# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Pedro Gomes' 'M Teresa Duarte' 'Clara Gomes' 'Teresa Nunes' 'Conceizao Oliveira' 'Luis Veiros' _publ_contact_author_name 'Pedro Gomes' _publ_contact_author_email PEDRO.T.GOMES@IST.UTL.PT _publ_section_title ; Sodium complexes containing 2-iminopyrrolyl ligands: the influence of steric hindrance in the formation of coordination polymers ; # Attachment 'NaIminopyrrolyl_PTGomes.cif' data_Ligand_precursor_I _database_code_depnum_ccdc_archive 'CCDC 727070' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H10 N2' _chemical_formula_sum 'C11 H10 N2' _chemical_formula_weight 170.21 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 'P b c a' _symmetry_int_tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4490(14) _cell_length_b 18.186(3) _cell_length_c 21.204(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3643.7(10) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4443 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.12 _exptl_crystal_description prism _exptl_crystal_colour bronze _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9814 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 82598 _diffrn_reflns_av_R_equivalents 0.0713 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 28.12 _reflns_number_total 4443 _reflns_number_gt 3143 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material enCIFer _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^)+(0.0521P)^2^+0.5052P] 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 4443 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0944 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.06338(11) -0.22582(5) -0.01492(5) 0.0270(2) Uani 1 1 d . . . N2 N 0.23277(11) -0.12247(5) -0.08863(4) 0.0266(2) Uani 1 1 d . . . N3 N 0.19211(12) -0.00648(6) 0.01052(5) 0.0304(2) Uani 1 1 d . . . C9 C 0.50641(15) 0.00340(7) -0.14934(6) 0.0355(3) Uani 1 1 d . . . C13 C 0.13614(13) 0.00250(7) 0.06967(6) 0.0293(3) Uani 1 1 d . . . C5 C -0.02318(14) -0.28164(7) 0.00228(6) 0.0308(3) Uani 1 1 d . . . C6 C 0.17076(13) -0.17824(7) -0.11318(5) 0.0272(3) Uani 1 1 d . . . C12 C 0.24306(14) -0.04802(7) -0.18566(5) 0.0291(3) Uani 1 1 d . . . C8 C 0.43612(14) -0.04666(7) -0.11175(6) 0.0308(3) Uani 1 1 d . . . C11 C 0.31432(15) 0.00239(8) -0.22281(6) 0.0355(3) Uani 1 1 d . . . N4 N 0.09522(11) -0.12422(6) 0.09506(5) 0.0305(2) Uani 1 1 d . . . C7 C 0.30423(13) -0.07335(6) -0.12977(5) 0.0253(3) Uani 1 1 d . . . C2 C 0.08927(13) -0.23045(6) -0.07850(5) 0.0266(3) Uani 1 1 d . . . C15 C 0.20645(15) 0.11253(8) 0.03291(7) 0.0396(3) Uani 1 1 d . . . C21 C -0.08249(16) -0.16317(9) 0.17354(6) 0.0415(4) Uani 1 1 d . . . C10 C 0.44578(15) 0.02849(8) -0.20487(6) 0.0368(3) Uani 1 1 d . . . C17 C 0.08704(13) -0.05577(7) 0.10888(6) 0.0304(3) Uani 1 1 d . . . C16 C 0.23411(15) 0.06008(7) -0.01190(7) 0.0366(3) Uani 1 1 d . . . C4 C -0.05260(15) -0.32362(7) -0.04972(6) 0.0355(3) Uani 1 1 d . . . C3 C 0.01810(15) -0.29150(7) -0.10063(6) 0.0354(3) Uani 1 1 d . . . C14 C 0.14512(15) 0.07669(7) 0.08417(7) 0.0375(3) Uani 1 1 d . . . C18 C 0.04249(14) -0.17510(7) 0.14004(5) 0.0326(3) Uani 1 1 d . . . C19 C 0.11751(17) -0.24014(8) 0.14902(6) 0.0399(3) Uani 1 1 d . . . C20 C 0.0704(2) -0.29164(9) 0.19267(7) 0.0509(4) Uani 1 1 d . . . C23 C -0.1269(2) -0.21465(10) 0.21751(7) 0.0541(5) Uani 1 1 d . . . C22 C -0.0510(2) -0.27827(10) 0.22729(7) 0.0578(5) Uani 1 1 d . . . H3 H 0.0191(16) -0.3086(8) -0.1437(6) 0.040(4) Uiso 1 1 d . . . H17 H 0.0497(15) -0.0389(8) 0.1507(7) 0.038(4) Uiso 1 1 d . . . H6 H 0.1776(14) -0.1894(7) -0.1594(6) 0.032(3) Uiso 1 1 d . . . H12 H 0.1489(15) -0.0655(7) -0.1990(6) 0.030(3) Uiso 1 1 d . . . H9 H 0.5960(16) 0.0230(8) -0.1365(6) 0.039(4) Uiso 1 1 d . . . H16 H 0.2752(17) 0.0656(8) -0.0539(7) 0.045(4) Uiso 1 1 d . . . H8 H 0.4787(15) -0.0654(7) -0.0732(6) 0.037(4) Uiso 1 1 d . . . H11 H 0.2689(17) 0.0205(8) -0.2615(7) 0.048(4) Uiso 1 1 d . . . H19 H 0.2041(18) -0.2480(9) 0.1233(7) 0.052(4) Uiso 1 1 d . . . H1 H 0.0929(15) -0.1895(8) 0.0110(7) 0.040(4) Uiso 1 1 d . . . H5 H -0.0542(15) -0.2867(7) 0.0438(6) 0.033(4) Uiso 1 1 d . . . H4 H -0.1117(17) -0.3673(9) -0.0508(7) 0.051(4) Uiso 1 1 d . . . H2 H 0.1976(17) -0.0476(9) -0.0113(7) 0.050(5) Uiso 1 1 d . . . H10 H 0.4956(16) 0.0652(8) -0.2296(6) 0.041(4) Uiso 1 1 d . . . H23 H -0.1402(17) -0.1182(9) 0.1643(7) 0.047(4) Uiso 1 1 d . . . H15 H 0.2288(17) 0.1648(9) 0.0290(7) 0.054(5) Uiso 1 1 d . . . H14 H 0.1125(17) 0.0978(8) 0.1241(8) 0.049(4) Uiso 1 1 d . . . H20 H 0.1248(19) -0.3381(9) 0.1959(8) 0.061(5) Uiso 1 1 d . . . H22 H -0.218(2) -0.2042(9) 0.2410(8) 0.066(5) Uiso 1 1 d . . . H21 H -0.0855(19) -0.3128(9) 0.2575(8) 0.062(5) 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 N1 0.0290(5) 0.0246(5) 0.0274(5) 0.0002(4) 0.0005(4) -0.0017(4) N2 0.0270(5) 0.0271(5) 0.0256(4) 0.0035(4) 0.0006(4) 0.0007(4) N3 0.0329(6) 0.0265(5) 0.0319(5) -0.0003(4) -0.0013(4) 0.0012(5) C9 0.0276(7) 0.0393(7) 0.0395(7) -0.0009(6) 0.0033(6) -0.0038(6) C13 0.0230(6) 0.0325(7) 0.0323(6) -0.0049(5) -0.0032(5) 0.0017(5) C5 0.0298(7) 0.0294(6) 0.0331(6) 0.0061(5) 0.0011(5) -0.0026(5) C6 0.0275(6) 0.0284(6) 0.0258(5) 0.0010(5) 0.0016(5) 0.0037(5) C12 0.0261(7) 0.0344(7) 0.0266(5) 0.0015(5) 0.0005(5) 0.0016(5) C8 0.0292(7) 0.0350(7) 0.0283(6) 0.0025(5) -0.0010(5) 0.0008(5) C11 0.0354(7) 0.0424(8) 0.0286(6) 0.0095(5) 0.0027(5) 0.0030(6) N4 0.0314(6) 0.0348(6) 0.0254(5) -0.0014(4) 0.0004(4) -0.0010(5) C7 0.0268(6) 0.0254(6) 0.0238(5) -0.0008(4) 0.0042(4) 0.0030(5) C2 0.0276(6) 0.0247(6) 0.0276(5) 0.0005(4) 0.0004(5) 0.0024(5) C15 0.0322(8) 0.0263(7) 0.0603(9) -0.0003(6) -0.0061(6) 0.0016(6) C21 0.0440(9) 0.0492(9) 0.0314(6) -0.0107(6) 0.0045(6) -0.0168(7) C10 0.0365(8) 0.0384(7) 0.0356(6) 0.0078(6) 0.0110(6) -0.0027(6) C17 0.0251(6) 0.0381(7) 0.0281(6) -0.0070(5) -0.0011(5) -0.0015(5) C16 0.0352(7) 0.0318(7) 0.0429(7) 0.0079(6) -0.0027(6) -0.0001(6) C4 0.0355(7) 0.0303(7) 0.0408(7) 0.0032(5) -0.0051(6) -0.0071(6) C3 0.0418(8) 0.0323(7) 0.0320(6) -0.0028(5) -0.0022(6) -0.0040(6) C14 0.0301(7) 0.0351(7) 0.0472(8) -0.0093(6) -0.0016(6) 0.0026(6) C18 0.0394(7) 0.0376(7) 0.0208(5) -0.0040(5) -0.0028(5) -0.0114(6) C19 0.0480(9) 0.0409(8) 0.0307(6) 0.0018(6) -0.0082(6) -0.0081(7) C20 0.0655(11) 0.0470(9) 0.0402(8) 0.0091(7) -0.0214(8) -0.0199(8) C23 0.0580(11) 0.0688(12) 0.0355(7) -0.0086(7) 0.0083(7) -0.0338(9) C22 0.0735(13) 0.0683(12) 0.0317(7) 0.0105(7) -0.0107(8) -0.0426(10) _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 C5 1.3537(15) . ? N1 C2 1.3729(14) . ? N1 H1 0.903(15) . ? N2 C6 1.2818(16) . ? N2 C7 1.4195(15) . ? N3 C16 1.3596(17) . ? N3 C13 1.3709(16) . ? N3 H2 0.881(16) . ? C9 C8 1.3801(18) . ? C9 C10 1.3867(19) . ? C9 H9 0.958(15) . ? C13 C14 1.3865(18) . ? C13 C17 1.4246(18) . ? C5 C4 1.3696(18) . ? C5 H5 0.932(13) . ? C6 C2 1.4265(17) . ? C6 H6 1.003(13) . ? C12 C11 1.3837(18) . ? C12 C7 1.3967(16) . ? C12 H12 0.987(14) . ? C8 C7 1.3909(18) . ? C8 H8 0.973(14) . ? C11 C10 1.383(2) . ? C11 H11 0.983(16) . ? N4 C17 1.2812(16) . ? N4 C18 1.4192(16) . ? C2 C3 1.3802(17) . ? C15 C16 1.371(2) . ? C15 C14 1.394(2) . ? C15 H15 0.977(17) . ? C21 C23 1.386(2) . ? C21 C18 1.3950(19) . ? C21 H23 1.002(16) . ? C10 H10 0.970(15) . ? C17 H17 1.002(14) . ? C16 H16 0.976(15) . ? C4 C3 1.3974(18) . ? C4 H4 0.972(16) . ? C3 H3 0.964(13) . ? C14 H14 0.979(16) . ? C18 C19 1.392(2) . ? C19 C20 1.390(2) . ? C19 H19 0.994(17) . ? C20 C22 1.384(3) . ? C20 H20 0.992(17) . ? C23 C22 1.377(3) . ? C23 H22 1.013(19) . ? C22 H21 0.955(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C2 109.04(10) . . ? C5 N1 H1 124.8(9) . . ? C2 N1 H1 125.9(9) . . ? C6 N2 C7 117.77(9) . . ? C16 N3 C13 109.05(11) . . ? C16 N3 H2 123.7(10) . . ? C13 N3 H2 127.2(10) . . ? C8 C9 C10 120.57(13) . . ? C8 C9 H9 120.5(9) . . ? C10 C9 H9 118.9(9) . . ? N3 C13 C14 107.17(11) . . ? N3 C13 C17 124.82(11) . . ? C14 C13 C17 127.90(12) . . ? N1 C5 C4 108.89(11) . . ? N1 C5 H5 121.2(8) . . ? C4 C5 H5 129.9(8) . . ? N2 C6 C2 124.34(11) . . ? N2 C6 H6 121.8(8) . . ? C2 C6 H6 113.8(8) . . ? C11 C12 C7 120.02(12) . . ? C11 C12 H12 119.3(8) . . ? C7 C12 H12 120.7(8) . . ? C9 C8 C7 120.18(12) . . ? C9 C8 H8 121.2(8) . . ? C7 C8 H8 118.6(8) . . ? C10 C11 C12 120.52(12) . . ? C10 C11 H11 120.5(9) . . ? C12 C11 H11 119.0(9) . . ? C17 N4 C18 117.30(10) . . ? C8 C7 C12 119.25(11) . . ? C8 C7 N2 118.50(10) . . ? C12 C7 N2 122.15(11) . . ? N1 C2 C3 107.23(11) . . ? N1 C2 C6 124.16(11) . . ? C3 C2 C6 128.55(11) . . ? C16 C15 C14 107.12(12) . . ? C16 C15 H15 125.2(9) . . ? C14 C15 H15 127.7(9) . . ? C23 C21 C18 119.59(16) . . ? C23 C21 H23 121.2(9) . . ? C18 C21 H23 119.2(9) . . ? C11 C10 C9 119.44(12) . . ? C11 C10 H10 121.6(8) . . ? C9 C10 H10 119.0(8) . . ? N4 C17 C13 124.73(11) . . ? N4 C17 H17 121.4(8) . . ? C13 C17 H17 113.8(8) . . ? N3 C16 C15 108.75(12) . . ? N3 C16 H16 121.7(9) . . ? C15 C16 H16 129.5(9) . . ? C5 C4 C3 106.97(12) . . ? C5 C4 H4 126.2(9) . . ? C3 C4 H4 126.8(9) . . ? C2 C3 C4 107.86(11) . . ? C2 C3 H3 125.2(9) . . ? C4 C3 H3 126.9(9) . . ? C13 C14 C15 107.91(12) . . ? C13 C14 H14 123.7(9) . . ? C15 C14 H14 128.4(9) . . ? C19 C18 C21 119.58(13) . . ? C19 C18 N4 117.84(12) . . ? C21 C18 N4 122.54(13) . . ? C20 C19 C18 120.04(16) . . ? C20 C19 H19 122.2(10) . . ? C18 C19 H19 117.8(9) . . ? C22 C20 C19 120.02(17) . . ? C22 C20 H20 122.9(10) . . ? C19 C20 H20 117.1(10) . . ? C22 C23 C21 120.72(17) . . ? C22 C23 H22 121.8(10) . . ? C21 C23 H22 117.5(10) . . ? C23 C22 C20 119.98(15) . . ? C23 C22 H21 118.4(11) . . ? C20 C22 H21 121.6(11) . . ? 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 C16 N3 C13 C14 -0.49(14) . . . . ? C16 N3 C13 C17 -177.02(12) . . . . ? C2 N1 C5 C4 0.88(14) . . . . ? C7 N2 C6 C2 -176.93(11) . . . . ? C10 C9 C8 C7 1.0(2) . . . . ? C7 C12 C11 C10 -0.5(2) . . . . ? C9 C8 C7 C12 -1.04(18) . . . . ? C9 C8 C7 N2 -177.50(11) . . . . ? C11 C12 C7 C8 0.78(18) . . . . ? C11 C12 C7 N2 177.10(11) . . . . ? C6 N2 C7 C8 -137.68(12) . . . . ? C6 N2 C7 C12 45.98(16) . . . . ? C5 N1 C2 C3 -0.88(14) . . . . ? C5 N1 C2 C6 176.73(11) . . . . ? N2 C6 C2 N1 2.35(19) . . . . ? N2 C6 C2 C3 179.44(13) . . . . ? C12 C11 C10 C9 0.4(2) . . . . ? C8 C9 C10 C11 -0.6(2) . . . . ? C18 N4 C17 C13 179.25(12) . . . . ? N3 C13 C17 N4 3.5(2) . . . . ? C14 C13 C17 N4 -172.29(13) . . . . ? C13 N3 C16 C15 0.45(15) . . . . ? C14 C15 C16 N3 -0.23(16) . . . . ? N1 C5 C4 C3 -0.53(15) . . . . ? N1 C2 C3 C4 0.54(15) . . . . ? C6 C2 C3 C4 -176.93(12) . . . . ? C5 C4 C3 C2 -0.01(16) . . . . ? N3 C13 C14 C15 0.34(15) . . . . ? C17 C13 C14 C15 176.74(13) . . . . ? C16 C15 C14 C13 -0.07(16) . . . . ? C23 C21 C18 C19 3.01(19) . . . . ? C23 C21 C18 N4 -179.05(12) . . . . ? C17 N4 C18 C19 -141.02(12) . . . . ? C17 N4 C18 C21 41.00(17) . . . . ? C21 C18 C19 C20 -2.14(19) . . . . ? N4 C18 C19 C20 179.82(12) . . . . ? C18 C19 C20 C22 -0.1(2) . . . . ? C18 C21 C23 C22 -1.7(2) . . . . ? C21 C23 C22 C20 -0.5(2) . . . . ? C19 C20 C22 C23 1.