# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Barry, Sean' 'Wasslen, Yamile' 'Kurek, Agnieszka' 'Johnson, Paul' 'Pigeon, Taylor' 'Monillas, Wesley' 'Yap, Glenn' _publ_contact_author_name 'Barry, Sean' _publ_contact_author_email sbarry@connect.carleton.ca _publ_section_title ; Heteroleptic Iminopyrrolidinates of Aluminum ; # Attachment 'compound7cif.txt' data_seab012 _database_code_depnum_ccdc_archive 'CCDC 772427' #TrackingRef 'compound7cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H19 Al N2' _chemical_formula_weight 182.24 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 8.101(8) _cell_length_b 8.521(9) _cell_length_c 15.814(16) _cell_angle_alpha 90.00 _cell_angle_beta 93.618(15) _cell_angle_gamma 90.00 _cell_volume 1089.4(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 952 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.19 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.62 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.141 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9138 _exptl_absorpt_correction_T_max 0.9654 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 120(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 'Bruker AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 10212 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.17 _reflns_number_total 2492 _reflns_number_gt 2208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material 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^)+(0.1600P)^2^] 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 2492 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1853 _refine_ls_wR_factor_gt 0.1722 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Al Al 0.16186(5) 0.59183(5) 0.44671(3) 0.0232(2) Uani 1 1 d . . . N1 N 0.16713(14) 0.36702(16) 0.45898(8) 0.0242(3) Uani 1 1 d . . . N2 N -0.05665(14) 0.66392(13) 0.40932(7) 0.0236(3) Uani 1 1 d . . . C1 C 0.2278(2) 0.68878(18) 0.55673(11) 0.0336(4) Uani 1 1 d . . . H1A H 0.1326 0.6915 0.5920 0.050 Uiso 1 1 calc R . . H1B H 0.2666 0.7960 0.5476 0.050 Uiso 1 1 calc R . . H1C H 0.3169 0.6271 0.5853 0.050 Uiso 1 1 calc R . . C2 C 0.3311(2) 0.6388(2) 0.36493(12) 0.0385(4) Uani 1 1 d . . . H2A H 0.2966 0.5936 0.3096 0.058 Uiso 1 1 calc R . . H2B H 0.4373 0.5932 0.3854 0.058 Uiso 1 1 calc R . . H2C H 0.3429 0.7527 0.3594 0.058 Uiso 1 1 calc R . . C3 C 0.15636(17) 0.29035(16) 0.53164(9) 0.0244(3) Uani 1 1 d . . . C4 C 0.2651(3) 0.1458(2) 0.53589(12) 0.0443(5) Uani 1 1 d . . . H4A H 0.3640 0.1622 0.5749 0.053 Uiso 1 1 calc R . . H4B H 0.2035 0.0533 0.5550 0.053 Uiso 1 1 calc R . . C5 C 0.3119(3) 0.1256(2) 0.44749(13) 0.0514(6) Uani 1 1 d . . . H5A H 0.2597 0.0299 0.4224 0.062 Uiso 1 1 calc R . . H5B H 0.4335 0.1152 0.4461 0.062 Uiso 1 1 calc R . . C6 C 0.2532(2) 