#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/90/2009013.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_2009013 loop_ _publ_author_name 'Linden, Anthony' 'Moya Argilagos, Dally' 'Heimgartner, Heinz' 'Garc\'ia Trimi\~no, Mar\'ia I.' 'Mac\'ias Cabrera, Arturo' _publ_section_title ; `Push--pull' effects in nitroethenamines ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1692 _journal_page_last 1698 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C16 H20 N4 O3 S ' _chemical_formula_sum 'C16 H20 N4 O3 S' _chemical_formula_weight 348.42 _chemical_melting_point 447.8(3) _chemical_name_systematic ' N-cinnamoyl-3,3-bis(dimethylamino)-2-nitrothioacrylamide' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 108.930(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.9391(8) _cell_length_b 14.4523(13) _cell_length_c 10.7398(9) _cell_measurement_reflns_used 25 _cell_measurement_temperature 173.0(10) _cell_measurement_theta_max 19.0 _cell_measurement_theta_min 15.5 _cell_volume 1752.9(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 173.0(10) _diffrn_measured_fraction_theta_full 0.964 _diffrn_measured_fraction_theta_max 0.964 _diffrn_measurement_device_type 'Rigaku AFC-5R' _diffrn_measurement_method '\w/2\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Rigaku rotating anode generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_av_sigmaI/netI 0.091 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 5354 _diffrn_reflns_theta_full 30.0 _diffrn_reflns_theta_max 30 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% insignificant _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.472 _refine_diff_density_min -0.249 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 5107 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.120 _refine_ls_R_factor_gt 0.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.0973P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.140 _reflns_number_gt 3051 _reflns_number_total 5107 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file fg1546.cif _[local]_cod_data_source_block 2b _[local]_cod_cif_authors_sg_H-M 'P 21/c' _[local]_cod_chemical_formula_sum_orig 'C16 H20 N4 O3 S ' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '447.5-448' was changed to '447.8(3)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '447.5-448' was changed to '447.8(3)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1752.9(2) _cod_database_code 2009013 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S .91169(5) .61074(5) .07821(5) .03102(15) Uani d . 1 . . S O1 .95094(14) .59980(13) .51437(14) .0322(4) Uani d . 1 . . O O2 1.13434(13) .64297(12) .54911(14) .0328(4) Uani d . 1 . . O O3 .67444(14) .53242(14) .07644(15) .0422(5) Uani d . 1 . . O N1 .82205(14) .56343(13) .27155(17) .0228(4) Uani d . 1 . . N H1 .840(2) .560(2) .355(3) .043(8) Uiso d . 1 . . H N2 1.03352(15) .62288(13) .47047(16) .0229(4) Uani d . 1 . . N N3 1.14537(14) .75012(13) .31705(16) .0215(3) Uani d . 1 . . N N4 1.19165(14) .60043(13) .27263(16) .0224(4) Uani d . 1 . . N C1 .91323(16) .59872(14) .23329(19) .0199(4) Uani d . 1 . . C C2 1.01678(16) .62646(13) .33722(18) .0188(4) Uani d . 1 . . C C3 1.12158(16) .66079(14) .30580(18) .0188(4) Uani d . 1 . . C C4 .71102(17) .53102(15) .1957(2) .0228(4) Uani d . 1 . . C C5 .64440(17) .49040(15) .2772(2) .0233(4) Uani d . 1 . . C H5 .6759 .4934 .3704 .028 Uiso calc R 1 . . H C6 .54028(17) .44961(15) .2195(2) .0229(4) Uani d . 