#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/46/2014638.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_2014638 loop_ _publ_author_name 'U\,car, \.Ibrahim' 'Bulut, Ahmet' 'Ye\,silel, Okan Zafer' 'Odaba\,soglu, Mustafa' 'B\"uy\"ukg\"ung\"or, Orhan' _publ_section_title ; 3-Acetoxy-2-(acetylamino)pyridinium-1-squarate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o148 _journal_page_last o150 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C13 H10 N2 O6' _chemical_formula_moiety 'C13 H10 N2 O6' _chemical_formula_sum 'C13 H10 N2 O6' _chemical_formula_weight 290.23 _chemical_name_systematic ; 3-Acetoxy-2-(acetylamino)pyridinium-1-squarate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 88.895(15) _cell_angle_beta 87.795(15) _cell_angle_gamma 66.667(14) _cell_formula_units_Z 2 _cell_length_a 8.8959(16) _cell_length_b 8.9014(16) _cell_length_c 8.9288(16) _cell_measurement_reflns_used 5022 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 26.00 _cell_measurement_theta_min 2.49 _cell_volume 648.7(2) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Stoe IPDS 2' _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 0.0870 _diffrn_reflns_av_sigmaI/netI 0.0888 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 8629 _diffrn_reflns_theta_full 25.85 _diffrn_reflns_theta_max 25.83 _diffrn_reflns_theta_min 2.49 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 300 _exptl_crystal_size_max 0.280 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.224 _refine_diff_density_min -0.199 _refine_ls_extinction_coef 0.027(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 193 _refine_ls_number_reflns 2475 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.1349 _refine_ls_R_factor_gt 0.0690 _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^)+(0.0569P)^2^+0.2421P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1344 _refine_ls_wR_factor_ref 0.1540 _reflns_number_gt 1366 _reflns_number_total 2477 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file dn1073.cif _[local]_cod_data_source_block I _cod_database_code 2014638 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 C1 0.1598(5) 0.4645(4) 0.7452(4) 0.0387(9) Uani d . 1 . . C C2 0.1712(5) 0.4275(5) 0.9028(5) 0.0463(10) Uani d . 1 . . C C3 0.1503(6) 0.2713(5) 0.8675(5) 0.0507(11) Uani d . 1 . . C C4 0.1389(5) 0.3220(4) 0.7035(4) 0.0397(9) Uani d . 1 . . C C5 0.1245(5) 0.7430(5) 0.7549(4) 0.0468(10) Uani d . 1 . . C H5 0.0875 0.7436 0.8537 0.056 Uiso calc R 1 . . H C6 0.1368(5) 0.8782(5) 0.6964(5) 0.0494(11) Uani d . 1 . . C H6 0.1134 0.9695 0.7563 0.059 Uiso calc R 1 . . H C7 0.1841(5) 0.8817(5) 0.5472(5) 0.0457(10) Uani d . 1 . . C H7 0.1932 0.9748 0.5064 0.055 Uiso calc R 1 . . H C8 0.2171(5) 0.7469(4) 0.4614(4) 0.0390(9) Uani d . 