Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Philip Gale' 'Salvatore Camiolo' 'El Drubi Vega,Ismael' 'Michael B. Hursthouse' 'Mark E. Light' _publ_contact_author_name 'Dr Philip Gale' _publ_contact_author_address ; School of Chemstry University of Southampton Southampton Hampshire SO17 1BJ UNITED KINGDOM ; _publ_contact_author_email PHILIP.GALE@SOTON.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; Anion complexation properties of 2,2?-bisamidodipyrrolylmethanes ; data_ie4 _database_code_CSD 207873 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H32 N4 O2' _chemical_formula_weight 468.59 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 11.011(3) _cell_length_b 17.487(3) _cell_length_c 13.771(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.628(16) _cell_angle_gamma 90.00 _cell_volume 2638.9(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.9851 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean '9.091 pixels mm^1^' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12855 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 23.25 _reflns_number_total 3783 _reflns_number_gt 2997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.0987P)^2^+2.0344P] 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 0.020(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3783 _refine_ls_number_parameters 328 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0809 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1831 _refine_ls_wR_factor_gt 0.1685 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.042 _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 C25A C -0.3836(8) -0.3083(6) 0.4333(7) 0.0488(18) Uani 0.50 1 d PD A 1 H25A H -0.3895 -0.2789 0.3716 0.059 Uiso 0.50 1 calc PR A 1 H25B H -0.3303 -0.3531 0.4266 0.059 Uiso 0.50 1 calc PR A 1 C29A C -0.5096(8) -0.3338(5) 0.4566(6) 0.0776(17) Uani 0.50 1 d PD A 1 H29A H -0.5021 -0.3635 0.5172 0.116 Uiso 0.50 1 calc PR A 1 H29B H -0.5470 -0.3655 0.4031 0.116 Uiso 0.50 1 calc PR A 1 H29C H -0.5607 -0.2887 0.4645 0.116 Uiso 0.50 1 calc PR A 1 C25B C -0.4384(8) -0.2999(6) 0.4570(7) 0.0488(18) Uani 0.50 1 d PD A 2 H25C H -0.4811 -0.3348 0.4989 0.059 Uiso 0.50 1 calc PR A 2 H25D H -0.4980 -0.2625 0.4267 0.059 Uiso 0.50 1 calc PR A 2 C29B C -0.3811(8) -0.3442(5) 0.3800(6) 0.0776(17) Uani 0.50 1 d PD A 2 H29D H -0.3432 -0.3086 0.3370 0.116 Uiso 0.50 1 calc PR A 2 H29E H -0.4439 -0.3741 0.3416 0.116 Uiso 0.50 1 calc PR A 2 H29F H -0.3188 -0.3787 0.4111 0.116 Uiso 0.50 1 calc PR A 2 C1 C -0.0226(3) -0.18371(18) 0.9500(2) 0.0520(9) Uani 1 1 d . . . H1 H -0.0835 -0.2221 0.9513 0.062 Uiso 1 1 calc R . . C2 C 0.0551(4) -0.1696(2) 1.0320(3) 0.0725(12) Uani 1 1 d . . . H2 H 0.0446 -0.1963 1.0907 0.087 Uiso 1 1 calc R . . C3 C 0.1452(6) -0.1188(3) 1.0300(3) 0.130(3) Uani 1 1 d . . . H3 H 0.1979 -0.1090 1.0874 0.156 Uiso 1 1 calc R . . C4 C 0.1621(5) -0.0804(3) 0.9445(3) 0.115(2) Uani 1 1 d . . . H04 H 0.2286 -0.0459 0.9427 0.138 Uiso 1 1 calc R . . C5 C 0.0828(4) -0.0920(2) 0.8620(3) 0.0823(14) Uani 1 1 d . . . H5 H 0.0937 -0.0655 0.8033 0.099 Uiso 1 1 calc R . . C6 C -0.0132(3) -0.14295(18) 0.8659(2) 0.0494(8) Uani 1 1 d . . . C7 C -0.1319(2) -0.22235(14) 0.74376(19) 0.0322(6) Uani 1 1 d . . . C8 C -0.2086(2) -0.22391(14) 0.65152(19) 0.0324(6) Uani 1 1 d . A . C9 C -0.2677(3) -0.28600(16) 0.6057(2) 0.0444(8) Uani 1 1 d . A . C10 C -0.3320(3) -0.25816(17) 0.5180(2) 0.0514(9) Uani 1 1 d D . . C11 C -0.3088(3) -0.18106(16) 0.51277(19) 0.0358(7) Uani 1 1 d . A . C12 C -0.3511(3) -0.12305(16) 0.4365(2) 0.0391(7) Uani 1 1 d . . . H12A H -0.4236 -0.0962 0.4570 0.047 Uiso 1 1 calc R A . H12B H -0.3764 -0.1500 0.3745 0.047 Uiso 1 1 calc R . . C13 C -0.2554(2) -0.06489(15) 0.41871(19) 0.0348(7) Uani 1 1 d . A . C14 C -0.2529(3) 