# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jiannian Yao' _publ_contact_author_address ; Beijing National Laboratory for Molecular Sciences (BNLMS) Insitution of Chemistry Chinese Academy of Sciences Beijing 100080 CHINA ; _publ_contact_author_email JNYAO@ICCAS.AC.CN _publ_section_title ; Distinct Nanostructures from Isomeric Molecules of Bis (iminopyrroles) benzenes: Effects of Molecular Structures on Nanostructural Morphologies ; loop_ _publ_author_name 'Jiannian Yao.' 'Hongbing Fu.' 'Jin Shi Ma.' 'Ying Ma.' 'Aidong Peng.' ; Yaobing Wang ; 'Yongsheng Zhao.' # Attachment '1.cif' data_50315a _database_code_depnum_ccdc_archive 'CCDC 299563' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N4' _chemical_formula_weight 262.31 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 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 10.894(2) _cell_length_b 9.1577(18) _cell_length_c 14.177(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.888(3) _cell_angle_gamma 90.00 _cell_volume 1414.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1273 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 20.98 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 9359 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.25 _reflns_number_total 3441 _reflns_number_gt 1668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0813P)^2^+0.0438P] 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 3441 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1153 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1404 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.002 _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 N1 N 1.03635(15) 0.25811(16) 0.47965(10) 0.0560(4) Uani 1 1 d . . . N2 N 0.61311(15) 0.18870(17) 0.69895(11) 0.0582(5) Uani 1 1 d . . . N3 N 1.26607(16) 0.29191(18) 0.37897(12) 0.0606(5) Uani 1 1 d . . . H3A H 1.202(2) 0.282(3) 0.3317(17) 0.098(8) Uiso 1 1 d . . . N4 N 0.39234(16) 0.1457(2) 0.80862(12) 0.0618(5) Uani 1 1 d . . . H4 H 0.448(2) 0.194(2) 0.8458(15) 0.077(7) Uiso 1 1 d . . . C1 C 0.93038(17) 0.2435(2) 0.53581(12) 0.0519(5) Uani 1 1 d . . . C2 C 0.86049(17) 0.1172(2) 0.52628(14) 0.0610(5) Uani 1 1 d . . . H2 H 0.8843 0.0454 0.4839 0.073 Uiso 1 1 calc R . . C3 C 0.75662(17) 0.0971(2) 0.57865(13) 0.0617(5) Uani 1 1 d . . . H3 H 0.7125 0.0106 0.5725 0.074 Uiso 1 1 calc R . . C4 C 0.71660(17) 0.2038(2) 0.64063(12) 0.0525(5) Uani 1 1 d . . . C5 C 0.78536(19) 0.3313(2) 0.64796(14) 0.0622(6) Uani 1 1 d . . . H5 H 0.7597 0.4050 0.6882 0.075 Uiso 1 1 calc R . . C6 C 0.89067(18) 0.3509(2) 0.59688(13) 0.0611(5) Uani 1 1 d . . . H6 H 0.9354 0.4369 0.6035 0.073 Uiso 1 1 calc R . . C7 C 1.13766(19) 0.2888(2) 0.52113(13) 0.0580(5) Uani 1 1 d . . . H7 H 1.1372 0.3014 0.5862 0.070 Uiso 1 1 calc R . . C8 C 1.25157(18) 0.3052(2) 0.47438(14) 0.0570(5) Uani 1 1 d . . . C9 C 1.3664(2) 0.3286(3) 0.51274(16) 0.0753(7) Uani 1 1 d . . . H9 H 1.3847 0.3417 0.5765 0.090 Uiso 1 1 calc R . . C10 C 1.4503(2) 0.3293(3) 0.44022(19) 0.0878(8) Uani 1 1 d . . . H10 H 1.5347 0.3426 0.4464 0.105 Uiso 1 1 calc R . . C11 C 1.3864(2) 0.3072(3) 0.35860(17) 0.0766(7) Uani 1 1 d . . . H11 H 1.4197 0.3031 0.2986 0.092 Uiso 1 1 calc R . . C12 C 0.52212(19) 0.1128(2) 0.66933(14) 0.0664(6) Uani 1 1 d . . . H12 H 0.5276 0.0699 0.6101 0.080 Uiso 1 1 calc R . . C13 C 0.41295(18) 0.0893(2) 0.72090(13) 0.0626(5) Uani 1 1 d . . . C14 C 0.3076(2) 0.0178(3) 0.69430(16) 0.0886(8) Uani 1 1 d . . . H14 H 0.2948 -0.0315 0.6376 0.106 Uiso 1 1 calc R . . C15 C 0.2233(2) 0.0311(3) 0.76602(17) 0.0898(8) Uani 1 1 d . . . H15 H 0.1439 -0.0061 0.7661 0.108 Uiso 1 1 calc R . . C16 C 0.27835(19) 0.1084(3) 0.83575(16) 0.0767(7) Uani 1 1 d . . . H16 H 0.2434 0.1322 0.8932 0.092 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 0.0503(10) 0.0594(10) 0.0587(9) 0.0018(7) 0.0094(8) -0.0048(8) N2 0.0551(11) 0.0627(10) 0.0572(9) 0.0052(7) 0.0119(8) -0.0045(8) N3 0.0501(11) 0.0681(11) 0.0640(11) -0.0029(8) 0.0114(9) -0.0040(8) N4 0.0483(11) 0.0748(12) 0.0625(11) 