# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 # CCDC Number: 440/246 data_(1) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-dimethylbarbituric acid ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H8 N2 O3' _chemical_formula_weight 156.14 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 'orthorhombic' _symmetry_space_group_name_H-M 'F d d 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+1/4, -y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+1/4, -y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+3/4, -y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' _cell_length_a 15.642(3) _cell_length_b 29.006(6) _cell_length_c 6.5560(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2974.5(9) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1708 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 27.83 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1708 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 27.83 _reflns_number_total 957 _reflns_number_gt 628 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'Kappa CCD server software (Nonius, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (C.K. Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997); PARST (Nardelli, 1983, 1995) ; _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^)+(0.0709P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0051(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 957 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.34443(14) 0.17842(9) 0.4865(6) 0.0993(9) Uani 1 1 d . . . O2 O 0.64331(13) 0.16451(8) 0.4796(6) 0.0935(9) Uani 1 1 d . . . O3 O 0.49938(12) 0.22113(8) -0.0580 0.0853(8) Uani 1 1 d . . . N1 N 0.42045(12) 0.19609(7) 0.2051(5) 0.0612(7) Uani 1 1 d . . . N2 N 0.57148(13) 0.18856(7) 0.2021(5) 0.0583(6) Uani 1 1 d . . . C1 C 0.41323(16) 0.18015(9) 0.4021(6) 0.0633(8) Uani 1 1 d . . . C2 C 0.49270(17) 0.16483(13) 0.5043(6) 0.0681(8) Uani 1 1 d . . . H21 H 0.4984(16) 0.1776(11) 0.634(8) 0.081(10) Uiso 1 1 d . . . H22 H 0.4861(15) 0.1315(15) 0.528(6) 0.097(12) Uiso 1 1 d . . . C3 C 0.57522(16) 0.17251(8) 0.3979(5) 0.0599(8) Uani 1 1 d . . . C4 C 0.49722(15) 0.20284(9) 0.1067(6) 0.0568(7) Uani 1 1 d . . . C5 C 0.34280(18) 0.21019(13) 0.0968(8) 0.1005(13) Uani 1 1 d . . . H51 H 0.2940 0.1956 0.1578 0.121 Uiso 1 1 calc R . . H52 H 0.3469 0.2012 -0.0437 0.121 Uiso 1 1 calc R . . H53 H 0.3365 0.2431 0.1055 0.121 Uiso 1 1 calc R . . C6 C 0.65163(19) 0.19580(13) 0.0899(7) 0.0929(12) Uani 1 1 d . . . H61 H 0.6445 0.1860 -0.0490 0.111 Uiso 1 1 calc R . . H62 H 0.6965 0.1782 0.1525 0.111 Uiso 1 1 calc R . . H63 H 0.6663 0.2279 0.0929 0.111 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 0.0609(14) 0.1205(18) 0.117(2) -0.0082(18) 0.0330(14) -0.0051(11) O2 0.0598(13) 0.1095(17) 0.111(2) 0.0307(17) -0.0237(13) -0.0005(11) O3 0.0970(16) 0.0994(15) 0.0597(14) 0.0130(13) -0.0064(11) -0.0044(11) N1 0.0434(12) 0.0647(12) 0.0754(17) 0.0032(14) -0.0072(11) -0.0008(8) N2 0.0441(12) 0.0686(12) 0.0621(14) 0.0011(12) 0.0093(10) 0.0052(9) C1 0.0502(15) 0.0662(15) 0.073(2) -0.0082(15) 0.0132(14) -0.0031(11) C2 0.0655(19) 0.080(2) 0.0589(18) 0.0068(17) 0.0058(15) -0.0057(14) C3 0.0487(14) 0.0608(14) 0.070(2) 0.0032(14) -0.0020(13) -0.0013(11) C4 0.0588(17) 0.0603(14) 0.0513(16) -0.0014(15) -0.0040(13) -0.0026(11) C5 0.0561(19) 0.104(2) 0.141(4) 0.025(3) -0.026(2) -0.0009(17) C6 0.0591(19) 0.114(3) 0.106(3) 0.010(2) 0.0314(18) 0.0055(17) _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 1.211(3) . ? O2 C3 1.215(3) . ? O3 C4 1.204(4) . ? N1 C1 1.376(4) . ? N1 C4 1.377(3) . ? N1 C5 1.465(4) . ? N2 C3 1.366(4) . ? N2 C4 1.383(3) . ? N2 C6 1.469(3) . ? C1 C2 1.481(4) . ? C2 C3 1.484(4) . ? C2 H21 0.93(5) . ? C2 H22 0.98(4) . ? C5 H51 0.9600 . ? C5 H52 0.9600 . ? C5 H53 0.9600 . ? C6 H61 0.9600 . ? C6 H62 0.9600 . ? C6 H63 0.9600 . ? 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 N1 C4 124.0(2) . . ? C1 N1 C5 118.7(3) . . ? C4 N1 C5 117.2(3) . . ? C3 N2 C4 124.2(2) . . ? C3 N2 C6 118.9(3) . . ? C4 N2 C6 116.6(3) . . ? O1 C1 N1 121.0(3) . . ? O1 C1 C2 121.8(3) . . ? N1 C1 C2 117.2(2) . . ? C1 C2 C3 118.2(3) . . ? C1 C2 H21 112.0(18) . . ? C3 C2 H21 106.7(17) . . ? C1 C2 H22 106.0(16) . . ? C3 C2 H22 108.2(16) . . ? H21 C2 H22 105(3) . . ? O2 C3 N2 121.1(3) . . ? O2 C3 C2 121.7(3) . . ? N2 C3 C2 117.1(2) . . ? O3 C4 N1 120.5(2) . . ? O3 C4 N2 120.9(2) . . ? N1 C4 N2 118.6(2) . . ? N1 C5 H51 109.5 . . ? N1 C5 H52 109.5 . . ? H51 C5 H52 109.5 . . ? N1 C5 H53 109.5 . . ? H51 C5 H53 109.5 . . ? H52 C5 H53 109.5 . . ? N2 C6 H61 109.5 . . ? N2 C6 H62 109.5 . . ? H61 C6 H62 109.5 . . ? N2 C6 H63 109.5 . . ? H61 C6 H63 109.5 . . ? H62 C6 H63 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.83 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.163 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.035 #===END data_(2) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-dimethylbarbituric acid . o-nitrophenylhydrazine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 N5 O5' _chemical_formula_weight 309.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _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 8.181(2) _cell_length_b 12.891(2) _cell_length_c 7.758(2) _cell_angle_alpha 104.73(2) _cell_angle_beta 116.10(2) _cell_angle_gamma 73.34(2) _cell_volume 696.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 14 _exptl_crystal_description 'irregular' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.476 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3241 _diffrn_reflns_av_R_equivalents 0.013 _diffrn_reflns_av_sigmaI/netI 0.0333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 26.98 _reflns_number_total 3026 _reflns_number_gt 1947 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, C.K. Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1983, 1995) ; _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^)+(0.0784P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3026 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1345 _refine_ls_wR_factor_gt 0.1215 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.004 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 0.2781(2) 0.54740(14) 0.3405(3) 0.0796(5) Uani 1 1 d . . . O2 O 0.7991(2) 0.64795(14) 0.3842(3) 0.0713(5) Uani 1 1 d . . . O3 O 0.3919(2) 0.88430(13) 0.6129(2) 0.0666(4) Uani 1 1 d . . . N1 N 0.3345(2) 0.71460(13) 0.4789(2) 0.0457(4) Uani 1 1 d . . . N2 N 0.5924(2) 0.76984(13) 0.4906(2) 0.0444(4) Uani 1 1 d . . . C1 C 0.3689(3) 0.61484(17) 0.3753(3) 0.0500(5) Uani 1 1 d . . . C2 C 0.5178(3) 0.59508(19) 0.3029(4) 0.0552(5) Uani 1 1 d . . . C3 C 0.6504(3) 0.67064(16) 0.3963(3) 0.0472(5) Uani 1 1 d . . . C4 C 0.4360(2) 0.79576(16) 0.5313(3) 0.0437(4) Uani 1 1 d . . . C5 C 0.1777(4) 0.7418(3) 0.5384(5) 0.0673(7) Uani 1 1 d . . . C6 C 0.7044(4) 0.8543(2) 0.5577(4) 0.0609(6) Uani 1 1 d . . . O4 O 0.5048(2) 0.19205(16) -0.0609(3) 0.0771(5) Uani 1 1 d . . . O5 O 0.4009(2) 0.34162(15) 0.0905(3) 0.0713(5) Uani 1 1 d . . . N3 N 0.0813(3) 0.37355(15) 0.1142(3) 0.0556(5) Uani 1 1 d . . . N4 N -0.0704(3) 0.42941(19) 0.1649(4) 0.0674(6) Uani 1 1 d . . . N5 N 0.3865(2) 0.24842(16) -0.0004(2) 0.0545(4) Uani 1 1 d . . . C7 C 0.0836(2) 0.27006(15) 0.0205(3) 0.0419(4) Uani 1 1 d . . . C8 C 0.2291(3) 0.20606(16) -0.0355(3) 0.0458(4) Uani 1 1 d . . . C9 C 0.2256(4) 0.09852(18) -0.1287(3) 0.0606(6) Uani 1 1 d . . . C10 C 0.0791(4) 0.0533(2) -0.1718(4) 0.0726(7) Uani 1 1 d . . . C11 C -0.0664(4) 0.11419(18) -0.1210(3) 0.0622(6) Uani 1 1 d . . . C12 C -0.0654(3) 0.21847(18) -0.0275(3) 0.0502(5) Uani 1 1 d . . . H21 H 0.578(3) 0.521(2) 0.303(3) 0.061(6) Uiso 1 1 d . . . H22 H 0.454(4) 0.604(2) 0.163(5) 0.096(9) Uiso 1 1 d . . . H30 H 0.175(4) 0.399(2) 0.153(4) 0.067(7) Uiso 1 1 d . . . H410 H -0.113(5) 0.488(3) 0.124(5) 0.115(13) Uiso 1 1 d . . . H420 H -0.031(5) 0.441(3) 0.293(5) 0.103(11) Uiso 1 1 d . . . H51 H 0.083(6) 0.798(4) 0.486(6) 0.141(15) Uiso 1 1 d . . . H52 H 0.219(5) 0.740(3) 0.676(6) 0.124(12) Uiso 1 1 d . . . H53 H 0.133(8) 0.678(5) 0.493(9) 0.21(2) Uiso 1 1 d . . . H61 H 0.669(5) 0.899(3) 0.471(5) 0.120(12) Uiso 1 1 d . . . H62 H 0.718(6) 0.887(3) 0.685(6) 0.142(14) Uiso 1 1 d . . . H63 H 0.827(6) 0.823(3) 0.612(5) 0.127(13) Uiso 1 1 d . . . H9 H 0.325(3) 0.058(2) -0.164(3) 0.067(7) Uiso 1 1 d . . . H10 H 0.078(4) -0.016(2) -0.231(4) 0.086(8) Uiso 1 1 d . . . H11 H -0.172(4) 0.089(2) -0.148(4) 0.077(8) Uiso 1 1 d . . . H12 H -0.163(3) 0.2615(19) 0.004(3) 0.061(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0767(11) 0.0714(11) 0.1067(14) -0.0162(9) 0.0493(10) -0.0430(9) O2 0.0503(8) 0.0755(11) 0.0982(12) -0.0016(9) 0.0471(9) -0.0113(7) O3 0.0667(10) 0.0576(9) 0.0826(11) -0.0164(8) 0.0470(9) -0.0176(7) N1 0.0360(8) 0.0572(10) 0.0502(9) 0.0015(7) 0.0228(7) -0.0146(7) N2 0.0394(8) 0.0506(9) 0.0502(9) 0.0035(7) 0.0225(7) -0.0148(7) C1 0.0432(10) 0.0522(12) 0.0564(12) -0.0014(9) 0.0220(9) -0.0170(9) C2 0.0576(12) 0.0443(12) 0.0718(15) -0.0030(10) 0.0388(12) -0.0107(10) C3 0.0430(10) 0.0510(11) 0.0544(11) 0.0067(9) 0.0276(9) -0.0067(8) C4 0.0415(9) 0.0470(11) 0.0434(10) 0.0007(8) 0.0198(8) -0.0108(8) C5 0.0470(12) 0.0880(19) 0.0813(18) 0.0014(15) 0.0406(13) -0.0195(13) C6 0.0613(14) 0.0642(15) 0.0684(16) 0.0012(12) 0.0278(12) -0.0330(12) O4 0.0600(9) 0.0971(13) 0.0867(12) 0.0101(10) 0.0492(9) -0.0044(9) O5 0.0619(9) 0.0761(11) 0.0860(11) -0.0118(9) 0.0407(9) -0.0308(8) N3 0.0482(10) 0.0493(10) 0.0744(12) -0.0069(8) 0.0343(9) -0.0148(8) N4 0.0573(12) 0.0575(13) 0.0924(17) -0.0035(12) 0.0450(12) -0.0068(10) N5 0.0482(9) 0.0688(12) 0.0535(10) 0.0116(9) 0.0262(8) -0.0098(8) C7 0.0417(9) 0.0436(10) 0.0432(10) 0.0078(8) 0.0191(8) -0.0080(8) C8 0.0477(10) 0.0500(11) 0.0447(10) 0.0081(8) 0.0234(8) -0.0077(8) C9 0.0752(15) 0.0516(13) 0.0643(14) 0.0017(10) 0.0418(12) -0.0094(11) C10 0.100(2) 0.0452(13) 0.0801(17) -0.0056(12) 0.0463(15) -0.0214(13) C11 0.0745(15) 0.0535(13) 0.0664(14) 0.0050(11) 0.0277(12) -0.0281(12) C12 0.0475(11) 0.0523(12) 0.0563(12) 0.0109(10) 0.0218(10) -0.0135(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 1.206(2) . ? O2 C3 1.208(2) . ? O3 C4 1.196(2) . ? N1 C1 1.358(3) . ? N1 C4 1.391(2) . ? N1 C5 1.470(3) . ? N2 C3 1.370(2) . ? N2 C4 1.381(2) . ? N2 C6 1.469(3) . ? C1 C2 1.488(3) . ? C2 C3 1.485(3) . ? C2 H21 0.94(2) . ? C2 H22 1.00(3) . ? C5 H51 0.91(4) . ? C5 H52 0.97(4) . ? C5 H53 0.92(6) . ? C6 H61 0.89(3) . ? C6 H62 0.94(4) . ? C6 H63 0.91(4) . ? O4 N5 1.228(2) . ? O5 N5 1.238(2) . ? N3 C7 1.347(3) . ? N3 N4 1.409(3) . ? N3 H30 0.82(3) . ? N4 H410 0.82(3) . ? N4 H420 0.88(3) . ? N5 C8 1.432(3) . ? C7 C8 1.412(3) . ? C7 C12 1.417(3) . ? C8 C9 1.393(3) . ? C9 C10 1.355(4) . ? C9 H9 0.95(3) . ? C10 C11 1.381(4) . ? C10 H10 0.90(3) . ? C11 C12 1.356(3) . ? C11 H11 0.93(3) . ? C12 H12 0.92(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 124.52(15) . . ? C1 N1 C5 119.04(18) . . ? C4 N1 C5 116.43(18) . . ? C3 N2 C4 124.19(16) . . ? C3 N2 C6 118.80(17) . . ? C4 N2 C6 116.99(18) . . ? O1 C1 N1 120.64(19) . . ? O1 C1 C2 122.4(2) . . ? N1 C1 C2 116.95(17) . . ? C3 C2 C1 116.69(19) . . ? C3 C2 H21 112.5(14) . . ? C1 C2 H21 109.3(14) . . ? C3 C2 H22 106.0(16) . . ? C1 C2 H22 106.9(15) . . ? H21 C2 H22 105(2) . . ? O2 C3 N2 121.31(19) . . ? O2 C3 C2 121.99(19) . . ? N2 C3 C2 116.64(16) . . ? O3 C4 N2 121.02(18) . . ? O3 C4 N1 121.20(17) . . ? N2 C4 N1 117.75(16) . . ? N1 C5 H51 117(3) . . ? N1 C5 H52 112(2) . . ? H51 C5 H52 117(3) . . ? N1 C5 H53 102(4) . . ? H51 C5 H53 108(4) . . ? H52 C5 H53 98(4) . . ? N2 C6 H61 113(2) . . ? N2 C6 H62 110(2) . . ? H61 C6 H62 117(3) . . ? N2 C6 H63 109(2) . . ? H61 C6 H63 119(3) . . ? H62 C6 H63 85(3) . . ? C7 N3 N4 119.18(18) . . ? C7 N3 H30 118.6(18) . . ? N4 N3 H30 121.6(18) . . ? N3 N4 H410 109(2) . . ? N3 N4 H420 109(2) . . ? H410 N4 H420 109(3) . . ? O4 N5 O5 121.03(19) . . ? O4 N5 C8 119.67(19) . . ? O5 N5 C8 119.31(16) . . ? N3 C7 C8 124.00(18) . . ? N3 C7 C12 120.27(18) . . ? C8 C7 C12 115.73(18) . . ? C9 C8 C7 121.42(19) . . ? C9 C8 N5 116.76(18) . . ? C7 C8 N5 121.82(18) . . ? C10 C9 C8 120.4(2) . . ? C10 C9 H9 120.0(15) . . ? C8 C9 H9 119.6(15) . . ? C9 C10 C11 119.6(2) . . ? C9 C10 H10 120.2(18) . . ? C11 C10 H10 120.2(18) . . ? C12 C11 C10 121.3(2) . . ? C12 C11 H11 114.2(17) . . ? C10 C11 H11 124.5(17) . . ? C11 C12 C7 121.5(2) . . ? C11 C12 H12 122.9(15) . . ? C7 C12 H12 115.5(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.229 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.046 #===END data_(3) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-Dimethyibarbituric acid . p-nitroaniline ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 N4 O5' _chemical_formula_weight 294.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21 / 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 7.586(2) _cell_length_b 16.547(2) _cell_length_c 10.856(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.10(2) _cell_angle_gamma 90.00 _cell_volume 1352.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 13 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'red' _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3102 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26.99 _reflns_number_total 2943 _reflns_number_gt 1759 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4, Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4, Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, C.K. Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1983, 1985) ; _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^)+(0.0751P)^2^+0.0920P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2943 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1469 _refine_ls_wR_factor_gt 0.1301 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.005 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 -0.1955(3) 0.24075(12) -0.51403(17) 0.0874(6) Uani 1 1 d . . . O2 O -0.0949(3) 0.50077(10) -0.35680(17) 0.0796(6) Uani 1 1 d . . . O3 O 0.1314(2) 0.28283(11) -0.14507(16) 0.0782(6) Uani 1 1 d . . . N1 N -0.0303(2) 0.26034(10) -0.32984(16) 0.0528(5) Uani 1 1 d . . . N2 N 0.0153(2) 0.39228(10) -0.24810(15) 0.0507(4) Uani 1 1 d . . . C1 C -0.1239(3) 0.28724(13) -0.4382(2) 0.0538(6) Uani 1 1 d . . . C2 C -0.1298(4) 0.37502(15) -0.4585(2) 0.0587(6) Uani 1 1 d . . . C3 C -0.0713(3) 0.42886(13) -0.3525(2) 0.0524(5) Uani 1 1 d . . . C4 C 0.0444(3) 0.31018(13) -0.23617(19) 0.0506(5) Uani 1 1 d . . . C5 C -0.0153(6) 0.17269(16) -0.3086(4) 0.0823(9) Uani 1 1 d . . . C6 C 0.0792(5) 0.4435(2) -0.1414(3) 0.0824(9) Uani 1 1 d . . . O4 O 0.4621(3) -0.07589(11) 0.2220(2) 0.1060(7) Uani 1 1 d . . . O5 O 0.6274(3) -0.02321(12) 0.3772(2) 0.1025(7) Uani 1 1 d . . . N3 N 0.3974(3) 0.28824(13) 0.0771(2) 0.0676(6) Uani 1 1 d . . . N4 N 0.5311(3) -0.01658(12) 0.2778(2) 0.0749(6) Uani 1 1 d . . . C7 C 0.4323(3) 0.21424(12) 0.12459(19) 0.0491(5) Uani 1 1 d . . . C8 C 0.3705(3) 0.14455(13) 0.0591(2) 0.0545(6) Uani 1 1 d . . . C9 C 0.4023(3) 0.06996(14) 0.1088(2) 0.0578(6) Uani 1 1 d . . . C10 C 0.4993(3) 0.06201(12) 0.2249(2) 0.0540(5) Uani 1 1 d . . . C11 C 0.5638(3) 0.12951(14) 0.2909(2) 0.0552(6) Uani 1 1 d . . . C12 C 0.5318(3) 0.20434(12) 0.2412(2) 0.0525(5) Uani 1 1 d . . . H21 H -0.058(3) 0.3876(15) -0.519(2) 0.076(8) Uiso 1 1 d . . . H22 H -0.241(4) 0.3886(18) -0.498(3) 0.092(9) Uiso 1 1 d . . . H31 H 0.337(4) 0.2910(16) 0.011(3) 0.081(9) Uiso 1 1 d . . . H32 H 0.441(4) 0.330(2) 0.123(3) 0.094(10) Uiso 1 1 d . . . H51 H -0.091(6) 0.158(3) -0.267(4) 0.155(19) Uiso 1 1 d . . . H52 H -0.020(6) 0.144(3) -0.382(4) 0.170(18) Uiso 1 1 d . . . H53 H 0.095(7) 0.160(3) -0.265(5) 0.19(2) Uiso 1 1 d . . . H61 H 0.175(6) 0.426(3) -0.104(4) 0.143(16) Uiso 1 1 d . . . H62 H 0.004(6) 0.465(3) -0.106(5) 0.20(2) Uiso 1 1 d . . . H63 H 0.135(9) 0.495(4) -0.184(6) 0.26(3) Uiso 1 1 d . . . H8 H 0.315(3) 0.1463(14) -0.021(2) 0.067(7) Uiso 1 1 d . . . H9 H 0.352(3) 0.0244(18) 0.066(3) 0.088(8) Uiso 1 1 d . . . H11 H 0.624(3) 0.1233(14) 0.367(2) 0.064(7) Uiso 1 1 d . . . H12 H 0.574(3) 0.2501(15) 0.287(2) 0.053(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0941(13) 0.0808(13) 0.0804(12) -0.0275(10) -0.0174(10) -0.0100(10) O2 0.1048(14) 0.0433(9) 0.0905(13) 0.0080(8) 0.0106(10) 0.0042(9) O3 0.0850(12) 0.0819(13) 0.0617(10) 0.0128(8) -0.0154(9) 0.0130(9) N1 0.0603(11) 0.0394(9) 0.0578(10) 0.0017(8) 0.0041(9) 0.0004(8) N2 0.0546(10) 0.0465(10) 0.0490(9) -0.0050(8) -0.0009(7) -0.0018(8) C1 0.0501(12) 0.0581(13) 0.0515(12) -0.0078(10) -0.0009(10) -0.0021(10) C2 0.0624(15) 0.0611(14) 0.0491(13) 0.0072(10) -0.0074(11) 0.0010(11) C3 0.0559(12) 0.0449(12) 0.0567(13) 0.0048(9) 0.0077(10) -0.0016(9) C4 0.0474(12) 0.0559(12) 0.0472(11) 0.0049(10) 0.0006(9) 0.0026(9) C5 0.112(3) 0.0418(15) 0.094(2) 0.0076(14) 0.015(2) 0.0052(15) C6 0.089(2) 0.085(2) 0.0689(18) -0.0301(16) -0.0066(16) -0.0085(18) O4 0.1325(19) 0.0451(11) 0.1333(18) 0.0038(11) -0.0123(14) -0.0116(11) O5 0.1348(19) 0.0724(13) 0.0920(14) 0.0273(11) -0.0185(13) 0.0118(12) N3 0.0807(15) 0.0471(12) 0.0696(14) 0.0018(10) -0.0128(12) 0.0055(10) N4 0.0849(15) 0.0514(13) 0.0868(16) 0.0090(11) 0.0043(12) 0.0046(11) C7 0.0454(11) 0.0463(12) 0.0539(12) -0.0035(9) -0.0014(9) 0.0023(8) C8 0.0534(12) 0.0549(14) 0.0514(12) -0.0083(10) -0.0083(10) 0.0015(9) C9 0.0594(13) 0.0448(12) 0.0658(14) -0.0110(10) -0.0051(11) -0.0041(10) C10 0.0561(12) 0.0423(11) 0.0622(13) 0.0012(9) 0.0013(10) 0.0020(9) C11 0.0586(13) 0.0550(13) 0.0484(12) -0.0028(10) -0.0079(10) 0.0024(10) C12 0.0547(12) 0.0427(12) 0.0561(12) -0.0101(9) -0.0087(10) -0.0015(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 1.206(3) . ? O2 C3 1.203(3) . ? O3 C4 1.207(2) . ? N1 C1 1.371(3) . ? N1 C4 1.376(3) . ? N1 C5 1.471(3) . ? N2 C3 1.378(3) . ? N2 C4 1.380(3) . ? N2 C6 1.468(3) . ? C1 C2 1.469(3) . ? C2 C3 1.480(3) . ? C2 H21 0.93(3) . ? C2 H22 0.93(3) . ? C5 H51 0.81(4) . ? C5 H52 0.92(5) . ? C5 H53 0.93(6) . ? C6 H61 0.84(4) . ? C6 H62 0.81(5) . ? C6 H63 1.09(7) . ? O4 N4 1.235(3) . ? O5 N4 1.231(3) . ? N3 C7 1.342(3) . ? N3 H31 0.81(3) . ? N3 H32 0.89(3) . ? N4 C10 1.430(3) . ? C7 C12 1.401(3) . ? C7 C8 1.404(3) . ? C8 C9 1.356(3) . ? C8 H8 0.92(2) . ? C9 C10 1.386(3) . ? C9 H9 0.94(3) . ? C10 C11 1.384(3) . ? C11 C12 1.361(3) . ? C11 H11 0.90(2) . ? C12 H12 0.94(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 124.19(18) . . ? C1 N1 C5 118.5(2) . . ? C4 N1 C5 117.3(2) . . ? C3 N2 C4 124.36(17) . . ? C3 N2 C6 118.2(2) . . ? C4 N2 C6 117.4(2) . . ? O1 C1 N1 121.4(2) . . ? O1 C1 C2 121.7(2) . . ? N1 C1 C2 116.93(18) . . ? C1 C2 C3 118.53(19) . . ? C1 C2 H21 108.6(16) . . ? C3 C2 H21 105.7(15) . . ? C1 C2 H22 108.6(18) . . ? C3 C2 H22 112.6(18) . . ? H21 C2 H22 101(2) . . ? O2 C3 N2 121.4(2) . . ? O2 C3 C2 122.4(2) . . ? N2 C3 C2 116.24(19) . . ? O3 C4 N1 121.0(2) . . ? O3 C4 N2 120.7(2) . . ? N1 C4 N2 118.31(17) . . ? N1 C5 H51 110(3) . . ? N1 C5 H52 112(3) . . ? H51 C5 H52 112(4) . . ? N1 C5 H53 111(3) . . ? H51 C5 H53 107(4) . . ? H52 C5 H53 105(4) . . ? N2 C6 H61 112(3) . . ? N2 C6 H62 117(4) . . ? H61 C6 H62 123(4) . . ? N2 C6 H63 103(4) . . ? H61 C6 H63 97(4) . . ? H62 C6 H63 101(5) . . ? C7 N3 H31 117(2) . . ? C7 N3 H32 116.6(19) . . ? H31 N3 H32 126(3) . . ? O5 N4 O4 121.9(2) . . ? O5 N4 C10 119.0(2) . . ? O4 N4 C10 119.0(2) . . ? N3 C7 C12 120.8(2) . . ? N3 C7 C8 121.1(2) . . ? C12 C7 C8 118.04(19) . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 116.2(15) . . ? C7 C8 H8 122.6(15) . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 119.4(17) . . ? C10 C9 H9 120.7(17) . . ? C11 C10 C9 120.6(2) . . ? C11 C10 N4 119.7(2) . . ? C9 C10 N4 119.7(2) . . ? C12 C11 C10 119.6(2) . . ? C12 C11 H11 120.9(15) . . ? C10 C11 H11 119.4(15) . . ? C11 C12 C7 120.99(19) . . ? C11 C12 H12 119.5(13) . . ? C7 C12 H12 119.5(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.203 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.039 #===END data_(4) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-dimethylbarbituric acid . 