O (C H4 O)' _chemical_formula_sum 'C11 H15 N3 O2' _chemical_formula_weight 221.3 _chemical_name_systematic '2-Methyl-3-phenyl-2,5-dihydro-1,2,4-triazin-6(1H)-one Methanol Solvate' _chemical_temperature_decomposition 470 _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 8.856(1) _cell_length_b 24.985(2) _cell_length_c 10.507(1) _cell_measurement_reflns_used 30 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 33 _cell_measurement_theta_min 16 _cell_volume 2324.9(4) _computing_cell_refinement 'AFC/MSC Software' _computing_data_collection 'AFC/MSC Software (Rigaku Corporation, 1988)' _computing_data_reduction 'AFC/MSC Software' _computing_molecular_graphics 'ORTEPII (Johnson,1976)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 291(2) _diffrn_measurement_device 'Rigaku-AFC diffractometer' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1307 _diffrn_reflns_theta_max 63.1 _diffrn_reflns_theta_min 3.5 _diffrn_standards_decay_% <12% _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.73 _exptl_absorpt_correction_T_max 0.802 _exptl_absorpt_correction_T_min 0.726 _exptl_absorpt_correction_type 'SHELX76 gaussian (Sheldrick, 1976)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description 'regular prism' _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.38 _refine_diff_density_max 0.217 _refine_diff_density_min -0.166 _refine_ls_extinction_coef 0.0035(6) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_obs 1.083 _refine_ls_hydrogen_treatment ; H atoms of methanol not located. Other H atoms refined with common U~iso~ = 0.091(4)\%A ; _refine_ls_matrix_type full _refine_ls_number_parameters 190 _refine_ls_number_reflns 1307 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.050 _refine_ls_shift/esd_max -0.090 _refine_ls_shift/esd_mean 0.007 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0944P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_obs 0.131 _reflns_number_observed 1087 _reflns_number_total 1307 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file ta1096.cif _[local]_cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been '470 K (Dec.)'. The value '470 K (Dec.)' was changed to '470'. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2005692 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' 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_type_symbol N1 1 0.3175(3) 0.52764(10) 0.4119(2) 0.0554(8) Uani d N N2 1 0.4021(3) 0.56824(11) 0.3497(2) 0.0542(8) Uani d N C3 1 0.3999(4) 0.57497(13) 0.2249(3) 0.0522(9) Uani d C N4 1 0.3424(4) 0.53732(11) 0.1525(2) 0.0565(9) Uani d N C5 1 0.3149(6) 0.48323(14) 0.2039(3) 0.0606(11) Uani d C C6 1 0.2714(4) 0.48771(13) 0.3414(3) 0.0517(9) Uani d C O6 1 0.1916(3) 0.45062(9) 0.3889(2) 0.0636(8) Uani d O C7 1 0.4519(4) 0.62547(13) 0.1643(3) 0.0504(9) Uani d C C8 1 0.5515(5) 0.6224(2) 0.0621(3) 0.0605(10) Uani d C C9 1 0.5974(5) 0.6685(2) 0.0001(4) 0.0688(11) Uani d C C10 1 0.5430(6) 0.7168(2) 0.0393(4) 0.0817(14) Uani d C C11 1 0.4444(6) 0.7212(2) 0.1412(4) 0.0829(14) Uani d C C12 1 0.3972(5) 0.67499(15) 0.2032(4) 0.0656(11) Uani d C C13 1 0.4859(5) 0.6010(2) 0.4397(4) 0.0677(12) Uani d C OM1 