#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/05/2010513.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_2010513 loop_ _publ_author_name 'Nesterov, Vladimir N.' 'Antipin, Mikhail Yu.' 'Timofeeva, Tatiana V.' 'Clark, Ronald D.' _publ_section_title trans,trans-2-Cyano-5-(4-methoxyphenyl)penta-2,4-dienethioamide _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 88 _journal_page_last 89 _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C13 H12 N2 O S' _chemical_formula_weight 244.31 _chemical_name_systematic ; ; _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 95.51(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.4590(13) _cell_length_b 15.662(3) _cell_length_c 12.276(3) _cell_measurement_reflns_used 24 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 12 _cell_measurement_theta_min 11 _cell_volume 1236.1(5) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1994)' _computing_molecular_graphics SHELXTL-Plus _computing_publication_material SHELXTL-Plus _computing_structure_refinement SHELXTL-Plus _computing_structure_solution SHELXTL-Plus _diffrn_ambient_temperature 295(2) _diffrn_measurement_device 'Enraf-Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .112 _diffrn_reflns_av_sigmaI/netI .0866 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 2922 _diffrn_reflns_theta_max 26.96 _diffrn_reflns_theta_min 2.11 _diffrn_standards_decay_% 5 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .246 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 512 _exptl_crystal_size_max .45 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .25 _refine_diff_density_max .32 _refine_diff_density_min -.30 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.098 _refine_ls_goodness_of_fit_ref 1.334 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 162 _refine_ls_number_reflns 2655 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.372 _refine_ls_restrained_S_obs 1.334 _refine_ls_R_factor_all .167 _refine_ls_R_factor_gt .076 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'calc w = 1/[\s^2^(Fo^2^)+(0.1213P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_wR_factor_all .306 _refine_ls_wR_factor_ref .201 _reflns_number_gt 1283 _reflns_number_total 2688 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1375.cif _[local]_cod_data_source_block (I) _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1236.1(4) _cod_database_code 2010513 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 S1 .0753(8) .0490(7) .0867(9) -.0128(6) .0372(7) -.0034(6) O1 .066(2) .060(2) .081(2) .007(2) .031(2) .004(2) N1 .079(3) .057(2) .107(3) -.003(2) .041(2) .013(2) N2 .065(2) .043(2) .071(3) -.002(2) .034(2) .004(2) C1 .048(2) .049(2) .047(2) -.003(2) .004(2) -.004(2) C2 .063(2) .044(2) .063(3) -.006(2) .018(2) .006(2) C3 .070(3) .043(2) .057(3) .005(2) .010(2) .000(2) C4 .052(2) .054(2) .046(2) .000(2) .008(2) .006(2) C5 .057(2) .044(2) .075(3) -.007(2) .013(2) .002(2) C6 .060(2) .043(2) .065(3) -.001(2) .011(2) -.003(2) C7 .058(2) .047(2) .054(3) -.006(2) .009(2) .004(2) C8 .058(2) .050(2) .051(2) .001(2) .010(2) .002(2) C9 .055(2) .048(2) .050(2) -.005(2) .008(2) .000(2) C10 .055(2) .040(2) .053(2) -.007(2) .009(2) .001(2) C11 .059(2) .039(2) .052(2) -.005(2) .009(2) -.001(2) C12 .062(3) .051(3) .067(3) .002(2) .022(2) .003(2) C13 .080(3) .067(3) .085(4) .007(3) .033(3) -.006(3) 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 S1 .1221(2) .74352(7) .15076(11) .0685(5) Uani d . 1 . S O1 1.3971(5) .5001(2) -.2771(3) .0676(9) Uani d . 1 . O N1 .6636(7) .9262(3) -.0180(4) .0787(13) Uani d . 1 . N N2 .2078(6) .9008(2) .1019(3) .0578(10) Uani d . 1 . N H1N .279(7) .943(3) .069(4) .080(16) Uiso d . 1 . H H2N .099(7) .913(3) .130(4) .062(14) Uiso d . 1 . H C1 .8939(6) .5876(3) -.1211(3) .0482(10) Uani d . 