0.0017(9) 0.0071(9) -0.0052(9) C1 0.0477(11) 0.0559(11) 0.0523(10) 0.0073(8) 0.0081(9) 0.0010(9) C2 0.0527(12) 0.0606(12) 0.0701(12) -0.0100(10) 0.0115(10) -0.0006(10) C3 0.0545(13) 0.0567(12) 0.0741(13) -0.0038(10) 0.0071(10) -0.0064(9) C4 0.0521(12) 0.0562(11) 0.0494(10) 0.0056(8) 0.0065(9) -0.0016(9) C5 0.0702(14) 0.0548(12) 0.0622(11) -0.0045(9) 0.0201(11) -0.0028(10) C6 0.0676(14) 0.0518(11) 0.0644(12) 0.0012(9) 0.0169(11) -0.0095(10) C7 0.0578(14) 0.0577(12) 0.0586(11) 0.0037(9) 0.0075(10) 0.0020(10) C8 0.0498(12) 0.0596(12) 0.0617(12) 0.0010(9) 0.0052(10) 0.0003(9) C9 0.0537(14) 0.0968(18) 0.0754(14) -0.0094(12) -0.0007(12) 0.0041(12) C10 0.0451(13) 0.120(2) 0.0984(18) -0.0201(15) 0.0077(13) -0.0059(13) C11 0.0551(15) 0.0934(17) 0.0819(15) -0.0112(12) 0.0207(12) -0.0087(12) C12 0.0627(14) 0.0847(15) 0.0519(11) 0.0007(10) 0.0055(10) -0.0042(12) C13 0.0535(13) 0.0815(14) 0.0529(11) 0.0030(10) 0.0061(10) -0.0088(11) C14 0.0723(16) 0.127(2) 0.0664(14) -0.0090(13) 0.0018(12) -0.0304(15) C15 0.0592(15) 0.131(2) 0.0795(16) 0.0030(14) 0.0067(13) -0.0288(15) C16 0.0490(14) 0.1057(18) 0.0760(14) 0.0041(13) 0.0160(12) -0.0103(12) _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 C7 1.274(2) . ? N1 C1 1.419(2) . ? N2 C12 1.276(2) . ? N2 C4 1.415(2) . ? N3 C11 1.354(3) . ? N3 C8 1.370(2) . ? N3 H3A 0.96(2) . ? N4 C16 1.350(2) . ? N4 C13 1.368(2) . ? N4 H4 0.91(2) . ? C1 C6 1.384(3) . ? C1 C2 1.390(3) . ? C2 C3 1.375(2) . ? C2 H2 0.9300 . ? C3 C4 1.389(3) . ? C3 H3 0.9300 . ? C4 C5 1.390(3) . ? C5 C6 1.378(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.424(3) . ? C7 H7 0.9300 . ? C8 C9 1.373(3) . ? C9 C10 1.387(3) . ? C9 H9 0.9300 . ? C10 C11 1.356(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.422(3) . ? C12 H12 0.9300 . ? C13 C14 1.369(3) . ? C14 C15 1.386(3) . ? C14 H14 0.9300 . ? C15 C16 1.349(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 N1 C1 117.93(16) . . ? C12 N2 C4 118.86(17) . . ? C11 N3 C8 109.17(19) . . ? C11 N3 H3A 123.6(14) . . ? C8 N3 H3A 127.0(14) . . ? C16 N4 C13 109.17(19) . . ? C16 N4 H4 124.4(14) . . ? C13 N4 H4 126.2(14) . . ? C6 C1 C2 118.42(17) . . ? C6 C1 N1 123.29(17) . . ? C2 C1 N1 118.25(16) . . ? C3 C2 C1 120.89(18) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 121.04(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 117.67(18) . . ? C3 C4 N2 124.15(17) . . ? C5 C4 N2 118.14(17) . . ? C6 C5 C4 121.47(17) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 120.48(18) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? N1 C7 C8 124.30(18) . . ? N1 C7 H7 117.9 . . ? C8 C7 H7 117.9 . . ? N3 C8 C9 106.68(18) . . ? N3 C8 C7 124.40(19) . . ? C9 C8 C7 128.84(19) . . ? C8 C9 C10 108.3(2) . . ? C8 C9 H9 125.8 . . ? C10 C9 H9 125.8 . . ? C11 C10 C9 107.2(2) . . ? C11 C10 H10 126.4 . . ? C9 C10 H10 126.4 . . ? N3 C11 C10 108.6(2) . . ? N3 C11 H11 125.7 . . ? C10 C11 H11 125.7 . . ? N2 C12 C13 124.36(19) . . ? N2 C12 H12 117.8 . . ? C13 C12 H12 117.8 . . ? N4 C13 C14 106.39(18) . . ? N4 C13 C12 124.11(19) . . ? C14 C13 C12 129.4(2) . . ? C13 C14 C15 108.5(2) . . ? C13 C14 H14 125.7 . . ? C15 C14 H14 125.7 . . ? C16 C15 C14 106.9(2) . . ? C16 C15 H15 126.5 . . ? C14 C15 H15 126.5 . . ? C15 C16 N4 108.9(2) . . ? C15 C16 H16 125.5 . . ? N4 C16 H16 125.5 . . ? 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 C7 N1 C1 C6 54.8(2) . . . . ? C7 N1 C1 C2 -127.7(2) . . . . ? C6 C1 C2 C3 -2.2(3) . . . . ? N1 C1 C2 C3 -179.84(17) . . . . ? C1 C2 C3 C4 1.8(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C2 C3 C4 N2 -177.83(17) . . . . ? C12 N2 C4 C3 -32.3(3) . . . . ? C12 N2 C4 C5 150.06(19) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? N2 C4 C5 C6 176.80(17) . . . . ? C4 C5 C6 C1 0.6(3) . . . . ? C2 C1 C6 C5 1.1(3) . . . . ? N1 C1 C6 C5 178.53(17) . . . . ? C1 N1 C7 C8 179.23(16) . . . . ? C11 N3 C8 C9 -0.2(2) . . . . ? C11 N3 C8 C7 -177.19(19) . . . . ? N1 C7 C8 N3 0.9(3) . . . . ? N1 C7 C8 C9 -175.3(2) . . . . ? N3 C8 C9 C10 0.0(2) . . . . ? C7 C8 C9 C10 176.8(2) . . . . ? C8 C9 C10 C11 0.3(3) . . . . ? C8 N3 C11 C10 0.4(3) . . . . ? C9 C10 C11 N3 -0.4(3) . . . . ? C4 N2 C12 C13 -179.92(18) . . . . ? C16 N4 C13 C14 0.8(3) . . . . ? C16 N4 C13 C12 177.3(2) . . . . ? N2 C12 C13 N4 0.1(3) . . . . ? N2 C12 C13 C14 175.8(2) . . . . ? N4 C13 C14 C15 0.1(3) . . . . ? C12 C13 C14 C15 -176.2(2) . . . . ? C13 C14 C15 C16 -0.8(3) . . . . ? C14 C15 C16 N4 1.3(3) . . . . ? C13 N4 C16 C15 -1.