#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/37/2013759.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_2013759 loop_ _publ_author_name 'Tafeenko, Viktor A.' 'Peschar, Rene' 'Kaukova, Olga V.' 'Schenk, Henk' 'Aslanov, Leonid A.' _publ_section_title ; N,N-Dimethylanilinium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1H-pyrrol-2-olate ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o62 _journal_page_last o64 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H12 N 1+, C8 H N4 O2 1-' _chemical_formula_moiety 'C8 H12 N 1+, C8 H N4 O2 1-' _chemical_formula_sum 'C16 H13 N5 O2' _chemical_formula_weight 307.31 _chemical_melting_point 221 _chemical_name_systematic ; N,N-dimethylanilinium 3-cyano-4-(dicyanomethylene)-5-oxo-4,5-dihydro-1H-pyrrol-2-olate ; _space_group_IT_number 31 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac -2' _symmetry_space_group_name_H-M 'P m n 21' _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 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 7.0399(7) _cell_length_b 12.5636(12) _cell_length_c 8.6695(8) _cell_measurement_reflns_used 925 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 30 _cell_measurement_theta_min 3 _cell_volume 766.79(13) _computing_cell_refinement 'SAINT-Plus (Bruker, 1998)' _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction SAINT-Plus _computing_molecular_graphics 'DIAMOND (Brandenburg, 2000) and ORTEP-3 (Farrugia, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 110(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker SMART 1000 CCD area-detector' _diffrn_measurement_method '\f and \w scans' _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 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5974 _diffrn_reflns_theta_full 30.08 _diffrn_reflns_theta_max 30.08 _diffrn_reflns_theta_min 1.62 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.194 _refine_diff_density_min -0.354 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 153 _refine_ls_number_reflns 1282 _refine_ls_number_restraints 19 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0492 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0684P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1025 _refine_ls_wR_factor_ref 0.1124 _reflns_number_gt 936 _reflns_number_total 1283 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fg1710.cif _[local]_cod_data_source_block I _cod_database_code 2013759 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y, z' 'x+1/2, -y, 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 O1 0.5000 0.11422(17) 