0.2673(2) 0.39907(10) 0.0381(4) Uani 1 1 d . . . H6A H 0.3480 0.3245 0.3771 0.046 Uiso 1 1 calc R . . H6B H 0.1766 0.2368 0.3506 0.046 Uiso 1 1 calc R . . C7 C -0.10336(19) 0.71595(19) 0.32106(9) 0.0309(4) Uani 1 1 d . . . H7A H -0.2250 0.7371 0.3172 0.037 Uiso 1 1 calc R . . C8 C -0.0714(3) 0.5836(2) 0.25968(11) 0.0409(5) Uani 1 1 d . . . H8A H -0.1291 0.4887 0.2767 0.061 Uiso 1 1 calc R . . H8B H 0.0476 0.5628 0.2604 0.061 Uiso 1 1 calc R . . H8C H -0.1122 0.6140 0.2023 0.061 Uiso 1 1 calc R . . C9 C -0.0162(2) 0.8675(2) 0.29700(11) 0.0382(4) Uani 1 1 d . . . H9A H -0.0416 0.9509 0.3368 0.057 Uiso 1 1 calc R . . H9B H -0.0549 0.8985 0.2394 0.057 Uiso 1 1 calc R . . H9C H 0.1035 0.8500 0.2993 0.057 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 Al 0.0232(3) 0.0215(3) 0.0251(3) 0.00100(14) 0.0031(2) 0.00002(13) N1 0.0267(7) 0.0231(6) 0.0230(6) -0.0013(5) 0.0031(5) 0.0017(4) N2 0.0267(6) 0.0231(6) 0.0210(6) 0.0018(4) 0.0010(5) 0.0007(4) C1 0.0348(8) 0.0289(8) 0.0361(9) -0.0023(6) -0.0063(7) -0.0047(6) C2 0.0355(9) 0.0324(8) 0.0493(11) 0.0086(7) 0.0176(8) 0.0032(7) C3 0.0250(7) 0.0219(7) 0.0260(7) 0.0000(5) 0.0001(5) 0.0006(5) C4 0.0592(12) 0.0335(9) 0.0415(10) 0.0087(7) 0.0137(8) 0.0225(8) C5 0.0682(14) 0.0444(10) 0.0432(11) 0.0042(9) 0.0167(10) 0.0272(10) C6 0.0533(11) 0.0299(8) 0.0326(9) -0.0035(6) 0.0140(8) 0.0094(7) C7 0.0333(8) 0.0351(8) 0.0241(8) 0.0064(6) -0.0001(6) -0.0004(6) C8 0.0529(11) 0.0463(11) 0.0229(8) -0.0015(7) -0.0022(8) -0.0041(7) C9 0.0434(9) 0.0376(9) 0.0342(9) 0.0129(7) 0.0059(7) 0.0008(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 Al N1 1.926(2) . ? Al N2 1.931(2) . ? Al C1 1.969(2) . ? Al C2 1.984(2) . ? N1 C3 1.329(2) . ? N1 C6 1.480(2) . ? N2 C3 1.331(2) 3_566 ? N2 C7 1.490(2) . ? C3 N2 1.331(2) 3_566 ? C3 C4 1.513(2) . ? C4 C5 1.482(3) . ? C5 C6 1.492(3) . ? C7 C8 1.521(3) . ? C7 C9 1.531(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Al N2 111.19(6) . . ? N1 Al C1 108.98(7) . . ? N2 Al C1 109.23(7) . . ? N1 Al C2 104.74(7) . . ? N2 Al C2 113.20(9) . . ? C1 Al C2 109.36(10) . . ? C3 N1 C6 109.30(14) . . ? C3 N1 Al 125.01(11) . . ? C6 N1 Al 121.00(11) . . ? C3 N2 C7 116.14(13) 3_566 . ? C3 N2 Al 117.61(11) 3_566 . ? C7 N2 Al 123.72(10) . . ? N1 C3 N2 122.57(14) . 3_566 ? N1 C3 C4 111.64(14) . . ? N2 C3 C4 125.76(14) 3_566 . ? C5 C4 C3 103.64(14) . . ? C4 C5 C6 107.32(15) . . ? N1 C6 C5 106.51(15) . . ? N2 C7 C8 109.50(14) . . ? N2 C7 C9 112.94(13) . . ? C8 C7 C9 111.54(16) . . ? 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 N2 Al N1 C3 -97.89(12) . . . . ? C1 Al N1 C3 22.57(13) . . . . ? C2 Al N1 C3 139.50(13) . . . . ? N2 Al N1 C6 109.02(13) . . . . ? C1 Al N1 C6 -130.52(13) . . . . ? C2 Al N1 C6 -13.59(14) . . . . ? N1 Al N2 C3 94.42(11) . . . 3_566 ? C1 Al N2 C3 -25.90(12) . . . 