# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _audit_creation_method 'SHELXL-97 plus manual editing' _journal_coden_Cambridge 182 loop_ _publ_author_name 'Andrew Bond' _publ_contact_author_name 'Andrew D. Bond' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UK ; _publ_contact_author_email adb29@cam.ac.uk _publ_contact_author_fax '(01223) 336362' _publ_contact_author_phone '(01223) 336352' _publ_requested_journal 'Chemical Communications' _publ_section_title ; In situ co-crystallisation as a tool for low-temperature crystal engineering ; data_ab0210 _database_code_CSD 192849 _chemical_name_systematic ? _chemical_name_common 'pyrazine / formic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C H2 O2)' _chemical_formula_sum 'C6 H8 N2 O4' _chemical_formula_weight 172.14 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 P21/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 3.6994(1) _cell_length_b 7.0340(3) _cell_length_c 16.1607(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.068(2) _cell_angle_gamma 90.00 _cell_volume 418.17(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3743 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.35 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 180 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9604 _exptl_absorpt_correction_T_max 0.9771 _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm capillary at ca. 280 K. More than one crystal present - only reflections associated with the major component included in the integration - reflected in relatively high R(int). ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 2895 _diffrn_reflns_av_R_equivalents 0.1556 _diffrn_reflns_av_sigmaI/netI 0.0862 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 25.32 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.981 _reflns_number_total 760 _reflns_number_gt 661 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.1003P)^2^+0.0876P] 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 760 _refine_ls_number_parameters 59 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0787 _refine_ls_R_factor_gt 0.0723 _refine_ls_wR_factor_ref 0.1925 _refine_ls_wR_factor_gt 0.1839 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.334 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.066 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 O1 O 0.3994(5) 0.9644(2) 0.38667(10) 0.0559(6) Uani 1 1 d . . . H1 H 0.281(11) 0.873(5) 0.414(2) 0.096(11) Uiso 1 1 d . . . O2 O 0.1775(5) 0.8171(2) 0.26999(10) 0.0597(6) Uani 1 1 d . . . C1 C 0.3318(6) 0.9476(3) 0.30605(14) 0.0510(7) Uani 1 1 d . . . H1A H 0.4120 1.0478 0.2730 0.061 Uiso 1 1 calc R . . N1A N 0.1374(5) 0.6608(2) 0.46444(11) 0.0455(6) Uani 1 1 d . . . C2A C 0.0975(6) 0.6525(3) 0.54571(13) 0.0464(7) Uani 1 1 d . . . H2AA H 0.1640 0.7592 0.5800 0.056 Uiso 1 1 calc R . . C1A C 0.0379(6) 0.5075(3) 0.41936(13) 0.0469(7) Uani 1 1 d . . . H1AA H 0.0610 0.5086 0.3614 0.056 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 O1 0.0709(12) 0.0392(10) 0.0575(11) 0.0018(7) 0.0061(8) -0.0146(7) O2 0.0789(13) 0.0437(10) 0.0562(11) -0.0006(7) 0.0060(9) -0.0058(8) C1 0.0608(14) 0.0362(11) 0.0569(13) 0.0045(9) 0.0097(11) -0.0025(9) N1A 0.0480(11) 0.0369(10) 0.0516(11) 0.0019(7) 0.0049(8) -0.0038(7) C2A 0.0505(13) 0.0372(11) 0.0510(12) -0.0080(9) 0.0036(9) -0.0037(8) C1A 0.0528(13) 0.0454(12) 0.0426(11) -0.0014(9) 0.0051(10) -0.0026(8) _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 O1 C1 1.306(3) . ? O1 H1 0.92(4) . ? O2 C1 1.199(3) . ? C1 H1A 0.9500 . ? N1A C1A 1.331(3) . ? N1A C2A 1.338(3) . ? C2A C1A 1.377(3) 3_566 ? C2A H2AA 0.9500 . ? C1A C2A 1.377(3) 3_566 ? C1A H1AA 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 C1 O1 H1 111(2) . . ? O2 C1 O1 125.8(2) . . ? O2 C1 H1A 117.1 . . ? O1 C1 H1A 117.1 . . ? C1A N1A C2A 116.64(17) . . ? N1A C2A C1A 121.39(18) . 3_566 ? N1A C2A H2AA 119.3 . . ? C1A C2A H2AA 119.3 3_566 . ? N1A C1A C2A 121.96(18) . 3_566 ? N1A C1A H1AA 119.0 . . ? C2A C1A H1AA 119.0 3_566 . ? 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 C1A N1A C2A C1A 0.4(3) . . . 3_566 ? C2A N1A C1A C2A -0.4(3) . . . 3_566 ? #===END data_ab0209 _database_code_CSD 192850 _chemical_name_systematic ? _chemical_name_common 'pyrazine / acetic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C2 H4 O2)' _chemical_formula_sum 'C8 H12 N2 O4' _chemical_formula_weight 200.20 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 5.4869(2) _cell_length_b 8.1885(2) _cell_length_c 11.9960(4) _cell_angle_alpha 70.076(1) _cell_angle_beta 86.667(1) _cell_angle_gamma 89.925(2) _cell_volume 505.76(3) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3505 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm capillary at ca. 275 K ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 5274 _diffrn_reflns_av_R_equivalents 0.0719 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.979 _reflns_number_total 2287 _reflns_number_gt 1904 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0677P)^2^+0.1511P] 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 2287 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1499 _refine_ls_wR_factor_gt 0.1370 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.240 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.046 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 O2_1 O -0.1440(2) 0.32153(17) -0.00707(11) 0.0460(3) Uani 1 1 d . . . O1_1 O -0.0215(2) 0.20358(16) 0.17682(10) 0.0426(3) Uani 1 1 d . . . H1_1 H 0.093(5) 0.149(3) 0.136(2) 0.077(8) Uiso 1 1 d . . . C1_1 C -0.1633(3) 0.3057(2) 0.09716(15) 0.0353(3) Uani 1 1 d . . . C2_1 C -0.3504(3) 0.3953(2) 0.15031(16) 0.0444(4) Uani 1 1 d . . . H2A_1 H -0.4125 0.4950 0.0875 0.067 Uiso 1 1 calc R . . H2B_1 H -0.2757 0.4354 0.2089 0.067 Uiso 1 1 calc R . . H2C_1 H -0.4854 0.3140 0.1894 0.067 Uiso 1 1 calc R . . N1A_1 N 0.3190(2) 0.05536(18) 0.06390(12) 0.0380(3) Uani 1 1 d . . . C1A_1 C 0.3234(3) 0.1024(2) -0.05361(16) 0.0392(4) Uani 1 1 d . . . H1AA_1 H 0.1993 0.1753 -0.0950 0.047 Uiso 1 1 calc R . . C2A_1 C 0.4952(3) -0.0477(2) 0.11734(15) 0.0388(4) Uani 1 1 d . . . H2AA_1 H 0.4971 -0.0850 0.2014 0.047 Uiso 1 1 calc R . . O2_2 O 0.2155(2) 0.44093(17) -0.39220(12) 0.0484(3) Uani 1 1 d . . . O1_2 O -0.0370(2) 0.21128(15) -0.33587(11) 0.0419(3) Uani 1 1 d . . . H1_2 H 0.093(4) 0.163(3) -0.370(2) 0.064(6) Uiso 1 1 d . . . C1_2 C 0.0194(3) 0.3743(2) -0.34952(13) 0.0314(3) Uani 1 1 d . . . C2_2 C -0.1833(3) 0.4641(2) -0.30628(15) 0.0372(4) Uani 1 1 d . . . H2D_2 H -0.1449 0.5887 -0.3315 0.056 Uiso 1 1 calc R . . H2E_2 H -0.2020 0.4161 -0.2194 0.056 Uiso 1 1 calc R . . H2F_2 H -0.3357 0.4461 -0.3396 0.056 Uiso 1 1 calc R . . N1A_2 N 0.3211(2) 0.06645(17) -0.44135(12) 0.0353(3) Uani 1 1 d . . . C2A_2 C 0.3004(3) -0.0921(2) -0.44764(15) 0.0367(4) Uani 1 1 d . . . H2AB_2 H 0.1598 -0.1616 -0.4110 0.044 Uiso 1 1 calc R . . C1A_2 C 0.5214(3) 0.1588(2) -0.49370(14) 0.0343(3) Uani 1 1 d . . . H1AB_2 H 0.5429 0.2724 -0.4909 0.041 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 O2_1 0.0520(7) 0.0544(8) 0.0366(6) -0.0227(6) 0.0011(5) 0.0095(6) O1_1 0.0413(6) 0.0514(7) 0.0375(6) -0.0190(5) 0.0030(5) 0.0167(5) C1_1 0.0339(7) 0.0366(8) 0.0383(8) -0.0176(6) 0.0036(6) 0.0016(6) C2_1 0.0428(9) 0.0526(10) 0.0458(10) -0.0269(8) -0.0030(7) 0.0172(7) N1A_1 0.0338(7) 0.0405(7) 0.0434(8) -0.0211(6) 0.0097(5) 0.0011(5) C1A_1 0.0354(8) 0.0379(8) 0.0445(9) -0.0143(7) -0.0009(6) 0.0056(6) C2A_1 0.0427(8) 0.0420(9) 0.0324(8) -0.0145(7) 0.0049(6) -0.0013(6) O2_2 0.0320(6) 0.0568(8) 0.0634(8) -0.0320(7) 0.0114(5) -0.0059(5) O1_2 0.0367(6) 0.0396(6) 0.0525(7) -0.0225(5) 0.0141(5) 0.0028(5) C1_2 0.0293(7) 0.0405(8) 0.0277(7) -0.0163(6) 0.0004(5) 0.0040(6) C2_2 0.0339(8) 0.0411(8) 0.0405(8) -0.0197(7) 0.0027(6) 0.0069(6) N1A_2 0.0333(6) 0.0392(7) 0.0360(7) -0.0173(6) 0.0046(5) 0.0060(5) C2A_2 0.0317(7) 0.0384(8) 0.0399(8) -0.0143(7) 0.0050(6) 0.0007(6) C1A_2 0.0353(7) 0.0333(7) 0.0372(8) -0.0165(6) 0.0005(6) 0.0038(6) _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 O2_1 C1_1 1.211(2) . ? O1_1 C1_1 1.326(2) . ? O1_1 H1_1 0.97(3) . ? C1_1 C2_1 1.496(2) . ? C2_1 H2A_1 0.9800 . ? C2_1 H2B_1 0.9800 . ? C2_1 H2C_1 0.9800 . ? N1A_1 C2A_1 1.327(2) . ? N1A_1 C1A_1 1.327(2) . ? C1A_1 C2A_1 1.385(2) 2_655 ? C1A_1 H1AA_1 0.9500 . ? C2A_1 C1A_1 1.385(2) 2_655 ? C2A_1 H2AA_1 0.9500 . ? O2_2 C1_2 1.2101(18) . ? O1_2 C1_2 1.3235(19) . ? O1_2 H1_2 0.95(3) . ? C1_2 C2_2 1.4952(19) . ? C2_2 H2D_2 0.9800 . ? C2_2 H2E_2 0.9800 . ? C2_2 H2F_2 0.9800 . ? N1A_2 C2A_2 1.331(2) . ? N1A_2 C1A_2 1.331(2) . ? C2A_2 C1A_2 1.389(2) 2_654 ? C2A_2 H2AB_2 0.9500 . ? C1A_2 C2A_2 1.389(2) 2_654 ? C1A_2 H1AB_2 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 C1_1 O1_1 H1_1 108.3(15) . . ? O2_1 C1_1 O1_1 122.94(14) . . ? O2_1 C1_1 C2_1 124.15(15) . . ? O1_1 C1_1 C2_1 112.90(14) . . ? C1_1 C2_1 H2A_1 109.5 . . ? C1_1 C2_1 H2B_1 109.5 . . ? H2A_1 C2_1 H2B_1 109.5 . . ? C1_1 C2_1 H2C_1 109.5 . . ? H2A_1 C2_1 H2C_1 109.5 . . ? H2B_1 C2_1 H2C_1 109.5 . . ? C2A_1 N1A_1 C1A_1 116.79(13) . . ? N1A_1 C1A_1 C2A_1 121.54(15) . 2_655 ? N1A_1 C1A_1 H1AA_1 119.2 . . ? C2A_1 C1A_1 H1AA_1 119.2 2_655 . ? N1A_1 C2A_1 C1A_1 121.67(15) . 2_655 ? N1A_1 C2A_1 H2AA_1 119.2 . . ? C1A_1 C2A_1 H2AA_1 119.2 2_655 . ? C1_2 O1_2 H1_2 109.6(14) . . ? O2_2 C1_2 O1_2 122.66(14) . . ? O2_2 C1_2 C2_2 124.60(15) . . ? O1_2 C1_2 C2_2 112.75(13) . . ? C1_2 C2_2 H2D_2 109.5 . . ? C1_2 C2_2 H2E_2 109.5 . . ? H2D_2 C2_2 H2E_2 109.5 . . ? C1_2 C2_2 H2F_2 109.5 . . ? H2D_2 C2_2 H2F_2 109.5 . . ? H2E_2 C2_2 H2F_2 109.5 . . ? C2A_2 N1A_2 C1A_2 116.97(13) . . ? N1A_2 C2A_2 C1A_2 121.82(14) . 2_654 ? N1A_2 C2A_2 H2AB_2 119.1 . . ? C1A_2 C2A_2 H2AB_2 119.1 2_654 . ? N1A_2 C1A_2 C2A_2 121.21(14) . 2_654 ? N1A_2 C1A_2 H1AB_2 119.4 . . ? C2A_2 C1A_2 H1AB_2 119.4 2_654 . ? 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 C2A_1 N1A_1 C1A_1 C2A_1 -0.6(3) . . . 2_655 ? C1A_1 N1A_1 C2A_1 C1A_1 0.6(3) . . . 2_655 ? C1A_2 N1A_2 C2A_2 C1A_2 -0.2(3) . . . 2_654 ? C2A_2 N1A_2 C1A_2 C2A_2 0.2(2) . . . 2_654 ? #===END data_ab0206 _database_code_CSD 192851 _chemical_name_systematic ? _chemical_name_common 'pyrazine / propanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C3 H6 O2)' _chemical_formula_sum 'C10 H16 N2 O4' _chemical_formula_weight 228.25 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 P21/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 4.8735(2) _cell_length_b 5.4384(2) _cell_length_c 23.2428(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.197(1) _cell_angle_gamma 90.00 _cell_volume 615.07(4) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6268 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm glass capillary at ca. 260 K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 1845 _diffrn_reflns_av_R_equivalents 0.1186 _diffrn_reflns_av_sigmaI/netI 0.0950 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 24.89 _diffrn_measured_fraction_theta_max 0.830 _diffrn_reflns_theta_full 24.89 _diffrn_measured_fraction_theta_full 0.830 _reflns_number_total 891 _reflns_number_gt 664 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1127P)^2^+0.0802P] 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 SHELXL _refine_ls_extinction_coef 0.49(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 891 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0749 _refine_ls_wR_factor_ref 0.2189 _refine_ls_wR_factor_gt 0.1880 _refine_ls_goodness_of_fit_ref 1.245 _refine_ls_restrained_S_all 1.245 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.409 _refine_diff_density_min -0.531 _refine_diff_density_rms 0.150 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 O1 O -0.0472(6) 0.0299(5) 0.35779(10) 0.0555(10) Uani 1 1 d . . . H1 H 0.057(14) 0.006(12) 0.395(3) 0.120(19) Uiso 1 1 d . . . O2 O -0.1888(6) 0.3590(4) 0.40456(9) 0.0553(10) Uani 1 1 d . . . C1 C -0.2008(8) 0.2286(6) 0.36272(13) 0.0425(10) Uani 1 1 d . . . C2 C -0.3934(9) 0.2707(7) 0.31092(13) 0.0555(12) Uani 1 1 d . . . H2A H -0.2847 0.2777 0.2762 0.067 Uiso 1 1 calc R . . H2B H -0.5192 0.1281 0.3065 0.067 Uiso 1 1 calc R . . C3 C -0.5613(9) 0.4995(8) 0.31349(15) 0.0601(13) Uani 1 1 d . . . H3A H -0.6772 0.4910 0.3465 0.090 Uiso 1 1 calc R . . H3B H -0.6777 0.5156 0.2779 0.090 Uiso 1 1 calc R . . H3C H -0.4391 0.6423 0.3177 0.090 Uiso 1 1 calc R . . N1A N 0.3126(6) -0.0090(5) 0.45274(10) 0.0458(10) Uani 1 1 d . . . C2A C 0.5076(8) -0.1786(6) 0.46148(13) 0.0472(11) Uani 1 1 d . . . H2AA H 0.5200 -0.3090 0.4346 0.057 Uiso 1 1 calc R . . C1A C 0.3083(8) 0.1696(6) 0.49136(13) 0.0479(11) Uani 1 1 d . . . H1AA H 0.1740 0.2955 0.4864 0.058 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 O1 0.062(2) 0.0474(16) 0.0559(15) -0.0087(10) -0.0049(12) 0.0122(12) O2 0.059(2) 0.0550(16) 0.0501(14) -0.0109(10) -0.0088(10) 0.0183(13) C1 0.042(3) 0.0406(18) 0.0452(17) -0.0003(13) 0.0043(13) -0.0046(16) C2 0.063(3) 0.053(2) 0.048(2) -0.0052(14) -0.0098(16) 0.0051(19) C3 0.061(3) 0.059(2) 0.058(2) 0.0043(15) -0.0144(18) 0.0068(19) N1A 0.045(3) 0.0424(17) 0.0499(16) 0.0002(11) 0.0016(12) 0.0048(13) C2A 0.051(3) 0.0384(18) 0.0525(19) -0.0036(13) 0.0047(14) 0.0081(16) C1A 0.050(3) 0.0401(19) 0.0542(19) -0.0012(13) 0.0029(15) 0.0084(16) _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 O1 C1 1.323(4) . ? O1 H1 0.98(6) . ? O2 C1 1.203(4) . ? C1 C2 1.502(5) . ? C2 C3 1.492(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? N1A C1A 1.323(4) . ? N1A C2A 1.332(4) . ? C2A C1A 1.378(5) 3_656 ? C2A H2AA 0.9500 . ? C1A C2A 1.378(5) 3_656 ? C1A H1AA 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 C1 O1 H1 107(4) . . ? O2 C1 O1 123.3(3) . . ? O2 C1 C2 123.9(3) . . ? O1 C1 C2 112.7(3) . . ? C3 C2 C1 114.5(3) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1A N1A C2A 116.3(3) . . ? N1A C2A C1A 121.6(3) . 