# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Davies, R Gareth' 'Gibson, Vernon C.' 'Hursthouse, M.' 'Light, Mark E.' 'Marshall, Edward L.' 'North, Michael' 'Robson, David A.' 'Thompson, Ian' 'White, Andrew J. P.' 'WIlliams, David J.' 'Williams, Paul J.' _publ_contact_author_name 'Dr Michael North' _publ_contact_author_address ; Chemistry King's College London Strand london WC2R 2LS UNITED KINGDOM ; _publ_contact_author_email 'MICHAEL.NORTH@KCL.AC.UK' _publ_section_title ; Synthesis of Nucleic-Acid Base containing Norbornene derivatives as Monomers for Ring-Opening-Metathesis-Polymerization ; data_VG9804 _database_code_CSD 168679 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H20 N5 O6 F3' _chemical_formula_weight 471.40 _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 13.8726(9) _cell_length_b 30.229(3) _cell_length_c 9.8793(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4143.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 10.57 _cell_measurement_theta_max 27.92 _exptl_crystal_description 'platy needles' _exptl_crystal_colour Clear _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_method ? _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 1.140 _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 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3437 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0500 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 63.98 _reflns_number_total 3437 _reflns_number_observed 2258 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 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^)+(0.0911P)^2^+2.5485P] 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 SHELXL _refine_ls_extinction_coef 0.00052(14) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3436 _refine_ls_number_parameters 327 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1002 _refine_ls_R_factor_obs 0.0638 _refine_ls_wR_factor_all 0.1932 _refine_ls_wR_factor_obs 0.1602 _refine_ls_goodness_of_fit_all 1.035 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_restrained_S_all 1.036 _refine_ls_restrained_S_obs 1.083 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.6296(3) 0.6568(2) -1.2005(4) 0.0570(10) Uani 1 d . . H1A H 0.6629(3) 0.6283(2) -1.2098(4) 0.068 Uiso 1 calc R . C2 C 0.6523(3) 0.6825(2) -1.0755(5) 0.0730(14) Uani 1 d . . H2A H 0.6778(3) 0.6714(2) -0.9953(5) 0.088 Uiso 1 calc R . C3 C 0.6291(4) 0.7245(2) -1.1012(6) 0.080(2) Uani 1 d . . H3A H 0.6354(4) 0.7480(2) -1.0412(6) 0.096 Uiso 1 calc R . C4 C 0.5910(3) 0.7275(2) -1.2430(5) 0.0632(12) Uani 1 d . . H4A H 0.5931(3) 0.7567(2) -1.2856(5) 0.076 Uiso 1 calc R . C5 C 0.4906(3) 0.70336(13) -1.2434(4) 0.0491(9) Uani 1 d . . H5A H 0.4581(3) 0.70611(13) -1.3310(4) 0.059 Uiso 1 calc R . C6 C 0.5172(3) 0.65512(13) -1.2116(4) 0.0432(8) Uani 1 d . . H6A H 0.4965(3) 0.63519(13) -1.2842(4) 0.052 Uiso 1 calc R . C7 C 0.6516(3) 0.6911(2) -1.3099(5) 0.0661(12) Uani 1 d . . H7A H 0.6276(3) 0.6827(2) -1.3984(5) 0.079 Uiso 1 calc R . H7B H 0.7195(3) 0.6986(2) -1.3150(5) 0.079 Uiso 1 calc R . C8 C 0.4660(2) 0.64491(12) -1.0809(4) 0.0405(8) Uani 1 d . . O8 O 0.4677(2) 0.61044(10) -1.0185(3) 0.0548(7) Uani 1 d . . C9 C 0.4265(3) 0.71763(13) -1.1281(4) 0.0502(9) Uani 1 d . . O9 O 0.3894(3) 0.75311(12) -1.1106(4) 0.0828(11) Uani 1 d . . N10 N 0.4169(2) 0.68212(10) -1.0398(3) 0.0417(7) Uani 1 d . . C11 C 0.3685(3) 0.68666(14) -0.9093(4) 0.0470(9) Uani 1 d . . H11A H 0.3811(3) 0.71589(14) -0.8729(4) 0.056 Uiso 1 calc R . H11B H 0.3946(3) 0.66509(14) -0.8465(4) 