Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Barron, A. R.' 'Bott, Simon G.' 'van Poppel, Laura H.' _publ_contact_author_name 'Prof A R Barron' _publ_contact_author_address ; Department of Chemistry Rice University MS-60 6100 Main Street Houston TX 77005 UNITED STATES OF AMERICA ; _publ_contact_author_email '?' _publ_section_title ; 1,4-Dioxobenzene Compounds of Aluminium ; data_sgb _database_code_CSD 187090 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H25 Al N O' _chemical_formula_weight 274.35 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? 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 8.621(2) _cell_length_b 12.516(3) _cell_length_c 16.124(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.90(3) _cell_angle_gamma 90.00 _cell_volume 1708.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.067 _exptl_crystal_density_method ? _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4377 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 23.42 _reflns_number_total 1990 _reflns_number_observed 1102 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0640P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1990 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_obs 0.0481 _refine_ls_wR_factor_all 0.1302 _refine_ls_wR_factor_obs 0.1166 _refine_ls_goodness_of_fit_all 0.910 _refine_ls_goodness_of_fit_obs 1.135 _refine_ls_restrained_S_all 0.910 _refine_ls_restrained_S_obs 1.135 _refine_ls_shift/esd_max -0.006 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Al Al -0.29338(11) -0.18671(9) 0.12791(7) 0.0540(4) Uani 1 d . . O1 O -0.2436(2) -0.0754(2) 0.0742(2) 0.0664(8) Uani 1 d . . N4 N -0.4903(3) -0.2310(2) 0.0477(2) 0.0561(9) Uani 1 d . . C1 C -0.1229(4) -0.0397(3) 0.0379(3) 0.0535(11) Uani 1 d . . C2 C 0.0091(4) 0.0073(3) 0.0853(2) 0.0625(12) Uani 1 d . . H2 H 0.0162(4) 0.0135(3) 0.1452(2) 0.075 Uiso 1 d R . C3 C -0.1294(4) -0.0461(3) -0.0480(3) 0.0628(12) Uani 1 d . . H3 H -0.2204(4) -0.0786(3) -0.0822(3) 0.075 Uiso 1 d R . C5 C -0.5627(4) -0.3231(3) 0.0577(3) 0.0827(14) Uani 1 d . . H5 H -0.5146(4) -0.3684(3) 0.1035(3) 0.099 Uiso 1 d R . C6 C -0.6982(5) -0.3566(4) 0.0056(4) 0.101(2) Uani 1 d . . H6 H -0.7462(5) -0.4233(4) 0.0158(4) 0.121 Uiso 1 d R . C7 C -0.7640(5) -0.2913(4) -0.0595(3) 0.089(2) Uani 1 d . . H7 H -0.8587(5) -0.3134(4) -0.0969(3) 0.107 Uiso 1 d R . C8 C -0.6941(4) -0.1969(4) -0.0705(3) 0.0776(13) Uani 1 d . . H8 H -0.7391(4) -0.1509(4) -0.1164(3) 0.093 Uiso 1 d R . C9 C -0.5578(4) -0.1699(3) -0.0165(2) 0.0620(11) Uani 1 d . . H9 