0.01365(15) 0.43036(19) 0.0350(7) Uani 1 1 d . . . C15 C -0.1379(3) 0.03925(15) 0.40525(18) 0.0335(7) Uani 1 1 d . A . C16 C -0.0737(3) -0.02498(14) 0.37882(18) 0.0330(7) Uani 1 1 d . . . C17 C 0.0491(3) -0.03135(14) 0.34955(18) 0.0326(7) Uani 1 1 d . A . C18 C 0.2014(3) -0.12485(16) 0.2972(2) 0.0387(7) Uani 1 1 d . A . C19 C 0.2191(3) -0.20279(18) 0.2893(3) 0.0541(9) Uani 1 1 d . . . H19 H 0.1587 -0.2373 0.3075 0.065 Uiso 1 1 calc R . . C20 C 0.3236(3) -0.2306(2) 0.2552(3) 0.0663(10) Uani 1 1 d . . . H20 H 0.3343 -0.2843 0.2495 0.080 Uiso 1 1 calc R . . C21 C 0.4127(3) -0.1820(2) 0.2295(2) 0.0591(10) Uani 1 1 d . . . H21 H 0.4843 -0.2015 0.2051 0.071 Uiso 1 1 calc R . . C22 C 0.3971(3) -0.1045(2) 0.2394(2) 0.0508(8) Uani 1 1 d . . . H22 H 0.4591 -0.0706 0.2227 0.061 Uiso 1 1 calc R . . C23 C 0.2927(3) -0.07521(18) 0.2734(2) 0.0446(8) Uani 1 1 d . . . H23 H 0.2832 -0.0215 0.2803 0.053 Uiso 1 1 calc R . . C24 C -0.2650(4) -0.36776(18) 0.6392(3) 0.0709(12) Uani 1 1 d . . . H24A H -0.1823 -0.3882 0.6380 0.106 Uiso 1 1 calc R A . H24B H -0.3220 -0.3980 0.5956 0.106 Uiso 1 1 calc R . . H24C H -0.2889 -0.3704 0.7058 0.106 Uiso 1 1 calc R . . C26 C -0.3552(3) 0.06282(17) 0.4581(2) 0.0415(7) Uani 1 1 d . A . H26A H -0.3211 0.1098 0.4902 0.050 Uiso 1 1 calc R . . H26B H -0.4007 0.0350 0.5057 0.050 Uiso 1 1 calc R . . C27 C -0.0961(3) 0.12067(15) 0.4102(2) 0.0410(7) Uani 1 1 d . . . H27A H -0.0123 0.1231 0.4416 0.062 Uiso 1 1 calc R A . H27B H -0.1498 0.1506 0.4483 0.062 Uiso 1 1 calc R . . H27C H -0.0987 0.1417 0.3441 0.062 Uiso 1 1 calc R . . C28 C -0.4430(3) 0.0849(2) 0.3701(2) 0.0543(9) Uani 1 1 d . . . H28A H -0.3972 0.1078 0.3200 0.081 Uiso 1 1 calc R A . H28B H -0.5026 0.1219 0.3901 0.081 Uiso 1 1 calc R . . H28C H -0.4858 0.0391 0.3436 0.081 Uiso 1 1 calc R . . N1 N -0.0917(2) -0.15449(13) 0.77905(16) 0.0398(6) Uani 1 1 d . . . H1A H -0.1161 -0.1135 0.7455 0.048 Uiso 1 1 calc R . . N2 N -0.23639(19) -0.16061(12) 0.59417(15) 0.0318(6) Uani 1 1 d . . . H2A H -0.2110 -0.1138 0.6082 0.038 Uiso 1 1 calc R A . N3 N -0.1481(2) -0.08754(12) 0.38889(15) 0.0340(6) Uani 1 1 d . A . H3A H -0.1283 -0.1352 0.3775 0.041 Uiso 1 1 calc R . . N4 N 0.0890(2) -0.10210(13) 0.32882(17) 0.0394(6) Uani 1 1 d . . . H4 H 0.0370 -0.1394 0.3362 0.047 Uiso 1 1 calc R A . O1 O -0.10449(18) -0.28278(10) 0.78793(14) 0.0433(6) Uani 1 1 d . . . O2 O 0.11481(17) 0.02573(10) 0.34347(13) 0.0367(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C25A 0.058(6) 0.043(3) 0.043(4) 0.000(3) -0.007(4) -0.015(4) C29A 0.087(4) 0.085(4) 0.058(3) -0.014(3) -0.006(3) -0.041(4) C25B 0.058(6) 0.043(3) 0.043(4) 0.000(3) -0.007(4) -0.015(4) C29B 0.087(4) 0.085(4) 0.058(3) -0.014(3) -0.006(3) -0.041(4) C1 0.070(2) 0.0468(18) 0.0368(18) 0.0059(14) -0.0068(16) -0.0068(16) C2 0.095(3) 0.078(3) 0.039(2) 0.0175(18) -0.0167(19) -0.021(2) C3 0.164(5) 0.154(5) 0.056(3) 0.047(3) -0.061(3) -0.094(4) C4 0.130(4) 0.129(4) 0.076(3) 0.028(3) -0.040(3) -0.075(4) C5 0.104(3) 0.080(3) 0.055(2) 0.021(2) -0.026(2) -0.039(2) C6 0.062(2) 0.0443(18) 0.0383(17) 0.0090(14) -0.0147(15) -0.0166(15) C7 0.0343(15) 0.0270(15) 0.0353(15) 0.0051(12) 0.0029(12) 0.0010(11) C8 0.0361(15) 0.0293(14) 0.0318(15) 0.0022(12) 0.0026(12) -0.0003(11) C9 0.059(2) 0.0312(15) 0.0412(17) 0.0033(13) -0.0042(14) -0.0046(14) C10 0.070(2) 0.0379(17) 0.0416(18) 0.0033(14) -0.0163(16) -0.0144(15) C11 0.0371(16) 0.0360(16) 0.0331(15) 0.0008(12) -0.0032(12) -0.0041(12) C12 0.0430(17) 0.0368(16) 0.0354(16) 0.0043(12) -0.0063(13) -0.0037(13) C13 0.0402(17) 0.0365(16) 0.0255(14) 0.0028(12) -0.0083(12) -0.0015(12) C14 0.0430(17) 0.0347(15) 0.0257(14) 0.0030(12) -0.0054(12) -0.0002(12) C15 0.0434(17) 0.0305(14) 0.0250(14) 0.0005(11) -0.0051(12) -0.0011(12) C16 0.0435(17) 0.0280(14) 0.0257(14) 