# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Zhong-Xia Wang' _publ_contact_author_email ZXWANG@USTC.EDU.CN _publ_section_title ; Synthesis and characterization of lithium, aluminum and zinc complexes supported by pyrazolyl-based N,N?-chelate ligands ; loop_ _publ_author_name 'Zhong-Xia Wang' 'Can Jin' # Attachment '2a.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 687139' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H52 Li2 N6 Si2' _chemical_formula_weight 542.82 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' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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 9.857(2) _cell_length_b 18.365(4) _cell_length_c 19.384(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.51(3) _cell_angle_gamma 90.00 _cell_volume 3460.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2267 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.76 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.042 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.9800 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8771 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3058 _reflns_number_gt 2006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0603P)^2^+3.2151P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3058 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1454 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 Si1 Si 0.37271(8) 0.05813(4) 0.35053(4) 0.0497(3) Uani 1 1 d . . . N1 N 0.7105(2) 0.14022(12) 0.38985(11) 0.0444(5) Uani 1 1 d . . . N2 N 0.6300(2) 0.17368(11) 0.43236(10) 0.0402(5) Uani 1 1 d . . . N3 N 0.4100(2) 0.13881(11) 0.31339(10) 0.0383(5) Uani 1 1 d . . . C1 C 0.9151(3) 0.0611(2) 0.40571(19) 0.0823(11) Uani 1 1 d . . . H1A H 0.8844 0.0116 0.3999 0.123 Uiso 1 1 calc R . . H1B H 1.0002 0.0629 0.4380 0.123 Uiso 1 1 calc R . . H1C H 0.9289 0.0804 0.3614 0.123 Uiso 1 1 calc R . . C2 C 0.8090(3) 0.10555(15) 0.43359(15) 0.0518(7) Uani 1 1 d . . . C3 C 0.7938(3) 0.11787(15) 0.50281(15) 0.0563(8) Uani 1 1 d . . . H3 H 0.8502 0.1002 0.5425 0.068 Uiso 1 1 calc R . . C4 C 0.6800(3) 0.16098(15) 0.50123(13) 0.0465(7) Uani 1 1 d . . . C5 C 0.6121(4) 0.19168(18) 0.55837(14) 0.0671(9) Uani 1 1 d . . . H5A H 0.6127 0.2439 0.5560 0.101 Uiso 1 1 calc R . . H5B H 0.6611 0.1762 0.6029 0.101 Uiso 1 1 calc R . . H5C H 0.5188 0.1747 0.5529 0.101 Uiso 1 1 calc R . . C6 C 0.5192(3) 0.22095(14) 0.40489(13) 0.0437(6) Uani 1 1 d . . . H6 H 0.5159 0.2664 0.4256 0.052 Uiso 1 1 calc R . . C7 C 0.4187(3) 0.20418(14) 0.35076(12) 0.0405(6) Uani 1 1 d . . . C8 C 0.3050(3) 0.26190(17) 0.32857(15) 0.0575(8) Uani 1 1 d . . . C9 C 0.2861(5) 0.2759(2) 0.25051(19) 0.1092(16) Uani 1 1 d . . . H9A H 0.2206 0.3145 0.2385 0.164 Uiso 1 1 calc R . . H9B H 0.2530 0.2324 0.2258 0.164 Uiso 1 1 calc R . . H9C H 0.3726 0.2897 0.2378 0.164 Uiso 1 1 calc R . . C10 C 0.1691(4) 0.2311(3) 0.3447(3) 0.133(2) Uani 1 1 d . . . H10A H 0.0974 0.2664 0.3326 0.200 Uiso 1 1 calc R . . H10B H 0.1787 0.2199 0.3936 0.200 Uiso 1 1 calc R . . H10C H 0.1461 0.1875 0.3178 0.200 Uiso 1 1 calc R . . C11 C 0.3310(6) 0.3347(2) 0.3661(3) 0.145(2) Uani 1 1 d . . . H11A H 0.4141 0.3558 0.3553 0.217 Uiso 1 1 calc R . . H11B H 0.3402 0.3272 0.4157 0.217 Uiso 1 1 calc R . . H11C H 0.2552 0.3669 0.3510 0.217 Uiso 1 1 calc R . . C12 C 0.3370(4) 0.0681(2) 0.44194(15) 0.0783(11) Uani 1 1 d . . . H12A H 0.4197 0.0825 0.4723 0.118 Uiso 1 1 calc R . . H12B H 0.3056 0.0224 0.4575 0.118 Uiso 1 1 calc R . . H12C H 0.2675 0.1045 0.4429 0.118 Uiso 1 1 calc R . . C13 C 0.2180(3) 0.01462(19) 0.29644(18) 0.0767(10) Uani 1 1 d . . . H13A H 0.1406 0.0469 0.2936 0.115 Uiso 1 1 calc R . . H13B H 0.1975 -0.0303 0.3179 0.115 Uiso 1 1 calc R . . H13C H 0.2368 0.0051 0.2503 0.115 Uiso 1 1 calc R . . C14 C 0.5146(4) -0.01093(18) 0.3532(2) 0.0850(11) Uani 1 1 d . . . H14A H 0.5493 -0.0099 0.3098 0.128 Uiso 1 1 calc R . . H14B H 0.4793 -0.0586 0.3603 0.128 Uiso 1 1 calc R . . H14C H 0.5875 0.0005 0.3909 0.128 Uiso 1 1 calc R . . Li1 Li 0.6109(4) 0.1392(3) 0.2917(2) 0.0468(11) 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 Si1 0.0492(5) 0.0514(5) 0.0473(5) 0.0058(4) 0.0041(3) -0.0111(4) N1 0.0411(12) 0.0483(13) 0.0416(12) 0.0008(10) -0.0003(10) 0.0010(11) N2 0.0427(12) 0.0417(12) 0.0343(11) 0.0006(9) 0.0004(9) -0.0053(10) N3 0.0387(12) 0.0430(12) 0.0330(11) -0.0004(9) 0.0051(9) -0.0012(10) C1 0.058(2) 0.093(3) 0.089(3) -0.004(2) -0.0081(18) 0.023(2) C2 0.0484(17) 0.0489(16) 0.0523(17) 0.0048(14) -0.0091(13) -0.0029(14) C3 0.0601(19) 0.0509(17) 0.0485(17) 0.0136(14) -0.0187(14) -0.0118(15) C4 0.0562(17) 0.0475(16) 0.0319(14) 0.0030(12) -0.0040(12) -0.0186(14) C5 0.090(2) 0.072(2) 0.0388(16) -0.0010(15) 0.0093(16) -0.0236(19) C6 0.0511(16) 0.0409(14) 0.0384(14) -0.0046(12) 0.0050(12) 0.0014(12) C7 0.0418(14) 0.0467(15) 0.0347(13) 0.0045(12) 0.0107(11) 0.0022(12) C8 0.0557(18) 0.0632(19) 0.0514(17) -0.0035(15) 0.0026(14) 0.0234(15) C9 0.137(4) 0.123(3) 0.067(2) 0.028(2) 0.015(2) 0.083(3) C10 0.060(3) 0.164(5) 0.181(5) 0.040(4) 0.038(3) 0.048(3) C11 0.164(5) 0.089(3) 0.153(4) -0.052(3) -0.059(4) 0.080(3) C12 0.093(3) 0.092(3) 0.0516(18) 0.0126(17) 0.0142(17) -0.039(2) C13 0.073(2) 0.079(2) 0.076(2) -0.0086(19) 0.0036(18) -0.0231(19) C14 0.082(3) 0.056(2) 0.116(3) 0.025(2) 0.012(2) 0.0063(18) Li1 0.040(2) 0.064(3) 0.035(2) -0.001(2) 0.0022(19) 0.004(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 Si1 N3 1.713(2) . ? Si1 C12 1.872(3) . ? Si1 C13 1.880(3) . ? Si1 C14 1.882(3) . ? Si1 Li1 3.149(5) . ? Si1 Li1 3.160(4) 2_655 ? N1 C2 1.340(3) . ? N1 N2 1.379(3) . ? N1 Li1 1.992(4) . ? N2 C4 1.364(3) . ? N2 C6 1.428(3) . ? N3 C7 1.397(3) . ? N3 Li1 2.013(4) 2_655 ? N3 Li1 2.091(5) . ? C1 C2 1.496(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.393(4) . ? C3 C4 1.370(4) . ? C3 H3 0.9300 . ? C4 C5 1.496(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.354(3) . ? C6 H6 0.9300 . ? C7 C8 1.551(4) . ? C7 Li1 2.654(5) . ? C8 C9 1.516(4) . ? C8 C11 1.523(5) . ? C8 C10 1.533(5) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? Li1 N3 2.013(4) 2_655 ? Li1 Li1 2.493(8) 2_655 ? Li1 Si1 3.160(4) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Si1 C12 113.57(13) . . ? N3 Si1 C13 110.10(13) . . ? C12 Si1 C13 107.91(16) . . ? N3 Si1 C14 112.60(13) . . ? C12 Si1 C14 107.16(18) . . ? C13 Si1 C14 105.05(17) . . ? N3 Si1 Li1 38.23(11) . . ? C12 Si1 Li1 124.39(13) . . ? C13 Si1 Li1 125.69(13) . . ? C14 Si1 Li1 74.54(14) . . ? N3 Si1 Li1 34.99(10) . 2_655 ? C12 Si1 Li1 145.52(15) . 2_655 ? C13 Si1 Li1 82.39(14) . 2_655 ? C14 Si1 Li1 101.32(15) . 2_655 ? Li1 Si1 Li1 46.56(14) . 2_655 ? C2 N1 N2 105.2(2) . . ? C2 N1 Li1 142.3(2) . . ? N2 N1 Li1 109.52(19) . . ? C4 N2 N1 111.0(2) . . ? C4 N2 C6 126.8(2) . . ? N1 N2 C6 121.87(19) . . ? C7 N3 Si1 121.61(16) . . ? C7 N3 Li1 120.6(2) . 2_655 ? Si1 N3 Li1 115.78(17) . 2_655 ? C7 N3 Li1 97.03(19) . . ? Si1 N3 Li1 111.30(16) . . ? Li1 N3 Li1 74.80(19) 2_655 . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.5(3) . . ? N1 C2 C1 120.5(3) . . ? C3 C2 C1 129.0(3) . . ? C4 C3 C2 106.9(2) . . ? C4 C3 H3 126.6 . . ? C2 C3 H3 126.6 . . ? N2 C4 C3 106.4(2) . . ? N2 C4 C5 121.8(3) . . ? C3 C4 C5 131.8(2) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N2 124.6(2) . . ? C7 C6 H6 117.7 . . ? N2 C6 H6 117.7 . . ? C6 C7 N3 124.9(2) . . ? C6 C7 C8 117.5(2) . . ? N3 C7 C8 117.6(2) . . ? C6 C7 Li1 87.34(18) . . ? N3 C7 Li1 51.46(15) . . ? C8 C7 Li1 136.24(19) . . ? C9 C8 C11 108.1(3) . . ? C9 C8 C10 107.4(3) . . ? C11 C8 C10 108.1(4) . . ? C9 C8 C7 110.9(2) . . ? C11 C8 C7 114.2(3) . . ? C10 C8 C7 107.9(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? Si1 C12 H12A 109.5 . . ? Si1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? Si1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? Si1 C13 H13A 109.5 . . ? Si1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? Si1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? Si1 C14 H14A 109.5 . . ? Si1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? Si1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 Li1 N3 156.7(3) . 