#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2203578.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_2203578 _space_group_IT_number 14 _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _[local]_cod_cif_authors_sg_H-M 'P 21/c' loop_ _publ_author_name 'Sema \"Ozt\"urk' 'Mehmet Akkurt' 'Ahmet Cans\?iz' 'Metin Kopar\?ir' 'Mehmet \,Sekerci' 'Frank W. Heinemann' _publ_section_title ; 2-Amino-5-phenyl-1,3,4-thiadiazole at 110 K ; _journal_issue 5 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o820 _journal_page_last o821 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H7 N3 S' _chemical_formula_moiety 'C8 H7 N3 S' _chemical_formula_sum 'C8 H7 N3 S' _chemical_formula_weight 177.24 _chemical_name_systematic ; 5-Phenyl-1,3,4-thiadiazol-2-amine ; _symmetry_cell_setting Monoclinic _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 117.965(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.604(5) _cell_length_b 7.922(5) _cell_length_c 11.116(5) _cell_measurement_reflns_used 73 _cell_measurement_temperature 100 _cell_measurement_theta_max 20 _cell_measurement_theta_min 6 _cell_volume 824.8(7) _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_data_collection 'COLLECT (Nonius, 1999)' _computing_data_reduction EVALCCD _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'Bruker--Nonius KappaCCD' _diffrn_measurement_method '\f and \w-scans (per frame) with 2.0\% and 40 sec per frame' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 23236 _diffrn_reflns_reduction_process ' ?' _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.00 _diffrn_reflns_theta_min 3.67 _exptl_absorpt_coefficient_mu 0.333 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_correction_T_min 0.887 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2002)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description plate _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.355 _refine_diff_density_min -0.270 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 117 _refine_ls_number_reflns 2176 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0350 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0346P)^2^+0.3514P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.0781 _reflns_number_gt 1699 _reflns_number_total 2176 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6296.cif loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 0.18079(4) -0.10639(5) 0.44739(3) 0.01590(10) Uani . . 1.000 S N1 0.04302(16) -0.40491(18) 0.36188(14) 0.0236(4) Uani . . 1.000 N N2 0.08289(13) -0.29552(16) 0.57333(12) 0.0175(3) Uani . . 1.000 N N3 0.14372(13) -0.15689(16) 0.65628(12) 0.0167(3) Uani . . 1.000 N C1 0.09361(15) -0.28781(19) 0.45989(14) 0.0161(4) Uani . . 1.000 C C2 0.19835(15) -0.04771(19) 0.60647(14) 0.0148(4) Uani . . 1.000 C C3 0.27254(15) 0.10710(19) 0.67702(15) 0.0163(4) Uani . . 1.000 C C4 0.34781(16) 0.1101(2) 0.81950(15) 0.0208(4) Uani . . 1.000 C C5 0.42189(18) 0.2539(2) 0.88646(17) 0.0249(5) Uani . . 1.000 C C6 0.42129(17) 0.3961(2) 0.81354(17) 0.0250(5) Uani . . 1.000 C C7 0.34557(17) 0.3948(2) 0.67228(17) 0.0245(5) Uani . . 1.000 C C8 0.27197(16) 0.2513(2) 0.60402(16) 0.0203(4) Uani . . 1.000 C H1A 0.064(2) -0.396(2) 0.296(2) 0.028(5) Uiso . . 1.000 H H1B 0.003(2) -0.492(3) 0.374(2) 0.037(6) Uiso . . 