0.056 Uiso 1 calc R . C12 C 0.2604(3) 0.67996(13) -0.9211(4) 0.0494(9) Uani 1 d . . H12A H 0.2302(3) 0.68680(13) -0.8351(4) 0.059 Uiso 1 calc R . H12B H 0.2348(3) 0.70018(13) -0.9884(4) 0.059 Uiso 1 calc R . N13 N 0.2366(2) 0.63493(12) -0.9593(3) 0.0477(7) Uani 1 d D . H13A H 0.2479(40) 0.6248(16) -1.0435(21) 0.068(14) Uiso 1 d D . C14 C 0.2241(2) 0.60306(13) -0.8680(4) 0.0438(8) Uani 1 d . . O14 O 0.2214(2) 0.60942(10) -0.7455(3) 0.0603(8) Uani 1 d . . C15 C 0.2120(4) 0.55752(15) -0.9300(5) 0.0633(11) Uani 1 d . . H15A H 0.1591(4) 0.55809(15) -0.9940(5) 0.076 Uiso 1 calc R . H15B H 0.2702(4) 0.54974(15) -0.9790(5) 0.076 Uiso 1 calc R . N16 N 0.1931(3) 0.52421(12) -0.8274(4) 0.0543(8) Uani 1 d . . C17 C 0.2712(3) 0.50442(14) -0.7651(4) 0.0512(9) Uani 1 d . . O17 O 0.3539(2) 0.51309(12) -0.7974(4) 0.0729(10) Uani 1 d . . N18 N 0.2502(2) 0.47542(10) -0.6629(3) 0.0469(7) Uani 1 d D . H18A H 0.2986(25) 0.4612(15) -0.6207(48) 0.069(15) Uiso 1 d D . C19 C 0.1592(3) 0.46422(13) -0.6236(4) 0.0471(9) Uani 1 d . . N19 N 0.1485(3) 0.43497(13) -0.5290(4) 0.0607(9) Uani 1 d D . H19A H 0.0919(23) 0.4271(21) -0.4915(61) 0.093(20) Uiso 1 d D . H19B H 0.1987(32) 0.4233(22) -0.4835(65) 0.107(23) Uiso 1 d D . C20 C 0.0818(3) 0.48610(14) -0.6882(5) 0.0569(11) Uani 1 d . . H20A H 0.0185(3) 0.48032(14) -0.6629(5) 0.068 Uiso 1 calc R . C21 C 0.1010(3) 0.51512(15) -0.7860(5) 0.0613(11) Uani 1 d . . H21A H 0.0500(3) 0.52974(15) -0.8277(5) 0.074 Uiso 1 calc R . O31 O 0.4133(2) 0.43023(13) -0.5503(4) 0.0715(9) Uani 1 d . . O32 O 0.3098(2) 0.4074(2) -0.3943(4) 0.0890(12) Uani 1 d . . C33 C 0.3891(3) 0.40907(15) -0.4502(4) 0.0529(9) Uani 1 d . . C34 C 0.4674(3) 0.3820(2) -0.3798(4) 0.0597(11) Uani 1 d . . F35 F 0.5042(6) 0.3492(2) -0.4541(7) 0.088(2) Uani 0.60 d P 1 F36 F 0.5436(4) 0.4079(2) -0.3410(8) 0.086(2) Uani 0.60 d P 1 F37 F 0.4406(5) 0.3650(3) -0.2632(6) 0.104(2) Uani 0.60 d P 1 F35' F 0.5285(9) 0.3671(4) -0.4665(12) 0.084(3) Uiso 0.40 d P 2 F36' F 0.5085(11) 0.4000(4) -0.2892(14) 0.108(4) Uiso 0.40 d P 2 F37' F 0.4305(11) 0.3450(5) -0.3249(16) 0.123(4) Uiso 0.40 d P 2 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 C1 0.036(2) 0.080(3) 0.055(2) -0.001(2) 0.005(2) 0.007(2) C2 0.041(2) 0.120(5) 0.057(3) -0.007(3) -0.006(2) -0.017(3) C3 0.062(3) 0.107(4) 0.070(3) -0.032(3) 0.017(2) -0.040(3) C4 0.067(3) 0.057(2) 0.066(3) -0.001(2) 0.022(2) -0.010(2) C5 0.048(2) 0.054(2) 0.046(2) 0.004(2) 0.006(2) 0.005(2) C6 0.038(2) 0.051(2) 0.041(2) -0.0050(15) -0.0006(14) 0.004(2) C7 0.053(2) 0.084(3) 0.061(3) -0.007(2) 0.022(2) -0.006(2) C8 0.0298(15) 0.047(2) 0.045(2) 0.001(2) -0.0060(14) 0.0028(13) O8 0.0470(14) 0.054(2) 0.064(2) 0.0125(14) 0.0016(13) 0.0070(12) C9 0.047(2) 0.047(2) 0.057(2) 0.002(2) 0.010(2) 0.005(2) O9 0.096(2) 0.053(2) 0.099(3) 0.014(2) 0.044(2) 0.024(2) N10 0.0339(14) 0.051(2) 0.041(2) -0.0022(13) 0.0026(12) 0.0008(12) C11 0.044(2) 0.058(2) 0.039(2) -0.006(2) 0.005(2) -0.002(2) C12 0.043(2) 0.052(2) 0.053(2) 0.005(2) 0.010(2) 0.006(2) N13 0.045(2) 0.060(2) 0.038(2) 0.0034(14) 0.0011(13) -0.0054(15) C14 0.039(2) 0.055(2) 0.037(2) 0.000(2) 0.0015(14) -0.0003(15) O14 0.078(2) 0.065(2) 0.0379(14) -0.0025(12) 0.0036(14) -0.0069(15) C15 0.084(3) 0.057(2) 0.049(2) -0.001(2) -0.007(2) -0.005(2) N16 0.051(2) 0.053(2) 0.060(2) 0.005(2) -0.006(2) -0.0055(15) C17 0.040(2) 0.055(2) 0.059(2) -0.003(2) -0.002(2) -0.010(2) O17 0.042(2) 0.090(2) 0.087(2) 0.014(2) 0.012(2) -0.015(2) N18 0.0292(13) 0.053(2) 0.059(2) 0.0013(15) -0.0028(14) -0.0075(13) C19 0.034(2) 0.047(2) 0.060(2) -0.004(2) 