# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 207 loop_ _publ_author_name 'J. Szczepkowska-Stolcman' 'A.Katrusiak' 'H.Wojtowicz-Rajchel' 'K. Golankiewicz' _publ_contact_author_name 'Dr Krzysztof Golankiewicz' _publ_contact_author_address ; Faculty of Chemistry Adam Mickiewicz University Grunwaldzka 6 Poznan 60 780 POLAND ; _publ_contact_author_email 'GOLAN@MAIN.AMU.EDU.PL' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; Reactions of n- Electron Rich 1,2,4-Triazines with Organolithium Nucleophiles. ; data_compound_7a _database_code_CSD 181716 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H13 N3 O S' _chemical_formula_weight 199.27 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 8.877(2) _cell_length_b 5.8520(10) _cell_length_c 19.624(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.84(3) _cell_angle_gamma 90.00 _cell_volume 997.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.290 _exptl_absorpt_correction_type ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8710 _diffrn_reflns_av_R_equivalents 0.0924 _diffrn_reflns_av_sigmaI/netI 0.1015 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 29.98 _reflns_number_total 2666 _reflns_number_gt 1414 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0100P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2666 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1577 _refine_ls_R_factor_gt 0.0665 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.389 _refine_ls_restrained_S_all 1.389 _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 N1 N 0.8057(5) 0.4434(7) 0.8563(2) 0.0412(11) Uani 1 1 d . . . C2 C 0.9553(6) 0.3845(9) 0.8625(3) 0.0388(12) Uani 1 1 d . . . S2 S 0.97108(17) 0.1442(3) 0.81087(8) 0.0532(5) Uani 1 1 d . . . C7 C 1.1756(7) 0.1013(13) 0.8280(4) 0.0675(19) Uani 1 1 d G . . H1 H 1.1981 -0.0259 0.8009 0.10(3) Uiso 1 1 d G . . H2 H 1.2202 0.0754 0.8762 0.11(3) Uiso 1 1 d G . . H3 H 1.2180 0.2383 0.8126 0.08(2) Uiso 1 1 d G . . N3 N 1.0791(5) 0.4792(8) 0.9006(2) 0.0444(11) Uani 1 1 d . . . C4 C 1.0563(6) 0.6638(10) 0.9397(3) 0.0428(13) Uani 1 1 d . . . O4 O 1.1604(4) 0.7708(7) 0.9778(2) 0.0626(12) Uani 1 1 d . . . C5 N 0.8930(7) 0.7348(10) 0.9353(3) 0.0681(16) Uani 1 1 d . . . H5 H 0.861(6) 0.902(9) 0.977(3) 0.054(15) Uiso 1 1 d . . . N6 C 0.7834(4) 0.6214(7) 0.8958(2) 0.0206(9) Uani 1 1 d . . . C3 C 0.6151(6) 0.6862(9) 0.8884(3) 0.0413(13) Uani 1 1 d . . . C8 C 0.5960(7) 0.8443(15) 0.9469(4) 0.072(2) Uani 1 1 d G . . H81 H 0.6488 0.9874 0.9466 0.12(3) Uiso 1 1 d G . . H82 H 0.6345 0.7662 0.9899 0.08(2) Uiso 1 1 d G . . H83 H 0.4877 0.8719 0.9421 0.10(2) Uiso 1 1 d G . . C9 C 0.5263(8) 0.4713(11) 0.8909(5) 0.069(2) Uani 1 1 d G . . H91 H 0.5309 0.3816 0.8505 0.08(2) Uiso 1 1 d G . . H92 H 0.4209 0.5057 0.8916 0.09(2) Uiso 1 1 d G . . H93 H 0.5711 0.3869 0.9321 0.10(3) Uiso 1 1 d G . . C10 C 0.5722(8) 0.8054(15) 0.8180(4) 0.074(2) Uani 1 1 d G . . H101 H 0.6314 0.9420 0.8166 0.13(3) Uiso 1 1 d G . . H102 H 0.4655 0.8444 0.8130 0.11(3) Uiso 1 1 d G . . H103 H 0.5849 0.7057 0.7808 0.10(3) Uiso 1 1 d G . . 