2,6-diamino-4-phenyl-1,3,5-triazine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H34 N14 O6' _chemical_formula_weight 686.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21 / 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 11.2230(10) _cell_length_b 7.226(2) _cell_length_c 40.737(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.530(10) _cell_angle_gamma 90.00 _cell_volume 3303.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7135 _diffrn_reflns_av_R_equivalents 0.019 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6435 _reflns_number_gt 3539 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf nonius, 1984' _computing_data_reduction 'MolEN, C.K. Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1983, 1995) ; _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^)+(0.1057P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6435 _refine_ls_number_parameters 535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1286 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.2031 _refine_ls_wR_factor_gt 0.1721 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.005 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 O11 O 0.3397(2) 0.1558(5) 0.00577(7) 0.0772(8) Uani 1 1 d . . . O21 O -0.0345(3) 0.1272(4) -0.04585(7) 0.0781(8) Uani 1 1 d . . . O31 O 0.3035(3) 0.0477(5) -0.10277(6) 0.0871(10) Uani 1 1 d . . . N11 N 0.3226(3) 0.0890(4) -0.04780(7) 0.0599(8) Uani 1 1 d . . . N21 N 0.1333(3) 0.0747(4) -0.07400(7) 0.0551(7) Uani 1 1 d . . . C11 C 0.2758(3) 0.1284(5) -0.01741(9) 0.0557(9) Uani 1 1 d . . . C21 C 0.1449(3) 0.1324(7) -0.01519(10) 0.0562(9) Uani 1 1 d . . . C31 C 0.0724(3) 0.1137(5) -0.04569(9) 0.0545(9) Uani 1 1 d . . . C41 C 0.2561(4) 0.0699(5) -0.07638(10) 0.0610(10) Uani 1 1 d . . . C51 C 0.4526(4) 0.0735(8) -0.05133(12) 0.0887(15) Uani 1 1 d . . . H511 H 0.4885 0.0523 -0.0302 0.106 Uiso 1 1 calc R . . H512 H 0.4834 0.1860 -0.0605 0.106 Uiso 1 1 calc R . . H513 H 0.4707 -0.0280 -0.0656 0.106 Uiso 1 1 calc R . . C61 C 0.0653(4) 0.0465(6) -0.10458(9) 0.0705(11) Uani 1 1 d . . . H613 H 0.0834 -0.0732 -0.1135 0.085 Uiso 1 1 calc R . . H614 H 0.0863 0.1404 -0.1202 0.085 Uiso 1 1 calc R . . H615 H -0.0184 0.0539 -0.1001 0.085 Uiso 1 1 calc R . . O12 O 0.4606(3) 0.5135(6) 0.10755(9) 0.1002(11) Uani 1 1 d . . . O22 O 0.7660(3) 0.6694(6) 0.17958(7) 0.1013(12) Uani 1 1 d . . . O32 O 0.4606(3) 1.0624(5) 0.16034(10) 0.1122(13) Uani 1 1 d . . . N12 N 0.4521(3) 0.7818(5) 0.13633(8) 0.0656(9) Uani 1 1 d . . . N22 N 0.6133(3) 0.8672(5) 0.17170(8) 0.0705(10) Uani 1 1 d . . . C12 C 0.5019(4) 0.6124(7) 0.12897(11) 0.0681(11) Uani 1 1 d . . . C22 C 0.6062(4) 0.5603(6) 0.14848(10) 0.0704(11) Uani 1 1 d . . . H221 H 0.5818 0.4636 0.1635 0.084 Uiso 1 1 calc R . . H222 H 0.6635 0.5055 0.1337 0.084 Uiso 1 1 calc R . . C32 C 0.6679(3) 0.6982(7) 0.16741(9) 0.0687(12) Uani 1 1 d . . . C42 C 0.5058(4) 0.9147(7) 0.15635(10) 0.0684(11) Uani 1 1 d . . . C52 C 0.3404(4) 0.8348(9) 0.11932(12) 0.0979(17) Uani 1 1 d . . . H521 H 0.3143 0.7349 0.1055 0.118 Uiso 1 1 calc R . . H522 H 0.3540 0.9429 0.1062 0.118 Uiso 1 1 calc R . . H523 H 0.2802 0.8609 0.1353 0.118 Uiso 1 1 calc R . . C62 C 0.6763(6) 1.0074(11) 0.19001(18) 0.148(3) Uani 1 1 d . . . H623 H 0.6208 1.0982 0.1977 0.177 Uiso 1 1 calc R . . H625 H 0.7337 1.0659 0.1761 0.177 Uiso 1 1 calc R . . H624 H 0.7164 0.9515 0.2084 0.177 Uiso 1 1 calc R . . N31 N 0.0455(2) 0.3607(4) 0.06109(6) 0.0476(7) Uani 1 1 d . . . N41 N -0.0819(2) 0.4729(4) 0.10297(6) 0.0429(6) Uani 1 1 d . . . N51 N 0.1258(2) 0.4368(4) 0.11380(6) 0.0469(7) Uani 1 1 d . . . N61 N 0.2448(3) 0.3234(6) 0.07314(9) 0.0715(10) Uani 1 1 d . . . N71 N 0.0004(3) 0.5519(4) 0.15269(7) 0.0502(7) Uani 1 1 d . . . C71 C -0.0599(3) 0.4108(4) 0.07302(8) 0.0419(7) Uani 1 1 d . . . C81 C 0.1353(3) 0.3778(5) 0.08323(8) 0.0478(8) Uani 1 1 d . . . C91 C 0.0155(3) 0.4850(4) 0.12243(7) 0.0414(7) Uani 1 1 d . . . C101 C -0.1635(3) 0.3961(4) 0.04993(7) 0.0424(7) Uani 1 1 d . . . C111 C -0.1486(3) 0.3603(5) 0.01723(8) 0.0525(9) Uani 1 1 d . . . C121 C -0.2451(4) 0.3458(6) -0.00424(10) 0.0639(10) Uani 1 1 d . . . C131 C -0.3579(4) 0.3677(6) 0.00824(12) 0.0744(13) Uani 1 1 d . . . C141 C -0.3754(4) 0.4035(7) 0.04073(11) 0.0772(13) Uani 1 1 d . . . C151 C -0.2786(3) 0.4193(6) 0.06157(11) 0.0659(10) Uani 1 1 d . . . N32 N 0.2328(2) 0.6526(3) 0.19194(6) 0.0374(6) Uani 1 1 d . . . N42 N 0.3509(2) 0.8007(3) 0.23263(6) 0.0396(6) Uani 1 1 d . . . N52 N 0.4093(2) 0.5047(3) 0.21203(6) 0.0419(6) Uani 1 1 d . . . N62 N 0.2966(3) 0.3762(4) 0.17143(8) 0.0504(7) Uani 1 1 d . . . N72 N 0.5208(3) 0.6548(5) 0.25070(8) 0.0527(8) Uani 1 1 d . . . C72 C 0.2572(2) 0.7908(4) 0.21264(7) 0.0342(6) Uani 1 1 d . . . C82 C 0.3133(2) 0.5127(4) 0.19262(7) 0.0354(7) Uani 1 1 d . . . C92 C 0.4251(3) 0.6529(4) 0.23169(7) 0.0382(7) Uani 1 1 d . . . C102 C 0.1720(2) 0.9480(4) 0.21364(7) 0.0359(7) Uani 1 1 d . . . C112 C 0.0929(3) 0.9781(5) 0.18770(8) 0.0446(8) Uani 1 1 d . . . C122 C 0.0131(3) 1.1236(5) 0.18853(9) 0.0566(9) Uani 1 1 d . . . C132 C 0.0106(4) 1.2388(5) 0.21537(9) 0.0605(10) Uani 1 1 d . . . C142 C 0.0881(3) 1.2105(5) 0.24138(10) 0.0567(9) Uani 1 1 d . . . C152 C 0.1690(3) 1.0661(5) 0.24030(8) 0.0434(7) Uani 1 1 d . . . H211 H 0.125(3) 0.230(5) -0.0046(8) 0.044(9) Uiso 1 1 d . . . H212 H 0.122(4) 0.044(6) -0.0003(10) 0.069(12) Uiso 1 1 d . . . H611 H 0.315(3) 0.362(5) 0.0874(9) 0.061(10) Uiso 1 1 d . . . H612 H 0.260(4) 0.258(7) 0.0514(13) 0.109(16) Uiso 1 1 d . . . H711 H -0.077(4) 0.587(5) 0.1586(8) 0.058(10) Uiso 1 1 d . . . H712 H 0.063(3) 0.561(5) 0.1667(8) 0.054(10) Uiso 1 1 d . . . H111 H -0.067(4) 0.348(5) 0.0111(9) 0.068(11) Uiso 1 1 d . . . H121 H -0.227(4) 0.330(6) -0.0286(11) 0.089(14) Uiso 1 1 d . . . H131 H -0.419(4) 0.348(6) -0.0064(11) 0.080(12) Uiso 1 1 d . . . H141 H -0.461(4) 0.415(6) 0.0478(9) 0.077(12) Uiso 1 1 d . . . H151 H -0.285(3) 0.455(5) 0.0863(10) 0.062(10) Uiso 1 1 d . . . H621 H 0.343(3) 0.287(6) 0.1716(9) 0.068(13) Uiso 1 1 d . . . H622 H 0.237(4) 0.372(6) 0.1570(10) 0.072(12) Uiso 1 1 d . . . H721 H 0.527(3) 0.734(5) 0.2631(9) 0.047(11) Uiso 1 1 d . . . H722 H 0.566(4) 0.554(6) 0.2530(9) 0.066(12) Uiso 1 1 d . . . H112 H 0.094(3) 0.894(5) 0.1708(9) 0.060(11) Uiso 1 1 d . . . H122 H -0.045(3) 1.138(5) 0.1663(9) 0.074(11) Uiso 1 1 d . . . H132 H -0.053(3) 1.329(6) 0.2177(9) 0.065(11) Uiso 1 1 d . . . H142 H 0.092(3) 1.279(6) 0.2590(10) 0.068(12) Uiso 1 1 d . . . H152 H 0.217(2) 1.058(4) 0.2584(7) 0.030(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0728(18) 0.100(2) 0.0584(16) -0.0161(16) -0.0092(14) -0.0043(16) O21 0.0631(19) 0.092(2) 0.080(2) -0.0029(16) 0.0007(14) 0.0070(16) O31 0.091(2) 0.124(3) 