#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2009012.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_2009012 loop_ _publ_author_name 'Linden, A.' 'Moya Argilagos, D.' 'Heimgartner, H.' 'Garc\'ia Trimi\~no, M. I.' 'Mac\'ias Cabrera, A.' _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 'C12 H14 N4 O3 S ' _chemical_formula_sum 'C12 H14 N4 O3 S' _chemical_formula_weight 294.34 _chemical_melting_point 449.35(5) _chemical_name_systematic ' N-benzoyl-3,3-bis(methylamino)-2-nitrothioacrylamide' _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.7761(16) _cell_length_b 17.172(2) _cell_length_c 6.825(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 173.0(10) _cell_measurement_theta_max 20.0 _cell_measurement_theta_min 18.5 _cell_volume 1380.1(8) _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 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.020 _diffrn_reflns_av_sigmaI/netI 0.032 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 4197 _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 0.248 _exptl_absorpt_correction_type none _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_meas 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 616 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.28 _refine_diff_density_max 0.364 _refine_diff_density_min -0.181 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.28(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 196 _refine_ls_number_reflns 3413 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_gt 0.033 _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^)+(0.0359P)^2^+0.4796P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.090 _reflns_number_gt 2948 _reflns_number_total 3418 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file fg1546.cif _[local]_cod_data_source_block 2a _[local]_cod_chemical_formula_sum_orig 'C12 H14 N4 O3 S ' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '449.3-449.4' was changed to '449.35(5)' - 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 1380.2(8) _cod_database_code 2009012 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -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_type_symbol S 0.54356(5) 0.21876(3) 0.19490(9) 0.03266(13) Uani d . 1 S O1 0.59293(12) -0.03636(8) 0.0343(2) 0.0320(3) Uani d . 1 O O2 0.77048(12) -0.00637(8) -0.0209(2) 0.0320(3) Uani d . 1 O O3 0.30306(13) 0.16042(9) 0.1417(3) 0.0406(4) Uani d . 1 O N1 0.45379(15) 0.07639(9) 0.1172(3) 0.0264(3) Uani d . 1 N H1 0.474(2) 0.0288(14) 0.084(3) 0.030(6) Uiso d . 1 H N2 0.67205(14) 0.01448(9) 0.0293(3) 0.0260(3) Uani d . 1 N N3 0.81849(14) 0.14222(10) 0.2328(3) 0.0284(4) Uani d . 1 N H3 0.804(2) 0.1119(15) 0.331(4) 0.038(7) Uiso d . 1 H N4 0.78145(15) 0.18106(10) -0.0837(3) 0.0274(4) Uani d . 1 N H4 0.827(2) 0.2188(14) -0.076(4) 0.035(6) Uiso d . 