#------------------------------------------------------------------------------ #$Date: 2017-10-13 07:09:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/44/2204447.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_2204447 loop_ _publ_author_name 'Elgemeie, Galal H.' 'Jones, Peter G.' _publ_section_title 6-Amino-4-(methylsulfanyl)-2-oxo-1-tolyl-1,2-dihydropyridine-3,5-dicarbonitrile _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2107 _journal_page_last o2109 _journal_paper_doi 10.1107/S1600536804026285 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C15 H12 N4 O S' _chemical_formula_moiety 'C15 H12 N4 O S' _chemical_formula_sum 'C15 H12 N4 O S' _chemical_formula_weight 296.35 _chemical_name_systematic 6-Amino-4-(methylsulfanyl)-2-oxo-1-tolyl-1,2-dihydropyridine-3,5-dicarbonitrile _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 100.364(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.5598(6) _cell_length_b 9.6111(5) _cell_length_c 17.9319(9) _cell_measurement_reflns_used 63 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 24.984 _cell_measurement_theta_min 10.169 _cell_volume 1451.17(15) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Fait, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics 'XP (Siemens, 1994)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \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 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 4858 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.13 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 247 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.227 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale brown' _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_description tablet _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.191 _refine_diff_density_min -0.322 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2547 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0328 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.2627P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0856 _refine_ls_wR_factor_ref 0.0890 _reflns_number_gt 2093 _reflns_number_total 2547 _reflns_threshold_expression I>2\s(I) _cod_data_source_file bt6546.cif _cod_data_source_block 3 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204447 _cod_database_fobs_code 2204447 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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S 0.10726(5) 0.35049(5) 0.07426(3) 0.02963(15) Uani d . 1 S O 0.55141(13) 0.47526(12) 0.29111(6) 0.0264(3) Uani d . 1 O N1 0.59844(15) 0.29122(13) 0.21779(7) 0.0180(3) Uani d . 1 N N2 0.65562(17) 0.10899(15) 0.14293(8) 0.0224(3) Uani d . 1 N H01 0.743(3) 0.088(2) 0.1751(11) 0.035(5) Uiso d . 1 H H02 0.633(2) 0.058(2) 0.1053(12) 0.029(5) Uiso d . 1 H N3 0.33448(18) 0.06037(16) -0.00415(8) 0.0329(4) Uani d . 1 N N4 0.16381(18) 0.59946(17) 0.23012(9) 0.0341(4) Uani d . 1 N C2 0.55445(18) 0.20516(16) 0.15681(8) 0.0187(3) Uani d . 