3_656 ? N1A C2A H2AA 119.2 . . ? C1A C2A H2AA 119.2 3_656 . ? N1A C1A C2A 122.1(3) . 3_656 ? N1A C1A H1AA 118.9 . . ? C2A C1A H1AA 118.9 3_656 . ? 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 O2 C1 C2 C3 3.6(6) . . . . ? O1 C1 C2 C3 -177.3(3) . . . . ? C1A N1A C2A C1A 0.8(6) . . . 3_656 ? C2A N1A C1A C2A -0.9(6) . . . 3_656 ? #===END data_ab0207 _database_code_CSD 192852 _chemical_name_systematic ? _chemical_name_common 'pyrazine / butanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C4 H8 O2)' _chemical_formula_sum 'C12 H20 N2 O4' _chemical_formula_weight 256.30 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 P21/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 9.8544(7) _cell_length_b 5.7127(4) _cell_length_c 13.5338(13) _cell_angle_alpha 90.00 _cell_angle_beta 109.736(3) _cell_angle_gamma 90.00 _cell_volume 717.13(10) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7873 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm glass capillary at ca. 265 K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 3855 _diffrn_reflns_av_R_equivalents 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.91 _diffrn_reflns_theta_max 25.03 _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.982 _reflns_number_total 1245 _reflns_number_gt 1023 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0465P)^2^+0.2173P] 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 1245 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.1058 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.165 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.033 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 O1 O -0.25942(18) 0.0583(3) 0.00876(9) 0.0704(5) Uani 1 1 d . . . H1 H -0.200(3) -0.063(5) 0.007(2) 0.097(8) Uiso 1 1 d . . . O2 O -0.31294(15) 0.0311(2) -0.16337(9) 0.0594(4) Uani 1 1 d . . . C1 C -0.33206(18) 0.1209(3) -0.08890(12) 0.0439(4) Uani 1 1 d . . . C2 C -0.43771(19) 0.3128(3) -0.09522(12) 0.0493(5) Uani 1 1 d . . . H2A H -0.3865 0.4439 -0.0502 0.059 Uiso 1 1 calc R . . H2B H -0.5113 0.2544 -0.0664 0.059 Uiso 1 1 calc R . . C3 C -0.51327(19) 0.4051(3) -0.20463(13) 0.0495(5) Uani 1 1 d . . . H3A H -0.5644 0.2747 -0.2503 0.059 Uiso 1 1 calc R . . H3B H -0.4405 0.4669 -0.2334 0.059 Uiso 1 1 calc R . . C4 C -0.6208(2) 0.5973(3) -0.20682(14) 0.0581(5) Uani 1 1 d . . . H4A H -0.6723 0.6432 -0.2797 0.087 Uiso 1 1 calc R . . H4B H -0.5695 0.7331 -0.1673 0.087 Uiso 1 1 calc R . . H4C H -0.6900 0.5397 -0.1749 0.087 Uiso 1 1 calc R . . N1A N -0.08164(15) -0.3083(2) 0.00979(10) 0.0466(4) Uani 1 1 d . . . C2A C 0.0126(2) -0.4124(3) 0.09338(12) 0.0485(5) Uani 1 1 d . . . H2AA H 0.0243 -0.3536 0.1614 0.058 Uiso 1 1 calc R . . C1A C -0.09307(19) -0.3984(3) -0.08378(12) 0.0455(4) Uani 1 1 d . . . H1AA H -0.1587 -0.3297 -0.1453 0.055 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 O1 0.0896(11) 0.0855(10) 0.0310(7) 0.0054(6) 0.0137(6) 0.0416(9) O2 0.0710(9) 0.0671(8) 0.0333(7) -0.0030(6) 0.0087(6) 0.0215(7) C1 0.0483(10) 0.0491(10) 0.0311(8) -0.0002(7) 0.0094(7) 0.0025(7) C2 0.0533(10) 0.0537(10) 0.0401(9) -0.0004(7) 0.0148(8) 0.0068(8) C3 0.0500(10) 0.0531(10) 0.0429(9) 0.0036(7) 0.0124(8) 0.0064(8) C4 0.0591(12) 0.0579(12) 0.0531(11) 0.0056(8) 0.0135(9) 0.0117(9) N1A 0.0534(9) 0.0515(9) 0.0317(7) 0.0016(6) 0.0099(6) 0.0074(6) C2A 0.0595(11) 0.0540(10) 0.0274(8) -0.0010(7) 0.0086(7) 0.0054(8) C1A 0.0496(10) 0.0523(10) 0.0293(8) 0.0041(7) 0.0063(7) 0.0052(7) _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 O1 C1 1.3222(19) . ? O1 H1 0.91(3) . ? O2 C1 1.2013(19) . ? C1 C2 1.494(2) . ? C2 C3 1.510(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.520(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? N1A C1A 1.336(2) . ? N1A C2A 1.337(2) . ? C2A C1A 1.372(2) 3_545 ? C2A H2AA 0.9500 . ? C1A C2A 1.372(2) 3_545 ? C1A H1AA 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 C1 O1 H1 108.4(16) . . ? O2 C1 O1 122.53(16) . . ? O2 C1 C2 124.68(14) . . ? O1 C1 C2 112.79(14) . . ? C1 C2 C3 114.56(13) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C2 C3 C4 112.41(14) . . ? C2 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? C2 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C1A N1A C2A 116.28(14) . . ? N1A C2A C1A 121.93(14) . 3_545 ? N1A C2A H2AA 119.0 . . ? C1A C2A H2AA 119.0 3_545 . ? N1A C1A C2A 121.79(14) . 3_545 ? N1A C1A H1AA 119.1 . . ? C2A C1A H1AA 119.1 3_545 . ? 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 O2 C1 C2 C3 -5.1(3) . . . . ? O1 C1 C2 C3 174.66(16) . . . . ? C1 C2 C3 C4 179.24(16) . . . . ? C1A N1A C2A C1A -0.1(3) . . . 3_545 ? C2A N1A C1A C2A 0.1(3) . . . 3_545 ? #===END data_ab0208 _database_code_CSD 192853 _chemical_name_systematic ? _chemical_name_common 'pyrazine / pentanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C5 H10 O2)' _chemical_formula_sum 'C14 H24 N2 O4' _chemical_formula_weight 284.35 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 P21/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 13.24490(11) _cell_length_b 5.4022(3) _cell_length_c 11.9960(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.716(3) _cell_angle_gamma 90.00 _cell_volume 826.24(7) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7756 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.143 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm capillary at ca. 268 K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4881 _diffrn_reflns_av_R_equivalents 0.1216 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 24.71 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.979 _reflns_number_total 1374 _reflns_number_gt 1072 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0742P)^2^+0.6852P] 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 1374 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0943 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.1962 _refine_ls_wR_factor_gt 0.1790 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.213 