1 H C1 0.54568(17) 0.12483(10) 0.1272(3) 0.0246(4) Uani d . 1 C C2 0.65305(16) 0.09083(11) 0.0762(3) 0.0240(4) Uani d . 1 C C3 0.75643(16) 0.14088(11) 0.0736(3) 0.0248(4) Uani d . 1 C C4 0.33855(17) 0.09430(12) 0.1304(3) 0.0270(4) Uani d . 1 C C5 0.26146(16) 0.02557(11) 0.1261(3) 0.0251(4) Uani d . 1 C C6 0.29679(17) -0.05146(12) 0.1344(3) 0.0289(4) Uani d . 1 C H6 0.3754 -0.0632 0.1455 0.035 Uiso calc R 1 H C7 0.21786(19) -0.11140(13) 0.1268(4) 0.0354(5) Uani d . 1 C H7 0.2425 -0.1640 0.1332 0.042 Uiso calc R 1 H C8 0.1027(2) -0.09449(14) 0.1096(4) 0.0374(5) Uani d . 1 C H8 0.0488 -0.1356 0.1026 0.045 Uiso calc R 1 H C9 0.06686(18) -0.01809(15) 0.1026(3) 0.0376(5) Uani d . 1 C H9 -0.0118 -0.0066 0.0924 0.045 Uiso calc R 1 H C10 0.14531(17) 0.04178(13) 0.1104(3) 0.0336(5) Uani d . 1 C H10 0.1202 0.0943 0.1051 0.040 Uiso calc R 1 H C11 0.92073(18) 0.18866(13) 0.2549(4) 0.0382(5) Uani d . 1 C H111 0.9765 0.1729 0.1560 0.057 Uiso calc R 1 H H112 0.9525 0.1805 0.3860 0.057 Uiso calc R 1 H H113 0.9021 0.2439 0.2376 0.057 Uiso calc R 1 H C12 0.7111(2) 0.18247(13) -0.2605(3) 0.0347(5) Uani d . 1 C H121 0.7008 0.1292 -0.3091 0.052 Uiso calc R 1 H H122 0.7485 0.2140 -0.3613 0.052 Uiso calc R 1 H H123 0.6369 0.2051 -0.2295 0.052 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 0.0318(2) 0.0199(2) 0.0463(3) 0.0010(2) 0.0037(2) -0.0055(2) O1 0.0286(7) 0.0218(7) 0.0457(9) -0.0032(5) 0.0039(7) -0.0047(6) O2 0.0269(7) 0.0254(7) 0.0439(9) 0.0041(6) 0.0057(7) -0.0034(6) O3 0.0331(8) 0.0250(7) 0.0637(12) 0.0060(6) 0.0011(8) -0.0001(7) N1 0.0244(8) 0.0216(7) 0.0332(8) 0.0007(7) 0.0050(8) -0.0021(7) N2 0.0285(8) 0.0194(8) 0.0302(8) -0.0011(6) 0.0006(7) -0.0003(7) N3 0.0270(8) 0.0260(8) 0.0322(9) -0.0015(6) -0.0027(7) 0.0041(7) N4 0.0291(8) 0.0235(8) 0.0296(9) -0.0042(7) 0.0017(7) 0.0016(7) C1 0.0264(8) 0.0222(8) 0.0252(9) 0.0002(8) 0.0025(8) 0.0007(7) C2 0.0247(9) 0.0196(8) 0.0277(10) -0.0004(7) 0.0018(8) 0.0006(7) C3 0.0235(9) 0.0194(8) 0.0316(10) 0.0033(7) 0.0027(8) -0.0008(7) C4 0.0273(9) 0.0264(9) 0.0273(10) 0.0022(8) 0.0016(8) -0.0001(8) C5 0.0246(9) 0.0286(9) 0.0220(9) -0.0008(7) 0.0030(7) -0.0001(8) C6 0.0265(9) 0.0293(10) 0.0307(10) -0.0007(8) -0.0003(8) -0.0008(8) C7 0.0349(11) 0.0305(11) 0.0407(12) -0.0052(9) 0.0012(10) -0.0002(9) C8 0.0344(11) 0.0413(12) 0.0364(12) -0.0128(10) 0.0011(10) 0.0003(10) C9 0.0237(10) 0.0521(14) 0.0370(11) -0.0041(9) 0.0030(9) 0.0026(11) C10 0.0263(10) 0.0369(12) 0.0376(11) 0.0049(9) 0.0045(9) -0.0005(10) C11 0.0294(10) 0.0309(10) 0.0544(15) -0.0021(8) -0.0071(10) -0.0007(10) C12 0.0444(12) 0.0318(10) 0.0279(11) -0.0048(9) 0.0011(9) 0.0024(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 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 -2 -2 -1 -5 0 -1 -1 -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 129.28(17) yes C1 