# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 #TrackingRef 'GLOBAL.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H39 Al2 N5 S' _chemical_formula_weight 507.64 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.3950(7) _cell_length_b 12.4760(9) _cell_length_c 22.1510(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.283(2) _cell_angle_gamma 90.00 _cell_volume 2795.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5194 _cell_measurement_theta_min 2.412 _cell_measurement_theta_max 26.098 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9272 _exptl_absorpt_correction_T_max 0.9475 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24954 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.43 _reflns_number_total 5730 _reflns_number_gt 4386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0716P)^2^+0.8374P] 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 5730 _refine_ls_number_parameters 315 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1166 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.036 _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 C1 C 0.3709(2) 0.47356(19) 0.33469(10) 0.0273(5) Uani 1 1 d . B . C2 C 0.4269(2) 0.52831(19) 0.29267(11) 0.0294(5) Uani 1 1 d . . . H2 H 0.4358 0.6038 0.2899 0.035 Uiso 1 1 calc R . . C3 C 0.4672(2) 0.45251(17) 0.25558(10) 0.0232(5) Uani 1 1 d . . . C4 C 0.3128(3) 0.5170(2) 0.38538(11) 0.0373(6) Uani 1 1 d . . . H4A H 0.2530 0.4637 0.3965 0.056 Uiso 1 1 calc R . . H4B H 0.2635 0.5827 0.3711 0.056 Uiso 1 1 calc R . . H4C H 0.3838 0.5330 0.4217 0.056 Uiso 1 1 calc R . . C5 C 0.5350(2) 0.46437(18) 0.20391(11) 0.0275(5) Uani 1 1 d . . . H5A H 0.6053 0.4107 0.2082 0.041 Uiso 1 1 calc R . . H5B H 0.5733 0.5363 0.2051 0.041 Uiso 1 1 calc R . . H5C H 0.4710 0.4539 0.1643 0.041 Uiso 1 1 calc R . . C6 C 0.3975(2) 0.24871(16) 0.08440(9) 0.0230(5) Uani 1 1 d . . . C7 C 0.2816(2) 0.30085(18) 0.08793(10) 0.0268(5) Uani 1 1 d . . . H7 H 0.2174 0.3295 0.0542 0.032 Uiso 1 1 calc R . . C8 C 0.2772(2) 0.30328(17) 0.14971(10) 0.0233(5) Uani 1 1 d . . . C9 C 0.1757(2) 0.3472(2) 0.18053(11) 0.0300(5) Uani 1 1 d . . . H9A H 0.1701 0.3018 0.2159 0.045 Uiso 1 1 calc R . . H9B H 0.0897 0.3486 0.1509 0.045 Uiso 1 1 calc R . . H9C H 0.2004 0.4202 0.1951 0.045 Uiso 1 1 calc R . . C10 C 0.4483(3) 0.2218(2) 0.02847(10) 0.0327(6) Uani 1 1 d . . . H10A H 0.5448 0.2287 0.0384 0.049 Uiso 1 1 calc R . . H10B H 0.4099 0.2711 -0.0053 0.049 Uiso 1 1 calc R . . H10C H 0.4236 0.1481 0.0156 0.049 Uiso 1 1 calc R . . C11 C 0.4390(2) 0.25289(16) 0.24752(9) 0.0188(4) Uani 1 1 d . . . C12 C 0.4850(2) 0.16418(17) 0.28138(9) 0.0198(4) Uani 1 1 d . B . C14 C 0.6033(2) 0.10153(17) 0.38206(9) 0.0203(4) Uani 1 1 d . B . C15 C 0.7352(2) 0.10992(18) 0.37828(10) 0.0230(5) Uani 1 1 d . . . H15 H 0.7586 0.1557 0.3483 0.028 Uiso 1 1 calc R . . C16 C 0.8321(2) 0.05141(18) 0.41834(10) 0.0262(5) Uani 1 1 d . . . H16 H 0.9216 0.0576 0.4155 0.031 Uiso 1 1 calc R . . C17 C 0.8005(2) -0.01548(18) 0.46216(10) 0.0290(5) Uani 1 1 d . . . H17 H 0.8678 -0.0546 0.4896 0.035 Uiso 1 1 calc R . . C18 C 0.6706(2) -0.02534(18) 0.46599(10) 0.0291(5) Uani 1 1 d . . . H18 H 0.6481 -0.0719 0.4959 0.035 Uiso 1 1 calc R . . C19 C 0.5722(2) 0.03288(17) 0.42611(9) 0.0238(5) Uani 1 1 d . . . H19 H 0.4829 0.0256 0.4290 0.029 Uiso 1 1 calc R . . C20 C 0.6211(2) 0.01220(18) 0.10976(10) 0.0280(5) Uani 1 1 d . . . H20A H 0.5309 -0.0119 0.0893 0.034 Uiso 1 1 calc R . . H20B H 0.6615 0.0448 0.0778 0.034 Uiso 1 1 calc R . . C21 C 0.7028(3) -0.0837(2) 0.13831(14) 0.0558(9) Uani 1 1 d . . . H21A H 0.7947 -0.0614 0.1545 0.084 Uiso 1 1 calc R . . H21B H 0.6995 -0.1391 0.1066 0.084 Uiso 1 1 calc R . . H21C H 0.6671 -0.1125 0.1722 0.084 Uiso 1 1 calc R . . C22 C 0.7632(2) 0.21041(18) 0.20933(10) 0.0247(5) Uani 1 1 d . . . H22A H 0.7406 0.2563 0.2419 0.030 Uiso 1 1 calc R . . H22B H 0.8379 0.1638 0.2294 0.030 Uiso 1 1 calc R . . C23 C 0.8070(3) 0.2817(2) 0.16171(12) 0.0374(6) Uani 1 1 d . . . H23A H 0.8419 0.2369 0.1328 0.056 Uiso 1 1 calc R . . H23B H 0.8760 0.3310 0.1831 0.056 Uiso 1 1 calc R . . H23C H 0.7312 0.3229 0.1387 0.056 Uiso 1 1 calc R . . C24 C 0.4675(2) 0.2920(2) 0.46512(10) 0.0319(5) Uani 1 1 d . . . H24A H 0.5253 0.2334 0.4859 0.038 Uiso 1 1 calc R A 1 H24B H 0.5252 0.3537 0.4616 0.038 Uiso 1 1 calc R A 1 C25 C 0.3763(5) 0.3252(4) 0.5076(2) 0.0345(11) Uiso 0.50 1 d P B 1 H25A H 0.4298 0.3411 0.5492 0.052 Uiso 0.50 1 calc PR B 1 H25B H 0.3151 0.2665 0.5102 0.052 Uiso 0.50 1 calc PR B 1 H25C H 0.3260 0.3891 0.4907 0.052 Uiso 0.50 1 calc PR B 1 C25A C 0.6006(5) 0.3470(4) 0.4631(2) 0.0370(12) Uiso 0.50 1 d P B 2 H25D H 0.5830 0.4145 0.4400 0.056 Uiso 0.50 1 calc PR B 2 H25E H 0.6523 0.2996 0.4425 0.056 Uiso 0.50 1 calc PR B 2 H25F H 0.6505 0.3617 0.5055 0.056 Uiso 0.50 1 calc PR B 2 C26 C 0.2074(2) 0.1768(2) 0.36360(11) 0.0312(5) Uani 1 1 d . . . H26A H 0.1907 0.1427 0.3222 0.037 Uiso 1 1 calc R B . H26B H 0.2084 0.1193 0.3945 0.037 Uiso 1 1 calc R . . C27 C 0.0919(3) 0.2532(2) 0.36523(15) 0.0488(7) Uani 1 1 d . B . H27A H 0.1050 0.2853 0.4066 0.073 Uiso 1 1 calc R . . H27B H 0.0087 0.2130 0.3558 0.073 Uiso 1 1 calc R . . H27C H 0.0886 0.3099 0.3343 0.073 Uiso 1 1 calc R . . N1 N 0.43373(17) 0.35545(14) 0.27494(8) 0.0209(4) Uani 1 1 d . B . N2 N 0.37388(17) 0.36722(15) 0.32424(8) 0.0231(4) Uani 1 1 d . . . N3 N 0.38893(17) 0.25448(13) 0.18166(8) 0.0192(4) Uani 1 1 d . . . N4 N 0.46490(17) 0.22137(14) 0.14164(8) 0.0194(4) Uani 1 1 d . . . N5 N 0.50327(17) 0.16686(14) 0.34477(8) 0.0222(4) Uani 1 1 d . . . Al1 Al 0.61039(6) 0.12018(5) 0.17307(3) 0.01983(17) Uani 1 1 d . B . Al2 Al 0.38261(6) 0.24401(5) 0.38041(3) 0.02320(18) Uani 1 1 d . B . S1 S 0.51234(5) 0.04331(4) 0.24477(2) 0.02119(15) 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 C1 0.0255(11) 0.0290(12) 0.0261(11) -0.0044(10) 0.0030(9) 0.0098(10) C2 0.0289(12) 0.0230(12) 0.0334(12) -0.0057(10) 0.0012(10) 0.0025(10) C3 0.0228(11) 0.0202(11) 0.0258(11) -0.0020(9) 0.0041(9) 0.0004(9) C4 0.0431(15) 0.0363(14) 0.0331(13) -0.0056(11) 0.0102(11) 0.0175(12) C5 0.0287(12) 0.0214(11) 0.0343(12) 0.0007(10) 0.0109(10) -0.0026(10) C6 0.0292(12) 0.0195(11) 0.0177(10) 0.0023(8) 0.0004(9) -0.0028(9) C7 0.0286(12) 0.0243(11) 0.0232(11) 0.0036(9) -0.0035(9) -0.0001(10) C8 0.0191(10) 0.0199(11) 0.0285(11) 0.0034(9) 0.0006(9) -0.0011(9) C9 0.0196(11) 0.0336(13) 0.0346(13) 0.0006(10) 0.0018(10) 0.0048(10) C10 0.0452(15) 0.0336(13) 0.0188(11) 0.0028(10) 0.0064(10) 0.0050(11) C11 0.0184(10) 0.0215(11) 0.0165(10) -0.0017(8) 0.0039(8) 0.0010(8) C12 0.0180(10) 0.0215(11) 0.0200(10) 0.0002(9) 0.0050(8) 0.0005(8) C14 0.0242(11) 0.0206(11) 0.0150(10) -0.0014(8) 0.0023(8) 0.0033(9) C15 0.0255(11) 0.0247(11) 0.0194(10) 0.0017(9) 0.0065(9) 0.0030(9) C16 0.0241(11) 0.0293(12) 0.0237(11) -0.0048(10) 0.0025(9) 0.0059(10) C17 0.0362(13) 0.0274(12) 0.0198(11) -0.0018(9) -0.0010(10) 0.0106(10) C18 0.0466(15) 0.0212(11) 0.0206(11) 0.0026(9) 0.0098(10) 0.0041(11) C19 0.0291(12) 0.0241(11) 0.0198(10) -0.0012(9) 0.0090(9) 0.0002(9) C20 0.0322(12) 0.0266(12) 0.0252(11) -0.0014(9) 0.0062(10) 0.0015(10) C21 0.068(2) 0.0388(16) 0.0478(17) -0.0177(13) -0.0133(15) 0.0205(15) C22 0.0203(11) 0.0250(11) 0.0280(11) 0.0021(9) 0.0039(9) 0.0037(9) C23 0.0342(14) 0.0359(14) 0.0455(15) -0.0007(12) 0.0160(12) -0.0091(11) C24 0.0326(13) 0.0377(14) 0.0241(11) 0.0031(10) 0.0035(10) 0.0002(11) C26 0.0270(12) 0.0345(13) 0.0315(12) 0.0010(11) 0.0056(10) 0.0009(10) C27 0.0264(14) 0.0471(17) 0.076(2) -0.0019(15) 0.0176(14) -0.0015(12) N1 0.0209(9) 0.0207(9) 0.0209(9) -0.0016(7) 0.0043(7) 0.0026(7) N2 0.0224(9) 0.0280(10) 0.0192(9) -0.0032(8) 0.0055(7) 0.0058(8) N3 0.0203(9) 0.0190(9) 0.0180(9) 0.0015(7) 0.0037(7) 0.0002(7) N4 0.0224(9) 0.0187(9) 0.0175(8) -0.0003(7) 0.0053(7) -0.0006(7) N5 0.0224(9) 0.0268(10) 0.0172(9) 0.0021(7) 0.0043(7) 0.0062(8) Al1 0.0231(3) 0.0180(3) 0.0188(3) 0.0005(2) 0.0055(3) 0.0002(3) Al2 0.0210(3) 0.0308(4) 0.0181(3) -0.0004(3) 0.0051(3) 0.0054(3) S1 0.0263(3) 0.0181(3) 0.0196(3) 0.0016(2) 0.0060(2) 0.0003(2) _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 C1 N2 1.348(3) . ? C1 C2 1.386(4) . ? C1 C4 1.493(3) . ? C2 C3 1.380(3) . ? C3 N1 1.356(3) . ? C3 C5 1.483(3) . ? C6 N4 1.344(3) . ? C6 C7 1.387(3) . ? C6 C10 1.493(3) . ? C7 C8 1.380(3) . ? C8 N3 1.357(3) . ? C8 C9 1.487(3) . ? C11 C12 1.361(3) . ? C11 N1 1.423(3) . ? C11 N3 1.432(2) . ? C12 N5 1.374(3) . ? C12 S1 1.766(2) . ? C14 C19 1.391(3) . ? C14 C15 1.397(3) . ? C14 N5 1.426(3) . ? C15 C16 1.387(3) . ? C16 C17 1.376(3) . ? C17 C18 1.378(3) . ? C18 C19 1.392(3) . ? C20 C21 1.519(3) . ? C20 Al1 1.966(2) . ? C22 C23 1.527(3) . ? C22 Al1 1.962(2) . ? C24 C25 1.539(5) . ? C24 C25A 1.555(6) . ? C24 Al2 1.974(2) . ? C26 C27 1.539(3) . ? C26 Al2 1.962(2) . ? N1 N2 1.383(2) . ? N2 Al2 1.966(2) . ? N3 N4 1.379(2) . ? N4 Al1 1.9703(18) . ? N5 Al2 1.8914(19) . ? Al1 S1 2.2858(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 C2 109.9(2) . . ? N2 C1 C4 121.0(2) . . ? C2 C1 C4 129.1(2) . . ? C3 C2 C1 107.1(2) . . ? N1 C3 C2 106.8(2) . . ? N1 C3 C5 122.34(19) . . ? C2 C3 C5 130.9(2) . . ? N4 C6 C7 109.72(19) . . ? N4 C6 C10 121.2(2) . . ? C7 C6 C10 129.05(19) . . ? C8 C7 C6 107.04(19) . . ? N3 C8 C7 106.74(19) . . ? N3 C8 C9 122.58(19) . . ? C7 C8 C9 130.7(2) . . ? C12 C11 N1 122.64(18) . . ? C12 C11 N3 124.91(18) . . ? N1 C11 N3 112.44(16) . . ? C11 C12 N5 119.48(19) . . ? C11 C12 S1 120.99(16) . . ? N5 C12 S1 119.42(15) . . ? C19 C14 C15 118.52(19) . . ? C19 C14 N5 