# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Numbers: 155368,155369 data_global loop_ _publ_author_name 'Bobosikova, Maria' 'Clegg, W.' 'Coles, Simon J.' 'Dandarova, Miloslava' 'Hursthouse, Michael B.' 'Kiss, Tibor' 'Krutosikova, Alzbeta' 'Liptaj, Tibor' 'Pronayova, N.' 'Ramsden, C. A.' _journal_coden_Cambridge 207 _publ_contact_author ;Prof C A Ramsden Department of Chemistry Keele University Keele STAFFS ST5 5BG UK ; data_s92_15b _database_code_CSD 155638 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 N3 O2' _chemical_formula_weight 391.42 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.508(2) _cell_length_b 3.832(4) _cell_length_c 30.909(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.30(3) _cell_angle_gamma 90.00 _cell_volume 1835.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12000 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 29.41 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type 'multi-scans' _exptl_absorpt_correction_T_min 0.9729 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68750 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12000 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 29.41 _reflns_number_total 5143 _reflns_number_gt 4019 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CAMERON _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^)+(0.0899P)^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 5143 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.981 _refine_ls_shift/su_max 0.027 _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 0.67740(5) -0.1155(3) 0.06819(3) 0.0226(2) Uani 1 1 d . . . O2 O 0.52251(5) 0.0677(2) 0.20913(3) 0.02024(19) Uani 1 1 d . . . N1 N 0.43969(6) -0.3098(3) 0.10938(3) 0.0178(2) Uani 1 1 d . . . N2 N 0.40176(6) -0.5156(3) 0.04036(3) 0.0209(2) Uani 1 1 d . . . H2 H 0.4200 -0.5723 0.0147 0.025 Uiso 1 1 calc R . . N3 N 0.54099(6) -0.3293(3) 0.05223(3) 0.0199(2) Uani 1 1 d . . . C1 C 0.80479(8) 0.1288(4) 0.10551(4) 0.0258(3) Uani 1 1 d . . . H1 H 0.8390 0.1084 0.0808 0.031 Uiso 1 1 calc R . . C2 C 0.83803(8) 0.2629(4) 0.14453(4) 0.0277(3) Uani 1 1 d . . . H2A H 0.8966 0.3362 0.1469 0.033 Uiso 1 1 calc R . . C3 C 0.78643(8) 0.2910(4) 0.18021(4) 0.0269(3) Uani 1 1 d . . . H3 H 0.8107 0.3831 0.2065 0.032 Uiso 1 1 calc R . . C4 C 0.70051(8) 0.1884(4) 0.17845(4) 0.0240(3) Uani 1 1 d . . . H4 H 0.6663 0.2111 0.2031 0.029 Uiso 1 1 calc R . . C5 C 0.66527(7) 0.0509(3) 0.13968(4) 0.0186(2) Uani 1 1 d . . . C6 C 0.71953(7) 0.0271(3) 0.10458(4) 0.0206(2) Uani 1 1 d . . . C7 C 0.59553(7) -0.1862(3) 0.08026(4) 0.0182(2) Uani 