# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 # Attachment '- 8c.cif' data_t _database_code_depnum_ccdc_archive 'CCDC 806532' #TrackingRef '- 8c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H66 Al2 Br2 N2 O4, 2(C H2 Cl2)' _chemical_formula_sum 'C44 H70 Al2 Br2 Cl4 N2 O4' _chemical_formula_weight 1046.60 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.9848(17) _cell_length_b 17.0304(17) _cell_length_c 24.393(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5394.2(11) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6044 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 25.59 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 1.771 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.6559 _exptl_absorpt_correction_T_max 0.8428 _exptl_absorpt_process_details ? _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 18710 _diffrn_reflns_av_R_equivalents 0.0829 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6666 _reflns_number_gt 4745 _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^)+(0.0424P)^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 0.004(8) _refine_ls_number_reflns 6666 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.0997 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.934 _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 0.33010(6) 0.42079(4) 0.52058(3) 0.03330(17) Uani 1 1 d . . . Br1 Br 0.50171(2) 0.382479(18) 0.516664(14) 0.05756(11) Uani 1 1 d . . . C1 C 0.2754(2) 0.30081(16) 0.59208(12) 0.0389(6) Uani 1 1 d . . . C2 C 0.2593(2) 0.24649(16) 0.54905(12) 0.0419(7) Uani 1 1 d . . . C3 C 0.2472(2) 0.16551(17) 0.56148(13) 0.0446(7) Uani 1 1 d . . . H3 H 0.2359 0.1302 0.5330 0.054 Uiso 1 1 calc R . . C4 C 0.2517(2) 0.13834(16) 0.61359(14) 0.0474(8) Uani 1 1 d . . . C5 C 0.2706(2) 0.19317(18) 0.65466(12) 0.0490(8) Uani 1 1 d . . . H5 H 0.2752 0.1748 0.6905 0.059 Uiso 1 1 calc R . . C6 C 0.2831(2) 0.27290(17) 0.64621(11) 0.0421(7) Uani 1 1 d . . . C7 C 0.2472(2) 0.27051(15) 0.49284(11) 0.0400(6) Uani 1 1 d . . . H7 H 0.2284 0.2324 0.4675 0.048 Uiso 1 1 calc R . . C8 C 0.2429(2) 0.36195(15) 0.41698(12) 0.0386(6) Uani 1 1 d . . . H8 H 0.2679 0.3184 0.3943 0.046 Uiso 1 1 calc R . . C9 C 0.3136(2) 0.43389(17) 0.40692(11) 0.0418(7) Uani 1 1 d . . . H9A H 0.3821 0.4165 0.3965 0.050 Uiso 1 1 calc R . . H9B H 0.2861 0.4659 0.3775 0.050 Uiso 1 1 calc R . . C10 C 0.1281(2) 0.37600(19) 0.40282(11) 0.0471(7) Uani 1 1 d . . . C11 C 0.0633(3) 0.3037(2) 0.41520(17) 0.0740(11) Uani 1 1 d . . . H11A H 0.0572 0.2973 0.4542 0.111 Uiso 1 1 calc R . . H11B H 0.0958 0.2581 0.3997 0.111 Uiso 1 1 calc R . . H11C H -0.0040 0.3099 