Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email SUGA@PENTACLE.C.U-TOKYO.AC.JP _publ_contact_author_name 'Prof Tadashi Sugawara' _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name T.Sugawara I.Chung A.Izuoka Y.Kawada M.M.Matsushita ; J.Nakazaki ; R.Watanabe data_1 _database_code_CSD 199203 #------------------------------------------------------------------------------ _audit_creation_date 'Mon Nov 25 20:01:24 2002' _audit_creation_method SHELXL-97 _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ? _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_publication_material ? _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common 1-pyrrolylNN _chemical_formula_weight 222.27 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H16 N3 O2' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 9.8453(16) _cell_length_b 16.530(3) _cell_length_c 7.2587(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.531(11) _cell_angle_gamma 90.00 _cell_volume 1173.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.0 _cell_measurement_theta_max 25.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? 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' #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max .44 _exptl_crystal_size_mid .40 _exptl_crystal_size_min .32 _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_meas 'not measured' _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 298.2 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% ? _diffrn_reflns_number 2870 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 1.2803 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.990 _reflns_number_total 2667 _reflns_number_gt 1788 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ 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' #------------------------------------------------------------------------------ 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 0.18888(14) 1.18008(7) -0.13844(18) 0.0688(4) Uani 1 1 d . . . O2 O 0.40934(15) 0.98037(7) 0.2260(2) 0.0736(4) Uani 1 1 d . . . N1 N 0.19400(13) 1.00772(7) -0.06940(17) 0.0451(3) Uani 1 1 d . . . N2 N 0.27075(13) 1.14510(7) -0.01323(18) 0.0459(3) Uani 1 1 d . . . N3 N 0.37326(14) 1.05012(7) 0.16294(19) 0.0480(4) Uani 1 1 d . . . C1 C 0.14029(18) 1.00998(12) -0.2543(2) 0.0547(4) Uani 1 1 d . . . C2 C 0.0652(2) 0.94219(12) -0.2894(3) 0.0628(5) Uani 1 1 d . . . C3 C 0.07023(19) 0.89747(11) -0.1239(3) 0.0608(5) Uani 1 1 d . . . C4 C 0.14940(19) 0.93767(10) 0.0087(3) 0.0543(4) Uani 1 1 d . . . C5 C 0.27608(15) 1.06561(9) 0.0227(2) 0.0420(4) Uani 1 1 d . . . C6 C 0.38709(15) 1.18862(9) 0.0963(2) 0.0454(4) Uani 1 1 d . . . C7 C 0.42623(16) 1.12689(9) 0.2539(2) 0.0452(4) Uani 1 1 d . . . C8 C 0.4966(2) 1.20043(14) -0.0331(3) 0.0654(5) Uani 1 1 d . . . C9 C 0.3404(2) 1.27037(11) 0.1600(3) 0.0665(5) Uani 1 1 d . . . C10 C 0.3494(3) 1.13716(17) 0.4238(3) 0.0736(6) Uani 1 1 d . . . C11 C 0.5782(2) 1.11880(14) 0.3131(4) 0.0705(6) Uani 1 1 d . . . H1 H 0.158(2) 1.0533(13) -0.327(3) 0.067(6) Uiso 1 1 d . . . H2 H 0.020(2) 0.9283(13) -0.407(3) 0.076(6) Uiso 1 1 d . . . H3 H 0.023(2) 0.8468(13) -0.106(3) 0.073(6) Uiso 1 1 d . . . H4 H 0.175(2) 0.9260(13) 0.130(3) 0.075(6) Uiso 1 1 d . . . H5 H 0.575(2) 1.2258(13) 0.032(3) 0.073(6) Uiso 1 1 d . . . H6 H 0.453(2) 1.2290(14) -0.139(3) 0.083(7) Uiso 1 1 d . . . H7 H 0.527(2) 1.1458(14) -0.070(3) 0.072(6) Uiso 1 1 d . . . H8 H 0.259(3) 1.2630(15) 0.215(3) 0.093(8) Uiso 1 1 d . . . H9 H 0.317(2) 1.3065(13) 0.048(3) 0.070(5) Uiso 1 1 d . . . H10 H 0.416(2) 1.2964(14) 0.242(3) 0.084(7) Uiso 1 1 d . . . H11 H 0.375(3) 1.1855(18) 0.487(4) 0.106(9) Uiso 1 1 d . . . H12 H 0.370(2) 1.0933(14) 0.509(3) 0.082(7) Uiso 1 1 d . . . H13 H 0.241(3) 1.1442(15) 0.381(3) 0.099(8) Uiso 1 1 d . . . H14 H 0.594(2) 1.0802(15) 0.415(3) 0.085(7) Uiso 1 1 d . . . H15 H 0.614(2) 1.1730(15) 0.355(3) 0.085(7) Uiso 1 1 d . . . H16 H 0.628(3) 1.1027(16) 0.201(4) 0.105(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0747(8) 0.0473(7) 0.0757(9) 0.0153(6) -0.0291(7) 0.0023(6) O2 0.0956(10) 0.0372(6) 0.0789(9) 0.0117(6) -0.0302(7) 0.0043(6) N1 0.0500(7) 0.0394(7) 0.0443(7) 0.0019(5) -0.0020(6) -0.0054(5) N2 0.0489(7) 0.0365(6) 0.0495(7) 0.0063(5) -0.0064(6) 0.0011(5) N3 0.0578(8) 0.0347(7) 0.0482(7) 0.0048(6) -0.0079(6) 0.0008(6) C1 0.0564(10) 0.0577(10) 0.0472(9) 0.0039(8) -0.0059(8) -0.0071(8) C2 0.0592(10) 0.0626(11) 0.0626(11) -0.0106(9) -0.0113(9) -0.0058(9) C3 0.0604(10) 0.0449(9) 0.0761(13) -0.0038(9) 0.0031(9) -0.0111(8) C4 0.0656(11) 0.0419(8) 0.0548(10) 0.0040(8) 0.0038(9) -0.0087(8) C5 0.0479(8) 0.0350(7) 0.0418(8) 0.0025(6) -0.0007(6) -0.0004(6) C6 0.0476(8) 0.0366(8) 0.0499(9) -0.0006(6) -0.0028(7) -0.0016(6) C7 0.0509(8) 0.0377(7) 0.0445(8) -0.0023(6) -0.0047(7) -0.0012(6) C8 0.0678(12) 0.0595(12) 0.0691(13) 0.0084(10) 0.0095(11) -0.0123(10) C9 0.0736(13) 0.0381(9) 0.0837(14) -0.0061(9) -0.0086(12) 