3_566 ? C2 Al N2 C3 -148.00(12) . . . 3_566 ? N1 Al N2 C7 -104.36(11) . . . . ? C1 Al N2 C7 135.33(12) . . . . ? C2 Al N2 C7 13.22(13) . . . . ? C6 N1 C3 N2 -165.74(13) . . . 3_566 ? Al N1 C3 N2 38.53(19) . . . 3_566 ? C6 N1 C3 C4 12.25(18) . . . . ? Al N1 C3 C4 -143.49(13) . . . . ? N1 C3 C4 C5 -13.0(2) . . . . ? N2 C3 C4 C5 164.86(17) 3_566 . . . ? C3 C4 C5 C6 8.3(2) . . . . ? C3 N1 C6 C5 -6.4(2) . . . . ? Al N1 C6 C5 150.48(14) . . . . ? C4 C5 C6 N1 -1.9(2) . . . . ? C3 N2 C7 C8 -140.51(14) 3_566 . . . ? Al N2 C7 C8 58.01(16) . . . . ? C3 N2 C7 C9 94.54(18) 3_566 . . . ? Al N2 C7 C9 -66.94(16) . . . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.478 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.067 # Attachment 'compound12cif.txt' data_seab035a _database_code_depnum_ccdc_archive 'CCDC 772428' #TrackingRef 'compound12cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H42 Al2 N4' _chemical_formula_weight 392.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.168(4) _cell_length_b 17.903(8) _cell_length_c 16.396(7) _cell_angle_alpha 90.00 _cell_angle_beta 104.42(2) _cell_angle_gamma 90.00 _cell_volume 2322.1(18) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 997 _cell_measurement_theta_min 2.57 _cell_measurement_theta_max 24.01 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.123 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9459 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 120(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 'Bruker AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 15891 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4100 _reflns_number_gt 3292 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0564P)^2^+0.7341P] 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 4100 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.09322(7) 0.22844(3) 0.57849(4) 0.01926(17) Uani 1 1 d . . . Al2 Al 0.47746(7) 0.33336(3) 0.61386(4) 0.02119(17) Uani 1 1 d . . . N1 N 0.16405(19) 0.27784(9) 0.68573(10) 0.0188(4) Uani 1 1 d . . . N2 N 0.29385(19) 0.38328(9) 0.64718(10) 0.0195(4) Uani 1 1 d . . . N3 N 0.49328(19) 0.23800(9) 0.67157(10) 0.0199(4) Uani 1 1 d . . . N4 N 0.29077(19) 0.17002(9) 0.57508(10) 0.0181(4) Uani 1 1 d . . . C1 C -0.0930(2) 0.16211(12) 0.59189(14) 0.0264(5) Uani 1 1 d . . . H1A H -0.0472 0.1228 0.6328 0.040 Uiso 1 1 calc R . . H1B H -0.1472 0.1394 0.5375 0.040 Uiso 1 1 calc R . . H1C H -0.1765 0.1914 0.6120 0.040 Uiso 1 1 calc R . . C2 C 0.0067(3) 0.30180(12) 0.48857(13) 0.0262(5) Uani 1 1 d . . . H2A H 0.1009 0.3313 0.4787 0.039 Uiso 1 1 calc R . . H2B H -0.0743 0.3350 0.5056 0.039 Uiso 1 1 calc R . . H2C H -0.0496 0.2756 0.4367 0.039 Uiso 1 1 calc R . . C3 C 0.2193(2) 0.34723(11) 0.70020(12) 0.0190(4) Uani 1 1 d . . . C4 C 0.2040(3) 