#------------------------------------------------------------------------------ #$Date: 2013-08-29 18:37:19 +0300 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008086.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_2008086 loop_ _publ_author_name 'Yuan-Fang Liu' 'Suchada Chantrapromma' 'S. Shanmuga Sundara Raj' 'Hoong-Kun Fun' 'Yin-Han Zhang' 'Fu-Xin Xie' 'Yu-Peng Tian' 'Shi-Sheng Ni' _publ_section_title ; 4-Amino-3-methyl-1,2,4-triazole-5-thione derivative of p-nitrophenylaldehyde ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 93 _journal_page_last 94 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C10 H9 N5 O2 S' _chemical_formula_weight 263.28 _chemical_melting_point 223.6 _chemical_name_systematic ; 3-Methyl-4-amino-5-mercapto-1,2,4-triazole derivative of p-nitro phenylaldehyde ; _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 _cell_angle_alpha 90.00 _cell_angle_beta 113.881(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 13.3256(5) _cell_length_b 6.9775(3) _cell_length_c 13.9402(6) _cell_measurement_reflns_used 2120 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.22 _cell_measurement_theta_min 2.74 _cell_volume 1185.19(9) _computing_cell_refinement 'SAINT (Siemens, 1996b)' _computing_data_collection 'SMART (Siemens, 1996a)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device ; Siemens SMART CCD area-detector diffractometer ; _diffrn_measurement_method '\w scans' _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 0.0726 _diffrn_reflns_av_sigmaI/netI 0.1049 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 8482 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_theta_min 2.74 _exptl_absorpt_coefficient_mu 0.275 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_correction_T_min 0.842 _exptl_absorpt_correction_type 'empirical (SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.220 _refine_diff_density_min -0.285 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.036 _refine_ls_goodness_of_fit_obs 1.230 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3390 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_obs 1.230 _refine_ls_R_factor_all 0.1853 _refine_ls_R_factor_obs 0.0773 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.2428P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all 0.1687 _refine_ls_wR_factor_obs 0.1301 _reflns_number_observed 1525 _reflns_number_total 3390 _reflns_observed_criterion >2sigma(I) _[local]_cod_data_source_file ha1234.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 1185.18(8) _cod_database_code 2008086 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_label _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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol S 0.94227(7) 0.8384(2) 0.07431(7) 0.0623(4) Uani d . 1 . S O1 1.7077(2) 0.8216(6) 0.2939(3) 0.1178(14) Uani d . 1 . O O2 1.6478(2) 0.9158(5) 0.1353(3) 0.0999(11) Uani d . 1 . O N1 0.9163(2) 0.8762(4) 0.2547(2) 0.0527(8) Uani d . 1 . N N2 0.9702(2) 0.9020(4) 0.3611(2) 0.0550(8) Uani d . 1 . N N3 1.0839(2) 0.8893(3) 0.2825(2) 0.0376(6) Uani d . 1 . N N4 1.1893(2) 0.8847(4) 0.2850(2) 0.0393(6) Uani d . 1 . N N5 1.6340(3) 0.8725(5) 0.2134(3) 0.0716(10) Uani d . 1 . N C1 0.9808(2) 0.8691(4) 0.2018(2) 0.0424(8) Uani d . 1 . C C2 1.0734(2) 0.9079(5) 0.3770(2) 0.0426(8) Uani d . 1 . C C3 1.1660(3) 0.9332(8) 0.4786(3) 0.0598(11) Uani d . 1 . C C4 1.2024(2) 0.9014(5) 0.2008(3) 0.0408(8) Uani d . 