0.0090(9) C10 0.0996(18) 0.0729(14) 0.0491(11) -0.0021(11) 0.0121(11) -0.0032(12) C11 0.0590(11) 0.0570(12) 0.0887(16) 0.0099(11) -0.0212(11) -0.0014(9) #------------------------------------------------------------------------------ _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^)+(0.0778P)^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 SHELXL _refine_ls_extinction_coef 0.007(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2667 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1335 _refine_ls_wR_factor_gt 0.1241 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.177 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.031 #------------------------------------------------------------------------------ _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 N2 1.2820(16) . ? O2 N3 1.2759(16) . ? N1 C5 1.3758(19) . ? N1 C4 1.383(2) . ? N1 C1 1.386(2) . ? N2 C5 1.3396(18) . ? N2 C6 1.5015(19) . ? N3 C5 1.3400(19) . ? N3 C7 1.4966(19) . ? C1 C2 1.350(3) . ? C1 H1 0.92(2) . ? C2 C3 1.407(3) . ? C2 H2 0.94(2) . ? C3 C4 1.343(3) . ? C3 H3 0.97(2) . ? C4 H4 0.91(2) . ? C6 C9 1.516(2) . ? C6 C8 1.521(3) . ? C6 C7 1.549(2) . ? C7 C11 1.515(3) . ? C7 C10 1.528(3) . ? C8 H5 0.95(2) . ? C8 H6 0.96(2) . ? C8 H7 1.00(2) . ? C9 H8 0.95(3) . ? C9 H9 1.01(2) . ? C9 H10 1.00(2) . ? C10 H11 0.94(3) . ? C10 H12 0.96(2) . ? C10 H13 1.08(3) . ? C11 H14 0.97(2) . ? C11 H15 1.00(2) . ? C11 H16 1.03(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 C5 N1 C4 125.43(14) . . ? C5 N1 C1 126.16(14) . . ? C4 N1 C1 108.40(14) . . ? O1 N2 C5 126.02(13) . . ? O1 N2 C6 122.65(12) . . ? C5 N2 C6 110.87(12) . . ? O2 N3 C5 126.20(13) . . ? O2 N3 C7 122.63(12) . . ? C5 N3 C7 110.85(11) . . ? C2 C1 N1 107.46(17) . . ? C2 C1 H1 132.6(13) . . ? N1 C1 H1 120.0(13) . . ? C1 C2 C3 108.07(17) . . ? C1 C2 H2 124.2(14) . . ? C3 C2 H2 127.7(14) . . ? C4 C3 C2 108.22(16) . . ? C4 C3 H3 125.3(12) . . ? C2 C3 H3 126.5(12) . . ? C3 C4 N1 107.83(17) . . ? C3 C4 H4 131.4(14) . . ? N1 C4 H4 120.8(14) . . ? N3 C5 N2 110.13(13) . . ? N3 C5 N1 124.43(13) . . ? N2 C5 N1 125.44(13) . . ? N2 C6 C9 110.43(14) . . ? N2 C6 C8 106.64(14) . . ? C9 C6 C8 109.55(16) . . ? N2 C6 C7 100.73(11) . . ? C9 C6 C7 114.88(14) . . ? C8 C6 C7 113.97(14) . . ? N3 C7 C11 109.49(15) . . ? N3 C7 C10 105.69(15) . . ? C11 C7 C10 110.17(17) . . ? N3 C7 C6 100.84(11) . . ? C11 C7 C6 114.99(15) . . ? C10 C7 C6 114.74(15) . . ? C6 C8 H5 109.9(13) . . ? C6 C8 H6 105.6(14) . . ? H5 C8 H6 116.3(19) . . ? C6 C8 H7 107.6(12) . . ? H5 C8 H7 106.5(18) . . ? H6 C8 H7 110.6(18) . . ? C6 C9 H8 108.4(16) . . ? C6 C9 H9 109.3(11) . . ? H8 C9 H9 107(2) . . ? C6 C9 H10 109.5(13) . . ? H8 C9 H10 115(2) . . ? H9 C9 H10 107.8(17) . . ? C7 C10 H11 110.8(17) . . ? C7 C10 H12 110.5(14) . . ? H11 C10 H12 108(2) . . ? C7 C10 H13 110.0(13) . . ? H11 C10 H13 105(2) . . ? H12 C10 H13 113(2) . . ? C7 C11 H14 110.0(14) . . ? C7 C11 H15 108.1(13) . . ? H14 C11 H15 109.7(17) . . ? C7 C11 H16 109.9(15) . . ? H14 C11 H16 112(2) . . ? H15 C11 H16 107(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 C2 -179.66(16) . . . . ? C4 N1 C1 C2 -0.6(2) . . . . ? N1 C1 C2 C3 0.9(2) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C2 C3 C4 N1 0.5(2) . . . . ? C5 N1 C4 C3 179.11(15) . . . . ? C1 N1 C4 C3 0.0(2) . . . . ? O2 N3 C5 N2 -176.44(16) . . . . ? C7 N3 C5 N2 9.89(18) . . . . ? O2 N3 C5 N1 3.8(3) . . . . ? C7 N3 C5 N1 -169.89(14) . . . . ? O1 N2 C5 N3 -179.76(15) . . . . ? C6 N2 C5 N3 7.86(18) . . . . ? O1 N2 C5 N1 0.0(3) . . . . ? C6 N2 C5 N1 -172.37(14) . . . . ? C4 N1 C5 N3 32.5(2) . . . . ? C1 N1 C5 N3 -148.52(17) . . . . ? C4 N1 C5 N2 -147.20(17) . . . . ? C1 N1 C5 N2 31.7(3) . . . . ? O1 N2 C6 C9 44.6(2) . . . . ? C5 N2 C6 C9 -142.76(16) . . . . ? O1 N2 C6 C8 -74.38(19) . . . . ? C5 N2 C6 C8 98.30(16) . . . . ? O1 N2 C6 C7 166.41(14) . . . . ? C5 N2 C6 C7 -20.92(16) . . . . ? O2 N3 C7 C11 42.3(2) . . . . ? C5 N3 C7 C11 -143.75(17) . . . . ? O2 N3 C7 C10 -76.3(2) . . . . ? C5 N3 C7 C10 97.61(17) . . . . ? O2 N3 C7 C6 163.92(16) . . . . ? C5 N3 C7 C6 -22.15(16) . . . . ? N2 C6 C7 N3 24.03(14) . . . . ? C9 C6 C7 N3 142.68(15) . . . . ? C8 C6 C7 N3 -89.75(16) . . . . ? N2 C6 C7 C11 141.67(16) . . . . ? C9 C6 C7 C11 -99.7(2) . . . . ? C8 C6 C7 C11 27.9(2) . . . . ? N2 C6 C7 C10 -89.02(17) . . . . ? C9 C6 C7 C10 29.6(2) . . . . ? C8 C6 C7 C10 157.21(17) . . . . ? #==END data_2 _database_code_CSD 199204 #------------------------------------------------------------------------------ _audit_creation_date 'Mon Nov 25 20:01:24 2002' _audit_creation_method SHELXL-97 _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT & SADABS' _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_publication_material ? _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common 2-pyrrolylNN _chemical_formula_weight 222.27 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H16 N3 O2' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 9.925(2) _cell_length_b 9.317(2) _cell_length_c 12.972(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.905(4) _cell_angle_gamma 90.00 _cell_volume 1141.