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A N2 0.96(2) 2.12(3) 3.032(3) 157(2) 4_665 N4 H4 N1 0.91(2) 2.16(2) 3.000(3) 152.9(18) 4_566 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.141 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.035 # Attachment '2.cif' data_50306b _database_code_depnum_ccdc_archive 'CCDC 299564' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N4' _chemical_formula_weight 262.31 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 10.2048(10) _cell_length_b 15.5662(15) _cell_length_c 17.4159(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2766.5(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3400 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 22.81 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% . _diffrn_reflns_number 17434 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3301 _reflns_number_gt 2348 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0399P)^2^+0.3729P] 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 3301 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0914 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _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 N1 N 0.80880(10) 1.07959(6) 0.57723(6) 0.0430(2) Uani 1 1 d . . . N2 N 0.81995(11) 0.79266(6) 0.68383(6) 0.0452(3) Uani 1 1 d . . . N3 N 0.61959(10) 1.20798(6) 0.53129(6) 0.0446(3) Uani 1 1 d . . . H3 H 0.6614(15) 1.2261(9) 0.5778(9) 0.068(5) Uiso 1 1 d . . . N4 N 0.67984(13) 0.64402(7) 0.74315(7) 0.0565(3) Uani 1 1 d . . . H4A H 0.6843(15) 0.6400(10) 0.6920(9) 0.065(5) Uiso 1 1 d . . . C1 C 0.88256(12) 1.00873(7) 0.60477(7) 0.0404(3) Uani 1 1 d . . . C2 C 0.82102(12) 0.93278(7) 0.62545(7) 0.0414(3) Uani 1 1 d . . . H2 H 0.7327 0.9251 0.6142 0.050 Uiso 1 1 calc R . . C3 C 0.88972(12) 0.86814(7) 0.66270(7) 0.0417(3) Uani 1 1 d . . . C4 C 1.02195(13) 0.87872(8) 0.67686(8) 0.0529(3) Uani 1 1 d . . . H4 H 1.0690 0.8358 0.7017 0.064 Uiso 1 1 calc R . . C5 C 1.08401(13) 0.95329(9) 0.65399(9) 0.0588(4) Uani 1 1 d . . . H5 H 1.1735 0.9594 0.6623 0.071 Uiso 1 1 calc R . . C6 C 1.01549(13) 1.01862(9) 0.61908(8) 0.0516(3) Uani 1 1 d . . . H6 H 1.0580 1.0691 0.6052 0.062 Uiso 1 1 calc R . . C7 C 0.72816(12) 1.06690(8) 0.52253(7) 0.0430(3) Uani 1 1 d . . . H7 H 0.7287 1.0136 0.4984 0.052 Uiso 1 1 calc R . . C8 C 0.63684(12) 1.13004(7) 0.49616(7) 0.0422(3) Uani 1 1 d . . . C9 C 0.54814(13) 1.12595(9) 0.43668(7) 0.0508(3) Uani 1 1 d . . . H9 H 0.5378 1.0803 0.4027 0.061 Uiso 1 1 calc R . . C10 C 0.47651(14) 1.20222(9) 0.43626(8) 0.0540(3) Uani 1 1 d . . . H10 H 0.4103 1.2170 0.4020 0.065 Uiso 1 1 calc R . . C11 C 0.52200(13) 1.25111(9) 0.49556(8) 0.0502(3) Uani 1 1 d . . . H11 H 0.4910 1.3052 0.5092 0.060 Uiso 1 1 calc R . . C12 C 0.82022(12) 0.77178(7) 0.75453(7) 0.0454(3) Uani 1 1 d . . . H12 H 0.8707 0.8046 0.7879 0.054 Uiso 1 1 calc R . . C13 C 0.74856(13) 0.70158(8) 0.78594(7) 0.0454(3) Uani 1 1 d . . . C14 C 0.72028(14) 0.68475(9) 0.86172(8) 0.0534(3) Uani 1 1 d . . . H14 H 0.7538 0.7141 0.9039 0.064 Uiso 1 1 calc R . . C15 C 0.63303(15) 0.61640(9) 0.86422(8) 0.0578(4) Uani 1 1 d . . . H15 H 0.5968 0.5919 0.9081 0.069 Uiso 1 1 calc R . . C16 C 0.61051(17) 0.59200(9) 0.79053(9) 0.0659(4) Uani 1 1 d . . . H16 H 0.5565 0.5471 0.7751 0.079 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 0.0448(6) 0.0362(5) 0.0481(6) 0.0026(4) -0.0019(5) -0.0011(4) N2 0.0531(6) 0.0336(5) 0.0490(6) 0.0003(4) -0.0075(5) 0.0030(4) N3 0.0484(6) 0.0415(6) 0.0438(6) 0.0021(4) -0.0021(5) 0.0027(5) N4 0.0808(8) 0.0452(6) 0.0434(6) 0.0007(5) 0.0017(6) -0.0085(6) C1 0.0421(6) 0.0354(6) 