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.058 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 O2 O 0.35882(17) 0.1553(4) 0.63730(19) 0.0508(7) Uani 1 1 d . . . O1 O 0.27470(18) 0.0369(4) 0.45876(18) 0.0520(7) Uani 1 1 d . . . H1 H 0.339(3) -0.093(8) 0.477(3) 0.072(11) Uiso 1 1 d . . . C1 C 0.2857(2) 0.1765(5) 0.5524(2) 0.0383(7) Uani 1 1 d . . . C2 C 0.1978(2) 0.3573(6) 0.5395(3) 0.0434(8) Uani 1 1 d . . . H2A H 0.1315 0.2633 0.5262 0.052 Uiso 1 1 calc R . . H2B H 0.1934 0.4585 0.4696 0.052 Uiso 1 1 calc R . . C3 C 0.2061(2) 0.5307(6) 0.6410(2) 0.0418(7) Uani 1 1 d . . . H3A H 0.2175 0.4325 0.7131 0.050 Uiso 1 1 calc R . . H3B H 0.2674 0.6409 0.6493 0.050 Uiso 1 1 calc R . . C4 C 0.1081(2) 0.6863(6) 0.6251(3) 0.0474(8) Uani 1 1 d . . . H4A H 0.0469 0.5751 0.6152 0.057 Uiso 1 1 calc R . . H4B H 0.0975 0.7854 0.5534 0.057 Uiso 1 1 calc R . . C5 C 0.1127(3) 0.8597(7) 0.7261(3) 0.0583(9) Uani 1 1 d . . . H5A H 0.1190 0.7624 0.7966 0.087 Uiso 1 1 calc R . . H5B H 0.0486 0.9594 0.7098 0.087 Uiso 1 1 calc R . . H5C H 0.1737 0.9691 0.7372 0.087 Uiso 1 1 calc R . . N1A N 0.42684(19) -0.3099(5) 0.4842(2) 0.0440(7) Uani 1 1 d . . . C2A C 0.4286(2) -0.4696(6) 0.3993(3) 0.0467(8) Uani 1 1 d . . . H2AA H 0.3784 -0.4526 0.3263 0.056 Uiso 1 1 calc R . . C1A C 0.4986(2) -0.3421(6) 0.5848(3) 0.0448(8) Uani 1 1 d . . . H1AA H 0.4997 -0.2329 0.6472 0.054 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 O2 0.0519(13) 0.0520(13) 0.0440(12) -0.0013(10) 0.0053(10) 0.0109(10) O1 0.0566(14) 0.0528(14) 0.0437(12) -0.0104(10) 0.0087(9) 0.0155(11) C1 0.0435(16) 0.0363(15) 0.0359(15) 0.0034(12) 0.0121(12) -0.0011(12) C2 0.0498(17) 0.0412(17) 0.0382(16) -0.0010(12) 0.0101(12) 0.0084(13) C3 0.0478(16) 0.0386(16) 0.0396(15) -0.0008(12) 0.0130(12) 0.0025(13) C4 0.0489(18) 0.0444(18) 0.0498(18) -0.0046(14) 0.0146(14) 0.0039(14) C5 0.068(2) 0.051(2) 0.061(2) -0.0108(15) 0.0244(17) 0.0049(16) N1A 0.0448(14) 0.0414(14) 0.0480(15) -0.0033(11) 0.0163(11) 0.0055(11) C2A 0.0439(17) 0.0508(18) 0.0441(17) -0.0055(14) 0.0099(13) 0.0018(14) C1A 0.0496(17) 0.0416(17) 0.0448(17) -0.0103(13) 0.0157(13) -0.0017(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 O2 C1 1.206(3) . ? O1 C1 1.328(4) . ? O1 H1 1.08(4) . ? C1 C2 1.495(4) . ? C2 C3 1.517(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.515(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.520(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? N1A C1A 1.330(4) . ? N1A C2A 1.339(4) . ? C2A C1A 1.379(4) 3_646 ? C2A H2AA 0.9500 . ? C1A C2A 1.379(4) 3_646 ? C1A H1AA 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 C1 O1 H1 107(2) . . ? O2 C1 O1 122.7(3) . . ? O2 C1 C2 125.0(3) . . ? O1 C1 C2 112.3(2) . . ? C1 C2 C3 115.8(2) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 111.6(2) . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 113.1(3) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1A N1A C2A 116.8(3) . . ? N1A C2A C1A 121.7(3) . 3_646 ? N1A C2A H2AA 119.1 . . ? C1A C2A H2AA 119.1 3_646 . ? N1A C1A C2A 121.5(3) . 3_646 ? N1A C1A H1AA 119.3 . . ? C2A C1A H1AA 119.3 3_646 . ? 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 O2 C1 C2 C3 2.4(5) . . . . ? O1 C1 C2 C3 -177.9(3) . . . . ? C1 C2 C3 C4 -173.7(3) . . . . ? C2 C3 C4 C5 179.1(3) . . . . ? C1A N1A C2A C1A -0.2(5) . . . 3_646 ? C2A N1A C1A C2A 0.2(5) . . . 3_646 ? #===END data_ab0204b _database_code_CSD 192854 _chemical_name_systematic ? _chemical_name_common 'pyrazine / hexanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C6 H12 O2)' _chemical_formula_sum 'C16 H28 N2 O4' _chemical_formula_weight 312.40 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.6365(7) _cell_length_b 5.4294(1) _cell_length_c 12.2322(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.639(1) _cell_angle_gamma 90.00 _cell_volume 1829.42(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4824 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm capillary at ca. 280 K. ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 8015 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.51 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 2092 _reflns_number_gt 1690 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0618P)^2^+0.7753P] 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 2092 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1318 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.208 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.035 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 O1 O 0.35251(4) 0.2035(2) 0.54544(8) 0.0513(3) Uani 1 1 d . . . H1 H 0.3278(8) 0.317(5) 0.5361(18) 0.087(7) Uiso 1 1 d . . . O2 O 0.31481(4) 0.1105(2) 0.69393(8) 0.0497(3) Uani 1 1 d . . . C1 C 0.34742(5) 0.0762(2) 0.63625(10) 0.0349(3) Uani 1 1 d . . . C2 C 0.38699(5) -0.1124(2) 0.65743(11) 0.0390(3) Uani 1 1 d . . . H2A H 0.4187 -0.0262 0.6642 0.047 Uiso 1 1 calc R . . H2B H 0.3868 -0.2229 0.5930 0.047 Uiso 1 1 calc R . . C3 C 0.38305(5) -0.2681(2) 0.75876(11) 0.0380(3) Uani 1 1 d . . . H3A H 0.3530 -0.3682 0.7496 0.046 Uiso 1 1 calc R . . H3B H 0.3806 -0.1590 0.8229 0.046 Uiso 1 1 calc R . . C4 C 0.42648(5) -0.4381(2) 0.78051(11) 0.0403(3) Uani 1 1 d . . . H4A H 0.4288 -0.5465 0.7160 0.048 Uiso 1 1 calc R . . H4B H 0.4564 -0.3371 0.7887 0.048 Uiso 1 1 calc R . . C5 C 0.42420(5) -0.5972(3) 0.88183(12) 0.0476(4) Uani 1 1 d . . . H5A H 0.3948 -0.7014 0.8728 0.057 Uiso 1 1 calc R . . H5B H 0.4211 -0.4890 0.9460 0.057 Uiso 1 1 calc R . . C6 C 0.46827(6) -0.7622(3) 0.90479(15) 0.0577(4) Uani 1 1 d . . . H6A H 0.4719 -0.8688 0.8413 0.087 Uiso 1 1 calc R . . H6B H 0.4639 -0.8640 0.9694 0.087 Uiso 1 1 calc R . . H6C H 0.4974 -0.6602 0.9185 0.087 Uiso 1 1 calc R . . N1A N 0.28340(4) 0.5589(2) 0.51130(10) 0.0422(3) Uani 1 1 d . . . C1A C 0.25149(5) 0.5979(3) 0.58522(12) 0.0430(3) Uani 1 1 d . . . H1AA H 0.2516 0.4925 0.6472 0.052 Uiso 1 1 calc R . . C2A C 0.28165(5) 0.7124(3) 0.42590(12) 0.0441(3) Uani 1 1 d . . . H2AA H 0.3038 0.6903 0.3713 0.053 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 O1 0.0547(6) 0.0549(6) 0.0462(6) 0.0191(5) 0.0149(5) 0.0170(5) O2 0.0503(6) 0.0546(6) 0.0464(6) 0.0101(4) 0.0166(5) 0.0160(5) C1 0.0393(7) 0.0334(6) 0.0322(6) 0.0004(5) 0.0036(5) 0.0005(5) C2 0.0418(7) 0.0376(7) 0.0384(7) 0.0028(5) 0.0086(5) 0.0070(5) C3 0.0385(7) 0.0369(7) 0.0392(7) 0.0042(5) 0.0067(5) 0.0058(5) C4 0.0398(7) 0.0375(7) 0.0440(7) 0.0036(5) 0.0067(5) 0.0056(5) C5 0.0451(8) 0.0480(8) 0.0502(8) 0.0113(6) 0.0077(6) 0.0105(6) C6 0.0522(9) 0.0600(10) 0.0607(10) 0.0155(7) 0.0044(7) 0.0173(7) N1A 