0.001(2) -0.0088(14) N19 0.042(2) 0.066(2) 0.074(2) 0.012(2) 0.003(2) -0.012(2) C20 0.030(2) 0.058(2) 0.083(3) -0.001(2) -0.002(2) -0.003(2) C21 0.044(2) 0.056(2) 0.083(3) -0.005(2) -0.014(2) 0.005(2) O31 0.055(2) 0.093(2) 0.066(2) 0.016(2) 0.002(2) 0.004(2) O32 0.045(2) 0.133(3) 0.089(3) 0.030(3) -0.002(2) -0.002(2) C33 0.045(2) 0.063(2) 0.050(2) -0.001(2) -0.004(2) -0.003(2) C34 0.055(2) 0.075(3) 0.049(2) -0.011(2) -0.008(2) 0.007(2) F35 0.099(5) 0.074(4) 0.091(4) -0.021(3) -0.027(4) 0.040(4) F36 0.040(2) 0.111(4) 0.109(5) -0.008(4) -0.032(3) -0.009(3) F37 0.086(4) 0.170(7) 0.056(3) 0.045(4) 0.002(3) 0.033(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 C1 C2 1.493(7) . ? C1 C7 1.530(7) . ? C1 C6 1.564(5) . ? C2 C3 1.334(9) . ? C3 C4 1.499(8) . ? C4 C7 1.534(6) . ? C4 C5 1.571(6) . ? C5 C9 1.508(5) . ? C5 C6 1.537(5) . ? C6 C8 1.505(5) . ? C8 O8 1.211(5) . ? C8 N10 1.377(5) . ? C9 O9 1.203(5) . ? C9 N10 1.390(5) . ? N10 C11 1.460(5) . ? C11 C12 1.518(5) . ? C12 N13 1.450(5) . ? N13 C14 1.331(5) . ? C14 O14 1.226(5) . ? C14 C15 1.516(6) . ? C15 N16 1.453(6) . ? N16 C21 1.370(6) . ? N16 C17 1.382(5) . ? C17 O17 1.220(5) . ? C17 N18 1.368(5) . ? N18 C19 1.364(5) . ? C19 N19 1.295(6) . ? C19 C20 1.414(6) . ? C20 C21 1.332(7) . ? O31 C33 1.225(6) . ? O32 C33 1.232(6) . ? C33 C34 1.527(6) . ? C34 F36' 1.193(14) . ? C34 F35' 1.286(13) . ? C34 F37 1.315(7) . ? C34 F35 1.334(7) . ? C34 F37' 1.344(15) . ? C34 F36 1.371(7) . ? 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 C1 C7 100.8(4) . . ? C2 C1 C6 106.6(3) . . ? C7 C1 C6 99.9(3) . . ? C3 C2 C1 106.7(5) . . ? C2 C3 C4 108.7(4) . . ? C3 C4 C7 99.6(4) . . ? C3 C4 C5 106.7(4) . . ? C7 C4 C5 98.8(3) . . ? C9 C5 C6 105.0(3) . . ? C9 C5 C4 112.8(3) . . ? C6 C5 C4 103.1(3) . . ? C8 C6 C5 104.9(3) . . ? C8 C6 C1 114.6(3) . . ? C5 C6 C1 102.9(3) . . ? C1 C7 C4 94.2(3) . . ? O8 C8 N10 124.2(3) . . ? O8 C8 C6 127.2(3) . . ? N10 C8 C6 108.6(3) . . ? O9 C9 N10 123.9(4) . . ? O9 C9 C5 128.1(4) . . ? N10 C9 C5 108.1(3) . . ? C8 N10 C9 113.5(3) . . ? C8 N10 C11 124.4(3) . . ? C9 N10 C11 121.8(3) . . ? N10 C11 C12 111.9(3) . . ? N13 C12 C11 111.7(3) . . ? C14 N13 C12 122.2(3) . . ? O14 C14 N13 124.0(4) . . ? O14 C14 C15 122.5(4) . . ? N13 C14 C15 113.4(3) . . ? N16 C15 C14 111.6(4) . . ? C21 N16 C17 120.8(4) . . ? C21 N16 C15 121.1(4) . . ? C17 N16 C15 118.0(4) . . ? O17 C17 N18 122.0(4) . . ? O17 C17 N16 121.8(4) . . ? N18 C17 N16 116.1(3) . . ? C19 N18 C17 124.5(3) . . ? N19 C19 N18 118.8(4) . . ? N19 C19 C20 123.9(4) . . ? N18 C19 C20 117.3(4) . . ? C21 C20 C19 118.9(4) . . ? C20 C21 N16 122.4(4) . . ? O31 C33 O32 128.9(4) . . ? O31 C33 C34 116.9(4) . . ? O32 C33 C34 114.1(4) . . ? F36' C34 F35' 110.1(9) . . ? F37 C34 F35 107.4(6) . . ? F36' C34 F37' 105.0(9) . . ? F35' C34 F37' 103.2(9) . . ? F37 C34 F36 101.3(6) . . ? F35 C34 F36 106.5(6) . . ? F36' C34 C33 115.9(8) . . ? F35' C34 C33 110.7(6) . . ? F37 C34 C33 114.1(4) . . ? F35 C34 C33 114.8(4) . . ? F37' C34 C33 111.0(7) . . ? F36 C34 C33 111.7(5) . . ? _refine_diff_density_max 0.411 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.055 data_VG9747 _database_code_CSD 168680 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H27 N7 O5' _chemical_formula_weight 481.52 _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 '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 37.962(4) _cell_length_b 12.6553(8) _cell_length_c 9.5517(9) _cell_angle_alpha 90.00 _cell_angle_beta 91.589(8) _cell_angle_gamma 90.00 _cell_volume 4587.