0.3995 0.111 Uiso 1 1 calc R . . C12 C 0.1208(3) 0.3921(2) 0.34089(12) 0.0678(10) Uani 1 1 d . . . H12A H 0.0498 0.3953 0.3303 0.102 Uiso 1 1 calc R . . H12B H 0.1536 0.3502 0.3212 0.102 Uiso 1 1 calc R . . H12C H 0.1547 0.4408 0.3326 0.102 Uiso 1 1 calc R . . C13 C 0.0835(3) 0.4452(2) 0.43434(15) 0.0641(10) Uani 1 1 d . . . H13A H 0.1184 0.4925 0.4237 0.096 Uiso 1 1 calc R . . H13B H 0.0927 0.4368 0.4729 0.096 Uiso 1 1 calc R . . H13C H 0.0114 0.4500 0.4263 0.096 Uiso 1 1 calc R . . C14 C 0.2334(3) 0.0510(2) 0.62833(16) 0.0627(9) Uani 1 1 d . . . C15 C 0.2379(4) -0.0021(2) 0.57772(19) 0.0922(15) Uani 1 1 d . . . H15A H 0.2994 0.0090 0.5573 0.138 Uiso 1 1 calc R . . H15B H 0.1788 0.0076 0.5551 0.138 Uiso 1 1 calc R . . H15C H 0.2382 -0.0560 0.5890 0.138 Uiso 1 1 calc R . . C16 C 0.1280(4) 0.0433(3) 0.6556(3) 0.126(2) Uani 1 1 d . . . H16A H 0.0750 0.0485 0.6284 0.188 Uiso 1 1 calc R . . H16B H 0.1201 0.0837 0.6827 0.188 Uiso 1 1 calc R . . H16C H 0.1226 -0.0072 0.6728 0.188 Uiso 1 1 calc R . . C17 C 0.3175(4) 0.0218(2) 0.66734(16) 0.0842(13) Uani 1 1 d . . . H17A H 0.3090 -0.0335 0.6735 0.126 Uiso 1 1 calc R . . H17B H 0.3123 0.0492 0.7016 0.126 Uiso 1 1 calc R . . H17C H 0.3839 0.0314 0.6514 0.126 Uiso 1 1 calc R . . C18 C 0.3032(3) 0.3312(2) 0.69408(13) 0.0608(10) Uani 1 1 d . . . C19 C 0.3132(4) 0.2878(2) 0.74936(14) 0.0860(13) Uani 1 1 d . . . H19A H 0.3742 0.2560 0.7491 0.129 Uiso 1 1 calc R . . H19B H 0.2540 0.2550 0.7549 0.129 Uiso 1 1 calc R . . H19C H 0.3177 0.3255 0.7785 0.129 Uiso 1 1 calc R . . C20 C 0.4047(3) 0.3758(2) 0.68460(15) 0.0731(11) Uani 1 1 d . . . H20A H 0.3999 0.4056 0.6513 0.110 Uiso 1 1 calc R . . H20B H 0.4604 0.3390 0.6818 0.110 Uiso 1 1 calc R . . H20C H 0.4170 0.4107 0.7148 0.110 Uiso 1 1 calc R . . C21 C 0.2106(4) 0.3860(3) 0.69902(15) 0.0787(12) Uani 1 1 d . . . H21A H 0.2255 0.4265 0.7253 0.118 Uiso 1 1 calc R . . H21B H 0.1516 0.3567 0.7109 0.118 Uiso 1 1 calc R . . H21C H 0.1966 0.4095 0.6640 0.118 Uiso 1 1 calc R . . C22 C 0.5033(4) 0.2395(3) 0.3884(2) 0.1190(19) Uani 1 1 d . . . H22A H 0.4945 0.2855 0.4113 0.143 Uiso 1 1 calc R . . H22B H 0.5767 0.2313 0.3835 0.143 Uiso 1 1 calc R . . Cl2 Cl 0.45103(17) 0.25776(15) 0.32719(8) 0.1825(10) Uani 1 1 d . . . Cl3 Cl 0.4531(2) 0.15978(13) 0.42200(12) 0.1982(10) Uani 1 1 d . . . N1 N 0.26057(17) 0.34147(13) 0.47511(9) 0.0365(5) Uani 1 1 d . . . O1 O 0.28260(16) 0.37732(11) 0.58136(7) 0.0410(4) Uani 1 1 d . . . O2 O 0.31833(15) 0.47807(10) 0.45612(7) 0.0364(4) 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 Al1 0.0370(4) 0.0255(3) 0.0373(4) 0.0027(3) -0.0004(4) -0.0007(3) Br1 0.04161(14) 