1 . C C5 1.3152(2) 0.8959(4) 0.2061(2) 0.0373(7) Uani d . 1 . C C6 1.3314(3) 0.9180(5) 0.1145(3) 0.0483(9) Uani d . 1 . C C7 1.4354(3) 0.9110(5) 0.1159(3) 0.0548(10) Uani d . 1 . C C8 1.5220(2) 0.8815(5) 0.2103(3) 0.0498(9) Uani d . 1 . C C9 1.5095(3) 0.8597(5) 0.3027(3) 0.0531(9) Uani d . 1 . C C10 1.4049(2) 0.8665(5) 0.3005(3) 0.0457(8) Uani d . 1 . C H10 1.393(3) 0.853(4) 0.365(3) 0.054(9) Uiso d . 1 . H H4 1.146(3) 0.923(4) 0.136(3) 0.055(10) Uiso d . 1 . H H6 1.271(3) 0.928(4) 0.051(2) 0.049(9) Uiso d . 1 . H H3C 1.142(4) 0.964(7) 0.533(4) 0.115(17) Uiso d . 1 . H H7 1.446(3) 0.921(5) 0.054(3) 0.074(12) Uiso d . 1 . H H3B 1.214(4) 1.037(7) 0.479(3) 0.098(16) Uiso d . 1 . H H3A 1.214(4) 0.825(7) 0.498(4) 0.108(17) Uiso d . 1 . H H9 1.563(3) 0.834(5) 0.363(3) 0.066(12) Uiso d . 1 . H H1N1 0.844(3) 0.875(5) 0.228(3) 0.076(12) Uiso d . 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 S 0.0369(5) 0.0974(8) 0.0485(5) -0.0058(5) 0.0130(4) 0.0019(5) O1 0.0295(14) 0.189(4) 0.132(3) 0.005(2) 0.030(2) -0.015(3) O2 0.070(2) 0.132(3) 0.137(3) -0.016(2) 0.082(2) -0.021(2) N1 0.0261(13) 0.076(2) 0.063(2) 0.0001(14) 0.0245(14) -0.002(2) N2 0.042(2) 0.071(2) 0.066(2) 0.0020(14) 0.037(2) -0.002(2) N3 0.0229(11) 0.051(2) 0.0456(15) 0.0030(11) 0.0210(11) 0.0049(12) N4 0.0267(12) 0.050(2) 0.048(2) 0.0008(11) 0.0222(12) 0.0051(12) N5 0.040(2) 0.077(3) 0.113(3) -0.013(2) 0.046(2) -0.030(2) C1 0.0245(14) 0.050(2) 0.056(2) 0.0016(14) 0.0199(14) 0.007(2) C2 0.038(2) 0.052(2) 0.046(2) 0.0061(14) 0.027(2) 0.005(2) C3 0.050(2) 0.086(3) 0.049(2) 0.007(2) 0.025(2) 0.002(2) C4 0.027(2) 0.050(2) 0.046(2) 0.0013(14) 0.017(2) 0.008(2) C5 0.0304(15) 0.040(2) 0.048(2) 0.0001(13) 0.0232(15) 0.0011(14) C6 0.035(2) 0.065(2) 0.049(2) 0.000(2) 0.022(2) 0.005(2) C7 0.046(2) 0.071(3) 0.063(2) -0.002(2) 0.039(2) 0.001(2) C8 0.031(2) 0.054(2) 0.077(3) -0.0045(14) 0.034(2) -0.014(2) C9 0.029(2) 0.066(3) 0.064(2) 0.000(2) 0.018(2) -0.005(2) C10 0.037(2) 0.058(2) 0.047(2) 0.003(2) 0.022(2) 0.003(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S C1 . 1.653(3) yes O1 N5 . 1.207(4) yes O2 N5 . 1.212(4) yes N1 C1 . 1.341(4) yes N1 N2 . 1.373(4) yes N2 C2 . 1.302(4) yes N3 C1 . 1.386(3) yes N3 C2 . 1.387(4) yes N3 N4 . 1.391(3) yes N4 C4 . 1.261(4) yes N5 C8 . 1.477(4) yes C2 C3 . 1.464(5) ? C4 C5 . 1.475(4) ? C5 C6 . 1.387(4) ? C5 C10 . 1.389(4) ? C6 C7 . 1.379(4) ? C7 C8 . 1.370(5) ? C8 C9 . 1.373(5) ? C9 C10 . 1.382(4) ? 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' S S 0.1246 0.1234 '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 C1 N1 N2 115.3(3) ? C2 N2 N1 104.1(3) ? C1 N3 C2 109.4(2) ? C1 N3 N4 132.7(2) yes C2 N3 N4 117.8(2) ? C4 N4 N3 119.5(2) yes O1 N5 O2 123.1(3) yes O1 N5 C8 118.1(4) yes O2 N5 C8 118.8(4) yes N1 C1 N3 101.3(3) ? N1 C1 S 127.4(2) yes N3 C1 S 131.3(2) ? N2 C2 N3 110.0(3) ? N2 C2 C3 125.9(3) yes N3 C2 C3 124.1(3) ? N4 C4 C5 118.2(3) yes C6 C5 C10 119.6(3) ? C6 C5 C4 119.0(3) ? C10 C5 C4 121.4(3) ? C7 C6 C5 120.9(3) ? C8 C7 C6 118.0(3) ? C7 C8 C9 122.8(3) ? C7 C8 N5 118.9(3) yes C9 C8 N5 118.3(3) ? C8 C9 C10 118.7(3) ? C9 C10 C5 120.0(3) ? 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 C4 H4 S 1_555 0.93(3) 2.56(3) 3.220(3) 129(3) no C9 H9 O1 1_555 0.87(3) 2.48(5) 2.706(5) 96(3) no N1 H1N1 O1 1_455 0.88(4) 2.38(5) 3.066(5) 136(4) yes N1 H1N1 O2 1_455 0.88(4) 2.42(4) 3.290(4) 170(4) yes _cod_database_fobs_code 2008086