# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/452 data_ah9609 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H12 N4 O2' _chemical_formula_weight 196.22 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.033(2) _cell_length_b 12.7680(10) _cell_length_c 6.244(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 959.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method ? _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device AFC5R _diffrn_measurement_method 'omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1409 _diffrn_reflns_av_R_equivalents 0.0135 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1385 _reflns_number_observed 929 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0713P)^2^+0.3076P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 5.22(356) _refine_ls_number_reflns 1380 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_obs 0.0527 _refine_ls_wR_factor_all 0.1892 _refine_ls_wR_factor_obs 0.1309 _refine_ls_goodness_of_fit_all 1.043 _refine_ls_goodness_of_fit_obs 1.079 _refine_ls_restrained_S_all 1.251 _refine_ls_restrained_S_obs 1.079 _refine_ls_shift/esd_max 0.184 _refine_ls_shift/esd_mean 0.021 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.7895(2) 0.9525(2) 1.2276(4) 0.0462(8) Uani 1 d . . H1A H 0.7726(2) 1.0048(2) 1.2964(4) 0.069 Uiso 1 calc R . N1 N 0.7618(3) 0.8265(2) 0.8475(5) 0.0381(8) Uani 1 d . . H1B H 0.7493(3) 0.8908(2) 0.8141(5) 0.046 Uiso 1 calc R . C1 C 0.6920(4) 0.8914(3) 1.1867(7) 0.0407(10) Uani 1 d . . H1C H 0.6386(4) 0.9332(3) 1.1074(7) 0.049 Uiso 1 calc R . H1D H 0.6581(4) 0.8714(3) 1.3216(7) 0.049 Uiso 1 calc R . O2 O 0.8554(2) 0.8066(2) 0.5372(5) 0.0446(8) Uani 1 d . . N2 N 0.9245(4) 0.6053(3) 0.6623(7) 0.0532(11) Uani 1 d . . C2 C 0.7211(3) 0.7924(3) 1.0574(6) 0.0377(9) Uani 1 d . . H2B H 0.7826(3) 0.7572(3) 1.1309(6) 0.045 Uiso 1 calc R . N3 N 0.9403(3) 0.6071(3) 0.4670(8) 0.0503(10) Uani 1 d . . C3 C 0.6224(4) 0.7188(3) 1.0599(7) 0.0418(10) Uani 1 d . . H3A H 0.5881(4) 0.7116(3) 1.1926(7) 0.050 Uiso 1 calc R . N4 N 0.9655(4) 0.6003(4) 0.2930(9) 0.0724(14) Uani 1 d . . C4 C 0.5770(4) 0.6630(3) 0.9045(7) 0.0425(10) Uani 1 d . . H4B H 0.5172(4) 0.6214(3) 0.9452(7) 0.051 Uiso 1 calc R . C5 C 0.6082(3) 0.6573(4) 0.6699(7) 0.0435(10) Uani 1 d . . H5A H 0.6123(3) 0.7280(4) 0.6135(7) 0.052 Uiso 1 calc R . H5B H 0.5495(3) 0.6211(4) 0.5935(7) 0.052 Uiso 1 calc R . C6 C 0.7182(3) 0.6020(3) 0.6236(7) 0.0416(10) Uani 1 d . . H6A H 0.7313(3) 0.6031(3) 0.4703(7) 0.050 Uiso 1 calc R . H6B H 0.7118(3) 0.5293(3) 0.6670(7) 0.050 Uiso 1 calc R . C7 C 0.8194(3) 0.6510(3) 0.7378(7) 0.0377(9) Uani 1 d . . H7A H 0.8127(3) 0.6372(3) 0.8917(7) 0.045 Uiso 1 calc R . C8 C 0.8156(3) 0.7696(3) 0.7030(6) 0.0328(9) Uani 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 0.056(2) 0.0319(13) 0.051(2) -0.0105(13) 0.001(2) -0.0042(13) N1 0.049(2) 0.0240(14) 