1 . C C2 .9184(6) .4997(3) -.1393(4) .0560(11) Uani d . 1 . C H2A .8214(6) .4617(3) -.1158(4) .067 Uiso calc R 1 . H C3 1.0828(7) .4683(3) -.1915(4) .0563(11) Uani d . 1 . C H3A 1.0948(7) .4099(3) -.2031(4) .068 Uiso calc R 1 . H C4 1.2280(6) .5231(3) -.2259(3) .0506(10) Uani d . 1 . C C5 1.2062(7) .6111(3) -.2093(4) .0580(11) Uani d . 1 . C H5A 1.3030(7) .6487(3) -.2336(4) .070 Uiso calc R 1 . H C6 1.0431(6) .6419(3) -.1573(3) .0557(11) Uani d . 1 . C H6A 1.0321(6) .7004(3) -.1461(3) .067 Uiso calc R 1 . H C7 .7203(6) .6166(3) -.0663(3) .0528(11) Uani d . 1 . C H7A .6301(6) .5749(3) -.0449(3) .063 Uiso calc R 1 . H C8 .6748(6) .6979(3) -.0428(3) .0529(10) Uani d . 1 . C H8A .7622(6) .7411(3) -.0632(3) .063 Uiso calc R 1 . H C9 .4982(7) .7207(3) .0120(3) .0508(10) Uani d . 1 . C H9A .4129(7) .6763(3) .0310(3) .061 Uiso calc R 1 . H C10 .4428(6) .8005(2) .0390(3) .0489(10) Uani d . 1 . C C11 .2559(6) .8197(2) .0960(3) .0496(10) Uani d . 1 . C C12 .5662(7) .8700(3) .0074(4) .0588(11) Uani d . 1 . C C13 1.4261(8) .4114(3) -.2968(5) .0757(14) Uani d . 1 . C H13A 1.5499(8) .4035(3) -.3331(5) .114 Uiso calc R 1 . H H13B 1.3084(8) .3897(3) -.3422(5) .114 Uiso calc R 1 . H H13C 1.4396(8) .3812(3) -.2284(5) .114 Uiso calc R 1 . H loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C11 . . 1.653(4) yes O1 C4 . . 1.361(5) yes O1 C13 . . 1.425(6) yes N1 C12 . . 1.143(6) yes N2 C11 . . 1.312(5) yes N2 H1N . . .92(5) yes N2 H2N . . .83(5) yes C1 C6 . . 1.390(6) no C1 C2 . . 1.407(6) no C1 C7 . . 1.435(6) yes C2 C3 . . 1.382(6) no C2 H2A . . .93 no C3 C4 . . 1.368(6) no C3 H3A . . .93 no C4 C5 . . 1.401(6) no C5 C6 . . 1.370(6) no C5 H5A . . .93 no C6 H6A . . .93 no C7 C8 . . 1.344(6) yes C7 H7A . . .93 no C8 C9 . . 1.424(6) yes C8 H8A . . .93 no C9 C10 . . 1.351(6) yes C9 H9A . . .93 no C10 C12 . . 1.425(6) yes C10 C11 . . 1.483(6) yes C13 H13A . . .96 no C13 H13B . . .96 no C13 H13C . . .96 no loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .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 O1 C13 117.5(4) yes C11 N2 H1N 123(3) yes C11 N2 H2N 117(3) yes H1N N2 H2N 120(4) yes C6 C1 C2 117.1(4) yes C6 C1 C7 123.6(4) yes C2 C1 C7 119.3(4) yes C3 C2 C1 121.7(4) no C3 C2 H2A 119.1(2) no C1 C2 H2A 119.1(2) no C4 C3 C2 120.0(4) no C4 C3 H3A 120.0(3) no C2 C3 H3A 120.0(2) no O1 C4 C3 125.5(4) yes O1 C4 C5 115.2(4) yes C3 C4 C5 119.4(4) no C6 C5 C4 120.5(4) no C6 C5 H5A 119.8(3) no C4 C5 H5A 119.8(3) no C5 C6 C1 121.4(4) no C5 C6 H6A 119.3(3) no C1 C6 H6A 119.3(2) no C8 C7 C1 126.6(4) yes C8 C7 H7A 116.7(3) no C1 C7 H7A 116.7(2) no C7 C8 C9 122.7(4) yes C7 C8 H8A 118.7(3) no C9 C8 H8A 118.7(3) no C10 C9 C8 126.2(4) yes C10 C9 H9A 116.9(2) no C8 C9 H9A 116.9(2) no C9 C10 C12 118.2(4) yes C9 C10 C11 123.4(4) yes C12 C10 C11 118.4(4) yes N2 C11 C10 115.5(4) yes N2 C11 S1 122.7(3) yes C10 C11 S1 121.8(3) yes N1 C12 C10 179.3(5) yes O1 C13 H13A 109.5(2) no O1 C13 H13B 109.5(3) no H13A C13 H13B 109.5 no O1 C13 H13C 109.5(3) no H13A C13 H13C 109.5 no H13B C13 H13C 109.5 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 N2 H1N N1 3_675 .92(5) 2.18(5) 3.042(5) 155(4) yes N2 H2N O1 4_476 .83(5) 2.27(5) 3.035(5) 153(4) 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 C6 C1 C2 C3 -.3(6) no C7 C1 C2 C3 -179.9(4) no C1 C2 C3 C4 .5(7) no C13 O1 C4 C3 .1(6) yes C13 O1 C4 C5 -179.6(4) yes C2 C3 C4 O1 179.4(4) no C2 C3 C4 C5 -.9(6) no O1 C4 C5 C6 -179.2(4) no C3 C4 C5 C6 1.1(6) no C4 C5 C6 C1 -.9(7) no C2 C1 C6 C5 .4(6) no C7 C1 C6 C5 -180.0(4) no C6 C1 C7 C8 .5(7) no C2 C1 C7 C8 -179.9(4) yes C1 C7 C8 C9 180.0(4) yes C7 C8 C9 C10 179.6(4) yes C8 C9 C10 C12 2.2(6) yes C8 C9 C10 C11 179.9(4) yes C9 C10 C11 N2 -170.5(4) yes C12 C10 C11 N2 7.1(6) yes C9 C10 C11 S1 11.0(6) yes C12 C10 C11 S1 -171.4(3) yes C9 C10 C12 N1 15E1(5) no C11 C10 C12 N1 -3E1(5) no _journal_paper_doi 10.1107/S0108270199012998