H -0.5091(4) -0.1023(3) -0.0233(2) 0.074 Uiso 1 d R . C11 C -0.1418(4) -0.3072(3) 0.1314(3) 0.0710(13) Uani 1 d . . C12 C -0.1271(5) -0.3400(4) 0.0416(4) 0.108(2) Uani 1 d . . H12A H -0.0541(5) -0.3982(4) 0.0432(4) 0.163 Uiso 1 d R . H12B H -0.2294(5) -0.3617(4) 0.0119(4) 0.163 Uiso 1 d R . H12C H -0.0909(5) -0.2802(4) 0.0132(4) 0.163 Uiso 1 d R . C13 C 0.0221(5) -0.2704(4) 0.1774(4) 0.134(2) Uani 1 d . . H13A H 0.0970(5) -0.3276(4) 0.1796(4) 0.201 Uiso 1 d R . H13B H 0.0554(5) -0.2110(4) 0.1474(4) 0.201 Uiso 1 d R . H13C H 0.0157(5) -0.2488(4) 0.2337(4) 0.201 Uiso 1 d R . C14 C -0.1834(5) -0.4092(4) 0.1754(3) 0.104(2) Uani 1 d . . H14A H -0.1050(5) -0.4633(4) 0.1739(3) 0.157 Uiso 1 d R . H14B H -0.1858(5) -0.3912(4) 0.2330(3) 0.157 Uiso 1 d R . H14C H -0.2851(5) -0.4357(4) 0.1485(3) 0.157 Uiso 1 d R . C21 C -0.3701(4) -0.1394(3) 0.2302(3) 0.0658(12) Uani 1 d . . C22 C -0.4925(8) -0.0527(5) 0.2086(4) 0.180(3) Uani 1 d . . H22A H -0.5305(8) -0.0293(5) 0.2578(4) 0.271 Uiso 1 d R . H22B H -0.4472(8) 0.0067(5) 0.1840(4) 0.271 Uiso 1 d R . H22C H -0.5786(8) -0.0815(5) 0.1682(4) 0.271 Uiso 1 d R . C23 C -0.2366(7) -0.0930(6) 0.2938(4) 0.202(4) Uani 1 d . . H23A H -0.2733(7) -0.0700(6) 0.3435(4) 0.303 Uiso 1 d R . H23B H -0.1544(7) -0.1451(6) 0.3091(4) 0.303 Uiso 1 d R . H23C H -0.1961(7) -0.0327(6) 0.2679(4) 0.303 Uiso 1 d R . C24 C -0.4450(8) -0.2245(4) 0.2773(4) 0.175(3) Uani 1 d . . H24A H -0.4781(8) -0.1940(4) 0.3257(4) 0.262 Uiso 1 d R . H24B H -0.5349(8) -0.2540(4) 0.2400(4) 0.262 Uiso 1 d R . H24C H -0.3692(8) -0.2800(4) 0.2952(4) 0.262 Uiso 1 d 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 Al 0.0505(6) 0.0552(7) 0.0552(9) 0.0049(7) 0.0075(5) -0.0040(5) O1 0.0607(15) 0.065(2) 0.079(2) 0.019(2) 0.0252(13) -0.0115(13) N4 0.055(2) 0.051(2) 0.062(2) 0.006(2) 0.010(2) -0.005(2) C1 0.051(2) 0.053(2) 0.058(3) 0.010(2) 0.013(2) -0.010(2) C2 0.065(2) 0.081(3) 0.041(3) -0.003(2) 0.006(2) -0.016(2) C3 0.056(2) 0.073(3) 0.055(3) -0.002(2) 0.000(2) -0.020(2) C5 0.075(2) 0.065(3) 0.099(4) 0.019(3) -0.007(2) -0.014(2) C6 0.082(3) 0.080(3) 0.130(5) 0.006(3) -0.007(3) -0.029(3) C7 0.063(3) 0.109(4) 0.088(4) -0.020(3) -0.004(3) -0.010(3) C8 0.065(2) 0.094(4) 0.068(3) 0.004(3) -0.002(2) 0.001(3) C9 0.066(2) 0.063(3) 0.056(3) 0.009(2) 0.011(2) -0.001(2) C11 0.063(2) 0.068(3) 0.079(4) 0.012(3) 0.006(2) 0.004(2) C12 0.117(4) 0.091(4) 0.128(5) -0.003(4) 0.050(3) 0.025(3) C13 0.068(3) 0.115(4) 0.200(6) -0.013(4) -0.023(3) 0.022(3) C14 0.107(3) 0.085(3) 0.124(5) 0.033(3) 0.029(3) 0.030(3) C21 