1 . . C H6 .5081 .4565 .1267 .028 Uiso calc R 1 . . H C7 .46934(17) .39539(14) .2822(2) .0219(4) Uani d . 1 . . C C8 .37090(18) .34795(15) .2005(2) .0256(4) Uani d . 1 . . C H8 .3502 .3540 .1076 .031 Uiso calc R 1 . . H C9 .30287(19) .29208(16) .2531(2) .0308(5) Uani d . 1 . . C H9 .2371 .2593 .1963 .037 Uiso calc R 1 . . H C10 .3307(2) .28411(18) .3877(3) .0361(6) Uani d . 1 . . C H10 .2839 .2462 .4237 .043 Uiso calc R 1 . . H C11 .4276(2) .3316(2) .4707(2) .0387(6) Uani d . 1 . . C H11 .4463 .3265 .5634 .046 Uiso calc R 1 . . H C12 .49703(19) .38652(17) .4189(2) .0304(5) Uani d . 1 . . C H12 .5636 .4182 .4763 .037 Uiso calc R 1 . . H C13 1.05432(19) .81778(16) .3213(2) .0284(5) Uani d . 1 . . C H131 .9766 .7968 .2640 .043 Uiso calc R 1 . . H H132 1.0726 .8781 .2908 .043 Uiso calc R 1 . . H H133 1.0532 .8234 .4118 .043 Uiso calc R 1 . . H C14 1.26580(18) .78734(16) .3470(2) .0294(5) Uani d . 1 . . C H141 1.3236 .7385 .3857 .044 Uiso calc R 1 . . H H142 1.2770 .8387 .4095 .044 Uiso calc R 1 . . H H143 1.2771 .8096 .2657 .044 Uiso calc R 1 . . H C15 1.2572(2) .62330(18) .1824(2) .0316(5) Uani d . 1 . . C H151 1.2331 .6846 .1441 .047 Uiso calc R 1 . . H H152 1.2400 .5771 .1119 .047 Uiso calc R 1 . . H H153 1.3423 .6235 .2308 .047 Uiso calc R 1 . . H C16 1.1807(2) .50097(16) .2917(2) .0304(5) Uani d . 1 . . C H161 1.1393 .4909 .3559 .046 Uiso calc R 1 . . H H162 1.2597 .4732 .3244 .046 Uiso calc R 1 . . H H163 1.1356 .4723 .2077 .046 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 .0222(2) .0528(4) .0181(2) -.0039(3) .00649(19) .0023(2) O1 .0310(8) .0470(10) .0234(7) -.0149(7) .0157(6) -.0052(7) O2 .0261(8) .0477(10) .0195(7) -.0107(7) .0004(6) .0009(7) O3 .0285(8) .0674(13) .0252(8) -.0202(9) .0011(7) .0061(8) N1 .0185(8) .0309(10) .0197(8) -.0034(7) .0072(7) .0014(7) N2 .0211(8) .0284(10) .0194(8) -.0042(7) .0067(7) .0000(7) N3 .0199(8) .0221(8) .0235(8) -.0018(7) .0083(7) .0020(7) N4 .0188(8) .0270(9) .0231(8) .0008(7) .0092(6) .0027(7) C1 .0167(8) .0221(10) .0212(9) .0002(8) .0063(7) .0012(8) C2 .0171(8) .0215(10) .0188(8) -.0018(7) .0072(7) .0003(8) C3 .0153(8) .0240(10) .0159(8) -.0013(7) .0034(7) .0035(8) C4 .0175(9) .0253(11) .0244(9) -.0012(8) .0054(8) .0015(8) C5 .0199(9) .0277(11) .0238(9) .0006(8) .0089(8) .0026(8) C6 .0207(9) .0248(11) .0230(9) -.0004(8) .0067(8) .0022(8) C7 .0178(8) .0210(10) .0270(10) .0012(8) .0071(7) .0028(8) C8 .0241(10) .0252(11) .0276(10) -.0012(9) .0085(8) -.0018(9) C9 .0247(10) .0241(11) .0407(13) -.0069(9) .0068(9) .0002(10) C10 .0270(11) .0366(14) .0442(14) -.0057(10) .0107(10) .0162(11) C11 .0307(12) .0530(17) .0300(11) -.0044(11) .0064(10) .0156(12) C12 .0219(10) .0378(13) .0283(11) -.0045(9) .0035(8) .0060(10) C13 .0320(11) .0255(11) .0296(11) .0034(9) .0126(9) .0031(9) C14 .0236(10) .0305(12) .0334(12) -.0078(9) .0082(9) .0014(10) C15 .0283(11) .0408(14) .0327(11) .0010(10) .0196(9) .0023(10) C16 .0284(11) .0263(11) .0392(12) .0038(9) .0147(10) .0021(10) 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 . 1.669(2) yes O1 N2 . 1.268(2) ? O2 N2 . 1.260(2) ? O3 C4 . 1.211(2) ? N1 C1 . 1.380(2) yes N1 C4 . 1.393(3) yes N1 H1 . .85(3) ? N2 C2 . 1.380(2) yes N3 C3 . 1.319(3) yes N3 C14 . 1.470(3) ? N3 C13 . 1.474(3) ? N4 C3 . 1.335(3) yes N4 C16 . 1.464(3) ? N4 C15 . 1.468(2) ? C1 C2 . 1.428(3) yes C2 C3 . 1.483(2) yes C4 C5 . 1.482(3) yes C5 C6 . 1.333(3) yes C5 H5 . .9500 ? C6 C7 . 