0.0470(15) -0.0010(17) 0.0231(14) 0.0021(19) N11 0.0551(18) 0.067(2) 0.0576(18) 0.0057(15) 0.0070(14) -0.0044(15) N21 0.067(2) 0.0465(17) 0.0521(17) 0.0033(14) -0.0007(14) -0.0009(14) C11 0.063(2) 0.050(2) 0.055(2) -0.0037(18) 0.0020(18) -0.0036(17) C21 0.064(2) 0.051(2) 0.054(2) -0.004(2) 0.0073(18) 0.0088(19) C31 0.060(2) 0.038(2) 0.066(2) 0.0053(17) 0.0036(18) 0.0007(16) C41 0.066(2) 0.056(2) 0.061(2) 0.0090(19) 0.0066(19) -0.0046(19) C51 0.061(3) 0.128(4) 0.077(3) 0.003(3) 0.015(2) -0.012(3) C61 0.097(3) 0.066(3) 0.048(2) 0.002(2) -0.015(2) 0.000(2) O12 0.073(2) 0.127(3) 0.101(2) -0.021(2) 0.0071(18) -0.0131(19) O22 0.0636(18) 0.175(4) 0.0658(18) -0.005(2) -0.0039(14) 0.048(2) O32 0.109(3) 0.099(3) 0.128(3) -0.011(2) 0.017(2) 0.054(2) N12 0.0453(17) 0.091(3) 0.0608(19) 0.0218(19) 0.0091(14) 0.0131(18) N22 0.0590(19) 0.102(3) 0.0510(18) -0.0095(18) 0.0061(15) 0.015(2) C12 0.054(2) 0.087(3) 0.063(2) 0.006(2) 0.0160(19) 0.003(2) C22 0.070(3) 0.079(3) 0.063(2) 0.005(2) 0.012(2) 0.021(2) C32 0.053(2) 0.102(3) 0.052(2) 0.007(2) 0.0141(18) 0.028(2) C42 0.059(2) 0.080(3) 0.067(3) 0.006(2) 0.022(2) 0.017(2) C52 0.053(2) 0.147(5) 0.094(3) 0.041(3) 0.002(2) 0.018(3) C62 0.104(5) 0.180(7) 0.159(6) -0.068(6) -0.006(4) 0.010(5) N31 0.0436(15) 0.0516(17) 0.0475(15) -0.0111(13) -0.0068(12) 0.0032(13) N41 0.0449(15) 0.0409(15) 0.0428(15) -0.0036(12) -0.0050(11) 0.0051(12) N51 0.0469(15) 0.0496(16) 0.0441(15) -0.0112(13) -0.0080(12) 0.0076(13) N61 0.0442(17) 0.111(3) 0.0589(19) -0.024(2) -0.0051(15) 0.0153(18) N71 0.0484(17) 0.0524(18) 0.0494(17) -0.0076(14) -0.0092(14) 0.0126(14) C71 0.0429(17) 0.0325(16) 0.0501(19) -0.0003(14) -0.0091(14) 0.0024(13) C81 0.0449(18) 0.054(2) 0.0447(18) -0.0075(16) -0.0057(14) 0.0049(15) C91 0.0449(18) 0.0371(17) 0.0421(17) -0.0019(14) -0.0073(14) 0.0055(14) C101 0.0486(18) 0.0370(17) 0.0414(17) -0.0044(14) -0.0093(14) 0.0028(14) C111 0.055(2) 0.053(2) 0.049(2) -0.0082(16) -0.0114(17) 0.0072(17) C121 0.071(3) 0.068(3) 0.053(2) -0.016(2) -0.0219(19) 0.013(2) C131 0.063(3) 0.074(3) 0.086(3) -0.013(2) -0.035(2) 0.017(2) C141 0.050(2) 0.117(4) 0.064(3) -0.016(3) -0.0124(19) 0.016(2) C151 0.050(2) 0.082(3) 0.065(2) -0.011(2) -0.0069(18) 0.007(2) N32 0.0375(13) 0.0344(14) 0.0404(13) -0.0070(11) -0.0046(10) 0.0039(11) N42 0.0410(14) 0.0320(13) 0.0456(14) -0.0039(12) -0.0113(11) 0.0009(11) N52 0.0381(14) 0.0345(14) 0.0529(15) -0.0021(12) -0.0099(12) 0.0053(11) N62 0.0483(17) 0.0443(18) 0.0584(18) -0.0167(14) -0.0145(14) 0.0112(14) N72 0.0527(19) 0.0383(17) 0.067(2) -0.0134(16) -0.0254(15) 0.0078(14) C72 0.0357(15) 0.0315(15) 0.0355(15) 0.0057(13) -0.0008(12) -0.0022(12) C82 0.0359(15) 0.0339(16) 0.0363(15) 0.0014(13) -0.0032(12) -0.0015(13) C92 0.0398(16) 0.0316(16) 0.0431(17) 0.0005(13) -0.0068(14) -0.0013(13) C102 0.0348(15) 0.0305(15) 0.0423(16) 0.0018(13) 0.0014(12) 0.0003(12) C112 0.0482(19) 0.0385(18) 0.0470(18) -0.0011(16) -0.0045(15) 0.0101(15) C122 0.059(2) 0.051(2) 0.060(2) -0.0028(18) -0.0091(17) 0.0136(17) C132 0.067(2) 0.052(2) 0.063(2) -0.0005(18) 0.0011(19) 0.0230(19) C142 0.067(2) 0.048(2) 0.055(2) -0.0127(19) 0.0082(18) 0.0113(18) C152 0.0436(17) 0.0450(19) 0.0416(18) -0.0045(15) -0.0038(14) 0.0004(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O11 C11 1.197(4) . ? O21 C31 1.204(4) . ? O31 C41 1.214(4) . ? N11 C11 1.379(5) . ? N11 C41 1.384(5) . ? N11 C51 1.471(5) . ? N21 C31 1.375(5) . ? N21 C41 1.382(5) . ? N21 C61 1.470(5) . ? C11 C21 1.473(5) . ? C21 C31 1.485(5) . ? C21 H211 0.86(4) . ? C21 H212 0.92(4) . ? C51 H511 0.9600 . ? C51 H512 0.9600 . ? C51 H513 0.9600 . ? C61 H613 0.9600 . ? C61 H614 0.9600 . ? C61 H615 0.9600 . ? O12 C12 1.216(5) . ? O22 C32 1.221(5) . ? O32 C42 1.193(5) . ? N12 C12 1.380(5) . ? N12 C42 1.394(6) . ? N12 C52 1.477(5) . ? N22 C32 1.378(5) . ? N22 C42 1.397(5) . ? N22 C62 1.440(7) . ? C12 C22 1.459(6) . ? C22 C32 1.434(6) . ? C22 H221 0.9700 . ? C22 H222 0.9700 . ? C52 H521 0.9600 . ? C52 H522 0.9600 . ? C52 H523 0.9600 . ? C62 H623 0.9600 . ? C62 H625 0.9600 . ? C62 H624 0.9600 . ? N31 C71 1.333(4) . ? N31 C81 1.351(4) . ? N41 C71 1.325(4) . ? N41 C91 1.347(4) . ? N51 C81 1.322(4) . ? N51 C91 1.337(4) . ? N61 C81 1.357(4) . ? N61 H611 1.01(4) . ? N61 H612 1.02(5) . ? N71 C91 1.336(4) . ? N71 H711 0.94(4) . ? N71 H712 0.90(4) . ? C71 C101 1.493(4) . ? C101 C111 1.369(5) . ? C101 C151 1.390(5) . ? C111 C121 1.390(5) . ? C111 H111 0.95(4) . ? C121 C131 1.377(6) . ? C121 H121 1.02(4) . ? C131 C141 1.365(6) . ? C131 H131 0.92(4) . ? C141 C151 1.377(5) . ? C141 H141 1.01(4) . ? C151 H151 1.04(4) . ? N32 C72 1.334(4) . ? N32 C82 1.356(4) . ? N42 C72 1.326(4) . ? N42 C92 1.355(4) . ? N52 C82 1.332(4) . ? N52 C92 1.348(4) . ? N62 C82 1.323(4) . ? N62 H621 0.83(4) . ? N62 H622 0.89(4) . ? N72 C92 1.318(4) . ? N72 H721 0.76(4) . ? N72 H722 0.89(4) . ? C72 C102 1.486(4) . ? C102 C152 1.382(4) . ? C102 C112 1.391(4) . ? C112 C122 1.381(5) . ? C112 H112 0.92(4) . ? C122 C132 1.374(5) . ? C122 H122 1.12(4) . ? C132 C142 1.380(5) . ? C132 H132 0.97(4) . ? C142 C152 1.384(5) . ? C142 H142 0.87(4) . ? C152 H152 0.91(3) . ? 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 C11 N11 C41 124.7(3) . . ? C11 N11 C51 119.3(3) . . ? C41 N11 C51 116.0(3) . . ? C31 N21 C41 124.6(3) . . ? C31 N21 C61 118.7(3) . . ? C41 N21 C61 116.6(3) . . ? O11 C11 N11 120.8(4) . . ? O11 C11 C21 122.6(4) . . ? N11 C11 C21 116.6(3) . . ? C11 C21 C31 119.1(3) . . ? C11 C21 H211 108(2) . . ? C31 C21 H211 111(2) . . ? C11 C21 H212 108(2) . . ? C31 C21 H212 110(2) . . ? H211 C21 H212 99(3) . . ? O21 C31 N21 121.0(4) . . ? O21 C31 C21 122.4(4) . . ? N21 C31 C21 116.6(3) . . ? O31 C41 N21 120.7(4) . . ? O31 C41 N11 121.4(4) . . ? N21 C41 N11 117.9(3) . . ? N11 C51 H511 109.5 . . ? N11 C51 H512 109.5 . . ? H511 C51 H512 109.5 . . ? N11 C51 H513 109.5 . . ? H511 C51 H513 109.5 . . ? H512 C51 H513 109.5 . . ? N21 C61 H613 109.5 . . ? N21 C61 H614 109.5 . . ? H613 C61 H614 109.5 . . ? N21 C61 H615 109.5 . . ? H613 C61 H615 109.5 . . ? H614 C61 H615 109.5 . . ? C12 N12 C42 124.4(3) . . ? C12 N12 C52 118.1(4) . . ? C42 N12 C52 117.2(4) . . ? C32 N22 C42 123.0(4) . . ? C32 N22 C62 118.2(4) . . ? C42 N22 C62 118.5(4) . . ? O12 C12 N12 121.7(4) . . ? O12 C12 C22 122.5(4) . . ? N12 C12 C22 115.8(4) . . ? C32 C22 C12 119.6(4) . . ? C32 C22 H221 107.4 . . ? C12 C22 H221 107.4 . . ? C32 C22 H222 107.4 . . ? C12 C22 H222 107.4 . . ? H221 C22 H222 106.9 . . ? O22 C32 N22 119.9(5) . . ? O22 C32 C22 121.9(4) . . ? N22 C32 C22 118.1(4) . . ? O32 C42 N12 120.9(4) . . ? O32 C42 N22 121.7(5) . . ? N12 C42 N22 117.4(4) . . ? N12 C52 H521 109.5 . . ? N12 C52 H522 109.5 . . ? H521 C52 H522 109.5 . . ? N12 