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 288(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.0 _cell_measurement_theta_max 25.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? 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' #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type 'empirical (sadabs)' _exptl_absorpt_correction_T_min 0.9820 _exptl_absorpt_correction_T_max 0.9820 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 288(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'omega scan' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7247 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.19 _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 28.19 _diffrn_measured_fraction_theta_full 0.920 _reflns_number_total 2584 _reflns_number_gt 1889 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ 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' #------------------------------------------------------------------------------ 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 0.33129(16) 0.62156(14) 0.46359(8) 0.0872(4) Uani 1 1 d . . . O2 O 0.16878(14) 0.62983(13) 0.09279(8) 0.0833(4) Uani 1 1 d . . . N1 N 0.33331(12) 0.86219(12) 0.18503(9) 0.0490(3) Uani 1 1 d . . . N2 N 0.26749(13) 0.58435(12) 0.36611(9) 0.0545(3) Uani 1 1 d . . . N3 N 0.19073(12) 0.58772(12) 0.19015(9) 0.0524(3) Uani 1 1 d . . . C1 C 0.33725(12) 0.79264(13) 0.27880(10) 0.0430(3) Uani 1 1 d . . . C2 C 0.41528(15) 0.87614(16) 0.36380(13) 0.0544(4) Uani 1 1 d . . . C3 C 0.45833(16) 0.99748(16) 0.31872(13) 0.0600(4) Uani 1 1 d . . . C4 C 0.40703(16) 0.98587(16) 0.20968(14) 0.0573(4) Uani 1 1 d . . . C5 C 0.26667(12) 0.65883(13) 0.27822(9) 0.0428(3) Uani 1 1 d . . . C6 C 0.19182(15) 0.44411(14) 0.34061(12) 0.0526(4) Uani 1 1 d . . . C7 C 0.12720(15) 0.45262(15) 0.21516(12) 0.0554(4) Uani 1 1 d . . . C8 C 0.3028(2) 0.3282(2) 0.3802(2) 0.0844(6) Uani 1 1 d . . . C9 C 0.0855(2) 0.4362(3) 0.40318(19) 0.0834(6) Uani 1 1 d . . . C10 C -0.0323(2) 0.4725(4) 0.1749(2) 0.1029(9) Uani 1 1 d . . . C11 C 0.1723(5) 0.3336(2) 0.1525(2) 0.1063(10) Uani 1 1 d . . . H1 H 0.286(2) 0.830(2) 0.1138(16) 0.085(5) Uiso 1 1 d . . . H2 H 0.4292(17) 0.855(2) 0.4370(15) 0.069(5) Uiso 1 1 d . . . H3 H 0.5194(19) 1.0787(18) 0.3588(14) 0.077(5) Uiso 1 1 d . . . H4 H 0.4143(17) 1.0429(17) 0.1543(14) 0.060(4) Uiso 1 1 d . . . H5 H 0.2554(18) 0.232(2) 0.3661(16) 0.090(6) Uiso 1 1 d . . . H6 H 0.376(3) 0.336(3) 0.342(2) 0.128(9) Uiso 1 1 d . . . H7 H 0.348(2) 0.338(2) 0.4632(19) 0.101(7) Uiso 1 1 d . . . H8 H 0.134(2) 0.443(2) 0.485(2) 0.104(7) Uiso 1 1 d . . . H9 H 0.026(2) 0.527(2) 0.3890(17) 0.091(6) Uiso 1 1 d . . . H10 H 0.027(3) 0.353(3) 0.3835(19) 0.115(8) Uiso 1 1 d . . . H11 H -0.051(3) 0.554(3) 0.223(2) 0.128(10) Uiso 1 1 d . . . H12 H -0.059(3) 0.493(3) 0.103(3) 0.125(9) Uiso 1 1 d . . . H13 H -0.072(3) 0.384(3) 0.188(2) 0.132(10) Uiso 1 1 d . . . H14 H 0.144(3) 0.254(3) 0.174(2) 0.123(8) Uiso 1 1 d . . . H15 H 0.129(2) 0.347(3) 0.070(2) 0.108(7) Uiso 1 1 d . . . H16 H 0.264(4) 0.321(5) 0.169(4) 0.20(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.1447(11) 0.0796(8) 0.0336(6) -0.0050(5) 0.0218(6) -0.0263(8) O2 0.1172(10) 0.0817(8) 0.0351(6) 0.0056(5) -0.0002(6) -0.0314(7) N1 0.0575(7) 0.0504(6) 0.0382(7) 0.0016(5) 0.0133(5) 0.0006(5) N2 0.0765(8) 0.0535(7) 0.0361(6) -0.0027(5) 0.0214(5) -0.0057(5) N3 0.0597(7) 0.0551(7) 0.0382(6) 0.0011(5) 0.0085(5) -0.0063(5) C1 0.0469(6) 0.0460(7) 0.0370(7) -0.0010(5) 0.0140(5) 0.0057(5) C2 0.0644(8) 0.0566(8) 0.0413(8) -0.0066(6) 0.0150(6) -0.0021(6) C3 0.0663(9) 0.0519(8) 0.0628(10) -0.0095(7) 0.0214(7) -0.0064(7) C4 0.0657(9) 0.0484(8) 0.0612(10) 0.0047(7) 0.0244(7) -0.0012(6) C5 0.0474(6) 0.0473(7) 0.0347(7) -0.0014(5) 0.0142(5) 0.0040(5) C6 0.0591(7) 0.0497(7) 0.0532(8) 0.0041(6) 0.0234(6) -0.0011(6) C7 0.0630(8) 0.0535(8) 0.0521(9) -0.0052(6) 0.0211(7) -0.0117(6) C8 0.0796(12) 0.0590(11) 0.1001(17) -0.0019(10) 0.0065(12) 0.0089(9) C9 0.0815(12) 0.1120(17) 0.0681(13) 0.0163(12) 0.0398(10) -0.0028(12) C10 0.0629(11) 0.168(3) 0.0692(14) 0.0056(16) 0.0071(10) -0.0332(14) C11 0.197(3) 0.0592(11) 0.0839(17) -0.0119(11) 0.075(2) -0.0072(15) #------------------------------------------------------------------------------ _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^)+(0.0956P)^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 SHELXL _refine_ls_extinction_coef 0.012(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2584 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1588 _refine_ls_wR_factor_gt 0.1509 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.223 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.037 #------------------------------------------------------------------------------ _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 N2 1.2758(15) . ? O2 N3 1.2756(15) . ? N1 C4 1.3496(19) . ? N1 C1 1.3681(17) . ? N1 H1 0.95(2) . ? N2 C5 1.3326(17) . ? N2 C6 1.4926(18) . ? N3 C5 1.3352(16) . ? N3 C7 1.4877(18) . ? C1 C2 1.3768(18) . ? C1 C5 1.4289(19) . ? C2 C3 1.399(2) . ? C2 H2 0.937(19) . ? C3 C4 1.352(2) . ? C3 H3 1.008(18) . ? C4 H4 0.914(18) . ? C6 C8 1.515(2) . ? C6 C9 1.518(2) . ? C6 C7 1.557(2) . ? C7 C10 1.518(3) . ? C7 C11 1.522(3) . ? C8 H5 1.00(2) . ? C8 H6 1.00(3) . ? C8 H7 1.04(2) . ? C9 H8 1.02(3) . ? C9 H9 1.02(2) . ? C9 H10 0.95(3) . ? C10 H11 1.04(3) . ? C10 H12 0.91(3) . ? C10 H13 0.95(3) . ? C11 H14 0.87(3) . ? C11 H15 1.03(3) . ? C11 H16 0.88(4) . ? 