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.12 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.195 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.038 ################################################################################ data_Ligand_precursor_I-A_(polymorph_I) _database_code_depnum_ccdc_archive 'CCDC 727071' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C11 H10 N2' _chemical_formula_sum 'C11 H10 N2' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 150(2) _chemical_formula_weight 170.21 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 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0440(14) _cell_length_b 18.727(2) _cell_length_c 16.3890(18) _cell_angle_alpha 90.00 _cell_angle_beta 91.941(8) _cell_angle_gamma 90.00 _cell_volume 3694.4(7) _cell_formula_units_Z 16 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6493 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 25.12 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9567 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 99633 _diffrn_reflns_av_R_equivalents 0.1160 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 25.12 _reflns_number_total 6493 _reflns_number_gt 3996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material enCIFer _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^)+(0.0577P)^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 0.0027(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6493 _refine_ls_number_parameters 630 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1035 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.004 _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 N2 N 0.42706(13) 0.87250(9) 0.50118(10) 0.0271(4) Uani 1 1 d . . . N3 N 0.40391(14) 0.67330(9) 0.83487(11) 0.0286(4) Uani 1 1 d . . . N4 N 0.20191(13) 0.58988(9) 0.81412(10) 0.0264(4) Uani 1 1 d . . . N8 N 0.50770(14) 0.12907(9) 0.01051(10) 0.0301(4) Uani 1 1 d . . . N6 N -0.30213(13) 0.84629(9) 0.80459(10) 0.0265(4) Uani 1 1 d . . . C18 C 0.10150(16) 0.55041(10) 0.80058(12) 0.0244(5) Uani 1 1 d . . . N5 N -0.50608(14) 0.92582(10) 0.81689(12) 0.0307(5) Uani 1 1 d . . . C17 C 0.25224(17) 0.61558(11) 0.75316(13) 0.0271(5) Uani 1 1 d . . . N1 N 0.18915(15) 0.84745(10) 0.48382(12) 0.0304(5) Uani 1 1 d . . . C23 C 0.05937(18) 0.51681(11) 0.86821(14) 0.0304(5) Uani 1 1 d . . . C13 C 0.34909(16) 0.65925(11) 0.76149(12) 0.0256(5) Uani 1 1 d . . . C34 C -0.19777(19) 0.73695(12) 0.81206(13) 0.0321(5) Uani 1 1 d . . . C6 C 0.36995(17) 0.85213(11) 0.56127(13) 0.0293(5) Uani 1 1 d . . . C7 C 0.54483(16) 0.87598(11) 0.51215(11) 0.0256(5) Uani 1 1 d . . . C24 C -0.42881(16) 0.93684(11) 0.75876(12) 0.0258(5) Uani 1 1 d . . . C40 C 0.62141(17) 0.11118(11) 0.00382(12) 0.0284(5) Uani 1 1 d . . . C33 C -0.09938(19) 0.69930(13) 0.80772(14) 0.0359(6) Uani 1 1 d . . . C28 C -0.32821(17) 0.89710(11) 0.75491(13) 0.0279(5) Uani 1 1 d . . . C45 C 0.6562(2) 0.04948(13) -0.03456(14) 0.0353(6) Uani 1 1 d . . . C29 C -0.19975(16) 0.81000(11) 0.79604(12) 0.0264(5) Uani 1 1 d . . . C32 C -0.0019(2) 0.73440(13) 0.79021(13) 0.0372(6) Uani 1 1 d . . . C16 C 0.48960(18) 0.71811(12) 0.82214(14) 0.0334(6) Uani 1 1 d . . . C27 C -0.59265(19) 0.97090(12) 0.80293(14) 0.0346(6) Uani 1 1 d . . . C25 C -0.46928(19) 0.99000(12) 0.70793(14) 0.0326(6) Uani 1 1 d . . . C38 C 0.16131(19) 0.16259(12) -0.00371(15) 0.0339(6) Uani 1 1 d . . . C8 C 0.60539(18) 0.82219(12) 0.55143(13) 0.0312(5) Uani 1 1 d . . . C14 C 0.40223(18) 0.69719(11) 0.70223(13) 0.0303(5) Uani 1 1 d . . . C12 C 0.60109(18) 0.93231(13) 0.47779(14) 0.0343(6) Uani 1 1 d . . . C19 C 0.04098(18) 0.54609(12) 0.72663(14) 0.0319(5) Uani 1 1 d . . . C31 C -0.00357(19) 0.80723(13) 0.77585(13) 0.0366(6) Uani 1 1 d . . . C22 C -0.04100(19) 0.48049(12) 0.86294(15) 0.0349(6) Uani 1 1 d . . . C30 C -0.10185(17) 0.84495(13) 0.77828(13) 0.0310(5) Uani 1 1 d . . . C9 C 0.72008(19) 0.82571(13) 0.55807(14) 0.0372(6) Uani 1 1 d . . . C5 C 0.08407(18) 0.82449(12) 0.49629(15) 0.0339(6) Uani 1 1 d . . . C44 C 0.7686(2) 0.03301(14) -0.03598(15) 0.0416(6) Uani 1 1 d . . . C21 C -0.10064(19) 0.47743(12) 0.78951(15) 0.0358(6) Uani 1 1 d . . . C41 C 0.7009(2) 0.15528(14) 0.04088(15) 0.0390(6) Uani 1 1 d . . . C10 C 0.7749(2) 0.88239(14) 0.52486(16) 0.0440(7) Uani 1 1 d . . . C26 C -0.57232(19) 1.01120(13) 0.73565(14) 0.0368(6) Uani 1 1 d . . . C20 C -0.05930(18) 0.50977(12) 0.72105(15) 0.0345(6) Uani 1 1 d . . . C43 C 0.8469(2) 0.07774(14) -0.00010(16) 0.0449(7) Uani 1 1 d . . . C15 C 0.49033(19) 0.73458(12) 0.74062(13) 0.0351(6) Uani 1 1 d . . . C42 C 0.8122(2) 0.13879(15) 0.03811(16) 0.0460(7) Uani 1 1 d . . . C11 C 0.71537(19) 0.93588(15) 0.48471(15) 0.0425(6) Uani 1 1 d . . . C2 C 0.25327(16) 0.83830(11) 0.55388(12) 0.0270(5) Uani 1 1 d . . . C39 C 0.44181(18) 0.12077(11) -0.05225(14) 0.0295(5) Uani 1 1 d . . . C3 C 0.18551(18) 0.80903(12) 0.61122(14) 0.0319(5) Uani 1 1 d . . . C35 C 0.32507(16) 0.13455(11) -0.05194(12) 0.0275(5) Uani 1 1 d . . . C4 C 0.07968(19) 0.80018(12) 0.57422(14) 0.0335(6) Uani 1 1 d . . . C36 C 0.24704(19) 0.13239(12) -0.11554(14) 0.0350(6) Uani 1 1 d . . . C37 C 0.1443(2) 0.15010(12) -0.08494(15) 0.0371(6) Uani 1 1 d . . . N7 N 0.27057(15) 0.15326(10) 0.01664(12) 0.0300(5) Uani 1 1 d . . . H05 H -0.4966(17) 0.8976(12) 0.8602(14) 0.041(7) Uiso 1 1 d . . . H19 H 0.0672(16) 0.5690(11) 0.6794(13) 0.033(6) Uiso 1 1 d . . . H38 H 0.1141(17) 0.1754(11) 0.0325(12) 0.030(6) Uiso 1 1 d . . . H14 H 0.3805(15) 0.6972(10) 0.6424(12) 0.024(5) Uiso 1 1 d . . . H20 H -0.1006(17) 0.5063(11) 0.6687(13) 0.038(6) Uiso 1 1 d . . . H01 H 0.2101(17) 0.8666(11) 0.4422(13) 0.031(7) Uiso 1 1 d . . . H45 H 0.6013(16) 0.0190(11) -0.0617(12) 0.034(6) Uiso 1 1 d . . . H39 H 0.4680(15) 0.1079(10) -0.1081(13) 0.033(6) Uiso 1 1 d . . . H28 H -0.2826(15) 0.9103(10) 0.7070(12) 0.030(5) Uiso 1 1 d . . . H16 H 0.5394(15) 0.7339(10) 0.8656(12) 0.025(5) Uiso 1 1 d . . . H27 H -0.6584(17) 0.9690(11) 0.8379(12) 0.039(6) Uiso 1 1 d . . . H10 H 0.8556(19) 0.8846(12) 0.5311(13) 0.044(6) Uiso 1 1 d . . . H32 H 0.0682(18) 0.7073(12) 0.7845(12) 0.043(6) Uiso 1 1 d . . . H23 H 0.0998(16) 0.5167(11) 0.9186(13) 0.037(6) Uiso 1 1 d . . . H31 H 0.0679(17) 0.8341(11) 0.7643(12) 0.035(6) Uiso 1 1 d . . . H8 H 0.5667(16) 0.7784(11) 0.5748(12) 0.037(6) Uiso 1 1 d . . . H4 H 0.0148(17) 0.7820(11) 0.5996(12) 0.034(6) Uiso 1 1 d . . . H17 H 0.2254(16) 0.6061(11) 0.6938(13) 0.038(6) Uiso 1 1 d . . . H25 H -0.4281(16) 1.0067(11) 0.6635(13) 0.036(6) Uiso 1 1 d . . . H6 H 0.4027(18) 0.8418(12) 0.6183(14) 0.051(7) Uiso 1 1 d . . . H5 H 0.0290(17) 0.8271(11) 0.4559(13) 0.038(7) Uiso 1 1 d . . . H21 H -0.1726(19) 0.4528(12) 0.7851(13) 0.046(7) Uiso 1 1 d . . . H12 H 0.5604(17) 0.9694(12) 0.4509(12) 0.036(6) Uiso 1 1 d . . . H3 H 0.2083(16) 0.7946(11) 0.6678(13) 0.039(6) Uiso 1 1 d . . . H07 H 0.3012(17) 0.1566(12) 0.0617(13) 0.035(7) Uiso 1 1 d . . . H26 H -0.6236(17) 1.0473(12) 0.7138(13) 0.041(6) Uiso 1 1 d . . . H22 H -0.0693(18) 0.4565(12) 0.9115(14) 0.048(7) Uiso 1 1 d . . . H36 H 0.2641(16) 0.1229(11) -0.1700(13) 0.032(6) Uiso 1 1 d . . . H33 H -0.0989(17) 0.6453(13) 0.8191(13) 0.051(7) Uiso 1 1 d . . . H44 H 0.7906(18) -0.0096(13) -0.0653(13) 0.047(7) Uiso 1 1 d . . . H03 H 0.3936(19) 0.6523(13) 0.8833(14) 0.053(8) Uiso 1 1 d . . . H15 H 0.5467(18) 0.7655(12) 0.7126(13) 0.044(6) Uiso 1 1 d . . . H41 H 0.6751(18) 0.1925(13) 0.0681(14) 0.045(7) Uiso 1 1 d . . . H30 H -0.1000(17) 0.8978(13) 0.7684(13) 0.048(7) Uiso 1 1 d . . . H11 H 0.7538(19) 0.9739(14) 0.4589(14) 0.054(7) Uiso 1 1 d . . . H9 H 0.7615(18) 0.7885(13) 0.5864(13) 0.046(7) Uiso 1 1 d . . . H37 H 0.0730(18) 0.1542(11) -0.1131(13) 0.044(7) Uiso 1 1 d . . . H43 H 0.9261(19) 0.0651(12) -0.0005(13) 0.048(7) Uiso 1 1 d . . . H42 H 0.863(2) 0.1665(14) 0.0630(15) 0.064(9) Uiso 1 1 d . . . H34 H -0.2708(18) 0.7122(12) 0.8276(13) 0.049(7) 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 N2 0.0254(10) 0.0292(10) 0.0266(10) 0.0011(8) 0.0017(8) -0.0008(8) N3 0.0275(10) 0.0311(11) 0.0274(11) 0.0011(8) 0.0028(9) -0.0037(9) N4 0.0242(10) 0.0245(10) 0.0304(10) 0.0006(8) 0.0000(8) 0.0032(8) N8 0.0287(10) 0.0308(11) 0.0308(11) 0.0019(8) 0.0015(9) -0.0024(8) N6 0.0258(10) 0.0229(10) 0.0308(10) -0.0015(8) 0.0017(8) 0.0014(8) C18 0.0214(11) 0.0210(12) 0.0306(12) -0.0010(9) 0.0008(10) 0.0030(9) N5 0.0289(11) 0.0302(11) 0.0330(11) 0.0057(9) 0.0017(9) 0.0054(9) C17 0.0299(12) 0.0255(13) 0.0260(12) -0.0031(10) 0.0005(10) 0.0035(10) N1 0.0281(11) 0.0359(12) 0.0274(11) 0.0033(9) 0.0045(9) 0.0000(9) C23 0.0332(13) 0.0272(13) 0.0309(13) 0.0003(10) 0.0011(11) 0.0028(10) C13 0.0234(11) 0.0264(12) 0.0268(12) -0.0031(9) -0.0011(10) 0.0022(9) C34 0.0334(14) 0.0292(14) 0.0337(13) 0.0003(10) -0.0023(11) 0.0018(11) C6 0.0332(13) 0.0277(13) 0.0269(13) 0.0008(10) 0.0013(11) 0.0049(10) C7 0.0257(12) 0.0318(13) 0.0193(11) -0.0035(9) 0.0011(9) 0.0003(10) C24 0.0258(12) 0.0239(12) 0.0276(12) -0.0013(9) 0.0003(10) 0.0015(10) C40 0.0287(12) 0.0299(13) 0.0269(12) 0.0050(10) 0.0045(10) -0.0029(10) C33 0.0400(15) 0.0296(15) 0.0377(14) -0.0009(10) -0.0041(11) 0.0071(12) C28 0.0292(12) 0.0270(13) 0.0274(12) -0.0017(10) 0.0001(10) -0.0036(10) C45 0.0390(15) 0.0311(14) 0.0359(14) 0.0030(11) 0.0032(12) -0.0039(12) C29 0.0281(12) 0.0285(13) 0.0227(11) -0.0022(9) -0.0003(9) 0.0042(10) C32 0.0345(14) 0.0407(16) 0.0367(14) 0.0000(11) 0.0040(11) 0.0140(12) C16 0.0288(13) 0.0373(14) 0.0341(14) -0.0053(11) 0.0000(11) -0.0099(11) C27 0.0287(13) 0.0387(15) 0.0365(14) 0.0012(11) 0.0031(11) 0.0086(11) C25 0.0334(14) 0.0323(14) 0.0321(13) 0.0019(11) 0.0003(11) 0.0012(11) C38 0.0274(14) 0.0354(15) 0.0389(15) -0.0021(11) 0.0013(12) -0.0002(11) C8 0.0345(14) 0.0287(14) 0.0304(12) -0.0023(10) 0.0008(11) 0.0027(11) C14 0.0330(13) 0.0329(14) 0.0251(13) 0.0016(10) 0.0031(11) -0.0012(11) C12 0.0317(14) 0.0363(15) 0.0348(14) 0.0085(11) 0.0017(11) 0.0001(11) C19 0.0299(13) 0.0320(14) 0.0336(14) 0.0039(11) -0.0035(11) 0.0029(11) C31 0.0297(13) 0.0414(16) 0.0393(14) 0.0082(11) 0.0095(11) 0.0044(12) C22 0.0327(14) 0.0293(14) 0.0431(15) 0.0027(11) 0.0064(12) -0.0013(11) C30 0.0303(13) 0.0288(14) 0.0343(13) 0.0045(10) 0.0051(10) 0.0003(11) C9 0.0331(14) 0.0353(15) 0.0431(15) -0.0081(12) -0.0031(12) 0.0078(12) C5 0.0225(13) 0.0393(15) 0.0399(15) -0.0045(11) 0.0016(12) -0.0002(11) C44 0.0385(16) 0.0343(16) 0.0526(16) 0.0070(12) 0.0088(13) 0.0052(13) C21 0.0259(13) 0.0288(14) 0.0524(16) -0.0008(11) -0.0007(12) -0.0003(11) C41 0.0365(15) 0.0391(16) 0.0414(15) -0.0030(12) 0.0028(12) -0.0009(12) C10 0.0249(14) 0.0533(18) 0.0537(16) -0.0142(13) -0.0010(13) 0.0007(13) C26 0.0356(14) 0.0376(15) 0.0371(14) 0.0047(11) -0.0024(11) 0.0123(12) C20 0.0281(13) 0.0306(14) 0.0440(15) 0.0009(11) -0.0093(12) 0.0010(11) C43 0.0333(15) 0.0482(18) 0.0535(17) 0.0133(13) 0.0048(13) 0.0040(14) C15 0.0356(14) 0.0368(14) 0.0333(14) 0.0024(11) 0.0048(11) -0.0078(11) C42 0.0343(15) 0.0543(19) 0.0490(17) 0.0048(13) -0.0045(13) -0.0113(14) C11 0.0302(14) 0.0485(17) 0.0493(16) 0.0078(13) 0.0064(12) -0.0063(13) C2 0.0261(12) 