0.0008(11) -0.0050(12) -0.0032(12) C17 0.0444(17) 0.0287(15) 0.0228(14) 0.0012(11) -0.0070(12) -0.0009(12) C18 0.0416(17) 0.0380(16) 0.0345(15) -0.0061(12) -0.0068(13) 0.0033(13) C19 0.050(2) 0.0430(18) 0.068(2) -0.0064(16) -0.0024(17) 0.0041(15) C20 0.058(2) 0.051(2) 0.088(3) -0.014(2) -0.003(2) 0.0131(18) C21 0.049(2) 0.072(3) 0.054(2) -0.0145(18) -0.0083(16) 0.0143(18) C22 0.0422(18) 0.066(2) 0.0427(18) -0.0099(16) -0.0015(14) 0.0002(16) C23 0.0494(19) 0.0460(18) 0.0369(16) -0.0053(14) -0.0030(14) -0.0021(14) C24 0.113(3) 0.0333(18) 0.059(2) 0.0067(16) -0.030(2) -0.0171(19) C26 0.0442(17) 0.0388(16) 0.0411(16) 0.0011(13) 0.0017(13) 0.0019(13) C27 0.0488(18) 0.0319(15) 0.0419(17) -0.0005(13) 0.0020(13) 0.0001(13) C28 0.052(2) 0.060(2) 0.0501(19) 0.0141(16) 0.0028(15) 0.0129(16) N1 0.0516(15) 0.0305(13) 0.0343(13) 0.0067(10) -0.0109(11) -0.0029(11) N2 0.0350(13) 0.0261(12) 0.0332(13) 0.0006(10) -0.0023(10) -0.0006(9) N3 0.0402(14) 0.0268(12) 0.0337(13) 0.0011(10) -0.0028(10) 0.0003(10) N4 0.0433(14) 0.0297(13) 0.0450(14) -0.0024(11) 0.0035(11) -0.0038(10) O1 0.0512(13) 0.0319(11) 0.0449(12) 0.0094(9) -0.0052(9) 0.0040(9) O2 0.0450(12) 0.0280(10) 0.0357(11) 0.0023(8) -0.0040(9) -0.0051(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 C25A C29A 1.521(11) . ? C25A C10 1.523(11) . ? C25B C29B 1.501(12) . ? C25B C10 1.555(11) . ? C1 C2 1.370(5) . ? C1 C6 1.372(4) . ? C2 C3 1.334(6) . ? C3 C4 1.384(6) . ? C4 C5 1.378(6) . ? C5 C6 1.388(5) . ? C6 N1 1.419(4) . ? C7 O1 1.242(3) . ? C7 N1 1.341(3) . ? C7 C8 1.455(4) . ? C8 N2 1.377(3) . ? C8 C9 1.386(4) . ? C9 C10 1.424(4) . ? C9 C24 1.502(4) . ? C10 C11 1.375(4) . ? C11 N2 1.359(3) . ? C11 C12 1.501(4) . ? C12 C13 1.502(4) . ? C13 N3 1.348(4) . ? C13 C14 1.383(4) . ? C14 C15 1.417(4) . ? C14 C26 1.497(4) . ? C15 C16 1.394(4) . ? C15 C27 1.496(4) . ? C16 N3 1.382(3) . ? C16 C17 1.452(4) . ? C17 O2 1.241(3) . ? C17 N4 1.353(3) . ? C18 C19 1.383(4) . ? C18 C23 1.391(4) . ? C18 N4 1.410(4) . ? C19 C20 1.374(5) . ? C20 C21 1.371(5) . ? C21 C22 1.374(5) . ? C22 C23 1.381(4) . ? C26 C28 1.524(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C29A C25A C10 106.7(6) . . ? C29B C25B C10 106.1(6) . . ? C2 C1 C6 120.7(3) . . ? C3 C2 C1 120.5(3) . . ? C2 C3 C4 120.3(4) . . ? C5 C4 C3 120.1(4) . . ? C4 C5 C6 119.2(4) . . ? C1 C6 C5 119.1(3) . . ? C1 C6 N1 123.2(3) . . ? C5 C6 N1 117.6(3) . . ? O1 C7 N1 121.3(2) . . ? O1 C7 C8 120.3(2) . . ? N1 C7 C8 118.4(2) . . ? N2 C8 C9 107.5(2) . . ? N2 C8 C7 124.3(2) . . ? C9 C8 C7 128.2(2) . . ? C8 C9 C10 106.9(2) . . ? C8 C9 C24 127.7(3) . . ? C10 C9 C24 125.4(3) . . ? C11 C10 C9 107.5(2) . . ? C11 C10 C25A 125.5(4) . . ? C9 C10 C25A 124.7(5) . . ? C11 C10 C25B 124.5(5) . . ? C9 C10 C25B 125.7(4) . . ? C25A C10 C25B 27.3(3) . . ? N2 C11 C10 108.2(2) . . ? N2 C11 C12 121.1(2) . . ? C10 C11 C12 130.7(2) . . ? C11 C12 C13 113.4(2) . . ? N3 C13 C14 108.6(2) . . ? N3 C13 C12 120.1(2) . . ? C14 C13 C12 131.3(3) . . ? C13 C14 C15 107.1(2) . . ? C13 C14 C26 126.4(3) . . ? C15 C14 C26 126.4(2) . . ? C16 C15 C14 107.3(2) . . ? C16 C15 C27 128.1(3) . . ? C14 C15 C27 124.6(2) . . ? N3 C16 C15 106.9(2) . . ? N3 C16 C17 123.0(2) . . ? C15 C16 C17 130.1(2) . . ? O2 C17 N4 121.2(3) . . ? O2 C17 C16 121.5(2) . . ? N4 C17 C16 117.3(2) . . ? C19 C18 C23 119.1(3) . . ? C19 C18 N4 115.9(3) . . ? C23 C18 N4 125.0(3) . . ? C20 C19 C18 120.3(3) . . ? C21 C20 C19 120.9(3) . . ? C20 C21 C22 119.1(3) . . ? C21 C22 C23 121.1(3) . . ? C22 C23 C18 119.5(3) . . ? C14 C26 C28 112.2(2) . . ? C7 N1 C6 125.7(2) . . ? C11 N2 C8 110.0(2) . . ? C13 N3 C16 110.1(2) . . ? C17 N4 C18 129.5(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2 0.88 1.96 2.810(3) 160.5 3_556 N2 H2A O2 0.88 1.95 2.805(3) 163.8 3_556 N3 H3A O1 0.88 1.93 2.727(3) 150.6 4 N4 H4 O1 0.88 2.13 2.945(3) 154.6 4 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.839 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.055 #===END data_ie24 _database_code_CSD 207874 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H40 N4 O2' _chemical_formula_weight 428.