0.37424(12) 0.78578(12) 0.0258(5) Uani 1 1 d . . . H4A H 0.1361 0.4206 0.7804 0.031 Uiso 1 1 calc R . . H4B H 0.3168 0.3837 0.8237 0.031 Uiso 1 1 calc R . . C5 C 0.1156(3) 0.31046(12) 0.81839(13) 0.0283(5) Uani 1 1 d . . . H5A H -0.0051 0.3222 0.8128 0.034 Uiso 1 1 calc R . . H5B H 0.1702 0.2999 0.8783 0.034 Uiso 1 1 calc R . . C6 C 0.1347(3) 0.24464(12) 0.76295(12) 0.0252(5) Uani 1 1 d . . . H6A H 0.2315 0.2129 0.7913 0.030 Uiso 1 1 calc R . . H6B H 0.0309 0.2138 0.7498 0.030 Uiso 1 1 calc R . . C7 C 0.2750(3) 0.46683(11) 0.63813(13) 0.0244(5) Uani 1 1 d . . . C8 C 0.3291(3) 0.48833(12) 0.55880(14) 0.0309(5) Uani 1 1 d . . . H8A H 0.2630 0.4597 0.5109 0.046 Uiso 1 1 calc R . . H8B H 0.4495 0.4773 0.5666 0.046 Uiso 1 1 calc R . . H8C H 0.3095 0.5418 0.5479 0.046 Uiso 1 1 calc R . . C9 C 0.0887(3) 0.48877(12) 0.62328(14) 0.0289(5) Uani 1 1 d . . . H9A H 0.0216 0.4616 0.5744 0.043 Uiso 1 1 calc R . . H9B H 0.0765 0.5426 0.6128 0.043 Uiso 1 1 calc R . . H9C H 0.0486 0.4762 0.6732 0.043 Uiso 1 1 calc R . . C10 C 0.3855(3) 0.50985(12) 0.71304(15) 0.0327(5) Uani 1 1 d . . . H10A H 0.5033 0.4936 0.7223 0.049 Uiso 1 1 calc R . . H10B H 0.3458 0.4998 0.7637 0.049 Uiso 1 1 calc R . . H10C H 0.3777 0.5635 0.7009 0.049 Uiso 1 1 calc R . . C11 C 0.6946(3) 0.38291(12) 0.66872(14) 0.0308(5) Uani 1 1 d . . . H11A H 0.6996 0.3917 0.7283 0.046 Uiso 1 1 calc R . . H11B H 0.7025 0.4307 0.6408 0.046 Uiso 1 1 calc R . . H11C H 0.7890 0.3507 0.6641 0.046 Uiso 1 1 calc R . . C12 C 0.4590(3) 0.31597(12) 0.49350(13) 0.0291(5) Uani 1 1 d . . . H12A H 0.3570 0.2867 0.4694 0.044 Uiso 1 1 calc R . . H12B H 0.5586 0.2885 0.4868 0.044 Uiso 1 1 calc R . . H12C H 0.4523 0.3640 0.4642 0.044 Uiso 1 1 calc R . . C13 C 0.4271(2) 0.17366(11) 0.64092(12) 0.0193(4) Uani 1 1 d . . . C14 C 0.5108(3) 0.10833(12) 0.69490(13) 0.0269(5) Uani 1 1 d . . . H14A H 0.4296 0.0826 0.7211 0.032 Uiso 1 1 calc R . . H14B H 0.5567 0.0719 0.6609 0.032 Uiso 1 1 calc R . . C15 C 0.6518(3) 0.14437(12) 0.76129(14) 0.0316(5) Uani 1 1 d . . . H15A H 0.6545 0.1245 0.8180 0.038 Uiso 1 1 calc R . . H15B H 0.7630 0.1354 0.7491 0.038 Uiso 1 1 calc R . . C16 C 0.6091(3) 0.22666(12) 0.75577(13) 0.0278(5) Uani 1 1 d . . . H16A H 0.5533 0.2410 0.8006 0.033 Uiso 1 1 calc R . . H16B H 0.7127 0.2571 0.7619 0.033 Uiso 1 1 calc R . . C17 C 0.2745(2) 0.10527(11) 0.51525(12) 0.0213(4) Uani 1 1 d . . . C18 C 0.2265(3) 0.03164(11) 0.55113(13) 0.0260(5) Uani 1 1 d . . . H18A H 0.3201 0.0150 0.5974 0.039 Uiso 1 1 calc R . . H18B H 0.2033 -0.0064 0.5068 0.039 Uiso 1 1 calc R . . H18C H 0.1254 0.0393 0.5721 0.039 Uiso 1 1 calc R . . C19 C 0.4375(3) 0.09767(12) 0.48632(14) 0.0281(5) Uani 1 1 d . . . H19A H 0.4649 0.1457 0.4643 0.042 Uiso 1 1 calc R . . H19B H 0.4224 0.0597 0.4420 0.042 Uiso 1 1 calc R . . H19C