0.0390(6) 0.0434(6) 0.0439(7) 0.0075(5) 0.0012(5) 0.0050(5) C1A 0.0418(7) 0.0455(8) 0.0415(7) 0.0120(6) 0.0027(6) 0.0010(6) C2A 0.0391(7) 0.0519(8) 0.0418(7) 0.0079(6) 0.0069(5) 0.0044(6) _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 O1 C1 1.3255(15) . ? O1 H1 0.92(2) . ? O2 C1 1.2032(15) . ? C1 C2 1.5053(17) . ? C2 C3 1.5115(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5203(18) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5161(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.520(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? N1A C1A 1.3301(18) . ? N1A C2A 1.3341(18) . ? C1A C2A 1.378(2) 7_566 ? C1A H1AA 0.9500 . ? C2A C1A 1.378(2) 7_566 ? C2A H2AA 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 C1 O1 H1 108.9(14) . . ? O2 C1 O1 123.10(12) . . ? O2 C1 C2 124.94(11) . . ? O1 C1 C2 111.97(11) . . ? C1 C2 C3 114.96(10) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 112.01(11) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 113.86(11) . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4B 108.8 . . ? C3 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C4 C5 C6 113.66(13) . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C6 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1A N1A C2A 116.66(12) . . ? N1A C1A C2A 121.60(12) . 7_566 ? N1A C1A H1AA 119.2 . . ? C2A C1A H1AA 119.2 7_566 . ? N1A C2A C1A 121.73(13) . 7_566 ? N1A C2A H2AA 119.1 . . ? C1A C2A H2AA 119.1 7_566 . ? 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 O2 C1 C2 C3 1.2(2) . . . . ? O1 C1 C2 C3 -178.95(12) . . . . ? C1 C2 C3 C4 -174.91(11) . . . . ? C2 C3 C4 C5 179.72(12) . . . . ? C3 C4 C5 C6 -178.58(13) . . . . ? C2A N1A C1A C2A -0.1(2) . . . 7_566 ? C1A N1A C2A C1A 0.1(2) . . . 7_566 ? #===END data_ab0205 _database_code_CSD 192855 _chemical_name_systematic ? _chemical_name_common 'pyrazine / heptanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C7 H14 O2)' _chemical_formula_sum 'C18 H32 N2 O4' _chemical_formula_weight 340.46 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 5.5106(3) _cell_length_b 6.8970(3) _cell_length_c 13.7860(8) _cell_angle_alpha 76.816(2) _cell_angle_beta 85.697(2) _cell_angle_gamma 76.802(2) _cell_volume 496.53(5) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 7215 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 186 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm glass capillary at ca. 289 K ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 5160 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.974 _reflns_number_total 2210 _reflns_number_gt 1874 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0451P)^2^+0.1191P] 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 2210 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 0.250 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.033 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 O1 O 0.39154(18) 0.25371(15) 0.15556(8) 0.0446(3) Uani 1 1 d . . . H1 H 0.526(4) 0.202(3) 0.1165(15) 0.076(6) Uiso 1 1 d . . . O2 O 0.58217(18) 0.51172(14) 0.13948(8) 0.0457(3) Uani 1 1 d . . . C1 C 0.4098(2) 0.43268(17) 0.17126(9) 0.0308(3) Uani 1 1 d . . . C2 C 0.1937(2) 0.51946(17) 0.23318(9) 0.0327(3) Uani 1 1 d . . . H2A H 0.1920 0.4227 0.2983 0.039 Uiso 1 1 calc R . . H2B H 0.0374 0.5290 0.1996 0.039 Uiso 1 1 calc R . . C3 C 0.1943(2) 0.72802(17) 0.25198(9) 0.0320(3) Uani 1 1 d . . . H3A H 0.2019 0.8256 0.1875 0.038 Uiso 1 1 calc R . . H3B H 0.3441 0.7189 0.2896 0.038 Uiso 1 1 calc R . . C4 C -0.0386(2) 0.80597(18) 0.31074(9) 0.0339(3) Uani 1 1 d . . . H4A H -0.1871 0.8121 0.2730 0.041 Uiso 1 1 calc R . . H4B H -0.0448 0.7067 0.3748 0.041 Uiso 1 1 calc R . . C5 C -0.0534(2) 1.01495(18) 0.33238(9) 0.0336(3) Uani 1 1 d . . . H5A H -0.0619 1.1172 0.2686 0.040 Uiso 1 1 calc R . . H5B H 0.1002 1.0127 0.3659 0.040 Uiso 1 1 calc R . . C6 C -0.2789(2) 1.07887(19) 0.39795(10) 0.0385(3) Uani 1 1 d . . . H6A H -0.2711 0.9749 0.4611 0.046 Uiso 1 1 calc R . . H6B H -0.4321 1.0820 0.3639 0.046 Uiso 1 1 calc R . . C7 C -0.2973(3) 1.2866(2) 0.42212(11) 0.0471(4) Uani 1 1 d . . . H7A H -0.1489 1.2838 0.4579 0.071 Uiso 1 1 calc R . . H7B H -0.4464 1.3185 0.4639 0.071 Uiso 1 1 calc R . . H7C H -0.3084 1.3911 0.3601 0.071 Uiso 1 1 calc R . . N1A N 0.78932(18) 0.08052(15) 0.05172(7) 0.0326(3) Uani 1 1 d . . . C1A C 0.9659(2) 0.18487(18) 0.01901(9) 0.0332(3) Uani 1 1 d . . . H1AA H 0.9470 0.3174 0.0315 0.040 Uiso 1 1 calc R . . C2A C 0.8238(2) -0.10533(18) 0.03273(9) 0.0336(3) Uani 1 1 d . . . H2AA H 0.7019 -0.1844 0.0551 0.040 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 O1 0.0379(5) 0.0437(5) 0.0636(6) -0.0319(5) 0.0184(4) -0.0179(4) O2 0.0387(5) 0.0396(5) 0.0637(6) -0.0192(4) 0.0179(4) -0.0165(4) C1 0.0288(6) 0.0310(6) 0.0340(6) -0.0096(4) 0.0013(4) -0.0074(4) C2 0.0288(6) 0.0314(6) 0.0400(6) -0.0124(5) 0.0053(5) -0.0083(5) C3 0.0288(6) 0.0306(6) 0.0387(6) -0.0117(5) 0.0024(5) -0.0076(4) C4 0.0323(6) 0.0324(6) 0.0394(6) -0.0128(5) 0.0060(5) -0.0093(5) C5 0.0334(6) 0.0316(6) 0.0378(6) -0.0114(5) 0.0041(5) -0.0090(5) C6 0.0380(7) 0.0355(6) 0.0427(7) -0.0138(5) 0.0087(5) -0.0071(5) C7 0.0521(8) 0.0387(7) 0.0513(8) -0.0198(6) 0.0069(6) -0.0044(6) N1A 0.0300(5) 0.0337(5) 0.0353(5) -0.0114(4) 0.0022(4) -0.0067(4) C1A 0.0350(6) 0.0285(5) 0.0386(6) -0.0115(5) 0.0004(5) -0.0087(5) C2A 0.0309(6) 0.0331(6) 0.0391(6) -0.0089(5) 0.0027(5) -0.0121(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 O1 C1 1.3276(14) . ? O1 H1 0.94(2) . ? O2 C1 1.2068(14) . ? C1 C2 1.5035(16) . ? C2 C3 1.5194(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5231(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5205(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5230(16) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5231(17) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N1A C1A 1.3319(16) . ? N1A C2A 1.3350(15) . ? C1A C2A 1.3846(17) 2_755 ? C1A H1AA 0.9500 . ? C2A C1A 1.3846(17) 2_755 ? C2A H2AA 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 C1 O1 H1 110.8(12) . . ? O2 C1 O1 122.87(11) . . ? O2 C1 C2 125.40(11) . . ? O1 C1 C2 111.72(10) . . ? C1 C2 C3 115.41(10) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 111.04(9) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 114.43(10) . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4B 108.7 . . ? C3 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 112.40(10) . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 113.71(11) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1A N1A C2A 117.10(10) . . ? N1A C1A C2A 121.78(11) . 