# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'C Aakeroy' _publ_contact_author_email aakeroy@ksu.edu loop_ _publ_author_name C.Aakeroy P.Chopade J.Desper A.Rajbanshi G.Ganser data_B1.A11 _database_code_depnum_ccdc_archive 'CCDC 876776' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; P50 2-aminopyrazine, (4-NO2-PhCOOH)2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3) (C7 H5 N O4)2 ; _chemical_formula_sum 'C18 H15 N5 O8' _chemical_formula_weight 429.35 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 13.8994(7) _cell_length_b 5.4845(3) _cell_length_c 13.1317(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.948(2) _cell_angle_gamma 90.00 _cell_volume 979.36(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2139 _cell_measurement_theta_min 3.78 _cell_measurement_theta_max 24.72 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12104 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 32.65 _reflns_number_total 3529 _reflns_number_gt 1564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.1500P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3529 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1557 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.2208 _refine_ls_wR_factor_gt 0.1821 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 0.76032(14) 1.3246(3) 0.39289(15) 0.0555(5) Uani 1 1 d . . . C17 C 0.69575(19) 1.1306(5) 0.4229(3) 0.0906(9) Uani 1 1 d . . . O17 O 0.64255(15) 1.0075(4) 0.35157(17) 0.1035(7) Uani 1 1 d . . . H17 H 0.6044 0.9233 0.3764 0.124 Uiso 0.50 1 calc PR . . O18 O 0.69576(16) 1.0986(4) 0.51690(16) 0.1033(7) Uani 1 1 d . . . H18 H 0.6548 0.9948 0.5228 0.124 Uiso 0.50 1 calc PR . . C12 C 0.81922(16) 1.4608(4) 0.47003(14) 0.0635(6) Uani 1 1 d . . . H12 H 0.8186 1.4311 0.5396 0.076 Uiso 1 1 calc R . . C13 C 0.87901(15) 1.6410(4) 0.44375(13) 0.0604(5) Uani 1 1 d . . . H13 H 0.9191 1.7334 0.4950 0.072 Uiso 1 1 calc R . . C14 C 0.87797(13) 1.6805(3) 0.34069(13) 0.0496(4) Uani 1 1 d . . . N14 N 0.94049(14) 1.8750(3) 0.31185(15) 0.0656(5) Uani 1 1 d . . . O13 O 1.00788(16) 1.9486(4) 0.37962(15) 0.1023(7) Uani 1 1 d . . . O14 O 0.92275(14) 1.9491(3) 0.22248(14) 0.0894(6) Uani 1 1 d . . . C15 C 0.82091(14) 1.5472(4) 0.26218(13) 0.0559(5) Uani 1 1 d . . . H15 H 0.8221 1.5777 0.1928 0.067 Uiso 1 1 calc R . . C16 C 0.76177(14) 1.3665(4) 0.28946(15) 0.0591(5) Uani 1 1 d . . . H16 H 0.7228 1.2726 0.2380 0.071 Uiso 1 1 calc R . . N21 N 0.5450(4) 0.6610(14) 0.4420(6) 0.0563(14) Uani 0.50 1 d P A -1 C22 C 0.5498(3) 0.5791(9) 0.5375(3) 0.0539(9) Uani 0.50 1 d P A -1 N22 N 0.6093(7) 0.682(2) 0.6169(9) 0.083(3) Uani 0.50 1 d P A -1 H22A H 0.641(4) 0.817(12) 0.599(4) 0.099 Uiso 0.50 1 d P B -1 H22B H 0.616(4) 0.619(11) 0.683(5) 0.099 Uiso 0.50 1 d P C -1 C23 C 0.4903(5) 0.3805(18) 0.5558(8) 0.0607(18) Uani 0.50 1 d P A -1 H23 H 0.4937 0.3240 0.6232 0.073 Uiso 0.50 1 calc PR A -1 N24 N 0.4297(3) 0.2752(8) 0.4765(3) 0.0624(9) Uani 0.50 1 d P A -1 C25 C 0.4237(8) 0.359(2) 0.3789(10) 0.069(2) Uani 0.50 1 d P A -1 H25 H 0.3805 0.2875 0.3236 0.082 Uiso 0.50 1 calc PR A -1 C26 C 0.4821(3) 0.5534(8) 0.3612(3) 0.0589(10) Uani 0.50 1 d P A -1 H26 H 0.4784 0.6102 0.2938 0.071 Uiso 0.50 1 calc PR A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0563(11) 0.0483(11) 0.0655(11) -0.0030(8) 0.0205(9) -0.0052(9) C17 0.0777(16) 0.0479(13) 0.164(3) -0.0013(16) 0.0662(18) -0.0059(12) O17 0.0975(13) 0.0807(13) 0.1434(17) -0.0250(12) 0.0507(12) -0.0438(11) O18 0.1325(16) 0.0798(13) 0.1163(14) 0.0049(10) 0.0693(13) -0.0352(11) C12 0.0803(14) 0.0664(13) 0.0463(9) -0.0006(9) 0.0191(9) -0.0129(11) C13 0.0679(12) 0.0640(13) 0.0475(10) -0.0100(9) 0.0082(8) -0.0171(10) C14 0.0522(10) 0.0442(10) 0.0550(10) -0.0027(8) 0.0172(8) -0.0029(8) N14 0.0787(12) 0.0491(10) 0.0783(12) -0.0089(9) 0.0375(9) -0.0091(9) O13 0.1144(14) 0.1018(15) 0.1010(13) -0.0360(10) 0.0460(11) -0.0629(12) O14 0.1144(14) 0.0701(11) 0.0948(12) 0.0278(9) 0.0472(10) 0.0028(10) C15 0.0630(11) 0.0624(12) 0.0427(9) -0.0004(8) 0.0117(8) 0.0000(9) C16 0.0554(10) 0.0637(13) 0.0560(10) -0.0132(9) 0.0065(8) -0.0078(10) N21 0.056(4) 0.056(3) 0.050(2) 0.004(2) -0.002(3) -0.010(3) C22 0.060(2) 0.055(3) 0.046(2) 0.0100(18) 0.0111(17) -0.002(2) N22 0.105(7) 0.087(5) 0.051(3) 0.008(3) 0.002(4) -0.022(5) C23 0.064(5) 0.058(4) 0.056(3) 0.008(3) 0.003(4) -0.008(3) N24 0.069(2) 0.065(3) 0.054(2) 0.0080(19) 0.0135(17) -0.012(2) C25 0.077(6) 0.075(5) 0.050(3) -0.006(3) 0.005(4) -0.014(4) C26 0.061(2) 0.071(3) 0.0420(18) -0.0008(17) 0.0044(16) -0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C16 1.382(3) . ? C11 C12 1.382(3) . ? C11 C17 1.497(3) . ? C17 O18 1.246(3) . ? C17 O17 1.263(3) . ? O17 H17 0.8200 . ? O18 H18 0.8200 . ? C12 C13 1.380(3) . ? C12 H12 0.9300 . ? C13 C14 1.368(2) . ? C13 H13 0.9300 . ? C14 C15 1.374(3) . ? C14 N14 1.474(2) . ? N14 O14 1.218(2) . ? N14 O13 1.219(2) . ? C15 C16 1.381(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? N21 C22 1.321(8) . ? N21 C26 1.361(8) . ? C22 N22 1.317(11) . ? C22 C23 1.419(8) . ? N22 H22A 0.92(6) . ? N22 H22B 0.92(6) . ? C23 N24 1.327(10) . ? C23 H23 0.9300 . ? N24 C25 1.349(14) . ? C25 C26 1.387(10) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 120.24(18) . . ? C16 C11 C17 120.6(2) . . ? C12 C11 C17 119.2(2) . . ? O18 C17 O17 122.6(2) . . ? O18 C17 C11 119.0(3) . . ? O17 C17 C11 118.4(3) . . ? C17 O17 H17 109.5 . . ? C17 O18 H18 109.5 . . ? C13 C12 C11 119.96(17) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 118.51(17) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C13 C14 C15 122.98(18) . . ? C13 C14 N14 118.87(16) . . ? C15 C14 N14 118.15(16) . . ? O14 N14 O13 124.4(2) . . ? O14 N14 C14 118.45(19) . . ? O13 N14 C14 117.17(18) . . ? C14 C15 C16 117.98(16) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C15 C16 C11 120.31(17) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C22 N21 C26 119.4(5) . . ? N22 C22 N21 120.4(6) . . ? N22 C22 C23 119.2(7) . . ? N21 C22 C23 120.3(7) . . ? C22 N22 H22A 114(4) . . ? C22 N22 H22B 121(4) . . ? H22A N22 H22B 126(5) . . ? N24 C23 C22 119.9(7) . . ? N24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 N24 C25 120.0(7) . . ? N24 C25 C26 119.9(9) . . ? N24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? N21 C26 C25 120.3(7) . . ? N21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C17 O18 -179.6(2) . . . . ? C12 C11 C17 O18 0.9(3) . . . . ? C16 C11 C17 O17 -0.3(3) . . . . ? C12 C11 C17 O17 -179.9(2) . . . . ? C16 C11 C12 C13 0.6(3) . . . . ? C17 C11 C12 C13 -179.8(2) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C15 -0.7(3) . . . . ? C12 C13 C14 N14 179.10(19) . . . . ? C13 C14 N14 O14 -162.64(19) . . . . ? C15 C14 N14 O14 17.2(3) . . . . ? C13 C14 N14 O13 18.4(3) . . . . ? C15 C14 N14 O13 -161.78(19) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? N14 C14 C15 C16 -179.45(17) . . . . ? C14 C15 C16 C11 0.5(3) . . . . ? C12 C11 C16 C15 -1.0(3) . . . . ? C17 C11 C16 C15 179.45(19) . . . . ? C26 N21 C22 N22 -179.3(8) . . . . ? C26 N21 C22 C23 0.1(13) . . . . ? N22 C22 C23 N24 179.8(9) . . . . ? N21 C22 C23 N24 0.3(14) . . . . ? C22 C23 N24 C25 -1.0(13) . . . . ? C23 N24 C25 C26 1.1(15) . . . . ? C22 N21 C26 C25 0.0(11) . . . . ? N24 C25 C26 N21 -0.6(15) . . . . ? 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_site_symmetry_A O17 H17 N21 0.82 1.95 2.744(6) 163.9 . O18 H18 N24 0.82 1.89 2.704(5) 171.1 3_666 N22 H22A O18 0.92(6) 2.11(7) 3.006(10) 164(5) . N22 H22B O17 0.92(6) 2.28(6) 3.194(11) 175(6) 4_576 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 32.65 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.203 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.040 #END data_B1.A14 _database_code_depnum_ccdc_archive 'CCDC 876777' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; P54 2-aminopyrazine, 3,5-(NO2)2-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3) (C7 H4 N2 O6) ; _chemical_formula_sum 'C11 H9 N5 O6' _chemical_formula_weight 307.23 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6755(11) _cell_length_b 8.8822(11) _cell_length_c 9.6107(15) _cell_angle_alpha 84.645(10) _cell_angle_beta 82.063(11) _cell_angle_gamma 74.877(10) _cell_volume 625.34(15) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2476 _cell_measurement_theta_min 2.77 _cell_measurement_theta_max 28.14 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7084 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1088 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 29.69 _reflns_number_total 7084 _reflns_number_gt 3116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1600P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7084 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2102 _refine_ls_R_factor_gt 0.0989 _refine_ls_wR_factor_ref 0.3508 _refine_ls_wR_factor_gt 0.2664 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.4924(4) 0.9633(3) 0.7452(3) 0.0295(7) Uani 1 1 d . . . H11 H 0.553(6) 0.908(5) 0.663(5) 0.044 Uiso 1 1 d . . . C12 C 0.3798(5) 0.9140(4) 0.8477(4) 0.0286(8) Uani 1 1 d . . . N12 N 0.3622(5) 0.7677(4) 0.8529(4) 0.0352(8) Uani 1 1 d . . . H12A H 0.432(6) 0.709(5) 0.795(5) 0.042 Uiso 1 1 d . . . H12B H 0.282(6) 0.749(5) 0.928(5) 0.042 Uiso 1 1 d . . . C13 C 0.2849(5) 1.0228(4) 0.9481(4) 0.0315(8) Uani 1 1 d . . . H13 H 0.2008 0.9913 1.0196 0.038 Uiso 1 1 calc R . . N14 N 0.3065(4) 1.1639(3) 0.9479(3) 0.0358(8) Uani 1 1 d . . . C15 C 0.4270(5) 1.2073(4) 0.8436(4) 0.0334(8) Uani 1 1 d . . . H15 H 0.4478 1.3083 0.8420 0.040 Uiso 1 1 calc R . . C16 C 0.5182(5) 1.1090(4) 0.7417(4) 0.0320(8) Uani 1 1 d . . . H16 H 0.5991 1.1425 0.6688 0.038 Uiso 1 1 calc R . . C21 C 0.7872(5) 0.5439(4) 0.4459(4) 0.0270(7) Uani 1 1 d . . . C27 C 0.6652(5) 0.6389(4) 0.5602(4) 0.0307(8) Uani 1 1 d . . . O21 O 0.6523(4) 0.7846(3) 0.5453(3) 0.0390(7) Uani 1 1 d . . . O22 O 0.5908(4) 0.5678(3) 0.6593(3) 0.0373(7) Uani 1 1 d . . . C22 C 0.8004(5) 0.3845(4) 0.4459(4) 0.0290(8) Uani 1 1 d . . . H22 H 0.7287 0.3357 0.5151 0.035 Uiso 1 1 calc R . . C23 C 0.9191(5) 0.2983(4) 0.3439(4) 0.0288(8) Uani 1 1 d . . . N23 N 0.9328(4) 0.1298(3) 0.3472(3) 0.0325(7) Uani 1 1 d . . . O23 O 0.8291(4) 0.0745(3) 0.4334(3) 0.0392(7) Uani 1 1 d . . . O24 O 1.0483(4) 0.0515(3) 0.2624(3) 0.0437(7) Uani 1 1 d . . . C24 C 1.0230(5) 0.3631(4) 0.2384(4) 0.0282(8) Uani 1 1 d . . . H24 H 1.1014 0.3026 0.1675 0.034 Uiso 1 1 calc R . . C25 C 1.0062(5) 0.5203(4) 0.2423(4) 0.0288(8) Uani 1 1 d . . . N25 N 1.1182(4) 0.5946(3) 0.1334(3) 0.0332(7) Uani 1 1 d . . . O25 O 1.2033(4) 0.5172(3) 0.0346(3) 0.0466(8) Uani 1 1 d . . . O26 O 1.1214(4) 0.7298(3) 0.1457(3) 0.0480(8) Uani 1 1 d . . . C26 C 0.8917(5) 0.6143(4) 0.3426(4) 0.0284(8) Uani 1 1 d . . . H26 H 0.8848 0.7228 0.3408 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0401(17) 0.0220(14) 0.0225(16) -0.0096(12) 0.0139(14) -0.0073(12) C12 0.0350(19) 0.0229(16) 0.0242(18) -0.0052(13) 0.0090(16) -0.0057(14) N12 0.046(2) 0.0276(15) 0.0304(19) -0.0082(13) 0.0151(15) -0.0137(14) C13 0.038(2) 0.0269(17) 0.0258(19) -0.0067(14) 0.0094(16) -0.0062(15) N14 0.0461(19) 0.0241(15) 0.0341(19) -0.0080(12) 0.0049(16) -0.0059(13) C15 0.047(2) 0.0187(15) 