0.041(2) 0.0032(15) 0.002(2) -0.0035(15) C1 0.044(2) 0.036(2) 0.042(2) -0.002(2) 0.003(2) 0.001(2) O2 0.046(2) 0.0411(15) 0.047(2) 0.0029(14) 0.010(2) -0.0004(13) N2 0.047(2) 0.053(2) 0.059(3) -0.012(2) -0.008(2) 0.014(2) C2 0.046(2) 0.031(2) 0.036(2) 0.001(2) 0.000(2) 0.001(2) N3 0.042(2) 0.036(2) 0.072(3) -0.013(2) 0.005(2) -0.001(2) C3 0.052(2) 0.034(2) 0.039(2) 0.004(2) 0.005(2) -0.007(2) N4 0.077(3) 0.056(3) 0.084(4) -0.014(3) 0.027(3) -0.011(2) C4 0.039(2) 0.037(2) 0.051(3) 0.006(2) 0.003(2) -0.003(2) C5 0.035(2) 0.046(2) 0.049(3) -0.002(2) -0.008(2) -0.004(2) C6 0.045(2) 0.032(2) 0.048(2) -0.005(2) -0.004(2) -0.003(2) C7 0.039(2) 0.034(2) 0.040(2) -0.001(2) -0.002(2) 0.008(2) C8 0.030(2) 0.032(2) 0.036(2) 0.001(2) -0.001(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.432(5) . ? N1 C8 1.327(5) . ? N1 C2 1.465(5) . ? C1 C2 1.540(5) . ? O2 C8 1.234(5) . ? N2 N3 1.234(6) . ? N2 C7 1.470(5) . ? C2 C3 1.514(5) . ? N3 N4 1.132(5) . ? C3 C4 1.322(6) . ? C4 C5 1.514(6) . ? C5 C6 1.527(6) . ? C6 C7 1.544(5) . ? C7 C8 1.531(5) . ? 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 C8 N1 C2 127.5(3) . . ? O1 C1 C2 110.7(3) . . ? N3 N2 C7 116.2(4) . . ? N1 C2 C3 117.1(3) . . ? N1 C2 C1 107.5(3) . . ? C3 C2 C1 109.0(3) . . ? N4 N3 N2 171.3(6) . . ? C4 C3 C2 130.6(4) . . ? C3 C4 C5 129.3(4) . . ? C4 C5 C6 114.9(4) . . ? C5 C6 C7 114.1(3) . . ? N2 C7 C8 111.9(4) . . ? N2 C7 C6 111.7(3) . . ? C8 C7 C6 108.2(3) . . ? O2 C8 N1 123.4(3) . . ? O2 C8 C7 119.1(3) . . ? N1 C8 C7 117.3(3) . . ? _refine_diff_density_max 0.245 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.053 data_ah9601 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H19 N3 O3' _chemical_formula_weight 241.29 _chemical_melting_point ? _chemical_compound_source ? 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.871(3) _cell_length_b 18.478(5) _cell_length_c 9.682(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2660.5(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method ? _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type 'empirical (4 psi scans)' _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.987 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device AFC5R _diffrn_measurement_method 'omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4% _diffrn_reflns_number 1994 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1319 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 22.50 _reflns_number_total 1994 _reflns_number_observed 1031 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 12 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.6063P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 6.04(489) _refine_ls_number_reflns 1982 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2018 _refine_ls_R_factor_obs 0.0592 _refine_ls_wR_factor_all 0.2824 _refine_ls_wR_factor_obs 0.1399 _refine_ls_goodness_of_fit_all 1.080 _refine_ls_goodness_of_fit_obs 1.199 _refine_ls_restrained_S_all 1.597 _refine_ls_restrained_S_obs 1.199 _refine_ls_shift/esd_max 0.123 _refine_ls_shift/esd_mean 0.008 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.0210(6) 0.2530(5) 0.3382(10) 0.081(3) Uani 1 d . . H1A H 0.0574(6) 0.2453(5) 0.4057(10) 0.097 Uiso 1 calc R . O1 O -0.0423(6) 0.3379(4) 0.2006(9) 0.120(3) Uani 1 d . . C1 C -0.0217(9) 0.1910(7) 0.2717(14) 0.109(5) Uani 1 d . . H1B H -0.0019(9) 0.1472(7) 0.3154(14) 0.163 Uiso 1 calc R . H1C H -0.0055(9) 0.1900(7) 0.1757(14) 0.163 Uiso 1 calc R . H1D H -0.0859(9) 0.1951(7) 0.2801(14) 0.163 Uiso 1 calc R . O2 O -0.0564(5) 0.5469(3) 0.4773(7) 0.070(2) Uani 1 d . . N2 N -0.0042(5) 0.4424(5) 0.3901(8) 0.067(2) Uani 1 d . . H2A H -0.0455(5) 0.4449(5) 0.3281(8) 0.080 Uiso 1 calc R . C2 C 0.0058(8) 0.3211(6) 0.2986(12) 0.070(3) Uani 1 d . . O3 O -0.0477(4) 0.4145(3) 0.7481(7) 0.071(2) Uani 1 d . . N3 N 0.0337(5) 0.5156(4) 0.7279(8) 0.056(2) Uani 1 d . . H3A H 0.0496(5) 0.5566(4) 0.7621(8) 0.068 Uiso 1 calc R . C3 C 0.0559(7) 0.3802(5) 0.3806(11) 0.066(3) Uani 1 d . . H3B H 0.0654(7) 0.3619(5) 0.4745(11) 0.079 Uiso 1 calc R . C4 C 0.1469(8) 0.3925(7) 0.3168(13) 0.095(4) Uani 1 d . . H4A H 0.1385(8) 0.4164(7) 0.2285(13) 0.113 Uiso 1 calc R . H4B H 0.1741(8) 0.3458(7) 0.2985(13) 0.113 Uiso 1 calc R . C5 C 0.2140(8) 0.4380(9) 0.4036(14) 0.112(5) Uani 1 d . . H5A H 0.2161(8) 0.4183(9) 0.4965(14) 0.135 Uiso 1 calc R . H5B H 0.2735(8) 0.4329(9) 0.3639(14) 0.135 Uiso 1 calc R . C6 C 0.1918(9) 0.5168(7) 0.4125(13) 0.103(4) Uani 1 d . . H6A H 0.1507(9) 0.5290(7) 0.3382(13) 0.124 Uiso 1 calc R . H6B H 0.2464(9) 0.5446(7) 0.3988(13) 0.124 Uiso 1 calc R . C7 C 0.1489(7) 0.5395(6) 0.5508(11) 0.076(3) Uani 1 d . . H7A H 0.1294(7) 0.5895(6) 0.5438(11) 0.091 Uiso 1 calc R . H7B H 0.1943(7) 0.5371(6) 0.6226(11) 0.091 Uiso 1 calc R . C8 C 0.0683(6) 0.4926(5) 0.5937(10) 0.053(3) Uani 1 d . . H8A H 0.0884(6) 0.4422(5) 0.6013(10) 0.064 Uiso 1 calc R . C9 C -0.0033(7) 0.4969(5) 0.4839(9) 0.054(3) Uani 1 d . . C10 C -0.0222(7) 0.4731(5) 0.7966(10) 0.051(3) Uani 1 d . . C11 C -0.0528(7) 0.4993(5) 0.9361(10) 0.074(3) Uani 1 d . . H11A H -0.0259(7) 0.5455(5) 0.9552(10) 0.111 Uiso 1 calc R . H11B H -0.0349(7) 0.4652(5) 1.0057(10) 0.111 Uiso 1 calc R . H11C H -0.1171(7) 0.5041(5) 0.9365(10) 0.111 Uiso 1 calc R . N4 N 0.2427(5) -0.0034(4) 0.8695(7) 0.057(2) Uani 1 d . . H4C H 0.2143(5) 0.0012(4) 0.9464(7) 0.069 Uiso 1 calc R . N5 N 0.1988(5) 0.1705(4) 0.7200(7) 0.051(2) Uani 1 d . . H5C H 0.2409(5) 0.1657(4) 0.6598(7) 0.061 Uiso 1 calc R . N6 N -0.0145(5) 0.2629(4) 0.7357(10) 0.072(3) Uani 1 d . . H6C H -0.0292(5) 0.3076(4) 0.7451(10) 0.086 Uiso 1 calc R . O4 O 0.2894(4) 0.0516(3) 0.6774(7) 0.065(2) Uani 1 d . . O5 O 0.1404(5) 0.2558(4) 0.5807(7) 0.075(2) Uani 1 d . . O6 O -0.0543(5) 0.1553(4) 0.6466(8) 