2_655 ? N1 Li1 N3 98.1(2) . . ? N3 Li1 N3 105.20(19) 2_655 . ? N1 Li1 Li1 149.3(3) . 2_655 ? N3 Li1 Li1 54.04(16) 2_655 2_655 ? N3 Li1 Li1 51.16(16) . 2_655 ? N1 Li1 C7 81.80(16) . . ? N3 Li1 C7 118.5(2) 2_655 . ? N3 Li1 C7 31.51(10) . . ? Li1 Li1 C7 70.61(18) 2_655 . ? N1 Li1 Si1 86.42(16) . . ? N3 Li1 Si1 114.06(18) 2_655 . ? N3 Li1 Si1 30.46(9) . . ? Li1 Li1 Si1 66.96(16) 2_655 . ? C7 Li1 Si1 55.12(10) . . ? N1 Li1 Si1 138.6(2) . 2_655 ? N3 Li1 Si1 29.22(9) 2_655 2_655 ? N3 Li1 Si1 111.15(17) . 2_655 ? Li1 Li1 Si1 66.47(15) 2_655 2_655 ? C7 Li1 Si1 137.02(16) . 2_655 ? Si1 Li1 Si1 104.02(13) . 2_655 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 N2 C4 1.2(3) . . . . ? Li1 N1 N2 C4 166.2(2) . . . . ? C2 N1 N2 C6 175.2(2) . . . . ? Li1 N1 N2 C6 -19.9(3) . . . . ? C12 Si1 N3 C7 3.0(2) . . . . ? C13 Si1 N3 C7 124.1(2) . . . . ? C14 Si1 N3 C7 -119.0(2) . . . . ? Li1 Si1 N3 C7 -113.2(2) . . . . ? Li1 Si1 N3 C7 163.9(3) 2_655 . . . ? C12 Si1 N3 Li1 -160.9(2) . . . 2_655 ? C13 Si1 N3 Li1 -39.8(2) . . . 2_655 ? C14 Si1 N3 Li1 77.1(2) . . . 2_655 ? Li1 Si1 N3 Li1 82.9(2) . . . 2_655 ? C12 Si1 N3 Li1 116.23(19) . . . . ? C13 Si1 N3 Li1 -122.65(19) . . . . ? C14 Si1 N3 Li1 -5.8(2) . . . . ? Li1 Si1 N3 Li1 -82.9(2) 2_655 . . . ? N2 N1 C2 C3 -1.3(3) . . . . ? Li1 N1 C2 C3 -157.8(3) . . . . ? N2 N1 C2 C1 178.6(3) . . . . ? Li1 N1 C2 C1 22.2(5) . . . . ? N1 C2 C3 C4 1.0(3) . . . . ? C1 C2 C3 C4 -178.9(3) . . . . ? N1 N2 C4 C3 -0.6(3) . . . . ? C6 N2 C4 C3 -174.2(2) . . . . ? N1 N2 C4 C5 179.6(2) . . . . ? C6 N2 C4 C5 6.0(4) . . . . ? C2 C3 C4 N2 -0.2(3) . . . . ? C2 C3 C4 C5 179.6(3) . . . . ? C4 N2 C6 C7 -136.5(3) . . . . ? N1 N2 C6 C7 50.5(3) . . . . ? N2 C6 C7 N3 -1.0(4) . . . . ? N2 C6 C7 C8 179.1(2) . . . . ? N2 C6 C7 Li1 -38.6(3) . . . . ? Si1 N3 C7 C6 69.2(3) . . . . ? Li1 N3 C7 C6 -127.6(3) 2_655 . . . ? Li1 N3 C7 C6 -51.2(3) . . . . ? Si1 N3 C7 C8 -110.9(2) . . . . ? Li1 N3 C7 C8 52.3(3) 2_655 . . . ? Li1 N3 C7 C8 128.7(2) . . . . ? Si1 N3 C7 Li1 120.4(2) . . . . ? Li1 N3 C7 Li1 -76.5(2) 2_655 . . . ? C6 C7 C8 C9 129.2(3) . . . . ? N3 C7 C8 C9 -50.7(4) . . . . ? Li1 C7 C8 C9 11.2(5) . . . . ? C6 C7 C8 C11 6.7(4) . . . . ? N3 C7 C8 C11 -173.2(3) . . . . ? Li1 C7 C8 C11 -111.3(4) . . . . ? C6 C7 C8 C10 -113.5(3) . . . . ? N3 C7 C8 C10 66.6(4) . . . . ? Li1 C7 C8 C10 128.5(3) . . . . ? C2 N1 Li1 N3 -52.9(9) . . . 2_655 ? N2 N1 Li1 N3 151.2(6) . . . 2_655 ? C2 N1 Li1 N3 127.7(3) . . . . ? N2 N1 Li1 N3 -28.1(3) . . . . ? C2 N1 Li1 Li1 128.8(3) . . . 2_655 ? N2 N1 Li1 Li1 -27.1(4) . . . 2_655 ? C2 N1 Li1 C7 154.8(3) . . . . ? N2 N1 Li1 C7 -1.1(2) . . . . ? C2 N1 Li1 Si1 99.5(4) . . . . ? N2 N1 Li1 Si1 -56.31(18) . . . . ? C2 N1 Li1 Si1 -7.7(6) . . . 2_655 ? N2 N1 Li1 Si1 -163.5(3) . . . 2_655 ? C7 N3 Li1 N1 59.5(2) . . . . ? Si1 N3 Li1 N1 -68.5(2) . . . . ? Li1 N3 Li1 N1 179.32(9) 2_655 . . . ? C7 N3 Li1 N3 -120.3(2) . . . 2_655 ? Si1 N3 Li1 N3 111.79(19) . . . 2_655 ? Li1 N3 Li1 N3 -0.4(3) 2_655 . . 2_655 ? C7 N3 Li1 Li1 -119.86(19) . . . 2_655 ? Si1 N3 Li1 Li1 112.20(17) . . . 2_655 ? Si1 N3 Li1 C7 -127.95(19) . . . . ? Li1 N3 Li1 C7 119.86(19) 2_655 . . . ? C7 N3 Li1 Si1 127.95(19) . . . . ? Li1 N3 Li1 Si1 -112.20(17) 2_655 . . . ? C7 N3 Li1 Si1 -150.42(17) . . . 2_655 ? Si1 N3 Li1 Si1 81.63(18) . . . 2_655 ? Li1 N3 Li1 Si1 -30.6(2) 2_655 . . 2_655 ? C6 C7 Li1 N1 19.7(2) . . . . ? N3 C7 Li1 N1 -120.5(2) . . . . ? C8 C7 Li1 N1 148.1(3) . . . . ? C6 C7 Li1 N3 -148.2(3) . . . 2_655 ? N3 C7 Li1 N3 71.6(2) . . . 2_655 ? C8 C7 Li1 N3 -19.8(4) . . . 2_655 ? C6 C7 Li1 N3 140.2(2) . . . . ? C8 C7 Li1 N3 -91.4(3) . . . . ? C6 C7 Li1 Li1 -174.05(19) . . . 2_655 ? N3 C7 Li1 Li1 45.74(16) . . . 2_655 ? C8 C7 Li1 Li1 -45.7(3) . . . 2_655 ? C6 C7 Li1 Si1 111.04(17) . . . . ? N3 C7 Li1 Si1 -29.17(13) . . . . ? C8 C7 Li1 Si1 -120.6(3) . . . . ? C6 C7 Li1 Si1 -177.3(3) . . . 2_655 ? N3 C7 Li1 Si1 42.5(2) . . . 2_655 ? C8 C7 Li1 Si1 -49.0(4) . . . 2_655 ? N3 Si1 Li1 N1 112.7(2) . . . . ? C12 Si1 Li1 N1 27.6(2) . . . . ? C13 Si1 Li1 N1 -170.53(17) . . . . ? C14 Si1 Li1 N1 -72.89(19) . . . . ? Li1 Si1 Li1 N1 164.26(18) 2_655 . . . ? N3 Si1 Li1 N3 -78.9(2) . . . 2_655 ? C12 Si1 Li1 N3 -164.0(2) . . . 2_655 ? C13 Si1 Li1 N3 -2.1(3) . . . 2_655 ? C14 Si1 Li1 N3 95.6(2) . . . 2_655 ? Li1 Si1 Li1 N3 -27.3(2) 2_655 . . 2_655 ? C12 Si1 Li1 N3 -85.1(2) . . . . ? C13 Si1 Li1 N3 76.8(2) . . . . ? C14 Si1 Li1 N3 174.5(2) . . . . ? Li1 Si1 Li1 N3 51.60(15) 2_655 . . . ? N3 Si1 Li1 Li1 -51.60(15) . . . 2_655 ? C12 Si1 Li1 Li1 -136.69(19) . . . 2_655 ? C13 Si1 Li1 Li1 25.21(18) . . . 2_655 ? C14 Si1 Li1 Li1 122.85(17) . . . 2_655 ? N3 Si1 Li1 C7 30.16(13) . . . . ? C12 Si1 Li1 C7 -54.93(19) . . . . ? C13 Si1 Li1 C7 106.97(17) . . . . ? C14 Si1 Li1 C7 -155.39(16) . . . . ? Li1 Si1 Li1 C7 81.76(11) 2_655 . . . ? N3 Si1 Li1 Si1 -108.01(18) . . . 2_655 ? C12 Si1 Li1 Si1 166.90(16) . . . 2_655 ? C13 Si1 Li1 Si1 -31.2(2) . . . 2_655 ? C14 Si1 Li1 Si1 66.44(17) . . . 2_655 ? Li1 Si1 Li1 Si1 -56.41(15) 2_655 . . 2_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.186 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.043 # Attachment '8.cif' data_080321a _database_code_depnum_ccdc_archive 'CCDC 687140' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 Al Cl2 N3' _chemical_formula_weight 400.27 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6331(14) _cell_length_b 16.006(2) _cell_length_c 15.3112(18) _cell_angle_alpha 90.00 _cell_angle_beta 103.749(2) _cell_angle_gamma 90.00 _cell_volume 2055.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3453 _cell_measurement_theta_min 2.739 _cell_measurement_theta_max 25.461 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9302 _exptl_absorpt_correction_T_max 0.9436 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10556 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3609 _reflns_number_gt 2499 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0596P)^2^+0.6706P] 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 3609 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.39991(10) 0.11287(5) 0.85684(5) 0.0456(2) Uani 1 1 d . . . Cl1 Cl 0.25262(11) 0.21467(6) 0.80074(6) 0.0795(3) Uani 1 1 d . . . Cl2 Cl 0.27027(10) 0.02809(6) 0.91782(6) 0.0710(3) Uani 1 1 d . . . N1 N 0.5758(3) 0.15305(14) 0.94512(15) 0.0458(6) Uani 1 1 d . . . N2 N 0.7285(3) 0.13210(13) 0.94206(14) 0.0407(5) Uani 1 1 d . . . N3 N 0.5085(3) 0.06717(15) 0.78075(14) 0.0461(6) Uani 1 1 d . . . C1 C 0.4468(5) 0.2451(3) 1.0373(3) 0.0888(12) Uani 1 1 d . . . H1A H 0.3908 0.2796 0.9886 0.133 Uiso 1 1 calc R . . H1B H 0.4798 0.2785 1.0906 0.133 Uiso 1 1 calc R . . H1C H 0.3777 0.2013 1.0480 0.133 Uiso 1 1 calc R . . C2 C 0.5900(4) 0.20784(19) 1.0135(2) 0.0560(8) Uani 1 1 d . . . C3 C 0.7483(4) 0.22061(19) 1.0530(2) 0.0584(8) Uani 1 1 d . . . H3 H 0.7897 0.2555 1.1015 0.070 Uiso 1 1 calc R . . C4 C 0.8339(3) 0.17223(17) 1.00733(18) 0.0485(7) Uani 1 1 d . . . C5 C 1.0089(4) 0.1617(2) 1.0208(2) 0.0679(9) Uani 1 1 d . . . H5A H 1.0371 0.1046 1.0359 0.102 Uiso 1 1 calc R . . H5B H 1.0631 0.1975 1.0687 0.102 Uiso 1 1 calc R . . H5C H 1.0395 0.1762 0.9664 0.102 Uiso 1 1 calc R . . C6 C 0.7624(3) 0.06722(16) 0.88724(17) 0.0418(6) Uani 1 1 d . . . H6 H 0.8630 0.0429 0.9041 0.050 Uiso 1 1 calc R . . C7 C 0.6631(3) 0.03759(16) 0.81330(16) 0.0403(6) Uani 1 1 d . . . C8 C 0.7167(3) -0.03826(16) 0.77159(16) 0.0439(7) Uani 1 1 d . . . C9 C 0.6164(4) -0.10588(19) 0.7482(2) 0.0599(8) Uani 1 1 d . . . H9 H 0.5121 -0.1029 0.7546 0.072 Uiso 1 1 calc R . . C10 C 0.6696(5) -0.1779(2) 0.7153(2) 0.0754(10) Uani 1 1 d . . . H10 H 0.6005 -0.2229 0.6989 0.091 Uiso 1 1 calc R . . C11 C 0.8221(5) -0.1838(2) 0.7066(2) 0.0769(11) Uani 1 1 d . . . H11 H 0.8577 -0.2330 0.6855 0.092 Uiso 1 1 calc