0.031(2) -0.0044(14) 0.0081(18) -0.0076(15) C16 0.041(2) 0.0263(17) 0.026(2) -0.0036(14) 0.0074(17) -0.0095(15) C21 0.0324(18) 0.0237(15) 0.0236(18) -0.0054(13) 0.0068(15) -0.0087(13) C27 0.042(2) 0.0244(16) 0.0243(19) -0.0067(13) 0.0118(16) -0.0118(15) O21 0.0559(17) 0.0230(12) 0.0315(15) -0.0094(10) 0.0192(13) -0.0079(12) O22 0.0499(16) 0.0259(12) 0.0311(15) -0.0092(10) 0.0220(13) -0.0117(11) C22 0.0339(19) 0.0259(16) 0.0275(19) -0.0021(13) 0.0082(16) -0.0140(14) C23 0.0354(19) 0.0188(15) 0.032(2) -0.0083(13) 0.0072(16) -0.0110(13) N23 0.0451(18) 0.0216(14) 0.0294(17) -0.0062(12) 0.0124(15) -0.0128(13) O23 0.0524(16) 0.0252(13) 0.0380(16) -0.0046(11) 0.0185(13) -0.0178(12) O24 0.0621(18) 0.0236(12) 0.0372(16) -0.0138(11) 0.0283(14) -0.0096(12) C24 0.0338(18) 0.0272(16) 0.0210(18) -0.0077(13) 0.0110(15) -0.0081(14) C25 0.038(2) 0.0230(16) 0.0244(19) -0.0044(13) 0.0095(16) -0.0118(14) N25 0.0457(18) 0.0232(14) 0.0287(17) -0.0044(12) 0.0153(15) -0.0142(13) O25 0.071(2) 0.0330(14) 0.0306(15) -0.0136(11) 0.0343(15) -0.0203(14) O26 0.068(2) 0.0245(13) 0.0469(18) -0.0099(12) 0.0283(15) -0.0194(13) C26 0.0366(19) 0.0194(15) 0.0274(19) -0.0064(13) 0.0092(16) -0.0089(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.339(4) . ? N11 C16 1.356(4) . ? N11 H11 0.97(4) . ? C12 N12 1.337(4) . ? C12 C13 1.416(5) . ? N12 H12A 0.84(5) . ? N12 H12B 0.92(5) . ? C13 N14 1.306(4) . ? C13 H13 0.9500 . ? N14 C15 1.366(5) . ? C15 C16 1.365(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.392(4) . ? C21 C26 1.396(5) . ? C21 C27 1.507(5) . ? C27 O22 1.248(4) . ? C27 O21 1.268(4) . ? C22 C23 1.381(5) . ? C22 H22 0.9500 . ? C23 C24 1.379(5) . ? C23 N23 1.471(4) . ? N23 O23 1.227(4) . ? N23 O24 1.232(4) . ? C24 C25 1.372(4) . ? C24 H24 0.9500 . ? C25 C26 1.390(5) . ? C25 N25 1.479(4) . ? N25 O26 1.224(4) . ? N25 O25 1.232(4) . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 121.0(3) . . ? C12 N11 H11 126(3) . . ? C16 N11 H11 113(3) . . ? N12 C12 N11 120.1(3) . . ? N12 C12 C13 123.0(3) . . ? N11 C12 C13 116.9(3) . . ? C12 N12 H12A 116(3) . . ? C12 N12 H12B 111(3) . . ? H12A N12 H12B 132(4) . . ? N14 C13 C12 123.7(3) . . ? N14 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C13 N14 C15 117.3(3) . . ? C16 C15 N14 121.6(3) . . ? C16 C15 H15 119.2 . . ? N14 C15 H15 119.2 . . ? N11 C16 C15 119.6(3) . . ? N11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C22 C21 C26 119.8(3) . . ? C22 C21 C27 120.1(3) . . ? C26 C21 C27 120.1(3) . . ? O22 C27 O21 127.0(3) . . ? O22 C27 C21 117.7(3) . . ? O21 C27 C21 115.3(3) . . ? C23 C22 C21 119.1(3) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C24 C23 C22 123.2(3) . . ? C24 C23 N23 118.7(3) . . ? C22 C23 N23 118.1(3) . . ? O23 N23 O24 123.5(3) . . ? O23 N23 C23 118.7(3) . . ? O24 N23 C23 117.8(3) . . ? C25 C24 C23 115.9(3) . . ? C25 C24 H24 122.0 . . ? C23 C24 H24 122.0 . . ? C24 C25 C26 124.2(3) . . ? C24 C25 N25 118.0(3) . . ? C26 C25 N25 117.8(3) . . ? O26 N25 O25 123.3(3) . . ? O26 N25 C25 118.5(3) . . ? O25 N25 C25 118.2(3) . . ? C25 C26 C21 117.8(3) . . ? C25 C26 H26 121.1 . . ? C21 C26 H26 121.1 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 -177.1(3) . . . . ? C16 N11 C12 C13 2.3(5) . . . . ? N12 C12 C13 N14 177.0(4) . . . . ? N11 C12 C13 N14 -2.4(6) . . . . ? C12 C13 N14 C15 0.5(6) . . . . ? C13 N14 C15 C16 1.5(5) . . . . ? C12 N11 C16 C15 -0.4(5) . . . . ? N14 C15 C16 N11 -1.6(6) . . . . ? C22 C21 C27 O22 6.1(5) . . . . ? C26 C21 C27 O22 -171.8(4) . . . . ? C22 C21 C27 O21 -175.1(3) . . . . ? C26 C21 C27 O21 7.0(5) . . . . ? C26 C21 C22 C23 0.8(5) . . . . ? C27 C21 C22 C23 -177.1(3) . . . . ? C21 C22 C23 C24 -1.8(6) . . . . ? C21 C22 C23 N23 179.1(3) . . . . ? C24 C23 N23 O23 -173.7(3) . . . . ? C22 C23 N23 O23 5.4(5) . . . . ? C24 C23 N23 O24 6.0(5) . . . . ? C22 C23 N23 O24 -174.8(3) . . . . ? C22 C23 C24 C25 1.8(5) . . . . ? N23 C23 C24 C25 -179.0(3) . . . . ? C23 C24 C25 C26 -0.9(5) . . . . ? C23 C24 C25 N25 178.6(3) . . . . ? C24 C25 N25 O26 -171.1(3) . . . . ? C26 C25 N25 O26 8.4(5) . . . . ? C24 C25 N25 O25 9.1(5) . . . . ? C26 C25 N25 O25 -171.4(3) . . . . ? C24 C25 C26 C21 0.0(6) . . . . ? N25 C25 C26 C21 -179.5(3) . . . . ? C22 C21 C26 C25 0.1(5) . . . . ? C27 C21 C26 C25 178.0(3) . . . . ? 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_site_symmetry_A N11 H11 O21 0.97(4) 1.61(4) 2.573(4) 169(4) . N12 H12A O22 0.84(5) 1.95(5) 2.790(4) 178(4) . N12 H12B O25 0.92(5) 2.39(4) 3.096(4) 133(3) 1_456 N12 H12B O26 0.92(5) 2.29(5) 3.187(5) 166(4) 1_456 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 29.69 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.618 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.135 #END data_B1.A16 _database_code_depnum_ccdc_archive 'CCDC 876778' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; P55 2-aminopyrazine, 3-NO2-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3) (C7 H5 N O4)2 ; _chemical_formula_sum 'C18 H15 N5 O8' _chemical_formula_weight 429.35 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 5.9930(10) _cell_length_b 12.1894(18) _cell_length_c 12.995(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.803(8) _cell_angle_gamma 90.00 _cell_volume 938.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3048 _cell_measurement_theta_min 3.17 _cell_measurement_theta_max 31.42 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.520 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9572 _exptl_absorpt_correction_T_max 0.9855 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8709 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 31.56 _reflns_number_total 3078 _reflns_number_gt 2239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0050P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3078 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1511 _refine_ls_wR_factor_gt 0.1387 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C11 C 1.17490(18) 0.37229(9) 0.64923(8) 0.0292(2) Uani 1 1 d . . . C17 C 1.06082(18) 0.26467(9) 0.62613(8) 0.0308(2) Uani 1 1 d . . . O11 O 0.85528(14) 0.27284(8) 0.57531(7) 0.0363(2) Uani 1 1 d . . . H11 H 0.788(2) 0.2012(14) 0.5632(11) 0.044 Uiso 1 1 d . . . O12 O 1.15209(14) 0.17780(7) 0.65255(7) 0.0395(2) Uani 1 1 d . . . C12 C 1.05749(18) 0.47026(9) 0.63017(8) 0.0279(2) Uani 1 1 d . . . H12 H 0.9026 0.4707 0.6002 0.033 Uiso 1 1 calc R . . C13 C 1.17230(18) 0.56722(9) 0.65606(8) 0.0292(2) Uani 1 1 d . . . N13 N 1.04633(17) 0.67040(8) 0.63882(8) 0.0325(2) Uani 1 1 d . . . O13 O 0.84882(14) 0.66582(7) 0.59867(7) 0.0398(2) Uani 1 1 d . . . O14 O 1.14467(15) 0.75633(7) 0.66543(7) 0.0441(3) Uani 1 1 d . . . C14 C 1.39721(19) 0.57086(10) 0.69814(10) 0.0354(3) Uani 1 1 d . . . H14 H 1.4717 0.6388 0.7146 0.042 Uiso 1 1 calc R . . C15 C 1.51144(19) 0.47244(10) 0.71571(11) 0.0390(3) Uani 1 1 d . . . H15 H 1.6668 0.4725 0.7448 0.047 Uiso 1 1 calc R . . C16 C 1.40210(19) 0.37418(11) 0.69142(10) 0.0355(3) Uani 1 1 d . . . H16 H 1.4829 0.3072 0.7037 0.043 Uiso 1 1 calc R . . N21 N 0.64062(17) 0.08826(8) 0.52820(8) 0.0348(2) Uani 1 1 d . . . C22A C 0.7091(2) -0.01505(10) 0.55270(10) 0.0346(3) Uani 0.50 1 d P A 1 N22 N 0.9039(3) -0.03054(18) 0.60095(17) 0.0336(4) Uani 0.50 1 d P A 1 H22A H 0.991(5) 0.024(3) 0.622(2) 0.040 Uiso 0.50 1 d P B 1 H22B H 0.939(5) -0.098(3) 0.609(2) 0.040 Uiso 0.50 1 d P C 1 C22B C 0.7091(2) -0.01505(10) 0.55270(10) 0.0346(3) Uani 0.50 1 d P A 2 H22 H 0.8558 -0.0281 0.5900 0.042 Uiso 0.50 1 calc PR A 2 C23 C 0.5652(2) -0.10221(10) 0.52349(10) 0.0366(3) Uani 1 1 d . . . H23 H 0.6161 -0.1746 0.5412 0.044 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C11 0.0306(5) 0.0291(6) 0.0277(5) 0.0010(4) 0.0044(4) 0.0011(4) C17 0.0331(5) 0.0308(6) 0.0288(5) 0.0011(4) 0.0054(4) 0.0024(4) O11 0.0327(4) 0.0297(4) 0.0440(5) 0.0018(4) -0.0019(3) -0.0012(3) O12 0.0397(5) 0.0286(4) 0.0484(5) 0.0019(4) 0.0014(4) 0.0053(3) C12 0.0267(5) 0.0302(6) 0.0256(5) 0.0014(4) 0.0006(4) 0.0001(4) C13 0.0329(5) 0.0281(5) 0.0264(5) 0.0007(4) 0.0037(4) 0.0006(4) N13 0.0380(5) 0.0283(5) 0.0307(5) 0.0013(4) 0.0033(4) -0.0001(4) O13 0.0365(5) 0.0358(5) 0.0451(5) 0.0036(4) 0.0001(4) 0.0050(3) O14 0.0539(6) 0.0280(5) 0.0484(5) -0.0027(4) 0.0011(4) -0.0049(4) C14 0.0330(6) 0.0346(6) 0.0379(6) -0.0015(5) 0.0032(4) -0.0050(4) C15 0.0245(5) 0.0448(7) 0.0460(7) 0.0009(5) 0.0000(5) -0.0005(4) C16 0.0308(6) 0.0357(6) 0.0395(6) 0.0040(5) 0.0037(4) 0.0056(4) N21 0.0384(5) 0.0286(5) 0.0383(5) -0.0006(4) 0.0093(4) -0.0012(4) C22A 0.0359(6) 0.0320(6) 0.0366(6) 0.0005(5) 0.0078(5) 0.0010(4) N22 0.0273(9) 0.0283(10) 0.0423(11) 0.0025(8) -0.0038(8) 0.0009(7) C22B 0.0359(6) 0.0320(6) 0.0366(6) 0.0005(5) 0.0078(5) 0.0010(4) C23 0.0423(6) 0.0280(6) 0.0406(6) 0.0019(5) 0.0102(5) 0.0026(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C11 C16 1.3880(15) . ? C11 C12 1.3890(15) . ? C11 C17 1.4885(16) . ? C17 O12 1.2169(14) . ? C17 O11 1.3093(14) . ? O11 H11 0.965(17) . ? C12 C13 1.3830(15) . ? C12 H12 0.9500 . ? C13 C14 1.3755(16) . ? C13 N13 1.4663(15) . ? N13 O13 1.2196(13) . ? N13 O14 1.2254(13) . ? C14 C15 1.3828(17) . ? C14 H14 0.9500 . ? C15 C16 1.3785(18) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N21 C23 1.3221(16) 3_656 ? N21 C22A 1.3474(16) . ? C22A N22 1.252(2) . ? C22A C23 1.3842(18) . ? N22 H22A 0.86(3) . ? N22 H22B 0.85(3) . ? C23 N21 1.3221(16) 3_656 ? C23 H23 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 C11 C12 119.72(11) . . ? C16 C11 C17 119.13(10) . . ? C12 C11 C17 121.15(10) . . ? O12 C17 O11 123.78(11) . . ? O12 C17 C11 122.49(10) . . ? O11 C17 C11 113.73(9) . . ? C17 O11 H11 110.7(8) . . ? C13 C12 C11 118.15(10) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? C14 C13 C12 123.03(11) . . ? C14 C13 N13 118.90(10) . . ? C12 C13 N13 118.06(10) . . ? O13 N13 O14 123.58(10) . . ? O13 N13 C13 118.00(9) . . ? O14 N13 C13 118.42(10) . . ? C13 C14 C15 117.90(11) . . ? C13 C14 H14 121.1 . . ? C15 C14 H14 121.1 . . ? C16 C15 C14 120.67(11) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 120.53(11) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C23 N21 C22A 117.83(11) 3_656 . ? N22 C22A N21 119.08(15) . . ? N22 C22A C23 121.04(15) . . ? N21 C22A C23 119.88(12) . . ? C22A N22 H22A 121(2) . . ? C22A N22 H22B 114.0(19) . . ? H22A N22 H22B 125(3) . . ? N21 C23 C22A 122.29(12) 3_656 . ? N21 C23 H23 118.9 3_656 . ? C22A C23 H23 118.9 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 C11 C17 O12 7.78(16) . . . . ? C12 C11 C17 O12 -171.62(11) . . . . ? C16 C11 C17 O11 -172.26(9) . . . . ? C12 C11 C17 O11 8.34(15) . . . . ? C16 C11 C12 C13 -1.13(16) . . . . ? C17 C11 C12 C13 178.27(9) . . . . ? C11 C12 C13 C14 1.02(17) . . . . ? C11 C12 C13 N13 -178.18(9) . . . . ? C14 C13 N13 O13 177.91(9) . . . . ? C12 C13 N13 O13 -2.85(15) . . . . ? C14 C13 N13 O14 -2.10(16) . . . . ? C12 C13 N13 O14 177.13(9) . . . . ? C12 C13 C14 C15 -0.50(18) . . . . ? N13 C13 C14 C15 178.69(10) . . . . ? C13 C14 C15 C16 0.10(19) . . . . ? C14 C15 C16 C11 -0.25(19) . . . . ? C12 C11 C16 C15 0.77(17) . . . . ? C17 C11 C16 C15 -178.64(10) . . . . ? C23 N21 C22A N22 179.46(14) 3_656 . . . ? C23 N21 C22A C23 0.15(19) 3_656 . . . ? N22 C22A C23 N21 -179.45(14) . . . 