0.0438(6) -0.0028(5) -0.0013(5) 0.0023(5) C2 0.0381(6) 0.0375(6) 0.0487(7) -0.0024(5) -0.0071(5) 0.0003(5) C3 0.0452(7) 0.0351(6) 0.0446(7) -0.0048(5) -0.0031(5) 0.0032(5) C4 0.0444(7) 0.0488(7) 0.0655(9) 0.0013(6) -0.0066(6) 0.0120(6) C5 0.0346(7) 0.0651(9) 0.0768(10) 0.0028(7) -0.0032(6) 0.0021(6) C6 0.0428(7) 0.0480(7) 0.0641(8) 0.0029(6) 0.0009(6) -0.0056(6) C7 0.0470(7) 0.0380(6) 0.0439(6) -0.0001(5) 0.0014(6) -0.0012(5) C8 0.0449(7) 0.0394(6) 0.0423(6) 0.0025(5) 0.0008(5) -0.0012(5) C9 0.0537(8) 0.0510(7) 0.0477(7) -0.0014(6) -0.0052(6) -0.0022(6) C10 0.0481(7) 0.0612(8) 0.0527(8) 0.0093(6) -0.0080(6) 0.0033(6) C11 0.0506(7) 0.0460(7) 0.0541(7) 0.0083(6) 0.0017(6) 0.0085(6) C12 0.0462(7) 0.0411(6) 0.0488(7) -0.0048(5) -0.0063(6) 0.0065(5) C13 0.0508(7) 0.0400(6) 0.0454(7) -0.0012(5) -0.0033(6) 0.0100(5) C14 0.0600(8) 0.0568(8) 0.0436(7) -0.0009(6) -0.0041(6) 0.0095(7) C15 0.0677(9) 0.0558(8) 0.0498(8) 0.0081(6) 0.0080(7) 0.0096(7) C16 0.0874(11) 0.0517(8) 0.0586(9) 0.0048(7) 0.0041(8) -0.0136(8) _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 C7 1.2743(15) . ? N1 C1 1.4188(14) . ? N2 C12 1.2736(16) . ? N2 C3 1.4222(15) . ? N3 C11 1.3527(16) . ? N3 C8 1.3701(15) . ? N3 H3 0.958(16) . ? N4 C16 1.3554(18) . ? N4 C13 1.3601(17) . ? N4 H4A 0.894(15) . ? C1 C2 1.3863(16) . ? C1 C6 1.3878(18) . ? C2 C3 1.3874(16) . ? C2 H2 0.9300 . ? C3 C4 1.3816(18) . ? C4 C5 1.3810(19) . ? C4 H4 0.9300 . ? C5 C6 1.3758(19) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.4301(16) . ? C7 H7 0.9300 . ? C8 C9 1.3772(17) . ? C9 C10 1.3943(19) . ? C9 H9 0.9300 . ? C10 C11 1.3642(19) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.4242(18) . ? C12 H12 0.9300 . ? C13 C14 1.3760(18) . ? C14 C15 1.388(2) . ? C14 H14 0.9300 . ? C15 C16 1.358(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? 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 N1 C1 118.35(10) . . ? C12 N2 C3 117.38(11) . . ? C11 N3 C8 109.19(11) . . ? C11 N3 H3 124.8(9) . . ? C8 N3 H3 125.5(9) . . ? C16 N4 C13 109.22(12) . . ? C16 N4 H4A 126.2(10) . . ? C13 N4 H4A 124.5(10) . . ? C2 C1 C6 119.39(11) . . ? C2 C1 N1 120.70(11) . . ? C6 C1 N1 119.54(10) . . ? C1 C2 C3 120.74(11) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 119.37(11) . . ? C4 C3 N2 122.77(11) . . ? C2 C3 N2 117.85(11) . . ? C5 C4 C3 119.78(12) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 121.05(12) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C1 119.61(12) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? N1 C7 C8 123.67(11) . . ? N1 C7 H7 118.2 . . ? C8 C7 H7 118.2 . . ? N3 C8 C9 107.00(11) . . ? N3 C8 C7 123.29(11) . . ? C9 C8 C7 129.65(11) . . ? C8 C9 C10 108.00(12) . . ? C8 C9 H9 126.0 . . ? C10 C9 H9 126.0 . . ? C11 C10 C9 107.02(12) . . ? C11 C10 H10 126.5 . . ? C9 C10 H10 126.5 . . ? N3 C11 C10 108.77(12) . . ? N3 C11 H11 125.6 . . ? C10 C11 H11 125.6 . . ? N2 C12 C13 124.47(12) . . ? N2 C12 H12 117.8 . . ? C13 C12 H12 117.8 . . ? N4 C13 C14 106.98(12) . . ? N4 C13 C12 124.04(12) . . ? C14 C13 C12 128.47(12) . . ? C13 C14 C15 108.09(12) . . ? C13 C14 H14 126.0 . . ? C15 C14 H14 126.0 . . ? C16 C15 C14 107.05(13) . . ? C16 C15 H15 126.5 . . ? C14 C15 H15 126.5 . . ? N4 C16 C15 108.66(14) . . ? N4 C16 H16 125.7 . . ? C15 C16 H16 125.7 . . ? 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 C7 N1 C1 C2 -51.32(16) . . . . ? C7 N1 C1 C6 135.76(13) . . . . ? C6 C1 C2 C3 2.39(18) . . . . ? N1 C1 C2 C3 -170.54(11) . . . . ? C1 C2 C3 C4 -2.22(18) . . . . ? C1 C2 C3 N2 178.61(11) . . . . ? C12 N2 C3 C4 58.22(17) . . . . ? C12 N2 C3 C2 -122.64(13) . . . . ? C2 C3 C4 C5 0.1(2) . . . . ? N2 C3 C4 C5 179.24(12) . . . . ? C3 C4 C5 C6 1.8(2) . . . . ? C4 C5 C6 C1 -1.7(2) . . . . ? C2 C1 C6 C5 -0.4(2) . . . . ? N1 C1 C6 C5 172.56(12) . . . . ? C1 N1 C7 C8 171.94(11) . . . . ? C11 N3 C8 C9 0.70(14) . . . . ? C11 N3 C8 C7 -176.69(11) . . . . ? N1 C7 C8 N3 -5.61(19) . . . . ? N1 C7 C8 C9 177.63(13) . . . . ? N3 C8 C9 C10 -0.19(14) . . . . ? C7 C8 C9 C10 176.97(12) . . . . ? C8 C9 C10 C11 -0.37(15) . . . . ? C8 N3 C11 C10 -0.95(15) . . . . ? C9 C10 C11 N3 0.81(15) . . . . ? C3 N2 C12 C13 175.76(11) . . . . ? C16 N4 C13 C14 -0.26(16) . . . . ? C16 N4 C13 C12 -172.65(13) . . . . ? N2 C12 C13 N4 5.7(2) . . . . ? N2 C12 C13 C14 -164.94(13) . . . . ? N4 C13 C14 C15 -0.24(15) . . . . ? C12 C13 C14 C15 171.70(12) . . . . ? C13 C14 C15 C16 0.65(16) . . . . ? C13 N4 C16 C15 0.68(17) . . . . ? C14 C15 C16 N4 -0.81(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4A N1 0.894(15) 2.210(15) 3.0610(16) 158.8(13) 8_755 N3 H3 N2 0.958(16) 2.126(15) 3.0292(15) 156.6(13) 8_765 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.125 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.029 # Attachment '3.CIF' data_q _database_code_depnum_ccdc_archive 'CCDC 299565' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 N4' _chemical_formula_weight 262.31 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 34.919(7) _cell_length_b 17.106(3) _cell_length_c 14.362(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.49(3) _cell_angle_gamma 90.00 _cell_volume 8563(3) _cell_formula_units_Z 24 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 34515 _cell_measurement_theta_min 1.17 _cell_measurement_theta_max 25.50 _exptl_crystal_description 'Thin platelet' _exptl_crystal_colour brown _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.221 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3312 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9945 _exptl_absorpt_process_details Abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'rigaku Raxis Rapid IP Area Detector' _diffrn_measurement_method '\w Oscillation' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34515 _diffrn_reflns_av_R_equivalents 0.1631 _diffrn_reflns_av_sigmaI/netI 0.2672 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7707 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _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^)+(0.0373P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00040(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7707 _refine_ls_number_parameters 542 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2855 _refine_ls_R_factor_gt 0.1205 _refine_ls_wR_factor_ref 0.2118 _refine_ls_wR_factor_gt 0.1771 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.28319(16) 0.0526(4) 0.1266(4) 0.0645(17) Uani 1 1 d . . . H1A H 0.3078 0.0530 0.1350 0.077 Uiso 1 1 calc R . . N2 N 0.30837(16) 0.2096(3) 0.1566(4) 0.0540(15) Uani 1 1 d . . . N3 N 0.36200(15) 0.2343(3) 0.3012(4) 0.0508(14) Uani 1 1 d . . . N4 N 0.39025(16) 0.1057(3) 0.4059(4) 0.0556(15) Uani 1 1 d . . . H4A H 0.3658 0.1025 0.3956 0.067 Uiso 1 1 calc R . . N5 N 0.21302(16) 0.7017(4) 0.1253(4) 0.0617(17) Uani 1 1 d . . . H5A H 0.1884 0.7004 0.1267 0.074 Uiso 1 1 calc R . . N6 N 0.18708(16) 0.5438(3) 0.1469(4) 0.0537(15) Uani 1 1 d . . . N7 N 0.14224(15) 0.5153(3) 0.2892(4) 0.0512(15) Uani 1 1 d . . . N8 N 0.11671(15) 0.6459(3) 0.3924(4) 0.0589(16) Uani 1 1 d . . . H8A H 0.1409 0.6493 0.3844 0.071 Uiso 1 1 calc R . . N9 N 0.04549(15) 0.0804(3) 0.1065(4) 0.0567(16) Uani 1 1 d . . . H9A H 0.0218 0.0789 0.1193 0.068 Uiso 1 1 calc R . . N10 N 0.02224(15) 0.2279(3) 0.1751(3) 0.0486(15) Uani 1 1 d . . . N11 N 0.05722(15) 0.1774(3) 0.3843(3) 0.0542(15) Uani 1 1 d . . . H11A H 0.0328 0.1808 0.3722 0.065 Uiso 1 1 calc R . . N12 N 0.02724(15) 0.0296(3) 0.3221(4) 0.0510(15) Uani 1 1 d . . . C1 C 0.2613(2) -0.0104(5) 0.1099(5) 0.074(2) Uani 1 1 d . . . H1B H 0.2707 -0.0612 0.1068 0.089 Uiso 1 1 calc R . . C2 C 0.2230(2) 0.0093(6) 0.0976(6) 0.094(3) Uani 1 1 d . . . H2B H 0.2022 -0.0233 0.0830 0.113 Uiso 1 1 calc R . . C3 C 0.2230(2) 0.0904(5) 0.1126(5) 0.079(2) Uani 1 1 d . . . H3B H 0.2012 0.1216 0.1121 0.095 Uiso 1 1 calc R . . C4 C 0.2596(2) 0.1164(5) 0.1280(4) 0.058(2) Uani 1 1 d . . . C5 C 0.2734(2) 0.1944(5) 0.1467(5) 0.060(2) Uani 1 1 d . . . H5B H 0.2557 0.2347 0.1515 0.072 Uiso 1 1 calc R . . C6 C 0.31941(18) 0.2870(4) 0.1778(5) 0.0537(19) Uani 1 1 d . . . C7 C 0.3057(2) 