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 4.68 _cell_measurement_theta_max 27.43 _exptl_crystal_description 'platy needles' _exptl_crystal_colour Clear _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method ? _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 0.840 _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 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3874 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 44 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 63.98 _reflns_number_total 3812 _reflns_number_observed 2853 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 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^)+(0.0937P)^2^+4.1688P] 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 SHELXL _refine_ls_extinction_coef 0.00070(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3811 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0863 _refine_ls_R_factor_obs 0.0628 _refine_ls_wR_factor_all 0.1798 _refine_ls_wR_factor_obs 0.1547 _refine_ls_goodness_of_fit_all 1.057 _refine_ls_goodness_of_fit_obs 1.065 _refine_ls_restrained_S_all 1.058 _refine_ls_restrained_S_obs 1.064 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.20103(13) 0.8413(4) 0.1023(5) 0.0719(12) Uani 1 d . . H1A H 0.20810(13) 0.8421(4) 0.0044(5) 0.086 Uiso 1 calc R . C2 C 0.16576(11) 0.7921(4) 0.1307(4) 0.0647(11) Uani 1 d . . H2A H 0.15372(11) 0.7444(4) 0.0728(4) 0.078 Uiso 1 calc R . C3 C 0.15514(9) 0.8276(4) 0.2493(4) 0.0595(10) Uani 1 d . . H3A H 0.13417(9) 0.8099(4) 0.2915(4) 0.071 Uiso 1 calc R . C4 C 0.18251(10) 0.9024(4) 0.3068(5) 0.0610(10) Uani 1 d . . H4A H 0.17462(10) 0.9532(4) 0.3767(5) 0.073 Uiso 1 calc R . C5 C 0.21544(9) 0.8336(3) 0.3497(5) 0.0605(10) Uani 1 d . . H5A H 0.23387(9) 0.8770(3) 0.3949(5) 0.073 Uiso 1 calc R . C6 C 0.22756(9) 0.7904(3) 0.2096(5) 0.0591(10) Uani 1 d . . H6A H 0.25180(9) 0.8120(3) 0.1915(5) 0.071 Uiso 1 calc R . C7 C 0.19546(12) 0.9488(4) 0.1704(6) 0.0798(14) Uani 1 d . . H7A H 0.21715(12) 0.9887(4) 0.1828(6) 0.096 Uiso 1 calc R . H7B H 0.17773(12) 0.9911(4) 0.1214(6) 0.096 Uiso 1 calc R . C8 C 0.22475(8) 0.6727(3) 0.2242(4) 0.0480(8) Uani 1 d . . O8 O 0.23244(8) 0.6064(2) 0.1391(3) 0.0671(8) Uani 1 d . . C9 C 0.20773(9) 0.7394(4) 0.4356(4) 0.0585(10) Uani 1 d . . O9 O 0.20037(10) 0.7361(4) 0.5575(3) 0.0941(13) Uani 1 d . . N10 N 0.21102(7) 0.6501(2) 0.3524(3) 0.0457(6) Uani 1 d . . C11 C 0.20405(9) 0.5433(3) 0.3993(4) 0.0587(10) Uani 1 d . . H11A H 0.19889(9) 0.5454(3) 0.4982(4) 0.070 Uiso 1 calc R . H11B H 0.22522(9) 0.5014(3) 0.3892(4) 0.070 Uiso 1 calc R . C12 C 0.17373(8) 0.4886(3) 0.3211(4) 0.0525(9) Uani 1 d . . H12A H 0.17715(8) 0.4953(3) 0.2212(4) 0.063 Uiso 1 calc R . H12B H 0.17418(8) 0.4140(3) 0.3440(4) 0.063 Uiso 1 calc R . N13 N 0.13932(6) 0.5314(2) 0.3537(3) 0.0393(6) Uani 1 d D . H13A H 0.1318(10) 0.5189(31) 0.4407(16) 0.052(11) Uiso 1 d D . C14 C 0.11453(7) 0.5500(2) 0.2544(3) 0.0323(6) Uani 1 d . . O14 O 0.11953(6) 0.5477(2) 0.1289(2) 0.0503(6) Uani 1 d . . C15 C 0.07813(7) 0.5732(2) 0.3123(3) 0.0343(6) Uani 1 d . . H15A H 0.06840(7) 0.5085(2) 0.3496(3) 0.041 Uiso 1 calc R . H15B H 0.08061(7) 0.6233(2) 0.3887(3) 0.041 Uiso 1 calc R . N16 N 0.05396(6) 0.6155(2) 0.2070(3) 0.0355(5) Uani 1 d . . C17 C 0.03334(9) 0.5614(2) 0.1109(4) 0.0456(8) Uani 1 d . . H17A H 0.03346(9) 0.4881(2) 0.1036(4) 0.055 Uiso 1 calc R . N18 N 0.01352(8) 0.6219(2) 0.0306(3) 0.0495(7) Uani 1 d . . C19 C 0.02120(7) 0.7236(2) 0.0766(3) 0.0371(6) Uani 1 d . . C20 C 0.04687(7) 0.7203(2) 0.1848(3) 0.0342(6) Uani 1 d . . N21 N 0.06159(7) 