3_656 ? N21 C22A C23 N21 -0.2(2) . . . 3_656 ? 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_site_symmetry_A O11 H11 N21 0.965(17) 1.660(17) 2.6174(14) 170.7(14) . N22 H22A O12 0.86(3) 2.12(3) 2.967(2) 167(3) . N22 H22B O14 0.85(3) 2.22(3) 3.027(2) 158(3) 1_545 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 31.56 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.401 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.052 #END data_B1.A23 _database_code_depnum_ccdc_archive 'CCDC 876779' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; D3 2-aminopyrazine, HOOC-(CH2)2-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3)2 (C4 H6 O4) ; _chemical_formula_sum 'C12 H16 N6 O4' _chemical_formula_weight 308.31 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 5.3982(9) _cell_length_b 19.505(3) _cell_length_c 6.9524(12) _cell_angle_alpha 90.00 _cell_angle_beta 104.487(10) _cell_angle_gamma 90.00 _cell_volume 708.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2227 _cell_measurement_theta_min 3.20 _cell_measurement_theta_max 30.32 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12115 _diffrn_reflns_av_R_equivalents 0.1043 _diffrn_reflns_av_sigmaI/netI 0.0977 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 30.50 _reflns_number_total 2141 _reflns_number_gt 1230 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2141 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2198 _refine_ls_R_factor_gt 0.1548 _refine_ls_wR_factor_ref 0.2946 _refine_ls_wR_factor_gt 0.2756 _refine_ls_goodness_of_fit_ref 1.486 _refine_ls_restrained_S_all 1.486 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.6018(5) 0.08821(14) 0.5302(4) 0.0266(8) Uani 1 1 d . . . C12 C 0.3657(7) 0.10545(18) 0.4255(5) 0.0242(8) Uani 1 1 d . . . N12 N 0.1922(6) 0.05547(16) 0.3647(5) 0.0336(9) Uani 1 1 d . . . H12A H 0.242(8) 0.015(2) 0.390(6) 0.040 Uiso 1 1 d . . . H12B H 0.050(8) 0.066(2) 0.281(6) 0.040 Uiso 1 1 d . . . C13 C 0.3022(7) 0.17506(18) 0.3816(5) 0.0282(9) Uani 1 1 d . . . H13 H 0.1352 0.1862 0.3054 0.034 Uiso 1 1 calc R . . N14 N 0.4678(6) 0.22473(15) 0.4432(5) 0.0289(8) Uani 1 1 d . . . C15 C 0.7044(7) 0.20699(19) 0.5484(6) 0.0318(9) Uani 1 1 d . . . H15 H 0.8293 0.2416 0.5939 0.038 Uiso 1 1 calc R . . C16 C 0.7665(7) 0.13972(18) 0.5904(6) 0.0298(9) Uani 1 1 d . . . H16 H 0.9345 0.1291 0.6658 0.036 Uiso 1 1 calc R . . C21 C 0.5094(7) 0.40106(17) 0.4812(5) 0.0256(9) Uani 1 1 d . . . O21 O 0.3398(5) 0.35538(12) 0.3892(4) 0.0312(7) Uani 1 1 d . . . H21 H 0.405(8) 0.311(2) 0.419(6) 0.037 Uiso 1 1 d . . . O22 O 0.7205(5) 0.38601(12) 0.5842(4) 0.0321(7) Uani 1 1 d . . . C22 C 0.4110(7) 0.47338(17) 0.4401(5) 0.0254(9) Uani 1 1 d . . . H22A H 0.2420 0.4770 0.4709 0.031 Uiso 1 1 calc R . . H22B H 0.3865 0.4833 0.2969 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0160(16) 0.0207(15) 0.0358(18) -0.0001(13) -0.0070(13) 0.0015(12) C12 0.0165(18) 0.0234(18) 0.0281(18) -0.0022(14) -0.0030(15) 0.0002(14) N12 0.0184(17) 0.0171(15) 0.052(2) 0.0036(14) -0.0156(15) 0.0037(14) C13 0.0190(19) 0.0224(18) 0.035(2) 0.0015(15) -0.0083(16) 0.0018(15) N14 0.0227(17) 0.0206(15) 0.0370(18) 0.0001(13) -0.0045(14) -0.0010(13) C15 0.0189(19) 0.0246(18) 0.043(2) -0.0022(17) -0.0086(17) -0.0025(16) C16 0.018(2) 0.0258(18) 0.038(2) 0.0003(16) -0.0076(16) 0.0033(15) C21 0.020(2) 0.0237(18) 0.0285(19) 0.0002(15) -0.0021(16) -0.0002(15) O21 0.0219(15) 0.0157(12) 0.0452(16) -0.0007(11) -0.0118(12) -0.0014(11) O22 0.0185(13) 0.0202(13) 0.0459(16) -0.0019(11) -0.0136(12) 0.0023(11) C22 0.0176(18) 0.0193(16) 0.0328(19) -0.0006(15) -0.0061(15) 0.0018(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.337(5) . ? N11 C12 1.343(5) . ? C12 N12 1.345(5) . ? C12 C13 1.415(5) . ? N12 H12A 0.85(5) . ? N12 H12B 0.86(4) . ? C13 N14 1.315(5) . ? C13 H13 0.9500 . ? N14 C15 1.349(5) . ? C15 C16 1.367(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 O22 1.220(4) . ? C21 O21 1.322(4) . ? C21 C22 1.509(5) . ? O21 H21 0.93(4) . ? C22 C22 1.515(7) 3_666 ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 116.6(3) . . ? N11 C12 N12 118.7(3) . . ? N11 C12 C13 120.2(3) . . ? N12 C12 C13 121.1(3) . . ? C12 N12 H12A 117(3) . . ? C12 N12 H12B 118(3) . . ? H12A N12 H12B 123(4) . . ? N14 C13 C12 121.9(3) . . ? N14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 N14 C15 117.5(3) . . ? N14 C15 C16 120.7(3) . . ? N14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? N11 C16 C15 123.1(3) . . ? N11 C16 H16 118.5 . . ? C15 C16 H16 118.5 . . ? O22 C21 O21 123.6(3) . . ? O22 C21 C22 124.7(3) . . ? O21 C21 C22 111.7(3) . . ? C21 O21 H21 110(3) . . ? C21 C22 C22 113.1(4) . 3_666 ? C21 C22 H22A 109.0 . . ? C22 C22 H22A 109.0 3_666 . ? C21 C22 H22B 109.0 . . ? C22 C22 H22B 109.0 3_666 . ? H22A C22 H22B 107.8 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 -178.9(3) . . . . ? C16 N11 C12 C13 0.9(5) . . . . ? N11 C12 C13 N14 -1.1(6) . . . . ? N12 C12 C13 N14 178.6(4) . . . . ? C12 C13 N14 C15 1.0(6) . . . . ? C13 N14 C15 C16 -0.7(6) . . . . ? C12 N11 C16 C15 -0.6(6) . . . . ? N14 C15 C16 N11 0.5(6) . . . . ? O22 C21 C22 C22 -6.8(6) . . . 3_666 ? O21 C21 C22 C22 174.0(4) . . . 3_666 ? 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_site_symmetry_A O21 H21 N14 0.93(4) 1.72(4) 2.643(4) 168(4) . N12 H12A N11 0.85(5) 2.19(5) 3.036(4) 176(4) 3_656 N12 H12B O22 0.86(4) 2.17(5) 3.018(4) 168(4) 4_465 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.736 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.157 #END data_B1.A24 _database_code_depnum_ccdc_archive 'CCDC 876780' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; D8 2-aminopyrazine, HOOC-(CH2)3-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3) (C5 H8 O4) ; _chemical_formula_sum 'C9 H13 N3 O4' _chemical_formula_weight 227.22 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 5.2487(3) _cell_length_b 29.2633(18) _cell_length_c 7.2357(5) _cell_angle_alpha 90.00 _cell_angle_beta 104.958(3) _cell_angle_gamma 90.00 _cell_volume 1073.70(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3517 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 32.53 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10113 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 32.02 _reflns_number_total 3662 _reflns_number_gt 2548 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3662 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0707 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1459 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.5284(2) 0.63776(3) 0.28266(15) 0.0419(2) Uani 1 1 d . . . C12 C 0.7652(2) 0.64913(4) 0.38976(17) 0.0381(2) Uani 1 1 d . . . N12 N 0.9424(2) 0.61615(4) 0.45322(19) 0.0528(3) Uani 1 1 d . . . H12A H 0.902(3) 0.5866(7) 0.422(2) 0.063 Uiso 1 1 d . . . H12B H 1.089(4) 0.6232(7) 0.524(3) 0.063 Uiso 1 1 d . . . C13 C 0.8263(2) 0.69549(4) 0.43246(19) 0.0450(3) Uani 1 1 d . . . H13 H 0.9920 0.7031 0.5091 0.054 Uiso 1 1 calc R . . N14 N 0.6560(2) 0.72807(3) 0.36709(18) 0.0499(3) Uani 1 1 d . . . C15 C 0.4194(3) 0.71620(4) 0.2577(2) 0.0536(3) Uani 1 1 d . . . H15 H 0.2955 0.7387 0.2083 0.064 Uiso 1 1 calc R . . C16 C 0.3576(2) 0.67156(4) 0.2180(2) 0.0494(3) Uani 1 1 d . . . H16 H 0.1903 0.6643 0.1431 0.059 Uiso 1 1 calc R . . C21 C 0.4446(2) 0.51950(4) 0.24735(18) 0.0430(3) Uani 1 1 d . . . O21 O 0.2959(2) 0.55605(3) 0.20216(17) 0.0625(3) Uani 1 1 d . . . H21 H 0.387(4) 0.5829(7) 0.233(3) 0.075 Uiso 1 1 d . . . O22 O 0.6750(2) 0.52138(3) 0.32653(17) 0.0636(3) Uani 1 1 d . . . C22 C 0.2906(2) 0.47694(4) 0.18588(19) 0.0460(3) Uani 1 1 d . . . H22A H 0.2136 0.4786 0.0489 0.055 Uiso 1 1 calc R . . H22B H 0.1465 0.4760 0.2470 0.055 Uiso 1 1 calc R . . C23 C 0.4425(2) 0.43271(4) 0.22925(18) 0.0432(3) Uani 1 1 d . . . H23A H 0.4938 0.4275 0.3663 0.052 Uiso 1 1 calc R . . H23B H 0.6012 0.4344 0.1844 0.052 Uiso 1 1 calc R . . C24 C 0.2701(2) 0.39395(4) 0.13017(18) 0.0428(3) Uani 1 1 d . . . H24A H 0.1049 0.3950 0.1667 0.051 Uiso 1 1 calc R . . H24B H 0.2300 0.3991 -0.0068 0.051 Uiso 1 1 calc R . . C25 C 0.3828(2) 0.34706(4) 0.17072(17) 0.0399(2) Uani 1 1 d . . . O25 O 0.22094(19) 0.31586(3) 0.07598(16) 0.0567(3) Uani 1 1 d . . . H25 H 0.292(4) 0.2857(7) 0.099(3) 0.068 Uiso 1 1 d . . . O26 O 0.59359(19) 0.33797(3) 0.27691(15) 0.0567(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0399(5) 0.0284(4) 0.0523(6) -0.0017(4) 0.0024(4) -0.0029(4) C12 0.0386(5) 0.0286(5) 0.0444(6) -0.0006(4) 0.0059(4) -0.0008(4) N12 0.0430(6) 0.0340(5) 0.0724(8) 0.0007(5) -0.0013(5) 0.0042(4) C13 0.0413(6) 0.0315(5) 0.0562(7) -0.0045(5) 0.0020(5) -0.0038(4) N14 0.0517(6) 0.0277(5) 0.0653(7) -0.0018(4) 0.0061(5) -0.0009(4) C15 0.0475(7) 0.0324(6) 0.0732(9) 0.0043(5) 0.0015(6) 0.0066(5) C16 0.0378(6) 0.0378(6) 0.0640(8) 0.0023(5) -0.0027(5) 0.0002(5) C21 0.0447(6) 0.0298(5) 0.0501(6) -0.0032(4) 0.0045(5) 0.0003(4) O21 0.0510(5) 0.0264(4) 0.0952(8) -0.0036(4) -0.0084(5) -0.0007(4) O22 0.0452(5) 0.0407(5) 0.0934(8) -0.0068(5) -0.0029(5) -0.0015(4) C22 0.0447(6) 0.0280(5) 0.0573(7) -0.0029(5) -0.0010(5) 0.0010(4) C23 0.0441(6) 0.0287(5) 0.0504(6) -0.0027(4) 0.0006(5) 0.0023(4) C24 0.0444(6) 0.0274(5) 0.0493(6) -0.0027(4) -0.0009(4) 0.0043(4) C25 0.0405(6) 0.0289(5) 0.0453(6) -0.0002(4) 0.0019(4) 0.0017(4) O25 0.0506(5) 0.0274(4) 0.0766(7) -0.0034(4) -0.0119(4) 0.0012(3) O26 0.0479(5) 0.0365(4) 0.0705(6) -0.0017(4) -0.0120(4) 0.0053(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.3264(15) . ? N11 C16 1.3357(16) . ? C12 N12 1.3367(15) . ? C12 C13 1.4099(15) . ? N12 H12A 0.906(19) . ? N12 H12B 0.835(19) . ? C13 N14 1.3088(16) . ? C13 H13 0.9300 . ? N14 C15 1.3351(18) . ? C15 C16 1.3587(18) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 O22 1.1982(15) . ? C21 O21 1.3146(15) . ? C21 C22 1.4888(16) . ? O21 H21 0.91(2) . ? C22 C23 1.5100(16) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.5116(16) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.4928(15) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 O26 1.2027(14) . ? C25 O25 1.3133(14) . ? O25 H25 0.956(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 117.51(10) . . ? N11 C12 N12 118.92(10) . . ? N11 C12 C13 119.69(10) . . ? N12 C12 C13 121.38(11) . . ? C12 N12 H12A 120.5(11) . . ? C12 N12 H12B 118.8(13) . . ? H12A N12 H12B 120.6(17) . . ? N14 C13 C12 121.75(11) . . ? N14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 N14 C15 117.95(11) . . ? N14 C15 C16 120.68(11) . . ? N14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? N11 C16 C15 122.41(12) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? O22 C21 O21 122.85(11) . . ? O22 C21 C22 125.76(11) . . ? O21 C21 C22 111.39(10) . . ? C21 O21 H21 113.6(13) . . ? C21 C22 C23 115.97(10) . . ? C21 C22 H22A 108.3 . . ? C23 C22 H22A 108.3 . . ? C21 C22 H22B 108.3 . . ? C23 C22 H22B 108.3 . . ? H22A C22 H22B 107.4 . . ? C22 C23 C24 108.98(9) . . ? C22 C23 H23A 109.9 . . ? C24 C23 H23A 109.9 . . ? C22 C23 H23B 109.9 . . ? C24 C23 H23B 109.9 . . ? H23A C23 H23B 108.3 . . ? C25 C24 C23 115.99(10) . . ? C25 C24 H24A 108.3 . . ? C23 C24 H24A 108.3 . . ? C25 C24 H24B 108.3 . . ? C23 C24 H24B 108.3 . . ? H24A C24 H24B 107.4 . . ? O26 C25 O25 122.96(11) . . ? O26 C25 C24 125.55(10) . . ? O25 C25 C24 111.48(10) . . ? C25 O25 H25 112.5(12) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 -178.60(13) . . . . ? C16 N11 C12 C13 0.65(18) . . . . ? N11 C12 C13 N14 -0.9(2) . . . . ? N12 C12 C13 N14 178.35(13) . . . . ? C12 C13 N14 C15 0.2(2) . . . . ? C13 N14 C15 C16 0.8(2) . . . . ? C12 N11 C16 C15 0.2(2) . . . . ? N14 C15 C16 N11 -1.0(2) . . . . ? O22 C21 C22 C23 0.2(2) . . . . ? O21 C21 C22 C23 179.53(12) . . . . ? C21 C22 C23 C24 -170.90(12) . . . . ? C22 C23 C24 C25 -175.32(12) . . . . ? C23 C24 C25 O26 1.5(2) . . . . ? C23 C24 C25 O25 -178.93(12) . . . . ? 