R . . C12 C 0.9234(5) -0.1174(2) 0.7288(2) 0.0719(10) Uani 1 1 d . . . H12 H 1.0276 -0.1213 0.7223 0.086 Uiso 1 1 calc R . . C13 C 0.8714(4) -0.04473(19) 0.76074(19) 0.0556(8) Uani 1 1 d . . . H13 H 0.9406 0.0004 0.7752 0.067 Uiso 1 1 calc R . . C14 C 0.4352(4) 0.0594(2) 0.6879(2) 0.0659(9) Uani 1 1 d . . . C15 C 0.4988(6) 0.0873(3) 0.6211(2) 0.0789(11) Uani 1 1 d . . . C16 C 0.4073(8) 0.0795(3) 0.5294(3) 0.1116(18) Uani 1 1 d . . . H16 H 0.4485 0.0974 0.4817 0.134 Uiso 1 1 calc R . . C17 C 0.2639(8) 0.0463(4) 0.5151(3) 0.122(2) Uani 1 1 d . . . H17 H 0.2043 0.0432 0.4560 0.147 Uiso 1 1 calc R . . C18 C 0.1948(7) 0.0154(4) 0.5826(4) 0.145(2) Uani 1 1 d . . . H18 H 0.0940 -0.0089 0.5688 0.174 Uiso 1 1 calc R . . C19 C 0.2784(5) 0.0220(3) 0.6668(3) 0.1103(17) Uani 1 1 d . . . H19 H 0.2355 0.0023 0.7131 0.132 Uiso 1 1 calc R . . C20 C 0.6479(6) 0.1276(3) 0.6373(3) 0.0995(15) Uani 1 1 d . . . H20A H 0.6503 0.1724 0.6793 0.149 Uiso 1 1 calc R . . H20B H 0.6643 0.1496 0.5819 0.149 Uiso 1 1 calc R . . H20C H 0.7307 0.0882 0.6618 0.149 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 0.0407(5) 0.0517(5) 0.0462(5) 0.0063(4) 0.0141(4) 0.0039(4) Cl1 0.0710(6) 0.0794(6) 0.0878(6) 0.0231(5) 0.0180(5) 0.0286(5) Cl2 0.0653(5) 0.0794(6) 0.0744(5) 0.0143(4) 0.0290(4) -0.0131(4) N1 0.0446(14) 0.0492(14) 0.0463(13) -0.0014(11) 0.0164(11) 0.0022(11) N2 0.0423(13) 0.0410(12) 0.0388(12) -0.0002(10) 0.0099(10) 0.0018(10) N3 0.0390(13) 0.0605(14) 0.0377(12) 0.0001(11) 0.0069(10) 0.0031(11) C1 0.074(3) 0.108(3) 0.092(3) -0.032(2) 0.036(2) 0.011(2) C2 0.059(2) 0.0590(19) 0.0549(17) -0.0102(15) 0.0237(15) 0.0004(15) C3 0.067(2) 0.0569(19) 0.0523(17) -0.0154(15) 0.0164(16) -0.0051(16) C4 0.0529(18) 0.0449(16) 0.0471(16) -0.0053(13) 0.0108(14) -0.0021(14) C5 0.054(2) 0.076(2) 0.069(2) -0.0217(18) 0.0046(17) -0.0029(17) C6 0.0424(15) 0.0406(15) 0.0414(15) -0.0020(12) 0.0077(12) 0.0055(12) C7 0.0424(16) 0.0432(15) 0.0360(13) 0.0030(11) 0.0106(12) 0.0013(12) C8 0.0501(17) 0.0448(15) 0.0342(14) -0.0004(12) 0.0046(12) 0.0034(13) C9 0.062(2) 0.0554(19) 0.0602(19) -0.0059(15) 0.0113(16) -0.0061(16) C10 0.089(3) 0.051(2) 0.081(2) -0.0195(17) 0.010(2) -0.0098(19) C11 0.101(3) 0.053(2) 0.075(2) -0.0193(18) 0.017(2) 0.014(2) C12 0.072(2) 0.073(2) 0.074(2) -0.0143(19) 0.0214(19) 0.0170(19) C13 0.0529(19) 0.0560(18) 0.0574(18) -0.0101(15) 0.0124(15) 0.0024(15) C14 0.064(2) 0.086(2) 0.0419(17) -0.0042(16) 0.0003(16) 0.0268(19) C15 0.106(3) 0.077(3) 0.053(2) 0.0058(18) 0.017(2) 0.037(2) C16 0.146(5) 0.109(4) 0.071(3) -0.007(3) 0.007(3) 0.064(4) C17 0.130(5) 0.158(5) 0.064(3) -0.006(3) -0.008(3) 0.056(4) C18 0.096(4) 0.197(6) 0.119(4) -0.026(5) -0.022(4) 0.015(4) C19 0.084(3) 0.154(4) 0.071(3) -0.034(3) -0.024(2) 0.021(3) C20 0.156(5) 0.075(3) 0.076(3) 0.015(2) 0.044(3) 0.013(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 N3 1.814(2) . ? Al1 N1 1.890(2) . ? Al1 Cl2 2.1125(11) . ? Al1 Cl1 2.1190(12) . ? N1 C2 1.349(4) . ? N1 N2 1.372(3) . ? N2 C4 1.344(3) . ? N2 C6 1.409(3) . ? N3 C7 1.392(3) . ? N3 C14 1.417(4) . ? C1 C2 1.494(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.371(4) . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 C5 1.485(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.335(3) . ? C6 H6 0.9300 . ? C7 C8 1.496(4) . ? C8 C9 1.380(4) . ? C8 C13 1.388(4) . ? C9 C10 1.380(5) . ? C9 H9 0.9300 . ? C10 C11 1.357(5) . ? C10 H10 0.9300 . ? C11 C12 1.366(5) . ? C11 H11 0.9300 . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.346(5) . ? C14 C19 1.445(6) . ? C15 C20 1.408(6) . ? C15 C16 1.444(6) . ? C16 C17 1.317(7) . ? C16 H16 0.9300 . ? C17 C18 1.400(8) . ? C17 H17 0.9300 . ? C18 C19 1.323(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Al1 N1 98.43(10) . . ? N3 Al1 Cl2 115.71(9) . . ? N1 Al1 Cl2 108.82(8) . . ? N3 Al1 Cl1 113.68(9) . . ? N1 Al1 Cl1 109.33(9) . . ? Cl2 Al1 Cl1 110.07(5) . . ? C2 N1 N2 105.9(2) . . ? C2 N1 Al1 133.3(2) . . ? N2 N1 Al1 120.52(17) . . ? C4 N2 N1 110.1(2) . . ? C4 N2 C6 126.5(2) . . ? N1 N2 C6 122.5(2) . . ? C7 N3 C14 119.4(2) . . ? C7 N3 Al1 120.34(17) . . ? C14 N3 Al1 120.26(19) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.6(3) . . ? N1 C2 C1 121.4(3) . . ? C3 C2 C1 129.0(3) . . ? C4 C3 C2 107.0(3) . . ? C4 C3 H3 126.5 . . ? C2 C3 H3 126.5 . . ? N2 C4 C3 107.3(3) . . ? N2 C4 C5 122.4(3) . . ? C3 C4 C5 130.3(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N2 125.8(2) . . ? C7 C6 H6 117.1 . . ? N2 C6 H6 117.1 . . ? C6 C7 N3 123.4(2) . . ? C6 C7 C8 116.7(2) . . ? N3 C7 C8 119.4(2) . . ? C9 C8 C13 118.2(3) . . ? C9 C8 C7 120.6(3) . . ? C13 C8 C7 121.1(2) . . ? C8 C9 C10 120.5(3) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? C11 C10 C9 120.5(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.0(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 120.1(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.6(3) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C15 C14 N3 124.6(4) . . ? C15 C14 C19 119.7(4) . . ? N3 C14 C19 115.6(3) . . ? C14 C15 C20 122.6(4) . . ? C14 C15 C16 118.9(5) . . ? C20 C15 C16 118.5(4) . . ? C17 C16 C15 118.1(5) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C18 124.7(5) . . ? C16 C17 H17 117.7 . . ? C18 C17 H17 117.7 . . ? C19 C18 C17 117.4(6) . . ? C19 C18 H18 121.3 . . ? C17 C18 H18 121.3 . . ? C18 C19 C14 121.1(5) . . ? C18 C19 H19 119.4 . . ? C14 C19 H19 119.4 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Al1 N1 C2 164.8(3) . . . . ? Cl2 Al1 N1 C2 -74.3(3) . . . . ? Cl1 Al1 N1 C2 46.0(3) . . . . ? N3 Al1 N1 N2 -8.7(2) . . . . ? Cl2 Al1 N1 N2 112.25(18) . . . . ? Cl1 Al1 N1 N2 -127.50(18) . . . . ? C2 N1 N2 C4 0.6(3) . . . . ? Al1 N1 N2 C4 175.67(18) . . . . ? C2 N1 N2 C6 170.9(2) . . . . ? Al1 N1 N2 C6 -14.0(3) . . . . ? N1 Al1 N3 C7 28.1(2) . . . . ? Cl2 Al1 N3 C7 -87.6(2) . . . . ? Cl1 Al1 N3 C7 143.55(19) . . . . ? N1 Al1 N3 C14 -153.5(2) . . . . ? Cl2 Al1 N3 C14 90.9(2) . . . . ? Cl1 Al1 N3 C14 -38.0(3) . . . . ? N2 N1 C2 C3 -0.4(3) . . . . ? Al1 N1 C2 C3 -174.6(2) . . . . ? N2 N1 C2 C1 179.8(3) . . . . ? Al1 N1 C2 C1 5.6(5) . . . . ? N1 C2 C3 C4 0.1(4) . . . . ? C1 C2 C3 C4 179.9(3) . . . . ? N1 N2 C4 C3 -0.6(3) . . . . ? C6 N2 C4 C3 -170.4(2) . . . . ? N1 N2 C4 C5 179.8(3) . . . . ? C6 N2 C4 C5 10.0(4) . . . . ? C2 C3 C4 N2 0.3(3) . . . . ? C2 C3 C4 C5 179.9(3) . . . . ? C4 N2 C6 C7 -168.0(3) . . . . ? N1 N2 C6 C7 23.4(4) . . . . ? N2 C6 C7 N3 -0.8(4) . . . . ? N2 C6 C7 C8 -172.9(2) . . . . ? C14 N3 C7 C6 154.3(3) . . . . ? Al1 N3 C7 C6 -27.2(4) . . . . ? C14 N3 C7 C8 -33.8(4) . . . . ? Al1 N3 C7 C8 144.67(19) . . . . ? C6 C7 C8 C9 131.4(3) . . . . ? N3 C7 C8 C9 -41.1(4) . . . . ? C6 C7 C8 C13 -44.5(4) . . . . ? N3 C7 C8 C13 143.1(3) . . . . ? C13 C8 C9 C10 0.3(4) . . . . ? C7 C8 C9 C10 -175.6(3) . . . . ? C8 C9 C10 C11 0.9(5) . . . . ? C9 C10 C11 C12 -1.3(6) . . . . ? C10 C11 C12 C13 0.6(6) . . . . ? C11 C12 C13 C8 0.6(5) . . . . ? C9 C8 C13 C12 -1.0(4) . . . . ? C7 C8 C13 C12 174.9(3) . . . . ? C7 N3 C14 C15 -53.8(4) . . . . ? Al1 N3 C14 C15 127.7(3) . . . . ? C7 N3 C14 C19 129.0(3) . . . . ? Al1 N3 C14 C19 -49.5(4) . . . . ? N3 C14 C15 C20 0.2(6) . . . . ? C19 C14 C15 C20 177.2(4) . . . . ? N3 C14 C15 C16 -176.6(3) . . . . ? C19 C14 C15 C16 0.4(6) . . . . ? C14 C15 C16 C17 0.9(6) . . . . ? C20 C15 C16 C17 -176.0(5) . . . . ? C15 C16 C17 C18 -2.1(9) . . . . ? C16 C17 C18 C19 1.8(10) . . . . ? C17 C18 C19 C14 -0.3(8) . . . . ? C15 C14 C19 C18 -0.7(7) . . . . ? N3 C14 C19 C18 176.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.619 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.043 # Attachment '10a.cif' data_071025a _database_code_depnum_ccdc_archive 'CCDC 687141' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Al N3 O' _chemical_formula_weight 403.49 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.4120(10) _cell_length_b 24.654(2) _cell_length_c 12.7840(15) _cell_angle_alpha 90.00 _cell_angle_beta 96.660(2) _cell_angle_gamma 90.00 _cell_volume 2320.