0.8007(2) 0.2531(3) 0.0427(6) Uani 1 d . . C22 C 0.04891(9) 0.8919(3) 0.2059(4) 0.0503(9) Uani 1 d . . H22A H 0.05802(9) 0.9522(3) 0.2493(4) 0.060 Uiso 1 calc R . N23 N 0.02462(7) 0.9085(2) 0.1036(3) 0.0473(7) Uani 1 d . . C24 C 0.01015(7) 0.8252(2) 0.0377(3) 0.0366(6) Uani 1 d . . N25 N -0.01446(7) 0.8535(2) -0.0646(3) 0.0430(6) Uani 1 d D . H25A H -0.0160(12) 0.9225(9) -0.0872(43) 0.064(12) Uiso 1 d D . C26 C -0.04271(7) 0.7938(2) -0.1136(3) 0.0363(6) Uani 1 d . . O26 O -0.04971(6) 0.7059(2) -0.0781(3) 0.0533(7) Uani 1 d . . O27 O -0.06138(6) 0.8530(2) -0.2057(3) 0.0456(6) Uani 1 d . . C28 C -0.09694(7) 0.8189(2) -0.2521(4) 0.0405(7) Uani 1 d . . C29 C -0.09518(13) 0.7169(3) -0.3294(6) 0.082(2) Uani 1 d . . H29A H -0.08007(13) 0.7246(3) -0.4077(6) 0.123 Uiso 1 calc R . H29B H -0.11838(13) 0.6973(3) -0.3624(6) 0.123 Uiso 1 calc R . H29C H -0.08595(13) 0.6630(3) -0.2679(6) 0.123 Uiso 1 calc R . C30 C -0.11960(13) 0.8170(7) -0.1284(7) 0.114(2) Uani 1 d . . H30A H -0.11935(13) 0.8852(7) -0.0846(7) 0.171 Uiso 1 calc R . H30B H -0.11085(13) 0.7650(7) -0.0630(7) 0.171 Uiso 1 calc R . H30C H -0.14328(13) 0.7993(7) -0.1575(7) 0.171 Uiso 1 calc R . C31 C -0.10834(12) 0.9062(3) -0.3527(6) 0.080(2) Uani 1 d . . H31A H -0.09334(12) 0.9061(3) -0.4320(6) 0.120 Uiso 1 calc R . H31B H -0.10660(12) 0.9732(3) -0.3059(6) 0.120 Uiso 1 calc R . H31C H -0.13229(12) 0.8944(3) -0.3837(6) 0.120 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 C1 0.079(3) 0.071(3) 0.067(2) 0.024(2) 0.026(2) 0.014(2) C2 0.062(2) 0.075(3) 0.056(2) 0.012(2) -0.027(2) -0.009(2) C3 0.0281(15) 0.084(3) 0.066(2) 0.025(2) -0.0094(15) -0.001(2) C4 0.037(2) 0.071(2) 0.074(2) -0.012(2) -0.007(2) 0.019(2) C5 0.031(2) 0.061(2) 0.088(3) -0.022(2) -0.021(2) 0.010(2) C6 0.032(2) 0.056(2) 0.090(3) -0.001(2) 0.018(2) -0.0021(15) C7 0.045(2) 0.060(2) 0.135(4) 0.019(3) 0.016(2) 0.002(2) C8 0.0323(15) 0.058(2) 0.054(2) -0.003(2) 0.0066(13) -0.0010(14) O8 0.070(2) 0.067(2) 0.065(2) -0.0099(14) 0.0199(14) 0.0035(14) C9 0.033(2) 0.087(3) 0.054(2) -0.016(2) -0.0150(15) 0.025(2) O9 0.079(2) 0.156(4) 0.047(2) -0.015(2) -0.0087(14) 0.053(2) N10 0.0268(12) 0.063(2) 0.0471(14) 0.0017(13) -0.0033(10) 0.0029(11) C11 0.029(2) 0.077(3) 0.070(2) 0.027(2) -0.0054(15) 0.008(2) C12 0.030(2) 0.048(2) 0.079(2) 0.008(2) 0.006(2) 0.0065(13) N13 0.0262(12) 0.0492(14) 0.0426(13) 0.0070(11) 0.0014(10) 0.0049(10) C14 0.0311(14) 0.0300(13) 0.0359(15) 0.0027(10) 0.0006(11) 0.0015(10) O14 0.0487(13) 0.066(2) 0.0360(12) 0.0028(10) 0.0033(9) 0.0089(11) C15 0.0268(13) 0.0350(14) 0.0411(15) 0.0028(11) -0.0012(11) 0.0060(11) N16 0.0279(11) 0.0306(11) 0.0474(13) 0.0001(10) -0.0093(10) 0.0046(9) C17 0.041(2) 0.0317(14) 0.063(2) -0.0064(14) -0.0169(14) 0.0041(13) N18 0.0455(15) 0.0339(13) 0.068(2) -0.0070(12) -0.0249(13) 0.0038(11) C19 0.0272(13) 0.0335(14) 0.050(2) 0.0020(12) -0.0105(12) 0.0004(11) C20 0.0256(12) 0.0325(14) 0.0441(15) 0.0021(12) -0.0053(11) -0.0006(11) N21 0.0342(12) 0.0332(12) 0.060(2) 0.0035(11) -0.0169(11) -0.0031(10) C22 0.046(2) 0.0317(15) 0.072(2) 0.0040(15) -0.028(2) -0.0084(13) N23 0.0394(14) 0.0335(13) 0.068(2) 0.0073(12) -0.0225(13) -0.0065(11) C24 0.0270(13) 0.0310(14) 0.051(2) 0.0065(12) -0.0102(12) -0.0022(11) N25 0.0338(13) 0.0327(12) 0.061(2) 0.0079(11) -0.0218(12) -0.0040(10) C26 0.0279(13) 0.0316(14) 0.049(2) 0.0048(12) -0.0107(12) -0.0024(11) O26 0.0398(12) 0.0407(12) 0.078(2) 0.0173(12) -0.0194(11) -0.0096(10) O27 0.0334(11) 0.0353(11) 0.0668(14) 0.0092(10) -0.0247(10) -0.0056(9) C28 0.0227(13) 0.039(2) 