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_site_symmetry_A N12 H12A O22 0.906(19) 2.261(19) 3.1366(16) 162.3(15) . N12 H12B O26 0.835(19) 2.21(2) 3.0153(15) 161.5(18) 3_766 O21 H21 N11 0.91(2) 1.77(2) 2.6792(13) 173.7(19) . O25 H25 N14 0.956(19) 1.72(2) 2.6551(13) 166.7(17) 2_645 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 32.02 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.247 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.049 #END data_B1.A26 _database_code_depnum_ccdc_archive 'CCDC 876781' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; D9 2-aminopyrazine, HOOC-(CH2)5-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3) (C7 H12 O4) ; _chemical_formula_sum 'C11 H17 N3 O4' _chemical_formula_weight 255.28 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 5.0231(5) _cell_length_b 34.308(3) _cell_length_c 7.4377(8) _cell_angle_alpha 90.00 _cell_angle_beta 102.850(5) _cell_angle_gamma 90.00 _cell_volume 1249.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6761 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 32.59 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15680 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -51 _diffrn_reflns_limit_k_max 51 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 32.57 _reflns_number_total 4480 _reflns_number_gt 3370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4480 _refine_ls_number_parameters 179 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.52498(17) 0.34435(2) 0.30554(13) 0.02297(18) Uani 1 1 d . . . C12 C 0.76334(19) 0.33476(3) 0.41596(14) 0.02059(19) Uani 1 1 d . . . N12 N 0.94082(19) 0.36314(2) 0.48335(15) 0.0283(2) Uani 1 1 d . . . H12A H 0.897(3) 0.3886(5) 0.449(2) 0.039(4) Uiso 1 1 d . . . H12B H 1.101(4) 0.3570(5) 0.560(3) 0.052(5) Uiso 1 1 d . . . C13 C 0.8245(2) 0.29506(3) 0.45854(16) 0.0251(2) Uani 1 1 d . . . H13 H 0.9938 0.2885 0.5384 0.030 Uiso 1 1 calc R . . N14 N 0.65328(19) 0.26709(2) 0.39056(14) 0.0276(2) Uani 1 1 d . . . C15 C 0.4146(2) 0.27705(3) 0.27829(18) 0.0302(2) Uani 1 1 d . . . H15 H 0.2877 0.2574 0.2264 0.036 Uiso 1 1 calc R . . C16 C 0.3532(2) 0.31536(3) 0.23824(17) 0.0282(2) Uani 1 1 d . . . H16 H 0.1822 0.3216 0.1597 0.034 Uiso 1 1 calc R . . C21 C 0.4610(2) 0.44470(3) 0.27211(15) 0.0225(2) Uani 1 1 d . . . O21 O 0.30296(17) 0.41417(2) 0.22034(13) 0.0349(2) Uani 1 1 d . . . H21 H 0.401(4) 0.3908(5) 0.255(3) 0.058(5) Uiso 1 1 d . . . O22 O 0.69720(16) 0.44225(2) 0.35297(13) 0.0312(2) Uani 1 1 d . . . C22 C 0.3107(2) 0.48218(3) 0.21970(16) 0.0240(2) Uani 1 1 d . . . H22A H 0.1673 0.4845 0.2914 0.029 Uiso 1 1 calc R . . H22B H 0.2177 0.4807 0.0877 0.029 Uiso 1 1 calc R . . C23 C 0.4820(2) 0.51879(3) 0.24919(15) 0.0233(2) Uani 1 1 d . . . H23A H 0.6362 0.5161 0.1872 0.028 Uiso 1 1 calc R . . H23B H 0.5584 0.5225 0.3827 0.028 Uiso 1 1 calc R . . C24 C 0.3120(2) 0.55410(3) 0.17272(15) 0.0242(2) Uani 1 1 d . . . H24A H 0.2466 0.5507 0.0379 0.029 Uiso 1 1 calc R . . H24B H 0.1495 0.5550 0.2273 0.029 Uiso 1 1 calc R . . C25 C 0.4591(2) 0.59294(3) 0.20779(15) 0.0231(2) Uani 1 1 d . . . H25A H 0.5057 0.5984 0.3419 0.028 Uiso 1 1 calc R . . H25B H 0.6312 0.5918 0.1640 0.028 Uiso 1 1 calc R . . C26 C 0.2804(2) 0.62543(3) 0.10831(15) 0.0237(2) Uani 1 1 d . . . H26A H 0.2511 0.6208 -0.0261 0.028 Uiso 1 1 calc R . . H26B H 0.1000 0.6238 0.1408 0.028 Uiso 1 1 calc R . . C27 C 0.3885(2) 0.66597(3) 0.14838(15) 0.0222(2) Uani 1 1 d . . . O27 O 0.22284(16) 0.69220(2) 0.05356(13) 0.0318(2) Uani 1 1 d . . . H27 H 0.288(4) 0.7190(6) 0.083(3) 0.074(6) Uiso 1 1 d . . . O28 O 0.59968(16) 0.67442(2) 0.25528(12) 0.0316(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0206(4) 0.0168(3) 0.0288(5) -0.0004(3) -0.0002(3) 0.0010(3) C12 0.0196(4) 0.0154(3) 0.0254(5) 0.0002(3) 0.0022(3) 0.0009(3) N12 0.0222(4) 0.0175(3) 0.0399(6) -0.0007(3) -0.0045(4) -0.0015(3) C13 0.0221(4) 0.0168(4) 0.0330(6) 0.0015(4) -0.0007(4) 0.0020(3) N14 0.0263(4) 0.0163(3) 0.0372(5) 0.0001(3) 0.0011(4) -0.0008(3) C15 0.0253(5) 0.0188(4) 0.0419(7) -0.0032(4) -0.0021(4) -0.0033(4) C16 0.0218(5) 0.0219(4) 0.0360(6) -0.0022(4) -0.0042(4) 0.0000(3) C21 0.0253(5) 0.0163(4) 0.0253(5) 0.0014(3) 0.0044(4) 0.0007(3) O21 0.0292(4) 0.0149(3) 0.0534(6) 0.0009(3) -0.0061(4) 0.0002(3) O22 0.0249(4) 0.0207(3) 0.0444(5) 0.0026(3) -0.0001(3) 0.0018(3) C22 0.0246(5) 0.0156(4) 0.0291(5) 0.0021(3) 0.0000(4) 0.0014(3) C23 0.0244(5) 0.0163(4) 0.0273(5) 0.0020(3) 0.0018(4) 0.0005(3) C24 0.0245(5) 0.0149(4) 0.0304(5) 0.0024(3) -0.0001(4) -0.0006(3) C25 0.0219(4) 0.0163(4) 0.0285(5) 0.0023(3) 0.0001(4) -0.0009(3) C26 0.0234(4) 0.0157(4) 0.0284(5) 0.0019(3) -0.0019(4) -0.0017(3) C27 0.0200(4) 0.0171(4) 0.0272(5) 0.0009(3) 0.0005(3) -0.0003(3) O27 0.0269(4) 0.0153(3) 0.0449(5) 0.0022(3) -0.0099(3) 0.0001(3) O28 0.0262(4) 0.0206(3) 0.0406(5) 0.0016(3) -0.0084(3) -0.0026(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.3337(13) . ? N11 C16 1.3385(13) . ? C12 N12 1.3397(12) . ? C12 C13 1.4165(13) . ? N12 H12A 0.925(16) . ? N12 H12B 0.901(19) . ? C13 N14 1.3124(13) . ? C13 H13 0.9500 . ? N14 C15 1.3438(14) . ? C15 C16 1.3676(14) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 O22 1.2081(13) . ? C21 O21 1.3190(12) . ? C21 C22 1.4979(13) . ? O21 H21 0.947(19) . ? C22 C23 1.5108(13) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.5179(13) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.5176(12) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.5169(13) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.4988(13) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 O28 1.2109(12) . ? C27 O27 1.3186(12) . ? O27 H27 0.98(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 117.57(8) . . ? N11 C12 N12 118.87(8) . . ? N11 C12 C13 119.67(8) . . ? N12 C12 C13 121.46(9) . . ? C12 N12 H12A 119.0(9) . . ? C12 N12 H12B 119.4(12) . . ? H12A N12 H12B 121.5(15) . . ? N14 C13 C12 121.73(9) . . ? N14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C13 N14 C15 118.10(9) . . ? N14 C15 C16 120.43(9) . . ? N14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? N11 C16 C15 122.49(10) . . ? N11 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? O22 C21 O21 123.41(9) . . ? O22 C21 C22 124.87(9) . . ? O21 C21 C22 111.72(9) . . ? C21 O21 H21 110.5(11) . . ? C21 C22 C23 115.98(8) . . ? C21 C22 H22A 108.3 . . ? C23 C22 H22A 108.3 . . ? C21 C22 H22B 108.3 . . ? C23 C22 H22B 108.3 . . ? H22A C22 H22B 107.4 . . ? C22 C23 C24 110.76(8) . . ? C22 C23 H23A 109.5 . . ? C24 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23B 109.5 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C23 115.11(8) . . ? C25 C24 H24A 108.5 . . ? C23 C24 H24A 108.5 . . ? C25 C24 H24B 108.5 . . ? C23 C24 H24B 108.5 . . ? H24A C24 H24B 107.5 . . ? C26 C25 C24 110.40(8) . . ? C26 C25 H25A 109.6 . . ? C24 C25 H25A 109.6 . . ? C26 C25 H25B 109.6 . . ? C24 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? C27 C26 C25 115.85(8) . . ? C27 C26 H26A 108.3 . . ? C25 C26 H26A 108.3 . . ? C27 C26 H26B 108.3 . . ? C25 C26 H26B 108.3 . . ? H26A C26 H26B 107.4 . . ? O28 C27 O27 122.98(9) . . ? O28 C27 C26 125.34(9) . . ? O27 C27 C26 111.68(8) . . ? C27 O27 H27 112.3(13) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 179.11(10) . . . . ? C16 N11 C12 C13 -0.49(16) . . . . ? N11 C12 C13 N14 0.71(17) . . . . ? N12 C12 C13 N14 -178.88(11) . . . . ? C12 C13 N14 C15 -0.18(17) . . . . ? C13 N14 C15 C16 -0.52(18) . . . . ? C12 N11 C16 C15 -0.21(18) . . . . ? N14 C15 C16 N11 0.8(2) . . . . ? O22 C21 C22 C23 8.50(17) . . . . ? O21 C21 C22 C23 -171.98(10) . . . . ? C21 C22 C23 C24 174.11(9) . . . . ? C22 C23 C24 C25 175.64(9) . . . . ? C23 C24 C25 C26 173.97(9) . . . . ? C24 C25 C26 C27 173.39(9) . . . . ? C25 C26 C27 O28 -1.91(17) . . . . ? C25 C26 C27 O27 178.79(10) . . . . ? 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_site_symmetry_A O21 H21 N11 0.947(19) 1.721(19) 2.6588(11) 170.0(17) . N12 H12A O22 0.925(16) 2.140(16) 3.0459(12) 166.2(13) . N12 H12B O28 0.901(19) 2.10(2) 2.9616(13) 160.9(16) 3_766 O27 H27 N14 0.98(2) 1.68(2) 2.6544(11) 170(2) 2_655 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 32.57 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.421 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.049 #END data_B1.A27 _database_code_depnum_ccdc_archive 'CCDC 876782' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; D5 2-aminopyrazine, HOOC-(CH2)6-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3) (C8 H14 O4) ; _chemical_formula_sum 'C12 H19 N3 O4' _chemical_formula_weight 269.30 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7749(5) _cell_length_b 9.8014(7) _cell_length_c 9.2097(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.560(3) _cell_angle_gamma 90.00 _cell_volume 687.59(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2827 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 31.56 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9654 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8690 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 33.15 _reflns_number_total 2673 _reflns_number_gt 1904 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0300P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2673 _refine_ls_number_parameters 191 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1544 _refine_ls_wR_factor_gt 0.1419 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.4419(2) 0.6823(2) 0.61649(18) 0.0459(4) Uani 1 1 d D . . C12A C 0.4150(3) 0.8066(2) 0.6663(2) 0.0425(4) Uani 0.882(4) 1 d PD A 1 N12 N 0.3289(3) 0.8973(2) 0.5732(2) 0.0540(5) Uani 0.882(4) 1 d PD A 1 H12A H 0.279(4) 0.869(4) 0.489(4) 0.065 Uiso 0.882(4) 1 d P A 1 H12B H 0.296(4) 0.974(4) 0.606(4) 0.065 Uiso 0.882(4) 1 d P A 1 C12B C 0.4150(3) 0.8066(2) 0.6663(2) 0.0425(4) Uani 0.118(4) 1 d P A 2 H12 H 0.3542 0.8713 0.6019 0.051 Uiso 0.118(4) 1 calc PR A 2 C13 C 0.4783(3) 0.8404(2) 0.8165(2) 0.0479(5) Uani 1 1 d D . . H13 H 0.4579 0.9275 0.8494 0.057 Uiso 1 1 calc R A 1 N14 N 0.5649(2) 0.7527(2) 0.91049(18) 0.0506(4) Uani 1 1 d D A . C15A C 0.5902(3) 0.6279(3) 0.8604(2) 0.0519(5) Uani 0.882(4) 1 d P A 1 H15 H 0.6500 0.5631 0.9253 0.062 Uiso 0.882(4) 1 calc PR A 1 C15B C 0.5902(3) 0.6279(3) 0.8604(2) 0.0519(5) Uani 0.118(4) 1 d PD A 2 N15 N 0.679(2) 0.5396(16) 0.9430(14) 0.0540(5) Uani 0.118(4) 1 d PD A 2 H15A H 0.7251 0.5593 1.0335 0.065 Uiso 0.118(4) 1 calc PR A 2 H15B H 0.6942 0.4597 0.9088 0.065 Uiso 0.118(4) 1 calc PR A 2 C16 C 0.5290(3) 0.5936(2) 0.7140(2) 0.0504(5) Uani 1 