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2777 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 25.205 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9760 _exptl_absorpt_correction_T_max 0.9812 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12080 _diffrn_reflns_av_R_equivalents 0.0570 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4072 _reflns_number_gt 2376 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^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 0.0021(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4072 _refine_ls_number_parameters 267 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1034 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1348 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Al1 Al 0.30200(12) 0.14290(3) 0.39939(6) 0.0570(3) Uani 1 1 d . . . N1 N 0.2803(3) 0.08698(8) 0.29852(15) 0.0510(6) Uani 1 1 d . . . N2 N 0.2362(3) 0.03955(9) 0.50622(15) 0.0494(5) Uani 1 1 d . . . N3 N 0.2203(3) 0.09513(9) 0.51058(17) 0.0558(6) Uani 1 1 d . . . O1 O 0.3860(3) 0.17752(7) 0.21276(15) 0.0726(6) Uani 1 1 d . A . C1 C 0.2598(4) 0.14740(11) 0.1492(2) 0.0560(7) Uani 1 1 d . . . C2 C 0.2072(4) 0.09919(10) 0.19374(19) 0.0498(7) Uani 1 1 d . . . C3 C 0.0788(4) 0.06704(11) 0.1343(2) 0.0592(7) Uani 1 1 d . . . H3 H 0.0415 0.0346 0.1622 0.071 Uiso 1 1 calc R . . C4 C 0.0065(4) 0.08265(13) 0.0347(2) 0.0695(8) Uani 1 1 d . . . H4 H -0.0765 0.0603 -0.0047 0.083 Uiso 1 1 calc R . . C5 C 0.0560(4) 0.13081(14) -0.0065(2) 0.0735(9) Uani 1 1 d . . . H5 H 0.0043 0.1415 -0.0730 0.088 Uiso 1 1 calc R . . C6 C 0.1825(5) 0.16359(12) 0.0504(2) 0.0707(9) Uani 1 1 d . . . H6 H 0.2157 0.1964 0.0225 0.085 Uiso 1 1 calc R . . C7 C 0.5102(5) 0.21202(13) 0.1647(3) 0.0789(9) Uani 1 1 d D . . H7 H 0.4561 0.2293 0.0994 0.095 Uiso 0.44(3) 1 d PR A 1 H7' H 0.4337 0.2337 0.1127 0.095 Uiso 0.56(3) 1 d PR A 2 C8 C 0.653(4) 0.1698(10) 0.146(3) 0.124(6) Uani 0.44(3) 1 d PD A 1 H8A H 0.6026 0.1443 0.0937 0.187 Uiso 0.44(3) 1 calc PR A 1 H8B H 0.6908 0.1509 0.2105 0.187 Uiso 0.44(3) 1 calc PR A 1 H8C H 0.7561 0.1874 0.1218 0.187 Uiso 0.44(3) 1 calc PR A 1 C8' C 0.650(3) 0.1864(11) 0.105(2) 0.124(6) Uani 0.56(3) 1 d PD A 2 H8'1 H 0.5924 0.1610 0.0544 0.187 Uiso 0.56(3) 1 calc PR A 2 H8'2 H 0.7384 0.1677 0.1525 0.187 Uiso 0.56(3) 1 calc PR A 2 H8'3 H 0.7098 0.2140 0.0681 0.187 Uiso 0.56(3) 1 calc PR A 2 C9 C 0.5876(5) 0.25156(14) 0.2469(3) 0.1053(13) Uani 1 1 d D A . H9A H 0.4904 0.2699 0.2758 0.158 Uiso 1 1 calc R . . H9B H 0.6614 0.2776 0.2157 0.158 Uiso 1 1 calc R . . H9C H 0.6606 0.2325 0.3020 0.158 Uiso 1 1 calc R . . C10 C 0.3026(3) 0.01275(10) 0.42120(18) 0.0494(6) Uani 1 1 d . . . H10 H 0.3433 -0.0226 0.4334 0.059 Uiso 1 1 calc R . . C11 C 0.3135(3) 0.03275(10) 0.32473(18) 0.0467(6) Uani 1 1 d . . . C12 C 0.3866(3) -0.00435(10) 0.24790(19) 0.0486(6) Uani 1 1 d . . . C13 C 0.3418(4) -0.05898(12) 0.2437(2) 0.0624(8) Uani 1 1 d . . . H13 H 0.2590 -0.0725 0.2865 0.075 Uiso 1 1 calc R . . C14 C 0.4197(5) -0.09345(13) 0.1761(3) 0.0792(10) Uani 1 1 d . . . H14 H 0.3890 -0.1300 0.1738 0.095 Uiso 1 1 calc R . . C15 C 0.5419(5) -0.07396(16) 0.1125(3) 0.0839(11) Uani 1 1 d . . . H15 H 0.5940 -0.0974 0.0675 0.101 Uiso 1 1 calc R . . C16 C 0.5873(4) -0.02009(15) 0.1151(2) 0.0726(9) Uani 1 1 d . . . H16 H 0.6710 -0.0070 0.0725 0.087 Uiso 1 1 calc R . . C17 C 0.5087(4) 0.01475(12) 0.18113(19) 0.0578(7) Uani 1 1 d . . . H17 H 0.5375 0.0515 0.1812 0.069 Uiso 1 1 calc R . . C18 C 0.1851(4) -0.04360(11) 0.6090(2) 0.0628(8) Uani 1 1 d . . . H18A H 0.1279 -0.0610 0.5466 0.094 Uiso 1 1 calc R . . H18B H 0.1202 -0.0524 0.6675 0.094 Uiso 1 1 calc R . . H18C H 0.3083 -0.0560 0.6231 0.094 Uiso 1 1 calc R . . C19 C 0.1833(4) 0.01585(12) 0.59320(19) 0.0545(7) Uani 1 1 d . . . C20 C 0.1314(4) 0.05700(12) 0.6553(2) 0.0612(8) Uani 1 1 d . . . H20 H 0.0878 0.0533 0.7202 0.073 Uiso 1 1 calc R . . C21 C 0.1563(4) 0.10523(12) 0.6029(2) 0.0623(8) Uani 1 1 d . . . C22 C 0.1209(5) 0.16188(13) 0.6382(3) 0.0947(11) Uani 1 1 d . . . H22A H 0.2042 0.1864 0.6106 0.142 Uiso 1 1 calc R . . H22B H 0.1373 0.1634 0.7138 0.142 Uiso 1 1 calc R . . H22C H -0.0013 0.1721 0.6129 0.142 Uiso 1 1 calc R . . C23 C 0.1099(5) 0.19762(12) 0.3729(2) 0.0817(10) Uani 1 1 d . . . H23A H 0.1627 0.2317 0.3568 0.123 Uiso 1 1 calc R . . H23B H 0.0482 0.2016 0.4345 0.123 Uiso 1 1 calc R . . H23C H 0.0248 0.1864 0.3146 0.123 Uiso 1 1 calc R . . C24 C 0.5445(4) 0.16176(13) 0.4678(2) 0.0766(9) Uani 1 1 d . . . H24A H 0.5694 0.1415 0.5320 0.115 Uiso 1 1 calc R . . H24B H 0.5492 0.1999 0.4833 0.115 Uiso 1 1 calc R . . H24C H 0.6336 0.1531 0.4215 0.115 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 0.0602(6) 0.0528(5) 0.0575(5) -0.0077(4) 0.0044(4) -0.0022(4) N1 0.0608(14) 0.0468(13) 0.0441(12) 0.0020(10) 0.0005(10) -0.0004(10) N2 0.0459(13) 0.0608(14) 0.0407(12) -0.0009(10) 0.0015(10) -0.0033(11) N3 0.0561(14) 0.0592(15) 0.0520(13) -0.0093(11) 0.0053(11) -0.0061(11) O1 0.0887(16) 0.0617(12) 0.0666(13) 0.0037(10) 0.0055(11) -0.0150(11) C1 0.0630(19) 0.0529(17) 0.0517(16) 0.0003(14) 0.0054(14) 0.0046(14) C2 0.0541(17) 0.0501(15) 0.0453(15) -0.0011(12) 0.0062(12) 0.0067(13) C3 0.0566(18) 0.0644(18) 0.0551(17) -0.0001(14) 0.0006(14) -0.0002(15) C4 0.061(2) 0.088(2) 0.0570(18) -0.0016(17) -0.0038(15) 0.0055(17) C5 0.073(2) 0.094(3) 0.0507(17) 0.0083(17) -0.0027(16) 0.0135(19) C6 0.086(2) 0.066(2) 0.0607(19) 0.0135(16) 0.0127(17) 0.0101(17) C7 0.090(2) 0.063(2) 0.084(2) 0.0080(18) 0.0132(19) -0.0130(19) C8 0.106(4) 0.124(11) 0.157(19) -0.037(9) 0.071(10) -0.022(7) C8' 0.106(4) 0.124(11) 0.157(19) -0.037(9) 0.071(10) -0.022(7) C9 0.122(3) 0.070(2) 0.124(3) -0.005(2) 0.014(3) -0.029(2) C10 0.0458(16) 0.0526(15) 0.0485(16) -0.0017(12) 0.0006(12) 0.0026(13) C11 0.0431(15) 0.0518(16) 0.0436(14) -0.0029(12) -0.0020(11) 0.0001(12) C12 0.0495(17) 0.0505(16) 0.0438(14) -0.0009(12) -0.0032(12) 0.0041(13) C13 0.0636(19) 0.0605(18) 0.0625(18) -0.0015(15) 0.0043(15) 0.0056(15) C14 0.087(3) 0.064(2) 0.083(2) -0.0154(18) -0.006(2) 0.0164(18) C15 0.085(3) 0.101(3) 0.064(2) -0.023(2) -0.0002(19) 0.030(2) C16 0.066(2) 0.105(3) 0.0472(17) -0.0027(17) 0.0054(14) 0.0158(19) C17 0.0580(18) 0.0717(18) 0.0425(15) 0.0012(14) 0.0009(13) 0.0070(15) C18 0.0589(19) 0.075(2) 0.0544(17) 0.0095(15) 0.0045(14) 0.0000(15) C19 0.0423(16) 0.0767(19) 0.0428(15) 0.0022(14) -0.0028(12) -0.0024(14) C20 0.0529(18) 0.086(2) 0.0453(16) -0.0010(16) 0.0070(13) -0.0009(16) C21 0.0574(19) 0.074(2) 0.0547(17) -0.0122(16) 0.0035(14) -0.0041(15) C22 0.124(3) 0.087(2) 0.078(2) -0.0262(19) 0.030(2) -0.005(2) C23 0.094(3) 0.074(2) 0.077(2) -0.0077(17) 0.0092(18) 0.0199(18) C24 0.075(2) 0.079(2) 0.075(2) -0.0125(16) 0.0074(17) -0.0135(17) _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 N1 1.882(2) . ? Al1 C24 1.961(3) . ? Al1 C23 1.962(3) . ? Al1 N3 1.994(2) . ? Al1 O1 2.675(2) . ? N1 C11 1.393(3) . ? N1 C2 1.418(3) . ? N2 C19 1.354(3) . ? N2 N3 1.377(3) . ? N2 C10 1.409(3) . ? N3 C21 1.345(3) . ? O1 C1 1.383(3) . ? O1 C7 1.442(3) . ? C1 C6 1.383(4) . ? C1 C2 1.393(3) . ? C2 C3 1.394(3) . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C4 C5 1.366(4) . ? C4 H4 0.9300 . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C9 1.498(4) . ? C7 C8' 1.502(10) . ? C7 C8 1.525(13) . ? C7 H7 0.9800 . ? C7 H7' 0.9800 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8' H8'1 0.9600 . ? C8' H8'2 0.9600 . ? C8' H8'3 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.339(3) . ? C10 H10 0.9300 . ? C11 C12 1.489(3) . ? C12 C13 1.387(4) . ? C12 C17 1.396(4) . ? C13 C14 1.386(4) . ? C13 H13 0.9300 . ? C14 C15 1.372(5) . ? C14 H14 0.9300 . ? C15 C16 1.370(4) . ? C15 H15 0.9300 . ? C16 C17 1.380(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.479(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.370(4) . ? C20 C21 1.387(4) . ? C20 H20 0.9300 . ? C21 C22 1.500(4) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Al1 C24 118.70(12) . . ? N1 Al1 C23 112.53(12) . . ? C24 Al1 C23 121.52(14) . . ? N1 Al1 N3 92.70(9) . . ? C24 Al1 N3 99.25(12) . . ? C23 Al1 N3 104.75(13) . . ? N1 Al1 O1 68.45(8) . . ? C24 Al1 O1 91.48(11) . . ? C23 Al1 O1 82.31(11) . . ? N3 Al1 O1 161.10(8) . . ? C11 N1 C2 117.93(19) . . ? C11 N1 Al1 122.65(15) . . ? C2 N1 Al1 119.00(16) . . ? C19 N2 N3 111.2(2) . . ? C19 N2 C10 126.3(2) . . ? N3 N2 C10 122.5(2) . . ? C21 N3 N2 105.1(2) . . ? C21 N3 Al1 133.1(2) . . ? N2 N3 Al1 121.63(16) . . ? C1 O1 C7 119.2(2) . . ? C1 O1 Al1 98.12(15) . . ? C7 O1 Al1 142.62(17) . . ? O1 C1 C6 124.2(3) . . ? O1 C1 C2 114.9(2) . . ? C6 C1 C2 120.9(3) . . ? C1 C2 C3 117.9(2) . . ? C1 C2 N1 118.2(2) . . ? C3 C2 N1 123.8(2) . . ? C4 C3 C2 120.9(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 119.7(3) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 C9 107.2(3) . . ? O1 C7 C8' 118.9(11) . . ? C9 C7 C8' 113.7(12) . . ? O1 C7 C8 98.8(12) . . ? C9 C7 C8 109.8(16) . . ? C8' C7 C8 25.5(13) . . ? O1 C7 H7 113.6 . . ? C9 C7 H7 113.6 . . ? C8' C7 H7 89.2 . . ? C8 C7 H7 112.7 . . ? O1 C7 H7' 105.3 . . ? C9 C7 H7' 105.4 . . ? C8' C7 H7' 105.2 . . ? C8 C7 H7' 128.6 . . ? H7 C7 H7' 16.0 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C8' H8'1 109.5 . . ? C7 C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? C7 C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N2 127.0(2) . . ? C11 C10 H10 116.5 . . ? N2 C10 H10 116.5 . . ? C10 C11 N1 123.2(2) . . ? C10 C11 C12 116.5(2) . . ? N1 C11 C12 119.9(2) . . ? C13 C12 C17 118.3(3) . . ? C13 C12 C11 121.2(2) . . ? C17 C12 C11 120.5(2) . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 119.9(3) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.9(3) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C20 106.5(2) . . ? N2 C19 C18 122.7(2) . . ? C20 C19 C18 130.8(3) . . ? C19 C20 C21 107.1(3) . . ? C19 C20 H20 126.5 . . ? C21 C20 H20 126.5 . . ? N3 C21 C20 110.2(3) . . ? N3 C21 C22 121.9(3) . . ? C20 C21 C22 128.0(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? Al1 C23 H23A 109.5 . . ? Al1 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? Al1 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? Al1 C24 H24A 109.5 . . ? Al1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? Al1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C24 Al1 N1 C11 68.9(2) . . . . ? C23 Al1 N1 C11 -140.4(2) . . . . ? N3 Al1 N1 C11 -33.2(2) . . . . ? O1 Al1 N1 C11 148.3(2) . . . . ? C24 Al1 N1 C2 -118.7(2) . . . . ? C23 Al1 N1 C2 32.0(2) . . . . ? N3 Al1 N1 C2 139.2(2) . . . . ? O1 Al1 N1 C2 -39.33(18) . . . . ? C19 N2 N3 C21 0.1(3) . . . . ? C10 N2 N3 C21 -178.9(2) . . . . ? C19 N2 N3 Al1 175.97(16) . . . . ? C10 N2 N3 Al1 -3.1(3) . . . . ? N1 Al1 N3 C21 -162.1(2) . . . . ? C24 Al1 N3 C21 78.2(3) . . . . ? C23 Al1 N3 C21 -48.0(3) . . . . ? O1 Al1 N3 C21 -158.0(2) . . . . ? N1 Al1 N3 N2 23.41(19) . . . . ? C24 Al1 N3 N2 -96.24(19) . . . . ? C23 Al1 N3 N2 137.56(19) . . . . ? O1 Al1 N3 N2 27.5(4) . . . . ? N1 Al1 O1 C1 36.24(15) . . . . ? C24 Al1 O1 C1 156.65(17) . . . . ? C23 Al1 O1 C1 -81.73(18) . . . . ? N3 Al1 O1 C1 31.8(3) . . . . ? N1 Al1 O1 C7 -141.2(3) . . . . ? C24 Al1 O1 C7 -20.8(3) . . . . ? C23 Al1 O1 C7 100.9(3) . . . . ? N3 Al1 O1 C7 -145.6(3) . . . . ? C7 O1 C1 C6 -31.4(4) . . . . ? Al1 O1 C1 C6 150.4(3) . . . . ? C7 O1 C1 C2 151.4(3) . . . . ? Al1 O1 C1 C2 -26.8(2) . . . . ? O1 C1 C2 C3 179.4(2) . . . . ? C6 C1 C2 C3 2.1(4) . . . . ? O1 C1 C2 N1 2.4(3) . . . . ? C6 C1 C2 N1 -174.9(2) . . . . ? C11 N1 C2 C1 -146.0(2) . . . . ? Al1 N1 C2 C1 41.2(3) . . . . ? C11 N1 C2 C3 37.2(4) . . . . ? Al1 N1 C2 C3 -135.6(2) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? N1 C2 C3 C4 176.7(2) . . . . ? C2 C3 C4 C5 -1.8(4) . . . . ? C3 C4 C5 C6 1.7(5) . . . . ? C4 C5 C6 C1 0.3(5) . . . . ? O1 C1 C6 C5 -179.3(3) . . . . ? C2 C1 C6 C5 -2.2(4) . . . . ? C1 O1 C7 C9 162.6(3) . . . . ? Al1 O1 C7 C9 -20.3(4) . . . . ? C1 O1 C7 C8' -66.7(15) . . . . ? Al1 O1 C7 C8' 110.4(15) . . . . ? C1 O1 C7 C8 -83.4(17) . . . . ? Al1 O1 C7 C8 93.6(17) . . . . ? C19 N2 C10 C11 162.3(3) . . . . ? N3 N2 C10 C11 -18.8(4) . . . . ? N2 C10 C11 N1 8.6(4) . . . . ? N2 C10 C11 C12 -179.0(2) . . . . ? C2 N1 C11 C10 -149.1(2) . . . . ? Al1 N1 C11 C10 23.4(3) . . . . ? C2 N1 C11 C12 38.7(3) . . . . ? Al1 N1 C11 C12 -148.79(18) . . . . ? C10 C11 C12 C13 39.2(3) . . . . ? N1 C11 C12 C13 -148.1(2) . . . . ? C10 C11 C12 C17 -138.0(2) . . . . ? N1 C11 C12 C17 34.7(3) . . . . ? C17 C12 C13 C14 1.2(4) . . . . ? C11 C12 C13 C14 -176.1(2) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C16 -0.2(5) . . . . ? C14 C15 C16 C17 -0.6(5) . . . . ? C15 C16 C17 C12 1.8(4) . . . . ? C13 C12 C17 C16 -2.0(4) . . . . ? C11 C12 C17 C16 175.3(2) . . . . ? N3 N2 C19 C20 0.1(3) . . . . ? C10 N2 C19 C20 179.1(2) . . . . ? N3 N2 C19 C18 179.6(2) . . . . ? C10 N2 C19 C18 -1.4(4) . . . . ? N2 C19 C20 C21 -0.4(3) . . . . ? C18 C19 C20 C21 -179.7(3) . . . . ? N2 N3 C21 C20 -0.4(3) . . . . ? Al1 N3 C21 C20 -175.50(19) . . . . ? N2 N3 C21 C22 179.6(3) . . . . ? Al1 N3 C21 C22 4.4(4) . . . . ? C19 C20 C21 N3 0.5(3) . . . . ? C19 C20 C21 C22 -179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.177 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.034 # Attachment '10d.cif' data_071004c _database_code_depnum_ccdc_archive 'CCDC 687142' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H30 Al N3' _chemical_formula_weight 387.49 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.4350(14) _cell_length_b 20.454(2) _cell_length_c 13.1771(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.580(2) _cell_angle_gamma 90.00 _cell_volume 2266.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1787 _cell_measurement_theta_min 2.524 _cell_measurement_theta_max 19.099 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.136 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9738 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11694 _diffrn_reflns_av_R_equivalents 0.0529 _diffrn_reflns_av_sigmaI/netI 0.1202 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3983 _reflns_number_gt 2103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.4809P] 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 3983 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1224 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.2104 _refine_ls_wR_factor_gt 0.1434 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.07694(14) 0.16207(6) 0.21304(8) 0.0539(4) Uani 1 1 d . A . N1 N -0.0366(4) 0.19079(15) 0.3278(2) 0.0535(8) Uani 1 1 d . . . N2 N -0.1249(3) 0.14793(15) 0.3808(2) 0.0482(8) Uani 1 1 d . . . N3 N 0.0896(3) 0.07414(14) 0.2537(2) 0.0452(7) Uani 1 1 d . . . C1 C 0.0102(6) 0.3098(2) 0.3270(4) 0.0896(15) Uani 1 1 d . . . H1A H 0.1239 0.3059 0.3354 0.134 Uiso 1 1 calc R . . H1B H -0.0226 0.3474 0.3635 0.134 Uiso 1 1 calc R . . H1C H -0.0232 0.3145 0.2560 0.134 Uiso 1 1 calc R . . C2 C -0.0631(5) 0.25039(19) 0.3672(3) 0.0619(11) Uani 1 1 d . . . C3 C -0.1646(5) 0.2446(2) 0.4431(3) 0.0679(12) Uani 1 1 d . . . H3 H -0.2005 0.2786 0.4822 0.081 Uiso 1 1 calc R . . C4 C -0.2034(5) 0.18004(19) 0.4512(3) 0.0542(10) Uani 1 1 d . . . C5 C -0.3067(5) 0.1461(2) 0.5203(3) 0.0714(12) Uani 1 1 d . . . H5A H -0.3559 0.1777 0.5615 0.107 Uiso 1 1 calc R . . H5B H -0.2437 0.1166 0.5635 0.107 Uiso 1 1 calc R . . H5C H -0.3875 0.1220 0.4808 0.107 Uiso 1 1 calc R . . C6 C -0.1273(4) 0.08015(17) 0.3623(3) 0.0469(9) Uani 1 1 d . . . H6 H -0.2095 0.0566 0.3880 0.056 Uiso 1 1 calc R . . C7 C -0.0231(4) 0.04586(18) 0.3112(2) 0.0433(8) Uani 1 1 d . . . C8 C -0.0451(4) -0.02646(17) 0.3087(2) 0.0431(8) Uani 1 1 d . . . C9 C -0.0908(4) -0.06048(19) 0.3925(3) 0.0518(9) Uani 1 1 d . . . H9 H -0.1030 -0.0380 0.4528 0.062 Uiso 1 1 calc R . . C10 C -0.1189(5) -0.1273(2) 0.3885(3) 0.0633(11) Uani 1 1 d . . . H10 H -0.1503 -0.1492 0.4454 0.076 Uiso 1 1 calc R . . C11 