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 C4 N1 C1 109.18(12) . . ? C4 N1 H1 124.9(12) . . ? C1 N1 H1 126.0(12) . . ? O1 N2 C5 125.25(12) . . ? O1 N2 C6 121.34(11) . . ? C5 N2 C6 113.32(11) . . ? O2 N3 C5 125.05(12) . . ? O2 N3 C7 121.42(11) . . ? C5 N3 C7 113.51(11) . . ? N1 C1 C2 107.44(13) . . ? N1 C1 C5 121.91(11) . . ? C2 C1 C5 130.64(12) . . ? C1 C2 C3 106.91(14) . . ? C1 C2 H2 124.5(11) . . ? C3 C2 H2 128.5(11) . . ? C4 C3 C2 107.90(13) . . ? C4 C3 H3 124.9(10) . . ? C2 C3 H3 127.1(10) . . ? N1 C4 C3 108.57(14) . . ? N1 C4 H4 118.6(10) . . ? C3 C4 H4 132.8(10) . . ? N2 C5 N3 109.09(12) . . ? N2 C5 C1 125.16(11) . . ? N3 C5 C1 125.75(11) . . ? N2 C6 C8 106.57(14) . . ? N2 C6 C9 108.01(15) . . ? C8 C6 C9 109.68(18) . . ? N2 C6 C7 101.81(10) . . ? C8 C6 C7 114.41(15) . . ? C9 C6 C7 115.51(14) . . ? N3 C7 C10 106.80(17) . . ? N3 C7 C11 106.63(15) . . ? C10 C7 C11 110.6(2) . . ? N3 C7 C6 101.83(10) . . ? C10 C7 C6 114.61(15) . . ? C11 C7 C6 115.28(18) . . ? C6 C8 H5 108.8(11) . . ? C6 C8 H6 110.3(15) . . ? H5 C8 H6 110(2) . . ? C6 C8 H7 108.9(12) . . ? H5 C8 H7 107.4(18) . . ? H6 C8 H7 111.2(18) . . ? C6 C9 H8 111.4(14) . . ? C6 C9 H9 108.8(12) . . ? H8 C9 H9 101.7(17) . . ? C6 C9 H10 111.2(15) . . ? H8 C9 H10 112(2) . . ? H9 C9 H10 111(2) . . ? C7 C10 H11 104.0(14) . . ? C7 C10 H12 108.7(17) . . ? H11 C10 H12 115(2) . . ? C7 C10 H13 106.4(17) . . ? H11 C10 H13 111(2) . . ? H12 C10 H13 111(2) . . ? C7 C11 H14 106.2(19) . . ? C7 C11 H15 111.9(14) . . ? H14 C11 H15 111(2) . . ? C7 C11 H16 115(3) . . ? H14 C11 H16 103(4) . . ? H15 C11 H16 110(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 0.22(15) . . . . ? C4 N1 C1 C5 179.25(12) . . . . ? N1 C1 C2 C3 -0.10(15) . . . . ? C5 C1 C2 C3 -179.02(13) . . . . ? C1 C2 C3 C4 -0.04(17) . . . . ? C1 N1 C4 C3 -0.25(16) . . . . ? C2 C3 C4 N1 0.18(17) . . . . ? O1 N2 C5 N3 179.46(13) . . . . ? C6 N2 C5 N3 2.91(16) . . . . ? O1 N2 C5 C1 0.0(2) . . . . ? C6 N2 C5 C1 -176.52(11) . . . . ? O2 N3 C5 N2 179.90(13) . . . . ? C7 N3 C5 N2 1.84(15) . . . . ? O2 N3 C5 C1 -0.7(2) . . . . ? C7 N3 C5 C1 -178.73(12) . . . . ? N1 C1 C5 N2 179.09(12) . . . . ? C2 C1 C5 N2 -2.1(2) . . . . ? N1 C1 C5 N3 -0.2(2) . . . . ? C2 C1 C5 N3 178.54(13) . . . . ? O1 N2 C6 C8 -62.5(2) . . . . ? C5 N2 C6 C8 114.19(17) . . . . ? O1 N2 C6 C9 55.3(2) . . . . ? C5 N2 C6 C9 -128.02(15) . . . . ? O1 N2 C6 C7 177.31(13) . . . . ? C5 N2 C6 C7 -5.98(15) . . . . ? O2 N3 C7 C10 -63.0(2) . . . . ? C5 N3 C7 C10 115.15(17) . . . . ? O2 N3 C7 C11 55.3(2) . . . . ? C5 N3 C7 C11 -126.6(2) . . . . ? O2 N3 C7 C6 176.51(12) . . . . ? C5 N3 C7 C6 -5.36(14) . . . . ? N2 C6 C7 N3 6.22(13) . . . . ? C8 C6 C7 N3 -108.28(15) . . . . ? C9 C6 C7 N3 122.94(16) . . . . ? N2 C6 C7 C10 -108.7(2) . . . . ? C8 C6 C7 C10 136.8(2) . . . . ? C9 C6 C7 C10 8.1(2) . . . . ? N2 C6 C7 C11 121.20(19) . . . . ? C8 C6 C7 C11 6.7(2) . . . . ? C9 C6 C7 C11 -122.1(2) . . . . ? #==END data_3 _database_code_CSD 199205 #------------------------------------------------------------------------------ _audit_creation_date 'Mon Nov 25 20:01:24 2002' _audit_creation_method SHELXL-97 _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ? _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_publication_material ? _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common 3-pyrrolylNN _chemical_formula_weight 222.27 _chemical_formula_analytical ? _chemical_formula_sum 'C11 H16 N3 O2' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 13.0654(13) _cell_length_b 14.4171(19) _cell_length_c 12.8740(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2425.0(5) _cell_formula_units_Z 8 _cell_measurement_temperature 298.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.0 _cell_measurement_theta_max 25.0 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_Int_Tables_number 61 _symmetry_space_group_name_Hall ? 