0.086(3) 0.068(3) 0.048(3) 0.003(2) 0.025(2) -0.006(2) C22 0.246(7) 0.183(6) 0.134(6) 0.027(5) 0.093(5) 0.136(6) C23 0.174(6) 0.325(10) 0.106(6) -0.111(6) 0.025(5) -0.087(6) C24 0.286(8) 0.112(5) 0.170(7) 0.000(5) 0.156(6) -0.034(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 Al O1 1.736(3) . ? Al C21 1.980(4) . ? Al C11 1.989(4) . ? Al N4 2.008(3) . ? O1 C1 1.362(4) . ? N4 C9 1.328(4) . ? N4 C5 1.336(4) . ? C1 C3 1.379(5) . ? C1 C2 1.377(4) . ? C2 C3 1.381(5) 3 ? C3 C2 1.381(5) 3 ? C5 C6 1.369(5) . ? C6 C7 1.366(6) . ? C7 C8 1.353(5) . ? C8 C9 1.367(5) . ? C11 C12 1.533(6) . ? C11 C13 1.536(5) . ? C11 C14 1.536(6) . ? C21 C22 1.507(6) . ? C21 C23 1.506(6) . ? C21 C24 1.521(6) . ? 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 Al C21 109.2(2) . . ? O1 Al C11 113.5(2) . . ? C21 Al C11 121.6(2) . . ? O1 Al N4 99.14(13) . . ? C21 Al N4 104.13(14) . . ? C11 Al N4 106.26(15) . . ? C1 O1 Al 139.4(2) . . ? C9 N4 C5 116.5(3) . . ? C9 N4 Al 122.4(2) . . ? C5 N4 Al 121.2(3) . . ? O1 C1 C3 121.6(3) . . ? O1 C1 C2 121.4(4) . . ? C3 C1 C2 117.0(3) . . ? C1 C2 C3 121.3(4) . 3 ? C1 C3 C2 121.7(3) . 3 ? N4 C5 C6 123.6(4) . . ? C7 C6 C5 118.1(4) . . ? C8 C7 C6 119.5(4) . . ? C7 C8 C9 118.9(4) . . ? N4 C9 C8 123.4(4) . . ? C12 C11 C13 107.6(4) . . ? C12 C11 C14 106.4(4) . . ? C13 C11 C14 107.5(4) . . ? C12 C11 Al 110.3(3) . . ? C13 C11 Al 109.0(3) . . ? C14 C11 Al 115.7(3) . . ? C22 C21 C23 106.9(5) . . ? C22 C21 C24 105.9(4) . . ? C23 C21 C24 105.8(5) . . ? C22 C21 Al 110.6(3) . . ? C23 C21 Al 110.5(3) . . ? C24 C21 Al 116.5(3) . . ? _refine_diff_density_max 0.169 _refine_diff_density_min -0.125 _refine_diff_density_rms 0.032 data_lvp _database_code_CSD 187091 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C24 H38.67 Al1.33 N1.33 O1.33' _chemical_formula_weight 403.20 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.983(2) _cell_length_b 13.960(3) _cell_length_c 12.837(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.85(3) _cell_angle_gamma 90.00 _cell_volume 1954.1(7) _cell_formula_units_Z 3 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.028 _exptl_crystal_density_method ? _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8798 _diffrn_reflns_av_R_equivalents 0.0870 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 23.36 _reflns_number_total 2829 _reflns_number_observed 1584 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1305P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2828 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1096 _refine_ls_R_factor_obs 