data_in10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H15 N2.50 O0.50' _chemical_formula_weight 238.29 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 ? _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 6.3306(2) _cell_length_b 20.0666(7) _cell_length_c 9.8174(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.713(4) _cell_angle_gamma 90.00 _cell_volume 1194.46(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 506 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9796 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 6830 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2090 _reflns_number_gt 1758 _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^)+(0.0650P)^2^+0.5000P] 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 2090 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.20674(18) 0.01006(6) 0.62533(13) 0.0241(3) Uani 1 1 d . . . C1 C 0.4902(3) 0.07579(7) 0.57778(17) 0.0195(4) Uani 1 1 d . . . C2 C 0.4007(3) 0.03332(7) 0.66820(17) 0.0198(4) Uani 1 1 d . . . C3 C 0.5452(3) 0.01932(8) 0.80669(18) 0.0240(4) Uani 1 1 d . . . H3 H 0.4940 -0.0081 0.8694 0.029 Uiso 1 1 calc R . . C4 C 0.7527(3) 0.04404(8) 0.85090(18) 0.0243(4) Uani 1 1 d . . . H4 H 0.8445 0.0338 0.9435 0.029 Uiso 1 1 calc R . . C5 C 0.8339(2) 0.08512(8) 0.75975(18) 0.0222(4) Uani 1 1 d . . . C6 C 0.7062(3) 0.10056(8) 0.62605(18) 0.0210(4) Uani 1 1 d . . . H6 H 0.7632 0.1279 0.5660 0.025 Uiso 1 1 calc R . . C7 C 0.3604(3) 0.09406(7) 0.43964(18) 0.0205(4) Uani 1 1 d . . . H7 H 0.4267 0.1212 0.3840 0.025 Uiso 1 1 calc R . . N8 N 0.1570(2) 0.07612(6) 0.38425(14) 0.0195(3) Uani 1 1 d . . . H8 H 0.0984 0.0486 0.4330 0.023 Uiso 1 1 calc R . . C9 C 0.0196(3) 0.09878(8) 0.24631(17) 0.0223(4) Uani 1 1 d . . . H9A H -0.0649 0.0605 0.1940 0.027 Uiso 1 1 calc R . . H9B H 0.1151 0.1160 0.1902 0.027 Uiso 1 1 calc R . . C10 C -0.1402(3) 0.15321(8) 0.26073(18) 0.0222(4) Uani 1 1 d . . . C11 C -0.0804(3) 0.19993(8) 0.36951(19) 0.0281(4) Uani 1 1 d . . . H11 H 0.0610 0.1975 0.4371 0.034 Uiso 1 1 calc R . . C12 C -0.2253(4) 0.25017(9) 0.3802(2) 0.0382(5) Uani 1 1 d . . . H12 H -0.1832 0.2818 0.4552 0.046 Uiso 1 1 calc R . . C13 C -0.4315(3) 0.25434(10) 0.2815(3) 0.0434(6) Uani 1 1 d . . . H13 H -0.5311 0.2887 0.2886 0.052 Uiso 1 1 calc R . . C14 C -0.4911(3) 0.20803(10) 0.1724(2) 0.0386(5) Uani 1 1 d . . . H14 H -0.6317 0.2109 0.1040 0.046 Uiso 1 1 calc R . . C15 C -0.3473(3) 0.15759(9) 0.1624(2) 0.0295(4) Uani 1 1 d . . . H15 H -0.3904 0.1258 0.0878 0.035 Uiso 1 1 calc R . . C16 N 1.0538(2) 0.11198(7) 0.81054(16) 0.0280(4) Uani 1 1 d . . . O17 O 1.1700(2) 0.09500(8) 0.92980(15) 0.0420(4) Uani 1 1 d . . . O18 O 1.1179(2) 0.15111(6) 0.73402(15) 0.0362(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0188(6) 0.0290(6) 0.0236(6) 0.0011(5) 0.0046(5) -0.0044(5) C1 0.0183(8) 0.0195(7) 0.0199(9) -0.0031(6) 