120.16(19) . . ? C15 C14 N5 121.19(19) . . ? C16 C15 C14 120.0(2) . . ? C17 C16 C15 121.0(2) . . ? C16 C17 C18 119.6(2) . . ? C17 C18 C19 120.1(2) . . ? C14 C19 C18 120.8(2) . . ? C21 C20 Al1 111.15(16) . . ? C23 C22 Al1 113.16(15) . . ? C25 C24 C25A 125.2(3) . . ? C25 C24 Al2 117.4(2) . . ? C25A C24 Al2 108.2(2) . . ? C27 C26 Al2 115.21(17) . . ? C3 N1 N2 110.45(17) . . ? C3 N1 C11 129.05(18) . . ? N2 N1 C11 120.06(17) . . ? C1 N2 N1 105.79(18) . . ? C1 N2 Al2 131.31(15) . . ? N1 N2 Al2 116.92(13) . . ? C8 N3 N4 110.30(16) . . ? C8 N3 C11 127.20(18) . . ? N4 N3 C11 121.52(16) . . ? C6 N4 N3 106.18(17) . . ? C6 N4 Al1 133.44(15) . . ? N3 N4 Al1 118.11(12) . . ? C12 N5 C14 119.29(17) . . ? C12 N5 Al2 119.35(14) . . ? C14 N5 Al2 120.96(14) . . ? C22 Al1 C20 120.80(10) . . ? C22 Al1 N4 105.10(9) . . ? C20 Al1 N4 110.59(9) . . ? C22 Al1 S1 113.86(7) . . ? C20 Al1 S1 108.39(8) . . ? N4 Al1 S1 94.92(6) . . ? N5 Al2 C26 112.28(10) . . ? N5 Al2 N2 94.15(8) . . ? C26 Al2 N2 107.95(9) . . ? N5 Al2 C24 110.90(9) . . ? C26 Al2 C24 120.18(11) . . ? N2 Al2 C24 108.05(10) . . ? C12 S1 Al1 96.03(7) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.567 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.067 _database_code_depnum_ccdc_archive 'CCDC 756898' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 # start Validation Reply Form _vrf_THETM01_1 ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.5498 RESPONSE: Crystals were very small and weakly diffracting and this is reflected in the low fraction of measured reflections ; _vrf_RINTA01_1 ; PROBLEM: The value of Rint is greater than 0.18 Rint given 0.189 RESPONSE: The quality of the crystal was not optimal and it was weakly diffracting. Although recrystallization was attempted repeatedly, better crystals were not obtained. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H31 Al2 N5 S' _chemical_formula_sum 'C22 H31 Al2 N5 S' _chemical_formula_weight 451.54 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.387(8) _cell_length_b 19.980(8) _cell_length_c 18.787(8) _cell_angle_alpha 90.00 _cell_angle_beta 97.839(11) _cell_angle_gamma 90.00 _cell_volume 5721(4) _cell_formula_units_Z 8 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 178 _cell_measurement_theta_min 2.189 _cell_measurement_theta_max 12.297 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.048 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.190 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9775 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13309 _diffrn_reflns_av_R_equivalents 0.1886 _diffrn_reflns_av_unetI/netI 0.2785 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 23.00 _reflns_number_total 3962 _reflns_number_gt 1300 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX v1.70 (Farrugia, 1999)' _computing_publication_material 'WINGX v1.70 (Farrugia, 1999)' _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. The compound crystallise with some molecules of toluene solvent which were found heavily disordered. An investigation of the void space in the structure show four principal voids of about 222 A3 in the unit cell. The option squeeze in Platon (Spek, A. L. Acta Crystallogr. 1990, A46, C-34) was used to eliminate the contribution of the electron density in the solvent region from the intensity data. The derived quantities (Mr, F(000), and Dx in the Crystal data are corrected with the contribution from this disordered solvent. ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.322 0.250 222 72 ' ' 2 0.000 0.771 0.250 10 1 ' ' 3 0.000 0.678 0.750 222 70 ' ' 4 0.000 0.229 0.750 10 1 ' ' 5 0.500 0.822 0.250 222 72 ' ' 6 0.500 0.178 0.750 222 70 ' ' 7 0.500 0.271 0.250 10 1 ' ' 8 0.500 0.729 0.750 10 1 ' ' _platon_squeeze_details ? _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^)+(0.0384P)^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 3962 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1924 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.1980 _refine_ls_wR_factor_gt 0.1586 _refine_ls_goodness_of_fit_ref 0.792 _refine_ls_restrained_S_all 0.792 _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 Al1 Al 0.18179(15) 0.11259(10) 0.42746(11) 0.0532(7) Uani 1 1 d . . . Al2 Al 0.30219(16) -0.12603(11) 0.59343(12) 0.0636(8) Uani 1 1 d . . . S1 S 0.29196(13) -0.01304(9) 0.60931(9) 0.0595(7) Uani 1 1 d . . . N1 N 0.2096(4) 0.0411(3) 0.3622(3) 0.0460(16) Uani 1 1 d . . . N2 N 0.2363(4) -0.0197(3) 0.3913(3) 0.0485(16) Uani 1 1 d . . . N3 N 0.3589(4) -0.0602(3) 0.4721(3) 0.0500(16) Uani 1 1 d . . . N4 N 0.3691(4) -0.1189(3) 0.5119(3) 0.0553(17) Uani 1 1 d . . . N5 N 0.1848(4) 0.0560(3) 0.5075(3) 0.0426(15) Uani 1 1 d . . . C1 C 0.2262(4) -0.0687(4) 0.3397(4) 0.048(2) Uani 1 1 d . . . C2 C 0.1942(5) -0.0369(4) 0.2765(4) 0.058(2) Uani 1 1 d . . . H2 H 0.1826 -0.0564 0.2313 0.069 Uiso 1 1 calc R . . C3 C 0.1825(5) 0.0296(5) 0.2930(4) 0.061(2) Uani 1 1 d . . . C4 C 0.2491(5) -0.1404(3) 0.3557(4) 0.067(2) Uani 1 1 d . . . H4A H 0.3117 -0.1455 0.3625 0.101 Uiso 1 1 calc R . . H4B H 0.2239 -0.1679 0.3163 0.101 Uiso 1 1 calc R . . H4C H 0.2263 -0.1538 0.3987 0.101 Uiso 1 1 calc R . . C5 C 0.1454(5) 0.0852(3) 0.2448(3) 0.070(2) Uani 1 1 d . . . H5A H 0.0830 0.0874 0.2448 0.105 Uiso 1 1 calc R . . H5B H 0.1577 0.0770 0.1969 0.105 Uiso 1 1 calc R . . H5C H 0.1715 0.1268 0.2619 0.105 Uiso 1 1 calc R . . C6 C 0.4468(6) -0.1438(4) 0.4984(5) 0.064(2) Uani 1 1 d . . . C7 C 0.4821(6) -0.1033(4) 0.4505(4) 0.068(2) Uani 1 1 d . . . H7 H 0.5343 -0.1108 0.4320 0.081 Uiso 1 1 calc R . . C8 C 0.4277(6) -0.0510(4) 0.4352(4) 0.053(2) Uani 1 1 d . . . C9 C 0.4814(5) -0.2089(4) 0.5346(4) 0.083(3) Uani 1 1 d . . . H9A H 0.4911 -0.2028 0.5857 0.124 Uiso 1 1 calc R . . H9B H 0.5356 -0.2209 0.5180 0.124 Uiso 1 1 calc R . . H9C H 0.4392 -0.2439 0.5227 0.124 Uiso 1 1 calc R . . C10 C 0.4340(5) 0.0085(3) 0.3878(4) 0.073(2) Uani 1 1 d . . . H10A H 0.3980 0.0014 0.3426 0.109 Uiso 1 1 calc R . . H10B H 0.4939 0.0146 0.3800 0.109 Uiso 1 1 calc R . . H10C H 0.4142 0.0477 0.4105 0.109 Uiso 1 1 calc R . . C11 C 0.2768(5) -0.0245(3) 0.4651(4) 0.050(2) Uani 1 1 d . . . C12 C 0.2476(5) 0.0081(4) 0.5208(4) 0.049(2) Uani 1 1 d . . . C13 C 0.1302(5) 0.0705(4) 0.5609(4) 0.051(2) Uani 1 1 d . . . C14 C 0.0688(5) 0.0271(4) 0.5792(4) 0.055(2) Uani 1 1 d . . . H14 H 0.0675 -0.0162 0.5607 0.066 Uiso 1 1 calc R . . C15 C 0.0080(6) 0.0447(5) 0.6243(4) 0.078(3) Uani 1 1 d . . . H15 H -0.0343 0.0144 0.6348 0.094 Uiso 1 1 calc R . . C16 C 0.0119(6) 0.1069(6) 0.6522(4) 0.078(3) Uani 1 1 d . . . H16 H -0.0271 0.1188 0.6838 0.093 Uiso 1 1 calc R . . C17 C 0.0710(7) 0.1525(4) 0.6357(4) 0.075(3) Uani 1 1 d . . . H17 H 0.0709 0.1955 0.6546 0.090 Uiso 1 1 calc R . . C18 C 0.1324(5) 0.1351(4) 0.5900(4) 0.056(2) Uani 1 1 d . . . H18 H 0.1740 0.1660 0.5793 0.067 Uiso 1 1 calc R . . C19 C 0.0629(5) 0.1453(3) 0.3999(4) 0.075(3) Uani 1 1 d . . . H19A H 0.0223 0.1165 0.4196 0.112 Uiso 1 1 calc R . . H19B H 0.0496 0.1457 0.3485 0.112 Uiso 1 1 calc R . . H19C H 0.0580 0.1899 0.4180 0.112 Uiso 1 1 calc R . . C20 C 0.2782(5) 0.1763(3) 0.4329(4) 0.077(3) Uani 1 1 d . . . H20A H 0.2568 0.2204 0.4409 0.116 Uiso 1 1 calc R . . H20B H 0.3028 0.1757 0.3886 0.116 Uiso 1 1 calc R . . H20C H 0.3225 0.1643 0.4718 0.116 Uiso 1 1 calc R . . C21 C 0.1906(5) -0.1712(3) 0.5583(4) 0.085(3) Uani 1 1 d . . . H21A H 0.1555 -0.1425 0.5249 0.128 Uiso 1 1 calc R . . H21B H 0.1596 -0.1807 0.5981 0.128 Uiso 1 1 calc R . . H21C H 0.2024 -0.2122 0.5348 0.128 Uiso 1 1 calc R . . C22 C 0.3734(6) -0.1636(4) 0.6784(4) 0.101(3) Uani 1 1 d . . . H22A H 0.3777 -0.2112 0.6730 0.152 Uiso 1 1 calc R . . H22B H 0.3463 -0.1537 0.7203 0.152 Uiso 1 1 calc R . . H22C H 0.4310 -0.1442 0.6835 0.152 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 Al1 0.0612(18) 0.0478(13) 0.0510(14) 0.0009(12) 0.0090(13) -0.0004(12) Al2 0.0585(18) 0.0638(16) 0.0663(16) 0.0131(13) 0.0009(14) 0.0002(13) S1 0.0616(16) 0.0670(14) 0.0478(12) 0.0012(11) -0.0006(11) 0.0024(11) N1 0.053(4) 0.038(4) 0.048(4) 0.006(3) 0.012(3) 0.005(3) N2 0.056(5) 0.056(4) 0.033(4) -0.013(4) 0.004(3) -0.006(3) N3 0.050(5) 0.047(4) 0.052(4) 0.002(3) 0.001(4) 0.001(4) N4 0.040(5) 0.053(4) 0.075(4) 0.007(4) 0.013(4) 0.001(3) N5 0.044(4) 0.044(4) 0.043(4) 0.003(3) 0.014(3) 0.000(3) C1 0.043(5) 0.058(5) 0.044(5) -0.018(5) 0.008(4) -0.007(4) C2 0.069(6) 0.065(6) 0.039(5) -0.012(5) 0.006(5) 0.004(5) C3 0.054(6) 0.090(7) 0.039(5) 0.004(5) 0.008(5) -0.001(5) C4 0.079(7) 0.059(5) 0.063(5) -0.014(4) 0.005(5) 0.006(5) C5 0.091(7) 0.078(6) 0.040(4) 0.008(4) 0.002(5) 0.012(5) C6 0.044(6) 0.059(6) 0.083(6) -0.011(5) -0.014(5) 0.003(5) C7 0.071(7) 0.065(6) 0.072(6) 0.010(5) 0.028(5) -0.005(6) C8 0.048(6) 0.055(6) 0.057(5) -0.003(5) 0.012(5) -0.006(5) C9 0.069(7) 0.079(6) 0.096(6) -0.001(5) -0.001(5) 0.009(5) C10 0.073(6) 0.081(6) 0.069(5) 0.011(5) 0.022(5) 0.000(5) C11 0.054(6) 0.055(5) 0.037(5) 0.001(4) -0.005(5) 0.003(4) C12 0.049(6) 0.052(5) 0.046(5) 0.003(4) 0.009(4) -0.015(4) C13 0.048(6) 0.056(5) 0.048(5) 0.007(4) 0.011(5) 0.005(4) C14 0.044(6) 0.075(6) 0.048(5) -0.006(4) 0.013(5) -0.008(5) C15 0.075(7) 0.096(7) 0.066(6) -0.020(6) 0.022(6) -0.022(6) C16 0.062(7) 0.120(9) 0.055(6) -0.002(6) 0.020(5) 0.000(6) C17 0.097(8) 0.068(6) 0.060(6) 0.007(5) 0.012(6) 0.039(6) C18 0.068(6) 0.048(5) 0.056(5) 0.011(4) 0.021(5) -0.003(4) C19 0.076(7) 0.094(6) 0.055(5) 0.024(5) 0.011(5) 0.020(5) C20 0.096(7) 0.064(5) 0.077(6) -0.007(4) 0.030(5) -0.021(5) C21 0.070(7) 0.077(6) 0.110(7) -0.008(5) 0.020(6) -0.003(5) C22 0.117(8) 0.102(6) 0.085(6) 0.035(6) 0.014(6) 0.026(6) _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 Al1 N5 1.877(5) . ? Al1 C19 1.946(7) . ? Al1 C20 1.947(7) . ? Al1 N1 1.967(6) . ? Al2 C22 1.957(8) . ? Al2 N4 1.964(6) . ? Al2 C21 1.972(7) . ? Al2 S1 2.285(3) . ? S1 C12 1.760(7) . ? N1 C3 1.329(8) . ? N1 N2 1.371(7) . ? N2 C1 1.371(7) . ? N2 C11 1.443(8) . ? N3 C8 1.354(8) . ? N3 N4 1.387(6) . ? N3 C11 1.442(8) . ? N4 C6 1.351(8) . ? N5 C12 1.358(8) . ? N5 C13 1.424(8) . ? C1 C2 1.377(9) . ? C1 C4 1.496(8) . ? C2 C3 1.380(9) . ? C3 C5 1.497(9) . ? C6 C7 1.375(9) . ? C6 C9 1.529(9) . ? C7 C8 1.346(9) . ? C8 C10 1.496(9) . ? C11 C12 1.361(8) . ? C13 C14 1.360(8) . ? C13 C18 1.401(8) . ? C14 C15 1.391(9) . ? C15 C16 1.347(10) . ? C16 C17 1.354(10) . ? C17 C18 1.404(9) . ? 