1 1 d . . . C8 C 0.58270(7) -0.0893(3) 0.12352(3) 0.0171(2) Uani 1 1 d . . . C9 C 0.49922(7) -0.1636(3) 0.13663(3) 0.0168(2) Uani 1 1 d . . . C10 C 0.46162(7) -0.3812(3) 0.06879(3) 0.0175(2) Uani 1 1 d . . . C11 C 0.31318(7) -0.5754(3) 0.04723(3) 0.0174(2) Uani 1 1 d . . . C12 C 0.25420(7) -0.4919(3) 0.01383(4) 0.0208(2) Uani 1 1 d . . . H12 H 0.2736 -0.3857 -0.0118 0.025 Uiso 1 1 calc R . . C13 C 0.16702(8) -0.5629(4) 0.01773(4) 0.0237(3) Uani 1 1 d . . . H13 H 0.1275 -0.5071 -0.0055 0.028 Uiso 1 1 calc R . . C14 C 0.13673(7) -0.7139(3) 0.05501(4) 0.0220(3) Uani 1 1 d . . . C15 C 0.19655(8) -0.7936(3) 0.08832(4) 0.0209(2) Uani 1 1 d . . . H15 H 0.1769 -0.8956 0.1142 0.025 Uiso 1 1 calc R . . C16 C 0.28392(8) -0.7283(3) 0.08486(4) 0.0198(2) Uani 1 1 d . . . H16 H 0.3235 -0.7873 0.1079 0.024 Uiso 1 1 calc R . . C17 C 0.04213(8) -0.7947(4) 0.05942(5) 0.0328(3) Uani 1 1 d . . . H17A H 0.0351 -1.0438 0.0655 0.049 Uiso 1 1 calc R . . H17B H 0.0103 -0.7353 0.0324 0.049 Uiso 1 1 calc R . . H17C H 0.0197 -0.6574 0.0832 0.049 Uiso 1 1 calc R . . C18 C 0.46693(7) -0.0928(3) 0.17934(3) 0.0175(2) Uani 1 1 d . . . C19 C 0.38903(7) -0.1616(3) 0.19618(3) 0.0190(2) Uani 1 1 d . . . H19 H 0.3408 -0.2704 0.1818 0.023 Uiso 1 1 calc R . . C20 C 0.39426(7) -0.0367(3) 0.24003(3) 0.0183(2) Uani 1 1 d . . . C21 C 0.47706(7) 0.1014(3) 0.24620(3) 0.0189(2) Uani 1 1 d . . . C22 C 0.50863(8) 0.2510(3) 0.28432(4) 0.0236(3) Uani 1 1 d . . . H22 H 0.5653 0.3447 0.2872 0.028 Uiso 1 1 calc R . . C23 C 0.45245(9) 0.2560(4) 0.31815(4) 0.0261(3) Uani 1 1 d . . . H23 H 0.4710 0.3556 0.3451 0.031 Uiso 1 1 calc R . . C24 C 0.36886(9) 0.1173(3) 0.31341(4) 0.0257(3) Uani 1 1 d . . . H24 H 0.3321 0.1242 0.3373 0.031 Uiso 1 1 calc R . . C25 C 0.33879(8) -0.0291(3) 0.27490(4) 0.0223(2) Uani 1 1 d . . . H25 H 0.2821 -0.1223 0.2720 0.027 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 0.0195(4) 0.0305(5) 0.0179(4) -0.0015(3) 0.0044(3) -0.0031(3) O2 0.0211(4) 0.0257(5) 0.0140(4) -0.0056(3) 0.0018(3) -0.0001(3) N1 0.0206(4) 0.0203(5) 0.0127(4) -0.0018(4) 0.0020(3) 0.0013(4) N2 0.0202(5) 0.0310(6) 0.0117(4) -0.0056(4) 0.0037(3) -0.0029(4) N3 0.0208(5) 0.0249(6) 0.0143(4) -0.0016(4) 0.0038(3) -0.0007(4) C1 0.0217(6) 0.0277(7) 0.0281(6) 0.0027(5) 0.0025(4) -0.0025(5) C2 0.0220(6) 0.0257(7) 0.0353(7) 0.0026(5) -0.0019(5) -0.0040(5) C3 0.0265(6) 0.0268(7) 0.0271(6) -0.0029(5) -0.0051(5) -0.0036(5) C4 0.0258(6) 0.0246(7) 0.0215(6) -0.0030(5) -0.0011(4) -0.0016(5) C5 0.0200(5) 0.0168(6) 0.0189(5) 0.0011(4) 0.0000(4) 0.0003(4) C6 0.0221(5) 0.0195(6) 0.0202(5) 0.0006(4) 0.0002(4) -0.0005(4) C7 