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.7164(2) _cell_length_b 14.1868(2) _cell_length_c 15.2266(2) _cell_angle_alpha 77.2000(10) _cell_angle_beta 75.5160(10) _cell_angle_gamma 76.1900(10) _cell_volume 2544.22(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.119 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type Multi-scans _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker Nonius FR591 Rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Nonius Kappa CCD Area detector' _diffrn_measurement_method '\f and \w scans to fill the asymmetric unit' _diffrn_detector_area_resol_mean '9.091 pixels mm^1^' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48899 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.03 _reflns_number_total 8967 _reflns_number_gt 7734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO (Otwinowski and MInor, 1997)' _computing_data_reduction 'DENZO, COLLECT, MAXUS (Mackay et al., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, et al., 1993)' _computing_publication_material 'WINGX (Farrugia, 1998)' _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^)+(0.1782P)^2^+5.6926P] 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 0.024(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8967 _refine_ls_number_parameters 572 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1422 _refine_ls_goodness_of_fit_ref 0.542 _refine_ls_restrained_S_all 0.542 _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 N1 N 0.34797(13) 0.42612(11) 0.45769(10) 0.0241(3) Uani 1 1 d . . . H1 H 0.3337 0.3822 0.5076 0.029 Uiso 1 1 calc R . . N2 N 0.34610(12) 0.46236(10) 0.63672(9) 0.0205(3) Uani 1 1 d . . . H2 H 0.3426 0.4006 0.6390 0.025 Uiso 1 1 calc R . . N3 N 0.52767(12) 0.40196(10) 0.79479(9) 0.0217(3) Uani 1 1 d . . . H3 H 0.5433 0.4083 0.7344 0.026 Uiso 1 1 calc R . . N4 N 0.76097(12) 0.33914(11) 0.72606(10) 0.0265(3) Uani 1 1 d . . . H4 H 0.7220 0.3813 0.6888 0.032 Uiso 1 1 calc R . . O1 O 0.38537(10) 0.57785(8) 0.39647(8) 0.0224(3) Uani 1 1 d . . . O2 O 0.78041(11) 0.27944(10) 0.87217(9) 0.0320(3) Uani 1 1 d . . . C1 C 0.3743(3) 0.15948(17) 0.28437(18) 0.0554(7) Uani 1 1 d . . . H1A H 0.4485 0.1296 0.2960 0.083 Uiso 1 1 calc R . . H1B H 0.3692 0.1476 0.2247 0.083 Uiso 1 1 calc R . . H1C H 0.3190 0.1301 0.3331 0.083 Uiso 1 1 calc R . . C2 C 0.35302(18) 0.26918(15) 0.28331(13) 0.0342(4) Uani 1 1 d . . . H2A H 0.2800 0.2995 0.2675 0.041 Uiso 1 1 calc R . . H2B H 0.4101 0.2981 0.2348 0.041 Uiso 1 1 calc R . . C3 C 0.35456(16) 0.29415(14) 0.37537(13) 0.0291(4) Uani 1 1 d . . . H3A H 0.2902 0.2748 0.4220 0.035 Uiso 1 1 calc R . . H3B H 0.4226 0.2559 0.3961 0.035 Uiso 1 1 calc R . . C4 C 0.35072(17) 0.40273(14) 0.36846(12) 0.0285(4) Uani 1 1 d . . . H4A H 0.4167 0.4217 0.3237 0.034 Uiso 1 1 calc R . . H4B H 0.2841 0.4413 0.3456 0.034 Uiso 1 1 calc R . . C5 C 0.36645(13) 0.51240(12) 0.46579(11) 0.0202(4) Uani 1 1 d . . . C6 C 0.36093(13) 0.53165(12) 0.55723(11) 0.0197(3) Uani 1 1 d . . . C7 C 0.36323(14) 0.61933(12) 0.58240(11) 0.0213(4) Uani 1 1 d . . . C8 C 0.34838(14) 0.60198(13) 0.67969(12) 0.0231(4) Uani 1 1 d . . . C9 C 0.33784(14) 0.50449(13) 0.71093(11) 0.0215(4) Uani 1 1 d . . . C10 C 0.32242(15) 0.44706(14) 0.80712(11) 0.0253(4) Uani 1 1 d . . . H10A H 0.2983 0.3857 0.8072 0.030 Uiso 1 1 calc R . . H10B H 0.2624 0.4862 0.8473 0.030 Uiso 1 1 calc R . . C11 C 0.42453(15) 0.42045(12) 0.84744(11) 0.0224(4) Uani 1 1 d . . . C12 C 0.43334(16) 0.40336(13) 0.93891(12) 