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 N5 Al1 C19 109.6(3) . . ? N5 Al1 C20 114.6(3) . . ? C19 Al1 C20 118.5(3) . . ? N5 Al1 N1 94.5(3) . . ? C19 Al1 N1 110.8(3) . . ? C20 Al1 N1 106.2(3) . . ? C22 Al2 N4 111.7(3) . . ? C22 Al2 C21 117.6(3) . . ? N4 Al2 C21 107.3(3) . . ? C22 Al2 S1 108.2(3) . . ? N4 Al2 S1 94.8(2) . . ? C21 Al2 S1 115.0(2) . . ? C12 S1 Al2 98.0(3) . . ? C3 N1 N2 105.8(6) . . ? C3 N1 Al1 132.0(6) . . ? N2 N1 Al1 118.3(4) . . ? N1 N2 C1 110.6(5) . . ? N1 N2 C11 120.6(6) . . ? C1 N2 C11 128.6(6) . . ? C8 N3 N4 110.6(6) . . ? C8 N3 C11 128.5(7) . . ? N4 N3 C11 120.0(6) . . ? C6 N4 N3 104.4(6) . . ? C6 N4 Al2 133.7(6) . . ? N3 N4 Al2 116.7(5) . . ? C12 N5 C13 119.1(6) . . ? C12 N5 Al1 120.8(4) . . ? C13 N5 Al1 119.3(5) . . ? N2 C1 C2 105.8(6) . . ? N2 C1 C4 122.7(7) . . ? C2 C1 C4 131.5(7) . . ? C1 C2 C3 107.0(7) . . ? N1 C3 C2 110.7(7) . . ? N1 C3 C5 120.4(7) . . ? C2 C3 C5 128.9(7) . . ? N4 C6 C7 110.1(7) . . ? N4 C6 C9 119.6(8) . . ? C7 C6 C9 130.3(8) . . ? C8 C7 C6 107.9(8) . . ? C7 C8 N3 106.9(7) . . ? C7 C8 C10 131.0(8) . . ? N3 C8 C10 122.1(8) . . ? C12 C11 N3 122.9(7) . . ? C12 C11 N2 124.3(7) . . ? N3 C11 N2 112.3(6) . . ? N5 C12 C11 119.7(6) . . ? N5 C12 S1 121.2(6) . . ? C11 C12 S1 119.1(6) . . ? C14 C13 C18 118.1(7) . . ? C14 C13 N5 123.0(7) . . ? C18 C13 N5 118.5(7) . . ? C13 C14 C15 122.6(7) . . ? C16 C15 C14 118.3(8) . . ? C15 C16 C17 121.8(8) . . ? C16 C17 C18 120.1(8) . . ? C13 C18 C17 119.0(7) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.251 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 933658' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H43 Al2 N5 O' _chemical_formula_sum 'C24 H43 Al2 N5 O' _chemical_formula_weight 471.59 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 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' _cell_length_a 9.669(4) _cell_length_b 15.243(6) _cell_length_c 18.934(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2791(2) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 369 _cell_measurement_theta_min 2.494 _cell_measurement_theta_max 15.969 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9712 _exptl_absorpt_correction_T_max 0.9848 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10094 _diffrn_reflns_av_R_equivalents 0.1190 _diffrn_reflns_av_unetI/netI 0.2039 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4503 _reflns_number_gt 1913 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX v1.70 (Farrugia, 1999)' _computing_publication_material 'WINGX v1.70 (Farrugia, 1999)' _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. Complexes 6, 13 and 16 show high disorder in the sec-buthyl and ethyl groups DFIX instruction of SHELX has been used to restrain the distances between these atoms. ; _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^)+(0.0718P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 4503 _refine_ls_number_parameters 351 _refine_ls_number_restraints 122 _refine_ls_R_factor_all 0.1952 _refine_ls_R_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.2023 _refine_ls_wR_factor_gt 0.1524 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.918 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Al1 Al 0.6454(2) 0.08261(15) 0.40353(11) 0.0625(7) Uani 1 1 d D . . Al2 Al 0.1966(2) -0.06113(15) 0.53651(13) 0.0729(8) Uani 1 1 d D . . N1 N 0.3508(6) -0.0819(4) 0.6020(3) 0.0576(15) Uani 1 1 d . C . N2 N 0.4775(6) -0.0500(4) 0.5821(3) 0.0547(15) Uani 1 1 d . . . N3 N 0.6766(6) 0.1158(4) 0.5014(3) 0.0564(16) Uani 1 1 d . B . N4 N 0.5736(5) 0.0885(3) 0.5475(3) 0.0511(14) Uani 1 1 d . . . N5 N 0.3087(7) -0.0386(4) 0.4573(3) 0.0671(17) Uani 1 1 d D A . O1 O 0.4623(4) 0.0676(3) 0.4142(2) 0.0597(12) Uani 1 1 d . B . C1 C 0.5813(9) -0.0866(5) 0.6206(4) 0.062(2) Uani 1 1 d . C . C2 C 0.5187(11) -0.1442(5) 0.6668(4) 0.080(3) Uani 1 1 d . . . H2 H 0.5639 -0.1803 0.7006 0.096 Uiso 1 1 calc R C . C3 C 0.3775(10) -0.1395(5) 0.6547(4) 0.069(2) Uani 1 1 d . C . C4 C 0.7309(7) -0.0668(5) 0.6074(4) 0.074(2) Uani 1 1 d . . . H4A H 0.7490 -0.0679 0.5564 0.112 Uiso 1 1 calc R C . H4B H 0.7883 -0.1111 0.6308 0.112 Uiso 1 1 calc R . . H4C H 0.7532 -0.0086 0.6262 0.112 Uiso 1 1 calc R . . C5 C 0.2628(10) -0.1899(6) 0.6894(4) 0.104(3) Uani 1 1 d . . . H5A H 0.1790 -0.1537 0.6905 0.156 Uiso 1 1 calc R C . H5B H 0.2898 -0.2052 0.7377 0.156 Uiso 1 1 calc R . . H5C H 0.2446 -0.2436 0.6625 0.156 Uiso 1 1 calc R . . C6 C 0.5799(8) 0.1357(5) 0.6081(4) 0.0550(18) Uani 1 1 d . B . C7 C 0.6896(8) 0.1934(5) 0.6013(5) 0.070(2) Uani 1 1 d . . . H7 H 0.7217 0.2340 0.6356 0.083 Uiso 1 1 calc R B . C8 C 0.7429(8) 0.1802(5) 0.5346(4) 0.059(2) Uani 1 1 d . B . C9 C 0.4770(8) 0.1211(5) 0.6656(3) 0.068(2) Uani 1 1 d . . . H9A H 0.3833 0.1245 0.6461 0.103 Uiso 1 1 calc R B . H9B H 0.4884 0.1663 0.7020 0.103 Uiso 1 1 calc R . . H9C H 0.4916 0.0631 0.6866 0.103 Uiso 1 1 calc R . . C10 C 0.8597(8) 0.2286(5) 0.5007(4) 0.079(2) Uani 1 1 d . . . H10A H 0.9240 0.2491 0.5371 0.118 Uiso 1 1 calc R B . H10B H 0.8233 0.2791 0.4746 0.118 Uiso 1 1 calc R . . H10C H 0.9084 0.1894 0.4680 0.118 Uiso 1 1 calc R . . C11 C 0.4870(7) 0.0165(4) 0.5305(4) 0.0525(18) Uani 1 1 d . B . C12 C 0.4190(8) 0.0131(4) 0.4654(4) 0.0545(17) Uani 1 1 d . . . C13 C 0.286(3) -0.052(2) 0.3790(11) 0.098(8) Uani 0.50 1 d PDU A 1 H13 H 0.3332 0.0011 0.3589 0.117 Uiso 0.50 1 calc PR A 1 C14 C 0.362(2) -0.1210(13) 0.3472(11) 0.098(6) Uani 0.50 1 d PDU A 1 H14A H 0.4537 -0.0994 0.3329 0.146 Uiso 0.50 1 calc PR A 1 H14B H 0.3125 -0.1422 0.3055 0.146 Uiso 0.50 1 calc PR A 1 H14C H 0.3734 -0.1690 0.3811 0.146 Uiso 0.50 1 calc PR A 1 C15 C 0.145(2) -0.0345(14) 0.3623(13) 0.108(6) Uani 0.50 1 d PDU A 1 H15A H 0.0821 -0.0595 0.3985 0.130 Uiso 0.50 1 calc PR A 1 H15B H 0.1198 -0.0591 0.3156 0.130 Uiso 0.50 1 calc PR A 1 C16 C 0.137(4) 0.066(2) 0.3616(17) 0.102(7) Uani 0.50 1 d PDU A 1 H16A H 0.1369 0.0876 0.4103 0.153 Uiso 0.50 1 calc PR A 1 H16B H 0.0515 0.0842 0.3380 0.153 Uiso 0.50 1 calc PR A 1 H16C H 0.2168 0.0894 0.3363 0.153 Uiso 0.50 1 calc PR A 1 C13A C 0.261(3) -0.0685(17) 0.3820(10) 0.077(6) Uani 0.50 1 d PDU A 2 H13A H 0.1692 -0.0895 0.3994 0.092 Uiso 0.50 1 calc PR A 2 C14A C 0.310(2) -0.1609(11) 0.3632(11) 0.096(6) Uani 0.50 1 d PDU A 2 H14D H 0.2566 -0.2039 0.3905 0.144 Uiso 0.50 1 calc PR A 2 H14E H 0.4082 -0.1669 0.3744 0.144 Uiso 0.50 1 calc PR A 2 H14F H 0.2954 -0.1713 0.3127 0.144 Uiso 0.50 1 calc PR A 2 C15A C 0.199(2) 0.0104(13) 0.3448(11) 0.094(6) Uani 0.50 1 d PDU A 2 H15C H 0.2771 0.0457 0.3266 0.113 Uiso 0.50 1 calc PR A 2 H15D H 0.1487 -0.0123 0.3030 0.113 Uiso 0.50 1 calc PR A 2 C16A C 0.102(4) 0.074(2) 0.3818(16) 0.098(7) Uani 0.50 1 d PDU A 2 H16D H 0.0134 0.0445 0.3913 0.148 Uiso 0.50 1 calc PR A 2 H16E H 0.0857 0.1250 0.3515 0.148 Uiso 0.50 1 calc PR A 2 H16F H 0.1432 0.0929 0.4265 0.148 Uiso 0.50 1 calc PR A 2 C17 C 0.731(3) -0.0304(13) 0.3801(11) 0.070(11) Uiso 0.50 1 d PD B 1 H17A H 0.8255 -0.0327 0.4004 0.084 Uiso 0.50 1 calc PR B 1 H17B H 0.6764 -0.0785 0.4012 0.084 Uiso 0.50 1 calc PR B 1 C18 C 0.739(2) -0.0435(13) 0.2996(9) 0.082(7) Uiso 0.50 1 d PD B 1 H18A H 0.6473 -0.0359 0.2789 0.123 Uiso 0.50 1 calc PR B 1 H18B H 0.7734 -0.1027 0.2894 0.123 Uiso 0.50 1 calc PR B 1 H18C H 0.8029 -0.0002 0.2793 0.123 Uiso 0.50 1 calc PR B 1 C17A C 0.754(3) -0.0245(14) 0.3894(12) 0.074(11) Uiso 0.50 1 d PD B 2 H17C H 0.8421 -0.0166 0.4149 0.089 Uiso 0.50 1 calc PR B 2 H17D H 0.7035 -0.0727 0.4134 0.089 Uiso 0.50 1 calc PR B 2 C18A C 0.789(2) -0.0567(15) 0.3141(11) 0.102(8) Uiso 0.50 1 d PD B 2 H18D H 0.7044 -0.0763 0.2904 0.153 Uiso 0.50 1 calc PR B 2 H18E H 0.8546 -0.1056 0.3170 0.153 Uiso 0.50 1 calc PR B 2 H18F H 0.8307 -0.0085 0.2872 0.153 Uiso 0.50 1 calc PR B 2 C19 C 0.677(5) 0.188(2) 0.3449(16) 0.065(11) Uiso 0.50 1 d PD B 1 H19A H 0.6543 0.2419 0.3716 0.078 Uiso 0.50 1 calc PR B 1 H19B H 0.7748 0.1911 0.3294 0.078 Uiso 0.50 1 calc PR B 1 C20 C 0.580(2) 0.1771(15) 0.2806(11) 0.098(9) Uiso 0.50 1 d PD B 1 H20A H 0.6024 0.1227 0.2556 0.148 Uiso 0.50 1 calc PR B 1 H20B H 0.5911 0.2271 0.2486 0.148 Uiso 0.50 1 calc PR B 1 H20C H 0.4835 0.1746 0.2969 0.148 Uiso 0.50 1 calc PR B 1 C19A C 0.653(7) 0.186(5) 0.341(5) 0.08(3) Uiso 0.25 1 d PD B 2 H19C H 0.6579 0.2391 0.3712 0.102 Uiso 0.25 1 calc PR B 2 H19D H 0.7399 0.1832 0.3137 0.102 Uiso 0.25 1 calc PR B 2 C20A C 0.533(3) 0.199(2) 0.2884(15) 0.039(8) Uiso 0.25 1 d PD B 2 H20D H 0.4932 0.1415 0.2764 0.058 Uiso 0.25 1 calc PR B 2 H20E H 0.5675 0.2272 0.2455 0.058 Uiso 0.25 1 calc PR B 2 H20F H 0.4613 0.2357 0.3100 0.058 Uiso 0.25 1 calc PR B 2 C19B C 0.687(5) 0.163(3) 0.326(3) 0.092(18) Uiso 0.25 1 d PD B 3 H19E H 