C52 H523 109.5 . . ? H521 C52 H523 109.5 . . ? H522 C52 H523 109.5 . . ? N22 C62 H623 109.5 . . ? N22 C62 H625 109.5 . . ? H623 C62 H625 109.5 . . ? N22 C62 H624 109.5 . . ? H623 C62 H624 109.5 . . ? H625 C62 H624 109.5 . . ? C71 N31 C81 113.0(3) . . ? C71 N41 C91 114.0(3) . . ? C81 N51 C91 114.5(3) . . ? C81 N61 H611 117(2) . . ? C81 N61 H612 124(3) . . ? H611 N61 H612 119(3) . . ? C91 N71 H711 117(2) . . ? C91 N71 H712 120(2) . . ? H711 N71 H712 122(3) . . ? N41 C71 N31 127.0(3) . . ? N41 C71 C101 116.9(3) . . ? N31 C71 C101 116.1(3) . . ? N51 C81 N31 126.3(3) . . ? N51 C81 N61 117.4(3) . . ? N31 C81 N61 116.3(3) . . ? N71 C91 N51 117.5(3) . . ? N71 C91 N41 117.2(3) . . ? N51 C91 N41 125.2(3) . . ? C111 C101 C151 118.5(3) . . ? C111 C101 C71 121.7(3) . . ? C151 C101 C71 119.8(3) . . ? C101 C111 C121 121.7(4) . . ? C101 C111 H111 113(2) . . ? C121 C111 H111 125(2) . . ? C131 C121 C111 118.2(4) . . ? C131 C121 H121 124(2) . . ? C111 C121 H121 118(2) . . ? C141 C131 C121 121.4(4) . . ? C141 C131 H131 123(3) . . ? C121 C131 H131 115(3) . . ? C131 C141 C151 119.6(4) . . ? C131 C141 H141 116(2) . . ? C151 C141 H141 124(2) . . ? C141 C151 C101 120.6(4) . . ? C141 C151 H151 124(2) . . ? C101 C151 H151 116(2) . . ? C72 N32 C82 114.4(2) . . ? C72 N42 C92 115.1(2) . . ? C82 N52 C92 114.8(2) . . ? C82 N62 H621 119(3) . . ? C82 N62 H622 124(3) . . ? H621 N62 H622 117(4) . . ? C92 N72 H721 117(3) . . ? C92 N72 H722 121(2) . . ? H721 N72 H722 120(4) . . ? N42 C72 N32 125.8(3) . . ? N42 C72 C102 116.7(3) . . ? N32 C72 C102 117.5(2) . . ? N62 C82 N52 117.6(3) . . ? N62 C82 N32 116.9(3) . . ? N52 C82 N32 125.4(3) . . ? N72 C92 N52 117.3(3) . . ? N72 C92 N42 118.2(3) . . ? N52 C92 N42 124.5(2) . . ? C152 C102 C112 118.7(3) . . ? C152 C102 C72 120.9(3) . . ? C112 C102 C72 120.3(3) . . ? C122 C112 C102 120.6(3) . . ? C122 C112 H112 122(2) . . ? C102 C112 H112 117(2) . . ? C132 C122 C112 119.9(3) . . ? C132 C122 H122 125(2) . . ? C112 C122 H122 115(2) . . ? C122 C132 C142 120.2(3) . . ? C122 C132 H132 120(2) . . ? C142 C132 H132 119(2) . . ? C132 C142 C152 119.8(4) . . ? C132 C142 H142 125(3) . . ? C152 C142 H142 115(3) . . ? C102 C152 C142 120.7(3) . . ? C102 C152 H152 125.4(18) . . ? C142 C152 H152 113.9(18) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.607 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.053 #===END data_(5) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3-dimethylbarbituric acid . 2,6-diaminopyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H15 N5 O3' _chemical_formula_weight 265.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _symmetry_cell_setting 'triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2620(10) _cell_length_b 9.466(3) _cell_length_c 9.8390(10) _cell_angle_alpha 91.28(2) _cell_angle_beta 109.460(10) _cell_angle_gamma 94.01(2) _cell_volume 635.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 13 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2988 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 26.97 _reflns_number_total 2765 _reflns_number_gt 2079 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4, Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4, Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, C.K. Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1983, 1995) ; _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^)+(0.0626P)^2^+0.0824P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2765 _refine_ls_number_parameters 232 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0605 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.14252(18) 0.00112(12) -0.26976(11) 0.0506(3) Uani 1 1 d . . . O2 O 0.43096(17) -0.25684(12) 0.13818(12) 0.0483(3) Uani 1 1 d . . . O3 O 0.26422(18) 0.18991(12) 0.18283(12) 0.0475(3) Uani 1 1 d . . . N1 N 0.19328(17) 0.09282(12) -0.04325(13) 0.0344(3) Uani 1 1 d . . . N2 N 0.33280(17) -0.03699(13) 0.15956(12) 0.0340(3) Uani 1 1 d . . . C1 C 0.2046(2) -0.01804(15) -0.13717(14) 0.0342(3) Uani 1 1 d . . . C2 C 0.2844(2) -0.13891(16) -0.07378(15) 0.0361(3) Uani 1 1 d . . . C3 C 0.3532(2) -0.15166(14) 0.07396(15) 0.0330(3) Uani 1 1 d . . . C4 C 0.2639(2) 0.08737(15) 0.10404(15) 0.0335(3) Uani 1 1 d . . . C5 C 0.1164(3) 0.22534(19) -0.1012(2) 0.0469(4) Uani 1 1 d . . . N3 N 0.68715(18) -0.37209(13) 0.36877(13) 0.0336(3) Uani 1 1 d . . . N4 N 0.4873(2) -0.54378(16) 0.20834(16) 0.0504(4) Uani 1 1 d . . . N5 N 0.8830(2) -0.18403(15) 0.50463(16) 0.0470(4) Uani 1 1 d . . . C6 C 0.4014(3) -0.0436(2) 0.31662(17) 0.0490(4) Uani 1 1 d . . . C7 C 0.6118(2) -0.50944(15) 0.34185(16) 0.0371(3) Uani 1 1 d . . . C8 C 0.6692(3) -0.60226(18) 0.4521(2) 0.0460(4) Uani 1 1 d . . . C9 C 0.7966(3) -0.54993(19) 0.5844(2) 0.0484(4) Uani 1 1 d . . . C10 C 0.8725(2) -0.41152(18) 0.60941(17) 0.0424(4) Uani 1 1 d . . . C11 C 0.8182(2) -0.31985(16) 0.49732(15) 0.0350(3) Uani 1 1 d . . . H2 H 0.297(2) -0.2155(19) -0.1326(18) 0.040(4) Uiso 1 1 d . . . H51 H 0.226(3) 0.297(2) -0.097(2) 0.070(6) Uiso 1 1 d . . . H52 H 0.035(3) 0.261(2) -0.050(2) 0.068(6) Uiso 1 1 d . . . H53 H 0.040(3) 0.206(2) -0.200(2) 0.065(6) Uiso 1 1 d . . . H61 H 0.386(4) -0.147(3) 0.342(3) 0.090(8) Uiso 1 1 d . . . H62 H 0.316(4) 0.010(3) 0.356(3) 0.093(8) Uiso 1 1 d . . . H63 H 0.532(4) -0.004(3) 0.355(3) 0.089(8) Uiso 1 1 d . . . H30 H 0.633(2) -0.3108(18) 0.2982(19) 0.044(5) Uiso 1 1 d . . . H410 H 0.436(3) -0.469(2) 0.153(2) 0.062(6) Uiso 1 1 d . . . H420 H 0.419(3) -0.628(2) 0.194(2) 0.061(6) Uiso 1 1 d . . . H510 H 0.863(3) -0.131(2) 0.423(2) 0.061(6) Uiso 1 1 d . . . H520 H 0.969(3) -0.146(2) 0.589(2) 0.064(6) Uiso 1 1 d . . . H8 H 0.615(3) -0.702(2) 0.434(2) 0.069(6) Uiso 1 1 d . . . H9 H 0.836(3) -0.613(2) 0.664(2) 0.058(5) Uiso 1 1 d . . . H10 H 0.961(3) -0.374(2) 0.702(2) 0.055(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0636(8) 0.0496(7) 0.0264(5) 0.0042(5) 0.0014(5) -0.0092(6) O2 0.0558(7) 0.0346(6) 0.0430(6) 0.0045(5) 0.0007(5) 0.0071(5) O3 0.0607(7) 0.0347(6) 0.0472(7) -0.0076(5) 0.0197(5) -0.0013(5) N1 0.0352(6) 0.0305(6) 0.0339(6) 0.0050(5) 0.0074(5) -0.0003(5) N2 0.0379(6) 0.0339(6) 0.0259(6) 0.0011(5) 0.0061(5) -0.0017(5) C1 0.0332(7) 0.0360(8) 0.0272(7) 0.0010(6) 0.0042(5) -0.0080(6) C2 0.0385(8) 0.0339(8) 0.0311(7) -0.0050(6) 0.0071(6) -0.0036(6) C3 0.0314(7) 0.0291(7) 0.0329(7) 0.0005(5) 0.0043(6) -0.0034(5) C4 0.0331(7) 0.0302(7) 0.0346(7) -0.0002(6) 0.0099(6) -0.0052(6) C5 0.0487(10) 0.0393(9) 0.0512(10) 0.0148(7) 0.0133(8) 0.0074(7) N3 0.0396(7) 0.0287(6) 0.0308(6) 0.0030(5) 0.0095(5) 0.0019(5) N4 0.0619(9) 0.0325(8) 0.0486(8) -0.0050(6) 0.0104(7) -0.0075(7) N5 0.0589(9) 0.0378(7) 0.0329(7) 0.0004(6) 0.0025(6) -0.0069(6) C6 