0.0302(13) 0.0246(12) 0.0013(9) -0.0002(10) 0.0024(10) C39 0.0357(14) 0.0245(13) 0.0283(13) 0.0026(10) 0.0022(11) -0.0025(10) C3 0.0328(13) 0.0336(14) 0.0295(13) 0.0048(10) 0.0055(11) 0.0038(10) C35 0.0298(12) 0.0263(13) 0.0263(12) -0.0002(9) -0.0001(10) 0.0007(10) C4 0.0286(13) 0.0369(14) 0.0355(14) 0.0019(11) 0.0096(11) 0.0004(11) C36 0.0415(15) 0.0341(14) 0.0291(13) -0.0026(10) -0.0020(12) 0.0020(11) C37 0.0329(14) 0.0349(14) 0.0430(16) -0.0088(11) -0.0074(12) 0.0011(11) N7 0.0297(11) 0.0328(11) 0.0273(11) -0.0010(9) -0.0029(10) -0.0015(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C6 1.278(3) . ? N2 C7 1.425(2) . ? N3 C16 1.352(3) . ? N3 C13 1.377(3) . ? N4 C17 1.280(3) . ? N4 C18 1.428(2) . ? N8 C39 1.287(3) . ? N8 C40 1.418(3) . ? N6 C28 1.284(3) . ? N6 C29 1.419(2) . ? C18 C23 1.386(3) . ? C18 C19 1.395(3) . ? N5 C27 1.355(3) . ? N5 C24 1.370(3) . ? C17 C13 1.427(3) . ? N1 C5 1.359(3) . ? N1 C2 1.373(3) . ? C23 C22 1.387(3) . ? C13 C14 1.378(3) . ? C34 C33 1.383(3) . ? C34 C29 1.393(3) . ? C6 C2 1.430(3) . ? C7 C12 1.384(3) . ? C7 C8 1.389(3) . ? C24 C25 1.377(3) . ? C24 C28 1.425(3) . ? C40 C45 1.387(3) . ? C40 C41 1.388(3) . ? C33 C32 1.384(3) . ? C45 C44 1.388(3) . ? C29 C30 1.388(3) . ? C32 C31 1.384(3) . ? C16 C15 1.371(3) . ? C27 C26 1.365(3) . ? C25 C26 1.394(3) . ? C38 N7 1.358(3) . ? C38 C37 1.360(3) . ? C8 C9 1.383(3) . ? C14 C15 1.402(3) . ? C12 C11 1.379(3) . ? C19 C20 1.387(3) . ? C31 C30 1.380(3) . ? C22 C21 1.382(3) . ? C9 C10 1.373(3) . ? C5 C4 1.359(3) . ? C44 C43 1.379(3) . ? C21 C20 1.382(3) . ? C41 C42 1.378(3) . ? C10 C11 1.385(4) . ? C43 C42 1.376(4) . ? C2 C3 1.379(3) . ? C39 C35 1.430(3) . ? C3 C4 1.403(3) . ? C35 N7 1.366(3) . ? C35 C36 1.380(3) . ? C36 C37 1.391(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 C6 N2 C7 118.40(18) . . ? C16 N3 C13 109.25(18) . . ? C17 N4 C18 119.61(18) . . ? C39 N8 C40 118.73(18) . . ? C28 N6 C29 119.13(17) . . ? C23 C18 C19 118.3(2) . . ? C23 C18 N4 116.22(19) . . ? C19 C18 N4 125.43(18) . . ? C27 N5 C24 109.01(19) . . ? N4 C17 C13 123.2(2) . . ? C5 N1 C2 109.58(19) . . ? C18 C23 C22 121.0(2) . . ? N3 C13 C14 107.24(18) . . ? N3 C13 C17 123.98(19) . . ? C14 C13 C17 128.7(2) . . ? C33 C34 C29 120.0(2) . . ? N2 C6 C2 122.8(2) . . ? C12 C7 C8 119.0(2) . . ? C12 C7 N2 118.85(19) . . ? C8 C7 N2 122.01(19) . . ? N5 C24 C25 107.14(18) . . ? N5 C24 C28 123.42(19) . . ? C25 C24 C28 129.4(2) . . ? C45 C40 C41 118.6(2) . . ? C45 C40 N8 122.7(2) . . ? C41 C40 N8 118.6(2) . . ? C34 C33 C32 120.2(2) . . ? N6 C28 C24 123.29(19) . . ? C40 C45 C44 120.2(2) . . ? C30 C29 C34 119.6(2) . . ? C30 C29 N6 122.82(19) . . ? C34 C29 N6 117.46(18) . . ? C33 C32 C31 119.7(2) . . ? N3 C16 C15 108.7(2) . . ? N5 C27 C26 108.8(2) . . ? C24 C25 C26 108.0(2) . . ? N7 C38 C37 109.3(2) . . ? C9 C8 C7 120.6(2) . . ? C13 C14 C15 107.7(2) . . ? C11 C12 C7 120.3(2) . . ? C20 C19 C18 120.9(2) . . ? C30 C31 C32 120.4(2) . . ? C21 C22 C23 120.1(2) . . ? C31 C30 C29 120.0(2) . . ? C10 C9 C8 119.9(2) . . ? N1 C5 C4 108.3(2) . . ? C43 C44 C45 120.7(3) . . ? C22 C21 C20 119.9(2) . . ? C42 C41 C40 120.6(2) . . ? C9 C10 C11 119.9(2) . . ? C27 C26 C25 107.0(2) . . ? C21 C20 C19 119.9(2) . . ? C42 C43 C44 119.0(2) . . ? C16 C15 C14 107.2(2) . . ? C43 C42 C41 120.8(3) . . ? C12 C11 C10 120.2(2) . . ? N1 C2 C3 106.89(18) . . ? N1 C2 C6 124.86(19) . . ? C3 C2 C6 128.1(2) . . ? N8 C39 C35 123.7(2) . . ? C2 C3 C4 107.61(19) . . ? N7 C35 C36 107.16(19) . . ? N7 C35 C39 123.3(2) . . ? C36 C35 C39 129.5(2) . . ? C5 C4 C3 107.6(2) . . ? C35 C36 C37 108.2(2) . . ? C38 C37 C36 106.7(2) . . ? C38 N7 C35 108.6(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 C17 N4 C18 C23 172.22(18) . . . . ? C17 N4 C18 C19 -11.0(3) . . . . ? C18 N4 C17 C13 176.06(18) . . . . ? C19 C18 C23 C22 -0.8(3) . . . . ? N4 C18 C23 C22 176.27(18) . . . . ? C16 N3 C13 C14 -0.6(2) . . . . ? C16 N3 C13 C17 -177.94(19) . . . . ? N4 C17 C13 N3 5.8(3) . . . . ? N4 C17 C13 C14 -171.0(2) . . . . ? C7 N2 C6 C2 -172.03(19) . . . . ? C6 N2 C7 C12 -140.6(2) . . . . ? C6 N2 C7 C8 43.9(3) . . . . ? C27 N5 C24 C25 0.0(2) . . . . ? C27 N5 C24 C28 -178.8(2) . . . . ? C39 N8 C40 C45 -43.6(3) . . . . ? C39 N8 C40 C41 139.9(2) . . . . ? C29 C34 C33 C32 2.2(3) . . . . ? C29 N6 C28 C24 -179.75(18) . . . . ? N5 C24 C28 N6 1.6(3) . . . . ? C25 C24 C28 N6 -176.9(2) . . . . ? C41 C40 C45 C44 -0.5(3) . . . . ? N8 C40 C45 C44 -177.0(2) . . . . ? C33 C34 C29 C30 -2.0(3) . . . . ? C33 C34 C29 N6 -177.56(19) . . . . ? C28 N6 C29 C30 40.9(3) . . . . ? C28 N6 C29 C34 -143.7(2) . . . . ? C34 C33 C32 C31 -1.0(3) . . . . ? C13 N3 C16 C15 1.0(2) . . . . ? C24 N5 C27 C26 0.2(3) . . . . ? N5 C24 C25 C26 -0.1(2) . . . . ? C28 C24 C25 C26 178.5(2) . . . . ? C12 C7 C8 C9 1.7(3) . . . . ? N2 C7 C8 C9 177.25(19) . . . . ? N3 C13 C14 C15 0.0(2) . . . . ? C17 C13 C14 C15 177.2(2) . . . . ? C8 C7 C12 C11 -1.9(3) . . . . ? N2 C7 C12 C11 -177.6(2) . . . . ? C23 C18 C19 C20 0.7(3) . . . . ? N4 C18 C19 C20 -176.05(19) . . . . ? C33 C32 C31 C30 -0.5(3) . . . . ? C18 C23 C22 C21 0.0(3) . . . . ? C32 C31 C30 C29 0.6(3) . . . . ? C34 C29 C30 C31 0.6(3) . . . . ? N6 C29 C30 C31 175.9(2) . . . . ? C7 C8 C9 C10 -0.7(3) . . . . ? C2 N1 C5 C4 -0.2(2) . . . . ? C40 C45 C44 C43 -0.6(4) . . . . ? C23 C22 C21 C20 0.9(3) . . . . ? C45 C40 C41 C42 1.3(3) . . . . ? N8 C40 C41 C42 178.0(2) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? N5 C27 C26 C25 -0.3(3) . . . . ? C24 C25 C26 C27 0.2(3) . . . . ? C22 C21 C20 C19 -1.0(3) . . . . ? C18 C19 C20 C21 0.2(3) . . . . ? C45 C44 C43 C42 0.7(4) . . . . ? N3 C16 C15 C14 -0.9(3) . . . . ? C13 C14 C15 C16 0.6(3) . . . . ? C44 C43 C42 C41 0.1(4) . . . . ? C40 C41 C42 C43 -1.2(4) . . . . ? C7 C12 C11 C10 1.2(4) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C5 N1 C2 C3 -0.2(2) . . . . ? C5 N1 C2 C6 175.5(2) . . . . ? N2 C6 C2 N1 -2.4(3) . . . . ? N2 C6 C2 C3 172.4(2) . . . . ? C40 N8 C39 C35 177.68(19) . . . . ? N1 C2 C3 C4 0.5(2) . . . . ? C6 C2 C3 C4 -175.0(2) . . . . ? N8 C39 C35 N7 -4.6(3) . . . . ? N8 C39 C35 C36 175.3(2) . . . . ? N1 C5 C4 C3 0.5(3) . . . . ? C2 C3 C4 C5 -0.6(2) . . . . ? N7 C35 C36 C37 0.1(2) . . . . ? C39 C35 C36 C37 -179.9(2) . . . . ? N7 C38 C37 C36 0.1(3) . . . . ? C35 C36 C37 C38 -0.1(3) . . . . ? C37 C38 N7 C35 0.0(3) . . . . ? C36 C35 N7 C38 0.0(2) . . . . ? C39 C35 N7 C38 179.89(19) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.12 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.214 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.048 ################################################################################ data_Ligand_precursor_IV _database_code_depnum_ccdc_archive 'CCDC 727072' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C17 H22 N2' _chemical_formula_sum 'C17 H22 N2' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour yellow _diffrn_ambient_temperature 150(2) _chemical_formula_weight 254.37 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 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 17.197(2) _cell_length_b 10.6030(11) _cell_length_c 17.6180(19) _cell_angle_alpha 90.00 _cell_angle_beta 108.648(6) _cell_angle_gamma 90.00 _cell_volume 3043.8(6) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7137 _cell_measurement_theta_min 2.01 _cell_measurement_theta_max 27.75 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9744 _exptl_absorpt_correction_T_max 0.9871 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 47202 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.75 _reflns_number_total 7137 _reflns_number_gt 4421 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material enCIFer _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^)+(0.0702P)^2^+0.2811P] 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 7137 _refine_ls_number_parameters 351 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0994 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1473 _refine_ls_wR_factor_gt 0.1316 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.48801(8) -0.24105(14) 0.70559(8) 0.0252(3) Uani 1 1 d . . . N3 N 0.50592(8) 0.15217(13) 0.78127(8) 0.0266(3) Uani 1 1 d . . . N4 N 0.60028(8) -0.07547(13) 0.83577(8) 0.0239(3) Uani 1 1 d . . . N2 N 0.39519(8) -0.01182(13) 0.65025(8) 0.0255(3) Uani 1 1 d . . . C23 C 0.61883(9) 0.02889(16) 0.87332(9) 0.0238(4) Uani 1 1 d . . . H23 H 0.6633 0.0302 0.9203 0.029 Uiso 1 1 calc R . . C26 C 0.74553(10) -0.34362(16) 0.87108(10) 0.0288(4) Uani 1 1 d . . . H26 H 0.7899 -0.3712 0.8561 0.035 Uiso 1 1 calc R . . C24 C 0.64417(9) -0.18731(15) 0.86934(9) 0.0218(3) Uani 1 1 d . . . C25 C 0.71101(9) -0.22589(16) 0.84535(9) 0.0252(4) Uani 1 1 d . . . C6 C 0.37593(9) -0.11656(16) 0.61354(9) 0.0248(4) Uani 1 1 d . . . H6 H 0.3305 -0.1183 0.5674 0.030 Uiso 1 1 calc R . . C19 C 0.57500(9) 0.14428(15) 0.84709(9) 0.0227(3) Uani 1 1 d . . . C7 C 0.34729(9) 0.09760(15) 0.61954(9) 0.0243(4) Uani 1 1 d . . . C9 C 0.24933(10) 0.25093(18) 0.63212(10) 0.0339(4) Uani 1 1 d . . . H9 H 0.2100 0.2776 0.6545 0.041 Uiso 1 1 calc R . . C3 C 0.40585(11) -0.34882(17) 0.60410(10) 0.0325(4) Uani 1 1 d . . . H3 H 0.3637 -0.3701 0.5577 0.039 Uiso 1 1 calc R . . C21 C 0.52965(10) 0.34341(17) 0.83377(10) 0.0312(4) Uani 1 1 d . . . H21 H 0.5248 0.4292 0.8422 0.037 Uiso 1 1 calc R . . C8 C 0.28773(9) 0.13510(16) 0.65456(10) 0.0280(4) Uani 1 1 d . . . C20 C 0.59046(10) 0.26252(16) 0.88055(10) 0.0271(4) Uani 1 1 d . . . H20 H 0.6335 0.2847 0.9260 0.033 Uiso 1 1 calc R . . C2 C 0.41999(9) -0.23170(16) 0.63903(9) 0.0248(4) Uani 1 1 d . . . C29 C 0.61322(9) -0.26319(16) 0.91840(9) 0.0255(4) Uani 1 1 d . . . C28 C 0.65006(10) -0.37938(17) 0.94249(10) 0.0296(4) Uani 1 1 d . . . H28 H 0.6307 -0.4307 0.9754 0.036 Uiso 1 1 calc R . . C22 C 0.47873(10) 0.27276(16) 0.77351(11) 0.0308(4) Uani 1 1 d . . . H22 H 0.4328 0.3026 0.7335 0.037 Uiso 1 1 calc R . . C5 C 0.51600(11) -0.36156(16) 0.71260(10) 0.0311(4) Uani 1 1 d . . . H5 H 0.5615 -0.3920 0.7529 0.037 Uiso 1 1 calc R . . C11 C 0.32557(11) 0.28778(17) 0.54208(10) 0.0335(4) Uani 1 1 d . . . H11 H 0.3373 0.3395 0.5045 0.040 Uiso 1 1 calc R . . C16 C 0.43083(10) 0.13347(18) 0.52436(10) 0.0319(4) Uani 1 1 d . . . H16 H 0.4392 0.0424 0.5324 0.038 Uiso 1 1 calc R . . C33 C 0.54168(11) -0.21861(18) 0.94453(11) 0.0343(4) Uani 1 1 d . . . H33 H 0.5120 -0.1546 0.9060 0.041 Uiso 1 1 calc R . . C4 C 0.46626(11) -0.43040(17) 0.65074(11) 0.0363(4) Uani 1 1 d . . . H4 H 0.4715 -0.5158 0.6413 0.044 Uiso 1 1 calc R . . C30 C 0.74537(10) -0.13983(17) 0.79517(11) 0.0318(4) Uani 1 1 d . . . H30 H 0.6998 -0.0892 0.7612 0.038 Uiso 1 1 calc R . . C12 C 0.36585(10) 0.17262(16) 0.56167(9) 0.0268(4) Uani 1 1 d . . . C27 C 0.71481(10) -0.42026(17) 0.91857(10) 0.0305(4) Uani 1 1 d . . . H27 H 0.7378 -0.4992 0.9343 0.037 Uiso 1 1 calc R . . C10 C 0.26859(11) 0.32693(18) 0.57718(10) 0.0359(4) Uani 1 1 d . . . H10 H 0.2431 0.4049 0.5637 0.043 Uiso 1 1 calc R . . C31 C 0.78353(12) -0.2099(2) 0.74003(12) 0.0436(5) Uani 1 1 d . . . H31A H 0.8034 -0.1499 0.7097 