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' #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max .56 _exptl_crystal_size_mid .48 _exptl_crystal_size_min .30 _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_meas 'not measured' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 298.2 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% ? _diffrn_reflns_number 2766 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.9477 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.50 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _reflns_number_total 2766 _reflns_number_gt 1992 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ 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' #------------------------------------------------------------------------------ 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 0.08022(9) 0.48833(7) 0.72925(8) 0.0500(3) Uani 1 1 d . . . O2 O 0.09807(10) 0.71946(7) 0.97703(8) 0.0575(3) Uani 1 1 d . . . N1 N 0.30136(10) 0.50092(9) 1.04247(11) 0.0476(3) Uani 1 1 d . . . N2 N 0.06283(9) 0.56427(8) 0.78005(8) 0.0359(3) Uani 1 1 d . . . N3 N 0.07134(9) 0.67361(8) 0.89632(9) 0.0384(3) Uani 1 1 d . . . C1 C 0.23646(11) 0.56859(10) 1.01256(11) 0.0408(3) Uani 1 1 d . . . C2 C 0.18447(10) 0.53827(10) 0.92517(10) 0.0371(3) Uani 1 1 d . . . C3 C 0.22130(13) 0.44724(11) 0.90381(13) 0.0497(4) Uani 1 1 d . . . C4 C 0.29220(13) 0.42723(12) 0.97697(13) 0.0537(4) Uani 1 1 d . . . C5 C 0.10917(10) 0.58967(9) 0.86882(9) 0.0336(3) Uani 1 1 d . . . C6 C -0.02633(10) 0.62518(10) 0.75452(11) 0.0396(3) Uani 1 1 d . . . C7 C 0.00508(11) 0.71472(10) 0.81324(10) 0.0417(3) Uani 1 1 d . . . C8 C -0.11997(14) 0.57684(15) 0.80093(16) 0.0578(5) Uani 1 1 d . . . C9 C -0.03843(16) 0.63597(15) 0.63814(13) 0.0551(4) Uani 1 1 d . . . C10 C -0.08229(17) 0.76854(15) 0.86285(17) 0.0639(5) Uani 1 1 d . . . C11 C 0.07355(18) 0.77945(13) 0.75002(17) 0.0601(5) Uani 1 1 d . . . H1 H 0.3430(16) 0.5041(13) 1.1003(18) 0.069(6) Uiso 1 1 d . . . H2 H 0.2299(13) 0.6267(12) 1.0514(13) 0.050(4) Uiso 1 1 d . . . H3 H 0.1992(13) 0.4086(13) 0.8477(14) 0.058(5) Uiso 1 1 d . . . H4 H 0.3303(16) 0.3731(14) 0.9896(15) 0.071(6) Uiso 1 1 d . . . H5 H -0.1261(18) 0.5137(16) 0.7670(18) 0.084(7) Uiso 1 1 d . . . H6 H -0.1808(18) 0.6141(16) 0.7871(17) 0.086(7) Uiso 1 1 d . . . H7 H -0.1139(15) 0.5688(14) 0.8756(16) 0.066(6) Uiso 1 1 d . . . H8 H -0.0508(16) 0.5752(17) 0.6080(17) 0.076(6) Uiso 1 1 d . . . H9 H 0.0244(16) 0.6599(13) 0.6062(15) 0.058(5) Uiso 1 1 d . . . H10 H -0.0975(15) 0.6786(14) 0.6262(15) 0.069(6) Uiso 1 1 d . . . H11 H -0.1281(17) 0.7872(14) 0.8069(18) 0.078(6) Uiso 1 1 d . . . H12 H -0.0512(18) 0.8250(19) 0.896(2) 0.093(7) Uiso 1 1 d . . . H13 H -0.1216(15) 0.7259(14) 0.9107(17) 0.070(6) Uiso 1 1 d . . . H14 H 0.1323(15) 0.7438(13) 0.7198(14) 0.062(5) Uiso 1 1 d . . . H15 H 0.1047(18) 0.8299(17) 0.7936(18) 0.093(7) Uiso 1 1 d . . . H16 H 0.0345(16) 0.8115(14) 0.6973(16) 0.071(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0708(8) 0.0382(6) 0.0410(6) -0.0133(4) -0.0004(5) 0.0012(5) O2 0.0867(8) 0.0416(6) 0.0442(6) -0.0158(5) -0.0162(5) 0.0093(6) N1 0.0430(7) 0.0556(8) 0.0443(7) 0.0112(6) -0.0032(6) 0.0023(6) N2 0.0435(6) 0.0328(6) 0.0315(5) -0.0037(4) 0.0013(5) -0.0023(5) N3 0.0505(7) 0.0322(6) 0.0325(6) -0.0042(5) -0.0023(5) 0.0041(5) C1 0.0415(7) 0.0427(8) 0.0382(7) 0.0045(6) 0.0005(6) -0.0020(6) C2 0.0403(7) 0.0352(7) 0.0359(6) 0.0022(5) 0.0046(5) 0.0004(6) C3 0.0596(10) 0.0422(8) 0.0473(8) -0.0030(7) -0.0012(7) 0.0110(7) C4 0.0581(9) 0.0484(9) 0.0546(10) 0.0073(7) 0.0024(8) 0.0154(8) C5 0.0396(7) 0.0306(6) 0.0306(6) -0.0014(5) 0.0026(5) -0.0015(5) C6 0.0401(7) 0.0437(7) 0.0351(7) 0.0028(6) -0.0004(6) -0.0003(6) C7 0.0528(8) 0.0370(7) 0.0354(7) 0.0030(6) -0.0017(6) 0.0058(6) C8 0.0455(9) 0.0675(12) 0.0605(11) 0.0064(9) 0.0031(8) -0.0106(8) C9 0.0628(11) 0.0659(12) 0.0368(8) 0.0016(8) -0.0075(8) 0.0006(9) C10 0.0735(13) 0.0598(12) 0.0585(11) -0.0020(9) -0.0023(10) 0.0293(10) C11 0.0799(13) 0.0447(9) 0.0556(10) 0.0108(8) -0.0073(10) -0.0106(9) #------------------------------------------------------------------------------ _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^)+(0.0779P)^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 SHELXL _refine_ls_extinction_coef 0.0068(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2766 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0674 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.215 _refine_diff_density_min -0.141 _refine_diff_density_rms 0.036 #------------------------------------------------------------------------------ _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 N2 1.2953(14) . ? O2 N3 1.2800(15) . ? N1 C1 1.3488(19) . ? N1 C4 1.362(2) . ? N1 H1 0.92(2) . ? N2 C5 1.3442(16) . ? N2 C6 1.4954(18) . ? N3 C5 1.3544(17) . ? N3 C7 1.4982(18) . ? C1 C2 1.385(2) . ? C1 H2 0.979(18) . ? C2 C3 1.425(2) . ? C2 C5 1.4294(19) . ? C3 C4 1.352(2) . ? C3 H3 0.957(19) . ? C4 H4 0.94(2) . ? C6 C9 1.515(2) . ? C6 C8 1.530(2) . ? C6 C7 1.551(2) . ? C7 C10 1.521(2) . ? C7 C11 1.528(2) . ? C8 H5 1.01(2) . ? C8 H6 0.97(2) . ? C8 H7 0.97(2) . ? C9 H8 0.97(2) . ? C9 H9 0.98(2) . ? C9 H10 1.00(2) . ? C10 H11 0.97(2) . ? C10 H12 1.00(3) . ? C10 