0.0626 _refine_ls_wR_factor_all 0.2161 _refine_ls_wR_factor_obs 0.1812 _refine_ls_goodness_of_fit_all 0.963 _refine_ls_goodness_of_fit_obs 1.111 _refine_ls_restrained_S_all 0.971 _refine_ls_restrained_S_obs 1.111 _refine_ls_shift/esd_max -0.007 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Al1 Al 0.07418(10) 0.25128(8) 0.33202(9) 0.0664(5) Uani 1 d . . N1 N -0.0635(3) 0.1618(2) 0.2855(2) 0.0665(9) Uani 1 d . . O1 O -0.0156(2) 0.3448(2) 0.3668(2) 0.0776(8) Uani 1 d . . C1 C -0.0056(3) 0.4203(2) 0.4335(3) 0.0570(9) Uani 1 d . . C2 C 0.0731(3) 0.4956(3) 0.4216(3) 0.0702(10) Uani 1 d . . H2A H 0.1245(3) 0.4932(3) 0.3661(3) 0.084 Uiso 1 d R . C3 C -0.0779(3) 0.4267(2) 0.5118(3) 0.0667(10) Uani 1 d . . H3A H -0.1336(3) 0.3753(2) 0.5210(3) 0.080 Uiso 1 d R . C5 C -0.0425(4) 0.0802(3) 0.2347(3) 0.0829(13) Uani 1 d . . H5A H 0.0393(4) 0.0676(3) 0.2190(3) 0.099 Uiso 1 d R . C6 C -0.1324(4) 0.0146(3) 0.2053(3) 0.0906(14) Uani 1 d . . C7 C -0.2461(4) 0.0316(3) 0.2323(3) 0.0878(13) Uani 1 d . . H7A H -0.3096(4) -0.0148(3) 0.2140(3) 0.105 Uiso 1 d R . C8 C -0.2715(4) 0.1135(3) 0.2861(3) 0.0752(11) Uani 1 d . . C9 C -0.1759(4) 0.1769(3) 0.3093(3) 0.0697(11) Uani 1 d . . H9A H -0.1915(4) 0.2356(3) 0.3444(3) 0.084 Uiso 1 d R . C11 C 0.1597(5) 0.1865(4) 0.4556(5) 0.121(2) Uani 1 d . . C12 C 0.2501(7) 0.2575(4) 0.5165(6) 0.186(3) Uani 1 d . . H12A H 0.2930(7) 0.2279(4) 0.5777(6) 0.279 Uiso 1 d R . H12B H 0.3079(7) 0.2765(4) 0.4699(6) 0.279 Uiso 1 d R . H12C H 0.2068(7) 0.3128(4) 0.5369(6) 0.279 Uiso 1 d R . C13 C 0.0645(9) 0.1547(6) 0.5278(6) 0.216(4) Uani 1 d . . H13A H 0.1043(9) 0.1229(6) 0.5889(6) 0.324 Uiso 1 d R . H13B H 0.0229(9) 0.2107(6) 0.5488(6) 0.324 Uiso 1 d R . H13C H 0.0063(9) 0.1121(6) 0.4903(6) 0.324 Uiso 1 d R . C14 C 0.2374(8) 0.1000(5) 0.4283(6) 0.227(5) Uani 1 d . . H14A H 0.2764(8) 0.0709(5) 0.4914(6) 0.340 Uiso 1 d R . H14B H 0.1854(8) 0.0539(5) 0.3894(6) 0.340 Uiso 1 d R . H14C H 0.2988(8) 0.1217(5) 0.3864(6) 0.340 Uiso 1 d R . C15 C 0.1561(5) 0.2881(4) 0.2063(5) 0.110(2) Uani 1 d . . C16 C 0.0756(7) 0.3676(5) 0.1444(5) 0.162(3) Uani 1 d . . H16A H 0.1137(7) 0.3860(5) 0.0839(5) 0.244 Uiso 1 d R . H16B H -0.0052(7) 0.3434(5) 0.1224(5) 0.244 Uiso 1 d R . H16C H 0.0700(7) 0.4224(5) 0.1888(5) 0.244 Uiso 1 d R . C17 C 0.2756(5) 0.3395(5) 0.2447(6) 0.163(3) Uani 1 d . . H17A H 0.3175(5) 0.3583(5) 0.1865(6) 0.244 Uiso 1 d R . H17B H 0.2563(5) 0.3954(5) 0.2831(6) 0.244 Uiso 1 d R . H17C H 0.3274(5) 0.2978(5) 0.2900(6) 0.244 Uiso 1 d R . C18 C 0.1698(10) 0.2142(6) 0.1285(7) 