0.7816 0.1866 0.3316 0.110 Uiso 0.25 1 calc PR B 3 H19F H 0.6806 0.1320 0.2806 0.110 Uiso 0.25 1 calc PR B 3 C20B C 0.582(4) 0.238(2) 0.329(2) 0.091(11) Uiso 0.25 1 d PD B 3 H20G H 0.4881 0.2130 0.3315 0.136 Uiso 0.25 1 calc PR B 3 H20H H 0.5903 0.2735 0.2863 0.136 Uiso 0.25 1 calc PR B 3 H20I H 0.5989 0.2739 0.3707 0.136 Uiso 0.25 1 calc PR B 3 C21 C 0.048(3) -0.1471(19) 0.5358(16) 0.086(12) Uiso 0.30 1 d PD C 1 H21A H 0.0576 -0.1779 0.5816 0.103 Uiso 0.30 1 calc PR C 1 H21B H -0.0371 -0.1117 0.5397 0.103 Uiso 0.30 1 calc PR C 1 C22 C 0.013(4) -0.216(2) 0.4862(16) 0.143(14) Uiso 0.30 1 d PD C 1 H22A H -0.0876 -0.2168 0.4792 0.215 Uiso 0.30 1 calc PR C 1 H22B H 0.0433 -0.2726 0.5048 0.215 Uiso 0.30 1 calc PR C 1 H22C H 0.0587 -0.2045 0.4409 0.215 Uiso 0.30 1 calc PR C 1 C21A C 0.0891(14) -0.1702(8) 0.5287(8) 0.090(6) Uiso 0.70 1 d PD C 2 H21C H 0.0437 -0.1789 0.5751 0.108 Uiso 0.70 1 calc PR C 2 H21D H 0.0142 -0.1583 0.4944 0.108 Uiso 0.70 1 calc PR C 2 C22A C 0.1428(12) -0.2470(7) 0.5109(6) 0.076(3) Uiso 0.70 1 d PD C 2 H22D H 0.1779 -0.2440 0.4624 0.114 Uiso 0.70 1 calc PR C 2 H22E H 0.0714 -0.2925 0.5140 0.114 Uiso 0.70 1 calc PR C 2 H22F H 0.2189 -0.2614 0.5431 0.114 Uiso 0.70 1 calc PR C 2 C23 C 0.0992(8) 0.0434(5) 0.5722(4) 0.086(3) Uani 1 1 d . C . H23A H 0.1564 0.0958 0.5620 0.103 Uiso 1 1 calc R . . H23B H 0.0114 0.0499 0.5458 0.103 Uiso 1 1 calc R . . C24 C 0.0662(9) 0.0419(6) 0.6517(5) 0.107(3) Uani 1 1 d . . . H24A H 0.0175 -0.0126 0.6634 0.160 Uiso 1 1 calc R C . H24B H 0.0076 0.0922 0.6636 0.160 Uiso 1 1 calc R . . H24C H 0.1525 0.0451 0.6787 0.160 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 Al1 0.0615(15) 0.0711(14) 0.0548(13) 0.0088(13) 0.0085(12) -0.0011(12) Al2 0.0693(16) 0.0850(16) 0.0644(14) 0.0139(14) -0.0062(13) -0.0295(14) N1 0.060(4) 0.059(3) 0.053(4) 0.009(4) -0.008(3) -0.010(3) N2 0.060(4) 0.056(4) 0.049(3) 0.005(3) -0.006(3) -0.001(4) N3 0.058(4) 0.056(4) 0.055(3) 0.006(3) 0.008(3) -0.005(3) N4 0.047(4) 0.051(3) 0.055(4) 0.005(3) -0.002(3) 0.009(3) N5 0.079(4) 0.081(4) 0.041(3) 0.003(3) -0.015(3) -0.019(4) O1 0.066(3) 0.069(3) 0.044(3) 0.010(3) 0.001(3) -0.008(3) C1 0.072(6) 0.058(4) 0.055(4) -0.004(4) -0.008(4) 0.009(5) C2 0.114(9) 0.066(5) 0.059(5) 0.024(5) 0.007(6) 0.009(6) C3 0.084(7) 0.068(5) 0.055(5) 0.005(5) 0.001(5) -0.002(5) C4 0.058(6) 0.075(5) 0.089(6) 0.005(5) -0.015(5) 0.013(5) C5 0.134(9) 0.099(7) 0.079(6) 0.032(5) 0.009(6) -0.041(6) C6 0.060(5) 0.059(4) 0.046(4) -0.006(4) -0.005(4) 0.007(4) C7 0.067(6) 0.060(5) 0.082(6) -0.011(5) -0.012(5) -0.010(5) C8 0.058(5) 0.058(5) 0.063(5) -0.003(5) 0.001(5) -0.002(4) C9 0.067(5) 0.081(5) 0.058(5) -0.020(4) 0.008(4) 0.017(4) C10 0.079(6) 0.069(5) 0.089(6) 0.009(5) -0.003(5) -0.007(5) C11 0.065(5) 0.045(4) 0.048(4) 0.005(4) -0.001(4) -0.010(4) C12 0.053(5) 0.056(4) 0.055(5) -0.004(4) -0.005(4) -0.002(4) C13 0.123(13) 0.081(14) 0.089(12) -0.002(10) -0.034(10) -0.027(12) C14 0.116(13) 0.113(13) 0.064(10) -0.031(9) 0.005(9) -0.043(10) C15 0.106(12) 0.118(11) 0.100(14) 0.004(12) 0.008(12) -0.037(11) C16 0.107(16) 0.116(10) 0.082(14) 0.028(11) -0.009(12) -0.014(9) C13A 0.093(13) 0.067(10) 0.070(10) 0.008(8) -0.031(9) -0.055(8) C14A 0.123(14) 0.092(11) 0.073(10) -0.022(9) -0.003(10) -0.033(10) C15A 0.098(15) 0.119(12) 0.065(11) 0.011(9) -0.025(11) -0.013(9) C16A 0.110(17) 0.109(10) 0.076(15) 0.021(10) -0.015(12) -0.007(9) C23 0.065(5) 0.099(6) 0.095(7) 0.019(5) 0.011(5) -0.010(5) C24 0.080(7) 0.130(8) 0.110(8) 0.004(6) 0.022(6) 0.002(6) _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 Al1 O1 1.796(5) . ? Al1 C17 1.963(15) . ? Al1 C19 1.976(13) . ? Al1 N3 1.945(6) . ? Al1 C19B 1.95(2) . ? Al1 C17A 1.957(15) . ? Al1 C19A 1.97(2) . ? Al2 N5 1.882(6) . ? Al2 C21 1.94(2) . ? Al2 C21A 1.966(10) . ? Al2 N1 1.965(6) . ? Al2 C23 1.971(9) . ? N1 C3 1.354(8) . ? N1 N2 1.370(7) . ? N2 C1 1.359(8) . ? N2 C11 1.412(8) . ? N3 C8 1.331(8) . ? N3 N4 1.388(7) . ? N4 C6 1.357(8) . ? N4 C11 1.417(7) . ? N5 C12 1.336(8) . ? N5 C13 1.510(18) . ? N5 C13A 1.565(16) . ? O1 C12 1.343(8) . ? C1 C2 1.379(10) . ? C1 C4 1.499(9) . ? C2 C3 1.387(11) . ? C3 C5 1.500(11) . ? C6 C7 1.384(9) . ? C6 C9 1.492(9) . ? C7 C8 1.378(10) . ? C8 C10 1.494(10) . ? C11 C12 1.397(9) . ? C13 C14 1.421(19) . ? C13 C15 1.43(2) . ? C15 C16 1.53(3) . ? C13A C14A 1.527(19) . ? C13A C15A 1.52(2) . ? C15A C16A 1.52(2) . ? C17 C18 1.538(17) . ? C17A C18A 1.547(18) . ? C19 C20 1.549(19) . ? C19A C20A 1.54(2) . ? C19B C20B 1.52(2) . ? C21 C22 1.447(19) . ? C21A C22A 1.325(13) . ? C23 C24 1.540(10) . ? 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 O1 Al1 C17 109.3(9) . . ? O1 Al1 C19 108.6(14) . . ? C17 Al1 C19 121.3(18) . . ? O1 Al1 N3 94.5(2) . . ? C17 Al1 N3 112.2(7) . . ? C19 Al1 N3 107.5(10) . . ? O1 Al1 C19B 111.5(16) . . ? C17 Al1 C19B 107.2(13) . . ? C19 Al1 C19B 15.3(14) . . ? N3 Al1 C19B 121(2) . . ? O1 Al1 C17A 115.8(10) . . ? C17 Al1 C17A 8.6(15) . . ? C19 Al1 C17A 121.2(19) . . ? N3 Al1 C17A 105.3(7) . . ? C19B Al1 C17A 108.2(13) . . ? O1 Al1 C19A 101.8(19) . . ? C17 Al1 C19A 123(4) . . ? C19 Al1 C19A 7(2) . . ? N3 Al1 C19A 111(3) . . ? C19B Al1 C19A 16(4) . . ? C17A Al1 C19A 124(4) . . ? N5 Al2 C21 122.8(9) . . ? N5 Al2 C21A 113.5(5) . . ? C21 Al2 C21A 16.0(12) . . ? N5 Al2 N1 95.5(3) . . ? C21 Al2 N1 117.1(11) . . ? C21A Al2 N1 108.2(5) . . ? N5 Al2 C23 113.6(3) . . ? C21 Al2 C23 101.3(11) . . ? C21A Al2 C23 117.2(5) . . ? N1 Al2 C23 106.1(3) . . ? C3 N1 N2 105.2(6) . . ? C3 N1 Al2 135.6(6) . . ? N2 N1 Al2 116.6(4) . . ? C1 N2 N1 111.5(5) . . ? C1 N2 C11 128.1(6) . . ? N1 N2 C11 120.2(6) . . ? C8 N3 N4 105.7(6) . . ? C8 N3 Al1 135.8(5) . . ? N4 N3 Al1 114.1(4) . . ? C6 N4 N3 109.9(5) . . ? C6 N4 C11 129.0(6) . . ? N3 N4 C11 120.9(6) . . ? C12 N5 C13 107.8(16) . . ? C12 N5 C13A 120.8(14) . . ? C13 N5 C13A 13(3) . . ? C12 N5 Al2 118.4(5) . . ? C13 N5 Al2 132.5(15) . . ? C13A N5 Al2 120.2(13) . . ? C12 O1 Al1 117.8(4) . . ? N2 C1 C2 106.1(7) . . ? N2 C1 C4 122.7(7) . . ? C2 C1 C4 131.1(8) . . ? C1 C2 C3 107.1(8) . . ? N1 C3 C2 110.0(7) . . ? N1 C3 C5 120.9(8) . . ? C2 C3 C5 129.1(8) . . ? N4 C6 C7 107.0(7) . . ? N4 C6 C9 120.6(6) . . ? C7 C6 C9 132.4(7) . . ? C6 C7 C8 106.2(7) . . ? N3 C8 C7 111.1(7) . . ? N3 C8 C10 121.7(7) . . ? C7 C8 C10 127.2(7) . . ? C12 C11 N4 120.4(6) . . ? C12 C11 N2 123.6(6) . . ? N4 C11 N2 115.9(6) . . ? N5 C12 O1 122.0(6) . . ? N5 C12 C11 119.9(7) . . ? O1 C12 C11 117.9(6) . . ? C14 C13 C15 123(2) . . ? C14 C13 N5 116.2(17) . . ? C15 C13 N5 109(2) . . ? C13 C15 C16 103(3) . . ? C14A C13A C15A 138.1(16) . . ? C14A C13A N5 113.0(14) . . ? C15A C13A N5 108.0(15) . . ? C16A C15A C13A 122(2) . . ? C18 C17 Al1 111.1(14) . . ? C18A C17A Al1 120.6(15) . . ? C20 C19 Al1 105.1(14) . . ? C20A C19A Al1 117(2) . . ? C20B C19B Al1 108(2) . . ? C22 C21 Al2 132(2) . . ? C22A C21A Al2 124.0(10) . . ? C24 C23 Al2 114.9(6) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.216 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 933659' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_8 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C28 H43 Al2 N5 O' _chemical_formula_sum 'C28 H43 Al2 N5 O' _chemical_formula_weight 519.63 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.510(3) _cell_length_b 19.539(9) _cell_length_c 20.952(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3074(2) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 1671 _cell_measurement_theta_min 2.206 _cell_measurement_theta_max 17.996 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.123 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9748 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20610 _diffrn_reflns_av_R_equivalents 0.0761 _diffrn_reflns_av_unetI/netI 0.0741 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5418 _reflns_number_gt 3597 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX v1.70 (Farrugia, 1999)' _computing_publication_material 'WINGX v1.70 (Farrugia, 1999)' _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. The complexe show disorder in a ethyl group. DFIX instruction of SHELX has been used to restrain the distances between these atoms. ; _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^)+(0.0513P)^2^+0.1781P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 5418 _refine_ls_number_parameters 332 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0952 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1246 _refine_ls_wR_factor_gt 0.1087 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 Al1 Al 0.16888(14) 0.92906(5) 0.14410(5) 0.0451(3) Uani 1 1 d . . . Al2 Al 0.39282(15) 0.82024(6) 0.37011(5) 0.0523(3) Uani 1 1 d D . . N1 N 0.4920(4) 0.94527(15) 0.31042(13) 0.0445(7) Uani 1 1 d . . . N2 N 0.5151(4) 0.90851(15) 0.36598(14) 0.0473(7) Uani 1 1 d . A . N3 N 0.2442(4) 0.99960(14) 0.25957(13) 0.0423(7) Uani 1 1 d . . . N4 N 0.1937(4) 1.01256(14) 0.19752(13) 0.0447(7) Uani 1 1 d . A . N5 N 0.1350(4) 0.87021(13) 0.21463(13) 0.0436(7) Uani 1 1 d . A . O1 O 0.3263(3) 0.81974(12) 0.28832(11) 0.0538(7) Uani 1 1 d . A . C1 C 0.6658(5) 0.9330(2) 0.39272(17) 0.0510(9) Uani 1 1 d . . . C2 C 0.7348(5) 0.9840(2) 0.3556(2) 0.0622(11) Uani 1 1 d . A . H2 H 0.8367 1.0095 0.3641 0.075 Uiso 1 1 calc R . . C3 C 0.6251(5) 0.99069(19) 0.30329(19) 0.0533(10) Uani 1 1 d . A . C4 C 0.7284(6) 0.9035(2) 0.45512(19) 0.0728(13) Uani 1 1 d . A . H4A H 0.7695 0.8575 0.4485 0.109 Uiso 1 1 calc R . . H4B H 0.6316 0.9032 0.4851 0.109 Uiso 1 1 calc R . . H4C H 0.8240 0.9308 0.4717 