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 N1 0.039(2) 0.039(2) 0.046(3) -0.006(2) 0.007(2) 0.002(2) C2 0.037(3) 0.044(3) 0.037(3) -0.001(2) 0.009(2) 0.001(3) S2 0.0444(8) 0.0550(9) 0.0602(10) -0.0142(8) 0.0109(7) 0.0029(8) C7 0.045(4) 0.075(5) 0.085(5) -0.021(4) 0.019(4) 0.006(4) N3 0.036(2) 0.049(3) 0.046(3) -0.007(2) 0.002(2) 0.000(2) C4 0.038(3) 0.046(3) 0.042(3) 0.000(3) 0.004(2) -0.002(3) O4 0.045(2) 0.063(3) 0.071(3) -0.016(2) -0.008(2) -0.006(2) C5 0.074(4) 0.066(4) 0.068(4) 0.011(3) 0.024(3) 0.011(3) N6 0.0174(19) 0.020(2) 0.021(2) -0.0061(18) -0.0029(17) -0.0025(17) C3 0.031(3) 0.050(3) 0.041(3) -0.005(3) 0.003(2) 0.002(2) C8 0.043(4) 0.092(6) 0.079(6) -0.043(5) 0.010(4) 0.012(4) C9 0.046(4) 0.058(4) 0.107(6) -0.017(5) 0.025(4) -0.003(3) C10 0.050(4) 0.100(6) 0.069(5) 0.018(5) 0.007(4) 0.024(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N6 1.338(5) . ? N1 C2 1.353(6) . ? C2 N3 1.318(6) . ? C2 S2 1.756(5) . ? S2 C7 1.795(6) . ? N3 C4 1.364(7) . ? C4 O4 1.234(6) . ? C4 C5 1.493(7) . ? C5 N6 1.295(7) . ? N6 C3 1.519(6) . ? C3 C9 1.491(8) . ? C3 C8 1.511(7) . ? C3 C10 1.524(8) . ? 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 N6 N1 C2 113.9(4) . . ? N3 C2 N1 129.3(5) . . ? N3 C2 S2 120.5(4) . . ? N1 C2 S2 110.2(4) . . ? C2 S2 C7 101.6(3) . . ? C2 N3 C4 116.7(5) . . ? O4 C4 N3 124.3(5) . . ? O4 C4 C5 119.5(5) . . ? N3 C4 C5 116.2(5) . . ? N6 C5 C4 119.6(5) . . ? C5 N6 N1 124.3(4) . . ? C5 N6 C3 122.2(4) . . ? N1 N6 C3 113.4(4) . . ? C9 C3 C8 110.4(6) . . ? C9 C3 N6 107.6(4) . . ? C8 C3 N6 110.0(4) . . ? C9 C3 C10 112.4(6) . . ? C8 C3 C10 111.2(6) . . ? N6 C3 C10 105.0(5) . . ? 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 N6 N1 C2 N3 -1.3(8) . . . . ? N6 N1 C2 S2 178.0(3) . . . . ? N3 C2 S2 C7 -0.6(5) . . . . ? N1 C2 S2 C7 -180.0(4) . . . . ? N1 C2 N3 C4 -0.1(8) . . . . ? S2 C2 N3 C4 -179.4(4) . . . . ? C2 N3 C4 O4 -179.8(5) . . . . ? C2 N3 C4 C5 0.7(7) . . . . ? O4 C4 C5 N6 -179.4(5) . . . . ? N3 C4 C5 N6 0.2(7) . . . . ? C4 C5 N6 N1 -1.7(8) . . . . ? C4 C5 N6 C3 -179.3(5) . . . . ? C2 N1 N6 C5 2.2(7) . . . . ? C2 N1 N6 C3 180.0(4) . . . . ? C5 N6 C3 C9 -136.9(6) . . . . ? N1 N6 C3 C9 45.3(6) . . . . ? C5 N6 C3 C8 -16.6(7) . . . . ? N1 N6 C3 C8 165.6(5) . . . . ? C5 N6 C3 C10 103.2(6) . . . . ? N1 N6 C3 C10 -74.