0.274(7) Uani 1 d . . H18A H 0.2103(10) 0.2402(6) 0.0725(7) 0.410 Uiso 1 d R . H18B H 0.2162(10) 0.1610(6) 0.1596(7) 0.410 Uiso 1 d R . H18C H 0.0892(10) 0.1929(6) 0.1011(7) 0.410 Uiso 1 d R . C61 C -0.1032(5) -0.0753(4) 0.1461(5) 0.161(3) Uani 1 d . . H61A H -0.0188(5) -0.0745(4) 0.1334(5) 0.242 Uiso 1 d R . H61B H -0.1180(5) -0.1306(4) 0.1874(5) 0.242 Uiso 1 d R . H61C H -0.1550(5) -0.0779(4) 0.0804(5) 0.242 Uiso 1 d R . C81 C -0.3951(4) 0.1345(4) 0.3147(4) 0.120(2) Uani 1 d . . H81A H -0.3941(4) 0.1944(4) 0.3515(4) 0.179 Uiso 1 d R . H81B H -0.4525(4) 0.1380(4) 0.2523(4) 0.179 Uiso 1 d R . H81C H -0.4190(4) 0.0842(4) 0.3591(4) 0.179 Uiso 1 d 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 0.0608(8) 0.0583(7) 0.0786(8) -0.0255(6) 0.0027(5) -0.0029(5) N1 0.069(2) 0.053(2) 0.074(2) -0.0205(14) -0.004(2) 0.001(2) O1 0.079(2) 0.060(2) 0.093(2) -0.0367(13) 0.0055(14) 0.0000(13) C1 0.056(2) 0.046(2) 0.068(2) -0.013(2) 0.001(2) 0.005(2) C2 0.072(2) 0.066(2) 0.076(2) -0.021(2) 0.024(2) -0.010(2) C3 0.070(2) 0.050(2) 0.083(2) -0.013(2) 0.020(2) -0.015(2) C5 0.076(3) 0.063(2) 0.105(3) -0.033(2) -0.008(2) 0.003(2) C6 0.087(3) 0.062(3) 0.115(3) -0.033(2) -0.021(3) 0.003(2) C7 0.090(3) 0.064(3) 0.101(3) -0.013(2) -0.023(3) -0.014(2) C8 0.069(3) 0.070(3) 0.082(3) -0.006(2) -0.007(2) -0.012(2) C9 0.069(3) 0.061(2) 0.078(3) -0.016(2) 0.004(2) -0.002(2) C11 0.127(5) 0.084(3) 0.136(4) -0.028(3) -0.054(4) 0.023(3) C12 0.200(7) 0.149(5) 0.174(6) -0.050(5) -0.120(5) 0.029(5) C13 0.239(10) 0.251(10) 0.145(6) 0.104(6) -0.029(6) -0.022(8) C14 0.251(9) 0.128(5) 0.260(9) -0.072(5) -0.141(7) 0.108(6) C15 0.095(4) 0.111(4) 0.133(4) -0.045(4) 0.051(3) -0.021(3) C16 0.174(7) 0.190(7) 0.125(5) 0.016(5) 0.025(5) -0.017(6) C17 0.104(5) 0.177(6) 0.214(7) -0.013(5) 0.047(5) -0.037(4) C18 0.423(16) 0.186(7) 0.266(10) -0.121(7) 0.264(12) -0.115(9) C61 0.134(5) 0.101(4) 0.238(7) -0.106(4) -0.023(5) 0.007(4) C81 0.082(4) 0.129(4) 0.149(4) -0.036(3) 0.017(3) -0.027(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 O1 1.727(2) . ? Al1 C11 1.965(5) . ? Al1 N1 1.997(3) . ? Al1 C15 2.006(5) . ? N1 C9 1.323(4) . ? N1 C5 1.347(4) . ? O1 C1 1.354(4) . ? C1 C3 1.355(5) . ? C1 C2 1.382(5) . ? C2 C3 1.379(5) 3_566 ? C3 C2 1.379(5) 3_566 ? C5 C6 1.366(5) . ? C6 C7 1.357(6) . ? C6 C61 1.521(6) . ? C7 C8 1.382(5) . ? C8 C9 1.378(5) . ? C8 C81 1.477(6) . ? C11 C13 1.543(9) . ? C11 C14 1.543(8) . ? C11 C12 1.547(7) . ? C15 C18 1.456(7) . ? C15 C17 1.526(7) . ? C15 C16 1.574(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Al1 C11 111.8(2) . . ? O1 Al1 N1 96.58(13) . . ? C11 Al1 N1 103.1(2) . . ? O1 Al1 C15 109.8(2) . . ? C11 Al1 C15 123.4(3) . . ? N1 Al1 C15 108.4(2) . . ? C9 N1 C5 117.7(3) . . ? C9 N1 Al1 121.7(2) . . ? C5 N1 Al1 120.4(3) . . ? C1 O1 Al1 138.3(2) . . ? O1 C1 C3 120.6(3) . . ? O1 C1 C2 121.8(3) . . ? C3 C1 C2 117.5(3) . . ? C3 C2 C1 120.5(3) 3_566 . ? C1 C3 C2 122.0(3) . 