0.04715(17) 0.0839(2) 0.00396(17) -0.00239(18) 0.00800(16) C1 0.0350(14) 0.0330(14) 0.0486(17) 0.0051(13) -0.0014(12) -0.0033(12) C2 0.0403(15) 0.0348(15) 0.0507(16) 0.0085(13) -0.0036(13) -0.0028(13) C3 0.0461(16) 0.0329(14) 0.0548(19) 0.0034(14) -0.0060(13) -0.0058(13) C4 0.0474(17) 0.0343(16) 0.060(2) 0.0151(14) -0.0059(14) -0.0089(14) C5 0.0507(17) 0.0523(19) 0.0441(17) 0.0186(15) -0.0044(14) -0.0033(16) C6 0.0476(16) 0.0389(16) 0.0399(16) 0.0092(13) -0.0004(12) -0.0039(14) C7 0.0415(14) 0.0333(14) 0.0450(16) -0.0007(12) -0.0051(12) -0.0037(13) C8 0.0514(17) 0.0310(14) 0.0333(14) -0.0023(11) 0.0014(12) -0.0002(13) C9 0.0532(17) 0.0372(15) 0.0350(15) -0.0003(12) 0.0026(13) 0.0013(14) C10 0.0524(17) 0.0458(17) 0.0432(16) 0.0002(14) -0.0103(13) -0.0030(16) C11 0.064(2) 0.068(3) 0.090(3) 0.009(2) -0.021(2) -0.024(2) C12 0.092(3) 0.061(2) 0.0496(19) -0.0071(17) -0.0252(18) 0.005(2) C13 0.0509(19) 0.073(3) 0.069(2) -0.0121(19) -0.0080(17) 0.0111(18) C14 0.067(2) 0.0431(18) 0.078(2) 0.0199(17) -0.0090(19) -0.0161(18) C15 0.137(4) 0.0400(18) 0.100(3) 0.015(2) -0.040(3) -0.019(3) C16 0.096(4) 0.061(3) 0.220(7) 0.031(4) 0.048(4) -0.016(3) C17 0.113(4) 0.053(2) 0.087(3) 0.023(2) -0.027(3) 0.000(2) C18 0.090(3) 0.0482(19) 0.0444(18) 0.0064(15) -0.0086(17) -0.0057(19) C19 0.140(4) 0.074(2) 0.0440(18) 0.015(2) -0.015(3) -0.014(3) C20 0.090(3) 0.067(3) 0.062(2) 0.007(2) -0.0224(19) -0.029(2) C21 0.112(3) 0.069(2) 0.054(2) -0.005(2) 0.010(2) 0.014(3) C22 0.071(3) 0.122(4) 0.164(5) -0.058(4) 0.010(3) -0.021(3) Cl2 0.1563(17) 0.259(3) 0.1317(13) -0.0588(16) -0.0307(12) 0.0701(18) Cl3 0.220(3) 0.1165(14) 0.258(3) -0.0097(17) 0.032(2) -0.0248(17) N1 0.0422(11) 0.0292(10) 0.0382(12) 0.0022(10) -0.0004(10) -0.0040(10) O1 0.0548(11) 0.0312(10) 0.0369(10) 0.0034(8) -0.0011(8) -0.0066(9) O2 0.0499(11) 0.0248(9) 0.0345(9) 0.0011(8) -0.0009(9) -0.0034(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al1 O1 1.768(2) . ? Al1 O2 1.8204(19) 4_566 ? Al1 O2 1.8568(19) . ? Al1 N1 1.967(2) . ? Al1 Br1 2.3239(8) . ? Al1 Al1 2.8788(14) 4_566 ? C1 O1 1.332(3) . ? C1 C6 1.407(4) . ? C1 C2 1.415(4) . ? C2 C3 1.421(4) . ? C2 C7 1.439(4) . ? C3 C4 1.354(5) . ? C3 H3 0.9300 . ? C4 C5 1.391(5) . ? C4 C14 1.549(4) . ? C5 C6 1.383(4) . ? C5 H5 0.9300 . ? C6 C18 1.555(5) . ? C7 N1 1.295(3) . ? C7 H7 0.9300 . ? C8 N1 1.478(4) . ? C8 C10 1.549(4) . ? C8 C9 1.551(4) . ? C8 H8 0.9800 . ? C9 O2 1.418(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.521(5) . ? C10 C11 1.522(5) . ? C10 C12 1.538(4) . ? 