1 C C3 0.40418(18) 0.22419(16) 0.11013(8) 0.0195(3) Uani d . 1 C C4 0.29899(18) 0.32588(16) 0.12832(9) 0.0202(3) Uani d . 1 C C5 0.34828(18) 0.41389(16) 0.18910(9) 0.0199(3) Uani d . 1 C C6 0.50231(18) 0.40126(16) 0.23643(9) 0.0197(3) Uani d . 1 C C7 0.0237(2) 0.1772(2) 0.06804(13) 0.0429(5) Uani d . 1 C H7A 0.0521 0.1289 0.0242 0.051 Uiso calc R 1 H H7B -0.0921 0.1832 0.0622 0.051 Uiso calc R 1 H H7C 0.0660 0.1255 0.1144 0.051 Uiso calc R 1 H C8 0.36328(18) 0.13432(17) 0.04670(9) 0.0220(4) Uani d . 1 C C9 0.24559(19) 0.51706(17) 0.21151(9) 0.0232(4) Uani d . 1 C C11 0.74182(18) 0.26165(16) 0.27240(9) 0.0198(3) Uani d . 1 C C12 0.88601(19) 0.31787(17) 0.26338(10) 0.0248(4) Uani d . 1 C H12 0.8939 0.3735 0.2204 0.030 Uiso calc R 1 H C13 1.0191(2) 0.29140(18) 0.31843(10) 0.0295(4) Uani d . 1 C H13 1.1187 0.3293 0.3126 0.035 Uiso calc R 1 H C14 1.0100(2) 0.21113(18) 0.38162(10) 0.0290(4) Uani d . 1 C C15 0.8632(2) 0.15411(19) 0.38821(10) 0.0309(4) Uani d . 1 C H15 0.8551 0.0970 0.4306 0.037 Uiso calc R 1 H C16 0.7294(2) 0.17927(18) 0.33422(9) 0.0261(4) Uani d . 1 C H16 0.6300 0.1404 0.3395 0.031 Uiso calc R 1 H C17 1.1532(2) 0.1908(2) 0.44329(11) 0.0422(5) Uani d . 1 C H17A 1.2501 0.1977 0.4215 0.051 Uiso calc R 1 H H17B 1.1481 0.0987 0.4663 0.051 Uiso calc R 1 H H17C 1.1545 0.2627 0.4821 0.051 Uiso calc R 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 0.0191(2) 0.0313(3) 0.0344(3) 0.00510(18) -0.00605(17) -0.00263(19) O 0.0214(6) 0.0262(6) 0.0301(6) -0.0002(5) 0.0006(5) -0.0102(5) N1 0.0151(6) 0.0185(7) 0.0197(6) 0.0002(5) 0.0012(5) -0.0021(5) N2 0.0197(7) 0.0249(8) 0.0206(7) 0.0053(6) -0.0015(6) -0.0046(6) N3 0.0294(8) 0.0369(9) 0.0294(8) 0.0057(7) -0.0026(6) -0.0094(7) N4 0.0264(8) 0.0354(9) 0.0404(9) 0.0063(7) 0.0057(7) -0.0091(7) C2 0.0193(8) 0.0178(8) 0.0194(8) -0.0016(6) 0.0049(6) 0.0028(6) C3 0.0183(8) 0.0204(8) 0.0191(8) 0.0001(6) 0.0018(6) -0.0014(6) C4 0.0171(8) 0.0214(8) 0.0216(8) -0.0015(6) 0.0025(6) 0.0033(6) C5 0.0174(8) 0.0179(8) 0.0248(8) 0.0016(6) 0.0049(6) 0.0004(6) C6 0.0183(8) 0.0185(8) 0.0229(8) -0.0015(6) 0.0051(6) -0.0006(7) C7 0.0205(9) 0.0447(12) 0.0601(13) -0.0081(8) -0.0017(9) 0.0054(10) C8 0.0172(8) 0.0249(9) 0.0227(8) 0.0041(7) 0.0008(6) 0.0017(7) C9 0.0176(8) 0.0249(9) 0.0260(8) -0.0019(7) 0.0009(6) -0.0018(7) C11 0.0168(8) 0.0189(8) 0.0224(8) 0.0017(6) 0.0003(6) -0.0048(6) C12 0.0202(8) 0.0244(8) 0.0297(9) 0.0003(7) 0.0041(7) -0.0006(7) C13 0.0157(8) 0.0290(9) 0.0421(10) -0.0008(7) 0.0004(7) -0.0071(8) C14 0.0243(9) 0.0288(9) 0.0302(9) 0.0068(7) -0.0052(7) -0.0092(8) C15 0.0344(10) 0.0328(10) 0.0232(9) 0.0029(8) -0.0008(7) 0.0018(7) C16 0.0220(9) 0.0298(9) 0.0259(9) -0.0026(7) 0.0023(7) -0.0001(7) C17 0.0338(11) 0.0487(12) 0.0375(11) 0.0104(9) -0.0110(9) -0.0104(9) 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 C4 S C7 103.21(8) y C2 N1 C6 123.48(13) ? C2 N1 C11 119.84(12) ? C6 N1 C11 116.29(12) ? C2 N2 H01 123.1(13) ? C2 N2 H02 119.8(13) ? H01 N2 