2_755 ? N1A C1A H1AA 119.1 . . ? C2A C1A H1AA 119.1 2_755 . ? N1A C2A C1A 121.12(11) . 2_755 ? N1A C2A H2AA 119.4 . . ? C1A C2A H2AA 119.4 2_755 . ? 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 O2 C1 C2 C3 2.61(18) . . . . ? O1 C1 C2 C3 -177.97(10) . . . . ? C1 C2 C3 C4 177.14(10) . . . . ? C2 C3 C4 C5 -179.72(10) . . . . ? C3 C4 C5 C6 -175.59(11) . . . . ? C4 C5 C6 C7 179.26(11) . . . . ? C2A N1A C1A C2A 0.2(2) . . . 2_755 ? C1A N1A C2A C1A -0.18(19) . . . 2_755 ? #===END data_ab0211 _database_code_CSD 192856 _chemical_name_systematic ? _chemical_name_common 'pyrazine / octanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C8 H16 O2)' _chemical_formula_sum 'C20 H36 N2 O4' _chemical_formula_weight 368.51 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 5.4774(2) _cell_length_b 6.9086(3) _cell_length_c 15.2102(8) _cell_angle_alpha 81.541(2) _cell_angle_beta 84.977(2) _cell_angle_gamma 76.158(4) _cell_volume 551.95(4) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 3081 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 202 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm capillary at ca. 291 K ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4435 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.60 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.959 _reflns_number_total 2441 _reflns_number_gt 1939 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.1151P)^2^+0.4608P] 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 2441 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1083 _refine_ls_R_factor_gt 0.0882 _refine_ls_wR_factor_ref 0.2571 _refine_ls_wR_factor_gt 0.2405 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.276 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.068 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 O1 O -0.0741(4) -0.6337(3) 0.85963(14) 0.0466(6) Uani 1 1 d . . . H1 H 0.056(9) -0.707(7) 0.893(3) 0.079(13) Uiso 1 1 d . . . O2 O 0.1117(4) -0.3886(3) 0.87532(14) 0.0474(6) Uani 1 1 d . . . C1 C -0.0539(4) -0.4442(4) 0.84616(16) 0.0311(5) Uani 1 1 d . . . C2 C -0.2558(4) -0.3122(4) 0.79037(16) 0.0330(6) Uani 1 1 d . . . H2A H -0.4211 -0.3222 0.8202 0.040 Uiso 1 1 calc R . . H2B H -0.2449 -0.3646 0.7326 0.040 Uiso 1 1 calc R . . C3 C -0.2476(4) -0.0924(4) 0.77225(17) 0.0333(6) Uani 1 1 d . . . H3A H -0.0859 -0.0795 0.7401 0.040 Uiso 1 1 calc R . . H3B H -0.2564 -0.0383 0.8295 0.040 Uiso 1 1 calc R . . C4 C -0.4638(5) 0.0294(4) 0.71724(18) 0.0366(6) Uani 1 1 d . . . H4A H -0.6245 0.0118 0.7488 0.044 Uiso 1 1 calc R . . H4B H -0.4519 -0.0242 0.6597 0.044 Uiso 1 1 calc R . . C5 C -0.4691(5) 0.2529(4) 0.69890(17) 0.0352(6) Uani 1 1 d . . . H5A H -0.4952 0.3091 0.7561 0.042 Uiso 1 1 calc R . . H5B H -0.3036 0.2702 0.6716 0.042 Uiso 1 1 calc R . . C6 C -0.6731(5) 0.3706(4) 0.63796(17) 0.0362(6) Uani 1 1 d . . . H6A H -0.8388 0.3539 0.6654 0.043 Uiso 1 1 calc R . . H6B H -0.6476 0.3141 0.5808 0.043 Uiso 1 1 calc R . . C7 C -0.6769(5) 0.5939(4) 0.61947(19) 0.0412(6) Uani 1 1 d . . . H7A H -0.7088 0.6509 0.6765 0.049 Uiso 1 1 calc R . . H7B H -0.5087 0.6098 0.5945 0.049 Uiso 1 1 calc R . . C8 C -0.8724(6) 0.7128(5) 0.5560(2) 0.0552(8) Uani 1 1 d . . . H8A H -0.8385 0.6613 0.4984 0.083 Uiso 1 1 calc R . . H8B H -0.8656 0.8548 0.5480 0.083 Uiso 1 1 calc R . . H8C H -1.0401 0.6995 0.5804 0.083 Uiso 1 1 calc R . . N1A N 0.3005(4) -0.8826(3) 0.95326(14) 0.0338(5) Uani 1 1 d . . . C2A C 0.3317(4) -1.0812(4) 0.97026(17) 0.0347(6) Uani 1 1 d . . . H2AA H 0.2141 -1.1433 0.9498 0.042 Uiso 1 1 calc R . . C1A C 0.4690(5) -0.8016(4) 0.98313(17) 0.0346(6) Uani 1 1 d . . . H1AA H 0.4515 -0.6601 0.9721 0.041 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 O1 0.0419(11) 0.0280(10) 0.0707(14) 0.0103(8) -0.0267(9) -0.0110(8) O2 0.0437(11) 0.0327(10) 0.0682(13) -0.0013(8) -0.0263(9) -0.0084(8) C1 0.0279(11) 0.0281(12) 0.0362(12) -0.0012(9) -0.0043(9) -0.0050(9) C2 0.0305(12) 0.0255(12) 0.0414(13) -0.0002(9) -0.0097(9) -0.0032(9) C3 0.0294(12) 0.0262(12) 0.0428(13) -0.0007(9) -0.0080(9) -0.0038(9) C4 0.0339(13) 0.0278(12) 0.0468(14) -0.0015(10) -0.0119(10) -0.0033(9) C5 0.0331(12) 0.0289(12) 0.0426(13) 0.0008(10) -0.0093(10) -0.0059(9) C6 0.0328(12) 0.0316(13) 0.0420(14) 0.0006(10) -0.0101(10) -0.0036(10) C7 0.0406(14) 0.0315(14) 0.0473(15) 0.0039(10) -0.0106(11) -0.0027(10) C8 0.0526(17) 0.0452(17) 0.0567(18) 0.0104(13) -0.0158(13) 0.0050(13) N1A 0.0302(10) 0.0302(11) 0.0396(11) -0.0002(8) -0.0072(8) -0.0051(8) C2A 0.0294(12) 0.0340(13) 0.0422(13) -0.0042(10) -0.0063(9) -0.0093(9) C1A 0.0331(12) 0.0251(11) 0.0445(14) -0.0011(9) -0.0051(9) -0.0058(9) _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 O1 C1 1.325(3) . ? O1 H1 0.92(5) . ? O2 C1 1.206(3) . ? C1 C2 1.493(3) . ? C2 C3 1.513(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.517(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.522(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.515(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.523(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.510(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? N1A C1A 1.330(3) . ? N1A C2A 1.330(3) . ? C2A C1A 1.376(3) 2_637 ? C2A H2AA 0.9500 . ? C1A C2A 1.376(3) 2_637 ? C1A H1AA 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 C1 O1 H1 108(3) . . ? O2 C1 O1 122.9(2) . . ? O2 C1 C2 125.0(2) . . ? O1 C1 C2 112.1(2) . . ? C1 C2 C3 115.52(19) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 111.42(19) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C5 113.8(2) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C4 113.3(2) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C7 113.2(2) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 114.0(2) . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1A N1A C2A 117.5(2) . . ? N1A C2A C1A 121.3(2) . 2_637 ? N1A C2A H2AA 119.3 . . ? C1A C2A H2AA 119.3 2_637 . ? N1A C1A C2A 121.2(2) . 2_637 ? N1A C1A H1AA 119.4 . . ? C2A C1A H1AA 119.4 2_637 . ? 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 O2 C1 C2 C3 -1.3(4) . . . . ? O1 C1 C2 C3 179.6(2) . . . . ? C1 C2 C3 C4 -178.5(2) . . . . ? C2 C3 C4 C5 178.5(2) . . . . ? C3 C4 C5 C6 175.5(2) . . . . ? C4 C5 C6 C7 -179.7(2) . . . . ? C5 C6 C7 C8 177.8(2) . . . . ? C1A N1A C2A C1A -0.1(4) . . . 2_637 ? C2A N1A C1A C2A 0.1(4) . . . 