0.065 Uiso 1 1 calc R . . H31B H 0.7429 -0.2628 0.7041 0.065 Uiso 1 1 calc R . . H31C H 0.8283 -0.2609 0.7716 0.065 Uiso 1 1 calc R . . C32 C 0.80861(11) -0.04846(19) 0.84895(13) 0.0441(5) Uani 1 1 d . . . H32A H 0.8296 0.0055 0.8163 0.066 Uiso 1 1 calc R . . H32B H 0.8529 -0.0956 0.8847 0.066 Uiso 1 1 calc R . . H32C H 0.7829 0.0018 0.8795 0.066 Uiso 1 1 calc R . . C15 C 0.23503(17) 0.1194(2) 0.77420(14) 0.0639(7) Uani 1 1 d . . . H15A H 0.2759 0.1790 0.8028 0.096 Uiso 1 1 calc R . . H15B H 0.2249 0.0604 0.8113 0.096 Uiso 1 1 calc R . . H15C H 0.1851 0.1632 0.7466 0.096 Uiso 1 1 calc R . . C35 C 0.57247(13) -0.1552(2) 1.02671(13) 0.0511(6) Uani 1 1 d . . . H35A H 0.5265 -0.1275 1.0420 0.077 Uiso 1 1 calc R . . H35B H 0.6060 -0.0839 1.0242 0.077 Uiso 1 1 calc R . . H35C H 0.6043 -0.2144 1.0655 0.077 Uiso 1 1 calc R . . C14 C 0.20037(13) -0.0453(2) 0.66840(13) 0.0503(5) Uani 1 1 d . . . H14A H 0.1868 -0.0995 0.7059 0.075 Uiso 1 1 calc R . . H14B H 0.2211 -0.0951 0.6336 0.075 Uiso 1 1 calc R . . H14C H 0.1522 -0.0007 0.6372 0.075 Uiso 1 1 calc R . . C17 C 0.40647(12) 0.1582(2) 0.43502(11) 0.0459(5) Uani 1 1 d . . . H17A H 0.4499 0.1313 0.4154 0.069 Uiso 1 1 calc R . . H17B H 0.3968 0.2467 0.4250 0.069 Uiso 1 1 calc R . . H17C H 0.3573 0.1121 0.4080 0.069 Uiso 1 1 calc R . . C34 C 0.48138(12) -0.3228(2) 0.94408(15) 0.0559(6) Uani 1 1 d . . . H34A H 0.4376 -0.2894 0.9608 0.084 Uiso 1 1 calc R . . H34B H 0.5090 -0.3884 0.9802 0.084 Uiso 1 1 calc R . . H34C H 0.4593 -0.3565 0.8909 0.084 Uiso 1 1 calc R . . C18 C 0.51174(12) 0.1972(3) 0.56664(13) 0.0644(7) Uani 1 1 d . . . H18A H 0.5520 0.1710 0.5427 0.097 Uiso 1 1 calc R . . H18B H 0.5297 0.1740 0.6222 0.097 Uiso 1 1 calc R . . H18C H 0.5050 0.2870 0.5619 0.097 Uiso 1 1 calc R . . C13 C 0.26537(11) 0.04859(18) 0.71347(11) 0.0346(4) Uani 1 1 d . . . H13 H 0.3146 0.0012 0.7431 0.041 Uiso 1 1 calc R . . H1A H 0.5119(11) -0.1774(18) 0.7370(11) 0.035(5) Uiso 1 1 d . . . H3A H 0.4778(12) 0.088(2) 0.7461(12) 0.045(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 N1 0.0275(7) 0.0227(8) 0.0248(7) 0.0006(6) 0.0075(6) 0.0008(6) N3 0.0273(7) 0.0216(8) 0.0283(7) 0.0003(6) 0.0052(6) 0.0031(6) N4 0.0227(6) 0.0243(7) 0.0251(7) 0.0024(6) 0.0081(5) 0.0043(6) N2 0.0230(7) 0.0251(8) 0.0275(7) 0.0053(6) 0.0068(6) 0.0014(6) C23 0.0214(7) 0.0290(9) 0.0223(8) 0.0017(7) 0.0090(6) 0.0015(7) C26 0.0220(8) 0.0294(9) 0.0323(9) -0.0022(7) 0.0049(7) 0.0048(7) C24 0.0193(7) 0.0217(8) 0.0207(8) -0.0009(6) 0.0014(6) 0.0018(6) C25 0.0214(8) 0.0279(9) 0.0244(8) -0.0006(7) 0.0044(6) 0.0025(7) C6 0.0210(8) 0.0294(9) 0.0228(8) 0.0022(7) 0.0054(6) -0.0005(7) C19 0.0221(8) 0.0248(9) 0.0229(8) 0.0014(7) 0.0097(6) 0.0005(7) C7 0.0215(8) 0.0244(9) 0.0221(8) 0.0012(7) -0.0001(6) -0.0014(7) C9 0.0284(9) 0.0386(11) 0.0313(9) -0.0013(8) 0.0048(7) 0.0069(8) C3 0.0343(9) 0.0320(10) 0.0298(9) -0.0037(8) 0.0080(7) -0.0025(8) C21 0.0352(9) 0.0231(9) 0.0387(10) 0.0005(8) 0.0165(8) 0.0022(8) C8 0.0238(8) 0.0312(10) 0.0253(8) 0.0013(7) 0.0026(7) 0.0007(7) C20 0.0282(8) 0.0275(9) 0.0277(8) -0.0009(7) 0.0118(7) -0.0019(7) C2 0.0243(8) 0.0277(9) 0.0238(8) 0.0008(7) 0.0096(6) -0.0007(7) C29 0.0241(8) 0.0281(9) 0.0229(8) 0.0004(7) 0.0056(6) 0.0000(7) C28 0.0314(9) 0.0281(10) 0.0262(8) 0.0051(7) 0.0049(7) -0.0018(8) C22 0.0295(9) 0.0246(9) 0.0357(9) 0.0033(8) 0.0066(7) 0.0065(8) C5 0.0357(9) 0.0240(9) 0.0338(9) 0.0047(7) 0.0115(8) 0.0058(8) C11 0.0373(10) 0.0302(10) 0.0281(9) 0.0087(7) 0.0033(8) -0.0011(8) C16 0.0344(9) 0.0310(10) 0.0308(9) 0.0059(8) 0.0111(7) 0.0017(8) C33 0.0342(9) 0.0360(11) 0.0384(10) 0.0083(8) 0.0195(8) 0.0057(8) C4 0.0441(11) 0.0232(10) 0.0420(10) -0.0021(8) 0.0144(9) 0.0022(8) C30 0.0257(8) 0.0345(10) 0.0372(10) 0.0064(8) 0.0129(7) 0.0074(8) C12 0.0264(8) 0.0254(9) 0.0250(8) 0.0020(7) 0.0031(7) -0.0018(7) C27 0.0300(9) 0.0240(9) 0.0308(9) 0.0012(7) 0.0003(7) 0.0056(7) C10 0.0376(10) 0.0302(10) 0.0328(9) 0.0044(8) 0.0012(8) 0.0106(8) C31 0.0426(11) 0.0534(13) 0.0420(11) 0.0049(10) 0.0237(9) 0.0109(10) C32 0.0366(10) 0.0382(12) 0.0644(14) 0.0011(10) 0.0259(10) -0.0044(9) C15 0.0942(18) 0.0580(16) 0.0535(14) 0.0004(12) 0.0434(14) -0.0005(14) C35 0.0603(13) 0.0494(13) 0.0571(13) -0.0137(11) 0.0376(11) -0.0092(11) C14 0.0484(12) 0.0462(13) 0.0591(14) 0.0044(11) 0.0214(10) -0.0054(10) C17 0.0374(10) 0.0686(15) 0.0331(10) 0.0033(10) 0.0133(8) -0.0049(10) C34 0.0413(11) 0.0634(16) 0.0709(15) -0.0141(12) 0.0290(11) -0.0103(11) C18 0.0290(10) 0.112(2) 0.0502(13) -0.0265(14) 0.0099(9) -0.0055(12) C13 0.0317(9) 0.0388(11) 0.0348(9) 0.0036(8) 0.0129(8) 0.0030(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 C5 1.357(2) . ? N1 C2 1.370(2) . ? N1 H1A 0.886(19) . ? N3 C22 1.353(2) . ? N3 C19 1.372(2) . ? N3 H3A 0.94(2) . ? N4 C23 1.276(2) . ? N4 C24 1.428(2) . ? N2 C6 1.275(2) . ? N2 C7 1.426(2) . ? C23 C19 1.434(2) . ? C23 H23 0.9300 . ? C26 C27 1.386(2) . ? C26 C25 1.394(2) . ? C26 H26 0.9300 . ? C24 C29 1.404(2) . ? C24 C25 1.406(2) . ? C25 C30 1.516(2) . ? C6 C2 1.431(2) . ? C6 H6 0.9300 . ? C19 C20 1.375(2) . ? C7 C12 1.408(2) . ? C7 C8 1.411(2) . ? C9 C10 1.379(3) . ? C9 C8 1.391(2) . ? C9 H9 0.9300 . ? C3 C2 1.373(2) . ? C3 C4 1.399(2) . ? C3 H3 0.9300 . ? C21 C22 1.364(2) . ? C21 C20 1.399(2) . ? C21 H21 0.9300 . ? C8 C13 1.524(2) . ? C20 H20 0.9300 . ? C29 C28 1.388(2) . ? C29 C33 1.520(2) . ? C28 C27 1.381(2) . ? C28 H28 0.9300 . ? C22 H22 0.9300 . ? C5 C4 1.362(2) . ? C5 H5 0.9300 . ? C11 C10 1.379(3) . ? C11 C12 1.392(2) . ? C11 H11 0.9300 . ? C16 C18 1.511(3) . ? C16 C17 1.517(2) . ? C16 C12 1.524(2) . ? C16 H16 0.9800 . ? C33 C34 1.513(3) . ? C33 C35 1.529(3) . ? C33 H33 0.9800 . ? C4 H4 0.9300 . ? C30 C31 1.527(2) . ? C30 C32 1.536(3) . ? C30 H30 0.9800 . ? C27 H27 0.9300 . ? C10 H10 0.9300 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C15 C13 1.529(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C14 C13 1.518(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C13 H13 0.9800 . ? 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 C2 109.09(15) . . ? C5 N1 H1A 125.5(12) . . ? C2 N1 H1A 125.3(12) . . ? C22 N3 C19 108.72(14) . . ? C22 N3 H3A 121.8(12) . . ? C19 N3 H3A 129.5(12) . . ? C23 N4 C24 119.59(13) . . ? C6 N2 C7 119.45(13) . . ? N4 C23 C19 123.67(14) . . ? N4 C23 H23 118.2 . . ? C19 C23 H23 118.2 . . ? C27 C26 C25 121.08(15) . . ? C27 C26 H26 119.5 . . ? C25 C26 H26 119.5 . . ? C29 C24 C25 121.70(15) . . ? C29 C24 N4 118.45(13) . . ? C25 C24 N4 119.43(14) . . ? C26 C25 C24 117.81(15) . . ? C26 C25 C30 121.58(14) . . ? C24 C25 C30 120.58(14) . . ? N2 C6 C2 123.95(14) . . ? N2 C6 H6 118.0 . . ? C2 C6 H6 118.0 . . ? N3 C19 C20 107.66(14) . . ? N3 C19 C23 123.26(15) . . ? C20 C19 C23 129.08(15) . . ? C12 C7 C8 121.45(15) . . ? C12 C7 N2 119.82(14) . . ? C8 C7 N2 118.39(14) . . ? C10 C9 C8 121.12(17) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C2 C3 C4 107.71(15) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? C22 C21 C20 107.14(16) . . ? C22 C21 H21 126.4 . . ? C20 C21 H21 126.4 . . ? C9 C8 C7 118.01(16) . . ? C9 C8 C13 121.67(16) . . ? C7 C8 C13 120.31(15) . . ? C19 C20 C21 107.51(15) . . ? C19 C20 H20 126.2 . . ? C21 C20 H20 126.2 . . ? N1 C2 C3 107.38(15) . . ? N1 C2 C6 123.50(15) . . ? C3 C2 C6 129.11(15) . . ? C28 C29 C24 118.09(15) . . ? C28 C29 C33 121.18(15) . . ? C24 C29 C33 120.73(15) . . ? C27 C28 C29 121.27(16) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? N3 C22 C21 108.98(15) . . ? N3 C22 H22 125.5 . . ? C21 C22 H22 125.5 . . ? N1 C5 C4 108.54(16) . . ? N1 C5 H5 125.7 . . ? C4 C5 H5 125.7 . . ? C10 C11 C12 121.44(17) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C18 C16 C17 109.86(17) . . ? C18 C16 C12 110.61(15) . . ? C17 C16 C12 113.79(14) . . ? C18 C16 H16 107.4 . . ? C17 C16 H16 107.4 . . ? C12 C16 H16 107.4 . . ? C34 C33 C29 113.02(16) . . ? C34 C33 C35 110.80(16) . . ? C29 C33 C35 110.77(15) . . ? C34 C33 H33 107.3 . . ? C29 C33 H33 107.3 . . ? C35 C33 H33 107.3 . . ? C5 C4 C3 107.28(16) . . ? C5 C4 H4 126.4 . . ? C3 C4 H4 126.4 . . ? C25 C30 C31 113.90(15) . . ? C25 C30 C32 110.55(15) . . ? C31 C30 C32 109.60(15) . . ? C25 C30 H30 107.5 . . ? C31 C30 H30 107.5 . . ? C32 C30 H30 107.5 . . ? C11 C12 C7 117.71(16) . . ? C11 C12 C16 120.50(15) . . ? C7 C12 C16 121.72(15) . . ? C28 C27 C26 120.03(16) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C9 C10 C11 120.23(17) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C13 C8 110.03(15) . . ? C14 C13 C15 109.22(17) . . ? C8 C13 C15 113.46(17) . . ? C14 C13 H13 108.0 . . ? C8 C13 H13 108.0 . . ? C15 C13 H13 108.0 . . ? 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 C24 N4 C23 C19 -175.87(14) . . . . ? C23 N4 C24 C29 91.77(18) . . . . ? C23 N4 C24 C25 -95.49(18) . . . . ? C27 C26 C25 C24 0.2(2) . . . . ? C27 C26 C25 C30 178.43(15) . . . . ? C29 C24 C25 C26 0.8(2) . . . . ? N4 C24 C25 C26 -171.72(14) . . . . ? C29 C24 C25 C30 -177.50(14) . . . . ? N4 C24 C25 C30 10.0(2) . . . . ? C7 N2 C6 C2 179.74(15) . . . . ? C22 N3 C19 C20 0.12(18) . . . . ? C22 N3 C19 C23 178.98(15) . . . . ? N4 C23 C19 N3 3.7(2) . . . . ? N4 C23 C19 C20 -177.66(16) . . . . ? C6 N2 C7 C12 -87.17(19) . . . . ? C6 N2 C7 C8 99.49(18) . . . . ? C10 C9 C8 C7 0.2(2) . . . . ? C10 C9 C8 C13 -178.31(16) . . . . ? C12 C7 C8 C9 -2.0(2) . . . . ? N2 C7 C8 C9 171.23(14) . . . . ? C12 C7 C8 C13 176.48(15) . . . . ? N2 C7 C8 C13 -10.3(2) . . . . ? N3 C19 C20 C21 -0.22(18) . . . . ? C23 C19 C20 C21 -179.00(16) . . . . ? C22 C21 C20 C19 0.24(19) . . . . ? C5 N1 C2 C3 -0.17(19) . . . . ? C5 N1 C2 C6 -179.06(15) . . . . ? C4 C3 C2 N1 0.29(19) . . . . ? C4 C3 C2 C6 179.10(16) . . . . ? N2 C6 C2 N1 -0.4(3) . . . . ? N2 C6 C2 C3 -179.00(17) . . . . ? C25 C24 C29 C28 -0.6(2) . . . . ? N4 C24 C29 C28 171.98(14) . . . . ? C25 C24 C29 C33 179.11(15) . . . . ? N4 C24 C29 C33 -8.3(2) . . . . ? C24 C29 C28 C27 -0.6(2) . . . . ? C33 C29 C28 C27 179.74(15) . . . . ? C19 N3 C22 C21 0.04(19) . . . . ? C20 C21 C22 N3 -0.17(19) . . . . ? C2 N1 C5 C4 0.0(2) . . . . ? C28 C29 C33 C34 -40.0(2) . . . . ? C24 C29 C33 C34 140.35(17) . . . . ? C28 C29 C33 C35 85.1(2) . . . . ? C24 C29 C33 C35 -94.64(19) . . . . ? N1 C5 C4 C3 0.2(2) . . . . ? C2 C3 C4 C5 -0.3(2) . . . . ? C26 C25 C30 C31 31.3(2) . . . . ? C24 C25 C30 C31 -150.49(15) . . . . ? C26 C25 C30 C32 -92.61(19) . . . . ? C24 C25 C30 C32 85.59(18) . . . . ? C10 C11 C12 C7 -0.8(2) . . . . ? C10 C11 C12 C16 -177.78(16) . . . . ? C8 C7 C12 C11 2.3(2) . . . . ? N2 C7 C12 C11 -170.82(14) . . . . ? C8 C7 C12 C16 179.24(14) . . . . ? N2 C7 C12 C16 6.1(2) . . . . ? C18 C16 C12 C11 79.9(2) . . . . ? C17 C16 C12 C11 -44.3(2) . . . . ? C18 C16 C12 C7 -97.0(2) . . . . ? C17 C16 C12 C7 138.81(17) . . . . ? C29 C28 C27 C26 1.5(2) . . . . ? C25 C26 C27 C28 -1.3(2) . . . . ? C8 C9 C10 C11 1.3(3) . . . . ? C12 C11 C10 C9 -1.0(3) . . . . ? C9 C8 C13 C14 93.4(2) . . . . ? C7 C8 C13 C14 -85.02(19) . . . . ? C9 C8 C13 C15 -29.3(2) . . . . ? C7 C8 C13 C15 152.28(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.75 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.416 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.044 ################################################################################ data_Compound_1 _database_code_depnum_ccdc_archive 'CCDC 727073' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 N4 Na2' _chemical_formula_sum 'C22 H18 N4 Na2' _chemical_formula_weight 384.