0.0615(12) 0.0540(11) 0.0272(8) 0.0026(7) 0.0089(8) 0.0049(9) C7 0.0412(8) 0.0304(7) 0.0428(8) -0.0007(6) 0.0183(6) 0.0027(6) C8 0.0526(10) 0.0315(8) 0.0578(10) 0.0108(7) 0.0224(8) 0.0069(7) C9 0.0518(10) 0.0474(10) 0.0515(10) 0.0221(8) 0.0209(8) 0.0167(8) C10 0.0433(9) 0.0491(9) 0.0335(8) 0.0093(7) 0.0096(7) 0.0104(7) C11 0.0369(7) 0.0374(8) 0.0311(7) 0.0010(6) 0.0115(6) 0.0041(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 1.2522(17) . ? O2 C3 1.2565(18) . ? O3 C4 1.2280(18) . ? N1 C4 1.3702(18) . ? N1 C1 1.4075(19) . ? N1 C5 1.459(2) . ? N2 C4 1.3651(19) . ? N2 C3 1.4050(19) . ? N2 C6 1.4614(19) . ? C1 C2 1.385(2) . ? C2 C3 1.382(2) . ? C2 H2 0.946(17) . ? C5 H51 1.00(2) . ? C5 H52 0.97(2) . ? C5 H53 0.95(2) . ? N3 C7 1.3596(19) . ? N3 C11 1.3616(18) . ? N3 H30 0.918(18) . ? N4 C7 1.341(2) . ? N4 H410 0.93(2) . ? N4 H420 0.89(2) . ? N5 C11 1.330(2) . ? N5 H510 0.93(2) . ? N5 H520 0.90(2) . ? C6 H61 1.02(3) . ? C6 H62 0.99(3) . ? C6 H63 0.94(3) . ? C7 C8 1.384(2) . ? C8 C9 1.379(3) . ? C8 H8 0.98(2) . ? C9 C10 1.369(3) . ? C9 H9 0.97(2) . ? C10 C11 1.388(2) . ? C10 H10 0.96(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N1 C1 123.12(12) . . ? C4 N1 C5 116.73(13) . . ? C1 N1 C5 120.00(13) . . ? C4 N2 C3 123.07(12) . . ? C4 N2 C6 116.91(13) . . ? C3 N2 C6 119.85(13) . . ? O1 C1 C2 125.87(14) . . ? O1 C1 N1 117.52(13) . . ? C2 C1 N1 116.62(12) . . ? C3 C2 C1 122.69(14) . . ? C3 C2 H2 117.7(10) . . ? C1 C2 H2 119.6(10) . . ? O2 C3 C2 125.80(14) . . ? O2 C3 N2 117.29(13) . . ? C2 C3 N2 116.91(13) . . ? O3 C4 N2 121.38(13) . . ? O3 C4 N1 121.36(14) . . ? N2 C4 N1 117.26(12) . . ? N1 C5 H51 110.1(13) . . ? N1 C5 H52 110.7(13) . . ? H51 C5 H52 111.5(18) . . ? N1 C5 H53 107.6(13) . . ? H51 C5 H53 107.4(18) . . ? H52 C5 H53 109.4(18) . . ? C7 N3 C11 124.13(13) . . ? C7 N3 H30 116.0(11) . . ? C11 N3 H30 119.5(11) . . ? C7 N4 H410 116.1(13) . . ? C7 N4 H420 117.1(13) . . ? H410 N4 H420 120.4(18) . . ? C11 N5 H510 122.6(12) . . ? C11 N5 H520 118.6(13) . . ? H510 N5 H520 117.8(19) . . ? N2 C6 H61 108.4(14) . . ? N2 C6 H62 109.2(14) . . ? H61 C6 H62 107(2) . . ? N2 C6 H63 109.2(15) . . ? H61 C6 H63 113(2) . . ? H62 C6 H63 110(2) . . ? N4 C7 N3 116.43(14) . . ? N4 C7 C8 125.26(15) . . ? N3 C7 C8 118.31(15) . . ? C9 C8 C7 118.26(16) . . ? C9 C8 H8 122.5(12) . . ? C7 C8 H8 119.2(12) . . ? C10 C9 C8 122.69(15) . . ? C10 C9 H9 117.6(12) . . ? C8 C9 H9 119.7(11) . . ? C9 C10 C11 118.72(16) . . ? C9 C10 H10 123.2(12) . . ? C11 C10 H10 118.0(12) . . ? N5 C11 N3 116.73(14) . . ? N5 C11 C10 125.45(15) . . ? N3 C11 C10 117.82(14) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.201 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.041 #===END data_(6) _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5'-hydroxy-5,5'-bi-(1,3-dimethylbarbituric acid). 4-aminopyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H20 N6 O7' _chemical_formula_weight 420.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'O' 'O' 0.0106 0.0060 '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' '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' _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 10.111(2) _cell_length_b 11.747(2) _cell_length_c 9.369(2) _cell_angle_alpha 107.720(10) _cell_angle_beta 109.660(10) _cell_angle_gamma 66.160(10) _cell_volume 940.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 13 _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w/2\q' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 120 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4782 _diffrn_reflns_av_R_equivalents 0.009 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.97 _reflns_number_total 4524 _reflns_number_gt 3840 _reflns_threshold_expression 'I>2sigma(I)' _computing_data_collection 'CAD4 Enraf-Nonius, 1984' _computing_cell_refinement 'CAD4 Enraf-Nonius, 1984' _computing_data_reduction 'MolEN, C.K. Fair, Enraf-Nonius, 1990' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material ; SHELXL-97 (Sheldrick, 1997), Nardelli( 1983, 1995) ; _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^)+(0.0667P)^2^+0.1839P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4524 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1119 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.002 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 O11 O 0.11819(11) -0.39409(9) 0.10553(11) 0.0429(2) Uani 1 1 d . . . O21 O 0.30223(10) -0.08601(8) 0.47127(10) 0.0359(2) Uani 1 1 d . . . O31 O 0.36601(14) -0.45324(10) 0.59570(13) 0.0550(3) Uani 1 1 d . . . N11 N 0.23580(13) -0.42005(9) 0.35316(13) 0.0381(2) Uani 1 1 d . . . N21 N 0.33669(11) -0.27079(9) 0.53322(12) 0.0330(2) Uani 1 1 d . . . C11 C 0.17839(13) -0.34681(10) 0.23919(14) 0.0314(2) Uani 1 1 d . . . C21 C 0.19051(12) -0.22561(10) 0.28425(13) 0.0281(2) Uani 1 1 d . . . C31 C 0.27535(12) -0.18787(10) 0.43004(13) 0.0276(2) Uani 1 1 d . . . C41 C 0.31603(14) -0.38587(11) 0.49962(15) 0.0368(3) Uani 1 1 d . . . C51 C 0.2051(3) -0.53918(16) 0.3153(3) 0.0635(5) Uani 1 1 d . . . C61 C 0.4173(2) -0.22838(18) 0.68921(18) 0.0507(4) Uani 1 1 d . . . O12 O 0.29101(14) -0.22898(10) 0.01730(14) 0.0558(3) Uani 1 1 d . . . O22 O -0.07136(12) 0.01175(10) 0.30389(15) 0.0531(3) Uani 1 1 d . . . O32 O 0.23611(12) 0.17875(9) 0.25236(13) 0.0494(3) Uani 1 1 d . . . O42 O 0.00346(11) -0.16731(10) 0.05019(11) 0.0423(2) Uani 1 1 d . . . N12 N 0.26747(11) -0.02664(9) 0.13845(11) 0.0316(2) Uani 1 1 d . . . N22 N 0.07518(12) 0.09797(9) 0.27009(12) 0.0335(2) Uani 1 1 d . . . C12 C 0.23242(14) -0.13481(11) 0.10217(14) 0.0329(2) Uani 1 1 d . . . C22 C 0.11662(13) -0.13403(10) 0.17356(13) 0.0295(2) Uani 1 1 d . . . C32 C 0.03271(13) -0.00254(11) 0.25705(14) 0.0331(2) Uani 1 1 d . . . C42 C 0.19518(13) 0.08904(11) 0.22294(14) 0.0323(2) Uani 1 1 d . . . C52 C 0.37899(18) -0.02716(16) 0.07079(19) 0.0455(3) Uani 1 1 d . . . C62 C -0.0105(2) 0.22397(13) 0.3439(2) 0.0502(4) Uani 1 1 d . . . N1 N 0.28495(14) 0.14202(11) 0.66424(14) 0.0445(3) Uani 1 1 d . . . N2 N 0.30622(19) 0.49675(12) 0.8685(2) 0.0590(4) Uani 1 1 d . . . C1 C 0.30072(15) 0.38055(11) 0.80346(15) 0.0366(3) Uani 1 1 d . . . C2 C 0.37953(16) 0.30182(13) 0.69009(17) 0.0414(3) Uani 1 1 d . . . C3 C 0.36927(17) 0.18525(13) 0.62433(16) 0.0440(3) Uani 1 1 d . . . C4 C 0.20991(17) 0.21349(14) 0.77291(18) 0.0461(3) Uani 1 1 d . . . C5 C 0.21605(16) 0.33085(13) 0.84423(17) 0.0426(3) Uani 1 1 d . . . H511 H 0.099(4) -0.523(3) 0.269(4) 0.122(11) Uiso 1 1 d . . . H521 H 0.257(3) -0.583(3) 0.392(3) 0.108(9) Uiso 1 1 d . . . H531 H 0.234(4) -0.592(4) 0.217(4) 0.136(12) Uiso 1 1 d . . . H611 H 0.501(3) -0.213(2) 0.684(3) 0.088(7) Uiso 