0.109 Uiso 1 1 calc R . . C5 C 0.6385(6) 1.0366(2) 0.2473(2) 0.0832(14) Uani 1 1 d . . . H5A H 0.6062 1.0120 0.2095 0.125 Uiso 1 1 calc R A . H5B H 0.7586 1.0530 0.2434 0.125 Uiso 1 1 calc R . . H5C H 0.5594 1.0748 0.2529 0.125 Uiso 1 1 calc R . . C6 C 0.2043(5) 1.05273(19) 0.29751(19) 0.0532(10) Uani 1 1 d . A . C7 C 0.1283(5) 1.1014(2) 0.2602(2) 0.0623(12) Uani 1 1 d . . . H7 H 0.0885 1.1441 0.2736 0.075 Uiso 1 1 calc R A . C8 C 0.1206(5) 1.07591(19) 0.19856(19) 0.0537(10) Uani 1 1 d . A . C9 C 0.2395(6) 1.0504(2) 0.36801(18) 0.0717(13) Uani 1 1 d . . . H9A H 0.2218 1.0046 0.3834 0.107 Uiso 1 1 calc R A . H9B H 0.1592 1.0809 0.3896 0.107 Uiso 1 1 calc R . . H9C H 0.3600 1.0643 0.3762 0.107 Uiso 1 1 calc R . . C10 C 0.0483(6) 1.1076(2) 0.1393(2) 0.0796(14) Uani 1 1 d . . . H10A H 0.1053 1.0877 0.1028 0.119 Uiso 1 1 calc R A . H10B H 0.0706 1.1560 0.1400 0.119 Uiso 1 1 calc R . . H10C H -0.0777 1.0996 0.1370 0.119 Uiso 1 1 calc R . . C11 C 0.3333(5) 0.93737(17) 0.27470(16) 0.0437(9) Uani 1 1 d . A . C12 C 0.2633(5) 0.8750(2) 0.25973(17) 0.0448(9) Uani 1 1 d . . . C13 C 0.0172(5) 0.80982(19) 0.21671(17) 0.0538(10) Uani 1 1 d . . . H13 H 0.0543 0.7820 0.2533 0.065 Uiso 1 1 calc R A . C14 C -0.1727(5) 0.8327(2) 0.2292(2) 0.0779(13) Uani 1 1 d . A . H14A H -0.2117 0.8620 0.1951 0.117 Uiso 1 1 calc R . . H14B H -0.1776 0.8574 0.2688 0.117 Uiso 1 1 calc R . . H14C H -0.2490 0.7934 0.2316 0.117 Uiso 1 1 calc R . . C15 C 0.0426(6) 0.76689(19) 0.15774(18) 0.0547(11) Uani 1 1 d . A . C16 C -0.0898(7) 0.7532(2) 0.1138(2) 0.0770(14) Uani 1 1 d . . . H16 H -0.2031 0.7709 0.1206 0.092 Uiso 1 1 calc R A . C17 C -0.0587(10) 0.7137(3) 0.0600(3) 0.0960(18) Uani 1 1 d . A . H17 H -0.1495 0.7058 0.0307 0.115 Uiso 1 1 calc R . . C18 C 0.1054(12) 0.6867(3) 0.0505(3) 0.110(2) Uani 1 1 d . . . H18 H 0.1265 0.6599 0.0146 0.132 Uiso 1 1 calc R A . C19 C 0.2404(9) 0.6984(3) 0.0928(3) 0.110(2) Uani 1 1 d . A . H19 H 0.3526 0.6795 0.0863 0.131 Uiso 1 1 calc R . . C20 C 0.2066(7) 0.7391(2) 0.1458(2) 0.0839(15) Uani 1 1 d . . . H20 H 0.2989 0.7478 0.1743 0.101 Uiso 1 1 calc R A . C21 C -0.0389(5) 0.9384(2) 0.08773(17) 0.0606(11) Uani 1 1 d . . . H21A H -0.1244 0.9032 0.0991 0.073 Uiso 1 1 calc R . . H21B H -0.0943 0.9823 0.0962 0.073 Uiso 1 1 calc R . . C22 C -0.0043(7) 0.9336(3) 0.01883(19) 0.110(2) Uani 1 1 d . . . H22A H 0.0705 0.9709 0.0059 0.166 Uiso 1 1 calc R . . H22B H -0.1150 0.9357 -0.0040 0.166 Uiso 1 1 calc R . . H22C H 0.0542 0.8911 0.0096 0.166 Uiso 1 1 calc R . . C23 C 0.4000(5) 0.9146(2) 0.10239(17) 0.0586(11) Uani 1 1 d . . . H23A H 0.4888 0.9063 0.1351 0.070 Uiso 1 1 calc R . . H23B H 0.3924 0.8736 0.0764 0.070 Uiso 1 1 calc R . . C24 C 0.4644(6) 0.9733(2) 0.0603(2) 0.0746(13) Uani 1 1 d . . . H24A H 0.3844 0.9789 0.0250 0.112 Uiso 1 1 calc R . . H24B H 0.5816 0.9632 0.0447 0.112 Uiso 1 1 calc R . . H24C H 0.4676 1.0148 0.0849 0.112 Uiso 1 1 calc R . . C25 C 0.5589(6) 0.7444(2) 0.3813(2) 0.0679(12) Uani 1 1 d . A . H25A H 0.6633 0.7520 0.3550 0.081 Uiso 1 1 calc R . . H25B H 0.5971 0.7426 0.4255 0.081 Uiso 1 1 calc R . . C26 C 0.4768(7) 0.6785(3) 0.3638(3) 0.131(2) Uani 1 1 d . . . H26A H 0.3669 0.6730 0.3866 0.196 Uiso 1 1 calc R A . H26B H 0.5563 0.6418 0.3745 0.196 Uiso 1 1 calc R . . H26C H 0.4536 0.6778 0.3187 0.196 Uiso 1 1 calc R . . C27 C 0.1760(16) 0.8341(6) 0.4181(5) 0.079(5) Uiso 0.50 1 d PD A 1 H27A H 0.1002 0.8664 0.3959 0.095 Uiso 0.50 1 calc PR A 1 H27B H 0.1121 0.7911 0.4217 0.095 Uiso 0.50 1 calc PR A 1 C28 C 0.2169(15) 0.8600(6) 0.4815(5) 0.100(3) Uiso 0.50 1 d PD A 1 H28A H 0.1081 0.8674 0.5046 0.150 Uiso 0.50 1 calc PR A 1 H28B H 0.2805 0.9025 0.4779 0.150 Uiso 0.50 1 calc PR A 1 H28C H 0.2889 0.8273 0.5039 0.150 Uiso 0.50 1 calc PR A 1 C28A C 0.0730(11) 0.7724(4) 0.4351(4) 0.065(2) Uiso 0.50 1 d PD A 2 H28D H -0.0104 0.7803 0.4691 0.097 Uiso 0.50 1 calc PR A 2 H28E H 0.1298 0.7289 0.4412 0.097 Uiso 0.50 1 calc PR A 2 H28F H 0.0112 0.7725 0.3950 0.097 Uiso 0.50 1 calc PR A 2 C27A C 0.2059(15) 0.8259(6) 0.4352(6) 0.064(4) Uiso 0.50 1 d P A 2 H27C H 0.2627 0.8263 0.4767 0.077 Uiso 0.50 1 calc PR A 2 H27D H 0.1453 0.8694 0.4302 0.077 Uiso 0.50 1 calc PR A 2 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 Al1 0.0459(6) 0.0470(7) 0.0424(6) 0.0015(5) -0.0014(5) 0.0024(5) Al2 0.0522(7) 0.0509(7) 0.0538(7) 0.0074(6) -0.0022(6) 0.0031(6) N1 0.0449(19) 0.0449(19) 0.0437(17) 0.0002(14) -0.0019(15) -0.0007(15) N2 0.0453(18) 0.0515(19) 0.0451(18) -0.0025(15) -0.0032(16) 0.0049(14) N3 0.0413(17) 0.0369(18) 0.0487(18) -0.0025(15) -0.0039(15) -0.0004(14) N4 0.0438(18) 0.0451(19) 0.0451(17) 0.0074(14) -0.0045(15) -0.0013(14) N5 0.0501(19) 0.0356(17) 0.0450(17) -0.0023(14) -0.0036(15) -0.0050(14) O1 0.0620(16) 0.0379(14) 0.0614(16) 0.0048(13) -0.0143(13) 0.0028(13) C1 0.044(2) 0.058(3) 0.051(2) -0.009(2) -0.0068(19) 0.008(2) C2 0.043(2) 0.070(3) 0.074(3) -0.005(2) -0.005(2) -0.010(2) C3 0.044(2) 0.055(2) 0.060(2) 0.005(2) 0.001(2) -0.0054(19) C4 0.069(3) 0.086(4) 0.064(3) 0.000(2) -0.019(2) 0.003(2) C5 0.063(3) 0.099(4) 0.087(3) 0.023(3) 0.001(3) -0.028(3) C6 0.054(3) 0.044(2) 0.061(3) -0.014(2) -0.002(2) -0.0006(19) C7 0.061(3) 0.038(2) 0.088(3) -0.012(2) -0.004(2) 0.009(2) C8 0.045(2) 0.039(2) 0.077(3) 0.008(2) -0.007(2) 0.0044(19) C9 0.069(3) 0.079(3) 0.067(3) -0.027(2) -0.001(2) 0.012(2) C10 0.076(3) 0.058(3) 0.106(4) 0.025(3) -0.018(3) 0.003(2) C11 0.043(2) 0.040(2) 0.048(2) -0.0009(18) -0.0129(18) -0.0009(18) C12 0.047(2) 0.047(2) 0.041(2) -0.0001(18) -0.0028(18) 0.0025(19) C13 0.061(3) 0.051(3) 0.049(2) 0.007(2) -0.007(2) -0.013(2) C14 0.059(3) 0.089(3) 0.086(3) -0.003(3) 0.010(2) -0.012(3) C15 0.073(3) 0.038(2) 0.053(3) 0.0065(19) -0.006(2) -0.019(2) C16 0.107(4) 0.052(3) 0.072(3) 0.003(2) -0.017(3) -0.021(2) C17 0.140(6) 0.075(4) 0.073(4) -0.005(3) -0.027(4) -0.036(4) C18 0.167(7) 0.072(4) 0.090(4) -0.024(3) 0.011(5) -0.040(5) C19 0.124(5) 0.086(4) 0.119(5) -0.044(4) 0.025(4) -0.012(3) C20 0.094(4) 0.066(3) 0.091(4) -0.023(3) 0.002(3) -0.013(3) C21 0.063(3) 0.065(3) 0.054(2) 0.003(2) -0.013(2) 0.003(2) C22 0.091(4) 0.180(6) 0.061(3) -0.002(4) -0.019(3) -0.004(4) C23 0.060(3) 0.062(3) 0.054(2) 0.001(2) 0.006(2) 0.006(2) C24 0.064(3) 0.083(3) 0.077(3) 0.007(3) 0.015(2) -0.009(2) C25 0.074(3) 0.056(3) 0.074(3) 0.012(2) -0.014(2) 0.006(2) C26 0.104(4) 0.065(3) 0.224(7) -0.025(4) -0.045(5) 0.018(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 Al1 N5 1.889(3) . ? Al1 C23 1.964(4) . ? Al1 C21 1.966(4) . ? Al1 N4 1.987(3) . ? Al2 O1 1.785(3) . ? Al2 C27 1.933(12) . ? Al2 C25 1.951(4) . ? Al2 N2 1.956(3) . ? Al2 C27A 1.960(11) . ? N1 C3 1.345(4) . ? N1 N2 1.379(4) . ? N1 C11 1.415(4) . ? N2 C1 1.351(4) . ? N3 C6 1.342(4) . ? N3 N4 1.378(4) . ? N3 C11 1.423(4) . ? N4 C8 1.354(4) . ? N5 C12 1.352(4) . ? N5 C13 1.476(4) . ? O1 C12 1.322(4) . ? C1 C2 1.365(5) . ? C1 C4 1.504(5) . ? C2 C3 1.378(5) . ? C3 C5 1.480(5) . ? C6 C7 1.356(5) . ? C6 C9 1.501(5) . ? C7 C8 1.386(5) . ? C8 C10 1.490(5) . ? C11 C12 1.365(5) . ? C13 C15 1.506(5) . ? C13 C14 1.518(5) . ? C15 C20 1.369(6) . ? C15 C16 1.380(6) . ? C16 C17 1.387(7) . ? C17 C18 1.355(8) . ? C18 C19 1.366(8) . ? C19 C20 1.389(6) . ? C21 C22 1.470(5) . ? C23 C24 1.526(5) . ? C25 C26 1.474(6) . ? C27 C28 1.454(12) . ? C28A C27A 1.445(13) . ? 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 N5 Al1 C23 112.28(15) . . ? N5 Al1 C21 114.81(16) . . ? C23 Al1 C21 116.60(17) . . ? N5 Al1 N4 94.12(12) . . ? C23 Al1 N4 106.62(15) . . ? C21 Al1 N4 109.67(15) . . ? O1 Al2 C27 105.4(4) . . ? O1 Al2 C25 106.87(16) . . ? C27 Al2 C25 125.6(4) . . ? O1 Al2 N2 95.38(12) . . ? C27 Al2 N2 107.1(3) . . ? C25 Al2 N2 112.04(16) . . ? O1 Al2 C27A 117.9(4) . . ? C27 Al2 C27A 13.3(5) . . ? C25 Al2 C27A 114.6(4) . . ? N2 Al2 C27A 108.5(3) . . ? C3 N1 N2 110.1(3) . . ? C3 N1 C11 129.7(3) . . ? N2 N1 C11 119.7(3) . . ? C1 N2 N1 105.7(3) . . ? C1 N2 Al2 133.5(3) . . ? N1 N2 Al2 115.9(2) . . ? C6 N3 N4 110.8(3) . . ? C6 N3 C11 129.4(3) . . ? N4 N3 C11 119.8(3) . . ? C8 N4 N3 105.3(3) . . ? C8 N4 Al1 136.2(3) . . ? N3 N4 Al1 114.0(2) . . ? C12 N5 C13 117.5(3) . . ? C12 N5 Al1 114.1(2) . . ? C13 N5 Al1 126.2(2) . . ? C12 O1 Al2 122.1(2) . . ? N2 C1 C2 109.9(3) . . ? N2 C1 C4 119.1(4) . . ? C2 C1 C4 131.0(4) . . ? C1 C2 C3 107.2(3) . . ? N1 C3 C2 107.1(3) . . ? N1 C3 C5 122.6(4) . . ? C2 C3 C5 130.3(4) . . ? N3 C6 C7 107.2(3) . . ? N3 C6 C9 121.3(3) . . ? C7 C6 C9 131.4(4) . . ? C6 C7 C8 107.6(3) . . ? N4 C8 C7 109.1(3) . . ? N4 C8 C10 121.0(4) . . ? C7 C8 C10 130.0(4) . . ? C12 C11 N1 122.9(3) . . ? C12 C11 N3 122.1(3) . . ? N1 C11 N3 114.8(3) . . ? O1 C12 N5 121.1(3) . . ? O1 C12 C11 119.1(3) . . ? N5 C12 C11 119.8(3) . . ? N5 C13 C15 110.2(3) . . ? N5 C13 C14 109.4(3) . . ? C15 C13 C14 115.2(3) . . ? C20 C15 C16 116.7(4) . . ? C20 C15 C13 119.0(4) . . ? C16 C15 C13 124.3(4) . . ? C15 C16 C17 122.0(5) . . ? C18 C17 C16 119.2(6) . . ? C17 C18 C19 121.0(6) . . ? C18 C19 C20 118.6(6) . . ? C15 C20 C19 122.5(5) . . ? C22 C21 Al1 116.3(3) . . ? C24 C23 Al1 115.4(3) . . ? C26 C25 Al2 111.5(3) . . ? C28 C27 Al2 110.3(8) . . ? C28A C27A Al2 116.9(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.196 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.037 _database_code_depnum_ccdc_archive 'CCDC 933660' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_13 # start Validation Reply Form _vrf_THETM01_13 ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.4812 RESPONSE: The crystals show decomposition during the experiment and despite several