2_637 ? #===END data_ab0212 _database_code_CSD 192857 _chemical_name_systematic ? _chemical_name_common 'pyrazine / nonanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C9 H18 O2)' _chemical_formula_sum 'C22 H40 N2 O4' _chemical_formula_weight 396.56 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 5.4731(2) _cell_length_b 6.8775(2) _cell_length_c 16.3824(6) _cell_angle_alpha 89.776(1) _cell_angle_beta 82.992(1) _cell_angle_gamma 76.091(1) _cell_volume 593.89(4) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 5100 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 218 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm glass capillary at ca. 300 K ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 6194 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 27.60 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.969 _reflns_number_total 2652 _reflns_number_gt 2221 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0638P)^2^+0.1622P] 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 2652 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1489 _refine_ls_wR_factor_gt 0.1391 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.251 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.037 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 O1 O -0.4479(2) 0.68345(15) 0.13075(7) 0.0466(3) Uani 1 1 d . . . H1 H -0.578(5) 0.748(3) 0.1001(14) 0.079(7) Uiso 1 1 d . . . O2 O -0.6328(2) 0.43227(15) 0.11629(7) 0.0468(3) Uani 1 1 d . . . C1 C -0.4719(2) 0.49741(18) 0.14293(8) 0.0303(3) Uani 1 1 d . . . C2 C -0.2778(2) 0.38372(18) 0.19442(8) 0.0319(3) Uani 1 1 d . . . H2A H -0.3008 0.4555 0.2481 0.038 Uiso 1 1 calc R . . H2B H -0.1068 0.3847 0.1668 0.038 Uiso 1 1 calc R . . C3 C -0.2878(2) 0.16738(18) 0.21008(8) 0.0318(3) Uani 1 1 d . . . H3A H -0.2634 0.0931 0.1569 0.038 Uiso 1 1 calc R . . H3B H -0.4567 0.1640 0.2388 0.038 Uiso 1 1 calc R . . C4 C -0.0827(3) 0.06629(19) 0.26222(9) 0.0349(3) Uani 1 1 d . . . H4A H -0.1081 0.1428 0.3149 0.042 Uiso 1 1 calc R . . H4B H 0.0848 0.0725 0.2332 0.042 Uiso 1 1 calc R . . C5 C -0.0788(3) -0.15198(19) 0.28085(9) 0.0345(3) Uani 1 1 d . . . H5A H -0.2484 -0.1600 0.3074 0.041 Uiso 1 1 calc R . . H5B H -0.0427 -0.2311 0.2285 0.041 Uiso 1 1 calc R . . C6 C 0.1191(3) -0.24309(19) 0.33689(9) 0.0351(3) Uani 1 1 d . . . H6A H 0.0835 -0.1620 0.3887 0.042 Uiso 1 1 calc R . . H6B H 0.2882 -0.2349 0.3099 0.042 Uiso 1 1 calc R . . C7 C 0.1280(3) -0.46059(19) 0.35781(8) 0.0345(3) Uani 1 1 d . . . H7A H -0.0431 -0.4706 0.3821 0.041 Uiso 1 1 calc R . . H7B H 0.1739 -0.5436 0.3065 0.041 Uiso 1 1 calc R . . C8 C 0.3170(3) -0.5441(2) 0.41762(10) 0.0423(4) Uani 1 1 d . . . H8A H 0.4879 -0.5340 0.3931 0.051 Uiso 1 1 calc R . . H8B H 0.2714 -0.4601 0.4687 0.051 Uiso 1 1 calc R . . C9 C 0.3282(4) -0.7608(2) 0.43965(11) 0.0535(4) Uani 1 1 d . . . H9A H 0.1595 -0.7727 0.4635 0.080 Uiso 1 1 calc R . . H9B H 0.4486 -0.8027 0.4797 0.080 Uiso 1 1 calc R . . H9C H 0.3837 -0.8465 0.3899 0.080 Uiso 1 1 calc R . . N1A N -0.8074(2) 0.89882(16) 0.04332(7) 0.0331(3) Uani 1 1 d . . . C1A C -0.9706(3) 0.80678(19) 0.01611(8) 0.0334(3) Uani 1 1 d . . . H1AA H -0.9547 0.6687 0.0267 0.040 Uiso 1 1 calc R . . C2A C -0.8366(2) 1.09317(19) 0.02735(8) 0.0337(3) Uani 1 1 d . . . H2AA H -0.7237 1.1638 0.0460 0.040 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 O1 0.0478(6) 0.0326(5) 0.0685(8) 0.0208(5) -0.0290(5) -0.0170(4) O2 0.0479(6) 0.0330(5) 0.0665(7) 0.0084(5) -0.0280(5) -0.0133(4) C1 0.0296(6) 0.0258(6) 0.0354(7) 0.0040(5) -0.0050(5) -0.0058(5) C2 0.0319(6) 0.0263(6) 0.0383(7) 0.0050(5) -0.0094(5) -0.0063(5) C3 0.0308(6) 0.0258(6) 0.0388(7) 0.0044(5) -0.0068(5) -0.0057(5) C4 0.0351(7) 0.0266(6) 0.0444(7) 0.0074(5) -0.0124(6) -0.0068(5) C5 0.0340(7) 0.0261(6) 0.0443(8) 0.0063(5) -0.0105(5) -0.0064(5) C6 0.0365(7) 0.0285(6) 0.0416(7) 0.0072(5) -0.0114(6) -0.0074(5) C7 0.0369(7) 0.0280(6) 0.0387(7) 0.0059(5) -0.0083(5) -0.0062(5) C8 0.0465(8) 0.0354(7) 0.0440(8) 0.0100(6) -0.0142(6) -0.0041(6) C9 0.0667(11) 0.0365(8) 0.0527(9) 0.0142(7) -0.0126(8) -0.0012(7) N1A 0.0315(6) 0.0297(6) 0.0376(6) 0.0044(4) -0.0067(4) -0.0056(4) C1A 0.0343(7) 0.0243(6) 0.0413(7) 0.0042(5) -0.0050(5) -0.0067(5) C2A 0.0324(6) 0.0295(6) 0.0408(7) 0.0007(5) -0.0067(5) -0.0096(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 O1 C1 1.3291(15) . ? O1 H1 0.95(3) . ? O2 C1 1.2045(16) . ? C1 C2 1.5054(17) . ? C2 C3 1.5216(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5256(17) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5263(16) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5233(18) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5240(17) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5223(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.521(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? N1A C1A 1.3298(18) . ? N1A C2A 1.3362(16) . ? C1A C2A 1.3873(19) 2_375 ? C1A H1AA 0.9500 . ? C2A C1A 1.3873(19) 2_375 ? C2A H2AA 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 C1 O1 H1 107.6(14) . . ? O2 C1 O1 123.09(12) . . ? O2 C1 C2 125.36(11) . . ? O1 C1 C2 111.54(11) . . ? C1 C2 C3 115.15(10) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 110.77(10) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C5 114.29(11) . . ? C3 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? C3 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 112.41(11) . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 114.23(11) . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 113.07(12) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 113.95(13) . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1A N1A C2A 117.26(11) . . ? N1A C1A C2A 121.83(12) . 2_375 ? N1A C1A H1AA 119.1 . . ? C2A C1A H1AA 119.1 2_375 . ? N1A C2A C1A 120.91(12) . 2_375 ? N1A C2A H2AA 119.5 . . ? C1A C2A H2AA 119.5 2_375 . ? 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 O2 C1 C2 C3 2.1(2) . . . . ? O1 C1 C2 C3 -178.83(11) . . . . ? C1 C2 C3 C4 179.65(11) . . . . ? C2 C3 C4 C5 -179.91(11) . . . . ? C3 C4 C5 C6 -176.83(11) . . . . ? C4 C5 C6 C7 179.45(11) . . . . ? C5 C6 C7 C8 -176.81(12) . . . . ? C6 C7 C8 C9 179.74(12) . . . . ? C2A N1A C1A C2A 0.2(2) . . . 2_375 ? C1A N1A C2A C1A -0.2(2) . . . 