#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/56/2005693.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_2005693 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_paper_doi 10.1107/S0108270196008335 _journal_volume 52 _journal_year 1996 _chemical_formula_moiety 'C10 H11 N3 O' _chemical_formula_structural 'C10 H11 N3 O' _chemical_formula_sum 'C10 H11 N3 O' _chemical_formula_weight 189.22 _chemical_name_systematic 4-Methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one _chemical_temperature_decomposition 408.5(5) _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 'SHELXL-93 (Sheldrick,1993)' _cell_angle_alpha 90.00 _cell_angle_beta 98.71(1) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.6707(5) _cell_length_b 7.0151(5) _cell_length_c 20.722(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 32 _cell_measurement_theta_min 20 _cell_volume 958.52(11) _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 293.0(10) _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 0.016 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1743 _diffrn_reflns_theta_max 64.8 _diffrn_reflns_theta_min 4.3 _diffrn_standards_decay_% none _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_T_max 0.886 _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_type 'SHELX76 gaussian (Sheldrick, 1976)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.311 _exptl_crystal_description 'regular prism' _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.133 _refine_diff_density_min -0.225 _refine_ls_extinction_coef 0.050(3) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_obs 1.172 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 1594 _refine_ls_number_restraints 0 _refine_ls_R_factor_obs 0.037 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.2474P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_obs 0.093 _reflns_number_observed 1371 _reflns_number_total 1594 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ta1096.cif _cod_data_source_block 2 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' tag was changed to '_chemical_temperature_decomposition' since the value had been given as '408-409 K (Dec.)'. The value was changed to '408.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.2474P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.2474P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 958.50(10) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2005693 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_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 0.0400(8) 0.0360(8) 0.0524(8) -0.0003(6) -0.0099(6) 0.0004(6) N2 0.0355(7) 0.0374(7) 0.0492(8) 0.0025(6) -0.0058(6) 0.0026(6) C3 0.0354(8) 0.0357(8) 0.0408(8) 0.0011(7) 0.0016(6) 0.0023(7) N4 0.0411(8) 0.0346(8) 0.0615(9) -0.0010(6) -0.0089(7) 0.0052(7) C5 0.0465(10) 0.0380(10) 0.0594(11) 0.0071(8) -0.0098(8) 0.0008(8) C6 0.0402(9) 0.0382(9) 0.0477(9) 0.0007(7) -0.0043(7) 0.0079(7) O6 0.0476(7) 0.0440(7) 0.0794(9) 0.0003(5) -0.0248(6) 0.0076(6) C7 0.0335(8) 0.0392(9) 0.0399(8) -0.0010(7) 0.0024(6) 0.0041(7) C8 0.0399(9) 0.0463(9) 0.0471(9) 0.0013(8) 0.0018(7) -0.0021(8) C9 0.0435(9) 0.0560(11) 0.0474(10) -0.0072(8) -0.0039(8) -0.0014(8) C10 0.0354(9) 0.0651(12) 0.0562(11) -0.0004(9) -0.0053(8) 0.0081(9) C11 0.0396(9) 0.0513(10) 0.0590(11) 0.0084(8) 0.0049(8) 0.0057(8) C12 0.0393(9) 0.0438(9) 0.0448(9) 0.0014(7) 0.0027(7) 0.0008(7) C13 0.0642(13) 