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 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 10.1739(15) _cell_length_b 10.0052(14) _cell_length_c 19.371(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.439(9) _cell_angle_gamma 90.00 _cell_volume 1965.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4182 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 26.80 _exptl_crystal_description prism _exptl_crystal_colour beige _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9861 _exptl_absorpt_correction_T_max 0.9965 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 21021 _diffrn_reflns_av_R_equivalents 0.0859 _diffrn_reflns_av_sigmaI/netI 0.0787 _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 -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 26.80 _reflns_number_total 4182 _reflns_number_gt 2321 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP and MERCURY' _computing_publication_material enCIFer _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^)+(0.0551P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4182 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1179 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 Na1 Na 0.90989(8) 0.40173(8) 1.02521(5) 0.0278(2) Uani 1 1 d . . . Na2 Na 0.90481(9) 0.90138(9) 1.00257(6) 0.0435(3) Uani 1 1 d . . . N1 N 0.85293(19) 0.13434(17) 1.01095(10) 0.0259(5) Uani 1 1 d . . . N2 N 0.94184(19) 0.06795(18) 0.87896(9) 0.0283(5) Uani 1 1 d . . . N3 N 0.86888(19) 0.63713(17) 1.01084(10) 0.0256(5) Uani 1 1 d . . . N4 N 1.06517(18) 0.42099(18) 1.12692(9) 0.0263(5) Uani 1 1 d . . . C2 C 0.8029(2) 0.1917(2) 0.94956(12) 0.0241(5) Uani 1 1 d . . . C3 C 0.6973(2) 0.2762(2) 0.96059(12) 0.0289(6) Uani 1 1 d . . . H3 H 0.6480 0.3263 0.9274 0.035 Uiso 1 1 calc R . . C4 C 0.6809(2) 0.2706(2) 1.03064(12) 0.0310(6) Uani 1 1 d . . . H4 H 0.6181 0.3163 1.0539 0.037 Uiso 1 1 calc R . . C5 C 0.7760(2) 0.1835(2) 1.05954(12) 0.0289(6) Uani 1 1 d . . . H5 H 0.7860 0.1614 1.1063 0.035 Uiso 1 1 calc R . . C6 C 0.8535(2) 0.1589(2) 0.88498(12) 0.0247(5) Uani 1 1 d . . . H6 H 0.8214 0.2051 0.8455 0.030 Uiso 1 1 calc R . . C7 C 0.9823(2) 0.0452(2) 0.81129(12) 0.0264(5) Uani 1 1 d . . . C8 C 1.0102(2) 0.1484(2) 0.76653(12) 0.0283(6) Uani 1 1 d . . . H8 H 1.0052 0.2367 0.7811 0.034 Uiso 1 1 calc R . . C9 C 1.0453(2) 0.1205(2) 0.70080(12) 0.0326(6) Uani 1 1 d . . . H9 H 1.0646 0.1902 0.6714 0.039 Uiso 1 1 calc R . . C10 C 1.0521(2) -0.0100(2) 0.67813(12) 0.0335(6) Uani 1 1 d . . . H10 H 1.0735 -0.0283 0.6333 0.040 Uiso 1 1 calc R . . C11 C 1.0268(2) -0.1131(2) 0.72252(13) 0.0341(6) Uani 1 1 d . . . H11 H 1.0321 -0.2012 0.7077 0.041 Uiso 1 1 calc R . . C12 C 0.9937(2) -0.0857(2) 0.78898(12) 0.0296(6) Uani 1 1 d . . . H12 H 0.9790 -0.1557 0.8190 0.036 Uiso 1 1 calc R . . C13 C 0.7901(2) 0.6706(2) 0.95224(12) 0.0245(5) Uani 1 1 d . . . C14 C 0.6787(2) 0.7406(2) 0.97009(13) 0.0311(6) Uani 1 1 d . . . H14 H 0.6113 0.7743 0.9398 0.037 Uiso 1 1 calc R . . C15 C 0.6881(2) 0.7501(2) 1.04167(13) 0.0322(6) Uani 1 1 d . . . H15 H 0.6288 0.7914 1.0690 0.039 Uiso 1 1 calc R . . C16 C 0.8041(2) 0.6854(2) 1.06435(12) 0.0303(6) Uani 1 1 d . . . H16 H 0.8339 0.6761 1.1107 0.036 Uiso 1 1 calc R . . C17 C 1.1758(2) 0.3647(2) 1.11568(12) 0.0268(6) Uani 1 1 d . . . H17 H 1.2356 0.3464 1.1532 0.032 Uiso 1 1 calc R . . C18 C 1.0414(2) 0.4561(2) 1.19582(12) 0.0269(6) Uani 1 1 d . . . C19 C 0.9112(2) 0.4515(2) 1.21385(12) 0.0302(6) Uani 1 1 d . . . H19 H 0.8444 0.4273 1.1807 0.036 Uiso 1 1 calc R . . C20 C 0.8803(3) 0.4825(2) 1.28015(13) 0.0349(6) Uani 1 1 d . . . H20 H 0.7933 0.4785 1.2916 0.042 Uiso 1 1 calc R . . C21 C 0.9793(3) 0.5198(2) 1.32951(13) 0.0364(6) Uani 1 1 d . . . H21 H 0.9595 0.5389 1.3745 0.044 Uiso 1 1 calc R . . C22 C 1.1075(3) 0.5282(2) 1.31132(13) 0.0369(6) Uani 1 1 d . . . H22 H 1.1738 0.5550 1.3442 0.044 Uiso 1 1 calc R . . C23 C 1.1391(2) 0.4974(2) 1.24502(12) 0.0324(6) Uani 1 1 d . . . H23 H 1.2258 0.5044 1.2335 0.039 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 Na1 0.0209(5) 0.0266(5) 0.0359(6) 0.0001(4) 0.0029(4) -0.0014(4) Na2 0.0254(6) 0.0247(5) 0.0806(8) 0.0007(5) 0.0054(5) -0.0028(4) N1 0.0263(12) 0.0271(11) 0.0247(11) 0.0015(8) 0.0054(9) -0.0016(9) N2 0.0296(12) 0.0315(11) 0.0240(12) -0.0008(8) 0.0028(9) 0.0041(9) N3 0.0242(11) 0.0262(11) 0.0269(12) 0.0003(8) 0.0043(9) -0.0009(8) N4 0.0226(11) 0.0282(11) 0.0280(12) 0.0011(8) 0.0019(9) 0.0005(9) C2 0.0220(13) 0.0263(12) 0.0240(13) -0.0005(10) 0.0027(10) -0.0025(10) C3 0.0202(13) 0.0367(14) 0.0296(15) -0.0009(11) 0.0015(11) 0.0018(11) C4 0.0212(14) 0.0381(14) 0.0351(16) -0.0039(11) 0.0108(11) -0.0008(11) C5 0.0267(14) 0.0331(13) 0.0279(14) 0.0007(11) 0.0086(11) -0.0069(11) C6 0.0234(13) 0.0249(12) 0.0257(14) 0.0025(10) 0.0018(10) -0.0027(10) C7 0.0208(13) 0.0317(13) 0.0262(14) -0.0023(10) -0.0010(10) 0.0035(10) C8 0.0290(15) 0.0286(13) 0.0274(14) -0.0032(10) 0.0036(11) 0.0040(10) C9 0.0340(15) 0.0374(15) 0.0270(15) 0.0026(11) 0.0056(12) 0.0017(12) C10 0.0345(16) 0.0411(15) 0.0252(14) -0.0058(11) 0.0053(11) 0.0053(12) C11 0.0364(16) 0.0307(14) 0.0354(16) -0.0067(11) 0.0043(12) 0.0061(12) C12 0.0307(15) 0.0286(13) 0.0299(14) 0.0001(10) 0.0049(11) 0.0039(11) C13 0.0187(13) 0.0262(12) 0.0289(14) 0.0042(10) 0.0031(11) -0.0033(10) C14 0.0183(13) 0.0360(14) 0.0394(16) 0.0076(11) 0.0050(11) 0.0018(11) C15 0.0255(14) 0.0337(14) 0.0392(17) 0.0003(11) 0.0139(12) 0.0008(11) C16 0.0338(15) 0.0289(13) 0.0285(14) 0.0016(11) 0.0048(12) -0.0022(12) C17 0.0214(14) 0.0288(13) 0.0301(14) 0.0036(10) 0.0009(11) -0.0040(10) C18 0.0267(14) 0.0255(12) 0.0288(14) 0.0024(10) 0.0034(11) 0.0038(10) C19 0.0261(15) 0.0328(13) 0.0316(15) -0.0017(11) 0.0018(11) -0.0008(11) C20 0.0341(16) 0.0350(14) 0.0369(16) -0.0020(11) 0.0103(13) 0.0040(12) C21 0.0482(18) 0.0320(14) 0.0293(15) -0.0010(11) 0.0050(13) 0.0100(13) C22 0.0343(16) 0.0377(15) 0.0366(16) -0.0066(12) -0.0098(12) 0.0085(12) C23 0.0281(15) 0.0338(14) 0.0347(16) -0.0053(11) -0.0010(12) 0.0057(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 Na1 N3 2.4043(19) . ? Na1 N4 2.436(2) . ? Na1 N3 2.439(2) 3_767 ? Na1 C4 2.683(2) . ? Na1 C5 2.684(2) . ? Na1 C3 2.721(2) . ? Na1 C2 2.739(2) . ? Na1 N1 2.747(2) . ? Na1 Na1 2.9086(17) 3_767 ? Na1 C17 3.129(3) . ? Na1 Na2 3.6329(13) 3_767 ? Na2 N1 2.398(2) 1_565 ? Na2 N1 2.524(2) 3_767 ? Na2 N3 2.6756(19) . ? Na2 N2 2.691(2) 3_767 ? Na2 C16 2.710(2) . ? Na2 C13 2.733(2) . ? Na2 Na2 2.7722(19) 3_777 ? Na2 C15 2.825(2) . ? Na2 C14 2.838(3) . ? Na2 N2 2.965(2) 1_565 ? Na2 Na1 3.6329(13) 3_767 ? N1 C5 1.362(3) . ? N1 C2 1.382(3) . ? N1 Na2 2.398(2) 1_545 ? N1 Na2 2.524(2) 3_767 ? N2 C6 1.291(3) . ? N2 C7 1.423(3) . ? N2 Na2 2.691(2) 3_767 ? N2 Na2 2.965(2) 1_545 ? N3 C16 1.359(3) . ? N3 C13 1.379(3) . ? N3 Na1 2.439(2) 3_767 ? N4 C17 1.292(3) . ? N4 C18 1.419(3) . ? C2 C3 1.397(3) . ? C2 C6 1.427(3) . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.388(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.386(3) . ? C7 C8 1.392(3) . ? C8 C9 1.377(3) . ? C8 H8 0.9300 . ? C9 C10 1.382(3) . ? C9 H9 0.9300 . ? C10 C11 1.379(3) . ? C10 H10 0.9300 . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.399(3) . ? C13 C17 1.431(3) 3_767 ? C14 C15 1.386(3) . ? C14 H14 0.9300 . ? C15 C16 1.387(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C13 1.431(3) 3_767 ? C17 H17 0.9300 . ? C18 C23 1.385(3) . ? C18 C19 1.397(3) . ? C19 C20 1.381(3) . ? C19 H19 0.9300 . ? C20 C21 1.385(3) . ? C20 H20 0.9300 . ? C21 C22 1.380(4) . ? C21 H21 0.9300 . ? C22 C23 1.382(3) . ? C22 H22 0.9300 . ? C23 H23 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 N3 Na1 N4 96.43(7) . . ? N3 Na1 N3 106.18(6) . 3_767 ? N4 Na1 N3 71.89(7) . 3_767 ? N3 Na1 C4 109.89(8) . . ? N4 Na1 C4 121.19(7) . . ? N3 Na1 C4 139.17(7) 3_767 . ? N3 Na1 C5 137.62(8) . . ? N4 Na1 C5 100.01(7) . . ? N3 Na1 C5 116.00(7) 3_767 . ? C4 Na1 C5 29.97(7) . . ? N3 Na1 C3 105.91(8) . . ? N4 Na1 C3 148.36(8) . . ? N3 Na1 C3 120.87(7) 3_767 . ? C4 Na1 C3 29.60(7) . . ? C5 Na1 C3 48.55(7) . . ? N3 Na1 C2 129.16(7) . . ? N4 Na1 C2 134.39(7) . . ? N3 Na1 C2 93.54(7) 3_767 . ? C4 Na1 C2 48.35(7) . . ? C5 Na1 C2 47.17(7) . . ? C3 Na1 C2 29.65(7) . . ? N3 Na1 N1 155.38(7) . . ? N4 Na1 N1 106.08(7) . . ? N3 Na1 N1 90.46(6) 3_767 . ? C4 Na1 N1 49.50(7) . . ? C5 Na1 N1 29.01(6) . . ? C3 Na1 N1 49.47(6) . . ? C2 Na1 N1 29.17(6) . . ? N3 Na1 Na1 53.64(5) . 3_767 ? N4 Na1 Na1 80.32(6) . 3_767 ? N3 Na1 Na1 52.55(5) 3_767 3_767 ? C4 Na1 Na1 156.30(7) . 3_767 ? C5 Na1 Na1 168.03(7) . 3_767 ? C3 Na1 Na1 131.06(7) . 3_767 ? C2 Na1 Na1 125.01(7) . 3_767 ? N1 Na1 Na1 139.31(6) . 3_767 ? N3 Na1 C17 108.39(7) . . ? N4 Na1 C17 22.76(6) . . ? N3 Na1 C17 50.55(6) 3_767 . ? C4 Na1 C17 129.48(7) . . ? C5 Na1 C17 101.43(7) . . ? C3 Na1 C17 145.59(7) . . ? C2 Na1 C17 119.96(7) . . ? N1 Na1 C17 96.18(6) . . ? Na1 Na1 C17 74.22(5) 3_767 . ? N3 Na1 Na2 152.62(6) . 3_767 ? N4 Na1 Na2 82.78(5) . 3_767 ? N3 Na1 Na2 47.43(5) 3_767 3_767 ? C4 Na1 Na2 93.42(6) . 3_767 ? C5 Na1 Na2 68.70(6) . 3_767 ? C3 Na1 Na2 87.12(6) . 3_767 ? C2 Na1 Na2 57.96(5) . 3_767 ? N1 Na1 Na2 43.94(4) . 3_767 ? Na1 Na1 Na2 99.60(4) 3_767 3_767 ? C17 Na1 Na2 63.14(5) . 3_767 ? N1 Na2 N1 111.50(6) 1_565 3_767 ? N1 Na2 N3 157.60(8) 1_565 . ? N1 Na2 N3 90.31(6) 3_767 . ? N1 Na2 N2 86.99(7) 1_565 3_767 ? N1 Na2 N2 66.31(6) 3_767 3_767 ? N3 Na2 N2 97.73(7) . 3_767 ? N1 Na2 C16 130.73(8) 1_565 . ? N1 Na2 C16 109.79(7) 3_767 . ? N3 Na2 C16 29.23(6) . . ? N2 Na2 C16 85.90(7) 3_767 . ? N1 Na2 C13 139.06(8) 1_565 . ? N1 Na2 C13 103.69(7) 3_767 . ? N3 Na2 C13 29.52(6) . . ? N2 Na2 C13 127.15(7) 3_767 . ? C16 Na2 C13 47.00(7) . . ? N1 Na2 Na2 57.90(6) 1_565 3_777 ? N1 Na2 Na2 53.59(5) 3_767 3_777 ? N3 Na2 Na2 143.57(7) . 3_777 ? N2 Na2 Na2 65.72(6) 3_767 3_777 ? C16 Na2 Na2 150.78(9) . 3_777 ? C13 Na2 Na2 150.33(8) . 3_777 ? N1 Na2 C15 108.80(7) 1_565 . ? N1 Na2 C15 137.75(7) 3_767 . ? N3 Na2 C15 48.81(6) . . ? N2 Na2 C15 104.20(8) 3_767 . ? C16 Na2 C15 28.92(7) . . ? C13 Na2 C15 47.35(7) . . ? Na2 Na2 C15 162.32(8) 3_777 . ? N1 Na2 C14 112.77(8) 1_565 . ? N1 Na2 C14 132.70(7) 3_767 . ? N3 Na2 C14 48.77(6) . . ? N2 Na2 C14 131.33(7) 3_767 . ? C16 Na2 C14 46.99(7) . . ? C13 Na2 C14 29.01(6) . . ? Na2 Na2 C14 162.23(8) 3_777 . ? C15 Na2 C14 28.33(7) . . ? N1 Na2 N2 63.31(6) 1_565 1_565 ? N1 Na2 N2 79.03(6) 3_767 1_565 ? N3 Na2 N2 129.07(7) . 1_565 ? N2 Na2 N2 121.54(5) 3_767 1_565 ? C16 Na2 N2 151.75(8) . 1_565 ? C13 Na2 N2 105.33(7) . 1_565 ? Na2 Na2 N2 55.82(5) 3_777 1_565 ? C15 Na2 N2 131.93(7) . 1_565 ? C14 Na2 N2 106.92(7) . 1_565 ? N1 Na2 Na1 160.20(6) 1_565 3_767 ? N1 Na2 Na1 49.03(5) 3_767 3_767 ? N3 Na2 Na1 42.17(4) . 