0.085(2) Uani 1 d . . C12 C 0.2817(7) -0.0746(5) 0.8350(10) 0.073(3) Uani 1 d . . H12A H 0.2693(7) -0.1081(5) 0.9082(10) 0.109 Uiso 1 calc R . H12B H 0.3456(7) -0.0698(5) 0.8237(10) 0.109 Uiso 1 calc R . H12C H 0.2556(7) -0.0920(5) 0.7507(10) 0.109 Uiso 1 calc R . C13 C 0.2492(6) 0.0534(5) 0.7878(10) 0.051(2) Uani 1 d . . C14 C 0.2057(6) 0.1228(4) 0.8381(8) 0.048(2) Uani 1 d . . H14A H 0.1450(6) 0.1117(4) 0.8714(8) 0.058 Uiso 1 calc R . C15 C 0.2598(7) 0.1552(5) 0.9563(10) 0.071(3) Uani 1 d . . H15A H 0.3180(7) 0.1701(5) 0.9211(10) 0.086 Uiso 1 calc R . H15B H 0.2700(7) 0.1179(5) 1.0250(10) 0.086 Uiso 1 calc R . C16 C 0.2144(13) 0.2220(8) 1.0289(16) 0.161(8) Uani 1 d . . H16A H 0.1593(13) 0.2042(8) 1.0703(16) 0.193 Uiso 1 calc R . H16B H 0.2536(13) 0.2355(8) 1.1047(16) 0.193 Uiso 1 calc R . C17 C 0.1936(12) 0.2819(9) 0.9651(20) 0.164(8) Uani 1 d . . H17A H 0.2379(12) 0.2881(9) 0.8926(20) 0.197 Uiso 1 calc R . H17B H 0.2034(12) 0.3208(9) 1.0307(20) 0.197 Uiso 1 calc R . C18 C 0.1020(7) 0.2962(6) 0.8988(13) 0.088(4) Uani 1 d . . H18A H 0.0579(7) 0.3020(6) 0.9719(13) 0.106 Uiso 1 calc R . H18B H 0.1052(7) 0.3416(6) 0.8489(13) 0.106 Uiso 1 calc R . C19 C 0.0685(6) 0.2378(5) 0.8001(11) 0.063(3) Uani 1 d . . H19A H 0.0563(6) 0.1934(5) 0.8524(11) 0.076 Uiso 1 calc R . C20 C 0.1364(7) 0.2217(5) 0.6890(12) 0.057(3) Uani 1 d . . C21 C -0.0687(7) 0.2199(6) 0.6632(11) 0.063(3) Uani 1 d . . C22 C -0.1476(6) 0.2564(6) 0.5916(12) 0.082(3) Uani 1 d . . H22A H -0.1488(6) 0.3068(6) 0.6158(12) 0.123 Uiso 1 calc R . H22B H -0.2027(6) 0.2339(6) 0.6205(12) 0.123 Uiso 1 calc R . H22C H -0.1412(6) 0.2516(6) 0.4934(12) 0.123 Uiso 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 N1 0.094(7) 0.071(6) 0.079(6) -0.012(6) -0.005(6) 0.020(6) O1 0.160(8) 0.097(6) 0.104(6) -0.029(6) -0.078(7) 0.043(6) C1 0.118(11) 0.090(9) 0.119(11) -0.019(9) -0.012(10) -0.007(8) O2 0.073(5) 0.057(4) 0.080(5) -0.015(4) -0.003(4) 0.020(4) N2 0.061(5) 0.075(6) 0.064(5) -0.020(5) -0.017(5) 0.020(5) C2 0.081(8) 0.066(8) 0.064(8) -0.027(6) -0.014(7) 0.019(7) O3 0.079(5) 0.045(4) 0.089(5) -0.007(4) -0.003(5) 0.002(4) N3 0.061(5) 0.054(5) 0.054(5) -0.016(4) 0.006(5) -0.012(4) C3 0.070(7) 0.068(7) 0.059(7) -0.003(6) -0.013(7) 0.029(6) C4 0.077(8) 0.114(10) 0.093(9) -0.009(8) 0.022(8) 0.005(8) C5 0.062(8) 0.159(14) 0.117(11) -0.024(11) 0.019(8) -0.016(10) C6 0.091(9) 0.116(11) 0.103(10) -0.008(9) 0.039(9) -0.022(8) C7 0.065(7) 0.088(8) 0.075(7) -0.016(7) 0.010(6) -0.019(6) C8 0.047(6) 0.055(6) 0.058(7) -0.009(5) 0.004(6) -0.003(5) C9 0.057(7) 0.055(6) 0.051(7) -0.002(6) 0.000(6) 0.001(6) C10 0.057(7) 0.042(6) 0.054(6) -0.010(5) -0.002(6) 0.001(5) C11 0.086(8) 0.075(7) 0.062(7) -0.003(6) 0.019(6) 0.002(7) N4 0.068(5) 0.058(5) 0.045(5) 0.000(4) 0.003(4) -0.003(4) N5 0.051(5) 0.057(5) 0.045(5) 0.008(4) 0.011(4) 0.008(4) N6 0.061(6) 0.050(5) 0.105(7) 0.001(5) -0.002(6) 