0.0257(4) Uani 1 1 d . . . C13 C 0.54706(16) 0.37263(13) 0.94111(12) 0.0249(4) Uani 1 1 d . . . C14 C 0.60527(15) 0.37153(12) 0.85060(12) 0.0228(4) Uani 1 1 d . . . C15 C 0.72095(15) 0.32889(12) 0.81723(12) 0.0241(4) Uani 1 1 d . . . C16 C 0.86764(15) 0.28214(14) 0.68705(13) 0.0307(4) Uani 1 1 d . . . H16A H 0.8656 0.2110 0.7041 0.037 Uiso 1 1 calc R . . H16B H 0.9265 0.2943 0.7127 0.037 Uiso 1 1 calc R . . C17 C 0.89399(16) 0.31059(15) 0.58302(13) 0.0326(4) Uani 1 1 d . . . H17A H 0.9020 0.3804 0.5664 0.039 Uiso 1 1 calc R . . H17B H 0.8314 0.3045 0.5583 0.039 Uiso 1 1 calc R . . C18 C 0.99967(18) 0.24672(17) 0.53836(16) 0.0414(5) Uani 1 1 d . . . H18A H 1.0617 0.2508 0.5649 0.050 Uiso 1 1 calc R . . H18B H 0.9905 0.1772 0.5530 0.050 Uiso 1 1 calc R . . C19 C 1.0288(2) 0.2773(2) 0.43469(18) 0.0634(8) Uani 1 1 d . . . H19A H 0.9663 0.2764 0.4082 0.095 Uiso 1 1 calc R . . H19B H 1.0941 0.2312 0.4091 0.095 Uiso 1 1 calc R . . H19C H 1.0448 0.3439 0.4197 0.095 Uiso 1 1 calc R . . C20 C 0.37882(16) 0.71496(13) 0.51984(12) 0.0269(4) Uani 1 1 d . . . H20A H 0.4501 0.7051 0.4763 0.040 Uiso 1 1 calc R . . H20B H 0.3777 0.7640 0.5565 0.040 Uiso 1 1 calc R . . H20C H 0.3189 0.7382 0.4858 0.040 Uiso 1 1 calc R . . C21 C 0.33975(17) 0.67526(14) 0.74026(13) 0.0297(4) Uani 1 1 d . . . H21A H 0.3902 0.7214 0.7082 0.036 Uiso 1 1 calc R . . H21B H 0.3646 0.6398 0.7975 0.036 Uiso 1 1 calc R . . C22 C 0.22261(19) 0.73428(17) 0.76553(16) 0.0425(5) Uani 1 1 d . . . H22A H 0.1974 0.7698 0.7092 0.064 Uiso 1 1 calc R . . H22B H 0.2224 0.7816 0.8037 0.064 Uiso 1 1 calc R . . H22C H 0.1728 0.6894 0.7998 0.064 Uiso 1 1 calc R . . C23 C 0.33835(17) 0.40438(16) 1.02033(12) 0.0346(5) Uani 1 1 d . . . H23A H 0.2732 0.4527 1.0033 0.042 Uiso 1 1 calc R . . H23B H 0.3585 0.4250 1.0710 0.042 Uiso 1 1 calc R . . C24 C 0.30889(19) 0.30208(19) 1.05303(15) 0.0450(6) Uani 1 1 d . . . H24A H 0.2857 0.2831 1.0038 0.068 Uiso 1 1 calc R . . H24B H 0.2483 0.3035 1.1074 0.068 Uiso 1 1 calc R . . H24C H 0.3738 0.2542 1.0688 0.068 Uiso 1 1 calc R . . C25 C 0.59346(17) 0.34579(15) 1.02722(12) 0.0325(4) Uani 1 1 d . . . H25A H 0.5911 0.2767 1.0543 0.049 Uiso 1 1 calc R . . H25B H 0.5492 0.3880 1.0716 0.049 Uiso 1 1 calc R . . H25C H 0.6703 0.3552 1.0118 0.049 Uiso 1 1 calc R . . N5 N 1.30267(14) 0.12537(11) 0.71146(11) 0.0313(4) Uani 1 1 d . . . H5 H 1.2722 0.0964 0.7661 0.038 Uiso 1 1 calc R . . N6 N 1.15593(12) 0.24069(11) 0.84590(10) 0.0237(3) Uani 1 1 d . . . H6 H 1.1910 0.1862 0.8749 0.028 Uiso 1 1 calc R . . N7 N 0.89465(12) 0.17531(11) 1.00849(9) 0.0223(3) Uani 1 1 d . . . H7 H 0.8561 0.2146 0.9693 0.027 Uiso 1 1 calc R . . N8 N 0.71861(13) 0.09311(11) 0.98887(10) 0.0269(3) Uani 1 1 d . . . H8 H 0.7384 0.1450 0.9501 0.032 Uiso 1 1 calc R . . O3 O 1.31144(12) 0.26912(9) 0.61170(9) 0.0321(3) Uani 1 1 d . . . O4 O 0.75760(11) -0.03384(9) 1.10139(8) 0.0286(3) Uani 1 1 d . . . C26 C 1.2062(3) -0.0171(2) 0.5209(2) 0.0740(9) Uani 1 1 d . . . H26A H 1.2636 -0.0599 0.4835 0.111 Uiso 1 1 calc R . . H26B H 1.1539 0.0235 0.4835 0.111 Uiso 1 1 calc R . . H26C H 1.1667 -0.0576 0.5737 0.111 Uiso 1 1 calc R . . C27 C 1.2611(3) 0.05117(19) 0.55603(19) 0.0654(8) Uani 1 1 d . . . H27A H 1.3017 0.0911 0.5022 0.078 Uiso 1 1 calc R . . H27B H 1.2022 0.0971 0.5902 0.078 Uiso 1 1 calc R . . C28 C 1.3388(2) -0.00346(18) 0.61654(19) 0.0528(6) Uani 1 1 d . . . H28A H 1.3999 -0.0473 0.5818 0.063 Uiso 1 1 calc R . . H28B H 1.2994 -0.0452 0.6695 0.063 Uiso 1 1 calc R . . C29 C 1.38649(18) 0.06495(15) 0.65168(15) 0.0389(5) Uani 1 1 d . . . H29A H 1.4435 0.0255 0.6861 0.047 Uiso 1 1 calc R . . H29B H 1.4232 0.1085 0.5986 0.047 Uiso 1 1 calc R . . C30 C 1.26955(15) 0.22301(13) 0.68731(12) 0.0245(4) Uani 1 1 d . . . C31 C 1.18110(15) 0.27498(12) 0.75200(12) 