#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011617.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_2011617 loop_ _publ_author_name 'Vishweshwar, Peddy' 'Nangia, Ashwini' 'Lynch, Vincent M.' _publ_section_title ; Pyrazine-2,3-dicarboxamide ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1512 _journal_page_last 1514 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C6 H6 N4 O2' _chemical_formula_sum 'C6 H6 N4 O2' _chemical_formula_weight 166.15 _chemical_melting_point 541 _chemical_name_common ; 2,3-Pyrazinedicarboxamide ; _chemical_name_systematic ; Pyrazine-2,3-dicarboxamide ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL97 _cell_angle_alpha 70.826(3) _cell_angle_beta 81.868(3) _cell_angle_gamma 81.163(3) _cell_formula_units_Z 2 _cell_length_a 5.0250(3) _cell_length_b 7.0977(3) _cell_length_c 10.1196(5) _cell_measurement_reflns_used 1868 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 30.02 _cell_measurement_theta_min 3.14 _cell_volume 335.25(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_data_reduction 'SCALEPACK in DENZO-SMN' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLUTON (Spek, 1992)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 153(2) _diffrn_measurement_device 'Nonius Kappa CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal focus for the X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .015 _diffrn_reflns_av_sigmaI/netI .032 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 2623 _diffrn_reflns_theta_max 30.02 _diffrn_reflns_theta_min 3.14 _diffrn_standards_decay_% 'less than 1' _exptl_absorpt_coefficient_mu .129 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description cubic _exptl_crystal_F_000 172 _exptl_crystal_size_max .32 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .30 _refine_diff_density_max .50 _refine_diff_density_min -.20 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 133 _refine_ls_number_reflns 1835 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_restrained_S_obs 1.070 _refine_ls_R_factor_all .037 _refine_ls_R_factor_gt .035 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.0906P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .101 _reflns_number_gt 1754 _reflns_number_total 1868 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file jz1424.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '541K' was changed to '541' - the value should be numeric and without a unit designator. 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 '541K' was changed to '541' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2011617 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 .0144(3) .0132(3) .0245(3) -.0003(2) -.0025(2) -.0052(2) O2 .0204(3) .0114(3) .0170(3) -.0024(2) -.0080(2) -.0009(2) N3 .0140(3) .0150(4) .0147(3) -.0024(2) -.0041(3) -.0037(3) N4 .0158(4) .0117(3) .0243(4) -.0023(3) -.0005(3) -.0010(3) N5 .0172(4) .0108(3) .0176(4) -.0024(3) -.0076(3) -.0032(3) N6 .0175(4) .0113(3) .0190(4) -.0023(3) -.0070(3) -.0013(3) C7 .0156(4) .0108(3) .0131(4) -.0023(3) -.0041(3) -.0036(3) C8 .0119(3) .0106(3) .0121(4) -.0014(3) -.0020(3) -.0027(3) C9 .0188(4) .0128(4) .0190(4) -.0024(3) -.0075(3) .0000(3) C10 .0119(3) .0117(4) .0129(4) -.0010(3) -.0028(3) -.0040(3) C11 .0147(4) .0158(4) .0146(4) -.0022(3) -.0053(3) -.0018(3) C12 .0121(4) .0110(4) .0123(4) -.0018(3) -.0029(3) -.0024(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 O1 .27403(13) .88931(9) .22860(7) .0176(2) Uani d . 