H13 1.01(2) . ? C11 H14 1.00(2) . ? C11 H15 1.00(2) . ? C11 H16 0.97(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 C1 N1 C4 109.41(14) . . ? C1 N1 H1 124.4(12) . . ? C4 N1 H1 126.1(12) . . ? O1 N2 C5 125.48(12) . . ? O1 N2 C6 121.47(11) . . ? C5 N2 C6 112.20(11) . . ? O2 N3 C5 125.03(12) . . ? O2 N3 C7 122.20(11) . . ? C5 N3 C7 112.19(11) . . ? N1 C1 C2 108.17(13) . . ? N1 C1 H2 121.8(10) . . ? C2 C1 H2 130.0(10) . . ? C1 C2 C3 106.37(13) . . ? C1 C2 C5 125.89(13) . . ? C3 C2 C5 127.74(13) . . ? C4 C3 C2 107.07(15) . . ? C4 C3 H3 127.5(11) . . ? C2 C3 H3 125.4(11) . . ? C3 C4 N1 108.97(14) . . ? C3 C4 H4 131.4(12) . . ? N1 C4 H4 119.6(12) . . ? N2 C5 N3 107.53(11) . . ? N2 C5 C2 126.90(12) . . ? N3 C5 C2 125.57(12) . . ? N2 C6 C9 111.04(13) . . ? N2 C6 C8 105.65(13) . . ? C9 C6 C8 110.48(14) . . ? N2 C6 C7 100.10(10) . . ? C9 C6 C7 115.10(13) . . ? C8 C6 C7 113.60(13) . . ? N3 C7 C10 109.62(12) . . ? N3 C7 C11 106.48(13) . . ? C10 C7 C11 110.59(16) . . ? N3 C7 C6 99.88(10) . . ? C10 C7 C6 115.51(15) . . ? C11 C7 C6 113.80(13) . . ? C6 C8 H5 107.7(14) . . ? C6 C8 H6 109.2(13) . . ? H5 C8 H6 110.6(19) . . ? C6 C8 H7 112.1(12) . . ? H5 C8 H7 109.0(18) . . ? H6 C8 H7 108.2(18) . . ? C6 C9 H8 108.6(13) . . ? C6 C9 H9 111.3(11) . . ? H8 C9 H9 106.8(17) . . ? C6 C9 H10 107.3(11) . . ? H8 C9 H10 111.4(17) . . ? H9 C9 H10 111.5(16) . . ? C7 C10 H11 106.9(13) . . ? C7 C10 H12 106.7(14) . . ? H11 C10 H12 109.8(19) . . ? C7 C10 H13 109.1(11) . . ? H11 C10 H13 107.8(17) . . ? H12 C10 H13 116.1(19) . . ? C7 C11 H14 110.0(11) . . ? C7 C11 H15 112.5(13) . . ? H14 C11 H15 106.1(17) . . ? C7 C11 H16 110.9(12) . . ? H14 C11 H16 112.1(16) . . ? H15 C11 H16 105.0(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 -0.39(16) . . . . ? N1 C1 C2 C3 0.36(16) . . . . ? N1 C1 C2 C5 -179.51(13) . . . . ? C1 C2 C3 C4 -0.20(17) . . . . ? C5 C2 C3 C4 179.67(14) . . . . ? C2 C3 C4 N1 -0.03(19) . . . . ? C1 N1 C4 C3 0.26(18) . . . . ? O1 N2 C5 N3 179.09(12) . . . . ? C6 N2 C5 N3 -11.41(15) . . . . ? O1 N2 C5 C2 -1.1(2) . . . . ? C6 N2 C5 C2 168.38(12) . . . . ? O2 N3 C5 N2 -179.89(13) . . . . ? C7 N3 C5 N2 -8.46(15) . . . . ? O2 N3 C5 C2 0.3(2) . . . . ? C7 N3 C5 C2 171.75(12) . . . . ? C1 C2 C5 N2 175.17(13) . . . . ? C3 C2 C5 N2 -4.7(2) . . . . ? C1 C2 C5 N3 -5.1(2) . . . . ? C3 C2 C5 N3 175.07(14) . . . . ? O1 N2 C6 C9 -43.06(18) . . . . ? C5 N2 C6 C9 146.96(13) . . . . ? O1 N2 C6 C8 76.74(16) . . . . ? C5 N2 C6 C8 -93.24(14) . . . . ? O1 N2 C6 C7 -165.08(11) . . . . ? C5 N2 C6 C7 24.94(13) . . . . ? O2 N3 C7 C10 -43.5(2) . . . . ? C5 N3 C7 C10 144.81(15) . . . . ? O2 N3 C7 C11 76.18(17) . . . . ? C5 N3 C7 C11 -95.53(15) . . . . ? O2 N3 C7 C6 -165.22(13) . . . . ? C5 N3 C7 C6 23.07(14) . . . . ? N2 C6 C7 N3 -26.31(12) . . . . ? C9 C6 C7 N3 -145.40(13) . . . . ? C8 C6 C7 N3 85.83(15) . . . . ? N2 C6 C7 C10 -143.74(13) . . . . ? C9 C6 C7 C10 97.17(17) . . . . ? C8 C6 C7 C10 -31.61(19) . . . . ? N2 C6 C7 C11 86.74(14) . . . . ? C9 C6 C7 C11 -32.35(19) . . . . ? C8 C6 C7 C11 -161.12(15) . . . . ? #==END data_4 _database_code_CSD 199206 #------------------------------------------------------------------------------ _audit_creation_date 'Mon Nov 25 20:01:24 2002' _audit_creation_method SHELXL-97 _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction ? _computing_structure_solution SHELXS-97 _computing_structure_refinement SHELXL-97 _computing_publication_material ? _computing_molecular_graphics ? #------------------------------------------------------------------------------ _chemical_compound_source ? _chemical_name_common 4-(1'-pyrrolyl)phenylNN _chemical_formula_weight 298.36 _chemical_formula_analytical ? _chemical_formula_sum 'C17 H20 N3 O2' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_melting_point ? #------------------------------------------------------------------------------ _cell_length_a 12.284(4) _cell_length_b 12.657(5) _cell_length_c 10.953(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.72(2) _cell_angle_gamma 90.00 _cell_volume 1582.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 298.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.0 _cell_measurement_theta_max 25.0 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max .40 _exptl_crystal_size_mid .28 _exptl_crystal_size_min .10 _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_meas 'not measured' _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 298.2 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Rigaku sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method \w _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% ? _diffrn_reflns_number 3763 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 12.3028 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.987 _reflns_number_total 3579 _reflns_number_gt 1565 _reflns_threshold_expression >2sigma(I) #------------------------------------------------------------------------------ 