C -0.1002(5) -0.1610(2) 0.3004(4) 0.0736(12) Uani 1 1 d . . . H11 H -0.1192 -0.2057 0.2973 0.088 Uiso 1 1 calc R . . C12 C -0.0540(5) -0.1289(2) 0.2177(4) 0.0745(13) Uani 1 1 d . . . H12 H -0.0399 -0.1520 0.1583 0.089 Uiso 1 1 calc R . . C13 C -0.0274(4) -0.0621(2) 0.2205(3) 0.0573(10) Uani 1 1 d . . . H13 H 0.0026 -0.0408 0.1627 0.069 Uiso 1 1 calc R . . C14 C 0.2369(4) 0.03976(18) 0.2506(3) 0.0477(9) Uani 1 1 d . . . C15 C 0.3053(4) 0.0316(2) 0.1584(3) 0.0588(10) Uani 1 1 d . . . C16 C 0.4529(5) 0.0014(2) 0.1605(4) 0.0746(13) Uani 1 1 d . . . H16 H 0.5004 -0.0035 0.0997 0.090 Uiso 1 1 calc R . . C17 C 0.5313(5) -0.0213(2) 0.2481(4) 0.0711(12) Uani 1 1 d . . . H17 H 0.6297 -0.0416 0.2464 0.085 Uiso 1 1 calc R . . C18 C 0.4634(4) -0.0139(2) 0.3386(3) 0.0649(12) Uani 1 1 d . . . H18 H 0.5152 -0.0292 0.3989 0.078 Uiso 1 1 calc R . . C19 C 0.3176(4) 0.01639(19) 0.3391(3) 0.0532(10) Uani 1 1 d . . . H19 H 0.2720 0.0214 0.4006 0.064 Uiso 1 1 calc R . . C20 C 0.2223(5) 0.0528(3) 0.0578(3) 0.0835(15) Uani 1 1 d . . . H20A H 0.1097 0.0466 0.0593 0.125 Uiso 1 1 calc R . . H20B H 0.2604 0.0271 0.0038 0.125 Uiso 1 1 calc R . . H20C H 0.2440 0.0982 0.0464 0.125 Uiso 1 1 calc R . . C21 C 0.2896(5) 0.2019(2) 0.2233(3) 0.0728(13) Uani 1 1 d . . . H21A H 0.3533 0.1806 0.1749 0.087 Uiso 1 1 calc R . . H21B H 0.2794 0.2475 0.2039 0.087 Uiso 1 1 calc R . . C22 C 0.3781(6) 0.1978(3) 0.3291(4) 0.0999(18) Uani 1 1 d . . . H22A H 0.3170 0.2193 0.3777 0.150 Uiso 1 1 calc R . . H22B H 0.4798 0.2188 0.3280 0.150 Uiso 1 1 calc R . . H22C H 0.3932 0.1528 0.3480 0.150 Uiso 1 1 calc R . . C23 C -0.0730(6) 0.1814(3) 0.0959(3) 0.0791(14) Uani 1 1 d . . . H23A H -0.0869 0.2284 0.0909 0.095 Uiso 0.76(3) 1 calc PR A 1 H23B H -0.0275 0.1667 0.0346 0.095 Uiso 0.76(3) 1 calc PR A 1 H23C H -0.1301 0.2209 0.1114 0.095 Uiso 0.24(3) 1 d PR A 2 H23D H -0.0114 0.1917 0.0389 0.095 Uiso 0.24(3) 1 d PR A 2 C24 C -0.2371(18) 0.1494(9) 0.1010(14) 0.120(5) Uani 0.76(3) 1 d P A 1 H24A H -0.3081 0.1651 0.0458 0.179 Uiso 0.76(3) 1 calc PR A 1 H24B H -0.2789 0.1602 0.1645 0.179 Uiso 0.76(3) 1 calc PR A 1 H24C H -0.2268 0.1028 0.0958 0.179 Uiso 0.76(3) 1 calc PR A 1 C24' C -0.193(6) 0.133(3) 0.062(4) 0.120(5) Uani 0.24(3) 1 d P A 2 H24D H -0.2744 0.1314 0.1087 0.179 Uiso 0.24(3) 1 calc PR A 2 H24E H -0.1444 0.0907 0.0581 0.179 Uiso 0.24(3) 1 calc PR A 2 H24F H -0.2403 0.1449 -0.0046 0.179 Uiso 0.24(3) 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 0.0572(7) 0.0559(8) 0.0484(7) 0.0111(5) 0.0029(5) -0.0012(6) N1 0.063(2) 0.0452(19) 0.0527(18) 0.0039(15) 0.0032(15) -0.0038(16) N2 0.0515(17) 0.0457(19) 0.0479(17) -0.0005(14) 0.0065(14) 0.0041(15) N3 0.0396(16) 0.0500(19) 0.0469(16) 0.0029(14) 0.0090(12) 0.0023(14) C1 0.119(4) 0.046(3) 0.103(4) 0.006(3) 0.003(3) -0.008(3) C2 0.078(3) 0.041(2) 0.066(3) 0.001(2) 0.000(2) 0.001(2) C3 0.085(3) 0.051(3) 0.068(3) -0.005(2) 0.006(2) 0.014(2) C4 0.064(2) 0.049(2) 0.049(2) -0.0034(18) 0.0049(18) 0.015(2) C5 0.077(3) 0.073(3) 0.067(3) -0.005(2) 0.027(2) 0.012(2) C6 0.048(2) 0.041(2) 0.052(2) -0.0013(17) 0.0084(16) -0.0007(18) C7 0.0409(19) 0.047(2) 0.0422(19) 0.0011(16) 0.0041(15) 0.0003(17) C8 0.0369(18) 0.045(2) 0.047(2) -0.0016(17) 0.0035(15) 0.0032(16) C9 0.053(2) 0.048(2) 0.054(2) 0.0010(18) 0.0034(17) 0.0019(19) C10 0.061(3) 0.052(3) 0.076(3) 0.013(2) 0.003(2) -0.002(2) C11 0.073(3) 0.047(3) 0.099(4) -0.007(3) 0.002(3) 0.002(2) C12 0.075(3) 0.064(3) 0.086(3) -0.024(3) 0.013(2) 0.000(3) C13 0.056(2) 0.058(3) 0.059(2) -0.009(2) 0.0079(18) -0.001(2) C14 0.044(2) 0.048(2) 0.051(2) -0.0057(18) 0.0098(16) -0.0014(17) C15 0.052(2) 0.070(3) 0.055(2) -0.006(2) 0.0128(18) 0.000(2) C16 0.055(3) 0.096(4) 0.076(3) -0.017(3) 0.021(2) 0.000(3) C17 0.044(2) 0.073(3) 0.097(3) -0.015(3) 0.011(2) 0.005(2) C18 0.044(2) 0.066(3) 0.084(3) 0.002(2) -0.005(2) 0.001(2) C19 0.047(2) 0.055(2) 0.058(2) 0.0067(19) 0.0062(17) -0.0002(19) C20 0.085(3) 0.118(4) 0.050(2) -0.002(3) 0.017(2) 0.011(3) C21 0.075(3) 0.068(3) 0.076(3) 0.020(2) 0.009(2) -0.008(2) C22 0.094(4) 0.093(4) 0.106(4) 0.031(3) -0.030(3) -0.031(3) C23 0.087(3) 0.087(4) 0.061(3) 0.014(2) -0.004(2) 0.007(3) C24 0.094(8) 0.169(11) 0.090(9) 0.001(8) -0.024(6) 0.003(7) C24' 0.094(8) 0.169(11) 0.090(9) 0.001(8) -0.024(6) 0.003(7) _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 N3 1.877(3) . ? Al1 N1 1.945(3) . ? Al1 C23 1.956(4) . ? Al1 C21 1.965(4) . ? N1 C2 1.350(5) . ? N1 N2 1.376(4) . ? N2 C4 1.352(4) . ? N2 C6 1.408(4) . ? N3 C7 1.389(4) . ? N3 C14 1.431(4) . ? C1 C2 1.480(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.373(6) . ? C3 C4 1.366(5) . ? C3 H3 0.9300 . ? C4 C5 1.483(5) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.346(4) . ? C6 H6 0.9300 . ? C7 C8 1.491(5) . ? C8 C9 1.386(5) . ? C8 C13 1.389(5) . ? C9 C10 1.388(5) . ? C9 H9 0.9300 . ? C10 C11 1.369(6) . ? C10 H10 0.9300 . ? C11 C12 1.356(6) . ? C11 H11 0.9300 . ? C12 C13 1.385(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.388(5) . ? C14 C15 1.396(5) . ? C15 C16 1.388(6) . ? C15 C20 1.513(5) . ? C16 C17 1.365(6) . ? C16 H16 0.9300 . ? C17 C18 1.372(6) . ? C17 H17 0.9300 . ? C18 C19 1.378(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.530(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24' 1.47(5) . ? C23 C24 1.538(14) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? C23 H23D 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C24' H24D 0.9600 . ? C24' H24E 0.9600 . ? C24' H24F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Al1 N1 95.04(13) . . ? N3 Al1 C23 115.94(18) . . ? N1 Al1 C23 103.00(17) . . ? N3 Al1 C21 110.28(16) . . ? N1 Al1 C21 108.96(17) . . ? C23 Al1 C21 119.98(19) . . ? C2 N1 N2 105.5(3) . . ? C2 N1 Al1 132.7(3) . . ? N2 N1 Al1 121.5(2) . . ? C4 N2 N1 110.7(3) . . ? C4 N2 C6 126.6(3) . . ? N1 N2 C6 122.7(3) . . ? C7 N3 C14 116.4(3) . . ? C7 N3 Al1 121.9(2) . . ? C14 N3 Al1 119.5(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.5(4) . . ? N1 C2 C1 121.1(4) . . ? C3 C2 C1 129.4(4) . . ? C4 C3 C2 107.9(4) . . ? C4 C3 H3 126.1 . . ? C2 C3 H3 126.0 . . ? N2 C4 C3 106.4(3) . . ? N2 C4 C5 122.6(4) . . ? C3 C4 C5 131.0(4) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N2 126.8(3) . . ? C7 C6 H6 116.6 . . ? N2 C6 H6 116.6 . . ? C6 C7 N3 124.0(3) . . ? C6 C7 C8 116.3(3) . . ? N3 C7 C8 119.3(3) . . ? C9 C8 C13 117.3(4) . . ? C9 C8 C7 121.4(3) . . ? C13 C8 C7 121.2(3) . . ? C8 C9 C10 121.4(4) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C11 C10 C9 119.8(4) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 120.8(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 120.8(4) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C19 C14 C15 118.8(3) . . ? C19 C14 N3 120.9(3) . . ? C15 C14 N3 120.3(3) . . ? C16 C15 C14 117.9(4) . . ? C16 C15 C20 119.8(4) . . ? C14 C15 C20 122.3(3) . . ? C17 C16 C15 122.8(4) . . ? C17 C16 H16 118.6 . . ? C15 C16 H16 118.6 . . ? C16 C17 C18 119.3(4) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 119.2(4) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C14 121.9(4) . . ? C18 C19 H19 119.0 . . ? C14 C19 H19 119.0 . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 Al1 114.6(3) . . ? C22 C21 H21A 108.6 . . ? Al1 C21 H21A 108.6 . . ? C22 C21 H21B 108.6 . . ? Al1 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24' C23 C24 28.5(18) . . ? C24' C23 Al1 120(2) . . ? C24 C23 Al1 114.0(6) . . ? C24' C23 H23A 125.0 . . ? C24 C23 H23A 108.7 . . ? Al1 C23 H23A 108.7 . . ? C24' C23 H23B 81.0 . . ? C24 C23 H23B 108.7 . . ? Al1 C23 H23B 108.7 . . ? H23A C23 H23B 107.6 . . ? C24' C23 H23C 106.6 . . ? C24 C23 H23C 83.2 . . ? Al1 C23 H23C 107.6 . . ? H23A C23 H23C 29.6 . . ? H23B C23 H23C 132.0 . . ? C24' C23 H23D 107.9 . . ? C24 C23 H23D 131.7 . . ? Al1 C23 H23D 107.6 . . ? H23A C23 H23D 78.6 . . ? H23B C23 H23D 31.7 . . ? H23C C23 H23D 106.8 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? C23 C24' H24D 109.5 . . ? C23 C24' H24E 109.5 . . ? H24D C24' H24E 109.5 . . ? C23 C24' H24F 109.5 . . ? H24D C24' H24F 109.5 . . ? H24E C24' H24F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Al1 N1 C2 163.9(4) . . . . ? C23 Al1 N1 C2 -78.0(4) . . . . ? C21 Al1 N1 C2 50.5(4) . . . . ? N3 Al1 N1 N2 -23.3(3) . . . . ? C23 Al1 N1 N2 94.8(3) . . . . ? C21 Al1 N1 N2 -136.8(3) . . . . ? C2 N1 N2 C4 -0.2(4) . . . . ? Al1 N1 N2 C4 -174.7(2) . . . . ? C2 N1 N2 C6 -179.4(3) . . . . ? Al1 N1 N2 C6 6.1(4) . . . . ? N1 Al1 N3 C7 28.0(3) . . . . ? C23 Al1 N3 C7 -79.1(3) . . . . ? C21 Al1 N3 C7 140.3(3) . . . . ? N1 Al1 N3 C14 -134.7(3) . . . . ? C23 Al1 N3 C14 118.2(3) . . . . ? C21 Al1 N3 C14 -22.4(3) . . . . ? N2 N1 C2 C3 0.4(4) . . . . ? Al1 N1 C2 C3 174.0(3) . . . . ? N2 N1 C2 C1 -178.6(4) . . . . ? Al1 N1 C2 C1 -5.0(6) . . . . ? N1 C2 C3 C4 -0.4(5) . . . . ? C1 C2 C3 C4 178.4(4) . . . . ? N1 N2 C4 C3 0.0(4) . . . . ? C6 N2 C4 C3 179.1(3) . . . . ? N1 N2 C4 C5 -179.3(3) . . . . ? C6 N2 C4 C5 -0.2(5) . . . . ? C2 C3 C4 N2 0.3(4) . . . . ? C2 C3 C4 C5 179.5(4) . . . . ? C4 N2 C6 C7 -162.8(3) . . . . ? N1 N2 C6 C7 16.3(5) . . . . ? N2 C6 C7 N3 -11.3(5) . . . . ? N2 C6 C7 C8 175.7(3) . . . . ? C14 N3 C7 C6 147.3(3) . . . . ? Al1 N3 C7 C6 -15.9(4) . . . . ? C14 N3 C7 C8 -39.8(4) . . . . ? Al1 N3 C7 C8 157.0(2) . . . . ? C6 C7 C8 C9 -38.0(5) . . . . ? N3 C7 C8 C9 148.6(3) . . . . ? C6 C7 C8 C13 139.1(3) . . . . ? N3 C7 C8 C13 -34.3(5) . . . . ? C13 C8 C9 C10 -0.4(5) . . . . ? C7 C8 C9 C10 176.8(3) . . . . ? C8 C9 C10 C11 0.5(6) . . . . ? C9 C10 C11 C12 0.2(6) . . . . ? C10 C11 C12 C13 -0.9(7) . . . . ? C11 C12 C13 C8 1.0(6) . . . . ? C9 C8 C13 C12 -0.3(5) . . . . ? C7 C8 C13 C12 -177.5(3) . . . . ? C7 N3 C14 C19 -47.5(5) . . . . ? Al1 N3 C14 C19 116.2(3) . . . . ? C7 N3 C14 C15 135.3(4) . . . . ? Al1 N3 C14 C15 -61.1(4) . . . . ? C19 C14 C15 C16 -1.2(6) . . . . ? N3 C14 C15 C16 176.1(4) . . . . ? C19 C14 C15 C20 177.2(4) . . . . ? N3 C14 C15 C20 -5.5(6) . . . . ? C14 C15 C16 C17 1.2(7) . . . . ? C20 C15 C16 C17 -177.2(4) . . . . ? C15 C16 C17 C18 -0.5(7) . . . . ? C16 C17 C18 C19 -0.1(6) . . . . ? C17 C18 C19 C14 0.0(6) . . . . ? C15 C14 C19 C18 0.6(6) . . . . ? N3 C14 C19 C18 -176.7(3) . . . . ? N3 Al1 C21 C22 -56.6(4) . . . . ? N1 Al1 C21 C22 46.4(4) . . . . ? C23 Al1 C21 C22 164.7(4) . . . . ? N3 Al1 C23 C24' 15(3) . . . . ? N1 Al1 C23 C24' -87(3) . . . . ? C21 Al1 C23 C24' 151(3) . . . . ? N3 Al1 C23 C24 46.2(11) . . . . ? N1 Al1 C23 C24 -56.0(10) . . . . ? C21 Al1 C23 C24 -177.2(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.192 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.043 # Attachment '11.cif' data_70715d _database_code_depnum_ccdc_archive 'CCDC 687143' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H36 Al N3' _chemical_formula_weight 417.56 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.977(7) _cell_length_b 18.109(11) _cell_length_c 12.058(7) _cell_angle_alpha 90.00 _cell_angle_beta 108.400(10) _cell_angle_gamma 90.00 _cell_volume 2482(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1036 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.13 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 1.118 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.870279 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11862 _diffrn_reflns_av_R_equivalents 0.2050 _diffrn_reflns_av_sigmaI/netI 0.2852 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4315 _reflns_number_gt 1365 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^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 0.018(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4315 _refine_ls_number_parameters 278 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.2726 _refine_ls_R_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.1983 _refine_ls_wR_factor_gt 0.1613 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.065 _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 0.47603(18) 0.20683(11) 0.02676(17) 0.0533(7) Uani 1 1 d . . . N1 N 0.5310(4) 0.3082(3) 0.0416(4) 0.0437(14) Uani 1 1 d . . . N2 N 0.5457(4) 0.3454(3) 0.1435(5) 0.0495(14) Uani 1 1 d . . . N3 N 0.3754(4) 0.2183(2) 0.1153(4) 0.0419(13) Uani 1 1 d . . . C1 C 0.5660(6) 0.3382(4) -0.1495(5) 0.091(3) Uani 1 1 d . . . H1A H 0.6203 0.2988 -0.1470 0.136 Uiso 1 1 calc R . . H1B H 0.5885 0.3810 -0.1844 0.136 Uiso 1 1 calc R . . H1C H 0.4882 0.3232 -0.1952 0.136 Uiso 1 1 calc R . . C2 C 0.5675(6) 0.3567(4) -0.0256(6) 0.0555(19) Uani 1 1 d . . . C3 C 0.5989(6) 0.4234(4) 0.0332(7) 0.069(2) Uani 1 1 d . . . H3 H 0.6255 0.4656 0.0055 0.083 Uiso 1 1 calc R . . C4 C 0.5831(6) 0.4148(4) 0.1382(6) 0.0530(19) Uani 1 1 d . . . C5 C 0.6057(6) 0.4692(4) 0.2381(5) 0.083(3) Uani 1 1 d . . . H5A H 0.5350 0.4758 0.2584 0.125 Uiso 1 1 calc R . . H5B H 0.6295 0.5157 0.2147 0.125 Uiso 1 1 calc R . . H5C H 0.6669 0.4506 0.3045 0.125 Uiso 1 1 calc R . . C6 C 0.5125(5) 0.3080(3) 0.2349(5) 0.0488(18) Uani 1 1 d . . . H6A H 0.5260 0.3410 0.3013 0.059 Uiso 1 1 calc R . . H6B H 0.5623 0.2651 0.2604 0.059 Uiso 1 1 calc R . . C7 C 0.3832(5) 0.2835(3) 0.1950(5) 0.0401(16) Uani 1 1 d . . . C8 C 0.3098(5) 0.3488(3) 0.1354(6) 0.0406(16) Uani 1 1 d . . . C9 C 0.2662(5) 0.3574(4) 0.0154(6) 0.0519(18) Uani 1 1 d . . . H9 H 0.2839 0.3207 -0.0304 0.062 Uiso 1 1 calc R . . C10 C 0.1991(6) 0.4156(4) -0.0412(6) 0.062(2) Uani 1 1 d . . . H10 H 0.1712 0.4173 -0.1224 0.075 Uiso 1 1 calc R . . C11 C 0.1739(6) 0.4713(5) 0.0240(8) 0.078(2) Uani 1 1 d . . . H11 H 0.1262 0.5103 -0.0133 0.093 Uiso 1 1 calc R . . C12 C 0.2187(7) 0.4700(4) 0.1449(8) 0.084(3) Uani 1 1 d . . . H12 H 0.2067 0.5093 0.1895 0.101 Uiso 1 1 calc R . . C13 C 0.2829(6) 0.4074(4) 0.1980(6) 0.067(2) Uani 1 1 d . . . H13 H 0.3089 0.4048 0.2792 0.080 Uiso 1 1 calc R . . C14 C 0.3564(5) 0.2607(3) 0.3077(5) 0.0505(18) Uani 1 1 d . . . H14A H 0.3788 0.3012 0.3629 0.061 Uiso 1 1 calc R . . H14B H 0.2720 0.2543 0.2885 0.061 Uiso 1 1 calc R . . C15 C 0.4162(5) 0.1907(3) 0.3688(5) 0.065(2) Uani 1 1 d . . . H15A H 0.3919 0.1494 0.3169 0.098 Uiso 1 1 calc R . . H15B H 0.3943 0.1824 0.4378 0.098 Uiso 1 1 calc R . . H15C H 0.5001 0.1964 0.3901 0.098 Uiso 1 1 calc R . . C16 C 0.2697(6) 0.1770(4) 0.0937(5) 0.0454(17) Uani 1 1 d . . . C17 C 0.1612(6) 0.2073(4) 0.0872(4) 0.0533(19) Uani 1 1 d . . . H17 H 0.1552 0.2582 0.0948 0.064 Uiso 1 1 calc R . . C18 C 0.0627(6) 0.1647(5) 0.0699(5) 0.069(2) Uani 1 1 d . . . H18 H -0.0075 0.1870 0.0690 0.082 Uiso 1 1 calc R . . C19 C 0.0651(8) 0.0905(5) 0.0539(6) 0.078(2) Uani 1 1 d . . . H19 H -0.0028 0.0623 0.0401 0.093 Uiso 1 1 calc R . . C20 C 0.1691(8) 0.0583(4) 0.0586(6) 0.066(2) Uani 1 1 d . . . H20 H 0.1717 0.0075 0.0481 0.079 Uiso 1 1 calc R . . C21 C 0.2728(7) 0.0997(4) 0.0787(5) 0.059(2) Uani 1 1 d . . . C22 C 0.3842(7) 0.0588(4) 0.0937(6) 0.090(3) Uani 1 1 d . . . H22A H 0.3995 0.0566 0.0203 0.134 Uiso 1 1 calc R . . H22B H 0.3771 0.0096 0.1203 0.134 Uiso 1 1 calc R . . H22C H 0.4478 0.0837 0.1502 0.134 Uiso 1 1 calc R . . C23 C 0.3821(6) 0.1871(4) -0.1376(5) 0.077(2) Uani 1 1 d . . . H23A H 0.3080 0.1659 -0.1366 0.092 Uiso 1 1 calc R . . H23B H 0.3639 0.2346 -0.1763 0.092 Uiso 1 1 calc R . . C24 C 0.4288(7) 0.1379(4) -0.2157(7) 0.118(3) Uani 1 1 d U . . H24A H 0.5068 0.1533 -0.2110 0.176 Uiso 1 1 calc R . . H24B H 0.3782 0.1418 -0.2950 0.176 Uiso 1 1 calc R . . H24C H 0.4307 0.0875 -0.1901 0.176 Uiso 1 1 calc R . . C25 C 0.6270(6) 0.1529(4) 0.0993(6) 0.082(2) Uani 1 1 d . . . H25A H 0.6513 0.1612 0.1830 0.098 Uiso 1 1 calc R . . H25B H 0.6120 0.1004 0.0863 0.098 Uiso 1 1 calc R . . C26 C 0.7258(7) 0.1729(5) 0.0569(7) 0.127(3) Uani 1 1 d U . . H26A H 0.6990 0.1742 -0.0269 0.190 Uiso 1 1 calc R . . H26B H 0.7873 0.1369 0.0834 0.190 Uiso 1 1 calc R . . H26C H 0.7554 0.2207 0.0867 0.190 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 0.0574(14) 0.0491(13) 0.0602(14) -0.0081(12) 0.0282(11) -0.0024(12) N1 0.042(3) 0.061(4) 0.038(3) -0.008(3) 0.026(3) -0.007(3) N2 