0.006(5) O4 0.072(5) 0.065(4) 0.060(4) 0.003(4) 0.017(4) 0.013(4) O5 0.085(5) 0.080(5) 0.061(5) 0.026(4) 0.007(4) 0.018(5) O6 0.102(6) 0.044(4) 0.108(6) 0.011(4) -0.011(5) 0.007(4) C12 0.106(9) 0.048(6) 0.065(7) -0.001(5) -0.018(7) -0.003(6) C13 0.056(6) 0.064(7) 0.033(5) 0.006(6) 0.001(5) -0.013(6) C14 0.064(6) 0.046(6) 0.034(5) -0.004(5) 0.010(5) 0.006(5) C15 0.099(8) 0.066(7) 0.049(6) 0.004(6) -0.013(6) 0.011(6) C16 0.267(22) 0.094(11) 0.122(12) -0.050(10) -0.112(15) 0.047(13) C17 0.214(18) 0.107(13) 0.173(17) -0.062(12) -0.102(15) 0.049(12) C18 0.089(8) 0.091(9) 0.084(8) -0.031(7) -0.020(8) 0.017(7) C19 0.057(6) 0.057(6) 0.075(7) -0.003(6) 0.001(6) 0.020(6) C20 0.055(6) 0.043(6) 0.072(8) -0.003(6) -0.007(7) 0.004(5) C21 0.060(7) 0.052(7) 0.076(8) 0.001(6) 0.000(6) 0.005(6) C22 0.053(6) 0.076(7) 0.116(9) 0.005(8) -0.004(7) 0.018(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 N1 C2 1.336(13) . ? N1 C1 1.459(13) . ? O1 C2 1.228(12) . ? O2 C9 1.216(10) . ? N2 C9 1.355(11) . ? N2 C3 1.459(11) . ? C2 C3 1.541(14) . ? O3 C10 1.240(10) . ? N3 C10 1.323(10) . ? N3 C8 1.461(11) . ? C3 C4 1.506(14) . ? C4 C5 1.552(15) . ? C5 C6 1.50(2) . ? C6 C7 1.541(15) . ? C7 C8 1.538(12) . ? C8 C9 1.507(12) . ? C10 C11 1.506(13) . ? N4 C13 1.318(11) . ? N4 C12 1.475(11) . ? N5 C20 1.357(10) . ? N5 C14 1.448(10) . ? N6 C21 1.332(12) . ? N6 C19 1.458(12) . ? O4 C13 1.226(10) . ? O5 C20 1.226(11) . ? O6 C21 1.223(10) . ? C13 C14 1.516(12) . ? C14 C15 1.522(12) . ? C15 C16 1.57(2) . ? C16 C17 1.31(2) . ? C17 C18 1.53(2) . ? C18 C19 1.525(13) . ? C19 C20 1.505(13) . ? C21 C22 1.521(13) . ? 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 C2 N1 C1 122.6(10) . . ? C9 N2 C3 128.4(8) . . ? O1 C2 N1 123.9(11) . . ? O1 C2 C3 120.0(10) . . ? N1 C2 C3 116.0(10) . . ? C10 N3 C8 119.7(7) . . ? N2 C3 C4 117.2(9) . . ? N2 C3 C2 107.2(8) . . ? C4 C3 C2 109.3(9) . . ? C3 C4 C5 115.9(10) . . ? C6 C5 C4 114.6(12) . . ? C5 C6 C7 114.0(11) . . ? C6 C7 C8 113.8(9) . . ? N3 C8 C9 111.3(7) . . ? N3 C8 C7 110.5(8) . . ? C9 C8 C7 109.3(8) . . ? O2 C9 N2 121.5(9) . . ? O2 C9 C8 122.3(8) . . ? N2 C9 C8 116.1(8) . . ? O3 C10 N3 121.3(9) . . ? O3 C10 C11 122.0(10) . . ? N3 C10 C11 116.7(8) . . ? C13 N4 C12 123.0(8) . . ? C20 N5 C14 130.3(8) . . ? C21 N6 C19 123.3(8) . . ? O4 C13 N4 122.5(9) . . ? O4 C13 C14 120.7(8) . . ? N4 C13 C14 116.7(8) . . ? N5 C14 C13 107.0(7) . . ? N5 C14 C15 113.0(7) . . ? C13 C14 C15 110.4(7) . . ? C14 C15 C16 114.7(9) . . ? C17 C16 C15 123.7(14) . . ? C16 C17 C18 123.8(16) . . ? C19 C18 C17 115.6(10) . . ? N6 C19 C20 109.0(8) . . ? N6 C19 C18 108.6(8) . . ? C20 C19 C18 111.6(8) . . ? O5 C20 N5 120.9(9) . . ? O5 C20 C19 122.8(9) . . ? N5 C20 C19 116.0(9) . . ? O6 C21 N6 123.1(10) . . ? O6 C21 C22 120.5(10) . . ? N6 C21 C22 116.3(9) . . ? _refine_diff_density_max 0.243 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.047