H 0.5299 0.0827 0.5341 0.042 Uiso 1 1 calc R . . C20 C 0.1346(3) 0.12481(13) 0.43746(13) 0.0292(5) Uani 1 1 d . . . H20A H 0.1606 0.1726 0.4144 0.044 Uiso 1 1 calc R . . H20B H 0.0266 0.1288 0.4531 0.044 Uiso 1 1 calc R . . H20C H 0.1266 0.0856 0.3950 0.044 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 0.0187(3) 0.0190(3) 0.0203(3) -0.0011(3) 0.0051(2) -0.0007(2) Al2 0.0204(3) 0.0198(3) 0.0250(3) -0.0020(3) 0.0087(3) -0.0021(2) N1 0.0194(8) 0.0199(9) 0.0179(8) -0.0001(7) 0.0061(6) -0.0006(7) N2 0.0204(8) 0.0165(9) 0.0226(9) -0.0009(7) 0.0071(7) -0.0020(7) N3 0.0192(8) 0.0199(9) 0.0205(9) -0.0013(7) 0.0049(7) -0.0007(7) N4 0.0196(8) 0.0179(9) 0.0176(8) -0.0014(7) 0.0062(6) -0.0001(7) C1 0.0214(10) 0.0262(12) 0.0324(12) -0.0049(10) 0.0080(9) -0.0009(9) C2 0.0282(11) 0.0256(12) 0.0235(11) -0.0008(9) 0.0040(9) 0.0018(9) C3 0.0152(9) 0.0217(11) 0.0192(10) -0.0007(9) 0.0028(8) 0.0023(8) C4 0.0279(11) 0.0287(12) 0.0213(11) -0.0036(9) 0.0068(9) -0.0008(9) C5 0.0319(12) 0.0340(13) 0.0212(11) 0.0001(10) 0.0107(9) 0.0006(10) C6 0.0283(11) 0.0266(12) 0.0223(11) 0.0032(9) 0.0091(9) -0.0027(9) C7 0.0291(11) 0.0155(11) 0.0303(12) -0.0017(9) 0.0106(9) 0.0001(8) C8 0.0330(12) 0.0233(12) 0.0379(13) 0.0068(10) 0.0118(10) 0.0006(9) C9 0.0306(11) 0.0229(11) 0.0333(12) -0.0007(10) 0.0084(9) 0.0036(9) C10 0.0324(12) 0.0245(12) 0.0415(14) -0.0070(11) 0.0097(10) -0.0042(9) C11 0.0241(11) 0.0269(12) 0.0416(13) -0.0009(11) 0.0084(9) -0.0027(9) C12 0.0323(12) 0.0269(12) 0.0321(12) -0.0001(10) 0.0158(10) -0.0028(9) C13 0.0185(9) 0.0217(11) 0.0201(10) 0.0000(9) 0.0096(8) 0.0006(8) C14 0.0289(11) 0.0237(12) 0.0265(11) 0.0023(9) 0.0040(9) 0.0026(9) C15 0.0307(12) 0.0330(13) 0.0280(12) 0.0064(10) 0.0014(9) 0.0007(10) C16 0.0239(10) 0.0327(13) 0.0239(11) -0.0029(10) 0.0009(9) -0.0028(9) C17 0.0261(10) 0.0173(10) 0.0215(10) -0.0030(8) 0.0079(8) -0.0001(8) C18 0.0278(11) 0.0215(11) 0.0297(12) -0.0042(9) 0.0091(9) -0.0030(9) C19 0.0333(12) 0.0249(12) 0.0301(12) -0.0024(10) 0.0153(10) 0.0006(9) C20 0.0349(12) 0.0288(12) 0.0219(11) -0.0055(10) 0.0034(9) 0.0020(10) _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 1.9242(18) . ? Al1 N4 1.9353(18) . ? Al1 C2 1.970(2) . ? Al1 C1 1.984(2) . ? Al2 N2 1.9376(18) . ? Al2 N3 1.9405(19) . ? Al2 C12 1.966(2) . ? Al2 C11 1.987(2) . ? N1 C3 1.323(3) . ? N1 C6 1.471(3) . ? N2 C3 1.344(2) . ? N2 C7 1.507(3) . ? N3 C13 1.318(3) . ? N3 C16 1.480(3) . ? N4 C13 1.345(2) . ? N4 C17 1.503(2) . ? C3 C4 1.518(3) . ? C4 C5 1.517(3) . ? C5 C6 1.520(3) . ? C7 C8 1.524(3) . ? C7 C9 1.531(3) . ? C7 C10 1.538(3) . ? C13 C14 1.522(3) . ? C14 C15 1.518(3) . ? C15 C16 1.512(3) . ? C17 C20 1.526(3) . ? C17 C19 1.527(3) . ? C17 C18 1.534(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Al1 N4 102.22(7) . . ? N1 Al1 C2 110.34(9) . . ? N4 