0.0041(7) 0.0029(6) C2 0.0182(8) 0.0188(7) 0.0236(9) -0.0031(6) 0.0077(7) 0.0017(6) C3 0.0230(9) 0.0278(8) 0.0220(9) 0.0010(6) 0.0079(7) 0.0004(7) C4 0.0211(8) 0.0303(9) 0.0204(9) -0.0034(6) 0.0041(7) 0.0053(7) C5 0.0141(8) 0.0257(8) 0.0258(10) -0.0077(6) 0.0042(7) 0.0000(6) C6 0.0183(8) 0.0222(8) 0.0228(9) -0.0028(6) 0.0066(7) 0.0002(6) C7 0.0203(8) 0.0200(8) 0.0230(9) 0.0003(6) 0.0090(7) 0.0010(6) N8 0.0178(7) 0.0216(7) 0.0188(7) 0.0020(5) 0.0049(6) 0.0010(5) C9 0.0222(8) 0.0274(9) 0.0169(9) 0.0019(6) 0.0049(7) 0.0014(6) C10 0.0224(8) 0.0233(8) 0.0226(9) 0.0075(6) 0.0091(7) 0.0005(6) C11 0.0298(9) 0.0273(9) 0.0279(10) 0.0029(7) 0.0093(8) 0.0034(7) C12 0.0473(12) 0.0260(9) 0.0479(13) 0.0012(8) 0.0241(10) 0.0066(8) C13 0.0412(12) 0.0313(10) 0.0688(16) 0.0235(10) 0.0335(12) 0.0180(8) C14 0.0239(9) 0.0428(11) 0.0489(13) 0.0243(9) 0.0099(9) 0.0059(8) C15 0.0239(9) 0.0332(9) 0.0305(10) 0.0118(7) 0.0066(8) -0.0006(7) C16 0.0178(7) 0.0352(8) 0.0300(9) -0.0096(6) 0.0054(7) -0.0017(6) O17 0.0212(7) 0.0711(10) 0.0273(8) -0.0067(7) -0.0031(6) -0.0034(6) O18 0.0236(7) 0.0373(7) 0.0469(9) -0.0039(6) 0.0086(6) -0.0092(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 C2 1.2668(19) . ? C1 C6 1.403(2) . ? C1 C7 1.417(2) . ? C1 C2 1.458(2) . ? C2 C3 1.431(2) . ? C3 C4 1.354(2) . ? C4 C5 1.417(2) . ? C5 C6 1.365(2) . ? C5 C16 1.441(2) . ? C7 N8 1.296(2) . ? N8 C9 1.456(2) . ? C9 C10 1.523(2) . ? C10 C11 1.389(2) . ? C10 C15 1.390(2) . ? C11 C12 1.387(3) . ? C12 C13 1.387(3) . ? C13 C14 1.386(3) . ? C14 C15 1.383(3) . ? C16 O18 1.233(2) . ? C16 O17 1.238(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C7 118.18(14) . . ? C6 C1 C2 120.89(15) . . ? C7 C1 C2 120.93(14) . . ? O1 C2 C3 122.48(14) . . ? O1 C2 C1 121.50(15) . . ? C3 C2 C1 116.02(14) . . ? C4 C3 C2 121.94(15) . . ? C3 C4 C5 120.35(16) . . ? C6 C5 C4 121.15(15) . . ? C6 C5 C16 119.60(15) . . ? C4 C5 C16 119.24(16) . . ? C5 C6 C1 119.65(15) . . ? N8 C7 C1 124.23(14) . . ? C7 N8 C9 124.00(13) . . ? N8 C9 C10 111.88(13) . . ? C11 C10 C15 119.06(15) . . ? C11 C10 C9 120.91(15) . . ? C15 C10 C9 120.01(15) . . ? C12 C11 C10 120.55(18) . . ? C13 C12 C11 120.09(19) . . ? C14 C13 C12 119.47(17) . . ? C15 C14 C13 120.47(19) . . ? C14 C15 C10 120.36(18) . . ? O18 C16 O17 122.73(15) . . ? O18 C16 C5 118.81(15) . . ? O17 C16 C5 118.46(15) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.336 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.059 data_in11 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H22 N4' _chemical_formula_weight 438.52 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 ? _symmetry_space_group_name_H-M ? 