H02 116.6(19) ? N2 C2 N1 118.56(14) ? N2 C2 C3 122.43(14) ? N1 C2 C3 119.00(14) ? C4 C3 C2 120.30(14) ? C4 C3 C8 122.16(14) ? C2 C3 C8 117.51(14) ? C5 C4 C3 119.35(14) ? C5 C4 S 118.16(12) ? C3 C4 S 122.45(12) ? C4 C5 C9 121.96(14) ? C4 C5 C6 122.00(14) ? C9 C5 C6 115.92(14) ? O C6 N1 119.54(14) ? O C6 C5 124.75(14) ? N1 C6 C5 115.68(13) ? S C7 H7A 109.5 ? S C7 H7B 109.5 ? H7A C7 H7B 109.5 ? S C7 H7C 109.5 ? H7A C7 H7C 109.5 ? H7B C7 H7C 109.5 ? N3 C8 C3 178.11(17) ? N4 C9 C5 179.40(18) ? C16 C11 C12 121.11(15) ? C16 C11 N1 118.35(14) ? C12 C11 N1 120.52(14) ? C11 C12 C13 118.68(16) ? C11 C12 H12 120.7 ? C13 C12 H12 120.7 ? C14 C13 C12 121.57(16) ? C14 C13 H13 119.2 ? C12 C13 H13 119.2 ? C13 C14 C15 118.19(15) ? C13 C14 C17 120.94(17) ? C15 C14 C17 120.83(17) ? C16 C15 C14 121.17(17) ? C16 C15 H15 119.4 ? C14 C15 H15 119.4 ? C15 C16 C11 119.26(16) ? C15 C16 H16 120.4 ? C11 C16 H16 120.4 ? C14 C17 H17A 109.5 ? C14 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? C14 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S C4 1.7654(16) y S C7 1.808(2) y O C6 1.2230(19) ? N1 C2 1.369(2) y N1 C6 1.416(2) y N1 C11 1.454(2) y N2 C2 1.321(2) y N2 H01 0.88(2) ? N2 H02 0.83(2) ? N3 C8 1.147(2) ? N4 C9 1.146(2) ? C2 C3 1.415(2) ? C3 C4 1.406(2) ? C3 C8 1.421(2) ? C4 C5 1.384(2) ? C5 C9 1.430(2) ? C5 C6 1.439(2) ? C7 H7A 0.9800 ? C7 H7B 0.9800 ? C7 H7C 0.9800 ? C11 C16 1.382(2) ? C11 C12 1.383(2) ? C12 C13 1.390(2) ? C12 H12 0.9500 ? C13 C14 1.385(3) ? C13 H13 0.9500 ? C14 C15 1.395(3) ? C14 C17 1.509(2) ? C15 C16 1.381(2) ? C15 H15 0.9500 ? C16 H16 0.9500 ? C17 H17A 0.9800 ? C17 H17B 0.9800 ? C17 H17C 0.9800 ? 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 N2 H01 O 2_645 0.88(2) 2.06(2) 2.8763(18) 153.1(18) N2 H02 N3 3_655 0.83(2) 2.20(2) 2.988(2) 158.4(18) C7 H7C O 2_545 0.98 2.56 3.338(2) 136 C16 H16 N4 2_545 0.95 2.63 3.442(2) 144 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 C6 N1 C2 N2 177.51(14) ? C11 N1 C2 N2 -9.9(2) ? C6 N1 C2 C3 -1.2(2) ? C11 N1 C2 C3 171.41(13) ? N2 C2 C3 C4 178.46(14) ? N1 C2 C3 C4 -2.9(2) ? N2 C2 C3 C8 0.5(2) ? N1 C2 C3 C8 179.12(14) ? C2 C3 C4 C5 4.7(2) ? C8 C3 C4 C5 -177.45(15) ? C2 C3 C4 S -177.71(11) ? C8 C3 C4 S 0.2(2) ? C7 S C4 C5 -131.15(14) ? C7 S C4 C3 51.21(16) y C3 C4 C5 C9 -178.47(15) ? S C4 C5 C9 3.8(2) ? C3 C4 C5 C6 -2.5(2) ? S C4 C5 C6 179.80(12) ? C2 N1 C6 O -178.64(14) ? C11 N1 C6 O 8.5(2) ? C2 N1 C6 C5 3.2(2) ? C11 N1 C6 C5 -169.59(13) ? C4 C5 C6 O -179.37(15) ? C9 C5 C6 O -3.2(2) ? C4 C5 C6 N1 -1.3(2) ? C9 C5 C6 N1 174.85(13) ? C2 N1 C11 C16 -90.64(18) ? C6 N1 C11 C16 82.46(18) ? C2 N1 C11 C12 90.99(18) ? C6 N1 C11 C12 -95.91(17) ? C16 C11 C12 C13 -0.8(2) ? N1 C11 C12 C13 177.53(14) ? C11 C12 C13 C14 -0.3(2) ? C12 C13 C14 C15 1.4(3) ? C12 C13 C14 C17 -176.12(16) ? C13 C14 C15 C16 -1.5(3) ? C17 C14 C15 C16 176.04(16) ? C14 C15 C16 C11 0.4(3) ? C12 C11 C16 C15 0.7(2) ? N1 C11 C16 C15 -177.65(15) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 347570