0.042(4) 0.065(4) 0.047(4) 0.001(3) 0.022(3) -0.012(3) N3 0.040(3) 0.037(3) 0.054(3) -0.007(3) 0.023(3) -0.011(3) C1 0.109(7) 0.119(7) 0.065(5) -0.002(5) 0.057(5) 0.006(5) C2 0.051(5) 0.074(5) 0.054(5) -0.006(4) 0.034(4) 0.000(4) C3 0.061(5) 0.076(6) 0.076(6) 0.009(5) 0.030(5) -0.001(4) C4 0.054(5) 0.055(5) 0.061(5) -0.006(4) 0.035(4) -0.018(4) C5 0.123(7) 0.066(5) 0.052(5) -0.013(4) 0.015(5) -0.038(5) C6 0.047(4) 0.068(5) 0.036(4) 0.008(3) 0.019(3) -0.011(4) C7 0.041(4) 0.049(4) 0.036(4) -0.004(4) 0.021(3) -0.010(3) C8 0.041(4) 0.050(4) 0.033(4) -0.005(4) 0.015(3) -0.003(3) C9 0.052(5) 0.053(5) 0.052(5) 0.003(4) 0.020(4) -0.002(4) C10 0.053(5) 0.056(5) 0.072(5) 0.007(5) 0.012(4) 0.011(4) C11 0.059(6) 0.072(6) 0.098(7) 0.026(6) 0.019(5) 0.004(4) C12 0.088(7) 0.076(6) 0.099(7) -0.017(6) 0.045(6) 0.030(5) C13 0.070(6) 0.073(6) 0.061(5) -0.012(5) 0.024(4) 0.005(5) C14 0.042(4) 0.072(5) 0.037(4) -0.003(4) 0.011(3) -0.024(4) C15 0.079(5) 0.055(5) 0.053(4) 0.016(4) 0.008(4) -0.017(4) C16 0.050(5) 0.063(5) 0.025(4) 0.005(3) 0.014(3) 0.001(4) C17 0.047(5) 0.077(5) 0.036(4) -0.003(4) 0.014(3) -0.033(5) C18 0.056(5) 0.095(7) 0.057(5) 0.009(5) 0.021(4) -0.022(5) C19 0.069(7) 0.087(7) 0.073(6) -0.008(5) 0.016(5) -0.040(6) C20 0.073(6) 0.056(5) 0.069(5) -0.008(4) 0.024(5) -0.026(5) C21 0.060(6) 0.051(5) 0.060(5) -0.008(4) 0.010(4) 0.000(5) C22 0.110(7) 0.055(5) 0.108(7) -0.016(5) 0.041(6) -0.010(5) C23 0.097(6) 0.085(6) 0.064(5) -0.023(4) 0.048(4) 0.002(5) C24 0.136(7) 0.120(6) 0.099(6) -0.046(5) 0.039(5) 0.000(5) C25 0.082(6) 0.068(5) 0.119(7) 0.008(5) 0.067(5) 0.002(4) C26 0.104(6) 0.141(7) 0.150(7) 0.011(6) 0.062(6) 0.026(5) _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 N3 1.857(5) . ? Al1 N1 1.939(5) . ? Al1 C23 1.978(7) . ? Al1 C25 1.998(7) . ? N1 C2 1.358(7) . ? N1 N2 1.364(6) . ? N2 C4 1.342(7) . ? N2 C6 1.452(6) . ? N3 C16 1.421(7) . ? N3 C7 1.507(6) . ? C1 C2 1.527(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.390(8) . ? C3 C4 1.348(8) . ? C3 H3 0.9300 . ? C4 C5 1.512(8) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.535(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.514(7) . ? C7 C14 1.547(7) . ? C8 C9 1.383(7) . ? C8 C13 1.397(8) . ? C9 C10 1.371(7) . ? C9 H9 0.9300 . ? C10 C11 1.369(9) . ? C10 H10 0.9300 . ? C11 C12 1.386(9) . ? C11 H11 0.9300 . ? C12 C13 1.406(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.526(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.390(8) . ? C16 C21 1.413(8) . ? C17 C18 1.370(7) . ? C17 H17 0.9300 . ? C18 C19 1.359(9) . ? C18 H18 0.9300 . ? C19 C20 1.360(9) . ? C19 H19 0.9300 . ? C20 C21 1.405(9) . ? C20 H20 0.9300 . ? C21 C22 1.487(8) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C24 1.525(8) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.474(8) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Al1 N1 96.0(2) . . ? N3 Al1 C23 109.2(3) . . ? N1 Al1 C23 109.4(3) . . ? N3 Al1 C25 117.7(3) . . ? N1 Al1 C25 100.9(3) . . ? C23 Al1 C25 120.0(3) . . ? C2 N1 N2 104.1(5) . . ? C2 N1 Al1 136.2(5) . . ? N2 N1 Al1 119.6(4) . . ? C4 N2 N1 111.7(5) . . ? C4 N2 C6 130.4(6) . . ? N1 N2 C6 117.8(5) . . ? C16 N3 C7 113.6(5) . . ? C16 N3 Al1 122.5(4) . . ? C7 N3 Al1 122.3(4) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 110.2(6) . . ? N1 C2 C1 122.3(7) . . ? C3 C2 C1 127.4(7) . . ? C4 C3 C2 106.4(6) . . ? C4 C3 H3 126.8 . . ? C2 C3 H3 126.8 . . ? N2 C4 C3 107.5(6) . . ? N2 C4 C5 123.4(6) . . ? C3 C4 C5 129.0(7) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N2 C6 C7 112.9(4) . . ? N2 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? N2 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? N3 C7 C8 113.6(5) . . ? N3 C7 C6 106.2(5) . . ? C8 C7 C6 107.4(5) . . ? N3 C7 C14 111.3(5) . . ? C8 C7 C14 112.0(5) . . ? C6 C7 C14 105.7(4) . . ? C9 C8 C13 113.9(6) . . ? C9 C8 C7 123.7(6) . . ? C13 C8 C7 122.3(6) . . ? C10 C9 C8 125.1(6) . . ? C10 C9 H9 117.4 . . ? C8 C9 H9 117.4 . . ? C11 C10 C9 118.8(7) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 120.6(7) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C13 117.9(7) . . ? C11 C12 H12 121.1 . . ? C13 C12 H12 121.1 . . ? C8 C13 C12 123.5(7) . . ? C8 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? C15 C14 C7 116.7(5) . . ? C15 C14 H14A 108.1 . . ? C7 C14 H14A 108.1 . . ? C15 C14 H14B 108.1 . . ? C7 C14 H14B 108.1 . . ? H14A C14 H14B 107.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 116.4(7) . . ? C17 C16 N3 124.4(6) . . ? C21 C16 N3 119.1(6) . . ? C18 C17 C16 122.0(7) . . ? C18 C17 H17 119.0 . . ? C16 C17 H17 119.0 . . ? C19 C18 C17 121.6(8) . . ? C19 C18 H18 119.2 . . ? C17 C18 H18 119.2 . . ? C18 C19 C20 118.6(7) . . ? C18 C19 H19 120.7 . . ? C20 C19 H19 120.7 . . ? C19 C20 C21 121.7(8) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C20 C21 C16 119.7(7) . . ? C20 C21 C22 117.6(7) . . ? C16 C21 C22 122.5(7) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 Al1 121.4(5) . . ? C24 C23 H23A 107.0 . . ? Al1 C23 H23A 107.0 . . ? C24 C23 H23B 107.0 . . ? Al1 C23 H23B 107.0 . . ? H23A C23 H23B 106.7 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 Al1 116.3(5) . . ? C26 C25 H25A 108.2 . . ? Al1 C25 H25A 108.2 . . ? C26 C25 H25B 108.2 . . ? Al1 C25 H25B 108.2 . . ? H25A C25 H25B 107.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Al1 N1 C2 -148.2(6) . . . . ? C23 Al1 N1 C2 -35.4(7) . . . . ? C25 Al1 N1 C2 92.1(6) . . . . ? N3 Al1 N1 N2 35.6(4) . . . . ? C23 Al1 N1 N2 148.5(4) . . . . ? C25 Al1 N1 N2 -84.1(4) . . . . ? C2 N1 N2 C4 3.3(6) . . . . ? Al1 N1 N2 C4 -179.4(4) . . . . ? C2 N1 N2 C6 179.2(5) . . . . ? Al1 N1 N2 C6 -3.5(6) . . . . ? N1 Al1 N3 C16 148.6(4) . . . . ? C23 Al1 N3 C16 35.5(5) . . . . ? C25 Al1 N3 C16 -105.8(5) . . . . ? N1 Al1 N3 C7 -16.3(5) . . . . ? C23 Al1 N3 C7 -129.3(4) . . . . ? C25 Al1 N3 C7 89.3(5) . . . . ? N2 N1 C2 C3 -2.6(7) . . . . ? Al1 N1 C2 C3 -179.2(5) . . . . ? N2 N1 C2 C1 -179.8(5) . . . . ? Al1 N1 C2 C1 3.7(10) . . . . ? N1 C2 C3 C4 1.0(8) . . . . ? C1 C2 C3 C4 178.0(6) . . . . ? N1 N2 C4 C3 -2.8(7) . . . . ? C6 N2 C4 C3 -178.0(6) . . . . ? N1 N2 C4 C5 179.3(5) . . . . ? C6 N2 C4 C5 4.1(10) . . . . ? C2 C3 C4 N2 1.0(8) . . . . ? C2 C3 C4 C5 178.8(6) . . . . ? C4 N2 C6 C7 117.4(7) . . . . ? N1 N2 C6 C7 -57.6(7) . . . . ? C16 N3 C7 C8 -77.2(6) . . . . ? Al1 N3 C7 C8 88.9(5) . . . . ? C16 N3 C7 C6 165.0(4) . . . . ? Al1 N3 C7 C6 -28.9(6) . . . . ? C16 N3 C7 C14 50.4(6) . . . . ? Al1 N3 C7 C14 -143.5(4) . . . . ? N2 C6 C7 N3 73.5(6) . . . . ? N2 C6 C7 C8 -48.4(7) . . . . ? N2 C6 C7 C14 -168.2(5) . . . . ? N3 C7 C8 C9 -17.1(8) . . . . ? C6 C7 C8 C9 100.1(6) . . . . ? C14 C7 C8 C9 -144.3(5) . . . . ? N3 C7 C8 C13 164.8(5) . . . . ? C6 C7 C8 C13 -78.0(7) . . . . ? C14 C7 C8 C13 37.7(8) . . . . ? C13 C8 C9 C10 -2.2(9) . . . . ? C7 C8 C9 C10 179.7(6) . . . . ? C8 C9 C10 C11 1.5(10) . . . . ? C9 C10 C11 C12 2.2(11) . . . . ? C10 C11 C12 C13 -4.7(11) . . . . ? C9 C8 C13 C12 -0.7(10) . . . . ? C7 C8 C13 C12 177.5(6) . . . . ? C11 C12 C13 C8 4.0(11) . . . . ? N3 C7 C14 C15 45.8(7) . . . . ? C8 C7 C14 C15 174.1(5) . . . . ? C6 C7 C14 C15 -69.2(6) . . . . ? C7 N3 C16 C17 33.3(7) . . . . ? Al1 N3 C16 C17 -132.8(5) . . . . ? C7 N3 C16 C21 -146.0(5) . . . . ? Al1 N3 C16 C21 47.9(7) . . . . ? C21 C16 C17 C18 1.5(8) . . . . ? N3 C16 C17 C18 -177.8(5) . . . . ? C16 C17 C18 C19 -2.4(10) . . . . ? C17 C18 C19 C20 1.8(11) . . . . ? C18 C19 C20 C21 -0.3(11) . . . . ? C19 C20 C21 C16 -0.5(10) . . . . ? C19 C20 C21 C22 174.2(7) . . . . ? C17 C16 C21 C20 0.0(9) . . . . ? N3 C16 C21 C20 179.3(5) . . . . ? C17 C16 C21 C22 -174.5(6) . . . . ? N3 C16 C21 C22 4.8(9) . . . . ? N3 Al1 C23 C24 -147.5(6) . . . . ? N1 Al1 C23 C24 108.6(6) . . . . ? C25 Al1 C23 C24 -7.1(7) . . . . ? N3 Al1 C25 C26 -152.4(5) . . . . ? N1 Al1 C25 C26 -49.6(6) . . . . ? C23 Al1 C25 C26 70.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.263 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.060