1.467(3) ? C6 H6 . .9500 ? C7 C8 . 1.397(3) ? C7 C12 . 1.403(3) ? C8 C9 . 1.389(3) ? C8 H8 . .9500 ? C9 C10 . 1.379(3) ? C9 H9 . .9500 ? C10 C11 . 1.391(3) ? C10 H10 . .9500 ? C11 C12 . 1.388(3) ? C11 H11 . .9500 ? C12 H12 . .9500 ? C13 H131 . .9800 ? C13 H132 . .9800 ? C13 H133 . .9800 ? C14 H141 . .9800 ? C14 H142 . .9800 ? C14 H143 . .9800 ? C15 H151 . .9800 ? C15 H152 . .9800 ? C15 H153 . .9800 ? C16 H161 . .9800 ? C16 H162 . .9800 ? C16 H163 . .9800 ? 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 for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; S S 0.1246 0.1234 ; International Tables for Crystallography (1992). Vol.C, Tables 4.2.6.8 and 6.1.1.4 ; loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 4 1 1 4 0 -1 4 2 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 C4 130.02(18) yes C1 N1 H1 112.2(18) ? C4 N1 H1 117.8(18) ? O2 N2 O1 120.04(16) ? O2 N2 C2 118.16(16) ? O1 N2 C2 121.80(16) ? C3 N3 C14 123.00(17) ? C3 N3 C13 120.87(17) ? C14 N3 C13 115.43(18) ? C3 N4 C16 120.80(17) ? C3 N4 C15 122.95(18) ? C16 N4 C15 113.88(18) ? N1 C1 C2 115.95(17) yes N1 C1 S 125.54(15) yes C2 C1 S 118.50(14) ? N2 C2 C1 126.67(17) yes N2 C2 C3 113.54(16) ? C1 C2 C3 119.77(16) ? N3 C3 N4 121.95(17) yes N3 C3 C2 118.63(17) ? N4 C3 C2 119.36(18) ? O3 C4 N1 124.14(19) yes O3 C4 C5 123.53(19) ? N1 C4 C5 112.27(17) ? C6 C5 C4 119.96(19) ? C6 C5 H5 120.0 ? C4 C5 H5 120.0 ? C5 C6 C7 127.83(19) yes C5 C6 H6 116.1 ? C7 C6 H6 116.1 ? C8 C7 C12 118.50(19) ? C8 C7 C6 117.85(18) ? C12 C7 C6 123.62(18) yes C9 C8 C7 120.9(2) ? C9 C8 H8 119.6 ? C7 C8 H8 119.6 ? C10 C9 C8 120.1(2) ? C10 C9 H9 120.0 ? C8 C9 H9 120.0 ? C9 C10 C11 119.9(2) ? C9 C10 H10 120.1 ? C11 C10 H10 120.1 ? C12 C11 C10 120.4(2) ? C12 C11 H11 119.8 ? C10 C11 H11 119.8 ? C11 C12 C7 120.2(2) ? C11 C12 H12 119.9 ? C7 C12 H12 119.9 ? N3 C13 H131 109.5 ? N3 C13 H132 109.5 ? H131 C13 H132 109.5 ? N3 C13 H133 109.5 ? H131 C13 H133 109.5 ? H132 C13 H133 109.5 ? N3 C14 H141 109.5 ? N3 C14 H142 109.5 ? H141 C14 H142 109.5 ? N3 C14 H143 109.5 ? H141 C14 H143 109.5 ? H142 C14 H143 109.5 ? N4 C15 H151 109.5 ? N4 C15 H152 109.5 ? H151 C15 H152 109.5 ? N4 C15 H153 109.5 ? H151 C15 H153 109.5 ? H152 C15 H153 109.5 ? N4 C16 H161 109.5 ? N4 C16 H162 109.5 ? H161 C16 H162 109.5 ? N4 C16 H163 109.5 ? H161 C16 H163 109.5 ? H162 C16 H163 109.5 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O1 0.85(3) 1.88(3) 2.616(2) 144(3) 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 C4 N1 C1 C2 179.8(2) yes C4 N1 C1 S -0.5(3) ? O2 N2 C2 C1 174.14(19) ? O1 N2 C2 C1 -5.6(3) ? O2 N2 C2 C3 -4.1(3) yes O1 N2 C2 C3 176.24(18) ? N1 C1 C2 N2 -1.2(3) ? S C1 C2 N2 179.06(17) yes N1 C1 C2 C3 176.93(18) yes S C1 C2 C3 -2.8(3) ? C14 N3 C3 N4 -25.2(3) ? C13 N3 C3 N4 164.81(18) ? C14 N3 C3 C2 151.91(18) ? C13 N3 C3 C2 -18.1(3) yes C16 N4 C3 N3 164.92(19) ? C15 N4 C3 N3 -33.6(3) ? C16 N4 C3 C2 -12.1(3) yes C15 N4 C3 C2 149.33(19) ? N2 C2 C3 N3 -75.3(2) yes C1 C2 C3 N3 106.4(2) yes N2 C2 C3 N4 101.9(2) yes C1 C2 C3 N4 -76.5(2) yes C1 N1 C4 O3 -3.0(4) ? C1 N1 C4 C5 174.3(2) yes O3 C4 C5 C6 2.6(3) ? N1 C4 C5 C6 -174.8(2) yes C4 C5 C6 C7 171.3(2) yes C5 C6 C7 C8 -171.1(2) yes C5 C6 C7 C12 7.0(4) ? C12 C7 C8 C9 -1.0(3) ? C6 C7 C8 C9 177.2(2) ? C7 C8 C9 C10 1.2(3) ? C8 C9 C10 C11 -0.4(4) ? C9 C10 C11 C12 -0.5(4) ? C10 C11 C12 C7 0.7(4) ? C8 C7 C12 C11 0.0(3) ? C6 C7 C12 C11 -178.0(2) ? _cod_database_fobs_code 2009013 _journal_paper_doi 10.1107/S0108270199006861