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' #------------------------------------------------------------------------------ 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 0.70325(17) 0.25691(14) 1.2262(2) 0.0628(6) Uani 1 1 d . . . O2 O 0.59677(17) -0.09286(13) 1.12749(18) 0.0610(6) Uani 1 1 d . . . N1 N 0.90594(17) 0.07905(16) 0.79708(19) 0.0433(5) Uani 1 1 d . . . N2 N 0.66230(17) 0.16382(16) 1.2272(2) 0.0425(5) Uani 1 1 d . . . N3 N 0.61536(18) -0.00176(16) 1.18319(19) 0.0414(5) Uani 1 1 d . . . C1 C 0.9599(3) 0.1642(2) 0.7649(3) 0.0558(8) Uani 1 1 d . . . C2 C 1.0130(3) 0.1294(3) 0.6847(3) 0.0639(9) Uani 1 1 d . . . C3 C 0.9928(3) 0.0201(3) 0.6661(3) 0.0598(8) Uani 1 1 d . . . C4 C 0.9279(3) -0.0092(2) 0.7365(3) 0.0506(7) Uani 1 1 d . . . C5 C 0.8444(2) 0.08021(19) 0.8838(2) 0.0377(6) Uani 1 1 d . . . C6 C 0.7935(2) 0.1732(2) 0.9056(3) 0.0460(7) Uani 1 1 d . . . C7 C 0.7354(2) 0.1733(2) 0.9915(3) 0.0447(7) Uani 1 1 d . . . C8 C 0.7248(2) 0.08163(18) 1.0565(2) 0.0381(6) Uani 1 1 d . . . C9 C 0.7744(2) -0.0110(2) 1.0316(2) 0.0410(6) Uani 1 1 d . . . C10 C 0.8339(2) -0.0115(2) 0.9474(2) 0.0424(6) Uani 1 1 d . . . C11 C 0.6680(2) 0.08210(18) 1.1514(2) 0.0379(6) Uani 1 1 d . . . C12 C 0.5901(2) 0.1396(2) 1.3077(2) 0.0452(7) Uani 1 1 d . . . C13 C 0.5918(2) 0.01759(19) 1.3065(2) 0.0400(6) Uani 1 1 d . . . C14 C 0.4691(3) 0.1861(3) 1.2316(5) 0.0715(10) Uani 1 1 d . . . C15 C 0.6447(4) 0.1905(4) 1.4416(4) 0.0791(11) Uani 1 1 d . . . C16 C 0.6950(3) -0.0317(4) 1.4171(4) 0.0730(10) Uani 1 1 d . . . C17 C 0.4780(3) -0.0351(3) 1.2973(3) 0.0547(8) Uani 1 1 d . . . H1 H 0.955(2) 0.233(2) 0.797(2) 0.056(8) Uiso 1 1 d . . . H2 H 1.057(2) 0.170(2) 0.649(2) 0.055(8) Uiso 1 1 d . . . H3 H 1.010(2) -0.022(2) 0.612(2) 0.055(8) Uiso 1 1 d . . . H4 H 0.897(2) -0.076(2) 0.747(3) 0.068(9) Uiso 1 1 d . . . H5 H 0.800(2) 0.238(2) 0.857(3) 0.075(9) Uiso 1 1 d . . . H6 H 0.700(2) 0.2382(19) 1.010(2) 0.049(7) Uiso 1 1 d . . . H7 H 0.767(2) -0.075(2) 1.078(2) 0.060(8) Uiso 1 1 d . . . H8 H 0.870(2) -0.0771(19) 0.936(2) 0.053(7) Uiso 1 1 d . . . H9 H 0.413(3) 0.176(2) 1.276(3) 0.086(10) Uiso 1 1 d . . . H10 H 0.436(4) 0.148(3) 1.145(4) 0.135(16) Uiso 1 1 d . . . H11 H 0.476(3) 0.261(3) 1.219(3) 0.090(11) Uiso 1 1 d . . . H12 H 0.602(3) 0.168(2) 1.499(3) 0.098(12) Uiso 1 1 d . . . H13 H 0.644(3) 0.265(2) 1.430(3) 0.068(10) Uiso 1 1 d . . . H14 H 0.738(3) 0.163(2) 1.493(3) 0.100(12) Uiso 1 1 d . . . H15 H 0.682(3) -0.026(2) 1.498(3) 0.085(11) Uiso 1 1 d . . . H16 H 0.702(3) -0.111(3) 1.392(3) 0.109(13) Uiso 1 1 d . . . H17 H 0.769(4) 0.001(3) 1.424(3) 0.115(14) Uiso 1 1 d . . . H18 H 0.461(3) -0.014(2) 1.379(3) 0.082(10) Uiso 1 1 d . . . H19 H 0.486(3) -0.111(3) 1.298(3) 0.091(11) Uiso 1 1 d . . . H20 H 0.412(3) -0.009(2) 1.212(3) 0.099(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0819(14) 0.0389(11) 0.0859(15) -0.0188(10) 0.0525(13) -0.0195(10) O2 0.0900(14) 0.0322(10) 0.0785(13) -0.0141(10) 0.0520(12) -0.0128(10) N1 0.0488(13) 0.0398(12) 0.0457(13) 0.0005(11) 0.0226(11) -0.0033(11) N2 0.0457(13) 0.0354(12) 0.0513(13) -0.0067(10) 0.0239(11) -0.0072(10) N3 0.0486(13) 0.0329(11) 0.0469(12) -0.0029(10) 0.0226(11) -0.0010(10) C1 0.066(2) 0.0445(18) 0.069(2) 0.0071(15) 0.0398(18) -0.0048(15) C2 0.073(2) 0.071(2) 0.063(2) 0.0129(18) 0.0420(18) 0.0016(17) C3 0.070(2) 0.068(2) 0.0487(18) -0.0066(17) 0.0306(17) 0.0032(17) C4 0.063(2) 0.0493(18) 0.0459(16) -0.0038(14) 0.0279(15) -0.0029(15) C5 0.0389(14) 0.0396(14) 0.0367(13) -0.0036(12) 0.0163(12) -0.0041(12) C6 0.0604(18) 0.0309(14) 0.0533(17) 0.0031(13) 0.0289(15) -0.0020(13) C7 0.0564(17) 0.0329(15) 0.0531(16) 0.0015(12) 0.0298(14) 0.0017(13) C8 0.0430(14) 0.0329(13) 0.0404(14) -0.0045(13) 0.0179(12) -0.0015(12) C9 0.0470(16) 0.0352(15) 0.0462(15) 0.0086(13) 0.0235(13) 0.0027(12) C10 0.0477(16) 0.0338(15) 0.0489(15) 0.0039(13) 0.0217(14) 0.0076(12) C11 0.0399(14) 0.0290(13) 0.0456(15) -0.0006(12) 0.0167(12) 0.0002(11) C12 0.0479(16) 0.0442(16) 0.0521(16) -0.0123(13) 0.0285(14) -0.0083(12) C13 0.0402(14) 0.0411(15) 0.0421(14) -0.0003(12) 0.0193(12) -0.0008(12) C14 0.057(2) 0.049(2) 0.120(3) 0.003(2) 0.045(2) 0.0090(17) C15 0.111(3) 0.075(3) 0.065(2) -0.026(2) 0.048(2) -0.032(3) C16 0.069(2) 0.089(3) 0.059(2) 0.019(2) 0.0212(19) 0.021(2) C17 0.060(2) 0.0495(19) 0.065(2) -0.0042(17) 0.0356(18) -0.0117(16) #------------------------------------------------------------------------------ _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^)+(0.0487P)^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 SHELXL _refine_ls_extinction_coef 0.0016(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3579 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1775 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1276 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 0.855 _refine_ls_restrained_S_all 0.855 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.156 