0.059(2) -0.0018(14) -0.0133(12) -0.0020(11) C29 0.074(3) 0.052(2) 0.117(4) -0.023(2) -0.047(3) 0.006(2) C30 0.043(2) 0.200(8) 0.100(4) 0.010(4) 0.019(2) 0.023(3) C31 0.063(3) 0.054(2) 0.121(4) 0.015(2) -0.059(3) -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 C1 C2 1.508(6) . ? C1 C7 1.525(7) . ? C1 C6 1.556(6) . ? C2 C3 1.294(6) . ? C3 C4 1.498(6) . ? C4 C7 1.523(7) . ? C4 C5 1.569(5) . ? C5 C9 1.481(6) . ? C5 C6 1.528(6) . ? C6 C8 1.500(5) . ? C8 O8 1.209(4) . ? C8 N10 1.375(4) . ? C9 O9 1.206(5) . ? C9 N10 1.389(5) . ? N10 C11 1.450(5) . ? C11 C12 1.522(5) . ? C12 N13 1.456(4) . ? N13 C14 1.338(4) . ? C14 O14 1.220(4) . ? C14 C15 1.531(4) . ? C15 N16 1.445(4) . ? N16 C20 1.368(4) . ? N16 C17 1.373(4) . ? C17 N18 1.308(4) . ? N18 C19 1.389(4) . ? C19 C24 1.399(4) . ? C19 C20 1.401(4) . ? C20 N21 1.325(4) . ? N21 C22 1.324(4) . ? C22 N23 1.342(4) . ? N23 C24 1.338(4) . ? C24 N25 1.380(4) . ? N25 C26 1.383(4) . ? C26 O26 1.195(4) . ? C26 O27 1.342(3) . ? O27 C28 1.473(3) . ? C28 C30 1.481(6) . ? C28 C29 1.490(5) . ? C28 C31 1.518(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 C2 C1 C7 99.1(4) . . ? C2 C1 C6 105.8(3) . . ? C7 C1 C6 100.6(4) . . ? C3 C2 C1 108.3(4) . . ? C2 C3 C4 108.1(4) . . ? C3 C4 C7 99.6(3) . . ? C3 C4 C5 106.5(3) . . ? C7 C4 C5 99.4(3) . . ? C9 C5 C6 105.5(3) . . ? C9 C5 C4 115.1(3) . . ? C6 C5 C4 103.1(3) . . ? C8 C6 C5 104.5(3) . . ? C8 C6 C1 115.2(4) . . ? C5 C6 C1 102.9(3) . . ? C4 C7 C1 94.2(3) . . ? O8 C8 N10 123.9(4) . . ? O8 C8 C6 127.4(3) . . ? N10 C8 C6 108.6(3) . . ? O9 C9 N10 123.5(5) . . ? O9 C9 C5 128.1(4) . . ? N10 C9 C5 108.4(3) . . ? C8 N10 C9 112.5(3) . . ? C8 N10 C11 123.1(3) . . ? C9 N10 C11 124.1(3) . . ? N10 C11 C12 114.4(3) . . ? N13 C12 C11 113.4(3) . . ? C14 N13 C12 122.0(3) . . ? O14 C14 N13 124.6(3) . . ? O14 C14 C15 121.8(3) . . ? N13 C14 C15 113.7(2) . . ? N16 C15 C14 112.4(2) . . ? C20 N16 C17 105.9(2) . . ? C20 N16 C15 125.8(2) . . ? C17 N16 C15 128.3(2) . . ? N18 C17 N16 114.1(3) . . ? C17 N18 C19 104.1(2) . . ? N18 C19 C24 135.1(3) . . ? N18 C19 C20 110.0(3) . . ? C24 C19 C20 114.9(3) . . ? N21 C20 N16 126.2(3) . . ? N21 C20 C19 128.0(3) . . ? N16 C20 C19 105.8(2) . . ? C22 N21 C20 111.0(3) . . ? N21 C22 N23 128.3(3) . . ? C24 N23 C22 119.0(3) . . ? N23 C24 N25 112.9(3) . . ? N23 C24 C19 118.8(3) . . ? N25 C24 C19 128.3(3) . . ? C24 N25 C26 126.9(3) . . ? O26 C26 O27 126.0(3) . . ? O26 C26 N25 126.1(3) . . ? O27 C26 N25 107.9(2) . . ? C26 O27 C28 119.8(2) . . ? O27 C28 C30 108.2(3) . . ? O27 C28 C29 110.4(3) . . ? C30 C28 C29 114.6(5) . . ? O27 C28 C31 102.7(3) . . ? C30 C28 C31 110.8(4) . . ? C29 C28 C31 109.4(4) . . ? _refine_diff_density_max 0.324 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.059 data_s92 _database_code_CSD 168681 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N6 O4' _chemical_formula_weight 382.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7111(2) _cell_length_b 9.2637(5) _cell_length_c 15.5593(8) _cell_angle_alpha 103.438(2) _cell_angle_beta 98.437(3) _cell_angle_gamma 102.274(3) _cell_volume 899.54(7) _cell_formula_units_Z 2 _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 ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 11622 _diffrn_reflns_av_R_equivalents 0.0711 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3097 _reflns_number_gt 2520 _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 w=1/[\s^2^(Fo^2^)+(0.0736P)^2^+0.1435P] 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 3097 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1206 