3_767 ? N2 Na2 Na1 87.03(5) 3_767 3_767 ? C16 Na2 Na1 67.54(6) . 3_767 ? C13 Na2 Na1 56.89(5) . 3_767 ? Na2 Na2 Na1 102.53(5) 3_777 3_767 ? C15 Na2 Na1 90.97(5) . 3_767 ? C14 Na2 Na1 85.12(5) . 3_767 ? N2 Na2 Na1 104.46(5) 1_565 3_767 ? C5 N1 C2 104.59(19) . . ? C5 N1 Na2 122.62(15) . 1_545 ? C2 N1 Na2 114.44(14) . 1_545 ? C5 N1 Na2 137.81(16) . 3_767 ? C2 N1 Na2 105.49(13) . 3_767 ? Na2 N1 Na2 68.50(6) 1_545 3_767 ? C5 N1 Na1 72.95(12) . . ? C2 N1 Na1 75.10(12) . . ? Na2 N1 Na1 155.18(9) 1_545 . ? Na2 N1 Na1 87.03(6) 3_767 . ? C6 N2 C7 116.71(19) . . ? C6 N2 Na2 101.80(15) . 3_767 ? C7 N2 Na2 127.88(15) . 3_767 ? C6 N2 Na2 100.99(14) . 1_545 ? C7 N2 Na2 135.89(14) . 1_545 ? Na2 N2 Na2 58.46(5) 3_767 1_545 ? C16 N3 C13 104.85(19) . . ? C16 N3 Na1 110.46(14) . . ? C13 N3 Na1 114.67(14) . . ? C16 N3 Na1 141.99(16) . 3_767 ? C13 N3 Na1 107.04(14) . 3_767 ? Na1 N3 Na1 73.82(6) . 3_767 ? C16 N3 Na2 76.79(12) . . ? C13 N3 Na2 77.55(12) . . ? Na1 N3 Na2 162.11(9) . . ? Na1 N3 Na2 90.40(6) 3_767 . ? C17 N4 C18 118.7(2) . . ? C17 N4 Na1 110.37(16) . . ? C18 N4 Na1 129.31(15) . . ? N1 C2 C3 110.9(2) . . ? N1 C2 C6 121.7(2) . . ? C3 C2 C6 127.4(2) . . ? N1 C2 Na1 75.73(12) . . ? C3 C2 Na1 74.46(13) . . ? C6 C2 Na1 119.33(15) . . ? C4 C3 C2 106.2(2) . . ? C4 C3 Na1 73.70(14) . . ? C2 C3 Na1 75.90(13) . . ? C4 C3 H3 126.9 . . ? C2 C3 H3 126.9 . . ? Na1 C3 H3 115.9 . . ? C3 C4 C5 106.8(2) . . ? C3 C4 Na1 76.70(13) . . ? C5 C4 Na1 75.05(13) . . ? C3 C4 H4 126.6 . . ? C5 C4 H4 126.6 . . ? Na1 C4 H4 114.1 . . ? N1 C5 C4 111.6(2) . . ? N1 C5 Na1 78.04(12) . . ? C4 C5 Na1 74.98(13) . . ? N1 C5 H5 124.2 . . ? C4 C5 H5 124.2 . . ? Na1 C5 H5 114.5 . . ? N2 C6 C2 122.8(2) . . ? N2 C6 H6 118.6 . . ? C2 C6 H6 118.6 . . ? C12 C7 C8 118.7(2) . . ? C12 C7 N2 118.4(2) . . ? C8 C7 N2 122.9(2) . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C8 C9 C10 120.5(2) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C11 C10 C9 119.5(2) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 120.2(2) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C7 120.6(2) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? N3 C13 C14 110.4(2) . . ? N3 C13 C17 122.0(2) . 3_767 ? C14 C13 C17 127.6(2) . 3_767 ? N3 C13 Na2 72.93(12) . . ? C14 C13 Na2 79.65(14) . . ? C17 C13 Na2 114.16(14) 3_767 . ? C15 C14 C13 106.7(2) . . ? C15 C14 Na2 75.35(14) . . ? C13 C14 Na2 71.34(13) . . ? C15 C14 H14 126.7 . . ? C13 C14 H14 126.7 . . ? Na2 C14 H14 118.7 . . ? C14 C15 C16 106.1(2) . . ? C14 C15 Na2 76.32(13) . . ? C16 C15 Na2 70.91(13) . . ? C14 C15 H15 127.0 . . ? C16 C15 H15 127.0 . . ? Na2 C15 H15 117.9 . . ? N3 C16 C15 112.0(2) . . ? N3 C16 Na2 73.98(12) . . ? C15 C16 Na2 80.17(14) . . ? N3 C16 H16 124.0 . . ? C15 C16 H16 124.0 . . ? Na2 C16 H16 113.5 . . ? N4 C17 C13 122.6(2) . 3_767 ? N4 C17 Na1 46.86(12) . . ? C13 C17 Na1 76.98(14) 3_767 . ? N4 C17 H17 118.7 . . ? C13 C17 H17 118.7 3_767 . ? Na1 C17 H17 161.2 . . ? C23 C18 C19 118.8(2) . . ? C23 C18 N4 123.8(2) . . ? C19 C18 N4 117.4(2) . . ? C20 C19 C18 120.9(2) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 119.8(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 119.4(2) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 121.0(2) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C22 C23 C18 120.0(2) . . ? C22 C23 H23 120.0 . . ? C18 C23 H23 120.0 . . ? 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 N3 Na1 N1 C5 -73.8(2) . . . . ? N4 Na1 N1 C5 81.55(15) . . . . ? N3 Na1 N1 C5 152.81(14) 3_767 . . . ? C4 Na1 N1 C5 -36.00(14) . . . . ? C3 Na1 N1 C5 -75.27(15) . . . . ? C2 Na1 N1 C5 -110.75(19) . . . . ? Na1 Na1 N1 C5 175.39(14) 3_767 . . . ? C17 Na1 N1 C5 102.47(14) . . . . ? Na2 Na1 N1 C5 142.36(16) 3_767 . . . ? N3 Na1 N1 C2 36.9(2) . . . . ? N4 Na1 N1 C2 -167.71(13) . . . . ? N3 Na1 N1 C2 -96.44(13) 3_767 . . . ? C4 Na1 N1 C2 74.74(14) . . . . ? C5 Na1 N1 C2 110.75(19) . . . . ? C3 Na1 N1 C2 35.48(12) . . . . ? Na1 Na1 N1 C2 -73.86(16) 3_767 . . . ? C17 Na1 N1 C2 -146.78(13) . . . . ? Na2 Na1 N1 C2 -106.89(13) 3_767 . . . ? N3 Na1 N1 Na2 153.33(18) . . . 1_545 ? N4 Na1 N1 Na2 -51.3(2) . . . 1_545 ? N3 Na1 N1 Na2 20.0(2) 3_767 . . 1_545 ? C4 Na1 N1 Na2 -168.9(2) . . . 1_545 ? C5 Na1 N1 Na2 -132.9(3) . . . 1_545 ? C3 Na1 N1 Na2 151.9(2) . . . 1_545 ? C2 Na1 N1 Na2 116.4(3) . . . 1_545 ? Na1 Na1 N1 Na2 42.5(3) 3_767 . . 1_545 ? C17 Na1 N1 Na2 -30.4(2) . . . 1_545 ? Na2 Na1 N1 Na2 9.50(18) 3_767 . . 1_545 ? N3 Na1 N1 Na2 143.83(15) . . . 3_767 ? N4 Na1 N1 Na2 -60.81(8) . . . 3_767 ? N3 Na1 N1 Na2 10.45(7) 3_767 . . 3_767 ? C4 Na1 N1 Na2 -178.36(11) . . . 3_767 ? C5 Na1 N1 Na2 -142.36(16) . . . 3_767 ? C3 Na1 N1 Na2 142.37(10) . . . 3_767 ? C2 Na1 N1 Na2 106.89(13) . . . 3_767 ? Na1 Na1 N1 Na2 33.03(11) 3_767 . . 3_767 ? C17 Na1 N1 Na2 -39.89(7) . . . 3_767 ? N4 Na1 N3 C16 -67.16(17) . . . . ? N3 Na1 N3 C16 -140.12(18) 3_767 . . . ? C4 Na1 N3 C16 59.35(17) . . . . ? C5 Na1 N3 C16 45.4(2) . . . . ? C3 Na1 N3 C16 90.22(16) . . . . ? C2 Na1 N3 C16 111.26(16) . . . . ? N1 Na1 N3 C16 89.1(2) . . . . ? Na1 Na1 N3 C16 -140.12(18) 3_767 . . . ? C17 Na1 N3 C16 -87.04(17) . . . . ? Na2 Na1 N3 C16 -153.87(14) 3_767 . . . ? N4 Na1 N3 C13 174.65(15) . . . . ? N3 Na1 N3 C13 101.69(16) 3_767 . . . ? C4 Na1 N3 C13 -58.85(17) . . . . ? C5 Na1 N3 C13 -72.83(19) . . . . ? C3 Na1 N3 C13 -27.98(17) . . . . ? C2 Na1 N3 C13 -6.93(19) . . . . ? N1 Na1 N3 C13 -29.1(3) . . . . ? Na1 Na1 N3 C13 101.69(16) 3_767 . . . ? C17 Na1 N3 C13 154.76(14) . . . . ? Na2 Na1 N3 C13 87.9(2) 3_767 . . . ? N4 Na1 N3 Na1 72.96(7) . . . 3_767 ? N3 Na1 N3 Na1 0.0 3_767 . . 3_767 ? C4 Na1 N3 Na1 -160.53(8) . . . 3_767 ? C5 Na1 N3 Na1 -174.52(11) . . . 3_767 ? C3 Na1 N3 Na1 -129.66(7) . . . 3_767 ? C2 Na1 N3 Na1 -108.62(9) . . . 3_767 ? N1 Na1 N3 Na1 -130.81(16) . . . 3_767 ? C17 Na1 N3 Na1 53.08(7) . . . 3_767 ? Na2 Na1 N3 Na1 -13.76(14) 3_767 . . 3_767 ? N4 Na1 N3 Na2 44.1(3) . . . . ? N3 Na1 N3 Na2 -28.9(3) 3_767 . . . ? C4 Na1 N3 Na2 170.6(3) . . . . ? C5 Na1 N3 Na2 156.6(2) . . . . ? C3 Na1 N3 Na2 -158.6(3) . . . . ? C2 Na1 N3 Na2 -137.5(3) . . . . ? N1 Na1 N3 Na2 -159.7(2) . . . . ? Na1 Na1 N3 Na2 -28.9(3) 3_767 . . . ? C17 Na1 N3 Na2 24.2(3) . . . . ? Na2 Na1 N3 Na2 -42.7(4) 3_767 . . . ? N1 Na2 N3 C16 -33.9(3) 1_565 . . . ? N1 Na2 N3 C16 133.15(15) 3_767 . . . ? N2 Na2 N3 C16 67.03(14) 3_767 . . . ? C13 Na2 N3 C16 -108.75(19) . . . . ? Na2 Na2 N3 C16 126.03(17) 3_777 . . . ? C15 Na2 N3 C16 -35.11(14) . . . . ? C14 Na2 N3 C16 -73.07(14) . . . . ? N2 Na2 N3 C16 -150.78(14) 1_565 . . . ? Na1 Na2 N3 C16 143.87(16) 3_767 . . . ? N1 Na2 N3 C13 74.8(2) 1_565 . . . ? N1 Na2 N3 C13 -118.09(13) 3_767 . . . ? N2 Na2 N3 C13 175.78(13) 3_767 . . . ? C16 Na2 N3 C13 108.75(19) . . . . ? Na2 Na2 N3 C13 -125.21(16) 3_777 . . . ? C15 Na2 N3 C13 73.64(14) . . . . ? C14 Na2 N3 C13 35.68(12) . . . . ? N2 Na2 N3 C13 -42.03(15) 1_565 . . . ? Na1 Na2 N3 C13 -107.38(14) 3_767 . . . ? N1 Na2 N3 Na1 -150.2(2) 1_565 . . . ? N1 Na2 N3 Na1 16.9(3) 3_767 . . . ? N2 Na2 N3 Na1 -49.2(3) 3_767 . . . ? C16 Na2 N3 Na1 -116.2(3) . . . . ? C13 Na2 N3 Na1 135.0(3) . . . . ? Na2 Na2 N3 Na1 9.8(4) 3_777 . . . ? C15 Na2 N3 Na1 -151.3(3) . . . . ? C14 Na2 N3 Na1 170.7(3) . . . . ? N2 Na2 N3 Na1 93.0(3) 1_565 . . . ? Na1 Na2 N3 Na1 27.7(3) 3_767 . . . ? N1 Na2 N3 Na1 -177.81(19) 1_565 . . 3_767 ? N1 Na2 N3 Na1 -10.72(7) 3_767 . . 3_767 ? N2 Na2 N3 Na1 -76.84(7) 3_767 . . 3_767 ? C16 Na2 N3 Na1 -143.87(16) . . . 3_767 ? C13 Na2 N3 Na1 107.38(13) . . . 3_767 ? Na2 Na2 N3 Na1 -17.84(15) 3_777 . . 3_767 ? C15 Na2 N3 Na1 -178.98(11) . . . 3_767 ? C14 Na2 N3 Na1 143.06(10) . . . 3_767 ? N2 Na2 N3 Na1 65.35(10) 1_565 . . 3_767 ? N3 Na1 N4 C17 -123.49(15) . . . . ? N3 Na1 N4 C17 -18.53(14) 3_767 . . . ? C4 Na1 N4 C17 118.58(16) . . . . ? C5 Na1 N4 C17 95.72(16) . . . . ? C3 Na1 N4 C17 101.36(19) . . . . ? C2 Na1 N4 C17 58.22(19) . . . . ? N1 Na1 N4 C17 66.57(16) . . . . ? Na1 Na1 N4 C17 -72.14(15) 3_767 . . . ? Na2 Na1 N4 C17 28.94(15) 3_767 . . . ? N3 Na1 N4 C18 71.38(18) . . . . ? N3 Na1 N4 C18 176.35(19) 3_767 . . . ? C4 Na1 N4 C18 -46.5(2) . . . . ? C5 Na1 N4 C18 -69.40(18) . . . . ? C3 Na1 N4 C18 -63.8(2) . . . . ? C2 Na1 N4 C18 -106.90(18) . . . . ? N1 Na1 N4 C18 -98.55(18) . . . . ? Na1 Na1 N4 C18 122.74(18) 3_767 . . . ? C17 Na1 N4 C18 -165.1(3) . . . . ? Na2 Na1 N4 C18 -136.18(17) 3_767 . . . ? C5 N1 C2 C3 0.6(2) . . . . ? Na2 N1 C2 C3 137.53(16) 1_545 . . . ? Na2 N1 C2 C3 -149.43(16) 3_767 . . . ? Na1 N1 C2 C3 -66.86(17) . . . . ? C5 N1 C2 C6 -176.6(2) . . . . ? Na2 N1 C2 C6 -39.7(3) 1_545 . . . ? Na2 N1 C2 C6 33.3(2) 3_767 . . . ? Na1 N1 C2 C6 115.9(2) . . . . ? C5 N1 C2 Na1 67.49(14) . . . . ? Na2 N1 C2 Na1 -155.61(11) 1_545 . . . ? Na2 N1 C2 Na1 -82.57(8) 3_767 . . . ? N3 Na1 C2 N1 -161.17(12) . . . . ? N4 Na1 C2 N1 16.64(17) . . . . ? N3 Na1 C2 N1 84.59(13) 3_767 . . . ? C4 Na1 C2 N1 -79.06(13) . . . . ? C5 Na1 C2 N1 -38.20(12) . . . . ? C3 Na1 C2 N1 -116.90(19) . . . . ? Na1 Na1 C2 N1 130.12(12) 3_767 . . . ? C17 Na1 C2 N1 38.95(14) . . . . ? Na2 Na1 C2 N1 51.55(11) 3_767 . . . ? N3 Na1 C2 C3 -44.27(17) . . . . ? N4 Na1 C2 C3 133.53(14) . . . . ? N3 Na1 C2 C3 -158.51(14) 3_767 . . . ? C4 Na1 C2 C3 37.84(13) . . . . ? C5 Na1 C2 C3 78.70(15) . . . . ? N1 Na1 C2 C3 116.90(19) . . . . ? Na1 Na1 C2 C3 -112.98(14) 3_767 . . . ? C17 Na1 C2 C3 155.85(13) . . . . ? Na2 Na1 C2 C3 168.45(15) 3_767 . . . ? N3 Na1 C2 C6 80.2(2) . . . . ? N4 Na1 C2 C6 -101.98(19) . . . . ? N3 Na1 C2 C6 -34.02(18) 3_767 . . . ? C4 Na1 C2 C6 162.3(2) . . . . ? C5 Na1 C2 C6 -156.8(2) . . . . ? C3 Na1 C2 C6 124.5(2) . . . . ? N1 Na1 C2 C6 -118.6(2) . . . . ? Na1 Na1 C2 C6 11.5(2) 3_767 . . . ? C17 Na1 C2 C6 -79.67(19) . . . . ? Na2 Na1 C2 C6 -67.06(17) 3_767 . . . ? N1 C2 C3 C4 -0.4(3) . . . . ? C6 C2 C3 C4 176.7(2) . . . . ? Na1 C2 C3 C4 -68.02(16) . . . . ? N1 C2 C3 Na1 67.67(16) . . . . ? C6 C2 C3 Na1 -115.3(2) . . . . ? N3 Na1 C3 C4 -102.37(14) . . . . ? N4 Na1 C3 C4 30.9(2) . . . . ? N3 Na1 C3 C4 137.09(14) 3_767 . . . ? C5 Na1 C3 C4 38.26(13) . . . . ? C2 Na1 C3 C4 111.9(2) . . . . ? N1 Na1 C3 C4 77.00(14) . . . . ? Na1 Na1 C3 C4 -157.67(13) 3_767 . . . ? C17 Na1 C3 C4 73.02(18) . . . . ? Na2 Na1 C3 C4 102.10(13) 3_767 . . . ? N3 Na1 C3 C2 145.75(13) . . . . ? N4 Na1 C3 C2 -81.03(19) . . . . ? N3 Na1 C3 C2 25.21(16) 3_767 . . . ? C4 Na1 C3 C2 -111.9(2) . . . . ? C5 Na1 C3 C2 -73.62(15) . . . . ? N1 Na1 C3 C2 -34.88(12) . . . . ? Na1 Na1 C3 C2 90.45(15) 3_767 . . . ? C17 Na1 C3 C2 -38.9(2) . . . . ? Na2 Na1 C3 C2 -9.78(13) 3_767 . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? Na1 C3 C4 C5 -69.64(16) . . . . ? C2 C3 C4 Na1 69.56(16) . . . . ? N3 Na1 C4 C3 87.33(14) . . . . ? N4 Na1 C4 C3 -161.67(13) . . . . ? N3 Na1 C4 C3 -63.35(18) 3_767 . . . ? C5 Na1 C4 C3 -111.7(2) . . . . ? C2 Na1 C4 C3 -37.90(13) . . . . ? N1 Na1 C4 C3 -76.91(14) . . . . ? Na1 Na1 C4 C3 45.4(2) 3_767 . . . ? C17 Na1 C4 C3 -135.55(13) . . . . ? Na2 Na1 C4 C3 -78.04(13) 3_767 . . . ? N3 Na1 C4 C5 -160.96(14) . . . . ? N4 Na1 C4 C5 -49.97(16) . . . . ? N3 Na1 C4 C5 48.35(19) 3_767 . . . ? C3 Na1 C4 C5 111.7(2) . . . . ? C2 Na1 C4 C5 73.80(15) . . . . ? N1 Na1 C4 C5 34.80(12) . . . . ? Na1 Na1 C4 C5 157.15(17) 3_767 . . . ? C17 Na1 C4 C5 -23.85(17) . . . . ? Na2 Na1 C4 C5 33.66(14) 3_767 . . . ? C2 N1 C5 C4 -0.7(3) . . . . ? Na2 N1 C5 C4 -133.07(17) 1_545 . . . ? Na2 N1 C5 C4 133.6(2) 3_767 . . . ? Na1 N1 C5 C4 68.36(17) . . . . ? C2 N1 C5 Na1 -69.04(14) . . . . ? Na2 N1 C5 Na1 158.57(14) 1_545 . . . ? Na2 N1 C5 Na1 65.23(19) 3_767 . . . ? C3 C4 C5 N1 0.5(3) . . . . ? Na1 C4 C5 N1 -70.31(17) . . . . ? C3 C4 C5 Na1 70.79(16) . . . . ? N3 Na1 C5 N1 143.59(14) . . . . ? N4 Na1 C5 N1 -105.18(14) . . . . ? N3 Na1 C5 N1 -30.56(16) 3_767 . . . ? C4 Na1 C5 N1 116.5(2) . . . . ? C3 Na1 C5 N1 78.76(14) . . . . ? C2 Na1 C5 N1 38.43(12) . . . . ? Na1 Na1 C5 N1 -14.6(4) 3_767 . . . ? C17 Na1 C5 N1 -82.05(14) . . . . ? Na2 Na1 C5 N1 -27.05(12) 3_767 . . . ? N3 Na1 C5 C4 27.07(19) . . . . ? N4 Na1 C5 C4 138.30(14) . . . . ? N3 Na1 C5 C4 -147.07(14) 3_767 . . . ? C3 Na1 C5 C4 -37.76(13) . . . . ? C2 Na1 C5 C4 -78.08(15) . . . . ? N1 Na1 C5 C4 -116.5(2) . . . . ? Na1 Na1 C5 C4 -131.2(4) 3_767 . . . ? C17 Na1 C5 C4 161.43(14) . . . . ? Na2 Na1 C5 C4 -143.57(15) 3_767 . . . ? C7 N2 C6 C2 179.5(2) . . . . ? Na2 N2 C6 C2 -36.7(2) 3_767 . . . ? Na2 N2 C6 C2 23.1(2) 1_545 . . . ? N1 C2 C6 N2 4.9(3) . . . . ? C3 C2 C6 N2 -171.8(2) . . . . ? Na1 C2 C6 N2 95.7(2) . . . . ? C6 N2 C7 C12 -135.0(2) . . . . ? Na2 N2 C7 C12 92.0(2) 3_767 . . . ? Na2 N2 C7 C12 10.6(3) 1_545 . . . ? C6 N2 C7 C8 44.6(3) . . . . ? Na2 N2 C7 C8 -88.3(2) 3_767 . . . ? Na2 N2 C7 C8 -169.71(17) 1_545 . . . ? C12 C7 C8 C9 1.6(3) . . . . ? N2 C7 C8 C9 -178.1(2) . . . . ? C7 C8 C9 C10 0.6(4) . . . . ? C8 C9 C10 C11 -1.7(4) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C7 1.6(4) . . . . ? C8 C7 C12 C11 -2.7(4) . . . . ? N2 C7 C12 C11 177.0(2) . . . . ? C16 N3 C13 C14 0.8(2) . . . . ? Na1 N3 C13 C14 122.16(17) . . . . ? Na1 N3 C13 C14 -158.21(15) 3_767 . . . ? Na2 N3 C13 C14 -71.66(17) . . . . ? C16 N3 C13 C17 -179.3(2) . . . 3_767 ? Na1 N3 C13 C17 -57.9(2) . . . 3_767 ? Na1 N3 C13 C17 21.7(2) 3_767 . . 3_767 ? Na2 N3 C13 C17 108.2(2) . . . 3_767 ? C16 N3 C13 Na2 72.50(14) . . . . ? Na1 N3 C13 Na2 -166.18(11) . . . . ? Na1 N3 C13 Na2 -86.55(8) 3_767 . . . ? N1 Na2 C13 N3 -145.87(14) 1_565 . . . ? N1 Na2 C13 N3 65.22(13) 3_767 . . . ? N2 Na2 C13 N3 -5.25(16) 3_767 . . . ? C16 Na2 C13 N3 -39.22(12) . . . . ? Na2 Na2 C13 N3 101.47(18) 3_777 . . . ? C15 Na2 C13 N3 -79.02(13) . . . . ? C14 Na2 C13 N3 -115.25(19) . . . . ? N2 Na2 C13 N3 147.39(12) 1_565 . . . ? Na1 Na2 C13 N3 49.89(11) 3_767 . . . ? N1 Na2 C13 C14 -30.61(19) 1_565 . . . ? N1 Na2 C13 C14 -179.52(14) 3_767 . . . ? N3 Na2 C13 C14 115.25(19) . . . . ? N2 Na2 C13 C14 110.00(15) 3_767 . . . ? C16 Na2 C13 C14 76.03(15) . . . . ? Na2 Na2 C13 C14 -143.28(17) 3_777 . . . ? C15 Na2 C13 C14 36.23(13) . . . . ? N2 Na2 C13 C14 -97.36(14) 1_565 . . . ? Na1 Na2 C13 C14 165.15(16) 3_767 . . . ? N1 Na2 C13 C17 96.06(19) 1_565 . . 3_767 ? N1 Na2 C13 C17 -52.85(18) 3_767 . . 3_767 ? N3 Na2 C13 C17 -118.1(2) . . . 3_767 ? N2 Na2 C13 C17 -123.32(17) 3_767 . . 3_767 ? C16 Na2 C13 C17 -157.3(2) . . . 3_767 ? Na2 Na2 C13 C17 -16.6(3) 3_777 . . 3_767 ? C15 Na2 C13 C17 162.9(2) . . . 3_767 ? C14 Na2 C13 C17 126.7(2) . . . 3_767 ? N2 Na2 C13 C17 29.32(18) 1_565 . . 3_767 ? Na1 Na2 C13 C17 -68.18(16) 3_767 . . 3_767 ? N3 C13 C14 C15 -0.4(3) . . . . ? C17 C13 C14 C15 179.7(2) 3_767 . . . ? Na2 C13 C14 C15 -67.69(16) . . . . ? N3 C13 C14 Na2 67.28(16) . . . . ? C17 C13 C14 Na2 -112.6(2) 3_767 . . . ? N1 Na2 C14 C15 -87.58(15) 1_565 . . . ? N1 Na2 C14 C15 114.27(15) 3_767 . . . ? N3 Na2 C14 C15 77.30(14) . . . . ? N2 Na2 C14 C15 19.48(17) 3_767 . . . ? C16 Na2 C14 C15 37.60(13) . . . . ? C13 Na2 C14 C15 113.6(2) . . . . ? Na2 Na2 C14 C15 -142.2(2) 3_777 . . . ? N2 Na2 C14 C15 -155.15(13) 1_565 . . . ? Na1 Na2 C14 C15 101.19(13) 3_767 . . . ? N1 Na2 C14 C13 158.78(14) 1_565 . . . ? N1 Na2 C14 C13 0.63(18) 3_767 . . . ? N3 Na2 C14 C13 -36.33(13) . . . . ? N2 Na2 C14 C13 -94.16(15) 3_767 . . . ? C16 Na2 C14 C13 -76.04(15) . . . . ? Na2 Na2 C14 C13 104.1(3) 3_777 . . . ? C15 Na2 C14 C13 -113.6(2) . . . . ? N2 Na2 C14 C13 91.21(14) 1_565 . . . ? Na1 Na2 C14 C13 -12.45(13) 3_767 . . . ? C13 C14 C15 C16 -0.2(3) . . . . ? Na2 C14 C15 C16 -65.15(16) . . . . ? C13 C14 C15 Na2 64.95(16) . . . . ? N1 Na2 C15 C14 103.31(14) 1_565 . . . ? N1 Na2 C15 C14 -94.77(16) 3_767 . . . ? N3 Na2 C15 C14 -77.16(14) . . . . ? N2 Na2 C15 C14 -165.03(13) 3_767 . . . ? C16 Na2 C15 C14 -112.7(2) . . . . ? C13 Na2 C15 C14 -37.16(13) . . . . ? Na2 Na2 C15 C14 142.0(3) 3_777 . . . ? N2 Na2 C15 C14 32.70(17) 1_565 . . . ? Na1 Na2 C15 C14 -77.84(13) 3_767 . . . ? N1 Na2 C15 C16 -144.02(15) 1_565 . . . ? N1 Na2 C15 C16 17.9(2) 3_767 . . . ? N3 Na2 C15 C16 35.51(13) . . . . ? N2 Na2 C15 C16 -52.36(15) 3_767 . . . ? C13 Na2 C15 C16 75.51(15) . . . . ? Na2 Na2 C15 C16 -105.3(3) 3_777 . . . ? C14 Na2 C15 C16 112.7(2) . . . . ? N2 Na2 C15 C16 145.38(14) 1_565 . . . ? Na1 Na2 C15 C16 34.83(14) 3_767 . . . ? C13 N3 C16 C15 -1.0(3) . . . . ? Na1 N3 C16 C15 -125.03(17) . . . . ? Na1 N3 C16 C15 145.3(2) 3_767 . . . ? Na2 N3 C16 C15 72.08(18) . . . . ? C13 N3 C16 Na2 -73.06(14) . . . . ? Na1 N3 C16 Na2 162.89(11) . . . . ? Na1 N3 C16 Na2 73.2(2) 3_767 . . . ? C14 C15 C16 N3 0.8(3) . . . . ? Na2 C15 C16 N3 -68.15(16) . . . . ? C14 C15 C16 Na2 68.90(16) . . . . ? N1 Na2 C16 N3 163.70(13) 1_565 . . . ? N1 Na2 C16 N3 -50.84(15) 3_767 . . . ? N2 Na2 C16 N3 -113.84(14) 3_767 . . . ? C13 Na2 C16 N3 39.64(12) . . . . ? Na2 Na2 C16 N3 -100.40(19) 3_777 . . . ? C15 Na2 C16 N3 116.5(2) . . . . ? C14 Na2 C16 N3 79.70(14) . . . . ? N2 Na2 C16 N3 53.2(2) 1_565 . . . ? Na1 Na2 C16 N3 -25.36(12) 3_767 . . . ? N1 Na2 C16 C15 47.22(19) 1_565 . . . ? N1 Na2 C16 C15 -167.31(14) 3_767 . . . ? N3 Na2 C16 C15 -116.5(2) . . . . ? N2 Na2 C16 C15 129.68(15) 3_767 . . . ? C13 Na2 C16 C15 -76.84(16) . . . . ? Na2 Na2 C16 C15 143.12(17) 3_777 . . . ? C14 Na2 C16 C15 -36.78(13) . . . . ? N2 Na2 C16 C15 -63.3(2) 1_565 . . . ? Na1 Na2 C16 C15 -141.84(16) 3_767 . . . ? C18 N4 C17 C13 -178.11(19) . . . 3_767 ? Na1 N4 C17 C13 15.0(3) . . . 3_767 ? C18 N4 C17 Na1 166.9(2) . . . . ? N3 Na1 C17 N4 60.85(16) . . . . ? N3 Na1 C17 N4 156.98(18) 3_767 . . . ? C4 Na1 C17 N4 -76.74(17) . . . . ? C5 Na1 C17 N4 -88.64(16) . . . . ? C3 Na1 C17 N4 -114.49(18) . . . . ? C2 Na1 C17 N4 -135.47(15) . . . . ? N1 Na1 C17 N4 -117.52(15) . . . . ? Na1 Na1 C17 N4 102.84(15) 3_767 . . . ? Na2 Na1 C17 N4 -147.44(16) 3_767 . . . ? N3 Na1 C17 C13 -106.24(13) . . . 3_767 ? N4 Na1 C17 C13 -167.1(2) . . . 3_767 ? N3 Na1 C17 C13 -10.11(11) 3_767 . . 3_767 ? C4 Na1 C17 C13 116.17(13) . . . 3_767 ? C5 Na1 C17 C13 104.28(13) . . . 3_767 ? C3 Na1 C17 C13 78.43(17) . . . 3_767 ? C2 Na1 C17 C13 57.44(14) . . . 3_767 ? N1 Na1 C17 C13 75.39(12) . . . 3_767 ? Na1 Na1 C17 C13 -64.25(12) 3_767 . . 3_767 ? Na2 Na1 C17 C13 45.47(11) 3_767 . . 3_767 ? C17 N4 C18 C23 33.4(3) . . . . ? Na1 N4 C18 C23 -162.56(17) . . . . ? C17 N4 C18 C19 -148.3(2) . . . . ? Na1 N4 C18 C19 15.8(3) . . . . ? C23 C18 C19 C20 -2.4(3) . . . . ? N4 C18 C19 C20 179.1(2) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C19 C20 C21 C22 1.4(4) . . . . ? C20 C21 C22 C23 -1.3(4) . . . . ? C21 C22 C23 C18 -0.6(4) . . . . ? C19 C18 C23 C22 2.5(3) . . . . ? N4 C18 C23 C22 -179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.80 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.253 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.057 ################################################################################ data_Compound_4 _database_code_depnum_ccdc_archive 'CCDC 727074' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C42 H62 N4 Na2 O2' _chemical_formula_sum 'C42 H62 N4 Na2 O2' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour 'pale pink' _diffrn_ambient_temperature 150(2) _chemical_formula_weight 700.94 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 11.704(6) _cell_length_b 10.390(4) _cell_length_c 17.231(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.563(16) _cell_angle_gamma 90.00 _cell_volume 2085.5(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3703 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 25.14 _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9631 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 27062 _diffrn_reflns_av_R_equivalents 0.1586 _diffrn_reflns_av_sigmaI/netI 0.1332 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.14 _reflns_number_total 3703 _reflns_number_gt 1758 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BRUKER SMART' _computing_cell_refinement 'BRUKER SMART' _computing_data_reduction 'BRUKER SAINT' _computing_structure_solution SIR2004 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP _computing_publication_material enCIFer _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^)+(0.0571P)^2^+0.8197P] 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 0.0090(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3703 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1655 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.9995(3) 0.7934(3) 0.89494(19) 0.0201(8) Uani 1 1 d . . . C5 C 1.1751(3) 0.8152(3) 0.9438(2) 0.0286(9) Uani 1 1 d . . . H5 H 1.2400 0.8421 0.9749 0.034 Uiso 1 1 calc R . . C8 C 0.6534(3) 0.9957(3) 0.87995(19) 0.0252(9) Uani 1 1 d . . . C6 C 0.8781(3) 0.8099(3) 0.8869(2) 0.0232(8) Uani 1 1 d . . . H6 H 0.8359 0.7687 0.8456 0.028 Uiso 1 1 calc R . . C3 C 1.0657(3) 0.7134(3) 0.8522(2) 0.0290(9) Uani 1 1 d . . . H3 H 1.0395 0.6612 0.8104 0.035 Uiso 1 1 calc R . . C12 C 0.6327(3) 0.7932(3) 0.9500(2) 0.0295(9) Uani 1 1 d . . . C4 C 1.1778(3) 0.7267(3) 0.8842(2) 0.0325(10) Uani 1 1 d . . . H4 H 1.2420 0.6848 0.8687 0.039 Uiso 1 1 calc R . . C13 C 0.7304(3) 1.0986(3) 0.85002(19) 0.0254(9) Uani 1 1 d . . . H13 H 0.8009 1.1012 0.8857 0.030 Uiso 1 1 calc R . . C7 C 0.7018(3) 0.8873(3) 0.91979(19) 0.0241(9) Uani 1 1 d . . . C9 C 0.5348(3) 1.0055(3) 0.8699(2) 0.0326(9) Uani 1 1 d . . . H9 H 0.5010 1.0762 0.8437 0.039 Uiso 1 1 calc R . . C11 C 0.5147(3) 0.8082(4) 0.9379(2) 0.0340(10) Uani 1 1 d . . . H11 H 0.4673 0.7466 0.9574 0.041 Uiso 1 1 calc R . . C15 C 0.7646(3) 1.0630(3) 0.7695(2) 0.0372(10) Uani 1 1 d . . . H15A H 0.8136 1.1288 0.7518 0.056 Uiso 1 1 calc R . . H15B H 0.6969 1.0556 0.7335 0.056 Uiso 1 1 calc R . . H15C H 0.8048 0.9824 0.7725 0.056 Uiso 1 1 calc R . . C10 C 0.4660(3) 0.9121(4) 0.8980(2) 0.0368(10) Uani 1 1 d . . . H10 H 0.3865 0.9194 0.8898 0.044 Uiso 1 1 calc R . . C20 C 0.8954(4) 0.8192(4) 1.2288(2) 0.0512(12) Uani 1 1 d . . . H20A H 0.9556 0.8173 1.2717 0.061 Uiso 1 1 calc R . . H20B H 0.8347 0.7613 1.2411 0.061 Uiso 1 1 calc R . . C21 C 0.9806(4) 0.6492(4) 1.1642(2) 0.0477(12) Uani 1 1 d . . . H21A H 0.9193 0.5926 1.1770 0.057 Uiso 1 1 calc R . . H21B H 1.0432 0.6423 1.2052 0.057 Uiso 1 1 calc R . . C22 