crystals are measurements, the spectra of them resulting very poor. We believe that the crystal structure determination described in this manuscript is the best which is possible to obtaim. ; # end Validation Reply Form _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H44 Al3 N5 O' _chemical_formula_sum 'C23 H44 Al3 N5 O' _chemical_formula_weight 487.57 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' Al Al 0.0645 0.0514 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.725(8) _cell_length_b 34.833(5) _cell_length_c 10.122(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.839(19) _cell_angle_gamma 90.00 _cell_volume 3343(4) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 646 _cell_measurement_theta_min 2.145 _cell_measurement_theta_max 17.215 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.969 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9464 _exptl_absorpt_correction_T_max 0.9638 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6190 _diffrn_reflns_av_R_equivalents 0.0622 _diffrn_reflns_av_unetI/netI 0.0853 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 20.00 _reflns_number_total 2961 _reflns_number_gt 1823 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX v1.70 (Farrugia, 1999)' _computing_publication_material 'WINGX v1.70 (Farrugia, 1999)' _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. The compound crystallise with some molecules of toluene solvent which were found heavily disordered. An investigation of the void space in the structure show two principal voids of about 252 A3 in the unit cell. The option squeeze in Platon (Spek, A. L. Acta Crystallogr. 1990, A46, C-34) was used to eliminate the contribution of the electron density in the solvent region from the intensity data. The derived quantities (Mr, F(000), and Dx in the Crystal data are corrected with the contribution from this disordered solvent. ; # SQUEEZE RESULTS (APPEND TO CIF) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.000 0.500 0.500 252 49 ' ' 2 0.500 0.000 0.000 252 49 ' ' _platon_squeeze_details ? _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^)+(0.0912P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2961 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_ref 0.1676 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_restrained_S_all 0.952 _refine_ls_shift/su_max 0.009 _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 Al1 Al 0.21312(16) 0.12936(5) 0.43769(19) 0.0620(6) Uani 1 1 d . . . Al2 Al -0.20676(16) 0.17303(5) 0.68721(19) 0.0633(6) Uani 1 1 d . . . Al3 Al -0.10230(18) 0.08617(5) 0.3192(2) 0.0710(7) Uani 1 1 d . . . N1 N 0.2531(4) 0.09502(13) 0.5929(5) 0.0542(13) Uani 1 1 d . . . N2 N 0.1558(4) 0.09818(13) 0.6762(5) 0.0517(12) Uani 1 1 d . . . N3 N -0.0295(4) 0.16974(12) 0.8241(5) 0.0547(13) Uani 1 1 d . . . N4 N 0.0887(5) 0.15323(12) 0.7867(5) 0.0547(12) Uani 1 1 d . . . N5 N -0.1192(4) 0.16843(12) 0.5349(5) 0.0576(13) Uani 1 1 d . . . O1 O 0.0153(3) 0.12588(9) 0.4291(4) 0.0544(10) Uani 1 1 d . . . C1 C 0.1608(6) 0.06743(18) 0.7580(6) 0.0575(16) Uani 1 1 d . . . C2 C 0.2639(6) 0.04358(16) 0.7290(7) 0.0678(18) Uani 1 1 d . . . H2 H 0.2927 0.0202 0.7707 0.081 Uiso 1 1 calc R . . C3 C 0.3165(5) 0.06061(18) 0.6268(7) 0.0581(16) Uani 1 1 d . . . C4 C 0.0678(6) 0.06393(16) 0.8570(6) 0.082(2) Uani 1 1 d . . . H4A H 0.1019 0.0806 0.9329 0.123 Uiso 1 1 calc R . . H4B H 0.0685 0.0379 0.8879 0.123 Uiso 1 1 calc R . . H4C H -0.0268 0.0711 0.8137 0.123 Uiso 1 1 calc R . . C5 C 0.4255(6) 0.04556(15) 0.5540(7) 0.082(2) Uani 1 1 d . . . H5A H 0.3789 0.0339 0.4700 0.122 Uiso 1 1 calc R . . H5B H 0.4836 0.0268 0.6097 0.122 Uiso 1 1 calc R . . H5C H 0.4833 0.0664 0.5359 0.122 Uiso 1 1 calc R . . C6 C 0.2070(6) 0.16031(16) 0.8842(7) 0.0633(17) Uani 1 1 d . . . C7 C 0.1657(6) 0.18106(16) 0.9867(7) 0.0679(18) Uani 1 1 d . . . H7 H 0.2236 0.1894 1.0674 0.081 Uiso 1 1 calc R . . C8 C 0.0193(6) 0.18688(15) 0.9443(7) 0.0598(16) Uani 1 1 d . . . C9 C 0.3536(5) 0.14704(18) 0.8749(7) 0.093(2) Uani 1 1 d . . . H9A H 0.3580 0.1195 0.8793 0.139 Uiso 1 1 calc R . . H9B H 0.4222 0.1577 0.9489 0.139 Uiso 1 1 calc R . . H9C H 0.3731 0.1556 0.7907 0.139 Uiso 1 1 calc R . . C10 C -0.0765(6) 0.20853(16) 1.0171(6) 0.0772(19) Uani 1 1 d . . . H10A H -0.0911 0.2341 0.9811 0.116 Uiso 1 1 calc R . . H10B H -0.0337 0.2098 1.1121 0.116 Uiso 1 1 calc R . . H10C H -0.1655 0.1955 1.0043 0.116 Uiso 1 1 calc R . . C11 C 0.0714(5) 0.13191(15) 0.6655(6) 0.0475(14) Uani 1 1 d . . . C12 C -0.0140(5) 0.14241(16) 0.5456(7) 0.0523(15) Uani 1 1 d . . . C13 C -0.1683(5) 0.18970(18) 0.4037(6) 0.0689(18) Uani 1 1 d . . . H13 H -0.1315 0.1761 0.3341 0.083 Uiso 1 1 calc R . . C14 C -0.1075(7) 0.23060(17) 0.4144(7) 0.097(2) Uani 1 1 d . . . H14A H -0.1348 0.2439 0.4877 0.146 Uiso 1 1 calc R . . H14B H -0.1434 0.2441 0.3312 0.146 Uiso 1 1 calc R . . H14C H -0.0065 0.2294 0.4310 0.146 Uiso 1 1 calc R . . C15 C -0.3305(6) 0.1881(2) 0.3623(8) 0.104(2) Uani 1 1 d . . . H15A H -0.3602 0.1615 0.3602 0.125 Uiso 1 1 calc R . . H15B H -0.3689 0.2011 0.4308 0.125 Uiso 1 1 calc R . . C16 C -0.3915(8) 0.2060(3) 0.2266(11) 0.187(5) Uani 1 1 d . . . H16A H -0.3578 0.2319 0.2256 0.281 Uiso 1 1 calc R . . H16B H -0.4925 0.2061 0.2110 0.281 Uiso 1 1 calc R . . H16C H -0.3630 0.1914 0.1568 0.281 Uiso 1 1 calc R . . C17 C -0.2617(7) 0.0769(2) 0.4047(8) 0.116(3) Uani 1 1 d . . . H17A H -0.2273 0.0735 0.5005 0.173 Uiso 1 1 calc R . . H17B H -0.3112 0.0542 0.3669 0.173 Uiso 1 1 calc R . . H17C H -0.3247 0.0985 0.3887 0.173 Uiso 1 1 calc R . . C18 C -0.1415(7) 0.1097(2) 0.1387(7) 0.106(2) Uani 1 1 d . . . H18A H -0.1608 0.0899 0.0710 0.160 Uiso 1 1 calc R . . H18B H -0.0611 0.1243 0.1279 0.160 Uiso 1 1 calc R . . H18C H -0.2219 0.1263 0.1289 0.160 Uiso 1 1 calc R . . C19 C 0.0196(7) 0.04015(16) 0.3358(8) 0.115(3) Uani 1 1 d . . . H19A H 0.0505 0.0334 0.4297 0.173 Uiso 1 1 calc R . . H19B H 0.1002 0.0456 0.2987 0.173 Uiso 1 1 calc R . . H19C H -0.0326 0.0192 0.2872 0.173 Uiso 1 1 calc R . . C20 C 0.2688(6) 0.10896(18) 0.2760(6) 0.086(2) Uani 1 1 d . . . H20A H 0.2335 0.0833 0.2589 0.128 Uiso 1 1 calc R . . H20B H 0.3698 0.1087 0.2909 0.128 Uiso 1 1 calc R . . H20C H 0.2304 0.1249 0.1994 0.128 Uiso 1 1 calc R . . C21 C 0.2781(6) 0.18135(15) 0.4860(7) 0.085(2) Uani 1 1 d . . . H21A H 0.2408 0.1983 0.4121 0.128 Uiso 1 1 calc R . . H21B H 0.3792 0.1820 0.5049 0.128 Uiso 1 1 calc R . . H21C H 0.2462 0.1894 0.5649 0.128 Uiso 1 1 calc R . . C22 C -0.2884(7) 0.22410(18) 0.7087(7) 0.105(2) Uani 1 1 d . . . H22A H -0.2137 0.2422 0.7397 0.158 Uiso 1 1 calc R . . H22B H -0.3466 0.2224 0.7736 0.158 Uiso 1 1 calc R . . H22C H -0.3444 0.2324 0.6231 0.158 Uiso 1 1 calc R . . C23 C -0.3206(5) 0.12929(17) 0.7169(7) 0.087(2) Uani 1 1 d . . . H23A H -0.4091 0.1298 0.6519 0.130 Uiso 1 1 calc R . . H23B H -0.3374 0.1305 0.8067 0.130 Uiso 1 1 calc R . . H23C H -0.2716 0.1059 0.7066 0.130 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 Al1 0.0512(10) 0.0582(12) 0.0820(15) 0.0039(10) 0.0266(9) 0.0026(9) Al2 0.0473(10) 0.0689(13) 0.0757(15) -0.0023(10) 0.0178(9) 0.0089(9) Al3 0.0671(12) 0.0724(13) 0.0766(15) -0.0152(11) 0.0224(10) -0.0179(10) N1 0.044(3) 0.048(3) 0.072(4) -0.003(3) 0.016(3) 0.004(2) N2 0.047(3) 0.045(3) 0.067(4) 0.005(3) 0.020(3) 0.008(3) N3 0.049(3) 0.051(3) 0.069(4) -0.015(3) 0.023(3) 0.004(2) N4 0.049(3) 0.057(3) 0.057(4) -0.010(3) 0.009(3) -0.003(3) N5 0.042(3) 0.062(3) 0.069(4) 0.004(3) 0.011(2) 0.015(3) O1 0.051(2) 0.058(2) 0.058(3) -0.007(2) 0.0184(19) 0.0009(18) C1 0.052(4) 0.056(4) 0.067(5) 0.001(4) 0.018(3) 0.001(3) C2 0.052(4) 0.057(4) 0.092(6) 0.008(4) 0.011(4) 0.018(3) C3 0.048(3) 0.053(4) 0.074(5) -0.015(4) 0.016(3) -0.002(3) C4 0.083(4) 0.078(4) 0.092(6) 0.014(4) 0.033(4) 0.010(4) C5 0.068(4) 0.067(4) 0.117(6) 0.002(4) 0.037(4) 0.026(3) C6 0.062(4) 0.054(4) 0.074(5) -0.012(4) 0.016(4) 0.001(3) C7 0.062(4) 0.062(4) 0.077(5) -0.009(4) 0.011(4) -0.006(3) C8 0.071(5) 0.047(4) 0.071(5) -0.007(4) 0.036(4) -0.004(3) C9 0.038(3) 0.117(5) 0.116(6) -0.031(5) 0.001(3) 0.008(4) C10 0.081(4) 0.081(4) 0.078(5) -0.021(4) 0.035(4) -0.008(4) C11 0.039(3) 0.049(4) 0.054(4) -0.016(4) 0.010(3) 0.007(3) C12 0.039(3) 0.057(4) 0.062(5) -0.008(4) 0.015(4) -0.005(3) C13 0.050(4) 0.086(5) 0.072(5) 0.010(4) 0.015(3) 0.026(4) C14 0.113(5) 0.062(5) 0.125(7) 0.019(4) 0.043(5) 0.024(4) C15 0.071(5) 0.140(6) 0.093(6) 0.025(5) 0.001(4) 0.029(4) C16 0.111(7) 0.277(13) 0.167(11) 0.027(10) 0.014(7) 0.057(8) C17 0.100(5) 0.116(6) 0.147(7) -0.036(5) 0.062(5) -0.041(5) C18 0.117(5) 0.112(5) 0.087(6) -0.018(5) 0.016(4) -0.039(5) C19 0.125(6) 0.068(5) 0.156(8) -0.023(5) 0.040(6) -0.019(4) C20 0.080(4) 0.105(5) 0.079(5) 0.013(4) 0.034(4) 0.020(4) C21 0.065(4) 0.074(4) 0.120(6) 0.009(4) 0.026(4) -0.011(3) C22 0.109(5) 0.099(5) 0.109(6) -0.001(4) 0.026(5) 0.054(4) C23 0.059(4) 0.104(5) 0.102(6) -0.008(4) 0.026(4) -0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al1 O1 1.910(4) . ? Al1 C21 1.944(6) . ? Al1 N1 1.944(5) . ? Al1 C20 1.968(6) . ? Al2 N5 1.926(5) . ? Al2 C23 1.946(6) . ? Al2 N3 1.961(5) . ? Al2 C22 1.979(6) . ? Al3 C18 1.960(7) . ? Al3 C17 1.963(6) . ? Al3 O1 1.973(4) . ? Al3 C19 1.979(6) . ? N1 C3 1.357(6) . ? N1 N2 1.405(5) . ? N2 C1 1.348(6) . ? N2 C11 1.424(6) . ? N3 C8 1.343(7) . ? N3 N4 1.410(5) . ? N4 C6 1.362(7) . ? N4 C11 1.411(7) . ? N5 C12 1.353(6) . ? N5 C13 1.503(7) . ? O1 C12 1.398(6) . ? C1 C2 1.383(7) . ? C1 C4 1.497(7) . ? C2 C3 1.385(7) . ? C3 C5 1.513(7) . ? C6 C7 1.395(7) . ? C6 C9 1.521(7) . ? C7 C8 1.408(7) . ? C8 C10 1.511(7) . ? C11 C12 1.360(7) . ? C13 C14 1.537(7) . ? C13 C15 1.541(7) . ? C15 C16 1.505(10) . ? 