Al1 C2 119.02(8) . . ? N1 Al1 C1 103.78(9) . . ? N4 Al1 C1 110.32(9) . . ? C2 Al1 C1 109.87(9) . . ? N2 Al2 N3 103.33(7) . . ? N2 Al2 C12 119.00(9) . . ? N3 Al2 C12 109.22(9) . . ? N2 Al2 C11 109.44(9) . . ? N3 Al2 C11 103.21(9) . . ? C12 Al2 C11 111.20(10) . . ? C3 N1 C6 110.27(16) . . ? C3 N1 Al1 127.38(13) . . ? C6 N1 Al1 121.62(13) . . ? C3 N2 C7 119.25(16) . . ? C3 N2 Al2 117.90(13) . . ? C7 N2 Al2 119.82(12) . . ? C13 N3 C16 109.99(16) . . ? C13 N3 Al2 127.73(14) . . ? C16 N3 Al2 121.66(13) . . ? C13 N4 C17 118.82(16) . . ? C13 N4 Al1 118.68(13) . . ? C17 N4 Al1 119.78(12) . . ? N1 C3 N2 121.61(17) . . ? N1 C3 C4 111.22(17) . . ? N2 C3 C4 126.84(18) . . ? C3 C4 C5 103.99(16) . . ? C4 C5 C6 104.13(16) . . ? N1 C6 C5 105.33(16) . . ? N2 C7 C8 106.90(16) . . ? N2 C7 C9 110.08(16) . . ? C8 C7 C9 106.70(18) . . ? N2 C7 C10 113.16(17) . . ? C8 C7 C10 108.56(17) . . ? C9 C7 C10 111.14(17) . . ? N3 C13 N4 121.82(17) . . ? N3 C13 C14 111.57(17) . . ? N4 C13 C14 126.26(17) . . ? C15 C14 C13 103.96(17) . . ? C16 C15 C14 104.41(17) . . ? N3 C16 C15 105.89(17) . . ? N4 C17 C20 107.15(16) . . ? N4 C17 C19 109.22(16) . . ? C20 C17 C19 106.87(17) . . ? N4 C17 C18 113.71(16) . . ? C20 C17 C18 107.93(17) . . ? C19 C17 C18 111.63(17) . . ? 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 N4 Al1 N1 C3 99.98(16) . . . . ? C2 Al1 N1 C3 -27.59(18) . . . . ? C1 Al1 N1 C3 -145.25(16) . . . . ? N4 Al1 N1 C6 -90.76(15) . . . . ? C2 Al1 N1 C6 141.67(15) . . . . ? C1 Al1 N1 C6 24.01(16) . . . . ? N3 Al2 N2 C3 1.04(15) . . . . ? C12 Al2 N2 C3 122.25(15) . . . . ? C11 Al2 N2 C3 -108.39(15) . . . . ? N3 Al2 N2 C7 161.21(13) . . . . ? C12 Al2 N2 C7 -77.58(16) . . . . ? C11 Al2 N2 C7 51.77(16) . . . . ? N2 Al2 N3 C13 97.22(17) . . . . ? C12 Al2 N3 C13 -30.39(19) . . . . ? C11 Al2 N3 C13 -148.76(17) . . . . ? N2 Al2 N3 C16 -92.69(15) . . . . ? C12 Al2 N3 C16 139.70(15) . . . . ? C11 Al2 N3 C16 21.32(17) . . . . ? N1 Al1 N4 C13 0.19(16) . . . . ? C2 Al1 N4 C13 121.99(15) . . . . ? C1 Al1 N4 C13 -109.69(15) . . . . ? N1 Al1 N4 C17 161.31(13) . . . . ? C2 Al1 N4 C17 -76.89(16) . . . . ? C1 Al1 N4 C17 51.43(16) . . . . ? C6 N1 C3 N2 163.51(17) . . . . ? Al1 N1 C3 N2 -26.2(3) . . . . ? C6 N1 C3 C4 -10.3(2) . . . . ? Al1 N1 C3 C4 159.97(13) . . . . ? C7 N2 C3 N1 148.92(18) . . . . ? Al2 N2 C3 N1 -50.8(2) . . . . ? C7 N2 C3 C4 -38.3(3) . . . . ? Al2 N2 C3 C4 121.97(18) . . . . ? N1 C3 C4 C5 -4.4(2) . . . . ? N2 C3 C4 C5 -177.80(18) . . . . ? C3 C4 C5 C6 16.3(2) . . . . ? C3 N1 C6 C5 20.8(2) . . . . ? Al1 N1 C6 C5 -150.13(13) . . . . ? C4 C5 C6 N1 -22.3(2) . . . . ? C3 N2 C7 C8 -164.85(17) . . . . ? Al2 N2 C7 C8 35.3(2) . . . . ? C3 N2 C7 C9 -49.3(2) . . . . ? Al2 N2 C7 C9 150.77(14) . . . . ? C3 N2 C7 C10 75.7(2) . . . . ? Al2 N2 C7 C10 -84.20(19) . . . . ? C16 N3 C13 N4 164.68(17) . . . . ? Al2 N3 C13 N4 -24.3(3) . . . . ? C16 N3 C13 C14 -8.9(2) . . . . ? Al2 N3 C13 C14 162.15(13) . . . . ? C17 N4 C13 N3 147.83(18) . . . . ? Al1 N4 C13 N3 -50.9(2) . . . . ? C17 N4 C13 C14 -39.6(3) . . . . ? Al1 N4 C13 C14 121.70(18) . . . . ? N3 C13 C14 C15 -4.4(2) . . . . ? N4 C13 C14 C15 -177.61(18) . . . . ? C13 C14 C15 C16 15.2(2) . . . . ? C13 N3 C16 C15 18.7(2) . . . . ? Al2 N3 C16 C15 -152.98(14) . . . . ? C14 C15 C16 N3 -20.4(2) . . . . ? C13 N4 C17 C20 -166.79(17) . . . . ? Al1 N4 C17 C20 32.1(2) . . . . ? C13 N4 C17 C19 -51.4(2) . . . . ? Al1 N4 C17 C19 147.54(14) . . . . ? C13 N4 C17 C18 74.0(2) . . . . ? Al1 N4 C17 C18 -87.05(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.279 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.050 # Attachment 'compound14cif.txt' data_seab040 _database_code_depnum_ccdc_archive 'CCDC 772429' #TrackingRef 'compound14cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H50 Al2 N4' _chemical_formula_weight 448.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.1090(14) _cell_length_b 19.526(4) _cell_length_c 8.7766(16) _cell_angle_alpha 90.00 _cell_angle_beta 101.582(3) _cell_angle_gamma 90.00 _cell_volume 1361.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 960 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.07 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9631 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 170(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 'Bruker AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 16418 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3371 _reflns_number_gt 2780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _computing_publication_material 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0621P)^2^+0.4659P] 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 3371 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1225 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 Al Al 0.04038(6) 0.06371(2) 0.14686(6) 0.02582(14) Uani 1 1 d . . . N1 N 0.01243(16) 0.10244(6) -0.06101(15) 0.0256(3) Uani 1 1 d . . . N2 N -0.17689(16) 0.01790(7) -0.17234(16) 0.0282(3) Uani 1 1 d . . . C1 C 0.1576(2) 0.12804(9) 0.3092(2) 0.0374(4) Uani 1 1 d . . . H1A H 0.2771 0.1321 0.3007 0.045 Uiso 1 1 calc R . . H1B H 0.1055 0.1740 0.2911 0.045 Uiso 1 1 calc R . . C2 C 0.1483(3) 0.10389(14) 0.4738(2) 0.0546(6) Uani 1 1 d . . . H2A H 0.2034 0.1376 0.5499 0.082 Uiso 1 1 calc R . . H2B H 0.2055 0.0596 0.4943 0.082 Uiso 1 1 calc R . . H2C H 0.0302 0.0990 0.4821 0.082 Uiso 1 1 calc R . . C3 C -0.1860(2) 0.04276(9) 0.1875(2) 0.0333(4) Uani 1 1 d . . . H3A H -0.2420 0.0090 0.1100 0.040 Uiso 1 1 calc R . . H3B H -0.1738 0.0218 0.2919 0.040 Uiso 1 1 calc R . . C4 C -0.2958(3) 