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.323 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.084 data_compound_5 _database_code_CSD 181717 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-phenyl-1,2,4-triazin-3-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 N3 O' _chemical_formula_weight 173.18 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 20.708(3) _cell_length_b 6.9640(10) _cell_length_c 12.305(2) _cell_angle_alpha 90.00 _cell_angle_beta 117.01(3) _cell_angle_gamma 90.00 _cell_volume 1581.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 90(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type ? _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 'kuma km4 ccd' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2675 _diffrn_reflns_av_R_equivalents 0.0196 _diffrn_reflns_av_sigmaI/netI 0.0417 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 29.16 _reflns_number_total 1579 _reflns_number_gt 1059 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1579 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0799 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0632 _refine_ls_goodness_of_fit_ref 1.470 _refine_ls_restrained_S_all 1.470 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.06771(9) -0.1396(2) 0.06896(12) 0.0217(4) Uani 1 1 d . . . N2 N 0.05440(8) -0.1165(2) 0.16534(12) 0.0184(4) Uani 1 1 d . . . H2 H 0.0015(12) -0.106(3) 0.1494(16) 0.058(7) Uiso 1 1 d . . . C3 C 0.10635(10) -0.1057(3) 0.28456(15) 0.0187(4) Uani 1 1 d . . . O3 O 0.08833(7) -0.09960(18) 0.36780(10) 0.0255(3) Uani 1 1 d . . . N4 N 0.17825(8) -0.1011(2) 0.30866(12) 0.0182(4) Uani 1 1 d . . . C5 C 0.19304(10) -0.1205(2) 0.21651(15) 0.0167(4) Uani 1 1 d . . . C6 C 0.13594(11) -0.1445(3) 0.09418(16) 0.0197(4) Uani 1 1 d . . . H6 H 0.1459(10) -0.159(2) 0.0246(14) 0.025(5) Uiso 1 1 d . . . C1' C 0.26946(10) -0.1185(2) 0.24076(14) 0.0160(4) Uani 1 1 d . . . C2' C 0.32372(11) -0.1553(2) 0.35934(16) 0.0194(5) Uani 1 1 d . . . H2' H 0.3077(10) -0.183(2) 0.4185(14) 0.021 Uiso 1 1 d . . . C3' C 0.39587(11) -0.1548(3) 0.38470(17) 0.0226(5) Uani 1 1 d . . . H3' H 0.4338(10) -0.179(2) 0.4684(14) 0.025 Uiso 1 1 d . . . C4' C 0.41563(10) -0.1168(3) 0.29357(17) 0.0245(5) Uani 1 1 d . . . H4' H 0.4673(10) -0.119(2) 0.3140(14) 0.027 Uiso 1 1 d . . . C5' C 0.36255(11) -0.0788(3) 0.17547(17) 0.0230(5) Uani 1 1 d . . . H5' H 0.3785(9) -0.054(2) 0.1121(14) 0.025 Uiso 1 1 d . . . C6' C 0.28993(11) -0.0812(2) 0.14926(16) 0.0201(5) Uani 1 1 d . . . H6' H 0.2520(9) -0.050(2) 0.0659(14) 0.022 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 N1 0.0222(9) 0.0240(9) 0.0198(8) -0.0010(7) 