2_375 ? #===END data_ab0213 _database_code_CSD 192858 _chemical_name_systematic ? _chemical_name_common 'pyrazine / decanoic acid' _chemical_melting_point ? _chemical_formula_moiety 'C4 H4 N2, 2(C10 H20 O2)' _chemical_formula_sum 'C24 H44 N2 O4' _chemical_formula_weight 424.61 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 5.4573(2) _cell_length_b 6.8970(2) _cell_length_c 18.0387(6) _cell_angle_alpha 80.575(1) _cell_angle_beta 81.940(1) _cell_angle_gamma 75.554(2) _cell_volume 645.10(4) _cell_formula_units_Z 1 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6520 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 25.03 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_length 0.35 _exptl_crystal_size_rad 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 234 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ in 0.2 mm glass capillary at ca. 308 K ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 4697 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.88 _diffrn_reflns_theta_max 25.04 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.978 _reflns_number_total 2235 _reflns_number_gt 1988 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor, 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor, 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'SHELXTL v6.12 (Bruker AXS, 2001)' _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^)+(0.0573P)^2^+0.1626P] 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 2235 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.149 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.031 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 O1 O 0.3530(2) -0.71362(16) 0.61993(7) 0.0466(3) Uani 1 1 d . . . H1 H 0.508(5) -0.773(3) 0.5902(13) 0.078(7) Uiso 1 1 d . . . O2 O 0.5492(2) -0.46153(16) 0.60666(7) 0.0468(3) Uani 1 1 d . . . C1 C 0.3682(3) -0.5322(2) 0.63133(7) 0.0306(3) Uani 1 1 d . . . C2 C 0.1379(3) -0.4308(2) 0.67880(8) 0.0321(3) Uani 1 1 d . . . H2A H 0.1237 -0.5168 0.7281 0.039 Uiso 1 1 calc R . . H2B H -0.0149 -0.4233 0.6537 0.039 Uiso 1 1 calc R . . C3 C 0.1366(3) -0.2196(2) 0.69323(8) 0.0322(3) Uani 1 1 d . . . H3A H 0.1491 -0.1313 0.6444 0.039 Uiso 1 1 calc R . . H3B H 0.2865 -0.2250 0.7194 0.039 Uiso 1 1 calc R . . C4 C -0.1049(3) -0.1306(2) 0.74125(8) 0.0351(4) Uani 1 1 d . . . H4A H -0.2532 -0.1260 0.7145 0.042 Uiso 1 1 calc R . . H4B H -0.1174 -0.2219 0.7894 0.042 Uiso 1 1 calc R . . C5 C -0.1200(3) 0.0802(2) 0.75919(8) 0.0363(4) Uani 1 1 d . . . H5A H -0.1186 0.1739 0.7114 0.044 Uiso 1 1 calc R . . H5B H 0.0328 0.0779 0.7834 0.044 Uiso 1 1 calc R . . C6 C -0.3565(3) 0.1604(2) 0.81104(8) 0.0366(4) Uani 1 1 d . . . H6A H -0.5092 0.1618 0.7869 0.044 Uiso 1 1 calc R . . H6B H -0.3573 0.0669 0.8589 0.044 Uiso 1 1 calc R . . C7 C -0.3737(3) 0.3718(2) 0.82895(8) 0.0354(4) Uani 1 1 d . . . H7A H -0.3781 0.4657 0.7811 0.042 Uiso 1 1 calc R . . H7B H -0.2179 0.3711 0.8514 0.042 Uiso 1 1 calc R . . C8 C -0.6044(3) 0.4522(2) 0.88274(8) 0.0378(4) Uani 1 1 d . . . H8A H -0.7609 0.4557 0.8601 0.045 Uiso 1 1 calc R . . H8B H -0.6018 0.3582 0.9305 0.045 Uiso 1 1 calc R . . C9 C -0.6140(3) 0.6622(2) 0.90027(9) 0.0442(4) Uani 1 1 d . . . H9A H -0.4587 0.6576 0.9236 0.053 Uiso 1 1 calc R . . H9B H -0.6125 0.7551 0.8522 0.053 Uiso 1 1 calc R . . C10 C -0.8451(4) 0.7475(3) 0.95259(11) 0.0615(5) Uani 1 1 d . . . H10A H -1.0002 0.7571 0.9293 0.092 Uiso 1 1 calc R . . H10B H -0.8376 0.8822 0.9615 0.092 Uiso 1 1 calc R . . H10C H -0.8468 0.6583 1.0008 0.092 Uiso 1 1 calc R . . N1A N 0.7759(2) -0.90937(17) 0.53984(6) 0.0334(3) Uani 1 1 d . . . C1A C 0.9588(3) -0.8113(2) 0.51458(8) 0.0336(3) Uani 1 1 d . . . H1AA H 0.9351 -0.6761 0.5242 0.040 Uiso 1 1 calc R . . C2A C 0.8174(3) -1.0990(2) 0.52531(8) 0.0340(3) Uani 1 1 d . . . H2AA H 0.6912 -1.1737 0.5426 0.041 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 O1 0.0362(6) 0.0391(6) 0.0690(8) -0.0283(5) 0.0149(5) -0.0148(5) O2 0.0359(6) 0.0362(6) 0.0681(8) -0.0161(5) 0.0141(5) -0.0127(5) C1 0.0280(7) 0.0290(7) 0.0353(7) -0.0067(5) -0.0030(5) -0.0062(6) C2 0.0284(7) 0.0294(7) 0.0375(7) -0.0077(6) 0.0012(6) -0.0055(6) C3 0.0284(7) 0.0292(7) 0.0392(8) -0.0081(6) -0.0012(6) -0.0063(6) C4 0.0313(7) 0.0303(8) 0.0432(8) -0.0103(6) 0.0023(6) -0.0064(6) C5 0.0317(7) 0.0300(8) 0.0465(8) -0.0108(6) 0.0012(6) -0.0052(6) C6 0.0332(8) 0.0306(8) 0.0452(8) -0.0101(6) 0.0024(6) -0.0064(6) C7 0.0329(7) 0.0327(8) 0.0405(8) -0.0107(6) 0.0016(6) -0.0071(6) C8 0.0342(8) 0.0380(8) 0.0403(8) -0.0116(6) 0.0015(6) -0.0056(6) C9 0.0445(9) 0.0393(9) 0.0477(9) -0.0173(7) 0.0005(7) -0.0030(7) C10 0.0580(11) 0.0579(11) 0.0615(11) -0.0282(9) 0.0039(9) 0.0072(9) N1A 0.0281(6) 0.0325(7) 0.0389(7) -0.0085(5) -0.0009(5) -0.0051(5) C1A 0.0338(7) 0.0264(7) 0.0417(8) -0.0087(6) -0.0038(6) -0.0064(6) C2A 0.0295(7) 0.0311(7) 0.0418(8) -0.0054(6) -0.0004(6) -0.0092(6) _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 O1 C1 1.3254(17) . ? O1 H1 0.97(3) . ? O2 C1 1.2068(17) . ? C1 C2 1.5023(18) . ? C2 C3 1.5194(18) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5211(18) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5210(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5234(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.5224(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5229(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.519(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.518(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? N1A C1A 1.3303(19) . ? N1A C2A 1.3333(18) . ? C1A C2A 1.384(2) 2_736 ? C1A H1AA 0.9500 . ? C2A C1A 1.384(2) 2_736 ? C2A H2AA 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 C1 O1 H1 108.2(14) . . ? O2 C1 O1 122.83(13) . . ? O2 C1 C2 125.32(12) . . ? O1 C1 C2 111.85(11) . . ? C1 C2 C3 115.41(11) . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 C4 111.12(11) . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 114.51(11) . . ? C5 C4 H4A 108.6 . . ? C3 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C3 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C4 C5 C6 113.29(12) . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 113.61(12) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 C8 114.48(12) . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 C8 C7 113.15(12) . . ? C9 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? C9 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 114.18(14) . . ? C10 C9 H9A 108.7 . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? C8 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1A N1A C2A 117.14(12) . . ? N1A C1A C2A 121.72(13) . 2_736 ? N1A C1A H1AA 119.1 . . ? C2A C1A H1AA 119.1 2_736 . ? N1A C2A C1A 121.14(13) . 2_736 ? N1A C2A H2AA 119.4 . . ? C1A C2A H2AA 119.4 2_736 . ? 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 O2 C1 C2 C3 2.2(2) . . . . ? O1 C1 C2 C3 -178.66(11) . . . . ? C1 C2 C3 C4 179.64(11) . . . . ? C2 C3 C4 C5 179.28(11) . . . . ? C3 C4 C5 C6 -176.68(12) . . . . ? C4 C5 C6 C7 -179.70(12) . . . . ? C5 C6 C7 C8 -178.14(12) . . . . ? C6 C7 C8 C9 179.21(12) . . . . ? C7 C8 C9 C10 178.86(13) . . . . ? C2A N1A C1A C2A 0.2(2) . . . 2_736 ? C1A N1A C2A C1A -0.2(2) . . . 2_736 ? #===END