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 16.8348(10) _cell_length_b 16.8841(7) _cell_length_c 17.4604(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.748(7) _cell_angle_gamma 90.00 _cell_volume 4671.1(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 14650 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4101 _reflns_number_gt 3304 _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^)+(0.0500P)^2^+5.0000P] 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 4101 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.49962(8) 0.10040(7) 0.37676(7) 0.0278(3) Uani 1 1 d . . . N2 N 0.53522(8) 0.05002(7) 0.33780(7) 0.0272(3) Uani 1 1 d . . . C3 C 0.59820(9) 0.01076(8) 0.39379(8) 0.0245(3) Uani 1 1 d . . . C4 C 0.60230(9) 0.03664(9) 0.47040(8) 0.0259(3) Uani 1 1 d . . . H4 H 0.6401 0.0188 0.5213 0.031 Uiso 1 1 calc R . . C5 C 0.54021(9) 0.09385(9) 0.45776(8) 0.0245(3) Uani 1 1 d . . . C6 C 0.65330(9) -0.04480(9) 0.37130(9) 0.0265(3) Uani 1 1 d . . . C7 C 0.67920(10) -0.03004(9) 0.30512(9) 0.0311(4) Uani 1 1 d . . . H7 H 0.6572 0.0143 0.2711 0.037 Uiso 1 1 calc R . . C8 C 0.73665(11) -0.07926(11) 0.28843(10) 0.0388(4) Uani 1 1 d . . . H8 H 0.7543 -0.0684 0.2432 0.047 Uiso 1 1 calc R . . C9 C 0.76861(11) -0.14405(11) 0.33701(11) 0.0434(5) Uani 1 1 d . . . H9 H 0.8089 -0.1774 0.3260 0.052 Uiso 1 1 calc R . . C10 C 0.74168(12) -0.16013(11) 0.40167(11) 0.0451(5) Uani 1 1 d . . . H10 H 0.7626 -0.2054 0.4346 0.054 Uiso 1 1 calc R . . C11 C 0.68479(11) -0.11121(10) 0.41888(10) 0.0356(4) Uani 1 1 d . . . H11 H 0.6668 -0.1228 0.4637 0.043 Uiso 1 1 calc R . . C12 C 0.52002(9) 0.14490(9) 0.51646(9) 0.0260(3) Uani 1 1 d . . . C13 C 0.47350(10) 0.21417(9) 0.49269(9) 0.0335(4) Uani 1 1 d . . . H13 H 0.4532 0.2287 0.4368 0.040 Uiso 1 1 calc R . . C14 C 0.45650(11) 0.26205(10) 0.54928(10) 0.0394(4) Uani 1 1 d . . . H14 H 0.4244 0.3090 0.5321 0.047 Uiso 1 1 calc R . . C15 C 0.48604(11) 0.24194(10) 0.63095(10) 0.0381(4) Uani 1 1 d . . . H15 H 0.4737 0.2746 0.6698 0.046 Uiso 1 1 calc R . . C16 C 0.53343(11) 0.17417(10) 0.65548(10) 0.0353(4) Uani 1 1 d . . . H16 H 0.5549 0.1607 0.7116 0.042 Uiso 1 1 calc R . . C17 C 0.54988(10) 0.12577(10) 0.59892(9) 0.0297(4) Uani 1 1 d . . . H17 H 0.5820 0.0788 0.6164 0.036 Uiso 1 1 calc R . . N1A N 0.37361(7) 0.18873(7) 0.26341(7) 0.0253(3) Uani 1 1 d . . . N2A N 0.40941(8) 0.23763(7) 0.22359(7) 0.0252(3) Uani 1 1 d . . . C3A C 0.34771(9) 0.27119(8) 0.16106(8) 0.0232(3) Uani 1 1 d . . . C4A C 0.27078(9) 0.24273(9) 0.16150(8) 0.0255(3) Uani 1 1 d . . . H4A H 0.2165 0.2561 0.1247 0.031 Uiso 1 1 calc R . . C5A C 0.28915(9) 0.19074(8) 0.22664(8) 0.0241(3) Uani 1 1 d . . . C6A C 0.36770(10) 0.32876(8) 0.10761(9) 0.0260(3) Uani 1 1 d . . . C7A C 0.44975(10) 0.35594(9) 0.12382(10) 0.0330(4) Uani 1 1 d . . . H7A H 0.4937 0.3368 0.1702 0.040 Uiso 1 1 calc R . . C8A C 0.46783(12) 0.41019(11) 0.07334(11) 0.0421(4) Uani 1 1 d . . . H8A H 0.5241 0.4282 0.0848 0.050 Uiso 1 1 calc R . . C9A C 0.40420(13) 0.43851(11) 0.00588(11) 0.0441(5) Uani 1 1 d . . . H9A H 