3_566 ? N1 C5 C6 122.7(4) . . ? C7 C6 C5 118.0(4) . . ? C7 C6 C61 121.8(4) . . ? C5 C6 C61 120.2(5) . . ? C6 C7 C8 121.3(4) . . ? C9 C8 C7 116.4(4) . . ? C9 C8 C81 121.2(4) . . ? C7 C8 C81 122.3(4) . . ? N1 C9 C8 123.8(4) . . ? C13 C11 C14 110.1(6) . . ? C13 C11 C12 108.7(6) . . ? C14 C11 C12 106.1(5) . . ? C13 C11 Al1 108.9(4) . . ? C14 C11 Al1 113.6(4) . . ? C12 C11 Al1 109.2(4) . . ? C18 C15 C17 113.5(6) . . ? C18 C15 C16 104.6(7) . . ? C17 C15 C16 104.0(5) . . ? C18 C15 Al1 117.6(4) . . ? C17 C15 Al1 108.1(4) . . ? C16 C15 Al1 107.9(4) . . ? _refine_diff_density_max 0.409 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.045 data_arb _database_code_CSD 187092 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C0.65 H1.22 Al0.04 O0.09' _chemical_formula_weight 11.62 _chemical_melting_point ? _chemical_compound_source ? 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' '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 ? _symmetry_space_group_name_H-M ? 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 8.455(2) _cell_length_b 12.306(3) _cell_length_c 16.489(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.67(3) _cell_angle_gamma 90.00 _cell_volume 1659.7(6) _cell_formula_units_Z 92 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.070 _exptl_crystal_density_method ? _exptl_crystal_F_000 588 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4275 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0508 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 23.33 _reflns_number_total 2107 _reflns_number_observed 1444 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1176P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2107 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_obs 0.0604 _refine_ls_wR_factor_all 0.1848 _refine_ls_wR_factor_obs 0.1712 _refine_ls_goodness_of_fit_all 0.991 _refine_ls_goodness_of_fit_obs 1.125 _refine_ls_restrained_S_all 0.991 _refine_ls_restrained_S_obs 1.125 _refine_ls_shift/esd_max 0.004 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Al1 Al 0.07890(13) 0.19704(8) 0.38256(6) 0.0508(4) Uani 1 d . . O1 O 0.1978(3) 0.0943(2) 0.4368(2) 0.0662(8) Uani 