1 d D A . H16 H 0.5490 0.5060 0.6823 0.060 Uiso 1 1 calc R B 1 C21 C 0.2380(3) 0.6843(3) 0.2386(2) 0.0492(5) Uani 1 1 d . . . O21 O 0.3168(3) 0.5932(2) 0.33286(18) 0.0706(5) Uani 1 1 d . . . H21 H 0.355(4) 0.632(4) 0.428(4) 0.085 Uiso 1 1 d . . . O22 O 0.2163(3) 0.7999(2) 0.2738(2) 0.0856(7) Uani 1 1 d . . . C22 C 0.1779(4) 0.6299(3) 0.0865(2) 0.0580(6) Uani 1 1 d . . . H22A H 0.0983 0.5545 0.0911 0.070 Uiso 1 1 calc R . . H22B H 0.2788 0.5937 0.0523 0.070 Uiso 1 1 calc R . . C23 C 0.0875(3) 0.7303(3) -0.0254(2) 0.0495(5) Uani 1 1 d . . . H23A H 0.1624 0.8095 -0.0250 0.059 Uiso 1 1 calc R . . H23B H -0.0200 0.7603 0.0030 0.059 Uiso 1 1 calc R . . C24 C 0.0437(3) 0.6725(2) -0.1803(2) 0.0470(5) Uani 1 1 d . . . H24A H -0.0312 0.5933 -0.1804 0.056 Uiso 1 1 calc R . . H24B H 0.1513 0.6420 -0.2082 0.056 Uiso 1 1 calc R . . C25 C -0.0473(3) 0.7728(3) -0.2951(2) 0.0490(5) Uani 1 1 d . . . H25A H 0.0279 0.8516 -0.2962 0.059 Uiso 1 1 calc R . . H25B H -0.1547 0.8038 -0.2673 0.059 Uiso 1 1 calc R . . C26 C -0.0913(3) 0.7120(3) -0.4492(2) 0.0501(5) Uani 1 1 d . . . H26A H 0.0161 0.6807 -0.4769 0.060 Uiso 1 1 calc R . . H26B H -0.1668 0.6333 -0.4481 0.060 Uiso 1 1 calc R . . C27 C -0.1817(3) 0.8123(3) -0.5640(2) 0.0553(5) Uani 1 1 d . . . H27A H -0.2819 0.8506 -0.5304 0.066 Uiso 1 1 calc R . . H27B H -0.1013 0.8864 -0.5713 0.066 Uiso 1 1 calc R . . C28 C -0.2435(3) 0.7529(3) -0.7151(2) 0.0483(5) Uani 1 1 d . . . O28 O -0.3031(3) 0.8456(2) -0.81503(18) 0.0687(5) Uani 1 1 d . . . H28 H -0.352(4) 0.801(4) -0.907(4) 0.082 Uiso 1 1 d . . . O29 O -0.2404(3) 0.6339(2) -0.7452(2) 0.0768(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0546(9) 0.0492(9) 0.0309(7) -0.0033(7) 0.0017(6) -0.0028(9) C12A 0.0488(10) 0.0463(10) 0.0299(7) 0.0002(7) 0.0021(7) -0.0045(9) N12 0.0778(13) 0.0446(9) 0.0316(8) -0.0006(8) -0.0081(8) 0.0064(9) C12B 0.0488(10) 0.0463(10) 0.0299(7) 0.0002(7) 0.0021(7) -0.0045(9) C13 0.0588(11) 0.0507(12) 0.0315(8) -0.0044(8) 0.0024(7) -0.0049(10) N14 0.0597(10) 0.0587(10) 0.0296(7) 0.0009(8) -0.0001(6) -0.0062(10) C15A 0.0608(12) 0.0558(13) 0.0356(9) 0.0077(9) 0.0014(8) -0.0009(11) C15B 0.0608(12) 0.0558(13) 0.0356(9) 0.0077(9) 0.0014(8) -0.0009(11) N15 0.0778(13) 0.0446(9) 0.0316(8) -0.0006(8) -0.0081(8) 0.0064(9) C16 0.0616(12) 0.0474(11) 0.0406(9) 0.0005(9) 0.0064(8) 0.0018(10) C21 0.0629(11) 0.0499(11) 0.0293(8) 0.0000(8) -0.0034(7) -0.0006(11) O21 0.1087(13) 0.0576(11) 0.0334(7) -0.0044(7) -0.0145(8) 0.0162(11) O22 0.1425(19) 0.0582(12) 0.0389(9) -0.0078(8) -0.0231(10) 0.0166(12) C22 0.0829(14) 0.0546(12) 0.0287(8) -0.0035(9) -0.0078(8) 0.0100(12) C23 0.0600(11) 0.0567(12) 0.0272(7) -0.0016(8) -0.0019(7) 0.0013(10) C24 0.0547(10) 0.0549(12) 0.0278(7) -0.0010(8) -0.0005(7) 0.0012(10) C25 0.0574(11) 0.0590(13) 0.0270(7) -0.0032(8) 0.0001(7) -0.0023(10) C26 0.0635(11) 0.0553(12) 0.0273(8) 0.0010(8) -0.0012(7) 0.0013(10) C27 0.0767(13) 0.0559(13) 0.0276(8) -0.0049(9) -0.0033(8) 0.0007(12) C28 0.0609(12) 0.0510(12) 0.0293(8) 0.0014(8) 0.0001(7) 0.0000(10) O28 0.1069(14) 0.0572(10) 0.0316(7) -0.0011(7) -0.0106(8) 0.0142(10) O29 0.1337(17) 0.0494(10) 0.0364(8) 0.0010(8) -0.0094(9) -0.0112(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C16 1.333(3) . ? N11 C12A 1.333(3) . ? C12A N12 1.320(3) . ? C12A C13 1.411(2) . ? N12 H12A 0.84(4) . ? N12 H12B 0.86(4) . ? C13 N14 1.307(3) . ? C13 H13 0.9300 . ? N14 C15A 1.336(3) . ? C15A C16 1.378(3) . ? C15A H15 0.9300 . ? N15 H15A 0.8600 . ? N15 H15B 0.8600 . ? C16 H16 0.9300 . ? C21 O22 1.200(3) . ? C21 O21 1.309(3) . ? C21 C22 1.484(3) . ? O21 H21 0.95(3) . ? C22 C23 1.494(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.509(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.512(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.514(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.510(3) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.496(3) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 O29 1.201(3) . ? C28 O28 1.310(3) . ? O28 H28 0.96(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12A 117.24(17) . . ? N12 C12A N11 119.05(18) . . ? N12 C12A C13 120.7(2) . . ? N11 C12A C13 120.24(19) . . ? C12A N12 H12A 117(2) . . ? C12A N12 H12B 120(2) . . ? H12A N12 H12B 120(3) . . ? N14 C13 C12A 121.8(2) . . ? N14 C13 H13 119.1 . . ? C12A C13 H13 119.1 . . ? C13 N14 C15A 117.72(17) . . ? N14 C15A C16 121.0(2) . . ? N14 C15A H15 119.5 . . ? C16 C15A H15 119.5 . . ? H15A N15 H15B 120.0 . . ? N11 C16 C15A 122.0(2) . . ? N11 C16 H16 119.0 . . ? C15A C16 H16 119.0 . . ? O22 C21 O21 122.5(2) . . ? O22 C21 C22 124.0(2) . . ? O21 C21 C22 113.5(2) . . ? C21 O21 H21 111(2) . . ? C21 C22 C23 115.5(2) . . ? C21 C22 H22A 108.4 . . ? C23 C22 H22A 108.4 . . ? C21 C22 H22B 108.4 . . ? C23 C22 H22B 108.4 . . ? H22A C22 H22B 107.5 . . ? C22 C23 C24 113.0(2) . . ? C22 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? C22 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? C23 C24 C25 113.72(18) . . ? C23 C24 H24A 108.8 . . ? C25 C24 H24A 108.8 . . ? C23 C24 H24B 108.8 . . ? C25 C24 H24B 108.8 . . ? H24A C24 H24B 107.7 . . ? C24 C25 C26 112.68(19) . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? C27 C26 C25 112.7(2) . . ? C27 C26 H26A 109.0 . . ? C25 C26 H26A 109.0 . . ? C27 C26 H26B 109.0 . . ? C25 C26 H26B 109.0 . . ? H26A C26 H26B 107.8 . . ? C28 C27 C26 114.6(2) . . ? C28 C27 H27A 108.6 . . ? C26 C27 H27A 108.6 . . ? C28 C27 H27B 108.6 . . ? C26 C27 H27B 108.6 . . ? H27A C27 H27B 107.6 . . ? O29 C28 O28 122.2(2) . . ? O29 C28 C27 125.1(2) . . ? O28 C28 C27 112.7(2) . . ? C28 O28 H28 109(2) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12A N12 -179.9(2) . . . . ? C16 N11 C12A C13 0.4(3) . . . . ? N12 C12A C13 N14 -179.5(2) . . . . ? N11 C12A C13 N14 0.3(3) . . . . ? C12A C13 N14 C15A -0.9(3) . . . . ? C13 N14 C15A C16 0.9(3) . . . . ? C12A N11 C16 C15A -0.4(3) . . . . ? N14 C15A C16 N11 -0.3(3) . . . . ? O22 C21 C22 C23 0.8(4) . . . . ? O21 C21 C22 C23 -179.8(2) . . . . ? C21 C22 C23 C24 174.9(2) . . . . ? C22 C23 C24 C25 -179.82(19) . . . . ? C23 C24 C25 C26 -179.5(2) . . . . ? C24 C25 C26 C27 -179.84(18) . . . . ? C25 C26 C27 C28 -174.25(19) . . . . ? C26 C27 C28 O29 7.1(4) . . . . ? C26 C27 C28 O28 -172.7(2) . . . . ? 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_site_symmetry_A N12 H12A O22 0.84(4) 2.06(4) 2.883(3) 167(3) . N12 H12B O29 0.86(4) 2.13(4) 2.966(3) 164(3) 2 N15 H15B O22 0.86 2.50 3.289(16) 153.3 2_646 N15 H15A O29 0.86 2.13 2.962(14) 162.2 1_657 O21 H21 N11 0.95(3) 1.80(3) 2.741(2) 172(3) . O28 H28 N14 0.96(4) 1.74(4) 2.689(2) 168(3) 1_453 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 33.15 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.253 _refine_diff_density_min -0.140 _refine_diff_density_rms 0.037 #END data_B1.A29 _database_code_depnum_ccdc_archive 'CCDC 876783' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; D4 2-aminopyrazine, HOOC-(CH2)8-COOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H5 N3) (C10 H18 O4) ; _chemical_formula_sum 'C14 H23 N3 O4' _chemical_formula_weight 297.35 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.7935(6) _cell_length_b 7.5090(8) _cell_length_c 8.7271(8) _cell_angle_alpha 92.984(4) _cell_angle_beta 91.952(5) _cell_angle_gamma 98.570(5) _cell_volume 374.57(7) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4985 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 33.16 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 160 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9562 _diffrn_reflns_av_R_equivalents 0.0203 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 33.13 _reflns_number_total 2756 _reflns_number_gt 2325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2756 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.81819(14) 0.92661(11) 0.89764(9) 0.02232(17) Uani 1 1 d . . . C12A C 1.02394(17) 1.00168(12) 0.84687(10) 0.02196(18) Uani 0.50 1 d P A 1 N12 N 1.0443(3) 1.0102(2) 0.69908(18) 0.0229(3) Uani 0.50 1 d P A 1 H12A H 0.928(5) 0.961(4) 0.643(3) 0.028 Uiso 0.50 1 d P B 1 H12B H 1.168(5) 1.058(4) 0.670(3) 0.028 Uiso 0.50 1 d P C 1 C12B C 1.02394(17) 1.00168(12) 0.84687(10) 0.02196(18) Uani 0.50 1 d P A 2 H12 H 1.0464 1.0052 0.7397 0.026 Uiso 0.50 1 calc PR A 2 C13 C 1.20554(16) 1.07486(13) 0.95170(11) 0.02316(19) Uani 1 1 d . . . H13 H 1.3504 1.1273 0.9139 0.028 Uiso 1 1 calc R A 1 C21 C 0.48581(17) 0.76210(13) 0.56748(10) 0.02297(19) Uani 1 1 d . . . O21 O 0.45417(13) 0.76324(11) 0.71629(8) 0.02959(18) Uani 1 1 d . . . H21 H 0.584(3) 0.829(2) 0.7629(18) 0.036 Uiso 1 1 d . . . O22 O 0.66536(15) 0.83119(13) 0.51329(9) 0.0397(2) Uani 1 1 d . . . C22 C 0.27960(16) 0.66334(13) 0.47434(10) 0.02245(18) Uani 1 1 d . . . H22A H 0.1410 0.7212 0.4977 0.027 Uiso 1 1 calc R . . H22B H 0.2486 0.5379 0.5068 0.027 Uiso 1 1 calc R . . C23 C 0.30785(16) 0.65785(12) 0.30205(10) 0.02160(18) Uani 1 1 d . . . H23A H 0.4467 0.6010 0.2774 0.026 Uiso 1 1 calc R . . H23B H 0.3342 0.7826 0.2678 0.026 Uiso 1 1 calc R . . C24 C 0.09362(16) 0.55270(12) 0.21589(9) 0.02143(18) Uani 1 1 d . . . H24A H 0.0702 0.4275 0.2492 0.026 Uiso 1 1 calc R . . H24B H -0.0453 0.6078 0.2439 0.026 Uiso 1 1 calc R . . C25 C 0.11087(16) 0.54759(12) 0.04248(10) 0.02135(18) Uani 1 1 d . . . H25A H 0.2432 0.4850 0.0137 0.026 Uiso 1 1 calc R . . H25B H 0.1445 0.6727 0.0096 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0229(4) 0.0239(4) 0.0192(3) -0.0004(3) -0.0037(3) 0.0018(3) C12A 0.0240(4) 0.0241(4) 0.0173(4) 0.0006(3) -0.0023(3) 0.0031(3) N12 0.0192(7) 0.0325(8) 0.0151(6) 0.0010(5) 0.0005(5) -0.0021(6) C12B 0.0240(4) 0.0241(4) 0.0173(4) 0.0006(3) -0.0023(3) 0.0031(3) C13 0.0213(4) 0.0258(4) 0.0215(4) 0.0012(3) -0.0016(3) 0.0013(3) C21 0.0236(4) 0.0248(4) 0.0191(4) -0.0011(3) -0.0042(3) 0.0009(3) O21 0.0249(3) 0.0427(4) 0.0176(3) -0.0039(3) -0.0045(2) -0.0034(3) O22 0.0318(4) 0.0557(5) 0.0243(4) 0.0001(3) -0.0021(3) -0.0161(4) C22 0.0212(4) 0.0275(4) 0.0163(4) -0.0014(3) -0.0031(3) -0.0022(3) C23 0.0215(4) 0.0255(4) 0.0162(4) 0.0003(3) -0.0025(3) -0.0007(3) C24 0.0227(4) 0.0246(4) 0.0152(3) 0.0001(3) -0.0025(3) -0.0012(3) C25 0.0231(4) 0.0239(4) 0.0155(4) -0.0002(3) -0.0022(3) -0.0005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C13 1.3270(12) 2_777 ? N11 C12A 1.3404(13) . ? C12A N12 1.3032(17) . ? C12A C13 1.3985(13) . ? N12 H12A 0.85(3) . ? N12 H12B 0.81(3) . ? C13 N11 1.3270(12) 2_777 ? C13 H13 0.9500 . ? C21 O22 1.2137(13) . ? C21 O21 1.3175(11) . ? C21 C22 1.4984(12) . ? O21 H21 0.905(17) . ? C22 C23 1.5172(12) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.5204(12) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.5190(12) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C25 1.5222(17) 2_565 ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 N11 C12A 117.94(8) 2_777 . ? N12 C12A N11 118.02(11) . . ? N12 C12A C13 121.93(11) . . ? N11 C12A C13 119.99(8) . . ? C12A N12 H12A 116.5(19) . . ? C12A N12 H12B 117(2) . . ? H12A N12 H12B 126(3) . . ? N11 C13 C12A 122.07(9) 2_777 . ? N11 C13 H13 119.0 2_777 . ? C12A C13 H13 119.0 . . ? O22 C21 O21 123.02(9) . . ? O22 C21 C22 124.21(9) . . ? O21 C21 C22 112.75(8) . . ? C21 O21 H21 106.7(10) . . ? C21 C22 C23 114.74(8) . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22B 108.6 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C23 C24 111.59(7) . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C25 C24 C23 113.57(7) . . ? C25 C24 H24A 108.9 . . ? C23 C24 H24A 108.9 . . ? C25 C24 H24B 108.9 . . ? C23 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? C24 C25 C25 112.99(9) . 2_565 ? C24 C25 H25A 109.0 . . ? C25 C25 H25A 109.0 2_565 . ? C24 C25 H25B 109.0 . . ? C25 C25 H25B 109.0 2_565 . ? H25A C25 H25B 107.8 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 N11 C12A N12 -177.12(11) 2_777 . . . ? C13 N11 C12A C13 0.17(15) 2_777 . . . ? N12 C12A C13 N11 177.00(12) . . . 2_777 ? N11 C12A C13 N11 -0.18(16) . . . 2_777 ? O22 C21 C22 C23 -1.18(15) . . . . ? O21 C21 C22 C23 -179.85(8) . . . . ? C21 C22 C23 C24 178.98(8) . . . . ? C22 C23 C24 C25 178.46(8) . . . . ? C23 C24 C25 C25 -176.27(9) . . . 2_565 ? 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_site_symmetry_A O21 H21 N11 0.905(17) 1.809(17) 2.6939(11) 165.2(14) . N12 H12A O22 0.85(3) 1.97(3) 2.8120(18) 177(3) . N12 H12B O22 0.81(3) 2.05(3) 2.7437(18) 144(3) 2_776 _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 33.13 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.495 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.047 #END data_B3.A7 _database_code_depnum_ccdc_archive 'CCDC 876784' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; P13 2,6-Br2-3-NH2-pyrazine, 2,5-(HO)2-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H3 N3 Br2) (C7 H6 O4) ; _chemical_formula_sum 'C11 H9 Br2 N3 O4' _chemical_formula_weight 407.03 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.8754(7) _cell_length_b 7.1197(7) _cell_length_c 13.8665(14) _cell_angle_alpha 87.951(3) _cell_angle_beta 86.435(3) _cell_angle_gamma 72.915(4) _cell_volume 647.46(11) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3146 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 31.48 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.088 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 6.277 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1880 _exptl_absorpt_correction_T_max 0.6336 _exptl_absorpt_process_details TWINABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6835 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 31.71 _reflns_number_total 6835 _reflns_number_gt 5403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0250P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6835 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.20470(4) 1.36243(4) 0.075465(17) 0.02033(9) Uani 1 1 d . . . Br2 Br 0.30359(4) 1.37412(4) 0.464582(18) 0.02262(9) Uani 1 1 d . . . N11 N 0.2689(3) 1.3275(3) 0.26946(15) 0.0159(4) Uani 1 1 d . . . C12 C 0.2961(4) 1.2245(4) 0.19127(17) 0.0146(5) Uani 1 1 d . . . C13 C 0.3897(4) 1.0187(4) 0.18829(17) 0.0153(5) Uani 1 1 d . . . N13 N 0.4175(4) 0.9146(3) 0.10779(16) 0.0188(5) Uani 1 1 d . . . H13A H 0.4798 0.7876 0.1095 0.023 Uiso 1 1 calc R . . H13B H 0.3736 0.9731 0.0530 0.023 Uiso 1 1 calc R . . N14 N 0.4582(3) 0.9261(3) 0.27104(15) 0.0164(4) Uani 1 1 d . . . C15 C 0.4330(4) 1.0300(4) 0.35143(17) 0.0163(5) Uani 1 1 d . . . H15 H 0.4820 0.9659 0.4102 0.020 Uiso 1 1 calc R . . C16 C 0.3371(4) 1.2289(4) 0.35028(18) 0.0158(5) Uani 1 1 d . . . C21 C 0.7997(4) 0.2256(4) 0.23489(18) 0.0152(5) Uani 1 1 d . . . C27 C 0.6948(4) 0.4357(4) 0.22160(17) 0.0160(5) Uani 1 1 d . . . O27 O 0.6657(3) 0.5433(3) 0.29796(13) 0.0199(4) Uani 1 1 d . . . H27 H 0.607(5) 0.655(6) 0.286(2) 0.024 Uiso 1 1 d . . . O28 O 0.6349(3) 0.5061(3) 0.14225(13) 0.0225(4) Uani 1 1 d . . . C22 C 0.8312(4) 0.1003(4) 0.15603(19) 0.0171(5) Uani 1 1 d . . . O22 O 0.7664(3) 0.1637(3) 0.06683(14) 0.0225(4) Uani 1 1 d . . . H22 H 0.708(5) 0.276(6) 0.071(3) 0.027 Uiso 1 1 d . . . C23 C 0.9317(4) -0.0993(4) 0.1680(2) 0.0228(6) Uani 1 1 d . . . H23 H 0.9525 -0.1848 0.1148 0.027 Uiso 1 1 calc R A . C24 C 1.0008(4) -0.1725(5) 0.2567(2) 0.0248(6) Uani 1 1 d . A . H24 H 1.0689 -0.3086 0.2646 0.030 Uiso 1 1 calc R . . C25 C 0.9713(4) -0.0479(4) 0.3350(2) 0.0223(6) Uani 1 1 d . . . O25 O 1.0464(3) -0.1240(3) 0.42215(15) 0.0291(5) Uani 1 1 d . A 1 H25A H 0.9880 -0.0466 0.4664 0.035 Uiso 0.50 1 d PR A 1 H25B H 1.0216 -0.2316 0.4335 0.035 Uiso 0.50 1 d PR A 1 C26 C 0.8720(4) 0.1482(4) 0.32485(19) 0.0186(5) Uani 1 1 d . A 1 H26 H 0.8519 0.2321 0.3786 0.022 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02339(15) 0.01938(16) 0.01533(13) 0.00354(10) -0.00622(10) -0.00113(11) Br2 0.03237(17) 0.01759(16) 0.01549(13) -0.00331(10) -0.00486(11) -0.00249(12) N11 0.0146(10) 0.0159(11) 0.0162(10) -0.0010(9) -0.0025(8) -0.0025(9) C12 0.0143(11) 0.0145(12) 0.0140(11) 0.0032(9) -0.0024(9) -0.0025(10) C13 0.0164(12) 0.0164(13) 0.0134(11) -0.0003(10) -0.0027(9) -0.0046(10) N13 0.0258(12) 0.0148(11) 0.0123(9) 0.0001(9) -0.0044(8) 0.0001(9) N14 0.0185(10) 0.0150(11) 0.0143(10) 0.0002(8) -0.0027(8) -0.0023(9) C15 0.0189(12) 0.0170(13) 0.0131(11) 0.0016(10) -0.0043(9) -0.0053(10) C16 0.0162(11) 0.0169(13) 0.0146(11) -0.0019(9) -0.0023(9) -0.0049(10) C21 0.0146(11) 0.0163(13) 0.0149(11) 0.0003(10) -0.0009(9) -0.0048(10) C27 0.0178(12) 0.0162(13) 0.0146(11) -0.0003(10) -0.0029(9) -0.0054(10) O27 0.0312(11) 0.0111(9) 0.0152(8) -0.0019(7) -0.0039(7) -0.0022(8) O28 0.0301(11) 0.0181(10) 0.0175(9) 0.0012(8) -0.0073(8) -0.0034(9) C22 0.0159(12) 0.0173(13) 0.0183(12) -0.0006(10) -0.0034(9) -0.0049(10) O22 0.0283(11) 0.0193(10) 0.0182(9) -0.0025(8) -0.0082(8) -0.0025(9) C23 0.0213(13) 0.0202(15) 0.0273(14) -0.0040(12) -0.0015(11) -0.0063(11) C24 0.0185(13) 0.0158(14) 0.0374(16) 0.0048(12) -0.0011(11) -0.0017(11) C25 0.0180(12) 0.0227(15) 0.0248(13) 0.0078(11) -0.0034(10) -0.0045(11) O25 0.0363(12) 0.0221(11) 0.0244(10) 0.0090(9) -0.0065(9) -0.0018(9) C26 0.0201(12) 0.0188(14) 0.0172(12) 0.0027(10) -0.0025(10) -0.0063(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C12 1.894(3) . ? Br2 C16 1.888(2) . ? N11 C12 1.303(3) . ? N11 C16 1.336(3) . ? C12 C13 1.418(4) . ? C13 N13 1.334(3) . ? C13 N14 1.343(3) . ? N13 H13A 0.8800 . ? N13 H13B 0.8800 . ? N14 C15 1.334(3) . ? C15 C16 1.375(4) . ? C15 H15 0.9500 . ? C21 C22 1.402(4) . ? C21 C26 1.405(4) . ? C21 C27 1.468(4) . ? C27 O28 1.236(3) . ? C27 O27 1.300(3) . ? O27 H27 0.80(4) . ? C22 O22 1.357(3) . ? C22 C23 1.394(4) . ? O22 H22 0.78(4) . ? C23 C24 1.375(4) . ? C23 H23 0.9500 . ? C24 C25 1.395(4) . ? C24 H24 0.9500 . ? C25 C26 1.369(4) . ? C25 O25 1.373(4) . ? O25 H25A 0.8400 . ? O25 H25B 0.8400 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 116.4(2) . . ? N11 C12 C13 124.0(2) . . ? N11 C12 Br1 117.0(2) . . ? C13 C12 Br1 118.96(18) . . ? N13 C13 N14 118.9(2) . . ? N13 C13 C12 123.6(2) . . ? N14 C13 C12 117.5(2) . . ? C13 N13 H13A 120.0 . . ? C13 N13 H13B 120.0 . . ? H13A N13 H13B 120.0 . . ? C15 N14 C13 119.0(2) . . ? N14 C15 C16 120.8(2) . . ? N14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? N11 C16 C15 122.2(2) . . ? N11 C16 Br2 117.5(2) . . ? C15 C16 Br2 120.29(19) . . ? C22 C21 C26 119.4(3) . . ? C22 C21 C27 119.4(2) . . ? C26 C21 C27 121.2(2) . . ? O28 C27 O27 121.8(3) . . ? O28 C27 C21 121.7(2) . . ? O27 C27 C21 116.5(2) . . ? C27 O27 H27 111(2) . . ? O22 C22 C23 117.3(2) . . ? O22 C22 C21 122.9(3) . . ? C23 C22 C21 119.7(2) . . ? C22 O22 H22 107(3) . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C26 C25 O25 120.5(3) . . ? C26 C25 C24 120.4(3) . . ? O25 C25 C24 119.1(3) . . ? C25 O25 H25A 109.5 . . ? C25 O25 H25B 109.5 . . ? H25A O25 H25B 108.1 . . ? C25 C26 C21 120.1(2) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 0.7(4) . . . . ? C16 N11 C12 Br1 -178.91(18) . . . . ? N11 C12 C13 N13 -179.7(2) . . . . ? Br1 C12 C13 N13 -0.1(3) . . . . ? N11 C12 C13 N14 -1.5(4) . . . . ? Br1 C12 C13 N14 178.09(18) . . . . ? N13 C13 N14 C15 179.1(2) . . . . ? C12 C13 N14 C15 0.9(4) . . . . ? C13 N14 C15 C16 0.5(4) . . . . ? C12 N11 C16 C15 0.7(4) . . . . ? C12 N11 C16 Br2 179.16(18) . . . . ? N14 C15 C16 N11 -1.4(4) . . . . ? N14 C15 C16 Br2 -179.8(2) . . . . ? C22 C21 C27 O28 -0.7(4) . . . . ? C26 C21 C27 O28 178.3(3) . . . . ? C22 C21 C27 O27 178.4(2) . . . . ? C26 C21 C27 O27 -2.7(4) . . . . ? C26 C21 C22 O22 -179.9(2) . . . . ? C27 C21 C22 O22 -0.9(4) . . . . ? C26 C21 C22 C23 0.7(4) . . . . ? C27 C21 C22 C23 179.7(2) . . . . ? O22 C22 C23 C24 -179.9(3) . . . . ? C21 C22 C23 C24 -0.5(4) . . . . ? C22 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C26 0.5(4) . . . . ? C23 C24 C25 O25 -178.4(3) . . . . ? O25 C25 C26 C21 178.6(2) . . . . ? C24 C25 C26 C21 -0.3(4) . . . . ? C22 C21 C26 C25 -0.3(4) . . . . ? C27 C21 C26 C25 -179.3(3) . . . . ? 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_site_symmetry_A O27 H27 N14 0.80(4) 1.91(4) 2.704(3) 174(4) . N13 H13A O28 0.88 2.02 2.891(3) 167.9 . N13 H13B O22 0.88 2.35 2.944(3) 125.4 2_665 O22 H22 O28 0.78(4) 1.87(4) 2.574(3) 149(4) . O25 H25A O25 0.84 1.96 2.762(4) 159.5 2_756 _diffrn_measured_fraction_theta_max 0.928 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.123 _refine_diff_density_min -1.147 _refine_diff_density_rms 0.179 #END data_B3.A13 _database_code_depnum_ccdc_archive 'CCDC 876785' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; AR-cc-2c-10 2,6-dibromo-3-aminopyrazine, F5-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H3 N3 Br2) (C7 H F5 O2) ; _chemical_formula_sum 'C11 H4 Br2 F5 N3 O2' _chemical_formula_weight 464.99 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.5511(6) _cell_length_b 5.8057(2) _cell_length_c 16.0859(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.0750(10) _cell_angle_gamma 90.00 _cell_volume 1355.17(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 31.