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 O1 Al1 C21 109.8(2) . . ? O1 Al1 N1 90.94(17) . . ? C21 Al1 N1 112.0(3) . . ? O1 Al1 C20 113.6(2) . . ? C21 Al1 C20 114.3(3) . . ? N1 Al1 C20 114.0(2) . . ? N5 Al2 C23 115.2(2) . . ? N5 Al2 N3 94.9(2) . . ? C23 Al2 N3 106.6(2) . . ? N5 Al2 C22 115.0(3) . . ? C23 Al2 C22 115.5(3) . . ? N3 Al2 C22 106.6(3) . . ? C18 Al3 C17 118.0(3) . . ? C18 Al3 O1 101.6(2) . . ? C17 Al3 O1 106.4(2) . . ? C18 Al3 C19 114.0(3) . . ? C17 Al3 C19 110.3(3) . . ? O1 Al3 C19 105.0(2) . . ? C3 N1 N2 104.3(4) . . ? C3 N1 Al1 138.3(4) . . ? N2 N1 Al1 113.3(3) . . ? C1 N2 N1 111.7(4) . . ? C1 N2 C11 130.1(5) . . ? N1 N2 C11 118.3(5) . . ? C8 N3 N4 106.3(4) . . ? C8 N3 Al2 133.8(4) . . ? N4 N3 Al2 118.4(4) . . ? C6 N4 C11 130.1(5) . . ? C6 N4 N3 109.8(5) . . ? C11 N4 N3 120.1(4) . . ? C12 N5 C13 119.1(5) . . ? C12 N5 Al2 116.9(4) . . ? C13 N5 Al2 123.8(3) . . ? C12 O1 Al1 109.1(3) . . ? C12 O1 Al3 124.2(3) . . ? Al1 O1 Al3 121.48(19) . . ? N2 C1 C2 106.0(5) . . ? N2 C1 C4 122.1(5) . . ? C2 C1 C4 131.9(6) . . ? C1 C2 C3 107.9(5) . . ? N1 C3 C2 110.2(5) . . ? N1 C3 C5 120.7(6) . . ? C2 C3 C5 129.1(6) . . ? N4 C6 C7 107.2(5) . . ? N4 C6 C9 123.5(6) . . ? C7 C6 C9 129.2(6) . . ? C6 C7 C8 106.7(5) . . ? N3 C8 C7 110.0(5) . . ? N3 C8 C10 122.1(5) . . ? C7 C8 C10 127.9(6) . . ? C12 C11 N4 124.4(5) . . ? C12 C11 N2 121.1(5) . . ? N4 C11 N2 114.4(5) . . ? N5 C12 C11 123.5(5) . . ? N5 C12 O1 120.1(5) . . ? C11 C12 O1 116.3(5) . . ? N5 C13 C14 110.7(5) . . ? N5 C13 C15 109.1(5) . . ? C14 C13 C15 114.0(5) . . ? C16 C15 C13 113.9(6) . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 20.00 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.243 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 933661' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_16 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H58 Al3 N5 O, C7 H8' _chemical_formula_sum 'C41 H66 Al3 N5 O' _chemical_formula_weight 725.93 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' Al Al 0.0645 0.0514 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.4873(15) _cell_length_b 19.489(3) _cell_length_c 11.0006(15) _cell_angle_alpha 90.00 _cell_angle_beta 97.873(3) _cell_angle_gamma 90.00 _cell_volume 2227.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3319 _cell_measurement_theta_min 2.222 _cell_measurement_theta_max 20.073 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.082 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 0.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9696 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13614 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7599 _reflns_number_gt 5674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS, XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WINGX v1.70 (Farrugia, 1999)' _computing_publication_material 'WINGX v1.70 (Farrugia, 1999)' _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. The complexe show high disorder in the toluene solvent and ethyl groups. AFIX 66 for toluene, and DFIX instructions for ethyl groups have been used to restrain the distances between these atoms. ; _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^)+(0.0915P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(17) _chemical_absolute_configuration ad _refine_ls_number_reflns 7599 _refine_ls_number_parameters 444 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1579 _refine_ls_wR_factor_gt 0.1387 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.019 _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 Al1 Al 0.94050(10) 0.97437(6) 0.80326(9) 0.0523(3) Uani 1 1 d . . . Al2 Al 1.17030(11) 0.89482(6) 1.21915(9) 0.0562(3) Uani 1 1 d . . . Al3 Al 1.39588(13) 0.87056(6) 1.02700(11) 0.0652(3) Uani 1 1 d . B . N5 N 1.0514(3) 0.91010(13) 0.8972(2) 0.0472(7) Uani 1 1 d . . . N4 N 1.2033(3) 1.02303(14) 0.8185(2) 0.0469(7) Uani 1 1 d . . . N3 N 1.0774(3) 1.03932(14) 0.7753(3) 0.0511(7) Uani 1 1 d . . . N2 N 1.3388(3) 1.01078(14) 1.0113(3) 0.0492(7) Uani 1 1 d . . . N1 N 1.4409(3) 0.96837(18) 1.0499(3) 0.0574(8) Uani 1 1 d . . . O1 O 1.2259(2) 0.89023(11) 1.05399(19) 0.0495(6) Uani 1 1 d . . . C1 C 1.5275(4) 1.0083(3) 1.1203(3) 0.0648(11) Uani 1 1 d . . . C2 C 1.4829(4) 1.0742(3) 1.1213(4) 0.0686(11) Uani 1 1 d . . . H2 H 1.5261 1.1115 1.1603 0.082 Uiso 1 1 calc R . . C3 C 1.3627(4) 1.0751(2) 1.0543(3) 0.0574(9) Uani 1 1 d . . . C4 C 1.6513(4) 0.9778(3) 1.1851(4) 0.0910(15) Uani 1 1 d . . . H4A H 1.6578 0.9308 1.1611 0.137 Uiso 1 1 calc R . . H4B H 1.6513 0.9803 1.2723 0.137 Uiso 1 1 calc R . . H4C H 1.7233 1.0031 1.1631 0.137 Uiso 1 1 calc R . . C5 C 1.2659(5) 1.1309(2) 1.0279(4) 0.0754(12) Uani 1 1 d . . . H5A H 1.1810 1.1124 1.0275 0.113 Uiso 1 1 calc R . . H5B H 1.2730 1.1507 0.9492 0.113 Uiso 1 1 calc R . . H5C H 1.2813 1.1657 1.0901 0.113 Uiso 1 1 calc R . . C6 C 1.2839(4) 1.0545(2) 0.7506(3) 0.0580(9) Uani 1 1 d . . . C7 C 1.2080(4) 1.0921(2) 0.6625(4) 0.0680(11) Uani 1 1 d . . . H7 H 1.2366 1.1196 0.6026 0.082 Uiso 1 1 calc R . . C8 C 1.0828(4) 1.08147(19) 0.6797(3) 0.0590(10) Uani 1 1 d . . . C9 C 1.4253(4) 1.0443(3) 0.7701(4) 0.0797(13) Uani 1 1 d . . . H9A H 1.4443 0.9968 0.7865 0.120 Uiso 1 1 calc R . . H9B H 1.4627 1.0716 0.8385 0.120 Uiso 1 1 calc R . . H9C H 1.4604 1.0581 0.6977 0.120 Uiso 1 1 calc R . . C10 C 0.9632(5) 1.1090(3) 0.6050(4) 0.0866(14) Uani 1 1 d . . . H10A H 0.9489 1.1553 0.6296 0.130 Uiso 1 1 calc R . . H10B H 0.8909 1.0811 0.6180 0.130 Uiso 1 1 calc R . . H10C H 0.9734 1.1082 0.5196 0.130 Uiso 1 1 calc R . . C11 C 1.2334(3) 0.98564(16) 0.9290(3) 0.0450(8) Uani 1 1 d . . . C12 C 1.1661(3) 0.92879(16) 0.9571(3) 0.0436(7) Uani 1 1 d . . . C13 C 1.0100(4) 0.83869(17) 0.9192(3) 0.0532(9) Uani 1 1 d . . . H13 H 1.0396 0.8279 1.0054 0.064 Uiso 1 1 calc R . . C14 C 1.0675(4) 0.78571(18) 0.8421(3) 0.0574(10) Uani 1 1 d . . . C15 C 1.0994(5) 0.7989(2) 0.7267(4) 0.0708(12) Uani 1 1 d . . . H15 H 1.0883 0.8429 0.6942 0.085 Uiso 1 1 calc R . . C16 C 1.1479(5) 0.7472(2) 0.6580(4) 0.0795(13) Uani 1 1 d . . . H16 H 1.1683 0.7568 0.5801 0.095 Uiso 1 1 calc R . . C17 C 1.1656(6) 0.6820(2) 0.7058(5) 0.0904(16) Uani 1 1 d . . . H17 H 1.1990 0.6476 0.6608 0.108 Uiso 1 1 calc R . . C18 C 1.1337(7) 0.6682(2) 0.8204(5) 0.1013(18) Uani 1 1 d . . . H18 H 1.1432 0.6239 0.8519 0.122 Uiso 1 1 calc R . . C19 C 1.0879(5) 0.7194(2) 0.8887(4) 0.0794(13) Uani 1 1 d . . . H19 H 1.0702 0.7096 0.9674 0.095 Uiso 1 1 calc R . . C20 C 0.8627(4) 0.8343(2) 0.9005(5) 0.0782(13) Uani 1 1 d . . . H20A H 0.8309 0.8398 0.8150 0.117 Uiso 1 1 calc R . . H20B H 0.8283 0.8699 0.9468 0.117 Uiso 1 1 calc R . . H20C H 0.8366 0.7904 0.9280 0.117 Uiso 1 1 calc R . . C21 C 0.8685(4) 0.9393(3) 0.6394(4) 0.0753(12) Uani 1 1 d . . . H21A H 0.9187 0.9586 0.5800 0.090 Uiso 1 1 calc R . . H21B H 0.8818 0.8900 0.6394 0.090 Uiso 1 1 calc R . . C22 C 0.7272(6) 0.9528(4) 0.5937(6) 0.130(3) Uani 1 1 d . . . H22A H 0.7110 1.0012 0.5944 0.195 Uiso 1 1 calc R . . H22B H 0.6748 0.9300 0.6463 0.195 Uiso 1 1 calc R . . H22C H 0.7067 0.9356 0.5116 0.195 Uiso 1 1 calc R . . C23 C 0.8232(4) 1.0220(3) 0.9013(4) 0.0753(12) Uani 1 1 d . . . H23A H 0.7491 0.9926 0.9044 0.090 Uiso 1 1 calc R . . H23B H 0.8671 1.0260 0.9846 0.090 Uiso 1 1 calc R . . C24 C 0.7740(5) 1.0920(3) 0.8617(5) 0.0961(16) Uani 1 1 d . . . H24A H 0.7233 1.0889 0.7823 0.144 Uiso 1 1 calc R . . H24B H 0.8454 1.1223 0.8575 0.144 Uiso 1 1 calc R . . H24C H 0.7218 1.1095 0.9199 0.144 Uiso 1 1 calc R . . C25 C 1.0330(5) 0.9647(3) 1.1984(4) 0.0792(13) Uani 1 1 d . . . H25A H 1.0619 1.0034 1.1540 0.095 Uiso 1 1 calc R . . H25B H 0.9579 0.9454 1.1488 0.095 Uiso 1 1 calc R . . C26 C 0.9947(5) 0.9899(3) 1.3179(4) 0.1030(18) Uani 1 1 d . . . H26A H 1.0645 1.0156 1.3618 0.154 Uiso 1 1 calc R . . H26B H 0.9752 0.9514 1.3666 0.154 Uiso 1 1 calc R . . H26C H 0.9203 1.0188 1.3014 0.154 Uiso 1 1 calc R . . C27 C 1.1141(5) 0.8000(3) 1.2542(5) 0.0864(15) Uani 1 1 d . . . H27A H 1.1426 0.7693 1.1940 0.104 Uiso 1 1 calc R . . H27B H 1.1577 0.7864 1.3340 0.104 Uiso 1 1 calc R . . C28 C 0.9692(7) 0.7896(4) 1.2534(8) 0.152(3) Uani 1 1 d . . . H34A H 0.9234 0.8101 1.1809 0.229 Uiso 1 1 calc R . . H34B H 0.9430 0.8109 1.3247 0.229 Uiso 1 1 calc R . . H34C H 0.9505 0.7414 1.2542 0.229 Uiso 1 1 calc R . . C29 C 1.3228(5) 0.9287(3) 1.3312(4) 0.0837(13) Uani 1 1 d . . . H28A H 1.3986 0.9053 1.3107 0.100 Uiso 1 1 calc R . . H28B H 1.3334 0.9772 1.3154 0.100 Uiso 1 1 calc R . . C30 C 1.3180(6) 0.9196(4) 1.4656(4) 0.126(2) Uani 1 1 d . . . H30A H 1.3954 0.9375 1.5113 0.190 Uiso 1 1 calc R . . H30B H 1.3105 0.8717 1.4835 0.190 Uiso 1 1 calc R . . H30C H 1.2450 0.9438 1.4882 0.190 Uiso 1 1 calc R . . C31 C 1.4103(6) 0.8467(3) 0.8577(5) 0.1044(19) Uani 1 1 d D . . H31A H 1.3640 0.8041 0.8389 0.125 Uiso 1 1 calc R A 1 H31B H 1.3665 0.8819 0.8053 0.125 Uiso 1 1 calc R A 1 C32 C 1.5339(9) 0.8389(7) 0.8258(10) 0.087(3) Uani 0.50 1 d PD B 1 H32A H 1.5279 0.8273 0.7404 0.131 Uiso 0.50 1 calc PR B 1 H32B H 1.5781 0.8030 0.8743 0.131 Uiso 0.50 1 calc PR B 1 H32C H 1.5806 0.8811 0.8407 0.131 Uiso 0.50 1 calc PR B 1 C32A C 1.4762(15) 0.7843(8) 0.8238(12) 0.124(5) Uani 0.50 1 d PD B 2 H32D H 1.4705 0.7817 0.7360 0.186 Uiso 0.50 1 calc PR B 2 H32E H 1.4360 0.7447 0.8538 0.186 Uiso 0.50 1 calc PR B 2 H32F H 1.5650 0.7859 0.8592 0.186 Uiso 0.50 1 calc PR B 