0.4166 0.4763 -0.0288 0.053 Uiso 1 1 calc R . . C10A C 0.32276(12) 0.41184(10) -0.01104(10) 0.0405(4) Uani 1 1 d . . . H10A H 0.2791 0.4311 -0.0576 0.049 Uiso 1 1 calc R . . C11A C 0.30433(11) 0.35732(9) 0.03927(9) 0.0331(4) Uani 1 1 d . . . H11A H 0.2480 0.3391 0.0272 0.040 Uiso 1 1 calc R . . C12A C 0.23350(9) 0.14289(9) 0.25653(9) 0.0264(3) Uani 1 1 d . . . C13A C 0.25972(10) 0.11335(10) 0.33563(10) 0.0353(4) Uani 1 1 d . . . H13A H 0.3144 0.1259 0.3721 0.042 Uiso 1 1 calc R . . C14A C 0.20699(11) 0.06618(11) 0.36127(12) 0.0429(4) Uani 1 1 d . . . H14A H 0.2254 0.0466 0.4155 0.052 Uiso 1 1 calc R . . C15A C 0.12742(11) 0.04704(11) 0.30867(12) 0.0445(5) Uani 1 1 d . . . H15A H 0.0916 0.0134 0.3261 0.053 Uiso 1 1 calc R . . C16A C 0.10044(11) 0.07732(11) 0.23062(12) 0.0444(4) Uani 1 1 d . . . H16A H 0.0455 0.0650 0.1945 0.053 Uiso 1 1 calc R . . C17A C 0.15252(10) 0.12524(10) 0.20485(10) 0.0346(4) Uani 1 1 d . . . H17A H 0.1330 0.1464 0.1513 0.042 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 0.0293(7) 0.0331(7) 0.0195(6) 0.0018(5) 0.0063(5) -0.0007(6) N2 0.0242(7) 0.0311(7) 0.0230(6) 0.0036(5) 0.0039(5) -0.0003(5) C3 0.0222(7) 0.0264(7) 0.0220(7) 0.0034(6) 0.0036(6) -0.0022(6) C4 0.0240(7) 0.0307(8) 0.0190(7) 0.0047(6) 0.0020(6) 0.0004(6) C5 0.0236(7) 0.0291(8) 0.0190(7) 0.0036(6) 0.0048(6) -0.0026(6) C6 0.0239(7) 0.0280(8) 0.0234(7) -0.0031(6) 0.0026(6) -0.0039(6) C7 0.0314(8) 0.0331(8) 0.0254(8) -0.0026(6) 0.0051(7) -0.0044(7) C8 0.0377(9) 0.0475(10) 0.0330(9) -0.0114(8) 0.0141(8) -0.0033(8) C9 0.0382(10) 0.0448(10) 0.0453(10) -0.0142(8) 0.0116(8) 0.0066(8) C10 0.0498(11) 0.0372(9) 0.0443(10) 0.0019(8) 0.0108(9) 0.0135(8) C11 0.0391(9) 0.0337(9) 0.0329(8) 0.0035(7) 0.0107(7) 0.0053(7) C12 0.0239(8) 0.0298(8) 0.0233(7) 0.0015(6) 0.0067(6) -0.0027(6) C13 0.0380(9) 0.0345(8) 0.0253(8) 0.0038(6) 0.0073(7) 0.0017(7) C14 0.0450(10) 0.0322(9) 0.0409(10) -0.0006(7) 0.0142(8) 0.0055(8) C15 0.0420(10) 0.0395(9) 0.0341(9) -0.0089(7) 0.0148(8) -0.0026(8) C16 0.0368(9) 0.0450(10) 0.0231(8) -0.0012(7) 0.0088(7) -0.0016(8) C17 0.0280(8) 0.0356(8) 0.0238(8) 0.0022(6) 0.0064(6) 0.0011(7) N1A 0.0208(6) 0.0305(7) 0.0245(6) 0.0013(5) 0.0074(5) 0.0007(5) N2A 0.0252(6) 0.0280(6) 0.0220(6) 0.0032(5) 0.0074(5) 0.0033(5) C3A 0.0251(8) 0.0240(7) 0.0197(7) 0.0001(5) 0.0065(6) 0.0048(6) C4A 0.0210(7) 0.0308(8) 0.0218(7) 0.0020(6) 0.0033(6) 0.0040(6) C5A 0.0213(7) 0.0262(7) 0.0237(7) -0.0013(6) 0.0062(6) 0.0023(6) C6A 0.0311(8) 0.0249(7) 0.0232(7) 0.0002(6) 0.0108(6) 0.0045(6) C7A 0.0327(9) 0.0350(9) 0.0313(8) 0.0035(7) 0.0108(7) 0.0003(7) C8A 0.0455(10) 0.0409(10) 0.0444(10) 0.0058(8) 0.0214(9) -0.0049(8) C9A 0.0612(12) 0.0386(9) 0.0413(10) 0.0115(8) 0.0286(9) 0.0009(9) C10A 0.0489(11) 0.0429(10) 0.0306(9) 0.0126(7) 0.0145(8) 0.0127(8) C11A 0.0340(9) 0.0369(9) 0.0291(8) 0.0067(7) 0.0116(7) 0.0074(7) C12A 