0.0229(4) Uani 1 1 d . . . C32 C 1.10754(15) 0.36286(13) 0.73333(12) 0.0235(4) Uani 1 1 d . . . C33 C 1.03597(15) 0.38062(13) 0.81843(12) 0.0250(4) Uani 1 1 d . . . C34 C 1.06837(14) 0.30442(13) 0.88635(12) 0.0234(4) Uani 1 1 d . . . C35 C 1.02420(15) 0.28869(13) 0.98865(12) 0.0266(4) Uani 1 1 d . . . H35A H 1.0832 0.2916 1.0193 0.032 Uiso 1 1 calc R . . H35B H 0.9621 0.3440 1.0030 0.032 Uiso 1 1 calc R . . C36 C 0.98429(14) 0.19391(13) 1.02957(11) 0.0237(4) Uani 1 1 d . . . C37 C 1.02261(15) 0.11545(13) 1.09353(12) 0.0247(4) Uani 1 1 d . . . C38 C 0.95189(15) 0.04640(13) 1.11195(11) 0.0243(4) Uani 1 1 d . . . C39 C 0.87285(14) 0.08497(12) 1.05805(11) 0.0223(4) Uani 1 1 d . . . C40 C 0.78065(15) 0.04449(12) 1.05093(11) 0.0232(4) Uani 1 1 d . . . C41 C 0.61908(16) 0.06124(15) 0.98473(14) 0.0318(4) Uani 1 1 d . . . H41A H 0.5631 0.0697 1.0422 0.038 Uiso 1 1 calc R . . H41B H 0.6376 -0.0097 0.9805 0.038 Uiso 1 1 calc R . . C42 C 0.57020(16) 0.11932(14) 0.90272(14) 0.0313(4) Uani 1 1 d . . . H42A H 0.4965 0.1037 0.9091 0.038 Uiso 1 1 calc R . . H42B H 0.5593 0.1905 0.9039 0.038 Uiso 1 1 calc R . . C43 C 0.64084(18) 0.09874(15) 0.81017(14) 0.0356(5) Uani 1 1 d . . . H43A H 0.6535 0.0273 0.8092 0.043 Uiso 1 1 calc R . . H43B H 0.7138 0.1163 0.8026 0.043 Uiso 1 1 calc R . . C44 C 0.5881(2) 0.15593(18) 0.72944(17) 0.0518(6) Uani 1 1 d . . . H44A H 0.5128 0.1441 0.7396 0.078 Uiso 1 1 calc R . . H44B H 0.6323 0.1339 0.6724 0.078 Uiso 1 1 calc R . . H44C H 0.5853 0.2265 0.7245 0.078 Uiso 1 1 calc R . . C45 C 1.09752(16) 0.42674(14) 0.64138(13) 0.0295(4) Uani 1 1 d . . . H45A H 1.1341 0.4826 0.6325 0.044 Uiso 1 1 calc R . . H45B H 1.0191 0.4512 0.6395 0.044 Uiso 1 1 calc R . . H45C H 1.1328 0.3879 0.5923 0.044 Uiso 1 1 calc R . . C46 C 0.94485(16) 0.46923(15) 0.83059(15) 0.0343(4) Uani 1 1 d . . . H46A H 0.8928 0.4551 0.8900 0.041 Uiso 1 1 calc R . . H46B H 0.9033 0.4825 0.7807 0.041 Uiso 1 1 calc R . . C47 C 0.9894(2) 0.56023(17) 0.8290(2) 0.0548(7) Uani 1 1 d . . . H47A H 1.0231 0.5502 0.8824 0.082 Uiso 1 1 calc R . . H47B H 0.9285 0.6176 0.8311 0.082 Uiso 1 1 calc R . . H47C H 1.0452 0.5716 0.7723 0.082 Uiso 1 1 calc R . . C48 C 1.11869(16) 0.10539(15) 1.13772(14) 0.0331(4) Uani 1 1 d . . . H48A H 1.1677 0.1503 1.0992 0.040 Uiso 1 1 calc R . . H48B H 1.1618 0.0372 1.1395 0.040 Uiso 1 1 calc R . . C49 C 1.0843(2) 0.12848(19) 1.23522(15) 0.0454(6) Uani 1 1 d . . . H49A H 1.0460 0.1973 1.2336 0.068 Uiso 1 1 calc R . . H49B H 1.1503 0.1178 1.2611 0.068 Uiso 1 1 calc R . . H49C H 1.0346 0.0852 1.2736 0.068 Uiso 1 1 calc R . . C50 C 0.96567(18) -0.05012(14) 1.17659(14) 0.0338(4) Uani 1 1 d . . . H50A H 0.9129 -0.0442 1.2352 0.051 Uiso 1 1 calc R . . H50B H 1.0413 -0.0679 1.1874 0.051 Uiso 1 1 calc R . . H50C H 0.9518 -0.1013 1.1495 0.051 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0350(8) 0.0236(8) 0.0139(7) -0.0008(6) -0.0056(6) -0.0077(6) N2 0.0248(7) 0.0194(7) 0.0163(7) -0.0009(5) -0.0059(6) -0.0026(6) N3 0.0284(8) 0.0223(7) 0.0138(7) 0.0012(5) -0.0077(6) -0.0041(6) N4 0.0267(8) 0.0269(8) 0.0229(8) 0.0036(6) -0.0110(6) -0.0006(6) O1 0.0277(6) 0.0220(6) 0.0158(6) 0.0004(5) -0.0066(5) -0.0029(5) O2 0.0301(7) 0.0369(8) 0.0278(7) 0.0099(6) -0.0165(6) -0.0075(6) C1 0.091(2) 0.0349(12) 0.0493(14) -0.0141(11) -0.0347(14) -0.0016(12) C2 0.0450(12) 0.0333(11) 0.0272(10) -0.0074(8) -0.0118(8) -0.0067(9) C3 0.0358(10) 0.0289(10) 0.0247(9) -0.0048(7) -0.0107(8) -0.0056(8) C4 0.0411(11) 0.0280(9) 0.0183(9) -0.0040(7) -0.0084(7) -0.0081(8) C5 0.0193(8) 0.0226(8) 0.0169(8) -0.0022(7) -0.0054(6) -0.0001(6) C6 0.0204(8) 0.0211(8) 0.0156(8) 0.0004(6) -0.0067(6) -0.0005(6) C7 0.0220(8) 0.0217(8) 0.0191(8) -0.0023(7) -0.0075(7) 0.0004(7) C8 0.0238(9) 0.0253(9) 0.0204(8) -0.0052(7) -0.0088(7) 0.0006(7) C9 0.0204(8) 