N1 H1 111.6(15) ? C4 N1 H1 118.7(15) ? O2 N2 O1 118.93(15) ? O2 N2 C2 119.10(16) ? O1 N2 C2 121.97(16) ? C3 N3 C11 123.95(19) ? C3 N3 H3 121.6(17) ? C11 N3 H3 114.2(17) ? C3 N4 C12 123.86(17) ? C3 N4 H4 119.9(17) ? C12 N4 H4 113.4(17) ? N1 C1 C2 115.96(16) yes N1 C1 S 125.95(15) yes C2 C1 S 118.08(15) ? N2 C2 C1 126.20(17) yes N2 C2 C3 114.59(16) ? C1 C2 C3 119.21(16) ? N4 C3 N3 123.05(18) yes N4 C3 C2 119.84(18) ? N3 C3 C2 117.12(17) ? O3 C4 N1 123.11(19) yes O3 C4 C5 122.22(19) ? N1 C4 C5 114.66(17) ? C6 C5 C10 119.05(18) ? C6 C5 C4 124.87(18) ? C10 C5 C4 116.08(18) ? C7 C6 C5 120.30(19) ? C7 C6 H6 119.8 ? C5 C6 H6 119.8 ? C6 C7 C8 120.1(2) ? C6 C7 H7 120.0 ? C8 C7 H7 120.0 ? C9 C8 C7 120.0(2) ? C9 C8 H8 120.0 ? C7 C8 H8 120.0 ? C8 C9 C10 120.1(2) ? C8 C9 H9 120.0 ? C10 C9 H9 120.0 ? C9 C10 C5 120.5(2) ? C9 C10 H10 119.7 ? C5 C10 H10 119.7 ? N3 C11 H111 109.5 ? N3 C11 H112 109.5 ? H111 C11 H112 109.5 ? N3 C11 H113 109.5 ? H111 C11 H113 109.5 ? H112 C11 H113 109.5 ? N4 C12 H121 109.5 ? N4 C12 H122 109.5 ? H121 C12 H122 109.5 ? N4 C12 H123 109.5 ? H121 C12 H123 109.5 ? H122 C12 H123 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S C1 1.6781(19) yes O1 N2 1.277(2) ? O2 N2 1.261(2) ? O3 C4 1.212(2) ? N1 C1 1.367(3) yes N1 C4 1.394(3) yes N1 H1 0.88(2) ? N2 C2 1.368(2) yes N3 C3 1.310(3) yes N3 C11 1.452(3) ? N3 H3 0.87(3) ? N4 C3 1.310(3) yes N4 C12 1.464(3) ? N4 H4 0.84(3) ? C1 C2 1.435(3) yes C2 C3 1.490(3) yes C4 C5 1.489(3) ? C5 C6 1.388(3) ? C5 C10 1.400(3) ? C6 C7 1.388(3) ? C6 H6 0.9500 ? C7 C8 1.392(3) ? C7 H7 0.9500 ? C8 C9 1.379(3) ? C8 H8 0.9500 ? C9 C10 1.383(3) ? C9 H9 0.9500 ? C10 H10 0.9500 ? C11 H111 0.9800 ? C11 H112 0.9800 ? C11 H113 0.9800 ? C12 H121 0.9800 ? C12 H122 0.9800 ? C12 H123 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 _geom_hbond_publ_flag N1 H1 O1 . 0.88(2) 1.83(2) 2.599(2) 145(2) yes N3 H3 O1 2_655 0.87(3) 2.25(3) 2.937(2) 136(2) yes N3 H3 O2 2_655 0.87(3) 2.25(3) 3.060(2) 155(2) yes N4 H4 O3 3_555 0.84(3) 2.14(2) 2.762(2) 130(2) 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 -170.06(19) yes C4 N1 C1 S 10.6(3) ? O2 N2 C2 C1 176.89(19) ? O1 N2 C2 C1 -2.9(3) ? O2 N2 C2 C3 -3.6(3) ? O1 N2 C2 C3 176.59(18) yes N1 C1 C2 N2 -3.6(3) ? S C1 C2 N2 175.82(16) yes N1 C1 C2 C3 176.89(17) yes S C1 C2 C3 -3.7(3) ? C12 N4 C3 N3 -177.76(19) ? C12 N4 C3 C2 2.2(3) ? C11 N3 C3 N4 0.8(3) ? C11 N3 C3 C2 -179.15(18) ? N2 C2 C3 N4 95.0(2) yes C1 C2 C3 N4 -85.4(2) yes N2 C2 C3 N3 -85.1(2) yes C1 C2 C3 N3 94.5(2) yes C1 N1 C4 O3 4.8(3) ? C1 N1 C4 C5 -176.19(18) yes O3 C4 C5 C6 -172.7(2) ? N1 C4 C5 C6 8.2(3) ? O3 C4 C5 C10 7.9(3) ? N1 C4 C5 C10 -171.06(18) yes C10 C5 C6 C7 0.2(3) ? C4 C5 C6 C7 -179.1(2) ? C5 C6 C7 C8 0.3(3) ? C6 C7 C8 C9 -0.8(4) ? C7 C8 C9 C10 0.7(4) ? C8 C9 C10 C5 -0.2(3) ? C6 C5 C10 C9 -0.2(3) ? C4 C5 C10 C9 179.1(2) ?