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.037 #------------------------------------------------------------------------------ _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 N2 1.283(2) . ? O2 N3 1.285(2) . ? N1 C4 1.375(3) . ? N1 C1 1.378(3) . ? N1 C5 1.416(3) . ? N2 C11 1.344(3) . ? N2 C12 1.496(3) . ? N3 C11 1.354(3) . ? N3 C13 1.502(3) . ? C1 C2 1.347(4) . ? C1 H1 0.95(3) . ? C2 C3 1.406(4) . ? C2 H2 0.93(2) . ? C3 C4 1.350(4) . ? C3 H3 0.88(2) . ? C4 H4 0.95(3) . ? C5 C10 1.384(3) . ? C5 C6 1.394(3) . ? C6 C7 1.375(3) . ? C6 H5 0.99(3) . ? C7 C8 1.392(3) . ? C7 H6 0.98(2) . ? C8 C9 1.394(3) . ? C8 C11 1.450(3) . ? C9 C10 1.372(3) . ? C9 H7 0.97(2) . ? C10 H8 0.97(2) . ? C12 C15 1.513(4) . ? C12 C14 1.528(4) . ? C12 C13 1.544(3) . ? C13 C17 1.519(4) . ? C13 C16 1.526(4) . ? C14 H9 0.98(3) . ? C14 H10 1.01(4) . ? C14 H11 0.97(3) . ? C15 H12 0.99(3) . ? C15 H13 0.95(3) . ? C15 H14 1.13(3) . ? C16 H15 0.96(3) . ? C16 H16 1.05(3) . ? C16 H17 0.98(4) . ? C17 H18 1.02(3) . ? C17 H19 0.96(3) . ? C17 H20 1.04(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 C4 N1 C1 108.2(2) . . ? C4 N1 C5 125.5(2) . . ? C1 N1 C5 126.2(2) . . ? O1 N2 C11 126.2(2) . . ? O1 N2 C12 120.90(19) . . ? C11 N2 C12 112.58(19) . . ? O2 N3 C11 126.8(2) . . ? O2 N3 C13 120.92(19) . . ? C11 N3 C13 111.88(19) . . ? C2 C1 N1 107.8(3) . . ? C2 C1 H1 130.9(16) . . ? N1 C1 H1 121.3(15) . . ? C1 C2 C3 108.3(3) . . ? C1 C2 H2 126.2(16) . . ? C3 C2 H2 125.6(15) . . ? C4 C3 C2 107.3(3) . . ? C4 C3 H3 123.9(17) . . ? C2 C3 H3 128.4(17) . . ? C3 C4 N1 108.4(3) . . ? C3 C4 H4 131.5(16) . . ? N1 C4 H4 120.2(16) . . ? C10 C5 C6 119.4(2) . . ? C10 C5 N1 120.1(2) . . ? C6 C5 N1 120.5(2) . . ? C7 C6 C5 119.8(3) . . ? C7 C6 H5 122.4(16) . . ? C5 C6 H5 117.8(16) . . ? C6 C7 C8 121.3(3) . . ? C6 C7 H6 121.4(14) . . ? C8 C7 H6 117.3(14) . . ? C7 C8 C9 118.1(2) . . ? C7 C8 C11 121.6(2) . . ? C9 C8 C11 120.3(2) . . ? C10 C9 C8 121.0(2) . . ? C10 C9 H7 121.2(14) . . ? C8 C9 H7 117.7(14) . . ? C9 C10 C5 120.4(2) . . ? C9 C10 H8 117.9(14) . . ? C5 C10 H8 121.6(14) . . ? N2 C11 N3 107.8(2) . . ? N2 C11 C8 126.5(2) . . ? N3 C11 C8 125.7(2) . . ? N2 C12 C15 109.7(2) . . ? N2 C12 C14 105.6(2) . . ? C15 C12 C14 110.9(3) . . ? N2 C12 C13 100.81(18) . . ? C15 C12 C13 115.6(3) . . ? C14 C12 C13 113.2(2) . . ? N3 C13 C17 110.4(2) . . ? N3 C13 C16 105.5(2) . . ? C17 C13 C16 110.3(3) . . ? N3 C13 C12 100.28(18) . . ? C17 C13 C12 115.2(2) . . ? C16 C13 C12 114.3(3) . . ? C12 C14 H9 113.4(18) . . ? C12 C14 H10 107(2) . . ? H9 C14 H10 107(3) . . ? C12 C14 H11 110(2) . . ? H9 C14 H11 108(3) . . ? H10 C14 H11 111(3) . . ? C12 C15 H12 110.1(19) . . ? C12 C15 H13 108.4(18) . . ? H12 C15 H13 113(3) . . ? C12 C15 H14 110.9(17) . . ? H12 C15 H14 106(2) . . ? H13 C15 H14 109(3) . . ? C13 C16 H15 108.9(19) . . ? C13 C16 H16 107.8(19) . . ? H15 C16 H16 112(3) . . ? C13 C16 H17 112(2) . . ? H15 C16 H17 112(3) . . ? H16 C16 H17 105(3) . . ? C13 C17 H18 107.6(16) . . ? C13 C17 H19 110.0(18) . . ? H18 C17 H19 108(2) . . ? C13 C17 H20 108.5(18) . . ? H18 C17 H20 111(2) . . ? H19 C17 H20 112(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 0.8(3) . . . . ? C5 N1 C1 C2 177.2(2) . . . . ? N1 C1 C2 C3 -0.3(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? C2 C3 C4 N1 0.7(3) . . . . ? C1 N1 C4 C3 -0.9(3) . . . . ? C5 N1 C4 C3 -177.4(2) . . . . ? C4 N1 C5 C10 21.0(4) . . . . ? C1 N1 C5 C10 -154.8(3) . . . . ? C4 N1 C5 C6 -158.7(2) . . . . ? C1 N1 C5 C6 25.5(4) . . . . ? C10 C5 C6 C7 1.1(4) . . . . ? N1 C5 C6 C7 -179.2(2) . . . . ? C5 C6 C7 C8 -0.8(4) . . . . ? C6 C7 C8 C9 -0.4(4) . . . . ? C6 C7 C8 C11 177.3(2) . . . . ? C7 C8 C9 C10 1.2(4) . . . . ? C11 C8 C9 C10 -176.5(2) . . . . ? C8 C9 C10 C5 -0.9(4) . . . . ? C6 C5 C10 C9 -0.3(4) . . . . ? N1 C5 C10 C9 -180.0(2) . . . . ? O1 N2 C11 N3 179.6(2) . . . . ? C12 N2 C11 N3 -6.4(3) . . . . ? O1 N2 C11 C8 2.1(4) . . . . ? C12 N2 C11 C8 176.1(2) . . . . ? O2 N3 C11 N2 175.6(2) . . . . ? C13 N3 C11 N2 -11.5(3) . . . . ? O2 N3 C11 C8 -6.9(4) . . . . ? C13 N3 C11 C8 166.0(2) . . . . ? C7 C8 C11 N2 -28.7(4) . . . . ? C9 C8 C11 N2 148.9(2) . . . . ? C7 C8 C11 N3 154.2(2) . . . . ? C9 C8 C11 N3 -28.1(4) . . . . ? O1 N2 C12 C15 -43.0(4) . . . . ? C11 N2 C12 C15 142.7(3) . . . . ? O1 N2 C12 C14 76.6(3) . . . . ? C11 N2 C12 C14 -97.7(3) . . . . ? O1 N2 C12 C13 -165.4(2) . . . . ? C11 N2 C12 C13 20.3(3) . . . . ? O2 N3 C13 C17 -41.6(3) . . . . ? C11 N3 C13 C17 145.1(2) . . . . ? O2 N3 C13 C16 77.6(3) . . . . ? C11 N3 C13 C16 -95.7(3) . . . . ? O2 N3 C13 C12 -163.4(2) . . . . ? C11 N3 C13 C12 23.2(2) . . . . ? N2 C12 C13 N3 -23.9(2) . . . . ? C15 C12 C13 N3 -142.1(3) . . . . ? C14 C12 C13 N3 88.4(3) . . . . ? N2 C12 C13 C17 -142.3(2) . . . . ? C15 C12 C13 C17 99.5(3) . . . . ? C14 C12 C13 C17 -30.0(3) . . . . ? N2 C12 C13 C16 88.4(3) . . . . ? C15 C12 C13 C16 -29.8(3) . . . . ? C14 C12 C13 C16 -159.3(3) . . . . ? #==END