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O2 O 0.18230(17) 0.95357(13) 0.25601(8) 0.0210(3) Uani 1 d . . . O3 O -0.22070(19) 0.92465(15) 0.33553(9) 0.0307(3) Uani 1 d . . . C5 C -0.4392(2) 1.17612(19) 0.08371(11) 0.0184(4) Uani 1 d . . . N3 N -0.0945(2) 1.20974(16) 0.04605(10) 0.0210(4) Uani 1 d . . . O4 O 0.3174(2) 0.77949(16) 0.47590(10) 0.0352(4) Uani 1 d . . . O1 O 0.10194(19) 1.18016(14) 0.26273(9) 0.0276(3) Uani 1 d . . . N5 N -0.5598(2) 1.08246(17) 0.12501(10) 0.0203(3) Uani 1 d . . . N4 N -0.2488(2) 1.02759(16) 0.12352(9) 0.0193(3) Uani 1 d . . . C3 C -0.2482(3) 1.14266(19) 0.08208(11) 0.0176(4) Uani 1 d . . . N1 N -0.6465(2) 1.3473(2) 0.04979(12) 0.0260(4) Uani 1 d . . . N2 N -0.3232(2) 1.36730(17) 0.01111(10) 0.0217(4) Uani 1 d . . . C10 C -0.1340(3) 0.8423(2) 0.36913(12) 0.0227(4) Uani 1 d . . . C7 C 0.0761(2) 1.0467(2) 0.22660(12) 0.0196(4) Uani 1 d . . . C1 C -0.4743(2) 1.2970(2) 0.04830(12) 0.0195(4) Uani 1 d . . . C2 C -0.1490(3) 1.3174(2) 0.01145(12) 0.0217(4) Uani 1 d . . . C4 C -0.4395(3) 0.9973(2) 0.14777(12) 0.0201(4) Uani 1 d . . . N6 N 0.0739(2) 0.88555(16) 0.41270(10) 0.0213(4) Uani 1 d . . . C13 C 0.1395(3) 0.7688(2) 0.44153(12) 0.0233(4) Uani 1 d . . . C9 C 0.2163(3) 1.0328(2) 0.41883(12) 0.0229(4) Uani 1 d . . . C6 C -0.0807(3) 0.9555(2) 0.14044(12) 0.0206(4) Uani 1 d . . . C8 C 0.3299(3) 1.0222(2) 0.34184(12) 0.0243(4) Uani 1 d . . . C14 C -0.2838(3) 0.5624(2) 0.27424(13) 0.0315(5) Uani 1 d . . . C11 C -0.2269(3) 0.6799(2) 0.37029(12) 0.0243(4) Uani 1 d . . . C12 C -0.0468(3) 0.6310(2) 0.41926(13) 0.0250(4) Uani 1 d . . . C16 C -0.2217(3) 0.3663(2) 0.33199(15) 0.0350(5) Uani 1 d . . . C17 C -0.0228(3) 0.4918(2) 0.34658(14) 0.0306(5) Uani 1 d . . . C15 C -0.3756(3) 0.4086(2) 0.28980(14) 0.0355(5) Uani 1 d . . . C18 C -0.0674(3) 0.5445(3) 0.26097(14) 0.0350(5) Uani 1 d . . . H9B H 0.316(3) 1.060(2) 0.4783(13) 0.025(5) Uiso 1 d . . . H4 H -0.476(3) 0.919(2) 0.1791(12) 0.018(5) Uiso 1 d . . . H6A H -0.140(3) 0.848(2) 0.1447(12) 0.022(5) Uiso 1 d . . . H18B H 0.022(3) 0.644(3) 0.2600(14) 0.037(6) Uiso 1 d . . . H9A H 0.127(3) 1.104(2) 0.4165(13) 0.026(5) Uiso 1 d . . . H11 H -0.342(3) 0.679(2) 0.3993(13) 0.026(5) Uiso 1 d . . . H8B H 0.407(3) 1.126(2) 0.3443(13) 0.024(5) Uiso 1 d . . . H6B H -0.004(3) 0.950(2) 0.0915(14) 0.030(5) Uiso 1 d . . . H12 H -0.068(3) 0.608(2) 0.4741(14) 0.028(5) Uiso 1 d . . . H2 H -0.046(3) 1.370(2) -0.0180(13) 0.024(5) Uiso 1 d . . . H8A H 0.423(3) 0.951(2) 0.3441(14) 0.033(5) Uiso 1 d . . . H17 H 0.106(3) 0.465(2) 0.3588(14) 0.036(6) Uiso 1 d . . . H18A H -0.072(4) 0.461(3) 0.2042(17) 0.050(7) Uiso 1 d . . . H16 H -0.231(4) 0.274(3) 0.3577(16) 0.052(7) Uiso 1 d . . . H14 H -0.367(3) 0.596(2) 0.2298(15) 0.031(5) Uiso 1 d . . . H1NB H -0.655(3) 1.433(3) 0.0304(14) 0.036(6) Uiso 1 d . . . H15 H -0.523(4) 0.361(3) 0.2773(15) 0.046(6) Uiso 1 d . . . H1NA H -0.753(4) 1.295(3) 0.0683(15) 0.039(6) Uiso 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 O2 0.0181(6) 0.0249(7) 0.0231(7) 0.0090(5) 0.0035(5) 0.0094(5) O3 0.0197(7) 0.0347(8) 0.0429(8) 0.0178(7) 0.0058(6) 0.0106(6) C5 0.0155(9) 0.0204(9) 0.0182(9) 0.0041(7) 0.0014(7) 0.0046(7) N3 0.0164(8) 0.0235(8) 0.0256(8) 0.0088(7) 0.0060(6) 0.0069(6) O4 0.0243(8) 0.0348(8) 0.0415(8) 0.0132(7) -0.0090(6) 0.0044(6) O1 0.0256(7) 0.0207(8) 0.0348(8) 0.0055(6) 0.0018(6) 0.0075(5) N5 0.0167(8) 0.0224(8) 0.0219(8) 0.0076(6) 0.0044(6) 0.0033(6) N4 0.0173(8) 0.0218(8) 0.0203(7) 0.0069(6) 0.0030(6) 0.0074(6) C3 0.0164(9) 0.0185(9) 0.0178(9) 0.0048(7) 0.0026(7) 0.0046(6) N1 0.0152(8) 