1 . . C C9 0.2157(5) 0.6018(4) 0.5227(4) 0.0362(9) Uani d . 1 . . C C10 0.3865(5) 0.3874(4) 0.3475(4) 0.0395(9) Uani d . 1 . . C C11 0.3994(6) 0.2277(5) 0.2900(5) 0.0591(13) Uani d . 1 . . C H11A 0.4985 0.1792 0.2300 0.089 Uiso calc R 1 . . H H11B 0.3069 0.2438 0.2301 0.089 Uiso calc R 1 . . H H11C 0.4012 0.1566 0.3728 0.089 Uiso calc R 1 . . H C12 0.3697(6) 0.7824(5) 0.2508(5) 0.0490(11) Uani d . 1 . . C C13 0.3782(7) 0.7723(7) 0.0848(5) 0.0763(16) Uani d . 1 . . C H13A 0.3130 0.8775 0.0434 0.114 Uiso calc R 1 . . H H13B 0.3371 0.6934 0.0540 0.114 Uiso calc R 1 . . H H13C 0.4899 0.7397 0.0495 0.114 Uiso calc R 1 . . H N1 0.1660(4) 0.6046(3) 0.6706(3) 0.0367(8) Uani d . 1 . . N N2 0.2535(4) 0.4586(4) 0.4465(3) 0.0396(8) Uani d . 1 . . N H2 0.1892 0.4084 0.4612 0.048 Uiso calc R 1 . . H O1 0.1876(4) 0.4925(4) 1.0171(3) 0.0620(9) Uani d . 1 . . O O2 0.1430(5) 0.1577(4) 0.9380(4) 0.0777(11) Uani d . 1 . . O O3 0.1200(4) 0.2617(3) 0.5851(3) 0.0484(8) Uani d . 1 . . O O4 0.2387(3) 0.7502(3) 0.3077(3) 0.0443(7) Uani d . 1 . . O O5 0.4594(4) 0.8134(4) 0.3293(4) 0.0637(9) Uani d . 1 . . O O6 0.4830(4) 0.4497(3) 0.3171(3) 0.0520(8) Uani d . 1 . . O 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 C1 0.037(2) 0.039(2) 0.039(2) -0.0132(18) 0.0002(17) -0.0025(17) C2 0.047(3) 0.041(2) 0.046(2) -0.012(2) 0.003(2) -0.0028(19) C3 0.059(3) 0.043(2) 0.048(2) -0.017(2) 0.000(2) -0.001(2) C4 0.036(2) 0.034(2) 0.047(2) -0.0125(18) 0.0041(18) -0.0040(17) C5 0.055(3) 0.042(2) 0.040(2) -0.016(2) 0.006(2) -0.0129(18) C6 0.057(3) 0.035(2) 0.056(3) -0.018(2) -0.001(2) -0.0090(19) C7 0.044(3) 0.033(2) 0.061(3) -0.0161(19) -0.009(2) 0.0017(19) C8 0.037(2) 0.036(2) 0.043(2) -0.0123(18) -0.0070(18) 0.0048(17) C9 0.029(2) 0.039(2) 0.039(2) -0.0120(17) -0.0048(17) -0.0028(17) C10 0.042(3) 0.039(2) 0.033(2) -0.010(2) -0.0028(19) 0.0001(16) C11 0.073(3) 0.047(2) 0.050(3) -0.015(2) 0.009(2) -0.011(2) C12 0.051(3) 0.045(2) 0.050(3) -0.017(2) -0.001(2) 0.0083(19) C13 0.088(4) 0.091(4) 0.050(3) -0.036(3) 0.000(3) 0.014(3) N1 0.039(2) 0.0355(17) 0.0356(18) -0.0148(15) 0.0004(15) -0.0049(13) N2 0.042(2) 0.0369(17) 0.0437(18) -0.0194(15) -0.0002(16) -0.0062(14) O1 0.085(2) 0.0593(19) 0.0426(17) -0.0285(17) -0.0102(16) -0.0039(14) O2 0.124(3) 0.0492(19) 0.061(2) -0.037(2) 0.008(2) 0.0074(16) O3 0.060(2) 0.0484(16) 0.0481(17) -0.0326(15) -0.0007(14) -0.0068(13) O4 0.0462(18) 0.0460(16) 0.0414(16) -0.0187(14) -0.0060(13) 0.0059(12) O5 0.062(2) 0.071(2) 0.069(2) -0.0384(18) 0.0017(17) -0.0003(16) O6 0.0434(19) 0.0526(17) 0.0569(18) -0.0162(15) 0.0017(15) 0.0035(13) 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 C1 C4 . 1.411(5) y C1 N1 . 1.422(5) y C1 C2 . 1.437(5) y C2 O1 . 1.224(4) y C2 C3 . 1.515(6) y C3 O2 . 1.202(5) y C3 C4 . 1.519(6) y C4 O3 . 1.242(4) y C5 C6 . 1.344(6) ? C5 N1 . 1.369(5) ? C5 H5 . 