1 1 d . . . H621 H 0.449(3) -0.287(3) 0.747(3) 0.106(9) Uiso 1 1 d . . . H631 H 0.350(3) -0.155(3) 0.738(3) 0.109(9) Uiso 1 1 d . . . H42 H 0.032(2) -0.249(2) 0.041(2) 0.056(5) Uiso 1 1 d . . . H512 H 0.447(2) -0.116(2) 0.043(3) 0.074(6) Uiso 1 1 d . . . H522 H 0.447(3) 0.010(3) 0.146(3) 0.101(8) Uiso 1 1 d . . . H532 H 0.336(3) 0.004(2) -0.017(3) 0.083(7) Uiso 1 1 d . . . H612 H -0.103(3) 0.250(2) 0.279(3) 0.080(7) Uiso 1 1 d . . . H622 H -0.022(3) 0.213(3) 0.440(3) 0.099(8) Uiso 1 1 d . . . H632 H 0.039(3) 0.278(3) 0.375(3) 0.098(8) Uiso 1 1 d . . . H1 H 0.280(2) 0.064(2) 0.612(3) 0.070(6) Uiso 1 1 d . . . H21 H 0.254(3) 0.542(2) 0.941(3) 0.076(6) Uiso 1 1 d . . . H22 H 0.359(3) 0.526(2) 0.833(3) 0.084(7) Uiso 1 1 d . . . H2 H 0.442(2) 0.3299(17) 0.661(2) 0.051(4) Uiso 1 1 d . . . H3 H 0.426(2) 0.128(2) 0.549(2) 0.065(5) Uiso 1 1 d . . . H4 H 0.152(2) 0.1782(18) 0.790(2) 0.054(5) Uiso 1 1 d . . . H5 H 0.158(2) 0.3783(19) 0.916(2) 0.062(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O11 0.0564(6) 0.0304(4) 0.0422(5) -0.0053(4) 0.0130(4) -0.0231(4) O21 0.0468(5) 0.0281(4) 0.0365(4) 0.0001(3) 0.0102(4) -0.0207(4) O31 0.0711(7) 0.0432(6) 0.0578(6) 0.0255(5) 0.0176(5) -0.0135(5) N11 0.0490(6) 0.0210(4) 0.0488(6) 0.0058(4) 0.0169(5) -0.0130(4) N21 0.0372(5) 0.0298(5) 0.0333(5) 0.0068(4) 0.0100(4) -0.0108(4) C11 0.0362(6) 0.0229(5) 0.0378(6) 0.0002(4) 0.0156(5) -0.0114(4) C21 0.0341(5) 0.0221(5) 0.0314(5) 0.0030(4) 0.0113(4) -0.0116(4) C31 0.0309(5) 0.0226(5) 0.0321(5) 0.0022(4) 0.0137(4) -0.0091(4) C41 0.0412(6) 0.0284(6) 0.0444(7) 0.0111(5) 0.0182(5) -0.0060(5) C51 0.0848(13) 0.0304(7) 0.0823(13) 0.0147(8) 0.0139(11) -0.0287(8) C61 0.0533(9) 0.0596(9) 0.0379(7) 0.0139(7) 0.0002(6) -0.0233(8) O12 0.0811(8) 0.0357(5) 0.0643(7) -0.0090(5) 0.0485(6) -0.0217(5) O22 0.0507(6) 0.0395(5) 0.0816(8) 0.0097(5) 0.0397(6) -0.0100(4) O32 0.0583(6) 0.0373(5) 0.0600(6) -0.0007(4) 0.0148(5) -0.0306(5) O42 0.0464(5) 0.0418(5) 0.0387(5) 0.0107(4) -0.0020(4) -0.0228(4) N12 0.0359(5) 0.0310(5) 0.0340(5) 0.0057(4) 0.0121(4) -0.0149(4) N22 0.0386(5) 0.0217(4) 0.0399(5) 0.0043(4) 0.0142(4) -0.0074(4) C12 0.0422(6) 0.0281(5) 0.0328(6) 0.0040(4) 0.0145(5) -0.0131(5) C22 0.0349(5) 0.0247(5) 0.0320(5) 0.0039(4) 0.0095(4) -0.0132(4) C32 0.0347(6) 0.0272(5) 0.0399(6) 0.0085(4) 0.0131(5) -0.0082(4) C42 0.0368(6) 0.0287(5) 0.0326(5) 0.0054(4) 0.0056(4) -0.0149(4) C52 0.0485(8) 0.0549(9) 0.0473(8) 0.0088(7) 0.0205(6) -0.0253(7) C62 0.0520(9) 0.0263(6) 0.0647(10) -0.0008(6) 0.0238(8) -0.0049(6) N1 0.0534(7) 0.0272(5) 0.0455(6) 0.0003(4) 0.0047(5) -0.0173(5) N2 0.0781(10) 0.0319(6) 0.0725(9) -0.0083(6) 0.0333(8) -0.0252(6) C1 0.0428(6) 0.0267(5) 0.0402(6) 0.0021(5) 0.0131(5) -0.0124(5) C2 0.0479(7) 0.0343(6) 0.0480(7) 0.0082(5) 0.0228(6) -0.0106(5) C3 0.0543(8) 0.0336(6) 0.0368(6) 0.0018(5) 0.0169(6) -0.0066(6) C4 0.0454(7) 0.0423(7) 0.0584(9) 0.0102(6) 0.0130(6) -0.0221(6) C5 0.0463(7) 0.0390(7) 0.0472(7) -0.0002(5) 0.0229(6) -0.0160(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 O11 C11 1.2586(15) . ? O21 C31 1.2514(13) . ? O31 C41 1.2232(16) . ? N11 C41 1.3715(18) . ? N11 C11 1.3985(16) . ? N11 C51 1.4682(17) . ? N21 C41 1.3767(16) . ? N21 C31 1.3962(15) . ? N21 C61 1.4601(18) . ? C11 C21 1.4002(15) . ? C21 C31 1.3959(16) . ? C21 C22 1.5162(15) . ? C51 H511 0.97(3) . ? C51 H521 0.90(3) . ? C51 H531 1.00(4) . ? C61 H611 0.96(3) . ? C61 H621 0.89(3) . ? C61 H631 0.95(3) . ? O12 C12 1.2078(16) . ? O22 C32 1.2047(15) . ? O32 C42 1.2070(15) . ? O42 C22 1.4123(14) . ? O42 H42 0.87(2) . ? N12 C12 1.3697(15) . ? N12 C42 1.3925(16) . ? N12 C52 1.4650(16) . ? N22 C32 1.3712(15) . ? N22 C42 1.3813(16) . ? N22 C62 1.4708(16) . ? C12 C22 1.5273(16) . ? C22 C32 1.5392(16) . ? C52 H512 1.00(2) . ? C52 H522 0.95(3) . ? C52 H532 0.90(2) . ? C62 H612 0.91(3) . ? C62 H622 1.00(3) . ? C62 H632 0.89(3) . ? N1 C4 1.342(2) . ? N1 C3 1.343(2) . ? N1 H1 0.91(2) . ? N2 C1 1.3304(17) . ? N2 H21 0.90(2) . ? N2 H22 0.93(3) . ? C1 C5 1.4069(19) . ? C1 C2 1.4122(18) . ? C2 C3 1.350(2) . ? C2 H2 0.961(18) . ? C3 H3 0.98(2) . ? C4 C5 1.353(2) . ? C4 H4 0.920(19) . ? C5 H5 0.94(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C41 N11 C11 123.99(10) . . ? C41 N11 C51 117.88(13) . . ? C11 N11 C51 118.11(13) . . ? C41 N21 C31 123.62(10) . . ? C41 N21 C61 118.30(11) . . ? C31 N21 C61 117.90(11) . . ? O11 C11 N11 117.60(10) . . ? O11 C11 C21 125.35(11) . . ? N11 C11 C21 117.04(10) . . ? C31 C21 C11 120.82(10) . . ? C31 C21 C22 118.38(9) . . ? C11 C21 C22 120.75(10) . . ? O21 C31 C21 123.69(10) . . ? O21 C31 N21 118.63(10) . . ? C21 C31 N21 117.66(10) . . ? O31 C41 N11 122.10(12) . . ? O31 C41 N21 121.62(13) . . ? N11 C41 N21 116.28(10) . . ? N11 C51 H511 109.1(19) . . ? N11 C51 H521 110.5(18) . . ? H511 C51 H521 123(3) . . ? N11 C51 H531 110(2) . . ? H511 C51 H531 93(3) . . ? H521 C51 H531 109(3) . . ? N21 C61 H611 109.2(15) . . ? N21 C61 H621 110.8(19) . . ? H611 C61 H621 110(2) . . ? N21 C61 H631 108.7(18) . . ? H611 C61 H631 112(2) . . ? H621 C61 H631 106(3) . . ? C22 O42 H42 103.0(12) . . ? C12 N12 C42 125.16(10) . . ? C12 N12 C52 118.17(11) . . ? C42 N12 C52 116.36(10) . . ? C32 N22 C42 124.79(10) . . ? C32 N22 C62 117.64(11) . . ? C42 N22 C62 117.55(11) . . ? O12 C12 N12 121.78(11) . . ? O12 C12 C22 120.24(11) . . ? N12 C12 C22 117.98(10) . . ? O42 C22 C21 112.48(9) . . ? O42 C22 C12 106.95(9) . . ? C21 C22 C12 109.61(9) . . ? O42 C22 C32 103.56(10) . . ? C21 C22 C32 109.55(9) . . ? C12 C22 C32 114.61(9) . . ? O22 C32 N22 121.26(11) . . ? O22 C32 C22 120.35(11) . . ? N22 C32 C22 118.33(10) . . ? O32 C42 N22 121.40(12) . . ? O32 C42 N12 120.51(12) . . ? N22 C42 N12 118.09(10) . . ? N12 C52 H512 110.2(13) . . ? N12 C52 H522 110.8(16) . . ? H512 C52 H522 101(2) . . ? N12 C52 H532 111.6(16) . . ? H512 C52 H532 107(2) . . ? H522 C52 H532 116(2) . . ? N22 C62 H612 108.3(15) . . ? N22 C62 H622 106.5(15) . . ? H612 C62 H622 109(2) . . ? N22 C62 H632 111.9(18) . . ? H612 C62 H632 115(2) . . ? H622 C62 H632 105(2) . . ? C4 N1 C3 120.57(12) . . ? C4 N1 H1 122.8(14) . . ? C3 N1 H1 116.6(14) . . ? C1 N2 H21 117.1(15) . . ? C1 N2 H22 117.7(15) . . ? H21 N2 H22 125(2) . . ? N2 C1 C5 121.55(13) . . ? N2 C1 C2 121.34(13) . . ? C5 C1 C2 117.11(12) . . ? C3 C2 C1 119.81(13) . . ? C3 C2 H2 119.7(11) . . ? C1 C2 H2 120.5(11) . . ? N1 C3 C2 121.34(12) . . ? N1 C3 H3 117.4(12) . . ? C2 C3 H3 121.2(12) . . ? N1 C4 C5 121.17(13) . . ? N1 C4 H4 114.8(12) . . ? C5 C4 H4 123.9(12) . . ? C4 C5 C1 119.98(13) . . ? C4 C5 H5 117.9(12) . . ? C1 C5 H5 122.0(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.256 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.060 #===END