0.0395(10) 0.0570(11) -0.0114(9) -0.0008(10) 0.0057(9) 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 0.2477(2) 0.4287(2) 0.95301(7) 0.0445(4) Uani d N N2 1 0.0693(2) 0.4607(2) 0.90889(7) 0.0420(4) Uani d N C3 1 -0.0334(2) 0.3081(2) 0.89075(8) 0.0378(4) Uani d C N4 1 0.0351(2) 0.1289(2) 0.90749(7) 0.0474(4) Uani d N C5 1 0.2532(3) 0.1024(3) 0.92074(10) 0.0498(5) Uani d C C6 1 0.3519(2) 0.2660(2) 0.95940(8) 0.0432(4) Uani d C O6 1 0.5186(2) 0.2507(2) 0.99457(7) 0.0606(4) Uani d O C7 1 -0.2319(2) 0.3370(2) 0.84853(7) 0.0379(4) Uani d C C8 1 -0.2913(3) 0.2221(3) 0.79429(8) 0.0449(4) Uani d C C9 1 -0.4750(3) 0.2534(3) 0.75436(9) 0.0501(5) Uani d C C10 1 -0.6002(3) 0.3993(3) 0.76856(9) 0.0535(5) Uani d C C11 1 -0.5416(3) 0.5159(3) 0.82187(9) 0.0503(5) Uani d C C12 1 -0.3580(2) 0.4850(2) 0.86192(8) 0.0430(4) Uani d C C13 1 -0.0951(3) -0.0368(3) 0.90918(11) 0.0546(5) Uani d C H1 1 0.313(3) 0.543(3) 0.9714(10) 0.068(6) Uiso d H H5a 1 0.279(3) -0.012(3) 0.9457(10) 0.064(6) Uiso d H H5b 1 0.315(3) 0.091(3) 0.8780(11) 0.075(6) Uiso d H H8 1 -0.205(3) 0.120(3) 0.7836(9) 0.056(5) Uiso d H H9 1 -0.517(3) 0.169(3) 0.7169(10) 0.058(5) Uiso d H H10 1 -0.732(3) 0.422(3) 0.7414(10) 0.061(5) Uiso d H H11 1 -0.634(3) 0.621(3) 0.8325(10) 0.071(6) Uiso d H H12 1 -0.319(3) 0.566(3) 0.9009(9) 0.055(5) Uiso d H H13a 1 -0.100(3) -0.114(4) 0.8692(12) 0.086(7) Uiso d H H13b 1 -0.237(4) 0.003(4) 0.9147(14) 0.104(9) Uiso d H H13c 1 -0.041(3) -0.117(3) 0.9474(12) 0.080(7) Uiso d H 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 125.40(10) yes C6 N1 H1 118.3(12) no N2 N1 H1 114.4(12) no C3 N2 N1 114.50(10) yes N2 C3 N4 123.10(10) yes N2 C3 C7 116.30(10) yes N4 C3 C7 120.60(10) yes C3 N4 C5 117.00(10) yes C3 N4 C13 124.40(10) yes C5 N4 C13 118.5(2) yes N4 C5 C6 110.50(10) yes N4 C5 H5a 107.7(12) no C6 C5 H5a 109.1(12) no N4 C5 H5b 111.5(12) no C6 C5 H5b 108.5(13) no H5a C5 H5b 109.5(18) no O6 C6 N1 122.8(2) yes O6 C6 C5 122.1(2) yes N1 C6 C5 115.10(10) yes C3 C7 C8 121.10(10) yes C3 C7 C12 119.80(10) yes C8 C7 C12 119.1(2) no C7 C8 C9 120.5(2) no C7 C8 H8 120.6(11) no C9 C8 H8 118.9(11) no C8 C9 C10 119.9(2) no C8 C9 H9 119.5(11) no C10 C9 H9 120.6(11) no C9 C10 C11 120.1(2) no C9 C10 H10 121.1(12) no C11 C10 H10 118.8(12) no C10 C11 C12 120.2(2) no C10 C11 H11 120.0(12) no C12 C11 H11 119.8(12) no C7 C12 C11 120.2(2) no C7 C12 H12 119.9(11) no C11 C12 H12 119.9(11) no N4 C13 H13a 111.2(14) no N4 C13 H13b 110.7(15) no H13a C13 H13b 110.(2) no N4 C13 H13c 108.9(13) no H13a C13 H13c 108.7(18) no H13b C13 H13c 108.(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C6 1.332(2) yes N1 N2 1.405(2) yes N1 H1 0.97(2) no N2 C3 1.296(2) yes C3 N4 1.364(2) yes C3 C7 1.486(2) yes N4 C5 1.451(2) yes N4 C13 1.455(2) yes C5 C6 1.494(2) yes C5 H5a 0.96(2) no C5 H5b 1.04(2) no C6 O6 1.238(2) yes C7 C8 1.391(2) no C7 C12 1.390(2) no C8 C9 1.388(2) no C8 H8 0.97(2) no C9 C10 1.381(3) no C9 H9 0.98(2) no C10 C11 1.382(3) no C10 H10 0.98(2) no C11 C12 1.389(2) no C11 H11 1.01(2) no C12 H12 0.99(2) no C13 H13a 0.99(3) no C13 H13b 1.01(3) no C13 H13c 0.99(2) no 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 -6.5(3) yes N2 C3 N4 C5 -26.7(5) yes C3 N4 C5 C6 41.3(4) yes N4 C5 C6 N1 -24.6(4) yes C5 C6 N1 N2 -7.0(4) yes C6 N1 N2 C3 24.5(4) yes N2 C3 N4 C13 157.0(3) yes C7 C3 N4 C13 -24.5(5) yes N2 N1 C6 O6 172.9(3) yes N2 C3 C7 C12 -41.2(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21137993