0.0102(7) 0.0012(7) N2 0.0158(8) 0.0243(8) 0.0165(8) -0.0010(7) 0.0085(7) 0.0008(7) C3 0.0205(10) 0.0163(9) 0.0174(9) 0.0004(8) 0.0070(8) -0.0003(8) O3 0.0197(7) 0.0408(8) 0.0186(6) -0.0018(6) 0.0110(6) -0.0003(6) N4 0.0169(8) 0.0187(8) 0.0190(8) 0.0003(7) 0.0081(7) 0.0000(7) C5 0.0190(10) 0.0106(9) 0.0189(9) 0.0010(8) 0.0072(8) 0.0003(8) C6 0.0216(11) 0.0194(10) 0.0186(9) 0.0003(8) 0.0097(9) 0.0025(8) C1' 0.0180(10) 0.0110(9) 0.0183(9) -0.0005(8) 0.0076(8) 0.0017(8) C2' 0.0226(11) 0.0179(10) 0.0211(10) -0.0004(8) 0.0129(9) -0.0005(8) C3' 0.0180(10) 0.0231(11) 0.0238(10) -0.0010(9) 0.0070(9) 0.0012(8) C4' 0.0184(10) 0.0228(10) 0.0345(11) -0.0020(10) 0.0139(10) 0.0003(9) C5' 0.0269(11) 0.0198(10) 0.0287(11) -0.0010(9) 0.0182(10) -0.0001(8) C6' 0.0232(11) 0.0167(10) 0.0203(9) 0.0001(8) 0.0098(9) 0.0011(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 N1 C6 1.302(2) . ? N1 N2 1.344(2) . ? N2 C3 1.372(2) . ? C3 O3 1.240(2) . ? C3 N4 1.380(2) . ? N4 C5 1.309(2) . ? C5 C6 1.440(2) . ? C5 C1' 1.471(2) . ? C1' C6' 1.396(3) . ? C1' C2' 1.403(2) . ? C2' C3' 1.381(3) . ? C3' C4' 1.383(3) . ? C4' C5' 1.392(3) . ? C5' C6' 1.388(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 C6 N1 N2 115.35(15) . . ? N1 N2 C3 125.10(17) . . ? O3 C3 N2 120.09(18) . . ? O3 C3 N4 121.44(15) . . ? N2 C3 N4 118.46(17) . . ? C5 N4 C3 117.74(15) . . ? N4 C5 C6 120.88(18) . . ? N4 C5 C1' 118.46(14) . . ? C6 C5 C1' 120.66(16) . . ? N1 C6 C5 122.20(19) . . ? C6' C1' C2' 118.67(18) . . ? C6' C1' C5 122.06(15) . . ? C2' C1' C5 119.27(16) . . ? C3' C2' C1' 120.53(18) . . ? C2' C3' C4' 120.37(17) . . ? C3' C4' C5' 119.92(19) . . ? C6' C5' C4' 119.92(19) . . ? C5' C6' C1' 120.58(17) . . ? 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 C6 N1 N2 C3 -2.6(3) . . . . ? N1 N2 C3 O3 -174.24(16) . . . . ? N1 N2 C3 N4 6.0(3) . . . . ? O3 C3 N4 C5 175.70(17) . . . . ? N2 C3 N4 C5 -4.6(3) . . . . ? C3 N4 C5 C6 0.4(3) . . . . ? C3 N4 C5 C1' -179.20(16) . . . . ? N2 N1 C6 C5 -1.9(3) . . . . ? N4 C5 C6 N1 3.0(3) . . . . ? C1' C5 C6 N1 -177.34(18) . . . . ? N4 C5 C1' C6' -160.61(15) . . . . ? C6 C5 C1' C6' 19.7(3) . . . . ? N4 C5 C1' C2' 19.5(3) . . . . ? C6 C5 C1' C2' -160.19(15) . . . . ? C6' C1' C2' C3' -0.1(3) . . . . ? C5 C1' C2' C3' 179.84(17) . . . . ? C1' C2' C3' C4' 0.4(3) . . . . ? C2' C3' C4' C5' 0.0(3) . . . . ? C3' C4' C5' C6' -0.7(3) . . . . ? C4' C5' C6' C1' 1.0(3) . . . . ? C2' C1' C6' C5' -0.6(3) . . . . ? C5 C1' C6' C5' 179.44(18) . . . . ? _diffrn_measured_fraction_theta_max 0.739 _diffrn_reflns_theta_full 29.16 _diffrn_measured_fraction_theta_full 0.739 _refine_diff_density_max 0.288 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.046