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 6.054 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3129 _exptl_absorpt_correction_T_max 0.5827 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24119 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 31.28 _reflns_number_total 4278 _reflns_number_gt 3611 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4278 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0577 _refine_ls_wR_factor_gt 0.0542 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.881000(12) -0.16360(3) 0.419341(13) 0.02139(5) Uani 1 1 d . . . Br2 Br 0.613309(12) -0.35497(3) 0.553333(12) 0.02040(5) Uani 1 1 d . . . N11 N 0.63981(10) 0.1610(2) 0.39202(10) 0.0162(3) Uani 1 1 d . . . C12 C 0.71973(11) 0.1110(3) 0.38324(11) 0.0157(3) Uani 1 1 d . . . N12 N 0.74966(11) 0.2445(3) 0.33215(11) 0.0203(3) Uani 1 1 d . . . H12A H 0.7185(16) 0.368(4) 0.3113(15) 0.024 Uiso 1 1 d . . . H12B H 0.8007(16) 0.228(4) 0.3283(15) 0.024 Uiso 1 1 d . . . C13 C 0.76779(11) -0.0863(3) 0.42876(11) 0.0155(3) Uani 1 1 d . . . N14 N 0.73826(9) -0.2190(2) 0.47776(9) 0.0161(3) Uani 1 1 d . . . C15 C 0.65797(11) -0.1626(3) 0.48435(11) 0.0159(3) Uani 1 1 d . . . C16 C 0.60901(11) 0.0257(3) 0.44261(11) 0.0166(3) Uani 1 1 d . . . H16 H 0.5523 0.0613 0.4495 0.020 Uiso 1 1 calc R . . C21 C 0.47201(11) 0.8073(3) 0.23032(11) 0.0146(3) Uani 1 1 d . . . C27 C 0.54521(11) 0.6335(3) 0.27287(11) 0.0153(3) Uani 1 1 d . . . O21 O 0.51650(9) 0.4631(2) 0.30854(9) 0.0228(3) Uani 1 1 d . . . H21 H 0.5560(17) 0.381(4) 0.3315(17) 0.027 Uiso 1 1 d . . . O22 O 0.62261(8) 0.65359(19) 0.27233(9) 0.0186(2) Uani 1 1 d . . . C22 C 0.46961(11) 0.9188(3) 0.15328(11) 0.0157(3) Uani 1 1 d . . . F22 F 0.53015(7) 0.86784(17) 0.11536(7) 0.0214(2) Uani 1 1 d . . . C23 C 0.40410(12) 1.0820(3) 0.11263(11) 0.0179(3) Uani 1 1 d . . . F23 F 0.40334(8) 1.18647(18) 0.03894(7) 0.0262(2) Uani 1 1 d . . . C24 C 0.33868(12) 1.1370(3) 0.14866(12) 0.0178(3) Uani 1 1 d . . . F24 F 0.27604(8) 1.29613(18) 0.10964(8) 0.0254(2) Uani 1 1 d . . . C25 C 0.33879(11) 1.0291(3) 0.22422(11) 0.0167(3) Uani 1 1 d . . . F25 F 0.27543(7) 1.08201(18) 0.25863(7) 0.0221(2) Uani 1 1 d . . . C26 C 0.40540(12) 0.8677(3) 0.26460(11) 0.0159(3) Uani 1 1 d . . . F26 F 0.40581(7) 0.77728(18) 0.34088(7) 0.0204(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01617(9) 0.02153(9) 0.02910(10) 0.00418(7) 0.01132(7) 0.00608(6) Br2 0.01876(9) 0.02048(8) 0.02280(10) 0.00586(6) 0.00849(7) -0.00177(6) N11 0.0141(7) 0.0162(6) 0.0186(7) 0.0021(5) 0.0062(6) 0.0015(5) C12 0.0140(7) 0.0153(7) 0.0175(8) -0.0011(6) 0.0052(6) -0.0003(6) N12 0.0163(7) 0.0210(7) 0.0266(8) 0.0075(6) 0.0116(6) 0.0043(6) C13 0.0117(7) 0.0165(7) 0.0177(8) -0.0019(6) 0.0045(6) 0.0005(6) N14 0.0146(7) 0.0154(6) 0.0164(7) 0.0000(5) 0.0032(5) 0.0005(5) C15 0.0154(8) 0.0159(7) 0.0163(8) 0.0003(6) 0.0055(6) -0.0033(6) C16 0.0134(7) 0.0177(7) 0.0186(8) 0.0011(6) 0.0059(6) 0.0003(6) C21 0.0107(7) 0.0139(7) 0.0171(8) 0.0013(6) 0.0025(6) -0.0013(5) C27 0.0143(8) 0.0158(7) 0.0145(7) 0.0006(6) 0.0035(6) -0.0002(6) O21 0.0143(6) 0.0204(6) 0.0333(7) 0.0137(5) 0.0081(5) 0.0042(5) O22 0.0145(6) 0.0196(6) 0.0219(6) 0.0034(5) 0.0068(5) 0.0018(4) C22 0.0134(7) 0.0169(7) 0.0176(8) 0.0005(6) 0.0066(6) -0.0009(6) F22 0.0195(5) 0.0266(5) 0.0217(5) 0.0052(4) 0.0118(4) 0.0035(4) C23 0.0179(8) 0.0186(7) 0.0165(8) 0.0055(6) 0.0056(6) -0.0002(6) F23 0.0288(6) 0.0300(5) 0.0221(5) 0.0136(4) 0.0121(5) 0.0068(5) C24 0.0150(8) 0.0163(7) 0.0204(8) 0.0021(6) 0.0043(6) 0.0027(6) F24 0.0229(5) 0.0242(5) 0.0277(6) 0.0100(4) 0.0074(5) 0.0109(4) C25 0.0133(7) 0.0170(7) 0.0199(8) -0.0016(6) 0.0062(6) -0.0006(6) F25 0.0184(5) 0.0252(5) 0.0252(5) 0.0017(4) 0.0109(4) 0.0059(4) C26 0.0158(8) 0.0163(7) 0.0153(7) 0.0023(6) 0.0053(6) -0.0014(6) F26 0.0192(5) 0.0248(5) 0.0194(5) 0.0085(4) 0.0098(4) 0.0032(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C13 1.8749(16) . ? Br2 C15 1.8749(16) . ? N11 C12 1.332(2) . ? N11 C16 1.338(2) . ? C12 N12 1.330(2) . ? C12 C13 1.419(2) . ? N12 H12A 0.86(2) . ? N12 H12B 0.82(2) . ? C13 N14 1.298(2) . ? N14 C15 1.331(2) . ? C15 C16 1.363(2) . ? C16 H16 0.9500 . ? C21 C26 1.382(2) . ? C21 C22 1.387(2) . ? C21 C27 1.490(2) . ? C27 O22 1.212(2) . ? C27 O21 1.3007(19) . ? O21 H21 0.76(2) . ? C22 F22 1.3262(18) . ? C22 C23 1.373(2) . ? C23 F23 1.3277(19) . ? C23 C24 1.377(2) . ? C24 F24 1.3253(19) . ? C24 C25 1.367(2) . ? C25 F25 1.3281(18) . ? C25 C26 1.374(2) . ? C26 F26 1.3326(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 119.23(14) . . ? N12 C12 N11 119.06(15) . . ? N12 C12 C13 123.57(15) . . ? N11 C12 C13 117.36(15) . . ? C12 N12 H12A 116.8(15) . . ? C12 N12 H12B 122.6(16) . . ? H12A N12 H12B 119(2) . . ? N14 C13 C12 123.82(15) . . ? N14 C13 Br1 117.03(12) . . ? C12 C13 Br1 119.15(12) . . ? C13 N14 C15 116.67(14) . . ? N14 C15 C16 122.13(15) . . ? N14 C15 Br2 117.27(12) . . ? C16 C15 Br2 120.60(13) . . ? N11 C16 C15 120.79(15) . . ? N11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C26 C21 C22 117.04(15) . . ? C26 C21 C27 123.15(15) . . ? C22 C21 C27 119.81(15) . . ? O22 C27 O21 125.13(15) . . ? O22 C27 C21 121.86(14) . . ? O21 C27 C21 113.01(14) . . ? C27 O21 H21 110.2(18) . . ? F22 C22 C23 117.58(14) . . ? F22 C22 C21 120.75(14) . . ? C23 C22 C21 121.66(15) . . ? F23 C23 C22 120.49(15) . . ? F23 C23 C24 119.93(15) . . ? C22 C23 C24 119.58(15) . . ? F24 C24 C25 120.41(15) . . ? F24 C24 C23 119.39(15) . . ? C25 C24 C23 120.20(15) . . ? F25 C25 C24 120.05(15) . . ? F25 C25 C26 120.44(15) . . ? C24 C25 C26 119.50(15) . . ? F26 C26 C25 117.20(15) . . ? F26 C26 C21 120.73(15) . . ? C25 C26 C21 122.01(15) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 179.30(15) . . . . ? C16 N11 C12 C13 0.1(2) . . . . ? N12 C12 C13 N14 -179.03(16) . . . . ? N11 C12 C13 N14 0.1(3) . . . . ? N12 C12 C13 Br1 1.3(2) . . . . ? N11 C12 C13 Br1 -179.60(12) . . . . ? C12 C13 N14 C15 0.1(2) . . . . ? Br1 C13 N14 C15 179.79(12) . . . . ? C13 N14 C15 C16 -0.5(2) . . . . ? C13 N14 C15 Br2 179.04(12) . . . . ? C12 N11 C16 C15 -0.5(2) . . . . ? N14 C15 C16 N11 0.8(3) . . . . ? Br2 C15 C16 N11 -178.77(12) . . . . ? C26 C21 C27 O22 -144.38(17) . . . . ? C22 C21 C27 O22 34.7(2) . . . . ? C26 C21 C27 O21 36.2(2) . . . . ? C22 C21 C27 O21 -144.71(16) . . . . ? C26 C21 C22 F22 -178.86(14) . . . . ? C27 C21 C22 F22 2.0(2) . . . . ? C26 C21 C22 C23 0.0(2) . . . . ? C27 C21 C22 C23 -179.16(15) . . . . ? F22 C22 C23 F23 -1.2(2) . . . . ? C21 C22 C23 F23 179.95(15) . . . . ? F22 C22 C23 C24 178.69(15) . . . . ? C21 C22 C23 C24 -0.2(3) . . . . ? F23 C23 C24 F24 -0.7(2) . . . . ? C22 C23 C24 F24 179.42(15) . . . . ? F23 C23 C24 C25 179.62(16) . . . . ? C22 C23 C24 C25 -0.3(3) . . . . ? F24 C24 C25 F25 0.6(2) . . . . ? C23 C24 C25 F25 -179.77(15) . . . . ? F24 C24 C25 C26 -178.78(15) . . . . ? C23 C24 C25 C26 0.9(3) . . . . ? F25 C25 C26 F26 -3.2(2) . . . . ? C24 C25 C26 F26 176.18(15) . . . . ? F25 C25 C26 C21 179.54(15) . . . . ? C24 C25 C26 C21 -1.1(3) . . . . ? C22 C21 C26 F26 -176.52(15) . . . . ? C27 C21 C26 F26 2.6(2) . . . . ? C22 C21 C26 C25 0.7(2) . . . . ? C27 C21 C26 C25 179.78(15) . . . . ? 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_site_symmetry_A O21 H21 N11 0.76(2) 1.84(2) 2.5892(19) 172(3) . N12 H12A O22 0.86(2) 2.17(2) 3.0174(19) 169(2) . N12 H12B O22 0.82(2) 2.37(2) 3.074(2) 144(2) 2_645 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 31.28 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.507 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.083 #END data_B3.A14 _database_code_depnum_ccdc_archive 'CCDC 876786' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; P9 2-amino-3,5-dibromopyrazine, 3,5-(NO2)2-PhCOOH ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H3 N3 Br2) (C7 H4 N2 O6) ; _chemical_formula_sum 'C11 H7 Br2 N5 O6' _chemical_formula_weight 465.04 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3153(3) _cell_length_b 10.4607(4) _cell_length_c 10.8371(4) _cell_angle_alpha 65.094(2) _cell_angle_beta 83.688(2) _cell_angle_gamma 89.742(2) _cell_volume 746.80(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7036 _cell_measurement_theta_min 2.14 _cell_measurement_theta_max 31.40 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.068 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 5.470 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3417 _exptl_absorpt_correction_T_max 0.4942 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14478 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 31.46 _reflns_number_total 4782 _reflns_number_gt 4074 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4782 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.06641(2) 0.730471(19) 0.338514(19) 0.02422(6) Uani 1 1 d . . . Br2 Br 0.74020(2) 0.892824(16) 0.029636(17) 0.02195(6) Uani 1 1 d . . . N11 N 0.5205(2) 0.50585(14) 0.31295(14) 0.0192(3) Uani 1 1 d . . . C12 C 0.6377(2) 0.60501(16) 0.21628(16) 0.0174(3) Uani 1 1 d . . . N12 N 0.8003(2) 0.56771(16) 0.17417(17) 0.0231(3) Uani 1 1 d . . . H12A H 0.833(3) 0.494(2) 0.214(2) 0.028 Uiso 1 1 d . . . H12B H 0.875(3) 0.636(2) 0.114(2) 0.028 Uiso 1 1 d . . . C13 C 0.5781(2) 0.74590(16) 0.15994(16) 0.0176(3) Uani 1 1 d . . . N14 N 0.4159(2) 0.78131(15) 0.19429(14) 0.0189(3) Uani 1 1 d . . . C15 C 0.3016(2) 0.67921(17) 0.28894(17) 0.0188(3) Uani 1 1 d . . . C16 C 0.3539(2) 0.54165(18) 0.34953(17) 0.0202(3) Uani 1 1 d . . . H16 H 0.2710 0.4715 0.4179 0.024 Uiso 1 1 calc R . . C21 C 0.5075(2) 0.02246(16) 0.64904(16) 0.0155(3) Uani 1 1 d . . . C27 C 0.4611(2) 0.16937(16) 0.55691(16) 0.0168(3) Uani 1 1 d . . . O21 O 0.59773(17) 0.23832(12) 0.46242(12) 0.0194(2) Uani 1 1 d . . . H21 H 0.574(3) 0.310(2) 0.419(2) 0.023 Uiso 1 1 d . . . O22 O 0.31209(18) 0.21635(13) 0.56983(13) 0.0253(3) Uani 1 1 d . . . C22 C 0.3708(2) -0.06365(16) 0.74946(16) 0.0166(3) Uani 1 1 d . . . H22 H 0.2520 -0.0299 0.7603 0.020 Uiso 1 1 calc R . . C23 C 0.4130(2) -0.20011(16) 0.83325(15) 0.0166(3) Uani 1 1 d . . . N23 N 0.2721(2) -0.28975(15) 0.94282(15) 0.0203(3) Uani 1 1 d . . . O23 O 0.1189(2) -0.24299(16) 0.94946(15) 0.0359(4) Uani 1 1 d . . . O24 O 0.3156(2) -0.40545(13) 1.02373(14) 0.0282(3) Uani 1 1 d . . . C24 C 0.5822(2) -0.25580(16) 0.82008(16) 0.0172(3) Uani 1 1 d . . . H24 H 0.6068 -0.3506 0.8769 0.021 Uiso 1 1 calc R . . C25 C 0.7136(2) -0.16543(16) 0.71929(16) 0.0166(3) Uani 1 1 d . . . N25 N 0.8968(2) -0.21774(16) 0.70280(15) 0.0222(3) Uani 1 1 d . . . O25 O 0.9123(2) -0.34632(14) 0.75332(17) 0.0382(4) Uani 1 1 d . . . O26 O 1.02307(18) -0.13097(14) 0.64004(14) 0.0285(3) Uani 1 1 d . . . C26 C 0.6813(2) -0.02703(16) 0.63444(16) 0.0162(3) Uani 1 1 d . . . H26 H 0.7758 0.0326 0.5679 0.019 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.01609(9) 0.02426(9) 0.03325(10) -0.01330(7) -0.00226(7) 0.00624(6) Br2 0.02458(10) 0.01419(8) 0.02119(9) -0.00269(6) 0.00114(6) 0.00049(6) N11 0.0196(7) 0.0121(6) 0.0209(6) -0.0027(5) -0.0005(5) 0.0028(5) C12 0.0184(8) 0.0145(7) 0.0182(7) -0.0057(6) -0.0035(6) 0.0036(6) N12 0.0191(8) 0.0158(6) 0.0288(8) -0.0050(6) 0.0014(6) 0.0046(5) C13 0.0197(8) 0.0122(6) 0.0179(7) -0.0033(5) -0.0026(6) 0.0023(5) N14 0.0195(7) 0.0149(6) 0.0215(6) -0.0063(5) -0.0050(5) 0.0054(5) C15 0.0162(8) 0.0180(7) 0.0220(7) -0.0083(6) -0.0026(6) 0.0044(6) C16 0.0179(8) 0.0171(7) 0.0217(7) -0.0050(6) 0.0000(6) 0.0018(6) C21 0.0166(8) 0.0121(6) 0.0156(6) -0.0041(5) -0.0008(5) 0.0023(5) C27 0.0182(8) 0.0137(7) 0.0163(7) -0.0045(5) -0.0014(6) 0.0026(5) O21 0.0185(6) 0.0112(5) 0.0211(6) -0.0005(4) 0.0014(4) 0.0031(4) O22 0.0188(6) 0.0188(6) 0.0275(6) -0.0008(5) 0.0029(5) 0.0074(5) C22 0.0148(7) 0.0155(7) 0.0179(7) -0.0060(6) 0.0005(5) 0.0029(5) C23 0.0169(8) 0.0133(6) 0.0150(6) -0.0020(5) 0.0009(5) -0.0004(5) N23 0.0200(7) 0.0169(6) 0.0183(6) -0.0032(5) 0.0021(5) -0.0005(5) O23 0.0202(7) 0.0328(8) 0.0336(7) 0.0031(6) 0.0103(6) 0.0060(6) O24 0.0298(7) 0.0144(6) 0.0273(6) 0.0020(5) 0.0047(5) 0.0008(5) C24 0.0179(8) 0.0113(6) 0.0177(7) -0.0021(5) -0.0001(6) 0.0013(5) C25 0.0149(7) 0.0143(7) 0.0181(7) -0.0048(6) -0.0009(5) 0.0029(5) N25 0.0168(7) 0.0172(6) 0.0244(7) -0.0020(5) 0.0017(6) 0.0046(5) O25 0.0276(8) 0.0165(6) 0.0527(9) -0.0002(6) 0.0068(7) 0.0102(5) O26 0.0157(6) 0.0233(6) 0.0320(7) 0.0005(5) 0.0040(5) 0.0013(5) C26 0.0155(7) 0.0125(6) 0.0172(7) -0.0036(5) 0.0003(5) 0.0007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C15 1.8884(17) . ? Br2 C13 1.8928(16) . ? N11 C16 1.341(2) . ? N11 C12 1.343(2) . ? C12 N12 1.342(2) . ? C12 C13 1.425(2) . ? N12 H12A 0.76(2) . ? N12 H12B 0.88(2) . ? C13 N14 1.303(2) . ? N14 C15 1.338(2) . ? C15 C16 1.380(2) . ? C16 H16 0.9500 . ? C21 C26 1.389(2) . ? C21 C22 1.392(2) . ? C21 C27 1.500(2) . ? C27 O22 1.212(2) . ? C27 O21 1.314(2) . ? O21 H21 0.73(2) . ? C22 C23 1.387(2) . ? C22 H22 0.9500 . ? C23 C24 1.384(2) . ? C23 N23 1.468(2) . ? N23 O24 1.2244(18) . ? N23 O23 1.227(2) . ? C24 C25 1.385(2) . ? C24 H24 0.9500 . ? C25 C26 1.386(2) . ? C25 N25 1.467(2) . ? N25 O26 1.2201(19) . ? N25 O25 1.2303(19) . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 N11 C12 119.62(14) . . ? N12 C12 N11 119.57(14) . . ? N12 C12 C13 123.19(15) . . ? N11 C12 C13 117.20(15) . . ? C12 N12 H12A 119.4(18) . . ? C12 N12 H12B 116.8(15) . . ? H12A N12 H12B 122(2) . . ? N14 C13 C12 123.50(15) . . ? N14 C13 Br2 116.90(11) . . ? C12 C13 Br2 119.60(13) . . ? C13 N14 C15 117.60(14) . . ? N14 C15 C16 121.33(15) . . ? N14 C15 Br1 117.60(12) . . ? C16 C15 Br1 121.07(13) . . ? N11 C16 C15 120.72(16) . . ? N11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C26 C21 C22 120.72(14) . . ? C26 C21 C27 121.15(14) . . ? C22 C21 C27 118.14(14) . . ? O22 C27 O21 124.88(14) . . ? O22 C27 C21 122.43(15) . . ? O21 C27 C21 112.69(13) . . ? C27 O21 H21 111.3(18) . . ? C23 C22 C21 118.07(15) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? C24 C23 C22 123.41(15) . . ? C24 C23 N23 118.17(14) . . ? C22 C23 N23 118.42(14) . . ? O24 N23 O23 123.99(15) . . ? O24 N23 C23 117.97(15) . . ? O23 N23 C23 118.02(14) . . ? C23 C24 C25 116.15(14) . . ? C23 C24 H24 121.9 . . ? C25 C24 H24 121.9 . . ? C24 C25 C26 123.17(15) . . ? C24 C25 N25 118.54(13) . . ? C26 C25 N25 118.29(14) . . ? O26 N25 O25 124.59(15) . . ? O26 N25 C25 117.84(14) . . ? O25 N25 C25 117.56(15) . . ? C25 C26 C21 118.43(15) . . ? C25 C26 H26 120.8 . . ? C21 C26 H26 120.8 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 -176.24(16) . . . . ? C16 N11 C12 C13 1.7(2) . . . . ? N12 C12 C13 N14 175.59(16) . . . . ? N11 C12 C13 N14 -2.2(3) . . . . ? N12 C12 C13 Br2 -5.2(2) . . . . ? N11 C12 C13 Br2 176.97(12) . . . . ? C12 C13 N14 C15 0.9(2) . . . . ? Br2 C13 N14 C15 -178.28(12) . . . . ? C13 N14 C15 C16 0.9(2) . . . . ? C13 N14 C15 Br1 -179.90(12) . . . . ? C12 N11 C16 C15 0.0(3) . . . . ? N14 C15 C16 N11 -1.4(3) . . . . ? Br1 C15 C16 N11 179.43(13) . . . . ? C26 C21 C27 O22 -178.01(17) . . . . ? C22 C21 C27 O22 2.4(2) . . . . ? C26 C21 C27 O21 2.6(2) . . . . ? C22 C21 C27 O21 -177.04(15) . . . . ? C26 C21 C22 C23 -0.5(2) . . . . ? C27 C21 C22 C23 179.08(15) . . . . ? C21 C22 C23 C24 -1.5(3) . . . . ? C21 C22 C23 N23 177.65(15) . . . . ? C24 C23 N23 O24 5.5(2) . . . . ? C22 C23 N23 O24 -173.70(16) . . . . ? C24 C23 N23 O23 -175.98(16) . . . . ? C22 C23 N23 O23 4.8(2) . . . . ? C22 C23 C24 C25 2.0(2) . . . . ? N23 C23 C24 C25 -177.22(14) . . . . ? C23 C24 C25 C26 -0.4(2) . . . . ? C23 C24 C25 N25 178.60(14) . . . . ? C24 C25 N25 O26 -161.98(16) . . . . ? C26 C25 N25 O26 17.1(2) . . . . ? C24 C25 N25 O25 18.0(2) . . . . ? C26 C25 N25 O25 -162.92(17) . . . . ? C24 C25 C26 C21 -1.5(3) . . . . ? N25 C25 C26 C21 179.48(14) . . . . ? C22 C21 C26 C25 2.0(2) . . . . ? C27 C21 C26 C25 -177.62(15) . . . . ? 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_site_symmetry_A O21 H21 N11 0.73(2) 1.94(2) 2.6728(17) 176(2) . N12 H12A O25 0.76(2) 2.38(2) 3.031(2) 145(2) 2_756 N12 H12B O23 0.88(2) 2.32(2) 3.165(2) 162(2) 1_664 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.020 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.099 #END data_B3.A18 _database_code_depnum_ccdc_archive 'CCDC 876787' #TrackingRef '- all.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ARcc-2c-7 2-amino-3,5-dibromopyrazine, 2,6-difluorobenzoic acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C4 H3 N3 Br2) (C7 H4 O2 F2) ; _chemical_formula_sum 'C11 H7 Br2 F2 N3 O2' _chemical_formula_weight 411.02 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 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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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' _cell_length_a 5.6663(5) _cell_length_b 13.2299(11) _cell_length_c 17.3426(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.911(4) _cell_angle_gamma 90.00 _cell_volume 1297.05(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9944 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 31.31 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 6.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3028 _exptl_absorpt_correction_T_max 0.4527 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31619 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 31.50 _reflns_number_total 4324 _reflns_number_gt 3128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4324 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 1.28639(4) 0.948696(15) 0.643763(13) 0.02276(7) Uani 1 1 d . . . Br2 Br 1.39519(4) 0.541654(15) 0.599085(13) 0.02338(7) Uani 1 1 d . . . N11 N 0.8668(3) 0.73924(12) 0.52445(9) 0.0171(4) Uani 1 1 d . . . C12 C 0.9444(4) 0.82726(15) 0.55554(12) 0.0167(4) Uani 1 1 d . . . N12 N 0.8141(3) 0.91031(14) 0.54212(12) 0.0229(4) Uani 1 1 d . . . H12A H 0.689(5) 0.8995(18) 0.5180(14) 0.028 Uiso 1 1 d . . . H12B H 0.857(4) 0.9629(18) 0.5639(15) 0.028 Uiso 1 1 d . . . C13 C 1.1651(4) 0.82656(15) 0.60018(12) 0.0162(4) Uani 1 1 d . . . N14 N 1.2936(3) 0.74579(12) 0.61215(9) 0.0177(4) Uani 1 1 d . . . C15 C 1.2096(4) 0.65927(15) 0.58133(12) 0.0170(4) Uani 1 1 d . . . C16 C 0.9983(4) 0.65505(15) 0.53780(12) 0.0189(4) Uani 1 1 d . . . H16A H 0.9438 0.5922 0.5168 0.023 Uiso 1 1 calc R . . C21 C 0.1766(3) 0.77085(15) 0.34240(11) 0.0150(4) Uani 1 1 d . . . C27 C 0.3645(4) 0.78662(15) 0.40553(12) 0.0170(4) Uani 1 1 d . . . O21 O 0.5105(3) 0.70978(11) 0.41668(9) 0.0221(3) Uani 1 1 d . . . H21 H 0.607(4) 0.7212(18) 0.4524(14) 0.026 Uiso 1 1 d . . . O22 O 0.3774(3) 0.86477(10) 0.44311(8) 0.0212(3) Uani 1 1 d . . . C22 C 0.0569(4) 0.67993(15) 0.32800(12) 0.0180(4) Uani 1 1 d . . . F22 F 0.1258(2) 0.59783(9) 0.37054(7) 0.0267(3) Uani 1 1 d . . . C23 C -0.1327(4) 0.66994(16) 0.27454(12) 0.0206(5) Uani 1 1 d . . . H23A H -0.2109 0.6068 0.2671 0.025 Uiso 1 1 calc R . . C24 C -0.2069(4) 0.75411(16) 0.23189(12) 0.0220(5) Uani 1 1 d . . . H24A H -0.3395 0.7489 0.1955 0.026 Uiso 1 1 calc R . . C25 C -0.0905(4) 0.84548(16) 0.24160(12) 0.0201(5) Uani 1 1 d . . . H25A H -0.1390 0.9027 0.2115 0.024 Uiso 1 1 calc R . . C26 C 0.0972(4) 0.85153(14) 0.29591(12) 0.0176(4) Uani 1 1 d . . . F26 F 0.2148(2) 0.94052(9) 0.30377(7) 0.0252(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02097(12) 0.01777(11) 0.02862(14) -0.00432(8) -0.00497(10) -0.00411(8) Br2 0.02164(12) 0.01810(11) 0.02937(14) -0.00054(8) -0.00569(10) 0.00393(8) N11 0.0156(9) 0.0174(8) 0.0179(9) -0.0010(7) -0.0030(7) -0.0015(7) C12 0.0168(10) 0.0194(10) 0.0139(11) 0.0004(8) 0.0010(9) -0.0015(8) N12 0.0183(10) 0.0183(9) 0.0306(12) -0.0033(8) -0.0096(9) 0.0009(8) C13 0.0172(10) 0.0170(9) 0.0140(10) -0.0017(8) -0.0013(8) -0.0038(8) N14 0.0161(9) 0.0193(9) 0.0173(9) -0.0002(7) -0.0010(7) -0.0028(7) C15 0.0177(11) 0.0162(9) 0.0165(11) 0.0003(8) -0.0028(9) 0.0016(8) C16 0.0197(11) 0.0173(10) 0.0192(12) -0.0029(8) -0.0014(9) -0.0011(8) C21 0.0139(10) 0.0167(9) 0.0142(11) -0.0007(8) -0.0003(8) 0.0000(7) C27 0.0152(10) 0.0176(10) 0.0181(11) 0.0020(8) 0.0005(9) -0.0007(8) O21 0.0201(8) 0.0203(8) 0.0239(9) -0.0043(6) -0.0126(7) 0.0041(6) O22 0.0232(8) 0.0179(7) 0.0215(8) -0.0048(6) -0.0056(6) 0.0009(6) C22 0.0197(11) 0.0161(9) 0.0179(11) -0.0002(8) -0.0012(9) 0.0004(8) F22 0.0314(7) 0.0159(6) 0.0311(8) 0.0043(5) -0.0105(6) -0.0033(5) C23 0.0204(11) 0.0210(10) 0.0200(12) -0.0065(9) -0.0022(9) -0.0017(9) C24 0.0169(10) 0.0294(12) 0.0191(12) -0.0068(9) -0.0036(9) 0.0023(9) C25 0.0217(11) 0.0207(10) 0.0174(12) -0.0008(8) -0.0028(9) 0.0053(8) C26 0.0193(11) 0.0142(9) 0.0192(12) -0.0030(8) -0.0009(9) -0.0002(8) F26 0.0296(7) 0.0146(6) 0.0300(8) 0.0035(5) -0.0089(6) -0.0042(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C13 1.893(2) . ? Br2 C15 1.8916(19) . ? N11 C12 1.345(3) . ? N11 C16 1.351(3) . ? C12 N12 1.336(3) . ? C12 C13 1.425(3) . ? N12 H12A 0.81(3) . ? N12 H12B 0.82(3) . ? C13 N14 1.301(2) . ? N14 C15 1.337(2) . ? C15 C16 1.372(3) . ? C16 H16A 0.9500 . ? C21 C26 1.394(3) . ? C21 C22 1.395(3) . ? C21 C27 1.489(3) . ? C27 O22 1.222(2) . ? C27 O21 1.316(2) . ? O21 H21 0.81(3) . ? C22 F22 1.355(2) . ? C22 C23 1.377(3) . ? C23 C24 1.386(3) . ? C23 H23A 0.9500 . ? C24 C25 1.382(3) . ? C24 H24A 0.9500 . ? C25 C26 1.374(3) . ? C25 H25A 0.9500 . ? C26 F26 1.355(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 118.92(18) . . ? N12 C12 N11 118.73(18) . . ? N12 C12 C13 123.67(19) . . ? N11 C12 C13 117.59(18) . . ? C12 N12 H12A 113.5(18) . . ? C12 N12 H12B 118.2(18) . . ? H12A N12 H12B 128(3) . . ? N14 C13 C12 123.53(18) . . ? N14 C13 Br1 116.96(15) . . ? C12 C13 Br1 119.50(15) . . ? C13 N14 C15 117.34(18) . . ? N14 C15 C16 121.88(18) . . ? N14 C15 Br2 117.42(15) . . ? C16 C15 Br2 120.70(15) . . ? N11 C16 C15 120.73(18) . . ? N11 C16 H16A 119.6 . . ? C15 C16 H16A 119.6 . . ? C26 C21 C22 115.02(18) . . ? C26 C21 C27 120.30(17) . . ? C22 C21 C27 124.54(18) . . ? O22 C27 O21 124.14(19) . . ? O22 C27 C21 121.64(18) . . ? O21 C27 C21 114.23(17) . . ? C27 O21 H21 110.6(17) . . ? F22 C22 C23 118.19(18) . . ? F22 C22 C21 118.35(18) . . ? C23 C22 C21 123.43(19) . . ? C22 C23 C24 118.47(19) . . ? C22 C23 H23A 120.8 . . ? C24 C23 H23A 120.8 . . ? C25 C24 C23 120.8(2) . . ? C25 C24 H24A 119.6 . . ? C23 C24 H24A 119.6 . . ? C26 C25 C24 118.38(19) . . ? C26 C25 H25A 120.8 . . ? C24 C25 H25A 120.8 . . ? F26 C26 C25 118.16(18) . . ? F26 C26 C21 118.02(18) . . ? C25 C26 C21 123.80(18) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 N12 179.91(19) . . . . ? C16 N11 C12 C13 1.0(3) . . . . ? N12 C12 C13 N14 -178.9(2) . . . . ? N11 C12 C13 N14 0.0(3) . . . . ? N12 C12 C13 Br1 -0.1(3) . . . . ? N11 C12 C13 Br1 178.81(14) . . . . ? C12 C13 N14 C15 -0.9(3) . . . . ? Br1 C13 N14 C15 -179.77(15) . . . . ? C13 N14 C15 C16 0.9(3) . . . . ? C13 N14 C15 Br2 -179.69(15) . . . . ? C12 N11 C16 C15 -1.0(3) . . . . ? N14 C15 C16 N11 0.1(3) . . . . ? Br2 C15 C16 N11 -179.33(15) . . . . ? C26 C21 C27 O22 35.4(3) . . . . ? C22 C21 C27 O22 -140.1(2) . . . . ? C26 C21 C27 O21 -144.91(19) . . . . ? C22 C21 C27 O21 39.5(3) . . . . ? C26 C21 C22 F22 179.42(18) . . . . ? C27 C21 C22 F22 -4.8(3) . . . . ? C26 C21 C22 C23 -2.8(3) . . . . ? C27 C21 C22 C23 173.01(19) . . . . ? F22 C22 C23 C24 178.79(19) . . . . ? C21 C22 C23 C24 1.0(3) . . . . ? C22 C23 C24 C25 1.3(3) . . . . ? C23 C24 C25 C26 -1.5(3) . . . . ? C24 C25 C26 F26 178.25(18) . . . . ? C24 C25 C26 C21 -0.4(3) . . . . ? C22 C21 C26 F26 -176.20(17) . . . . ? C27 C21 C26 F26 7.8(3) . . . . ? C22 C21 C26 C25 2.5(3) . . . . ? C27 C21 C26 C25 -173.46(19) . . . . ? 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_site_symmetry_A O21 H21 N11 0.81(3) 1.88(3) 2.685(2) 171(2) . N12 H12A O22 0.81(3) 2.17(3) 2.976(3) 174(2) . N12 H12B F26 0.82(3) 2.68(3) 3.335(2) 138(2) 3_676 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.704 _refine_diff_density_min -0.653 _refine_diff_density_rms 0.111 #END