2 C33 C 1.4778(7) 0.8098(3) 1.1560(6) 0.119(2) Uani 1 1 d D . . H33A H 1.5692 0.8202 1.1690 0.143 Uiso 1 1 calc R B 1 H33B H 1.4441 0.8210 1.2313 0.143 Uiso 1 1 calc R B 1 C34 C 1.463(2) 0.7372(6) 1.1358(16) 0.123(5) Uani 0.50 1 d PD B 1 H34D H 1.5075 0.7129 1.2051 0.185 Uiso 0.50 1 calc PR B 1 H34E H 1.4991 0.7247 1.0632 0.185 Uiso 0.50 1 calc PR B 1 H34F H 1.3735 0.7255 1.1258 0.185 Uiso 0.50 1 calc PR B 1 C34A C 1.560(2) 0.7542(10) 1.1292(19) 0.193(13) Uani 0.50 1 d PD B 2 H35D H 1.5918 0.7307 1.2038 0.290 Uiso 0.50 1 calc PR B 2 H35E H 1.6309 0.7721 1.0925 0.290 Uiso 0.50 1 calc PR B 2 H35F H 1.5116 0.7228 1.0734 0.290 Uiso 0.50 1 calc PR B 2 C101 C 0.4602(5) 0.1857(4) 0.4865(7) 0.099(3) Uiso 0.60 1 d PGDU C 1 C102 C 0.4066(6) 0.1312(3) 0.4156(7) 0.078(2) Uiso 0.60 1 d PGDU C 1 H102 H 0.4552 0.0921 0.4067 0.094 Uiso 0.60 1 calc PR C 1 C103 C 0.2802(7) 0.1351(3) 0.3582(6) 0.105(3) Uiso 0.60 1 d PGDU C 1 H103 H 0.2443 0.0987 0.3108 0.127 Uiso 0.60 1 calc PR C 1 C104 C 0.2075(5) 0.1936(4) 0.3716(7) 0.085(2) Uiso 0.60 1 d PGDU C 1 H104 H 0.1229 0.1962 0.3331 0.102 Uiso 0.60 1 calc PR C 1 C105 C 0.2611(7) 0.2481(3) 0.4424(8) 0.137(4) Uiso 0.60 1 d PGDU C 1 H105 H 0.2124 0.2872 0.4514 0.165 Uiso 0.60 1 calc PR C 1 C106 C 0.3874(8) 0.2441(3) 0.4999(8) 0.101(3) Uiso 0.60 1 d PGDU C 1 H106 H 0.4233 0.2806 0.5473 0.121 Uiso 0.60 1 calc PR C 1 C107 C 0.5894(12) 0.1819(7) 0.5345(11) 0.129(4) Uiso 0.60 1 d PD C 1 H10D H 0.6133 0.2222 0.5825 0.193 Uiso 0.60 1 calc PR C 1 H10E H 0.6405 0.1789 0.4687 0.193 Uiso 0.60 1 calc PR C 1 H10F H 0.6038 0.1419 0.5856 0.193 Uiso 0.60 1 calc PR C 1 C201 C 0.4516(9) 0.1634(6) 0.4524(10) 0.115(5) Uiso 0.40 1 d PGDU D 2 C202 C 0.3451(13) 0.1367(5) 0.3783(11) 0.103(4) Uiso 0.40 1 d PGDU D 2 H202 H 0.3514 0.0952 0.3381 0.123 Uiso 0.40 1 calc PR D 2 C203 C 0.2290(10) 0.1723(8) 0.3643(13) 0.155(7) Uiso 0.40 1 d PGDU D 2 H203 H 0.1578 0.1544 0.3147 0.186 Uiso 0.40 1 calc PR D 2 C204 C 0.2195(10) 0.2344(7) 0.4244(14) 0.121(5) Uiso 0.40 1 d PGDU D 2 H204 H 0.1419 0.2582 0.4150 0.145 Uiso 0.40 1 calc PR D 2 C205 C 0.3260(14) 0.2610(6) 0.4985(14) 0.150(7) Uiso 0.40 1 d PGDU D 2 H205 H 0.3197 0.3026 0.5387 0.180 Uiso 0.40 1 calc PR D 2 C206 C 0.4421(11) 0.2255(7) 0.5125(13) 0.129(5) Uiso 0.40 1 d PGDU D 2 H206 H 0.5133 0.2433 0.5621 0.155 Uiso 0.40 1 calc PR D 2 C207 C 0.5504(13) 0.1197(9) 0.4694(16) 0.156(7) Uiso 0.40 1 d PGD D 2 H20D H 0.6210 0.1407 0.5210 0.234 Uiso 0.40 1 calc PR D 2 H20E H 0.5766 0.1084 0.3916 0.234 Uiso 0.40 1 calc PR D 2 H20F H 0.5247 0.0787 0.5079 0.234 Uiso 0.40 1 calc PR D 2 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 Al1 0.0561(6) 0.0572(6) 0.0422(6) 0.0056(5) 0.0024(4) 0.0003(5) Al2 0.0694(7) 0.0578(6) 0.0415(6) 0.0060(5) 0.0081(5) 0.0032(6) Al3 0.0735(8) 0.0626(7) 0.0589(7) -0.0003(6) 0.0066(6) 0.0237(6) N5 0.0598(18) 0.0388(15) 0.0424(14) 0.0009(12) 0.0054(13) -0.0045(13) N4 0.0499(17) 0.0478(15) 0.0439(15) 0.0064(13) 0.0092(13) 0.0001(13) N3 0.0576(18) 0.0474(16) 0.0474(16) 0.0121(13) 0.0036(14) 0.0004(14) N2 0.0496(16) 0.0509(16) 0.0462(15) 0.0031(14) 0.0027(13) -0.0010(14) N1 0.0505(17) 0.074(2) 0.0481(16) 0.0094(16) 0.0090(14) 0.0087(17) O1 0.0640(15) 0.0429(12) 0.0414(12) 0.0051(10) 0.0063(11) 0.0063(11) C1 0.048(2) 0.102(3) 0.044(2) 0.007(2) 0.0041(17) -0.010(2) C2 0.063(3) 0.087(3) 0.055(2) -0.005(2) 0.005(2) -0.025(2) C3 0.067(2) 0.059(2) 0.047(2) -0.0022(18) 0.0095(18) -0.0105(19) C4 0.054(2) 0.138(4) 0.077(3) 0.014(3) -0.002(2) 0.001(3) C5 0.090(3) 0.054(2) 0.081(3) -0.006(2) 0.011(3) -0.007(2) C6 0.065(2) 0.064(2) 0.046(2) 0.0105(18) 0.0145(18) -0.0054(19) C7 0.080(3) 0.069(3) 0.056(2) 0.018(2) 0.015(2) -0.005(2) C8 0.076(3) 0.055(2) 0.044(2) 0.0095(17) 0.0031(19) -0.001(2) C9 0.068(3) 0.107(3) 0.069(3) 0.018(3) 0.025(2) -0.005(3) C10 0.098(4) 0.086(3) 0.070(3) 0.032(2) -0.009(3) 0.011(3) C11 0.0546(19) 0.0451(18) 0.0347(16) 0.0031(14) 0.0035(14) 0.0044(16) C12 0.055(2) 0.0376(16) 0.0376(17) 0.0009(14) 0.0050(15) 0.0035(15) C13 0.070(2) 0.0434(18) 0.0445(19) 0.0028(15) 0.0027(17) -0.0143(17) C14 0.070(2) 0.047(2) 0.051(2) -0.0031(17) -0.0049(18) -0.0062(18) C15 0.097(3) 0.057(2) 0.056(2) 0.001(2) 0.003(2) 0.001(2) C16 0.097(3) 0.083(3) 0.056(3) -0.011(2) 0.005(2) 0.000(3) C17 0.123(4) 0.062(3) 0.081(3) -0.026(3) -0.003(3) 0.006(3) C18 0.162(6) 0.054(3) 0.088(4) 0.001(3) 0.015(4) 0.006(3) C19 0.121(4) 0.049(2) 0.066(3) 0.001(2) 0.004(2) -0.002(2) C20 0.082(3) 0.069(3) 0.086(3) 0.001(2) 0.022(2) -0.026(2) C21 0.081(3) 0.085(3) 0.056(2) 0.003(2) -0.005(2) -0.010(2) C22 0.114(5) 0.139(6) 0.116(5) 0.008(4) -0.061(4) -0.003(4) C23 0.070(3) 0.090(3) 0.067(3) 0.011(2) 0.013(2) 0.019(2) C24 0.093(4) 0.103(4) 0.094(4) -0.012(3) 0.018(3) 0.020(3) C25 0.090(3) 0.095(3) 0.052(2) 0.001(2) 0.009(2) 0.018(3) C26 0.093(4) 0.138(5) 0.077(3) -0.016(3) 0.008(3) 0.036(4) C27 0.113(4) 0.079(3) 0.065(3) 0.022(2) 0.005(3) -0.011(3) C28 0.130(6) 0.155(7) 0.172(7) 0.066(6) 0.021(5) -0.057(5) C29 0.087(3) 0.099(3) 0.064(3) -0.008(3) 0.004(2) -0.006(3) C30 0.125(5) 0.186(7) 0.061(3) 0.003(4) -0.013(3) -0.025(5) C31 0.116(4) 0.107(4) 0.088(4) -0.023(3) 0.011(3) 0.045(3) C32 0.061(6) 0.121(9) 0.085(7) -0.016(7) 0.034(5) 0.001(6) C32A 0.125(11) 0.143(12) 0.099(9) -0.044(9) -0.001(8) 0.051(10) C33 0.137(5) 0.091(4) 0.119(5) 0.014(4) -0.024(4) 0.050(4) C34 0.194(17) 0.068(7) 0.110(10) 0.020(7) 0.033(11) 0.027(10) C34A 0.26(3) 0.173(18) 0.171(16) 0.105(15) 0.13(2) 0.17(2) _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 Al1 N5 1.913(3) . ? Al1 N3 1.970(3) . ? Al1 C23 1.976(5) . ? Al1 C21 1.979(4) . ? Al2 C25 1.972(5) . ? Al2 O1 1.985(2) . ? Al2 C27 1.993(5) . ? Al2 C29 1.994(5) . ? Al3 O1 1.886(3) . ? Al3 C31 1.945(6) . ? Al3 C33 1.954(5) . ? Al3 N1 1.972(4) . ? N5 C12 1.340(4) . ? N5 C13 1.487(4) . ? N4 C6 1.349(5) . ? N4 N3 1.377(4) . ? N4 C11 1.415(4) . ? N3 C8 1.343(4) . ? N2 C3 1.352(5) . ? N2 N1 1.373(4) . ? N2 C11 1.417(4) . ? N1 C1 1.355(5) . ? O1 C12 1.383(4) . ? C1 C2 1.367(7) . ? C1 C4 1.514(6) . ? C2 C3 1.371(6) . ? C3 C5 1.488(6) . ? C6 C7 1.379(5) . ? C6 C9 1.482(6) . ? C7 C8 1.367(6) . ? C8 C10 1.501(6) . ? C11 C12 1.371(5) . ? C13 C14 1.513(5) . ? C13 C20 1.532(6) . ? C14 C15 1.381(6) . ? C14 C19 1.397(6) . ? C15 C16 1.396(6) . ? C16 C17 1.378(7) . ? C17 C18 1.375(7) . ? C18 C19 1.374(7) . ? C21 C22 1.521(7) . ? C23 C24 1.501(7) . ? C25 C26 1.509(6) . ? C27 C28 1.532(8) . ? C29 C30 1.497(7) . ? C31 C32 1.397(9) . ? C31 C32A 1.471(11) . ? C33 C34A 1.439(12) . ? C33 C34 1.438(12) . ? C101 C102 1.3900 . ? C101 C106 1.3900 . ? C101 C107 1.387(12) . ? C102 C103 1.3900 . ? C103 C104 1.3900 . ? C104 C105 1.3900 . ? C105 C106 1.3900 . ? C201 C207 1.3335 . ? C201 C202 1.3900 . ? C201 C206 1.3900 . ? C202 C203 1.3900 . ? C203 C204 1.3900 . ? C204 C205 1.3900 . ? C205 C206 1.3900 . ? 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 N5 Al1 N3 95.91(12) . . ? N5 Al1 C23 112.99(15) . . ? N3 Al1 C23 107.73(18) . . ? N5 Al1 C21 113.20(17) . . ? N3 Al1 C21 105.99(17) . . ? C23 Al1 C21 118.1(2) . . ? C25 Al2 O1 103.08(14) . . ? C25 Al2 C27 115.6(2) . . ? O1 Al2 C27 105.48(18) . . ? C25 Al2 C29 110.7(2) . . ? O1 Al2 C29 105.63(17) . . ? C27 Al2 C29 114.9(2) . . ? O1 Al3 C31 113.48(19) . . ? O1 Al3 C33 109.9(3) . . ? C31 Al3 C33 117.8(3) . . ? O1 Al3 N1 89.91(12) . . ? C31 Al3 N1 107.7(2) . . ? C33 Al3 N1 114.8(2) . . ? C12 N5 C13 115.9(3) . . ? C12 N5 Al1 121.7(2) . . ? C13 N5 Al1 122.1(2) . . ? C6 N4 N3 110.4(3) . . ? C6 N4 C11 128.8(3) . . ? N3 N4 C11 120.4(3) . . ? C8 N3 N4 105.7(3) . . ? C8 N3 Al1 128.7(2) . . ? N4 N3 Al1 118.9(2) . . ? C3 N2 N1 110.5(3) . . ? C3 N2 C11 129.4(3) . . ? N1 N2 C11 119.8(3) . . ? C1 N1 N2 105.3(3) . . ? C1 N1 Al3 139.3(3) . . ? N2 N1 Al3 112.3(2) . . ? C12 O1 Al3 109.1(2) . . ? C12 O1 Al2 121.5(2) . . ? Al3 O1 Al2 123.77(11) . . ? N1 C1 C2 109.9(3) . . ? N1 C1 C4 120.6(4) . . ? C2 C1 C4 129.6(4) . . ? C1 C2 C3 107.4(4) . . ? N2 C3 C2 106.7(4) . . ? N2 C3 C5 121.4(3) . . ? C2 C3 C5 131.9(4) . . ? N4 C6 C7 106.6(3) . . ? N4 C6 C9 123.4(3) . . ? C7 C6 C9 129.9(4) . . ? C8 C7 C6 107.1(3) . . ? N3 C8 C7 110.2(3) . . ? N3 C8 C10 121.7(4) . . ? C7 C8 C10 128.0(4) . . ? C12 C11 N4 123.3(3) . . ? C12 C11 N2 121.0(3) . . ? N4 C11 N2 115.7(3) . . ? N5 C12 C11 124.3(3) . . ? N5 C12 O1 120.9(3) . . ? C11 C12 O1 114.8(3) . . ? N5 C13 C14 113.6(3) . . ? N5 C13 C20 110.0(3) . . ? C14 C13 C20 111.0(3) . . ? C15 C14 C19 117.8(4) . . ? C15 C14 C13 123.6(3) . . ? C19 C14 C13 118.6(4) . . ? C14 C15 C16 121.0(4) . . ? C17 C16 C15 119.9(5) . . ? C18 C17 C16 119.6(5) . . ? C17 C18 C19 120.4(5) . . ? C18 C19 C14 121.2(4) . . ? C22 C21 Al1 118.3(4) . . ? C24 C23 Al1 118.9(3) . . ? C26 C25 Al2 113.7(3) . . ? C28 C27 Al2 116.1(4) . . ? C30 C29 Al2 116.0(4) . . ? C32 C31 C32A 50.4(7) . . ? C32 C31 Al3 117.6(6) . . ? C32A C31 Al3 122.8(7) . . ? C34A C33 C34 44.0(11) . . ? C34A C33 Al3 121.6(9) . . ? C34 C33 Al3 117.2(8) . . ? C102 C101 C106 120.0 . . ? C102 C101 C107 118.1(7) . . ? C106 C101 C107 121.7(7) . . ? C103 C102 C101 120.0 . . ? C102 C103 C104 120.0 . . ? C105 C104 C103 120.0 . . ? C104 C105 C106 120.0 . . ? C105 C106 C101 120.0 . . ? C207 C201 C202 113.0 . . ? C207 C201 C206 126.4 . . ? C202 C201 C206 120.0 . . ? C201 C202 C203 120.0 . . ? C204 C203 C202 120.0 . . ? C203 C204 C205 120.0 . . ? C206 C205 C204 120.0 . . ? C205 C206 C201 120.0 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.302 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.039 _database_code_depnum_ccdc_archive 'CCDC 933662'