0.9300 ? C6 C7 . 1.385(6) ? C6 H6 . 0.9300 ? C7 C8 . 1.361(5) ? C7 H7 . 0.9300 ? C8 O4 . 1.380(4) ? C8 C9 . 1.398(5) ? C9 N2 . 1.370(4) ? C9 N1 . 1.374(5) ? C10 O6 . 1.212(5) y C10 N2 . 1.389(5) ? C10 C11 . 1.480(5) ? C11 H11A . 0.9600 ? C11 H11B . 0.9600 ? C11 H11C . 0.9600 ? C12 O5 . 1.195(5) ? C12 O4 . 1.383(5) ? C12 C13 . 1.484(6) ? C13 H13A . 0.9600 ? C13 H13B . 0.9600 ? C13 H13C . 0.9600 ? N2 H2 . 0.8600 ? 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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 C1 N1 136.4(3) ? C4 C1 C2 95.5(3) ? N1 C1 C2 128.1(3) ? O1 C2 C1 137.0(4) ? O1 C2 C3 135.2(4) ? C1 C2 C3 87.8(3) y O2 C3 C2 136.2(4) y O2 C3 C4 135.7(4) ? C2 C3 C4 88.1(3) ? O3 C4 C1 136.4(4) ? O3 C4 C3 135.0(3) ? C1 C4 C3 88.6(3) ? C6 C5 N1 120.8(4) ? C6 C5 H5 119.6 ? N1 C5 H5 119.6 ? C5 C6 C7 120.2(4) y C5 C6 H6 119.9 ? C7 C6 H6 119.9 ? C8 C7 C6 119.0(4) ? C8 C7 H7 120.5 ? C6 C7 H7 120.5 ? C7 C8 O4 122.0(3) ? C7 C8 C9 121.5(4) ? O4 C8 C9 116.2(3) ? N2 C9 N1 117.1(3) ? N2 C9 C8 125.6(3) ? N1 C9 C8 117.3(3) ? O6 C10 N2 122.3(3) ? O6 C10 C11 124.8(4) ? N2 C10 C11 112.9(4) ? C10 C11 H11A 109.5 ? C10 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? C10 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? O5 C12 O4 122.5(4) ? O5 C12 C13 127.4(5) ? O4 C12 C13 110.1(4) ? C12 C13 H13A 109.5 ? C12 C13 H13B 109.5 ? H13A C13 H13B 109.5 ? C12 C13 H13C 109.5 ? H13A C13 H13C 109.5 ? H13B C13 H13C 109.5 ? C5 N1 C9 121.0(3) ? C5 N1 C1 116.6(3) ? C9 N1 C1 122.3(3) ? C9 N2 C10 125.8(3) ? C9 N2 H2 117.1 ? C10 N2 H2 117.1 ? C8 O4 C12 117.8(3) ? 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 H2 O3 . 0.86 1.96 2.733(4) 149.2 C5 H5 O2 2_567 0.93 2.60 3.449(6) 151.4 C6 H6 O2 1_565 0.93 2.45 3.343(5) 161.3 C7 H7 O3 1_565 0.93 2.48 3.222(4) 136.7 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 C1 C2 O1 -178.6(5) ? N1 C1 C2 O1 0.3(8) ? C4 C1 C2 C3 0.3(3) ? N1 C1 C2 C3 179.2(4) ? O1 C2 C3 O2 -0.3(10) ? C1 C2 C3 O2 -179.2(6) ? O1 C2 C3 C4 178.7(5) ? C1 C2 C3 C4 -0.3(3) ? N1 C1 C4 O3 1.3(8) ? C2 C1 C4 O3 -180.0(5) ? N1 C1 C4 C3 -179.0(5) ? C2 C1 C4 C3 -0.3(3) ? O2 C3 C4 O3 -1.1(9) ? C2 C3 C4 O3 179.9(5) ? O2 C3 C4 C1 179.2(6) ? C2 C3 C4 C1 0.3(3) ? N1 C5 C6 C7 3.2(6) ? C5 C6 C7 C8 0.3(6) ? C6 C7 C8 O4 169.2(4) ? C6 C7 C8 C9 -4.6(6) ? C7 C8 C9 N2 -177.3(4) ? O4 C8 C9 N2 8.5(5) ? C7 C8 C9 N1 5.4(5) ? O4 C8 C9 N1 -168.8(3) ? C6 C5 N1 C9 -2.3(6) ? C6 C5 N1 C1 175.8(4) ? N2 C9 N1 C5 -179.5(4) ? C8 C9 N1 C5 -1.9(5) ? N2 C9 N1 C1 2.6(5) ? C8 C9 N1 C1 -179.9(3) ? C4 C1 N1 C5 154.9(4) ? C2 C1 N1 C5 -23.5(6) y C4 C1 N1 C9 -27.1(7) ? C2 C1 N1 C9 154.6(4) ? N1 C9 N2 C10 -137.6(4) ? C8 C9 N2 C10 45.2(5) ? O6 C10 N2 C9 -1.2(6) ? C11 C10 N2 C9 176.6(3) ? C7 C8 O4 C12 63.5(5) ? C9 C8 O4 C12 -122.4(4) ? O5 C12 O4 C8 -3.0(6) ? C13 C12 O4 C8 177.0(3) ?