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 C16 1.528(6) . ? C14 C15 1.531(6) . ? C14 C17 1.531(5) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C21 1.527(6) . ? C18 C20 1.538(5) . ? C18 C19 1.543(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 Cl2 1.669(6) . ? C22 Cl3 1.715(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? O2 Al1 1.8203(19) 4_566 ? 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 O2 96.03(9) . 4_566 ? O1 Al1 O2 154.34(10) . . ? O2 Al1 O2 76.14(9) 4_566 . ? O1 Al1 N1 91.45(10) . . ? O2 Al1 N1 141.94(10) 4_566 . ? O2 Al1 N1 81.11(9) . . ? O1 Al1 Br1 104.56(7) . . ? O2 Al1 Br1 111.04(7) 4_566 . ? O2 Al1 Br1 101.04(7) . . ? N1 Al1 Br1 102.95(7) . . ? O1 Al1 Al1 133.22(8) . 4_566 ? O2 Al1 Al1 38.93(6) 4_566 4_566 ? O2 Al1 Al1 38.02(5) . 4_566 ? N1 Al1 Al1 116.54(8) . 4_566 ? Br1 Al1 Al1 104.40(2) . 4_566 ? O1 C1 C6 120.6(3) . . ? O1 C1 C2 120.3(2) . . ? C6 C1 C2 119.1(2) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 C7 122.5(2) . . ? C3 C2 C7 117.9(3) . . ? C4 C3 C2 121.8(3) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 117.0(3) . . ? C3 C4 C14 122.7(3) . . ? C5 C4 C14 120.3(3) . . ? C6 C5 C4 124.9(3) . . ? C6 C5 H5 117.5 . . ? C4 C5 H5 117.5 . . ? C5 C6 C1 117.6(3) . . ? C5 C6 C18 122.3(3) . . ? C1 C6 C18 120.1(3) . . ? N1 C7 C2 124.7(3) . . ? N1 C7 H7 117.7 . . ? C2 C7 H7 117.7 . . ? N1 C8 C10 113.6(2) . . ? N1 C8 C9 104.2(2) . . ? C10 C8 C9 114.4(2) . . ? N1 C8 H8 108.1 . . ? C10 C8 H8 108.1 . . ? C9 C8 H8 108.1 . . ? O2 C9 C8 108.1(2) . . ? O2 C9 H9A 110.1 . . ? C8 C9 H9A 110.1 . . ? O2 C9 H9B 110.1 . . ? C8 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? C13 C10 C11 108.5(3) . . ? C13 C10 C12 109.6(3) . . ? C11 C10 C12 107.8(3) . . ? C13 C10 C8 111.9(2) . . ? C11 C10 C8 111.3(3) . . ? C12 C10 C8 107.8(3) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C16 C14 C15 109.5(4) . . ? C16 C14 C17 109.9(4) . . ? C15 C14 C17 106.4(3) . . ? C16 C14 C4 108.7(3) . . ? C15 C14 C4 111.9(3) . . ? C17 C14 C4 110.3(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 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C21 C18 C20 112.6(3) . . ? C21 C18 C19 106.9(3) . . ? C20 C18 C19 107.2(3) . . ? C21 C18 C6 108.5(3) . . ? C20 C18 C6 110.3(3) . . ? C19 C18 C6 111.4(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? Cl2 C22 Cl3 114.9(3) . . ? Cl2 C22 H22A 108.5 . . ? Cl3 C22 H22A 108.5 . . ? Cl2 C22 H22B 108.5 . . ? Cl3 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? C7 N1 C8 121.3(2) . . ? C7 N1 Al1 120.92(19) . . ? C8 N1 Al1 116.76(16) . . ? C1 O1 Al1 126.76(18) . . ? C9 O2 Al1 140.37(16) . 4_566 ? C9 O2 Al1 116.20(15) . . ? Al1 O2 Al1 103.05(8) 4_566 . ? 