0.0267(9) 0.0159(8) -0.0037(7) -0.0061(6) 0.0008(7) C10 0.0270(9) 0.0312(10) 0.0160(8) -0.0004(7) -0.0063(7) -0.0040(7) C11 0.0295(9) 0.0200(8) 0.0173(8) -0.0011(6) -0.0074(7) -0.0035(7) C12 0.0348(10) 0.0240(9) 0.0174(8) -0.0018(7) -0.0085(7) -0.0023(7) C13 0.0366(10) 0.0206(8) 0.0199(8) -0.0013(7) -0.0129(7) -0.0048(7) C14 0.0302(9) 0.0199(8) 0.0203(8) 0.0012(6) -0.0129(7) -0.0050(7) C15 0.0288(9) 0.0213(8) 0.0244(9) 0.0038(7) -0.0120(7) -0.0091(7) C16 0.0242(9) 0.0303(10) 0.0342(10) 0.0022(8) -0.0103(8) -0.0017(7) C17 0.0276(10) 0.0360(11) 0.0324(10) -0.0063(8) -0.0089(8) 0.0002(8) C18 0.0339(11) 0.0407(12) 0.0465(13) -0.0124(10) -0.0069(9) 0.0020(9) C19 0.0517(15) 0.080(2) 0.0472(15) -0.0229(14) 0.0022(12) 0.0064(13) C20 0.0364(10) 0.0207(9) 0.0248(9) -0.0021(7) -0.0115(8) -0.0037(7) C21 0.0390(11) 0.0306(10) 0.0223(9) -0.0086(8) -0.0100(8) -0.0046(8) C22 0.0445(12) 0.0392(12) 0.0437(12) -0.0224(10) 0.0006(10) -0.0042(10) C23 0.0387(11) 0.0452(12) 0.0162(9) -0.0064(8) -0.0076(8) 0.0019(9) C24 0.0407(12) 0.0669(15) 0.0272(10) -0.0047(10) -0.0005(9) -0.0201(11) C25 0.0428(11) 0.0353(10) 0.0209(9) -0.0033(8) -0.0155(8) -0.0023(8) N5 0.0416(9) 0.0199(8) 0.0248(8) -0.0004(6) 0.0001(7) -0.0021(7) N6 0.0290(8) 0.0190(7) 0.0203(7) 0.0010(6) -0.0060(6) -0.0025(6) N7 0.0260(8) 0.0224(7) 0.0173(7) 0.0006(6) -0.0081(6) -0.0021(6) N8 0.0306(8) 0.0230(8) 0.0265(8) 0.0057(6) -0.0102(6) -0.0089(6) O3 0.0437(8) 0.0235(7) 0.0229(7) 0.0002(5) -0.0005(6) -0.0059(6) O4 0.0363(7) 0.0207(6) 0.0249(7) 0.0040(5) -0.0060(5) -0.0054(5) C26 0.096(2) 0.0523(16) 0.083(2) -0.0213(15) -0.0466(19) 0.0068(15) C27 0.105(2) 0.0372(13) 0.0491(15) -0.0125(11) -0.0215(15) 0.0061(14) C28 0.0627(16) 0.0369(12) 0.0538(14) -0.0149(11) -0.0081(12) 0.0025(11) C29 0.0427(12) 0.0271(10) 0.0393(11) -0.0093(9) 0.0010(9) 0.0009(9) C30 0.0308(9) 0.0202(8) 0.0212(9) -0.0010(7) -0.0058(7) -0.0044(7) C31 0.0289(9) 0.0204(8) 0.0195(8) 0.0003(7) -0.0073(7) -0.0059(7) C32 0.0274(9) 0.0204(8) 0.0242(9) -0.0005(7) -0.0097(7) -0.0056(7) C33 0.0245(9) 0.0239(9) 0.0276(9) -0.0041(7) -0.0080(7) -0.0042(7) C34 0.0250(9) 0.0221(9) 0.0239(9) -0.0043(7) -0.0054(7) -0.0054(7) C35 0.0308(10) 0.0277(9) 0.0230(9) -0.0064(7) -0.0046(7) -0.0084(7) C36 0.0255(9) 0.0274(9) 0.0177(8) -0.0061(7) -0.0040(7) -0.0027(7) C37 0.0248(9) 0.0271(9) 0.0206(8) -0.0065(7) -0.0052(7) 0.0009(7) C38 0.0289(9) 0.0229(9) 0.0175(8) -0.0036(7) -0.0048(7) 0.0022(7) C39 0.0268(9) 0.0190(8) 0.0183(8) -0.0023(6) -0.0043(7) -0.0002(7) C40 0.0277(9) 0.0206(8) 0.0179(8) -0.0030(7) -0.0034(7) -0.0001(7) C41 0.0311(10) 0.0309(10) 0.0345(10) 0.0025(8) -0.0087(8) -0.0136(8) C42 0.0288(10) 0.0275(10) 0.0411(11) 0.0003(8) -0.0154(8) -0.0092(8) C43 0.0433(12) 0.0295(10) 0.0378(11) -0.0013(8) -0.0202(9) -0.0064(9) C44 0.0755(18) 0.0417(13) 0.0470(14) -0.0025(11) -0.0357(13) -0.0089(12) C45 0.0332(10) 0.0275(9) 0.0272(10) 0.0017(8) -0.0123(8) -0.0043(8) C46 0.0286(10) 0.0313(10) 0.0385(11) -0.0065(8) -0.0076(8) 0.0039(8) C47 0.0567(15) 0.0297(12) 0.0751(18) -0.0208(12) -0.0093(13) 0.0031(10) C48 0.0296(10) 0.0359(11) 0.0333(10) -0.0045(8) -0.0132(8) 0.0004(8) C49 0.0476(13) 0.0578(14) 0.0371(12) -0.0124(10) -0.0222(10) -0.0042(11) C50 0.0413(11) 0.0256(10) 0.0330(10) 0.0022(8) -0.0173(9) -0.0005(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 1.337(2) . ? N1 C4 1.459(2) . ? N2 C9 1.362(2) . ? N2 C6 1.384(2) . ? N3 C11 1.355(2) . ? N3 C14 1.391(2) . ? N4 C15 1.342(2) . ? N4 C16 1.460(2) . ? O1 C5 1.257(2) . ? O2 C15 1.252(2) . ? C1 C2 1.512(3) . ? C2 C3 1.526(3) . ? C3 C4 1.510(3) . ? C5 C6 1.459(2) . ? C6 C7 1.389(2) . ? C7 C8 1.418(2) . ? C7 C20 1.500(2) . ? C8 C9 1.386(3) . ? C8 C21 1.504(2) . ? C9 C10 1.500(2) . ? C10 C11 1.506(2) . ? C11 C12 1.388(2) . ? C12 C13 1.414(3) . ? C12 C23 