0.0226(8) 0.0268(8) 0.0307(8) 0.0021(6) 0.0104(6) 0.0049(6) C13A 0.0254(8) 0.0428(9) 0.0356(9) 0.0117(7) 0.0076(7) 0.0033(7) C14A 0.0328(9) 0.0492(10) 0.0499(11) 0.0230(9) 0.0181(8) 0.0091(8) C15A 0.0331(10) 0.0426(10) 0.0648(12) 0.0149(9) 0.0258(9) 0.0023(8) C16A 0.0243(8) 0.0546(11) 0.0538(11) 0.0012(9) 0.0127(8) -0.0054(8) C17A 0.0251(8) 0.0451(9) 0.0337(9) 0.0033(7) 0.0099(7) 0.0001(7) _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 N2 1.3495(18) . ? N1 C5 1.3513(18) . ? N2 C3 1.3487(18) . ? C3 C4 1.387(2) . ? C3 C6 1.463(2) . ? C4 C5 1.385(2) . ? C5 C12 1.464(2) . ? C6 C7 1.389(2) . ? C6 C11 1.390(2) . ? C7 C8 1.379(2) . ? C8 C9 1.377(3) . ? C9 C10 1.378(3) . ? C10 C11 1.373(2) . ? C12 C13 1.391(2) . ? C12 C17 1.393(2) . ? C13 C14 1.379(2) . ? C14 C15 1.384(2) . ? C15 C16 1.378(2) . ? C16 C17 1.380(2) . ? N1A N2A 1.3460(17) . ? N1A C5A 1.3484(18) . ? N2A C3A 1.3511(18) . ? C3A C4A 1.384(2) . ? C3A C6A 1.463(2) . ? C4A C5A 1.386(2) . ? C5A C12A 1.461(2) . ? C6A C11A 1.391(2) . ? C6A C7A 1.391(2) . ? C7A C8A 1.375(2) . ? C8A C9A 1.382(3) . ? C9A C10A 1.377(3) . ? C10A C11A 1.378(2) . ? C12A C17A 1.389(2) . ? C12A C13A 1.393(2) . ? C13A C14A 1.375(2) . ? C14A C15A 1.382(3) . ? C15A C16A 1.381(3) . ? C16A C17A 1.376(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C5 108.81(12) . . ? C3 N2 N1 108.58(12) . . ? N2 C3 C4 108.37(13) . . ? N2 C3 C6 122.34(13) . . ? C4 C3 C6 129.17(13) . . ? C5 C4 C3 106.09(12) . . ? N1 C5 C4 108.14(13) . . ? N1 C5 C12 121.97(13) . . ? C4 C5 C12 129.80(13) . . ? C7 C6 C11 118.60(15) . . ? C7 C6 C3 120.94(14) . . ? C11 C6 C3 120.35(14) . . ? C8 C7 C6 120.50(15) . . ? C9 C8 C7 120.30(17) . . ? C8 C9 C10 119.52(17) . . ? C11 C10 C9 120.51(17) . . ? C10 C11 C6 120.55(16) . . ? C13 C12 C17 118.27(14) . . ? C13 C12 C5 121.78(13) . . ? C17 C12 C5 119.93(13) . . ? C14 C13 C12 120.75(14) . . ? C13 C14 C15 120.32(16) . . ? C16 C15 C14 119.51(16) . . ? C15 C16 C17 120.29(15) . . ? C16 C17 C12 120.85(15) . . ? N2A N1A C5A 108.84(11) . . ? N1A N2A C3A 108.56(12) . . ? N2A C3A C4A 108.39(12) . . ? N2A C3A C6A 120.94(13) . . ? C4A C3A C6A 130.66(13) . . ? C3A C4A C5A 105.94(12) . . ? N1A C5A C4A 108.28(13) . . ? N1A C5A C12A 121.09(13) . . ? C4A C5A C12A 130.63(13) . . ? C11A C6A C7A 118.76(14) . . ? C11A C6A C3A 120.17(14) . . ? C7A C6A C3A 121.07(13) . . ? C8A C7A C6A 120.61(15) . . ? C7A C8A C9A 120.08(17) . . ? C10A C9A C8A 119.90(16) . . ? C9A C10A C11A 120.25(16) . . ? C10A C11A C6A 120.40(16) . . ? C17A C12A C13A 118.68(15) . . ? C17A C12A C5A 119.58(14) . . ? C13A C12A C5A 121.73(14) . . ? C14A C13A C12A 120.48(16) . . ? C13A C14A C15A 120.42(17) . . ? C16A C15A C14A 119.40(16) . . ? C17A C16A C15A 120.47(16) . . ? C16A C17A C12A 120.51(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.389 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.039