0.0187(5) 0.0207(6) 0.0156(5) 0.0015(4) 0.0043(4) 0.0009(4) C8 0.0211(5) 0.0170(6) 0.0131(5) -0.0009(4) 0.0012(4) 0.0007(4) C9 0.0212(5) 0.0166(5) 0.0127(5) 0.0004(4) 0.0018(4) 0.0021(4) C10 0.0206(5) 0.0185(6) 0.0135(5) -0.0007(4) 0.0031(4) 0.0010(4) C11 0.0200(5) 0.0179(6) 0.0145(5) -0.0034(4) 0.0037(4) 0.0001(4) C12 0.0241(5) 0.0247(6) 0.0139(5) 0.0019(4) 0.0030(4) -0.0001(5) C13 0.0227(5) 0.0285(7) 0.0199(6) 0.0031(5) -0.0003(4) 0.0012(5) C14 0.0218(5) 0.0212(6) 0.0233(6) -0.0001(5) 0.0049(4) 0.0001(4) C15 0.0267(6) 0.0192(6) 0.0173(5) 0.0019(4) 0.0062(4) -0.0008(4) C16 0.0239(5) 0.0207(6) 0.0148(5) 0.0002(4) 0.0016(4) 0.0007(4) C17 0.0230(6) 0.0375(8) 0.0382(7) 0.0042(6) 0.0061(5) -0.0030(5) C18 0.0214(5) 0.0183(6) 0.0128(5) -0.0021(4) 0.0005(4) 0.0005(4) C19 0.0229(5) 0.0200(6) 0.0142(5) -0.0021(4) 0.0020(4) -0.0002(4) C20 0.0248(5) 0.0165(5) 0.0137(5) -0.0001(4) 0.0016(4) 0.0024(4) C21 0.0241(5) 0.0196(6) 0.0131(5) -0.0011(4) 0.0029(4) 0.0044(4) C22 0.0272(6) 0.0247(7) 0.0188(5) -0.0048(5) -0.0024(4) 0.0038(5) C23 0.0400(7) 0.0237(7) 0.0144(5) -0.0042(5) -0.0002(4) 0.0064(5) C24 0.0403(7) 0.0215(6) 0.0159(5) -0.0007(5) 0.0085(5) 0.0055(5) C25 0.0289(6) 0.0195(6) 0.0189(5) 0.0005(4) 0.0065(4) 0.0015(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.3648(13) . ? O1 C6 1.3895(14) . ? O2 C21 1.3751(13) . ? O2 C18 1.3804(14) . ? N1 C10 1.3413(14) . ? N1 C9 1.3465(15) . ? N2 C10 1.3541(15) . ? N2 C11 1.4170(14) . ? N3 C7 1.3066(15) . ? N3 C10 1.3664(14) . ? C1 C6 1.3777(16) . ? C1 C2 1.3911(19) . ? C2 C3 1.3925(19) . ? C3 C4 1.3882(17) . ? C4 C5 1.4000(16) . ? C5 C6 1.4024(16) . ? C5 C8 1.4581(16) . ? C7 C8 1.4097(15) . ? C8 C9 1.4012(15) . ? C9 C18 1.4561(15) . ? C11 C12 1.3890(16) . ? C11 C16 1.3945(16) . ? C12 C13 1.3890(16) . ? C13 C14 1.3880(17) . ? C14 C15 1.3919(17) . ? C14 C17 1.5109(16) . ? C15 C16 1.3861(16) . ? C18 C19 1.3602(15) . ? C19 C20 1.4366(15) . ? C20 C21 1.3949(17) . ? C20 C25 1.4062(15) . ? C21 C22 1.3822(16) . ? C22 C23 1.3878(18) . ? C23 C24 1.403(2) . ? C24 C25 1.3799(17) . ? 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 O1 C6 105.62(9) . . ? C21 O2 C18 105.69(9) . . ? C10 N1 C9 118.46(10) . . ? C10 N2 C11 127.44(9) . . ? C7 N3 C10 112.44(9) . . ? C6 C1 C2 116.41(12) . . ? C1 C2 C3 120.70(12) . . ? C4 C3 C2 121.88(12) . . ? C3 C4 C5 118.78(12) . . ? C4 C5 C6 117.45(11) . . ? C4 C5 C8 137.66(11) . . ? C6 C5 C8 104.89(10) . . ? C1 C6 O1 123.22(11) . . ? C1 C6 C5 124.79(11) . . ? O1 C6 C5 112.00(10) . . ? N3 C7 O1 119.13(10) . . ? N3 C7 C8 128.84(10) . . ? O1 C7 C8 112.03(10) . . ? C9 C8 