0.3697(3) 0.0623(7) Uani d S 1 . . O O2 0.5000 0.4752(2) 0.3956(3) 0.0994(13) Uani d S 1 . . O N1 0.5000 0.2962(2) 0.3428(3) 0.0617(8) Uani d S 1 . . N H1 0.5000 0.2988 0.2413 0.074 Uiso calc SR 1 . . H N2 0.5000 0.3371(3) 1.0000(4) 0.0721(10) Uani d S 1 . . N N3 0.5000 0.6137(3) 0.6991(5) 0.1011(16) Uani d S 1 . . N N4 0.5000 0.0834(2) 0.7873(4) 0.0569(7) Uani d S 1 . . N C2 0.5000 0.2032(2) 0.4266(4) 0.0468(7) Uani d S 1 . . C C3 0.5000 0.2325(2) 0.5876(3) 0.0378(6) Uani d S 1 . . C C4 0.5000 0.3428(2) 0.5998(3) 0.0410(7) Uani d S 1 . . C C5 0.5000 0.3840(3) 0.4354(4) 0.0588(10) Uani d S 1 . . C C6 0.5000 0.4110(2) 0.7236(3) 0.0478(8) Uani d S 1 . . C C7 0.5000 0.5236(3) 0.7070(4) 0.0664(11) Uani d S 1 . . C C8 0.5000 0.3713(3) 0.8772(4) 0.0518(8) Uani d S 1 . . C C9 0.5000 0.1527(2) 0.7012(4) 0.0411(6) Uani d S 1 . . C N5 0.5000 0.8927(3) 0.4766(3) 0.0413(8) Uani d SPD 0.833(5) . 1 N H5 0.5000 0.9652 0.4548 0.050 Uiso calc SPR 0.833(5) . 1 H C10 0.5000 0.8365(3) 0.3260(4) 0.0381(9) Uani d SPD 0.833(5) . 1 C C11 0.5000 0.8970(3) 0.1941(5) 0.0434(10) Uani d SPD 0.833(5) . 1 C H11 0.5000 0.9725 0.1998 0.052 Uiso calc SPR 0.833(5) . 1 H C12 0.5000 0.8458(4) 0.0520(5) 0.0518(13) Uani d SPD 0.833(5) . 1 C H12 0.5000 0.8864 -0.0405 0.062 Uiso calc SPR 0.833(5) . 1 H C13 0.5000 0.7366(4) 0.0451(5) 0.0538(14) Uani d SPD 0.833(5) . 1 C H13 0.5000 0.7019 -0.0522 0.065 Uiso calc SPR 0.833(5) . 1 H C14 0.5000 0.6769(4) 0.1787(6) 0.0546(13) Uani d SPD 0.833(5) . 1 C H14 0.5000 0.6014 0.1730 0.066 Uiso calc SPR 0.833(5) . 1 H C15 0.5000 0.7266(3) 0.3204(5) 0.0497(11) Uani d SPD 0.833(5) . 1 C H15 0.5000 0.6860 0.4127 0.060 Uiso calc SPR 0.833(5) . 1 H C16 0.3262(3) 0.8711(2) 0.5681(3) 0.0581(6) Uani d PD 0.83 A 1 C H16A 0.3214 0.7954 0.5950 0.087 Uiso calc PR 0.83 A 1 H H16B 0.2138 0.8897 0.5071 0.087 Uiso calc PR 0.83 A 1 H H16C 0.3284 0.9138 0.6626 0.087 Uiso calc PR 0.83 A 1 H N51 0.5000 0.8200(17) 0.5085(19) 0.053(3) Uiso d SPD 0.167(5) . 2 N H51 0.5000 0.7530 0.5540 0.063 Uiso calc SPR 0.167(5) . 2 H C101 0.5000 0.7975(19) 0.339(2) 0.053(3) Uiso d SPD 0.167(5) . 2 C C111 0.5000 0.6980(19) 0.282(3) 0.053(3) Uiso d SPD 0.167(5) . 2 C H111 0.5000 0.6383 0.3495 0.063 Uiso calc SPR 0.167(5) . 2 H C121 0.5000 0.684(2) 0.126(3) 0.053(3) Uiso d SPD 0.167(5) . 2 C H121 0.5000 0.6142 0.0845 0.063 Uiso calc SPR 0.167(5) . 2 H C131 0.5000 0.768(2) 0.028(3) 0.053(3) Uiso d SPD 0.167(5) . 2 C H131 0.5000 0.7573 -0.0801 0.063 Uiso calc SPR 0.167(5) . 2 H C141 0.5000 0.870(2) 0.088(3) 0.053(3) Uiso d SPD 0.167(5) . 2 C H141 0.5000 0.9296 0.0206 0.063 Uiso calc SPR 0.167(5) . 