1 0.1705(4) 0.35671(10) 0.2561(2) 0.0777(9) Uani d O CM1 1 0.2712(7) 0.3266(2) 0.3294(5) 0.0844(14) Uani d C H4 1 0.333(4) 0.5436(14) 0.064(5) 0.091 Uiso d H H5a 1 0.411(5) 0.4656(16) 0.196(4) 0.091 Uiso d H H5b 1 0.224(5) 0.4704(16) 0.157(4) 0.091 Uiso d H H8 1 0.587(5) 0.5903(16) 0.033(4) 0.091 Uiso d H H9 1 0.672(5) 0.6655(15) -0.074(4) 0.091 Uiso d H H10 1 0.571(5) 0.7470(18) -0.002(4) 0.091 Uiso d H H11 1 0.403(5) 0.7510(17) 0.166(4) 0.091 Uiso d H H12 1 0.319(5) 0.6781(15) 0.273(4) 0.091 Uiso d H H13a 1 0.553(5) 0.5787(16) 0.487(4) 0.091 Uiso d H H13b 1 0.413(5) 0.6203(17) 0.495(4) 0.091 Uiso d H H13c 1 0.562(4) 0.6265(17) 0.397(4) 0.091 Uiso d H HMa 1 0.282(5) 0.2897(16) 0.296(4) 0.091 Uiso d H HMb 1 0.254(5) 0.3343(15) 0.415(5) 0.091 Uiso d H HMc 1 0.378(5) 0.3424(16) 0.311(4) 0.091 Uiso d 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 0.082(2) 0.055(2) 0.0283(12) -0.001(2) 0.0033(14) 0.0022(12) N2 0.079(2) 0.055(2) 0.0286(13) -0.002(2) -0.0047(14) -0.0031(11) C3 0.072(2) 0.056(2) 0.029(2) 0.005(2) 0.001(2) -0.0016(14) N4 0.092(2) 0.053(2) 0.0237(12) -0.004(2) -0.002(2) -0.0015(12) C5 0.101(3) 0.051(2) 0.030(2) -0.008(2) 0.006(2) -0.0002(14) C6 0.076(2) 0.054(2) 0.0243(14) 0.008(2) -0.002(2) 0.002(2) O6 0.100(2) 0.0603(14) 0.0308(11) -0.0073(15) 0.0061(13) 0.0030(11) C7 0.067(2) 0.053(2) 0.0313(15) -0.002(2) -0.003(2) -0.0037(14) C8 0.079(3) 0.064(2) 0.038(2) 0.001(2) 0.004(2) -0.002(2) C9 0.083(3) 0.074(3) 0.049(2) -0.007(2) 0.006(2) -0.001(2) C10 0.109(4) 0.073(3) 0.063(2) -0.022(3) 0.005(3) 0.014(2) C11 0.115(4) 0.054(2) 0.080(3) 0.004(3) 0.017(3) -0.006(2) C12 0.090(3) 0.057(2) 0.050(2) 0.004(2) 0.014(2) -0.003(2) C13 0.084(3) 0.077(3) 0.042(2) -0.006(2) -0.013(2) -0.010(2) OM1 0.095(2) 0.082(2) 0.0563(14) 0.003(2) -0.0077(15) -0.0034(13) CM1 0.109(4) 0.081(3) 0.063(2) 0.011(3) -0.009(3) -0.006(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 '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' 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 N2 116.6(3) yes C3 N2 N1 122.7(3) yes C3 N2 C13 125.5(3) yes N1 N2 C13 111.8(3) yes N4 C3 N2 119.3(3) yes N4 C3 C7 118.7(3) yes N2 C3 C7 121.9(3) yes C3 N4 C5 120.6(3) yes N4 C5 C6 109.1(3) yes O6 C6 N1 120.6(3) yes O6 C6 C5 117.9(3) yes N1 C6 C5 121.5(3) yes C12 C7 C8 119.8(3) no C12 C7 C3 121.4(3) yes C8 C7 C3 118.7(3) yes C9 C8 C7 120.3(4) no C10 C9 C8 119.4(4) no C9 C10 C11 121.8(4) no C10 C11 C12 119.1(4) no C7 C12 C11 119.8(4) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C6 1.308(4) yes N1 N2 1.421(4) yes N2 C3 1.322(4) yes N2 C13 1.455(4) yes C3 N4 1.312(4) yes C3 C7 1.486(4) yes N4 C5 1.475(4) yes C5 C6 1.499(4) yes C6 O6 1.268(4) yes C7 C12 1.390(5) no C7 C8 1.392(5) no C8 C9 1.385(5) no C9 C10 1.362(6) no C10 C11 1.385(6) no C11 C12 1.391(5) no OM1 CM1 1.398(5) 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 N2 C3 N4 -13.7(3) yes N2 C3 N4 C5 -14.8(5) yes C3 N4 C5 C6 33.5(4) yes N4 C5 C6 N1 -27.7(4) yes C5 C6 N1 N2 4.1(4) yes C6 N1 N2 C3 19.1(4) yes N4 C3 N2 C13 167.8(3) yes C7 C3 N2 C13 -16.0(5) yes N2 N1 C6 O6 -178.0(3) yes N2 C3 C7 C12 -51.8(5) yes _journal_paper_doi 10.1107/S0108270196008335