1.000 H H4 0.34810 0.01550 0.86920 0.0250 Uiso calc R 1.000 H H5 0.47240 0.25500 0.98110 0.0300 Uiso calc R 1.000 H H6 0.47150 0.49200 0.85910 0.0300 Uiso calc R 1.000 H H7 0.34420 0.49050 0.62330 0.0290 Uiso calc R 1.000 H H8 0.22200 0.25080 0.50940 0.0240 Uiso calc R 1.000 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 S1 0.0200(2) 0.0189(2) 0.0127(2) -0.0038(2) 0.01090(10) -0.0010(2) N1 0.0349(8) 0.0267(7) 0.0187(7) -0.0142(6) 0.0206(6) -0.0087(6) N2 0.0239(6) 0.0196(6) 0.0143(6) -0.0057(5) 0.0133(5) -0.0041(5) N3 0.0195(6) 0.0189(6) 0.0150(6) -0.0029(5) 0.0108(5) -0.0036(5) C1 0.0170(7) 0.0194(7) 0.0150(7) -0.0021(6) 0.0102(6) -0.0002(6) C2 0.0162(7) 0.0192(7) 0.0116(6) 0.0009(6) 0.0088(6) -0.0005(6) C3 0.0155(7) 0.0188(7) 0.0188(7) 0.0002(6) 0.0116(6) -0.0021(6) C4 0.0251(8) 0.0225(8) 0.0190(7) -0.0012(6) 0.0138(6) -0.0019(6) C5 0.0266(8) 0.0300(9) 0.0211(8) -0.0060(7) 0.0137(7) -0.0103(7) C6 0.0253(8) 0.0227(8) 0.0336(9) -0.0079(7) 0.0192(7) -0.0118(7) C7 0.0241(8) 0.0199(8) 0.0352(9) -0.0009(6) 0.0186(7) 0.0012(7) C8 0.0195(8) 0.0221(8) 0.0211(7) 0.0004(6) 0.0110(6) 0.0011(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 C1 1.749(2) yes S1 C2 1.7518(18) yes N1 C1 1.337(2) yes N2 N3 1.384(2) yes N2 C1 1.320(2) yes N3 C2 1.300(2) yes N1 H1A 0.86(2) no N1 H1B 0.85(2) no C2 C3 1.470(2) no C3 C8 1.400(2) no C3 C4 1.400(2) no C4 C5 1.386(2) no C5 C6 1.386(2) no C6 C7 1.389(3) no C7 C8 1.386(2) no C4 H4 0.9302 no C5 H5 0.9302 no C6 H6 0.9296 no C7 H7 0.9295 no C8 H8 0.9297 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag S1 N3 2.562(2) . no S1 N1 3.514(3) 2_555 no S1 H8 2.8966 . no N1 S1 3.514(3) 2_545 no N1 N2 2.972(3) 3_546 no N1 N3 2.982(3) 4_544 no N2 S1 2.578(2) . no N2 N1 2.972(3) 3_546 no N2 C8 3.348(3) 3_556 no N3 N1 2.982(3) 4_545 no N3 S1 2.562(2) . no N2 H1B 2.12(2) 3_546 no N2 H8 2.9386 3_556 no N3 H4 2.7117 . no N3 H1A 2.13(2) 4_545 no C5 C8 3.462(3) 4_555 no C8 C5 3.462(3) 4_554 no C8 N2 3.348(3) 3_556 no C1 H1B 3.05(2) 3_546 no C1 H7 2.9863 1_545 no C2 H1A 3.08(2) 4_545 no C3 H6 3.0629 2_646 no C5 H8 3.0131 4_555 no C8 H5 3.0183 4_554 no H1A N3 2.13(2) 4_544 no H1A C2 3.08(2) 4_544 no H1B N2 2.12(2) 3_546 no H1B C1 3.05(2) 3_546 no H4 N3 2.7117 . no H5 H6 2.5564 3_667 no H5 C8 3.0183 4_555 no H6 C3 3.0629 2_656 no H6 H5 2.5564 3_667 no H7 C1 2.9863 1_565 no H8 S1 2.8966 . no H8 N2 2.9386 3_556 no H8 C5 3.0131 4_554 no 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 S1 C2 87.01(7) yes N3 N2 C1 112.21(13) yes N2 N3 C2 113.94(12) yes C1 N1 H1B 118.1(14) no H1A N1 H1B 123.1(18) no C1 N1 H1A 118.1(12) no N1 C1 N2 124.42(15) yes S1 C1 N2 113.55(11) yes S1 C1 N1 122.04(12) yes S1 C2 N3 113.30(11) yes S1 C2 C3 122.48(12) yes N3 C2 C3 124.18(13) yes C2 C3 C4 119.76(14) no C2 C3 C8 121.07(13) no C4 C3 C8 119.15(14) no C3 C4 C5 120.03(15) no C4 C5 C6 120.53(15) no C5 C6 C7 119.80(15) no C6 C7 C8 120.24(15) no C3 C8 C7 120.25(14) no C3 C4 H4 119.97 no C5 C4 H4 120.01 no C4 C5 H5 119.73 no C6 C5 H5 119.74 no C5 C6 H6 120.08 no C7 C6 H6 120.12 no C6 C7 H7 119.89 no C8 C7 H7 119.87 no C3 C8 H8 119.84 no C7 C8 H8 119.91 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 C1 S1 C2 C3 178.12(15) no C2 S1 C1 N1 179.50(15) no C2 S1 C1 N2 -0.13(13) no C1 S1 C2 N3 0.23(13) no C1 N2 N3 C2 0.2(2) no N3 N2 C1 N1 -179.61(16) no N3 N2 C1 S1 0.02(17) no N2 N3 C2 S1 -0.27(18) no N2 N3 C2 C3 -178.12(15) no S1 C2 C3 C8 31.6(2) no N3 C2 C3 C4 30.7(3) no N3 C2 C3 C8 -150.73(17) no S1 C2 C3 C4 -146.99(14) no C2 C3 C4 C5 177.87(17) no C8 C3 C4 C5 -0.8(3) no C2 C3 C8 C7 -178.37(17) no C4 C3 C8 C7 0.2(3) no C3 C4 C5 C6 0.6(3) no C4 C5 C6 C7 0.2(3) no C5 C6 C7 C8 -0.7(3) no C6 C7 C8 C3 0.5(3) no 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 N1 H1A N3 4_544 0.86(2) 2.13(2) 2.982(3) 169.9(17) yes N1 H1B N2 3_546 0.85(2) 2.12(2) 2.972(3) 173.9(18) yes _cod_database_code 2203578