C7 112.82(10) . . ? C9 C8 C5 141.69(10) . . ? C7 C8 C5 105.46(10) . . ? N1 C9 C8 121.47(10) . . ? N1 C9 C18 113.11(10) . . ? C8 C9 C18 125.42(10) . . ? N1 C10 N2 119.44(10) . . ? N1 C10 N3 125.93(11) . . ? N2 C10 N3 114.63(10) . . ? C12 C11 C16 119.35(10) . . ? C12 C11 N2 117.70(10) . . ? C16 C11 N2 122.87(10) . . ? C11 C12 C13 120.31(11) . . ? C14 C13 C12 121.11(11) . . ? C13 C14 C15 117.89(11) . . ? C13 C14 C17 121.51(12) . . ? C15 C14 C17 120.60(11) . . ? C16 C15 C14 121.87(11) . . ? C15 C16 C11 119.46(11) . . ? C19 C18 O2 111.80(10) . . ? C19 C18 C9 130.83(11) . . ? O2 C18 C9 117.37(10) . . ? C18 C19 C20 106.21(10) . . ? C21 C20 C25 118.39(10) . . ? C21 C20 C19 105.79(10) . . ? C25 C20 C19 135.81(11) . . ? O2 C21 C22 124.98(11) . . ? O2 C21 C20 110.50(10) . . ? C22 C21 C20 124.51(11) . . ? C21 C22 C23 115.88(12) . . ? C22 C23 C24 121.42(12) . . ? C25 C24 C23 121.52(11) . . ? C24 C25 C20 118.28(11) . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 29.41 _diffrn_measured_fraction_theta_full 0.914 _refine_diff_density_max 0.395 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.064 data_s92_23 _database_code_CSD 155639 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 N3' _chemical_formula_weight 297.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 25.908(5) _cell_length_b 10.067(2) _cell_length_c 11.851(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.36(3) _cell_angle_gamma 90.00 _cell_volume 3007.3(10) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 20181 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 27.52 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9690 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20181 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3426 _reflns_number_gt 2720 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1995)' _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^)+(0.1000P)^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_number_reflns 3426 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1500 _refine_ls_wR_factor_gt 0.1375 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 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 0.35536(4) 0.16651(10) 1.15942(8) 0.0249(3) Uani 1 1 d . . . N2 N 0.29787(4) 0.13637(10) 0.97155(8) 0.0246(3) Uani 1 1 d . . . N3 N 0.35091(4) 0.03549(10) 1.31639(8) 0.0258(3) Uani 1 1 d . . . H3 H 0.3335 -0.0230 1.3453 0.031 Uiso 1 1 calc R . . C1 C 0.35602(5) 0.33355(13) 0.88208(11) 0.0308(3) Uani 1 1 d . . . H1 H 0.3302 0.2862 0.8299 0.037 Uiso 1 1 calc R . . C2 C 0.38306(5) 0.43507(14) 0.84249(12) 0.0361(3) Uani 