2 H C151 0.5000 0.884(2) 0.244(3) 0.053(3) Uiso d SPD 0.167(5) . 2 C H151 0.5000 0.9539 0.2858 0.063 Uiso calc SPR 0.167(5) . 2 H C161 0.3262(3) 0.8711(2) 0.5681(3) 0.0581(6) Uani d PD 0.17 B 2 C H16D 0.2144 0.8361 0.5236 0.087 Uiso calc PR 0.17 B 2 H H16E 0.3259 0.9465 0.5395 0.087 Uiso calc PR 0.17 B 2 H H16F 0.3226 0.8645 0.6807 0.087 Uiso calc PR 0.17 B 2 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 O1 0.111(2) 0.0367(12) 0.0389(13) 0.000 0.000 -0.0094(11) O2 0.226(4) 0.0340(14) 0.0382(13) 0.000 0.000 0.0064(11) N1 0.120(2) 0.0401(16) 0.0250(12) 0.000 0.000 0.0027(12) N2 0.125(3) 0.061(2) 0.0298(15) 0.000 0.000 0.0013(15) N3 0.213(5) 0.0407(18) 0.050(2) 0.000 0.000 -0.0057(19) N4 0.0887(19) 0.0410(14) 0.0410(14) 0.000 0.000 0.0074(13) C2 0.076(2) 0.0345(16) 0.0297(15) 0.000 0.000 -0.0029(12) C3 0.0587(17) 0.0295(15) 0.0254(12) 0.000 0.000 -0.0002(11) C4 0.0641(18) 0.0330(16) 0.0261(13) 0.000 0.000 0.0010(11) C5 0.113(3) 0.0382(18) 0.0250(13) 0.000 0.000 0.0043(14) C6 0.083(2) 0.0351(16) 0.0253(14) 0.000 0.000 -0.0027(12) C7 0.130(4) 0.0399(17) 0.0295(16) 0.000 0.000 -0.0076(14) C8 0.087(2) 0.0384(17) 0.0299(15) 0.000 0.000 -0.0039(14) C9 0.0594(17) 0.0314(13) 0.0324(14) 0.000 0.000 -0.0020(12) N5 0.0623(19) 0.0310(18) 0.0307(15) 0.000 0.000 -0.0011(12) C10 0.0569(19) 0.032(2) 0.0256(18) 0.000 0.000 -0.0054(17) C11 0.065(2) 0.033(2) 0.032(2) 0.000 0.000 -0.0013(17) C12 0.074(2) 0.052(4) 0.029(2) 0.000 0.000 0.0001(19) C13 0.080(3) 0.051(3) 0.030(2) 0.000 0.000 -0.011(2) C14 0.083(3) 0.0337(19) 0.047(3) 0.000 0.000 -0.009(2) C15 0.082(3) 0.033(2) 0.034(2) 0.000 0.000 0.0023(17) C16 0.0669(13) 0.0662(17) 0.0412(12) -0.0016(11) 0.0063(11) -0.0105(11) C161 0.0669(13) 0.0662(17) 0.0412(12) -0.0016(11) 0.0063(11) -0.0105(11) 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 O1 C2 . 1.222(4) ? O2 C5 . 1.197(4) ? N1 C5 . 1.364(4) ? N1 C2 . 1.376(4) ? N1 H1 . 0.8800 ? N2 C8 . 1.148(4) ? N3 C7 . 1.134(4) ? N4 C9 . 1.147(4) ? C2 C3 . 1.444(4) ? C3 C4 . 1.390(4) ? C3 C9 . 1.405(4) ? C4 C6 . 1.373(4) ? C4 C5 . 1.516(4) ? C6 C8 . 1.421(4) ? C6 C7 . 1.422(5) ? N5 C16 3_655 1.484(3) ? N5 C16 . 1.484(3) ? N5 C10 . 1.485(4) ? N5 H5 . 0.9300 ? C10 C11 . 1.373(5) ? C10 C15 . 1.381(6) ? C11 C12 . 1.389(6) ? C11 H11 . 0.9500 ? C12 C13 . 1.374(8) ? C12 H12 . 0.9500 ? C13 C14 . 1.379(6) ? C13 H13 . 0.9500 ? C14 C15 . 1.378(6) ? C14 H14 . 0.9500 ? C15 H15 . 0.9500 ? C16 H16A . 0.9800 ? C16 H16B . 0.9800 ? C16 H16C . 0.9800 ? N51 C161 3_655 1.475(10) ? N51 C101 . 1.494(16) ? N51 H51 . 0.9300 ? C101 C111 . 