0.0281(9) 0.0422(10) 0.0190(8) 0.0085(7) 0.0092(7) N2 0.0169(8) 0.0232(8) 0.0280(8) 0.0104(7) 0.0058(6) 0.0071(6) C10 0.0179(9) 0.0297(11) 0.0217(9) 0.0057(8) 0.0071(7) 0.0078(7) C7 0.0155(9) 0.0231(10) 0.0247(9) 0.0096(8) 0.0078(7) 0.0087(7) C1 0.0135(9) 0.0212(9) 0.0215(9) 0.0038(7) 0.0006(7) 0.0040(7) C2 0.0167(9) 0.0241(10) 0.0275(10) 0.0107(8) 0.0074(7) 0.0058(7) C4 0.0174(9) 0.0213(10) 0.0218(9) 0.0069(8) 0.0040(7) 0.0045(7) N6 0.0189(8) 0.0223(8) 0.0211(8) 0.0058(6) 0.0011(6) 0.0036(6) C13 0.0242(10) 0.0254(10) 0.0181(9) 0.0039(8) 0.0013(7) 0.0057(7) C9 0.0206(10) 0.0216(10) 0.0241(10) 0.0053(8) 0.0015(8) 0.0037(7) C6 0.0208(9) 0.0210(10) 0.0232(10) 0.0087(8) 0.0041(7) 0.0096(7) C8 0.0153(9) 0.0306(11) 0.0272(10) 0.0103(8) 0.0004(7) 0.0062(8) C14 0.0276(11) 0.0337(12) 0.0248(10) 0.0043(9) -0.0035(8) 0.0002(8) C11 0.0195(10) 0.0265(10) 0.0256(10) 0.0067(8) 0.0054(8) 0.0032(7) C12 0.0238(10) 0.0262(10) 0.0243(10) 0.0092(8) 0.0029(8) 0.0044(7) C16 0.0351(12) 0.0239(11) 0.0382(12) 0.0018(9) 0.0047(9) 0.0006(8) C17 0.0252(11) 0.0250(11) 0.0383(12) 0.0034(9) 0.0064(9) 0.0051(8) C15 0.0304(12) 0.0295(12) 0.0358(12) 0.0005(9) 0.0014(9) -0.0023(9) C18 0.0361(12) 0.0303(12) 0.0303(11) -0.0016(9) 0.0100(9) -0.0002(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 O2 C7 1.345(2) . ? O2 C8 1.456(2) . ? O3 C10 1.216(2) . ? C5 C3 1.383(2) . ? C5 N5 1.391(2) . ? C5 C1 1.405(2) . ? N3 C2 1.329(2) . ? N3 C3 1.351(2) . ? O4 C13 1.208(2) . ? O1 C7 1.197(2) . ? N5 C4 1.310(2) . ? N4 C3 1.368(2) . ? N4 C4 1.377(2) . ? N4 C6 1.450(2) . ? N1 C1 1.336(2) . ? N2 C2 1.345(2) . ? N2 C1 1.361(2) . ? C10 N6 1.388(2) . ? C10 C11 1.507(3) . ? C7 C6 1.517(2) . ? N6 C13 1.391(2) . ? N6 C9 1.463(2) . ? C13 C12 1.517(3) . ? C9 C8 1.507(3) . ? C14 C15 1.516(3) . ? C14 C18 1.534(3) . ? C14 C11 1.569(3) . ? C11 C12 1.539(3) . ? C12 C17 1.560(3) . ? C16 C15 1.321(3) . ? C16 C17 1.521(3) . ? C17 C18 1.533(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 C7 O2 C8 115.66(14) . . ? C3 C5 N5 110.84(15) . . ? C3 C5 C1 117.11(16) . . ? N5 C5 C1 132.00(15) . . ? C2 N3 C3 110.64(14) . . ? C4 N5 C5 103.53(14) . . ? C3 N4 C4 105.83(14) . . ? C3 N4 C6 126.90(15) . . ? C4 N4 C6 127.25(15) . . ? N3 C3 N4 127.46(15) . . ? N3 C3 C5 126.65(16) . . ? N4 C3 C5 105.89(15) . . ? C2 N2 C1 117.81(15) . . ? O3 C10 N6 124.02(17) . . ? O3 C10 C11 127.36(16) . . ? N6 C10 C11 108.62(15) . . ? O1 C7 O2 125.31(16) . . ? O1 C7 C6 125.57(15) . . ? O2 C7 C6 109.12(14) . . ? N1 C1 N2 118.37(16) . . ? N1 C1 C5 123.66(16) . . ? N2 C1 C5 117.97(15) . . ? N3 C2 N2 129.70(17) . . ? N5 C4 N4 113.90(16) . . ? C10 N6 C13 113.24(15) . . ? C10 N6 C9 123.49(15) . . ? C13 N6 C9 122.93(15) . . ? O4 C13 N6 123.82(17) . . ? O4 C13 C12 128.02(17) . . ? N6 C13 C12 108.13(15) . . ? N6 C9 C8 111.80(15) . . ? N4 C6 C7 111.82(14) . . ? O2 C8 C9 110.18(14) . . ? C15 C14 C18 100.35(17) . . ? C15 C14 C11 104.87(16) . . ? C18 C14 C11 100.87(15) . . ? C10 C11 C12 105.06(14) . . ? C10 C11 C14 113.11(16) . . ? C12 C11 C14 102.48(15) . . ? C13 C12 C11 104.87(15) . . ? C13 C12 C17 112.34(15) . . ? C11 C12 C17 103.39(15) . . ? C15 C16 C17 107.62(19) . . ? C16 C17 C18 100.03(17) . . ? C16 C17 C12 105.30(16) . . ? C18 C17 C12 100.61(16) . . ? C16 C15 C14 107.60(18) . . ? C17 C18 C14 93.79(16) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1NB N2 0.92(2) 2.12(2) 3.044(2) 178.6(19) 2_485 N1 H1NA N3 0.90(2) 2.21(2) 2.992(2) 145.8(19) 1_455 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.445 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.057