1 d . . O2 O -0.0560(3) 0.2163(2) 0.4579(2) 0.0675(8) Uani 1 d . . C1 C 0.4145(4) 0.0422(3) 0.5527(2) 0.0574(10) Uani 1 d . . H1A H 0.3585(4) 0.0712(3) 0.5895(2) 0.069 Uiso 1 d R . C2 C 0.3471(4) 0.0499(2) 0.4674(2) 0.0489(9) Uani 1 d . . C3 C 0.4363(4) 0.0077(3) 0.4157(2) 0.0591(10) Uani 1 d . . H3A H 0.3951(4) 0.0130(3) 0.3579(2) 0.071 Uiso 1 d R . C4 C -0.0332(5) 0.1632(3) 0.5389(2) 0.0750(12) Uani 1 d . . H4A H 0.0804(5) 0.1667(3) 0.5703(2) 0.090 Uiso 1 calc R . H4B H -0.0662(5) 0.0876(3) 0.5319(2) 0.090 Uiso 1 calc R . C5 C -0.1391(7) 0.2244(4) 0.5831(3) 0.103(2) Uani 1 d . . H5A H -0.1930(7) 0.1749(4) 0.6132(3) 0.123 Uiso 1 calc R . H5B H -0.0744(7) 0.2756(4) 0.6227(3) 0.123 Uiso 1 calc R . C6 C -0.2563(8) 0.2802(6) 0.5195(4) 0.131(2) Uani 1 d . . H6A H -0.2805(8) 0.3506(6) 0.5401(4) 0.157 Uiso 1 calc R . H6B H -0.3569(8) 0.2387(6) 0.5037(4) 0.157 Uiso 1 calc R . C7 C -0.1896(7) 0.2938(5) 0.4488(4) 0.143(3) Uani 1 d . . H7A H -0.1494(7) 0.3674(5) 0.4471(4) 0.172 Uiso 1 calc R . H7B H -0.2726(7) 0.2800(5) 0.3973(4) 0.172 Uiso 1 calc R . C11 C -0.0636(5) 0.1434(3) 0.2758(2) 0.0700(11) Uani 1 d . . C12 C 0.0389(8) 0.1360(6) 0.2111(3) 0.141(2) Uani 1 d . . H12A H 0.0761(8) 0.2072(6) 0.2009(3) 0.212 Uiso 1 d R . H12B H -0.0269(8) 0.1064(6) 0.1597(3) 0.212 Uiso 1 d R . H12C H 0.1315(8) 0.0896(6) 0.2323(3) 0.212 Uiso 1 d R . C13 C -0.2072(8) 0.2144(5) 0.2337(4) 0.161(3) Uani 1 d . . H13A H -0.1693(8) 0.2866(5) 0.2271(4) 0.242 Uiso 1 d R . H13B H -0.2840(8) 0.2167(5) 0.2677(4) 0.242 Uiso 1 d R . H13C H -0.2593(8) 0.1848(5) 0.1797(4) 0.242 Uiso 1 d R . C14 C -0.1184(9) 0.0292(5) 0.2855(4) 0.170(3) Uani 1 d . . H14A H -0.0254(9) -0.0148(5) 0.3112(4) 0.255 Uiso 1 d R . H14B H -0.1708(9) 0.0000(5) 0.2314(4) 0.255 Uiso 1 d R . H14C H -0.1941(9) 0.0293(5) 0.3202(4) 0.255 Uiso 1 d R . C21 C 0.2003(5) 0.3355(3) 0.3851(3) 0.0717(12) Uani 1 d . . C22 C 0.0997(6) 0.4305(3) 0.3393(3) 0.109(2) Uani 1 d . . H22A H 0.0510(6) 0.4103(3) 0.2822(3) 0.163 Uiso 1 d R . H22B H 0.1696(6) 0.4922(3) 0.3405(3) 0.163 Uiso 1 d R . H22C H 0.0154(6) 0.4486(3) 0.3665(3) 0.163 Uiso 1 d R . C23 C 0.2751(6) 0.3683(4) 0.4761(3) 0.108(2) Uani 1 d . . H23A H 0.3399(6) 0.3094(4) 0.5052(3) 0.162 Uiso 1 d R . H23B H 0.1894(6) 0.3850(4) 0.5027(3) 0.162 Uiso 1 d R . H23C H 0.3430(6) 0.4311(4) 0.4775(3) 0.162 Uiso 1 d R . C24 C 0.3391(6) 0.3146(4) 0.3438(4) 0.116(2) Uani 1 d . . H24A H 0.2948(6) 0.2940(4) 0.2863(4) 0.173 Uiso 1 d R . H24B H 0.4071(6) 0.2571(4) 0.3729(4) 0.173 Uiso 1 d R . H24C H 0.4031(6) 0.3794(4) 0.3461(4) 