1.344(17) ? C101 C151 . 1.367(18) ? C111 C121 . 1.369(18) ? C111 H111 . 0.9500 ? C121 C131 . 1.35(2) ? C121 H121 . 0.9500 ? C131 C141 . 1.376(19) ? C131 H131 . 0.9500 ? C141 C151 . 1.364(19) ? C141 H141 . 0.9500 ? C151 H151 . 0.9500 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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_site_symmetry_1 _geom_angle C5 N1 C2 . 112.1(3) C5 N1 H1 . 124.0 C2 N1 H1 . 124.0 O1 C2 N1 . 124.3(3) O1 C2 C3 . 128.6(3) N1 C2 C3 . 107.1(3) C4 C3 C9 . 131.2(3) C4 C3 C2 . 109.1(3) C9 C3 C2 . 119.7(3) C6 C4 C3 . 132.9(3) C6 C4 C5 . 121.5(3) C3 C4 C5 . 105.6(3) O2 C5 N1 . 127.2(3) O2 C5 C4 . 126.7(3) N1 C5 C4 . 106.2(3) C4 C6 C8 . 120.9(3) C4 C6 C7 . 122.8(3) C8 C6 C7 . 116.3(3) N3 C7 C6 . 177.7(4) N2 C8 C6 . 178.5(4) N4 C9 C3 . 176.1(3) C16 N5 C16 3_655 111.1(3) C16 N5 C10 3_655 112.51(18) C16 N5 C10 . 112.51(18) C16 N5 H5 3_655 106.7 C16 N5 H5 . 106.7 C10 N5 H5 . 106.7 C11 C10 C15 . 121.6(3) C11 C10 N5 . 117.9(3) C15 C10 N5 . 120.5(4) C10 C11 C12 . 118.8(4) C10 C11 H11 . 120.6 C12 C11 H11 . 120.6 C13 C12 C11 . 120.1(4) C13 C12 H12 . 120.0 C11 C12 H12 . 120.0 C12 C13 C14 . 120.4(4) C12 C13 H13 . 119.8 C14 C13 H13 . 119.8 C15 C14 C13 . 120.1(4) C15 C14 H14 . 119.9 C13 C14 H14 . 119.9 C14 C15 C10 . 119.0(4) C14 C15 H15 . 120.5 C10 C15 H15 . 120.5 N5 C16 H16A . 109.5 N5 C16 H16B . 109.5 H16A C16 H16B . 109.5 N5 C16 H16C . 109.5 H16A C16 H16C . 109.5 H16B C16 H16C . 109.5 C161 N51 C101 3_655 115.2(8) C161 N51 H51 3_655 104.2 C101 N51 H51 . 104.2 C111 C101 C151 . 121.1(17) C111 C101 N51 . 123(2) C151 C101 N51 . 116.4(18) C101 C111 C121 . 119(2) C101 C111 H111 . 120.6 C121 C111 H111 . 120.6 C131 C121 C111 . 121(2) C131 C121 H121 . 119.3 C111 C121 H121 . 119.3 C121 C131 C141 . 119(2) C121 C131 H131 . 120.3 C141 C131 H131 . 120.3 C151 C141 C131 . 120(2) C151 C141 H141 . 120.2 C131 C141 H141 . 120.2 C141 C151 C101 . 120(2) C141 C151 H151 . 120.1 C101 C151 H151 . 120.1 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 N2 1_554 0.88 2.15 3.016(5) 169 y N5 H5 O1 1_565 0.93 2.01 2.933(4) 170 y N51 H51 N3 . 0.93 2.16 3.07(2) 169 y C11 H11 O1 1_565 0.95 2.31 3.125(5) 143 y C13 H13 N3 1_554 0.95 2.42 3.374(6) 180 y C14 H14 O2 1_555 0.95 2.50 3.156(6) 126 y C15 H15 O2 1_555 0.95 2.65 3.226(5) 119 y C16 H16B N4 2_564 0.98 2.45 3.394(3) 161 y 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_site_symmetry_1 _geom_torsion C16 N5 C10 C11 3_655 -116.8(2) C16 N5 C10 C11 . 116.8(2) C16 N5 C10 C15 3_655 63.2(2) C16 N5 C10 C15 . -63.2(2) C161 N51 C101 C111 3_655 113.5(12) C161 N51 C101 C151 3_655 -66.5(12)