1 . O O2 .23121(13) .64845(9) .05365(7) .0165(2) Uani d . 1 . O N3 .76290(15) .54499(11) .36956(8) .0144(2) Uani d . 1 . N N4 .7104(2) .91373(11) .13368(9) .0185(2) Uani d . 1 . N H4A .681(3) 1.044(2) .0973(16) .029(4) Uiso d . 1 . H H4B .877(3) .857(2) .1358(16) .029(4) Uiso d . 1 . H N5 .1634(2) .31990(11) .14050(8) .0148(2) Uani d . 1 . N H5A .047(3) .332(2) .0798(17) .031(4) Uiso d . 1 . H H5B .216(3) .201(2) .1966(16) .028(4) Uiso d . 1 . H N6 .5181(2) .24527(11) .32782(8) .0162(2) Uani d . 1 . N C7 .5066(2) .81334(12) .20777(8) .0129(2) Uani d . 1 . C C8 .5817(2) .59011(12) .27475(8) .0117(2) Uani d . 1 . C C9 .6917(2) .20298(13) .42416(10) .0174(2) Uani d . 1 . C H9 .724(3) .064(2) .4801(15) .028(3) Uiso d . 1 . H C10 .2751(2) .47817(12) .13919(9) .0120(2) Uani d . 1 . C C11 .8183(2) .35200(13) .44334(9) .0153(2) Uani d . 1 . C H11 .951(3) .316(2) .5142(15) .025(3) Uiso d . 1 . H C12 .4643(2) .43856(12) .25113(8) .0118(2) Uani d . 1 . C 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 C7 . 1.2298(10) ? O2 C10 . 1.2424(10) ? N3 C11 . 1.3346(11) ? N3 C8 . 1.3447(11) ? N4 C7 . 1.3322(11) ? N4 H4A . .87(2) ? N4 H4B . .87(2) ? N5 C10 . 1.3263(11) ? N5 H5A . .88(2) ? N5 H5B . .88(2) ? N6 C9 . 1.3301(11) ? N6 C12 . 1.3430(10) ? C7 C8 . 1.5151(11) ? C8 C12 . 1.4021(11) ? C9 C11 . 1.3920(12) ? C9 H9 . .962(15) ? C10 C12 . 1.5097(11) ? C11 H11 . .994(15) ? 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C11 N3 C8 117.44(7) C7 N4 H4A 119.0(10) C7 N4 H4B 121.2(10) H4A N4 H4B 118.6(14) C10 N5 H5A 120.5(10) C10 N5 H5B 119.9(10) H5A N5 H5B 119.3(14) C9 N6 C12 117.52(7) O1 C7 N4 125.14(8) O1 C7 C8 119.84(7) N4 C7 C8 114.96(7) N3 C8 C12 120.90(7) N3 C8 C7 114.01(7) C12 C8 C7 124.94(7) N6 C9 C11 121.60(8) N6 C9 H9 116.5(9) C11 C9 H9 121.9(9) O2 C10 N5 123.88(7) O2 C10 C12 121.01(7) N5 C10 C12 115.12(7) N3 C11 C9 121.43(8) N3 C11 H11 118.7(8) C9 C11 H11 119.9(8) N6 C12 C8 121.00(7) N6 C12 C10 115.58(7) C8 C12 C10 123.41(7) 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 N4 H4A O2 2_675 .873(15) 2.282(15) 3.0970(10) 155.3(14) N4 H4B O1 1_655 .871(15) 2.393(15) 3.0800(10) 136.0(13) N4 H4B O2 1_655 .871(15) 2.373(15) 3.1530(10) 149.1(13) N5 H5A O2 2_565 .882(16) 2.037(16) 2.9190(10) 177.5(15) N5 H5B O1 1_545 .874(15) 2.108(15) 2.8760(10) 146.4(14) N5 H5B N6 1_555 .874(15) 2.271(15) 2.6570(10) 106.6(12) C9 H9 N6 2_656 .964(15) 2.725(15) 3.5450(10) 143.3(12) C11 H11 N3 2_766 .993(15) 2.470(15) 3.3250(10) 144.0(11) 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 C11 N3 C8 C12 -2.40(12) ? C11 N3 C8 C7 173.35(7) ? O1 C7 C8 N3 -114.85(9) yes N4 C7 C8 N3 62.39(10) yes O1 C7 C8 C12 60.71(12) yes N4 C7 C8 C12 -122.06(9) yes C12 N6 C9 C11 -1.38(14) ? C8 N3 C11 C9 -.63(13) ? N6 C9 C11 N3 2.64(15) ? C9 N6 C12 C8 -1.67(13) ? C9 N6 C12 C10 177.59(7) ? N3 C8 C12 N6 3.69(13) ? C7 C8 C12 N6 -171.58(8) ? N3 C8 C12 C10 -175.51(7) ? C7 C8 C12 C10 9.22(13) ? O2 C10 C12 N6 -173.24(8) yes N5 C10 C12 N6 6.84(11) yes O2 C10 C12 C8 6.00(13) yes N5 C10 C12 C8 -173.92(8) yes