0.173 Uiso 1 d 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 0.0445(8) 0.0582(6) 0.0482(7) 0.0098(4) 0.0088(6) 0.0083(5) O1 0.042(2) 0.078(2) 0.075(2) 0.0218(13) 0.0092(14) 0.0218(12) O2 0.059(2) 0.080(2) 0.069(2) 0.0208(13) 0.0264(15) 0.0251(13) C1 0.051(3) 0.073(2) 0.050(2) -0.001(2) 0.017(2) 0.018(2) C2 0.040(3) 0.051(2) 0.052(2) 0.0074(15) 0.007(2) 0.007(2) C3 0.057(3) 0.080(2) 0.038(2) 0.005(2) 0.008(2) 0.013(2) C4 0.088(4) 0.083(2) 0.063(3) 0.012(2) 0.035(3) 0.013(2) C5 0.099(4) 0.132(4) 0.089(4) -0.004(3) 0.045(3) 0.023(3) C6 0.114(5) 0.189(6) 0.099(4) -0.003(4) 0.043(4) 0.070(4) C7 0.116(5) 0.187(6) 0.150(5) 0.080(4) 0.079(4) 0.107(4) C11 0.063(3) 0.074(2) 0.063(3) 0.006(2) -0.001(2) 0.011(2) C12 0.154(5) 0.196(6) 0.071(3) -0.034(4) 0.023(4) 0.007(5) C13 0.133(6) 0.178(6) 0.121(5) -0.039(4) -0.063(5) 0.075(5) C14 0.221(8) 0.131(5) 0.112(5) 0.007(4) -0.043(5) -0.082(5) C21 0.067(3) 0.072(2) 0.073(3) 0.014(2) 0.012(2) -0.006(2) C22 0.112(4) 0.074(3) 0.130(4) 0.038(3) 0.013(3) -0.005(3) C23 0.110(4) 0.098(3) 0.100(4) -0.002(3) -0.005(3) -0.037(3) C24 0.091(4) 0.122(4) 0.146(5) 0.022(3) 0.052(4) -0.019(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 O1 1.719(2) . ? Al1 O2 1.903(2) . ? Al1 C11 1.978(4) . ? Al1 C21 1.985(4) . ? O1 C2 1.350(4) . ? O2 C4 1.455(4) . ? O2 C7 1.456(4) . ? C1 C2 1.380(5) . ? C1 C3 1.382(4) 3_656 ? C2 C3 1.376(4) . ? C3 C1 1.382(4) 3_656 ? C4 C5 1.492(5) . ? C5 C6 1.423(7) . ? C6 C7 1.428(7) . ? C11 C14 1.501(6) . ? C11 C13 1.513(6) . ? C11 C12 1.538(6) . ? C21 C24 1.521(6) . ? C21 C23 1.527(6) . ? C21 C22 1.527(5) . ? 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 96.89(11) . . ? O1 Al1 C11 111.21(15) . . ? O2 Al1 C11 107.0(2) . . ? O1 Al1 C21 112.9(2) . . ? O2 Al1 C21 105.8(2) . . ? C11 Al1 C21 120.0(2) . . ? C2 O1 Al1 149.4(2) . . ? C4 O2 C7 107.9(3) . . ? C4 O2 Al1 125.6(2) . . ? C7 O2 Al1 126.3(2) . . ? C2 C1 C3 121.1(3) . 3_656 ? O1 C2 C3 121.8(3) . . ? O1 C2 C1 121.0(3) . . ? C3 C2 C1 117.2(3) . . ? C2 C3 C1 121.7(3) . 3_656 ? O2 C4 C5 105.3(3) . . ? C6 C5 C4 106.1(4) . . ? C5 C6 C7 108.2(4) . . ? C6 C7 O2 107.2(4) . . ? C14 C11 C13 110.9(5) . . ? C14 C11 C12 105.2(5) . . ? C13 C11 C12 104.1(4) . . ? C14 C11 Al1 110.6(3) . . ? C13 C11 Al1 116.9(3) . . ? C12 C11 Al1 108.3(3) . . ? C24 C21 C23 108.1(4) . . ? C24 C21 C22 107.7(4) . . ? C23 C21 C22 108.9(4) . . ? C24 C21 Al1 107.4(3) . . ? C23 C21 Al1 109.3(3) . . ? C22 C21 Al1 115.2(3) . . ? _refine_diff_density_max 0.287 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.051