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 O1 C1 C2 C3 -177.2(3) . . . . ? C6 C1 C2 C3 2.4(4) . . . . ? O1 C1 C2 C7 -1.7(4) . . . . ? C6 C1 C2 C7 177.9(3) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C7 C2 C3 C4 -176.4(3) . . . . ? C2 C3 C4 C5 -1.1(4) . . . . ? C2 C3 C4 C14 176.9(3) . . . . ? C3 C4 C5 C6 1.3(5) . . . . ? C14 C4 C5 C6 -176.8(3) . . . . ? C4 C5 C6 C1 0.5(5) . . . . ? C4 C5 C6 C18 179.5(3) . . . . ? O1 C1 C6 C5 177.3(3) . . . . ? C2 C1 C6 C5 -2.3(4) . . . . ? O1 C1 C6 C18 -1.7(4) . . . . ? C2 C1 C6 C18 178.7(3) . . . . ? C1 C2 C7 N1 7.7(4) . . . . ? C3 C2 C7 N1 -176.7(3) . . . . ? N1 C8 C9 O2 -33.3(3) . . . . ? C10 C8 C9 O2 91.3(3) . . . . ? N1 C8 C10 C13 62.6(3) . . . . ? C9 C8 C10 C13 -57.0(3) . . . . ? N1 C8 C10 C11 -59.0(3) . . . . ? C9 C8 C10 C11 -178.5(3) . . . . ? N1 C8 C10 C12 -176.9(2) . . . . ? C9 C8 C10 C12 63.6(3) . . . . ? C3 C4 C14 C16 -106.5(4) . . . . ? C5 C4 C14 C16 71.5(4) . . . . ? C3 C4 C14 C15 14.6(5) . . . . ? C5 C4 C14 C15 -167.4(3) . . . . ? C3 C4 C14 C17 132.9(4) . . . . ? C5 C4 C14 C17 -49.1(4) . . . . ? C5 C6 C18 C21 -114.1(3) . . . . ? C1 C6 C18 C21 64.9(4) . . . . ? C5 C6 C18 C20 122.2(3) . . . . ? C1 C6 C18 C20 -58.8(4) . . . . ? C5 C6 C18 C19 3.3(5) . . . . ? C1 C6 C18 C19 -177.7(3) . . . . ? C2 C7 N1 C8 -177.7(2) . . . . ? C2 C7 N1 Al1 14.2(4) . . . . ? C10 C8 N1 C7 81.3(3) . . . . ? C9 C8 N1 C7 -153.6(2) . . . . ? C10 C8 N1 Al1 -110.1(2) . . . . ? C9 C8 N1 Al1 15.0(2) . . . . ? O1 Al1 N1 C7 -31.6(2) . . . . ? O2 Al1 N1 C7 -133.3(2) 4_566 . . . ? O2 Al1 N1 C7 173.1(2) . . . . ? Br1 Al1 N1 C7 73.7(2) . . . . ? Al1 Al1 N1 C7 -172.71(19) 4_566 . . . ? O1 Al1 N1 C8 159.75(18) . . . . ? O2 Al1 N1 C8 58.1(2) 4_566 . . . ? O2 Al1 N1 C8 4.43(18) . . . . ? Br1 Al1 N1 C8 -94.95(17) . . . . ? Al1 Al1 N1 C8 18.6(2) 4_566 . . . ? C6 C1 O1 Al1 150.3(2) . . . . ? C2 C1 O1 Al1 -30.1(4) . . . . ? O2 Al1 O1 C1 -176.8(2) 4_566 . . . ? O2 Al1 O1 C1 112.9(3) . . . . ? N1 Al1 O1 C1 40.6(2) . . . . ? Br1 Al1 O1 C1 -63.2(2) . . . . ? Al1 Al1 O1 C1 170.15(18) 4_566 . . . ? C8 C9 O2 Al1 -147.0(2) . . . 4_566 ? C8 C9 O2 Al1 41.6(3) . . . . ? O1 Al1 O2 C9 -101.1(3) . . . . ? O2 Al1 O2 C9 -175.77(16) 4_566 . . . ? N1 Al1 O2 C9 -26.5(2) . . . . ? Br1 Al1 O2 C9 75.05(19) . . . . ? Al1 Al1 O2 C9 174.4(2) 4_566 . . . ? O1 Al1 O2 Al1 84.6(2) . . . 4_566 ? O2 Al1 O2 Al1 9.86(13) 4_566 . . 4_566 ? N1 Al1 O2 Al1 159.11(11) . . . 4_566 ? Br1 Al1 O2 Al1 -99.32(8) . . . 4_566 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C21 H21C O1 0.96 2.37 3.022(4) 124.9 . C20 H20A O1 0.96 2.34 2.976(4) 123.4 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.550 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.059