1.499(3) . ? C13 C14 1.393(3) . ? C13 C25 1.507(2) . ? C14 C15 1.458(3) . ? C16 C17 1.517(3) . ? C17 C18 1.524(3) . ? C18 C19 1.516(3) . ? C21 C22 1.526(3) . ? C23 C24 1.530(3) . ? N5 C30 1.343(2) . ? N5 C29 1.457(2) . ? N6 C34 1.364(2) . ? N6 C31 1.386(2) . ? N7 C36 1.355(2) . ? N7 C39 1.388(2) . ? N8 C40 1.347(2) . ? N8 C41 1.462(2) . ? O3 C30 1.250(2) . ? O4 C40 1.255(2) . ? C26 C27 1.566(4) . ? C27 C28 1.483(4) . ? C28 C29 1.506(3) . ? C30 C31 1.466(2) . ? C31 C32 1.389(2) . ? C32 C33 1.420(3) . ? C32 C45 1.507(2) . ? C33 C34 1.383(3) . ? C33 C46 1.502(3) . ? C34 C35 1.503(2) . ? C35 C36 1.500(2) . ? C36 C37 1.387(3) . ? C37 C38 1.421(3) . ? C37 C48 1.500(3) . ? C38 C39 1.391(2) . ? C38 C50 1.500(2) . ? C39 C40 1.459(3) . ? C41 C42 1.521(3) . ? C42 C43 1.517(3) . ? C43 C44 1.526(3) . ? C46 C47 1.522(3) . ? C48 C49 1.525(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 N1 C4 121.89(14) . . ? C9 N2 C6 109.43(14) . . ? C11 N3 C14 109.77(14) . . ? C15 N4 C16 121.69(15) . . ? C1 C2 C3 112.82(17) . . ? C4 C3 C2 111.72(15) . . ? N1 C4 C3 111.11(14) . . ? O1 C5 N1 121.17(15) . . ? O1 C5 C6 119.68(15) . . ? N1 C5 C6 119.12(15) . . ? N2 C6 C7 107.76(14) . . ? N2 C6 C5 123.62(15) . . ? C7 C6 C5 128.54(15) . . ? C6 C7 C8 107.07(15) . . ? C6 C7 C20 127.27(15) . . ? C8 C7 C20 125.66(16) . . ? C9 C8 C7 107.43(15) . . ? C9 C8 C21 125.07(16) . . ? C7 C8 C21 127.45(16) . . ? N2 C9 C8 108.30(14) . . ? N2 C9 C10 121.81(16) . . ? C8 C9 C10 129.88(16) . . ? C9 C10 C11 114.29(15) . . ? N3 C11 C12 108.37(15) . . ? N3 C11 C10 122.06(15) . . ? C12 C11 C10 129.41(16) . . ? C11 C12 C13 107.42(16) . . ? C11 C12 C23 125.57(17) . . ? C13 C12 C23 126.55(16) . . ? C14 C13 C12 107.40(15) . . ? C14 C13 C25 127.66(17) . . ? C12 C13 C25 124.94(17) . . ? N3 C14 C13 107.04(15) . . ? N3 C14 C15 123.14(15) . . ? C13 C14 C15 128.75(16) . . ? O2 C15 N4 120.44(17) . . ? O2 C15 C14 120.81(16) . . ? N4 C15 C14 118.66(15) . . ? N4 C16 C17 110.58(15) . . ? C16 C17 C18 112.54(16) . . ? C19 C18 C17 112.80(19) . . ? C8 C21 C22 113.15(16) . . ? C12 C23 C24 110.48(17) . . ? C30 N5 C29 123.29(16) . . ? C34 N6 C31 109.47(14) . . ? C36 N7 C39 109.65(14) . . ? C40 N8 C41 121.18(15) . . ? C28 C27 C26 113.6(2) . . ? C27 C28 C29 111.9(2) . . ? N5 C29 C28 112.58(19) . . ? O3 C30 N5 121.65(16) . . ? O3 C30 C31 120.22(16) . . ? N5 C30 C31 118.12(15) . . ? N6 C31 C32 107.73(15) . . ? N6 C31 C30 123.79(15) . . ? C32 C31 C30 128.47(16) . . ? C31 C32 C33 106.91(15) . . ? C31 C32 C45 128.39(16) . . ? C33 C32 C45 124.61(16) . . ? C34 C33 C32 107.72(16) . . ? C34 C33 C46 127.29(17) . . ? C32 C33 C46 124.95(17) . . ? N6 C34 C33 108.15(15) . . ? N6 C34 C35 121.87(16) . . ? C33 C34 C35 129.94(16) . . ? C36 C35 C34 115.83(14) . . ? N7 C36 C37 108.52(16) . . ? N7 C36 C35 121.22(15) . . ? C37 C36 C35 130.21(17) . . ? C36 C37 C38 107.26(16) . . ? C36 C37 C48 126.97(17) . . ? C38 C37 C48 125.75(17) . . ? C39 C38 C37 107.11(15) . . ? C39 C38 C50 128.44(17) . . ? C37 C38 C50 124.43(17) . . ? N7 C39 C38 107.46(15) . . ? N7 C39 C40 122.81(15) . . ? C38 C39 C40 129.73(16) . . ? O4 C40 N8 119.49(16) . . ? O4 C40 C39 121.66(16) . . ? N8 C40 C39 118.85(15) . . ? N8 C41 C42 111.92(15) . . ? C43 C42 C41 114.12(17) . . ? C42 C43 C44 112.87(19) . . ? C33 C46 C47 111.95(17) . . ? C37 C48 C49 113.46(17) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.88 2.01 2.8828(19) 172.8 1_455 N2 H2 O3 0.88 2.14 2.996(2) 163.5 1_455 N3 H3 O1 0.88 1.96 2.8207(18) 165.8 2_666 N4 H4 O1 0.88 2.02 2.8370(19) 155.0 2_666 N5 H5 O4 0.88 2.00 2.852(2) 163.9 2_757 N6 H6 O4 0.88 2.08 2.8848(19) 151.5 2_757 N7 H7 O2 0.88 1.91 2.7796(18) 169.3 . N8 H8 O2 0.88 2.12 2.996(2) 172.4 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.792 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.061