1 1 d . . . H2 H 0.3756 0.4549 0.7637 0.043 Uiso 1 1 calc R . . C3 C 0.42117(5) 0.50769(13) 0.91914(12) 0.0349(3) Uani 1 1 d . . . H3A H 0.4389 0.5767 0.8922 0.042 Uiso 1 1 calc R . . C4 C 0.43259(5) 0.47662(13) 1.03620(11) 0.0323(3) Uani 1 1 d . . . H4 H 0.4582 0.5250 1.0880 0.039 Uiso 1 1 calc R . . C5 C 0.40611(5) 0.37397(12) 1.07642(10) 0.0273(3) Uani 1 1 d . . . H5 H 0.4144 0.3532 1.1550 0.033 Uiso 1 1 calc R . . C6 C 0.36714(4) 0.30130(12) 1.00027(10) 0.0248(3) Uani 1 1 d . . . C7 C 0.33767(4) 0.19451(11) 1.04482(10) 0.0232(3) Uani 1 1 d . . . C8 C 0.33134(4) 0.07027(11) 1.20386(9) 0.0233(3) Uani 1 1 d . . . C9 C 0.28546(4) 0.00285(11) 1.13548(9) 0.0231(3) Uani 1 1 d . . . C10 C 0.27024(4) 0.04191(11) 1.01799(9) 0.0235(3) Uani 1 1 d . . . C11 C 0.22608(5) -0.02010(12) 0.94512(10) 0.0285(3) Uani 1 1 d . . . H11 H 0.2158 0.0043 0.8675 0.034 Uiso 1 1 calc R . . C12 C 0.19821(5) -0.11592(13) 0.98766(11) 0.0302(3) Uani 1 1 d . . . H12 H 0.1690 -0.1558 0.9388 0.036 Uiso 1 1 calc R . . C13 C 0.21327(5) -0.15431(13) 1.10402(11) 0.0290(3) Uani 1 1 d . . . H13 H 0.1940 -0.2191 1.1322 0.035 Uiso 1 1 calc R . . C14 C 0.25644(5) -0.09685(12) 1.17683(10) 0.0262(3) Uani 1 1 d . . . H14 H 0.2666 -0.1239 1.2538 0.031 Uiso 1 1 calc R . . C15 C 0.39775(5) 0.08730(11) 1.39073(10) 0.0250(3) Uani 1 1 d . . . C16 C 0.39725(5) 0.11383(12) 1.50575(10) 0.0292(3) Uani 1 1 d . . . H16 H 0.3664 0.1002 1.5318 0.035 Uiso 1 1 calc R . . C17 C 0.44258(5) 0.16051(13) 1.58148(11) 0.0356(3) Uani 1 1 d . . . H17 H 0.4422 0.1772 1.6585 0.043 Uiso 1 1 calc R . . C18 C 0.48843(5) 0.18249(13) 1.54335(12) 0.0369(3) Uani 1 1 d . . . H18 H 0.5186 0.2159 1.5938 0.044 Uiso 1 1 calc R . . C19 C 0.48905(5) 0.15440(13) 1.42937(12) 0.0341(3) Uani 1 1 d . . . H19 H 0.5200 0.1679 1.4037 0.041 Uiso 1 1 calc R . . C20 C 0.44420(5) 0.10642(12) 1.35321(11) 0.0294(3) Uani 1 1 d . . . H20 H 0.4451 0.0870 1.2770 0.035 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 N1 0.0291(5) 0.0236(6) 0.0219(5) 0.0002(4) 0.0060(4) -0.0012(4) N2 0.0268(5) 0.0251(5) 0.0225(5) 0.0001(4) 0.0072(4) -0.0010(4) N3 0.0280(5) 0.0272(6) 0.0222(5) 0.0020(4) 0.0056(4) -0.0047(4) C1 0.0325(7) 0.0302(7) 0.0284(6) 0.0023(5) 0.0042(5) -0.0050(5) C2 0.0391(7) 0.0373(8) 0.0324(7) 0.0089(6) 0.0089(6) -0.0055(6) C3 0.0315(7) 0.0295(7) 0.0445(8) 0.0091(6) 0.0100(6) -0.0041(5) C4 0.0271(6) 0.0274(7) 0.0404(7) -0.0002(5) 0.0037(5) -0.0039(5) C5 0.0276(6) 0.0265(7) 0.0275(6) 0.0003(5) 0.0059(5) 0.0018(5) C6 0.0267(6) 0.0225(6) 0.0263(6) 0.0009(5) 0.0085(5) 0.0024(4) C7 0.0257(6) 0.0219(6) 0.0229(6) -0.0013(4) 