0.3521(5) 0.1287(5) 0.072(2) Uani 1 1 d . . . H7B H 0.2877 0.3446 0.0790 0.086 Uiso 1 1 calc R . . C8 C 0.3174(2) 0.4276(5) 0.1504(6) 0.081(3) Uani 1 1 d . . . H8B H 0.3065 0.4694 0.1169 0.097 Uiso 1 1 calc R . . C9 C 0.3446(3) 0.4409(5) 0.2205(7) 0.090(3) Uani 1 1 d . . . H9B H 0.3529 0.4915 0.2342 0.109 Uiso 1 1 calc R . . C10 C 0.36033(19) 0.3764(4) 0.2724(5) 0.064(2) Uani 1 1 d . . . H10B H 0.3782 0.3852 0.3219 0.077 Uiso 1 1 calc R . . C11 C 0.34913(19) 0.3002(4) 0.2499(5) 0.0542(19) Uani 1 1 d . . . C12 C 0.39771(18) 0.2265(4) 0.3204(4) 0.0561(19) Uani 1 1 d . . . H12B H 0.4144 0.2634 0.2981 0.067 Uiso 1 1 calc R . . C13 C 0.41298(18) 0.1633(4) 0.3745(5) 0.0494(17) Uani 1 1 d . . . C14 C 0.4499(2) 0.1463(5) 0.4052(5) 0.067(2) Uani 1 1 d . . . H14A H 0.4715 0.1749 0.3915 0.081 Uiso 1 1 calc R . . C15 C 0.4498(2) 0.0798(5) 0.4599(5) 0.079(3) Uani 1 1 d . . . H15A H 0.4709 0.0574 0.4925 0.094 Uiso 1 1 calc R . . C16 C 0.4130(2) 0.0535(4) 0.4568(5) 0.065(2) Uani 1 1 d . . . H16A H 0.4046 0.0080 0.4845 0.078 Uiso 1 1 calc R . . C17 C 0.2343(2) 0.7654(5) 0.1219(5) 0.078(2) Uani 1 1 d . . . H17A H 0.2246 0.8161 0.1205 0.093 Uiso 1 1 calc R . . C18 C 0.2721(2) 0.7470(5) 0.1207(5) 0.080(3) Uani 1 1 d . . . H18A H 0.2926 0.7812 0.1179 0.096 Uiso 1 1 calc R . . C19 C 0.2734(2) 0.6665(5) 0.1246(5) 0.075(2) Uani 1 1 d . . . H19A H 0.2955 0.6362 0.1258 0.090 Uiso 1 1 calc R . . C20 C 0.2367(2) 0.6385(4) 0.1264(5) 0.0552(19) Uani 1 1 d . . . C21 C 0.2226(2) 0.5603(4) 0.1398(5) 0.063(2) Uani 1 1 d . . . H21A H 0.2402 0.5196 0.1436 0.075 Uiso 1 1 calc R . . C22 C 0.17747(18) 0.4653(4) 0.1624(5) 0.0544(19) Uani 1 1 d . . . C23 C 0.1892(2) 0.4026(4) 0.1123(5) 0.064(2) Uani 1 1 d . . . H23A H 0.2055 0.4118 0.0646 0.076 Uiso 1 1 calc R . . C24 C 0.1782(2) 0.3263(4) 0.1283(5) 0.068(2) Uani 1 1 d . . . H24A H 0.1867 0.2855 0.0920 0.081 Uiso 1 1 calc R . . C25 C 0.1548(2) 0.3128(4) 0.1988(6) 0.072(2) Uani 1 1 d . . . H25A H 0.1477 0.2618 0.2120 0.086 Uiso 1 1 calc R . . C26 C 0.1416(2) 0.3727(4) 0.2504(5) 0.065(2) Uani 1 1 d . . . H26A H 0.1252 0.3618 0.2973 0.078 Uiso 1 1 calc R . . C27 C 0.15224(18) 0.4505(4) 0.2346(5) 0.0516(18) Uani 1 1 d . . . C28 C 0.10678(19) 0.5238(4) 0.3064(4) 0.0507(18) Uani 1 1 d . . . H28A H 0.0890 0.4871 0.2830 0.061 Uiso 1 1 calc R . . C29 C 0.09375(17) 0.5870(4) 0.3599(4) 0.0465(17) Uani 1 1 d . . . C30 C 0.05788(18) 0.6029(4) 0.3913(5) 0.057(2) Uani 1 1 d . . . H30A H 0.0361 0.5723 0.3800 0.068 Uiso 1 1 calc R . . C31 C 0.0598(2) 0.6709(5) 0.4415(5) 0.080(3) Uani 1 1 d . . . H31A H 0.0399 0.6943 0.4718 0.096 Uiso 1 1 calc R . . C32 C 0.0966(2) 0.6979(5) 0.4386(5) 0.069(2) Uani 1 1 d . . . H32A H 0.1060 0.7445 0.4643 0.083 Uiso 1 1 calc R . . C33 C 0.0649(2) 0.0205(4) 0.0702(5) 0.070(2) Uani 1 1 d . . . H33A H 0.0549 -0.0285 0.0549 0.084 Uiso 1 1 calc R . . C34 C 0.1013(2) 0.0443(5) 0.0598(5) 0.077(2) Uani 1 1 d . . . H34A H 0.1207 0.0144 0.0364 0.092 Uiso 1 1 calc R . . C35 C 0.1045(2) 0.1213(5) 0.0901(5) 0.072(2) Uani 1 1 d . . . H35A H 0.1264 0.1522 0.0903 0.086 Uiso 1 1 calc R . . C36 C 0.06907(19) 0.1438(4) 0.1201(5) 0.0506(18) Uani 1 1 d . . . C37 C 0.05660(19) 0.2150(3) 0.1576(4) 0.0495(18) Uani 1 1 d . . . H37A H 0.0746 0.2543 0.1700 0.059 Uiso 1 1 calc R . . C38 C 0.01264(16) 0.3017(4) 0.2137(4) 0.0454(17) Uani 1 1 d . . . C39 C 0.02447(18) 0.3747(4) 0.1800(4) 0.0505(17) Uani 1 1 d . . . H39A H 0.0410 0.3757 0.1316 0.061 Uiso 1 1 calc R . . C40 C 0.01287(17) 0.4424(4) 0.2147(5) 0.054(2) Uani 1 1 d . . . H40A H 0.0219 0.4894 0.1920 0.065 Uiso 1 1 calc R . . C41 C 0.0803(2) 0.2352(5) 0.4172(5) 0.066(2) Uani 1 1 d . . . H41A H 0.0725 0.2859 0.4299 0.079 Uiso 1 1 calc R . . C42 C 0.1168(2) 0.2077(5) 0.4289(5) 0.078(2) Uani 1 1 d . . . H42A H 0.1381 0.2359 0.4516 0.093 Uiso 1 1 calc R . . C43 C 0.1164(2) 0.1310(4) 0.4014(5) 0.069(2) Uani 1 1 d . . . H43A H 0.1376 0.0980 0.4019 0.082 Uiso 1 1 calc R . . C44 C 0.0795(2) 0.1113(4) 0.3732(5) 0.0509(17) Uani 1 1 d . . . C45 C 0.0632(2) 0.0404(4) 0.3383(5) 0.059(2) Uani 1 