C 1.0210(3) 0.6096(4) 1.0880(2) 0.0452(11) Uani 1 1 d . . . H22A H 1.0487 0.5226 1.0917 0.068 Uiso 1 1 calc R . . H22B H 1.0819 0.6657 1.0756 0.068 Uiso 1 1 calc R . . H22C H 0.9585 0.6152 1.0477 0.068 Uiso 1 1 calc R . . C14 C 0.6782(3) 1.2335(3) 0.8485(2) 0.0383(10) Uani 1 1 d . . . H14A H 0.7311 1.2937 0.8294 0.057 Uiso 1 1 calc R . . H14B H 0.6629 1.2576 0.9003 0.057 Uiso 1 1 calc R . . H14C H 0.6079 1.2340 0.8148 0.057 Uiso 1 1 calc R . . C16 C 0.6838(3) 0.6793(3) 0.9961(2) 0.0371(10) Uani 1 1 d . . . H16 H 0.7670 0.6930 1.0036 0.045 Uiso 1 1 calc R . . C18 C 0.6421(4) 0.6697(4) 1.0767(2) 0.0614(14) Uani 1 1 d . . . H18A H 0.6778 0.5974 1.1039 0.092 Uiso 1 1 calc R . . H18B H 0.5603 0.6587 1.0717 0.092 Uiso 1 1 calc R . . H18C H 0.6618 0.7471 1.1053 0.092 Uiso 1 1 calc R . . N2 N 0.8234(2) 0.8785(2) 0.93345(16) 0.0235(7) Uani 1 1 d . . . N1 N 1.0679(2) 0.8585(2) 0.95217(16) 0.0227(7) Uani 1 1 d . . . O1 O 0.9400(2) 0.7790(2) 1.15897(14) 0.0370(7) Uani 1 1 d . . . Na1 Na 0.94749(12) 0.91091(12) 1.05315(7) 0.0283(4) Uani 1 1 d . . . C17 C 0.6642(4) 0.5535(4) 0.9523(3) 0.0687(15) Uani 1 1 d . . . H17A H 0.6990 0.4845 0.9832 0.103 Uiso 1 1 calc R . . H17B H 0.6979 0.5583 0.9038 0.103 Uiso 1 1 calc R . . H17C H 0.5832 0.5381 0.9423 0.103 Uiso 1 1 calc R . . C19 C 0.8491(5) 0.9536(4) 1.2180(3) 0.0834(19) Uani 1 1 d . . . H19A H 0.8188 0.9814 1.2651 0.125 Uiso 1 1 calc R . . H19B H 0.7891 0.9547 1.1759 0.125 Uiso 1 1 calc R . . H19C H 0.9097 1.0105 1.2063 0.125 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 C2 0.022(2) 0.0146(18) 0.023(2) -0.0001(15) 0.0021(17) -0.0027(15) C5 0.023(2) 0.037(2) 0.027(2) -0.0004(18) 0.0047(17) 0.0014(18) C8 0.029(2) 0.026(2) 0.021(2) -0.0033(15) -0.0006(17) -0.0003(16) C6 0.029(2) 0.0180(18) 0.022(2) 0.0001(16) -0.0012(17) -0.0055(16) C3 0.035(3) 0.026(2) 0.027(2) -0.0015(17) 0.0033(19) 0.0005(18) C12 0.029(2) 0.030(2) 0.031(2) -0.0025(17) 0.0062(18) -0.0032(18) C4 0.032(3) 0.033(2) 0.034(2) 0.0034(18) 0.011(2) 0.0088(18) C13 0.029(2) 0.0220(19) 0.024(2) 0.0041(16) -0.0015(17) 0.0003(17) C7 0.024(2) 0.025(2) 0.023(2) -0.0066(16) 0.0044(17) 0.0009(16) C9 0.030(2) 0.036(2) 0.031(2) 0.0027(18) -0.0010(18) 0.0089(18) C11 0.028(2) 0.034(2) 0.040(2) 0.0026(19) 0.0088(19) -0.0072(18) C15 0.046(3) 0.033(2) 0.033(2) 0.0042(18) 0.004(2) 0.0003(19) C10 0.023(2) 0.049(3) 0.038(2) 0.001(2) 0.0023(19) 0.000(2) C20 0.073(3) 0.048(3) 0.035(3) 0.008(2) 0.019(2) 0.006(2) C21 0.063(3) 0.029(2) 0.054(3) 0.014(2) 0.017(2) 0.012(2) C22 0.050(3) 0.033(2) 0.054(3) 0.005(2) 0.009(2) 0.012(2) C14 0.045(3) 0.027(2) 0.042(3) 0.0029(18) 0.000(2) 0.0051(18) C16 0.030(2) 0.033(2) 0.049(3) 0.012(2) 0.010(2) -0.0032(18) C18 0.078(4) 0.059(3) 0.048(3) 0.014(2) 0.007(3) 0.011(3) N2 0.0231(19) 0.0210(16) 0.0269(17) 0.0004(13) 0.0045(14) -0.0012(13) N1 0.0241(18) 0.0204(15) 0.0246(17) 0.0011(13) 0.0070(14) -0.0017(13) O1 0.0545(19) 0.0322(15) 0.0260(15) 0.0073(12) 0.0129(13) 0.0064(13) Na1 0.0353(9) 0.0265(7) 0.0240(8) 0.0015(6) 0.0071(6) -0.0008(7) C17 0.116(5) 0.035(3) 0.056(3) 0.003(2) 0.017(3) 0.015(3) C19 0.153(6) 0.045(3) 0.061(3) 0.007(2) 0.061(4) 0.021(3) _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 C2 N1 1.385(4) . ? C2 C3 1.395(4) . ? C2 C6 1.424(5) . ? C2 Na1 3.101(4) . ? C5 N1 1.354(4) . ? C5 C4 1.381(5) . ? C5 H5 0.9300 . ? C8 C9 1.386(5) . ? C8 C7 1.409(5) . ? C8 C13 1.520(5) . ? C6 N2 1.290(4) . ? C6 Na1 3.086(4) . ? C6 H6 0.9300 . ? C3 C4 1.379(5) . ? C3 H3 0.9300 . ? C12 C11 1.386(5) . ? C12 C7 1.400(5) . ? C12 C16 1.516(5) . ? C4 H4 0.9300 . ? C13 C15 1.527(5) . ? C13 C14 1.528(4) . ? C13 H13 0.9800 . ? C7 N2 1.423(4) . ? C9 C10 1.379(5) . ? C9 H9 0.9300 . ? C11 C10 1.374(5) . ? C11 H11 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C10 H10 0.9300 . ? C20 O1 1.420(4) . ? C20 C19 1.503(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 O1 1.429(4) . ? C21 C22 1.496(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C16 C17 1.514(5) . ? C16 C18 1.519(5) . ? C16 H16 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N2 Na1 2.428(3) . ? N1 Na1 2.404(3) 3_777 ? N1 Na1 2.405(3) . ? O1 Na1 2.290(3) . ? Na1 N1 2.404(3) 3_777 ? Na1 Na1 2.955(3) 3_777 ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 N1 C2 C3 110.7(3) . . ? N1 C2 C6 120.9(3) . . ? C3 C2 C6 128.3(3) . . ? N1 C2 Na1 48.01(16) . . ? C3 C2 Na1 149.9(2) . . ? C6 C2 Na1 76.11(19) . . ? N1 C5 C4 112.9(3) . . ? N1 C5 H5 123.5 . . ? C4 C5 H5 123.5 . . ? C9 C8 C7 118.0(3) . . ? C9 C8 C13 121.7(3) . . ? C7 C8 C13 120.3(3) . . ? N2 C6 C2 123.8(3) . . ? N2 C6 Na1 48.37(17) . . ? C2 C6 Na1 77.28(19) . . ? N2 C6 H6 118.1 . . ? C2 C6 H6 118.1 . . ? Na1 C6 H6 159.9 . . ? C4 C3 C2 106.6(3) . . ? C4 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? C11 C12 C7 118.0(3) . . ? C11 C12 C16 120.2(3) . . ? C7 C12 C16 121.8(3) . . ? C3 C4 C5 105.9(3) . . ? C3 C4 H4 127.1 . . ? C5 C4 H4 127.1 . . ? C8 C13 C15 110.8(3) . . ? C8 C13 C14 113.7(3) . . ? C15 C13 C14 110.3(3) . . ? C8 C13 H13 107.3 . . ? C15 C13 H13 107.3 . . ? C14 C13 H13 107.3 . . ? C12 C7 C8 121.3(3) . . ? C12 C7 N2 119.9(3) . . ? C8 C7 N2 118.7(3) . . ? C10 C9 C8 121.1(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C10 C11 C12 121.5(3) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C11 C10 C9 120.1(4) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? O1 C20 C19 109.1(3) . . ? O1 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? O1 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? O1 C21 C22 109.6(3) . . ? O1 C21 H21A 109.7 . . ? C22 C21 H21A 109.7 . . ? O1 C21 H21B 109.7 . . ? C22 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C17 C16 C18 110.6(3) . . ? C17 C16 C12 112.3(3) . . ? C18 C16 C12 112.6(3) . . ? C17 C16 H16 107.0 . . ? C18 C16 H16 107.0 . . ? C12 C16 H16 107.0 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C6 N2 C7 118.8(3) . . ? C6 N2 Na1 108.2(2) . . ? C7 N2 Na1 129.6(2) . . ? C5 N1 C2 103.8(3) . . ? C5 N1 Na1 113.2(2) . 3_777 ? C2 N1 Na1 115.0(2) . 3_777 ? C5 N1 Na1 140.1(2) . . ? C2 N1 Na1 106.6(2) . . ? Na1 N1 Na1 75.82(9) 3_777 . ? C20 O1 C21 111.8(3) . . ? C20 O1 Na1 122.9(2) . . ? C21 O1 Na1 125.2(2) . . ? O1 Na1 N1 128.22(11) . 3_777 ? O1 Na1 N1 120.71(10) . . ? N1 Na1 N1 104.18(9) 3_777 . ? O1 Na1 N2 121.83(11) . . ? N1 Na1 N2 93.98(10) 3_777 . ? N1 Na1 N2 72.45(11) . . ? O1 Na1 Na1 156.80(11) . 3_777 ? N1 Na1 Na1 52.12(8) 3_777 3_777 ? N1 Na1 Na1 52.06(7) . 3_777 ? N2 Na1 Na1 79.10(9) . 3_777 ? O1 Na1 C6 120.59(10) . . ? N1 Na1 C6 106.96(10) 3_777 . ? N1 Na1 C6 51.03(10) . . ? N2 Na1 C6 23.39(9) . . ? Na1 Na1 C6 74.06(8) 3_777 . ? O1 Na1 C2 119.36(10) . . ? N1 Na1 C2 112.28(10) 3_777 . ? N1 Na1 C2 25.34(9) . . ? N2 Na1 C2 49.52(9) . . ? Na1 Na1 C2 64.70(8) 3_777 . ? C6 Na1 C2 26.61(9) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C20 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 N1 C2 C6 N2 -4.1(5) . . . . ? C3 C2 C6 N2 174.0(3) . . . . ? Na1 C2 C6 N2 13.9(3) . . . . ? N1 C2 C6 Na1 -18.0(3) . . . . ? C3 C2 C6 Na1 160.1(3) . . . . ? N1 C2 C3 C4 1.0(4) . . . . ? C6 C2 C3 C4 -177.2(3) . . . . ? Na1 C2 C3 C4 -38.3(6) . . . . ? C2 C3 C4 C5 -0.8(4) . . . . ? N1 C5 C4 C3 0.4(4) . . . . ? C9 C8 C13 C15 -94.7(4) . . . . ? C7 C8 C13 C15 85.9(4) . . . . ? C9 C8 C13 C14 30.1(5) . . . . ? C7 C8 C13 C14 -149.3(3) . . . . ? C11 C12 C7 C8 1.5(5) . . . . ? C16 C12 C7 C8 -177.2(3) . . . . ? C11 C12 C7 N2 177.5(3) . . . . ? C16 C12 C7 N2 -1.2(5) . . . . ? C9 C8 C7 C12 -1.4(5) . . . . ? C13 C8 C7 C12 178.0(3) . . . . ? C9 C8 C7 N2 -177.4(3) . . . . ? C13 C8 C7 N2 2.0(5) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? C13 C8 C9 C10 -179.4(3) . . . . ? C7 C12 C11 C10 -0.2(5) . . . . ? C16 C12 C11 C10 178.5(3) . . . . ? C12 C11 C10 C9 -1.1(6) . . . . ? C8 C9 C10 C11 1.2(6) . . . . ? C11 C12 C16 C17 70.3(5) . . . . ? C7 C12 C16 C17 -111.0(4) . . . . ? C11 C12 C16 C18 -55.4(5) . . . . ? C7 C12 C16 C18 123.3(4) . . . . ? C2 C6 N2 C7 -179.7(3) . . . . ? Na1 C6 N2 C7 -161.4(3) . . . . ? C2 C6 N2 Na1 -18.2(4) . . . . ? C12 C7 N2 C6 85.8(4) . . . . ? C8 C7 N2 C6 -98.1(4) . . . . ? C12 C7 N2 Na1 -71.0(4) . . . . ? C8 C7 N2 Na1 105.1(3) . . . . ? C4 C5 N1 C2 0.2(4) . . . . ? C4 C5 N1 Na1 -125.2(3) . . . 3_777 ? C4 C5 N1 Na1 139.2(3) . . . . ? C3 C2 N1 C5 -0.8(3) . . . . ? C6 C2 N1 C5 177.6(3) . . . . ? Na1 C2 N1 C5 153.9(3) . . . . ? C3 C2 N1 Na1 123.5(2) . . . 3_777 ? C6 C2 N1 Na1 -58.1(3) . . . 3_777 ? Na1 C2 N1 Na1 -81.80(18) . . . 3_777 ? C3 C2 N1 Na1 -154.7(2) . . . . ? C6 C2 N1 Na1 23.7(3) . . . . ? C19 C20 O1 C21 -177.2(4) . . . . ? C19 C20 O1 Na1 3.9(5) . . . . ? C22 C21 O1 C20 177.2(4) . . . . ? C22 C21 O1 Na1 -4.0(5) . . . . ? C20 O1 Na1 N1 17.1(3) . . . 3_777 ? C21 O1 Na1 N1 -161.6(3) . . . 3_777 ? C20 O1 Na1 N1 163.3(3) . . . . ? C21 O1 Na1 N1 -15.4(3) . . . . ? C20 O1 Na1 N2 -109.2(3) . . . . ? C21 O1 Na1 N2 72.0(3) . . . . ? C20 O1 Na1 Na1 98.7(4) . . . 3_777 ? C21 O1 Na1 Na1 -80.0(4) . . . 3_777 ? C20 O1 Na1 C6 -136.6(3) . . . . ? C21 O1 Na1 C6 44.7(3) . . . . ? C20 O1 Na1 C2 -167.4(3) . . . . ? C21 O1 Na1 C2 13.9(3) . . . . ? C5 N1 Na1 O1 -43.8(4) . . . . ? C2 N1 Na1 O1 94.5(2) . . . . ? Na1 N1 Na1 O1 -153.18(13) 3_777 . . . ? C5 N1 Na1 N1 109.4(4) . . . 3_777 ? C2 N1 Na1 N1 -112.3(2) . . . 3_777 ? Na1 N1 Na1 N1 0.0 3_777 . . 3_777 ? C5 N1 Na1 N2 -160.9(3) . . . . ? C2 N1 Na1 N2 -22.63(19) . . . . ? Na1 N1 Na1 N2 89.72(10) 3_777 . . . ? C5 N1 Na1 Na1 109.4(3) . . . 3_777 ? C2 N1 Na1 Na1 -112.3(2) . . . 3_777 ? C5 N1 Na1 C6 -150.1(4) . . . . ? C2 N1 Na1 C6 -11.83(17) . . . . ? Na1 N1 Na1 C6 100.52(12) 3_777 . . . ? C5 N1 Na1 C2 -138.3(4) . . . . ? Na1 N1 Na1 C2 112.3(2) 3_777 . . . ? C6 N2 Na1 O1 -94.2(2) . . . . ? C7 N2 Na1 O1 64.5(3) . . . . ? C6 N2 Na1 N1 125.2(2) . . . 3_777 ? C7 N2 Na1 N1 -76.1(3) . . . 3_777 ? C6 N2 Na1 N1 21.5(2) . . . . ? C7 N2 Na1 N1 -179.7(3) . . . . ? C6 N2 Na1 Na1 75.0(2) . . . 3_777 ? C7 N2 Na1 Na1 -126.3(3) . . . 3_777 ? C7 N2 Na1 C6 158.8(4) . . . . ? C6 N2 Na1 C2 9.02(19) . . . . ? C7 N2 Na1 C2 167.8(3) . . . . ? N2 C6 Na1 O1 100.2(2) . . . . ? C2 C6 Na1 O1 -95.26(19) . . . . ? N2 C6 Na1 N1 -58.5(2) . . . 3_777 ? C2 C6 Na1 N1 106.05(18) . . . 3_777 ? N2 C6 Na1 N1 -153.3(2) . . . . ? C2 C6 Na1 N1 11.29(16) . . . . ? C2 C6 Na1 N2 164.6(3) . . . . ? N2 C6 Na1 Na1 -99.5(2) . . . 3_777 ? C2 C6 Na1 Na1 65.04(17) . . . 3_777 ? N2 C6 Na1 C2 -164.6(3) . . . . ? N1 C2 Na1 O1 -100.4(2) . . . . ? C3 C2 Na1 O1 -47.5(5) . . . . ? C6 C2 Na1 O1 100.40(19) . . . . ? N1 C2 Na1 N1 75.7(2) . . . 3_777 ? C3 C2 Na1 N1 128.7(5) . . . 3_777 ? C6 C2 Na1 N1 -83.44(19) . . . 3_777 ? C3 C2 Na1 N1 52.9(5) . . . . ? C6 C2 Na1 N1 -159.2(3) . . . . ? N1 C2 Na1 N2 151.2(2) . . . . ? C3 C2 Na1 N2 -155.9(5) . . . . ? C6 C2 Na1 N2 -7.99(16) . . . . ? N1 C2 Na1 Na1 53.79(18) . . . 3_777 ? C3 C2 Na1 Na1 106.7(5) . . . 3_777 ? C6 C2 Na1 Na1 -105.37(18) . . . 3_777 ? N1 C2 Na1 C6 159.2(3) . . . . ? C3 C2 Na1 C6 -147.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.247 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.057 #END