0.0071(5) 0.0025(4) C8 0.0257(6) 0.0223(6) 0.0232(6) -0.0012(4) 0.0082(5) 0.0024(4) C9 0.0253(6) 0.0220(6) 0.0233(6) -0.0021(5) 0.0080(5) 0.0025(4) C10 0.0250(6) 0.0234(6) 0.0232(6) -0.0008(5) 0.0083(5) 0.0017(4) C11 0.0292(6) 0.0320(7) 0.0236(6) 0.0001(5) 0.0050(5) -0.0007(5) C12 0.0274(6) 0.0310(7) 0.0311(6) -0.0024(5) 0.0048(5) -0.0035(5) C13 0.0295(6) 0.0264(7) 0.0326(6) 0.0012(5) 0.0100(5) -0.0036(5) C14 0.0284(6) 0.0270(7) 0.0246(6) 0.0013(5) 0.0089(5) 0.0012(5) C15 0.0273(6) 0.0208(6) 0.0253(6) 0.0024(4) 0.0026(5) 0.0008(4) C16 0.0334(7) 0.0265(7) 0.0273(6) 0.0015(5) 0.0062(5) -0.0010(5) C17 0.0452(8) 0.0298(7) 0.0274(6) -0.0010(5) -0.0006(6) 0.0004(6) C18 0.0332(7) 0.0272(7) 0.0432(8) -0.0002(6) -0.0060(6) -0.0036(5) C19 0.0281(6) 0.0280(7) 0.0450(8) 0.0052(6) 0.0058(6) -0.0003(5) C20 0.0317(7) 0.0277(7) 0.0295(6) 0.0031(5) 0.0089(5) 0.0011(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.3248(15) . ? N1 C7 1.3587(15) . ? N2 C7 1.3214(16) . ? N2 C10 1.3790(15) . ? N3 C8 1.3585(15) . ? N3 C15 1.4236(15) . ? C1 C2 1.3810(18) . ? C1 C6 1.4013(16) . ? C2 C3 1.3856(19) . ? C3 C4 1.3857(18) . ? C4 C5 1.3845(18) . ? C5 C6 1.3956(17) . ? C6 C7 1.4845(17) . ? C8 C9 1.4440(16) . ? C9 C14 1.4083(16) . ? C9 C10 1.4124(16) . ? C10 C11 1.4100(16) . ? C11 C12 1.3691(17) . ? C12 C13 1.3980(18) . ? C13 C14 1.3726(18) . ? C15 C20 1.3894(18) . ? C15 C16 1.3919(17) . ? C16 C17 1.3852(19) . ? C17 C18 1.383(2) . ? C18 C19 1.384(2) . ? C19 C20 1.3833(19) . ? 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 C7 117.91(10) . . ? C7 N2 C10 116.19(9) . . ? C8 N3 C15 125.77(10) . . ? C2 C1 C6 120.51(12) . . ? C1 C2 C3 120.55(12) . . ? C2 C3 C4 119.49(12) . . ? C5 C4 C3 120.33(11) . . ? C4 C5 C6 120.70(11) . . ? C5 C6 C1 118.41(11) . . ? C5 C6 C7 120.28(10) . . ? C1 C6 C7 121.29(11) . . ? N2 C7 N1 126.64(11) . . ? N2 C7 C6 118.32(10) . . ? N1 C7 C6 115.04(10) . . ? N1 C8 N3 118.40(10) . . ? N1 C8 C9 121.47(10) . . ? N3 C8 C9 120.13(10) . . ? C14 C9 C10 119.44(11) . . ? C14 C9 C8 125.18(10) . . ? C10 C9 C8 115.37(10) . . ? N2 C10 C11 118.91(10) . . ? N2 C10 C9 122.21(10) . . ? C11 C10 C9 118.86(11) . . ? C12 C11 C10 120.58(11) . . ? C11 C12 C13 120.48(11) . . ? C14 C13 C12 120.32(11) . . ? C13 C14 C9 120.30(11) . . ? C20 C15 C16 119.43(12) . . ? C20 C15 N3 122.02(10) . . ? C16 C15 N3 118.49(11) . . ? C17 C16 C15 120.09(12) . . ? C18 C17 C16 120.42(12) . . ? C17 C18 C19 119.40(12) . . ? C20 C19 C18 120.72(12) . . ? C19 C20 C15 119.92(11) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.370 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.060