1 d . . . H45A H 0.0797 -0.0007 0.3265 0.071 Uiso 1 1 calc R . . C46 C 0.01535(18) -0.0445(3) 0.2850(4) 0.0485(18) Uani 1 1 d . . . C47 C 0.02819(18) -0.1151(4) 0.3213(5) 0.0571(19) Uani 1 1 d . . . H47A H 0.0463 -0.1153 0.3717 0.069 Uiso 1 1 calc R . . C48 C 0.01508(19) -0.1850(4) 0.2853(5) 0.063(2) Uani 1 1 d . . . H48A H 0.0258 -0.2318 0.3070 0.076 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 0.049(4) 0.057(4) 0.085(5) 0.016(4) -0.013(3) 0.002(4) N2 0.057(4) 0.056(4) 0.051(4) 0.006(3) 0.015(3) 0.003(3) N3 0.051(4) 0.052(4) 0.048(4) 0.010(3) -0.006(3) 0.002(3) N4 0.055(3) 0.054(4) 0.057(4) -0.001(3) -0.002(3) 0.010(3) N5 0.062(4) 0.059(4) 0.066(4) 0.001(3) 0.022(3) -0.019(4) N6 0.050(3) 0.051(4) 0.062(4) 0.003(3) 0.015(3) 0.004(3) N7 0.049(4) 0.053(4) 0.053(4) 0.008(3) 0.018(3) -0.002(3) N8 0.046(3) 0.070(4) 0.061(4) -0.005(3) 0.010(3) 0.007(3) N9 0.047(3) 0.053(4) 0.071(4) 0.003(3) 0.013(3) -0.005(3) N10 0.053(4) 0.051(4) 0.044(3) 0.008(3) 0.015(3) 0.004(3) N11 0.052(4) 0.058(4) 0.053(4) -0.012(3) 0.001(3) -0.007(3) N12 0.051(4) 0.044(3) 0.058(4) 0.003(3) 0.005(3) 0.009(3) C1 0.086(6) 0.068(6) 0.069(6) -0.004(4) 0.004(5) -0.006(5) C2 0.070(6) 0.108(8) 0.100(7) -0.009(6) -0.024(5) -0.018(6) C3 0.054(5) 0.087(7) 0.093(7) -0.012(5) -0.020(4) -0.003(5) C4 0.055(4) 0.090(6) 0.028(4) -0.005(4) -0.006(3) -0.002(5) C5 0.044(4) 0.074(5) 0.064(5) 0.012(4) 0.015(4) 0.018(4) C6 0.040(4) 0.067(5) 0.055(5) 0.029(4) 0.013(3) 0.015(4) C7 0.056(5) 0.090(7) 0.068(6) 0.011(5) -0.003(4) 0.015(5) C8 0.073(6) 0.078(7) 0.093(7) 0.031(6) 0.016(5) 0.006(5) C9 0.083(7) 0.052(5) 0.139(9) 0.007(6) 0.027(6) 0.004(5) C10 0.054(4) 0.059(5) 0.080(6) 0.013(5) 0.004(4) -0.009(4) C11 0.047(4) 0.067(5) 0.051(5) 0.010(4) 0.021(4) 0.005(4) C12 0.043(4) 0.076(5) 0.048(4) 0.002(4) -0.005(3) -0.016(4) C13 0.039(4) 0.054(4) 0.054(5) -0.001(4) -0.008(3) 0.008(4) C14 0.055(5) 0.082(6) 0.065(5) 0.000(5) -0.007(4) 0.009(4) C15 0.064(6) 0.108(7) 0.063(6) -0.006(5) -0.004(4) 0.032(5) C16 0.093(6) 0.056(5) 0.044(5) 0.015(4) -0.002(4) 0.025(5) C17 0.080(6) 0.069(6) 0.084(6) 0.005(5) 0.010(5) -0.002(5) C18 0.077(6) 0.079(7) 0.084(6) -0.008(5) 0.012(5) -0.007(5) C19 0.064(6) 0.090(6) 0.074(6) 0.002(5) 0.030(4) 0.005(5) C20 0.055(5) 0.058(5) 0.053(5) -0.008(4) 0.010(4) -0.001(4) C21 0.062(5) 0.057(5) 0.071(6) -0.001(4) 0.016(4) 0.007(4) C22 0.046(4) 0.052(5) 0.066(5) -0.010(4) 0.004(4) 0.011(4) C23 0.076(5) 0.063(5) 0.052(5) -0.010(4) 0.007(4) 0.014(4) C24 0.067(5) 0.054(5) 0.081(6) -0.028(5) -0.007(4) 0.006(4) C25 0.057(5) 0.041(5) 0.117(7) 0.000(5) 0.006(5) -0.001(4) C26 0.063(5) 0.053(5) 0.078(6) 0.016(4) -0.008(4) -0.013(4) C27 0.047(4) 0.051(4) 0.056(5) 0.001(4) -0.004(4) 0.004(4) C28 0.067(5) 0.043(4) 0.041(4) 0.016(3) 0.000(4) -0.022(4) C29 0.037(4) 0.065(5) 0.038(4) 0.009(4) 0.001(3) -0.001(4) C30 0.032(4) 0.065(5) 0.075(6) 0.009(4) 0.011(4) 0.001(4) C31 0.069(6) 0.100(7) 0.070(6) -0.001(5) 0.007(5) 0.037(5) C32 0.079(6) 0.070(5) 0.058(5) -0.014(4) 0.004(4) 0.018(5) C33 0.086(6) 0.057(5) 0.070(6) -0.017(4) 0.025(5) 0.013(5) C34 0.084(6) 0.073(6) 0.076(6) -0.022(5) 0.026(5) 0.023(5) C35 0.064(5) 0.061(5) 0.091(6) 0.008(5) 0.021(4) 0.014(5) C36 0.046(4) 0.043(4) 0.064(5) 0.001(4) 0.012(3) 0.009(4) C37 0.058(4) 0.030(4) 0.060(5) 0.000(3) 0.007(4) -0.017(4) C38 0.037(4) 0.041(4) 0.058(5) -0.006(3) -0.002(3) -0.002(3) C39 0.049(4) 0.049(4) 0.054(4) 0.003(4) 0.007(3) -0.008(4) C40 0.054(5) 0.031(4) 0.077(6) 0.010(4) 0.007(4) -0.006(3) C41 0.081(6) 0.062(5) 0.056(5) -0.006(4) 0.012(4) 0.008(5) C42 0.081(6) 0.071(6) 0.080(6) -0.009(5) 0.000(5) -0.030(5) C43 0.059(5) 0.051(5) 0.095(6) -0.007(5) -0.001(4) -0.012(4) C44 0.061(5) 0.044(4) 0.048(5) -0.001(4) 0.006(4) -0.001(4) C45 0.063(5) 0.055(5) 0.059(5) -0.003(4) 0.009(4) 0.018(4) C46 0.056(4) 0.028(4) 0.061(5) -0.007(3) 0.002(3) 0.004(3) C47 0.053(4) 0.051(5) 0.068(5) 0.014(4) 0.004(4) 0.009(4) C48 0.059(5) 0.043(4) 0.087(7) 0.013(4) 0.012(4) -0.004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.334(9) . ? N1 C4 1.368(9) . ? N2 C5 1.249(8) . ? N2 C6 1.407(8) . ? N3 C12 1.267(7) . ? N3 C11 1.405(8) . ? N4 C13 1.359(8) . ? N4 C16 1.376(8) . ? N5 C17 1.321(9) . ? N5 C20 1.359(8) . ? N6 C21 1.281(7) . ? N6 C22 1.405(8) . ? N7 C28 1.285(7) . ? N7 C27 1.414(8) . ? N8 C32 1.334(7) . ? N8 C29 1.352(8) . ? N9 C33 1.350(8) . ? N9 C36 1.369(7) . ? N10 C37 1.260(7) . ? N10 C38 1.428(7) . ? N11 C41 1.343(8) . ? N11 C44 1.388(7) . ? N12 C45 1.278(7) . ? N12 C46 1.426(7) . ? C1 C2 1.380(10) . ? C2 C3 1.403(11) . ? C3 C4 1.358(9) . ? C4 C5 1.439(10) . ? C6 C7 1.387(9) . ? C6 C11 1.438(9) . ? C7 C8 1.384(11) . ? C8 C9 1.362(11) . ? C9 C10 1.423(10) . ? C10 C11 1.393(9) . ? C12 C13 1.416(9) . ? C13 C14 1.367(9) . ? C14 C15 1.383(10) . ? C15 C16 1.361(9) . ? C17 C18 1.358(9) . ? C18 C19 1.378(10) . ? C19 C20 1.371(9) . ? C20 C21 1.442(9) . ? C22 C23 1.368(8) . ? C22 C27 1.424(8) . ? C23 C24 1.383(9) . ? C24 C25 1.360(9) . ? C25 C26 1.360(9) . ? C26 C27 1.404(9) . ? C28 C29 1.418(8) . ? C29 C30 1.383(8) . ? C30 C31 1.369(10) . ? C31 C32 1.370(10) . ? C33 C34 1.351(9) . ? C34 C35 1.391(9) . ? C35 C36 1.388(8) . ? C36 C37 1.411(8) . ? C38 C38 1.405(11) 2 ? C38 C39 1.412(8) . ? C39 C40 1.332(8) . ? C40 C40 1.395(11) 2 ? C41 C42 1.359(9) . ? C42 C43 1.369(9) . ? C43 C44 1.368(9) . ? C44 C45 1.419(9) . ? C46 C47 1.380(8) . ? C46 C46 1.424(13) 2 ? C47 C48 1.370(9) . ? C48 C48 1.418(14) 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 107.9(6) . . ? C5 N2 C6 118.3(6) . . ? C12 N3 C11 118.6(6) . . ? C13 N4 C16 108.5(6) . . ? C17 N5 C20 108.3(6) . . ? C21 N6 C22 117.7(6) . . ? C28 N7 C27 117.9(6) . . ? C32 N8 C29 110.5(6) . . ? C33 N9 C36 110.2(5) . . ? C37 N10 C38 118.7(6) . . ? C41 N11 C44 108.2(6) . . ? C45 N12 C46 117.2(6) . . ? N1 C1 C2 111.4(8) . . ? C1 C2 C3 103.4(8) . . ? C4 C3 C2 109.8(8) . . ? N1 C4 C3 107.4(7) . . ? N1 C4 C5 123.2(6) . . ? C3 C4 C5 129.4(8) . . ? N2 C5 C4 121.9(7) . . ? C7 C6 N2 124.3(7) . . ? C7 C6 C11 116.9(8) . . ? N2 C6 C11 118.6(6) . . ? C6 C7 C8 123.1(8) . . ? C9 C8 C7 120.3(9) . . ? C8 C9 C10 119.2(9) . . ? C11 C10 C9 120.6(8) . . ? N3 C11 C10 123.5(7) . . ? N3 C11 C6 116.5(6) . . ? C10 C11 C6 119.6(7) . . ? N3 C12 C13 122.2(6) . . ? N4 C13 C14 107.3(7) . . ? N4 C13 C12 121.8(6) . . ? C14 C13 C12 130.9(7) . . ? C13 C14 C15 109.0(7) . . ? C16 C15 C14 106.6(7) . . ? C15 C16 N4 108.5(7) . . ? N5 C17 C18 110.9(8) . . ? C17 C18 C19 105.2(8) . . ? C20 C19 C18 108.7(7) . . ? N5 C20 C19 106.8(7) . . ? N5 C20 C21 121.8(6) . . ? C19 C20 C21 130.8(8) . . ? N6 C21 C20 123.7(7) . . ? C23 C22 N6 125.7(6) . . ? C23 C22 C27 117.5(7) . . ? N6 C22 C27 116.7(6) . . ? C22 C23 C24 123.9(7) . . ? C25 C24 C23 117.9(7) . . ? C24 C25 C26 121.2(7) . . ? C25 C26 C27 121.6(7) . . ? C26 C27 N7 125.2(6) . . ? C26 C27 C22 117.9(7) . . ? N7 C27 C22 116.7(6) . . ? N7 C28 C29 122.3(6) . . ? N8 C29 C30 105.8(6) . . ? N8 C29 C28 123.5(5) . . ? C30 C29 C28 130.7(7) . . ? C29 C30 C31 108.8(7) . . ? C32 C31 C30 106.6(7) . . ? N8 C32 C31 108.3(7) . . ? N9 C33 C34 108.2(7) . . ? C33 C34 C35 108.0(7) . . ? C36 C35 C34 107.7(7) . . ? N9 C36 C35 106.0(6) . . ? N9 C36 C37 122.8(6) . . ? C35 C36 C37 131.2(7) . . ? N10 C37 C36 123.1(6) . . ? C38 C38 C39 117.7(4) 2 . ? C38 C38 N10 117.5(3) 2 . ? C39 C38 N10 124.7(5) . . ? C40 C39 C38 122.6(6) . . ? C39 C40 C40 119.7(4) . 2 ? N11 C41 C42 109.0(7) . . ? C41 C42 C43 107.7(7) . . ? C42 C43 C44 108.3(7) . . ? N11 C44 C43 106.8(6) . . ? N11 C44 C45 121.5(6) . . ? C43 C44 C45 131.7(7) . . ? N12 C45 C44 123.8(6) . . ? C47 C46 C46 118.7(4) . 2 ? C47 C46 N12 123.7(6) . . ? C46 C46 N12 117.0(3) 2 . ? C48 C47 C46 121.9(7) . . ? C47 C48 C48 119.1(4) . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N7 0.86 2.10 2.875(8) 149.4 4_545 N4 H4A N6 0.86 2.16 2.956(8) 154.5 4_545 N5 H5A N3 0.86 2.18 2.937(8) 147.4 4 N8 H8A N2 0.86 2.16 2.958(7) 153.5 4 N9 H9A N12 0.86 2.13 2.928(7) 154.9 2 N11 H11A N10 0.86 2.16 2.980(7) 160.3 2 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.242 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.060