0.10623(11) 0.1796(3) 0.0534(6) Uani 1 1 d . . . H4A H -0.4011 0.0945 0.2121 0.080 Uiso 1 1 calc R . . H4B H -0.3209 0.1236 0.0727 0.080 Uiso 1 1 calc R . . H4C H -0.2361 0.1415 0.2490 0.080 Uiso 1 1 calc R . . C5 C -0.3523(2) 0.01730(10) -0.2636(2) 0.0387(4) Uani 1 1 d . . . H5A H -0.4343 0.0225 -0.1946 0.046 Uiso 1 1 calc R . . H5B H -0.3764 -0.0259 -0.3231 0.046 Uiso 1 1 calc R . . C6 C -0.3596(3) 0.07847(11) -0.3726(3) 0.0489(5) Uani 1 1 d . . . H6A H -0.3272 0.0651 -0.4714 0.059 Uiso 1 1 calc R . . H6B H -0.4738 0.0987 -0.3959 0.059 Uiso 1 1 calc R . . C7 C -0.2333(2) 0.12790(9) -0.2816(2) 0.0372(4) Uani 1 1 d . . . H7A H -0.2899 0.1627 -0.2282 0.045 Uiso 1 1 calc R . . H7B H -0.1682 0.1513 -0.3504 0.045 Uiso 1 1 calc R . . C8 C -0.12041(19) 0.08205(8) -0.16495(18) 0.0265(3) Uani 1 1 d . . . C9 C 0.0257(2) 0.23105(9) -0.0333(2) 0.0415(4) Uani 1 1 d . . . H9A H -0.0974 0.2311 -0.0627 0.062 Uiso 1 1 calc R . . H9B H 0.0702 0.2720 -0.0754 0.062 Uiso 1 1 calc R . . H9C H 0.0600 0.2310 0.0803 0.062 Uiso 1 1 calc R . . C10 C 0.0952(2) 0.16685(8) -0.0993(2) 0.0325(4) Uani 1 1 d . . . H10A H 0.0692 0.1715 -0.2152 0.039 Uiso 1 1 calc R . . C11 C 0.2845(2) 0.15909(10) -0.0505(3) 0.0420(4) Uani 1 1 d . . . H11A H 0.3188 0.1156 -0.0931 0.050 Uiso 1 1 calc R . . H11B H 0.3149 0.1562 0.0643 0.050 Uiso 1 1 calc R . . C12 C 0.3818(3) 0.21776(10) -0.1050(3) 0.0476(5) Uani 1 1 d . . . H12A H 0.5028 0.2085 -0.0754 0.071 Uiso 1 1 calc R . . H12B H 0.3557 0.2605 -0.0563 0.071 Uiso 1 1 calc R . . H12C H 0.3496 0.2220 -0.2183 0.071 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 Al 0.0257(2) 0.0241(2) 0.0283(3) -0.00082(17) 0.00704(18) -0.00071(17) N1 0.0255(6) 0.0214(6) 0.0308(7) 0.0026(5) 0.0080(5) -0.0007(5) N2 0.0237(6) 0.0278(7) 0.0327(7) -0.0006(5) 0.0049(5) 0.0001(5) C1 0.0420(9) 0.0353(9) 0.0348(9) -0.0072(7) 0.0070(7) -0.0008(7) C2 0.0516(12) 0.0787(16) 0.0336(10) -0.0089(10) 0.0089(9) 0.0012(11) C3 0.0330(8) 0.0323(8) 0.0380(9) 0.0033(7) 0.0153(7) 0.0015(6) C4 0.0388(10) 0.0408(11) 0.0878(17) 0.0049(11) 0.0298(11) 0.0067(8) C5 0.0252(8) 0.0403(10) 0.0484(11) -0.0045(8) 0.0020(7) 0.0003(7) C6 0.0402(10) 0.0511(12) 0.0483(12) 0.0060(9) -0.0082(9) 0.0064(9) C7 0.0356(9) 0.0360(9) 0.0392(10) 0.0082(7) 0.0053(7) 0.0072(7) C8 0.0253(7) 0.0267(7) 0.0291(8) 0.0019(6) 0.0093(6) 0.0038(6) C9 0.0452(10) 0.0253(8) 0.0552(12) -0.0001(7) 0.0130(9) 0.0001(7) C10 0.0335(8) 0.0246(7) 0.0405(9) 0.0039(6) 0.0104(7) -0.0026(6) C11 0.0335(9) 0.0377(9) 0.0566(12) 0.0078(8) 0.0129(8) -0.0036(7) C12 0.0414(10) 0.0406(10) 0.0650(14) 0.0039(9) 0.0210(10) -0.0091(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 Al N2 1.9276(14) 3 ? Al N1 1.9457(14) . ? Al C3 1.9816(17) . ? Al C1 1.9920(18) . ? N1 C8 1.325(2) . ? N1 C10 1.4953(19) . ? N2 C8 1.331(2) . ? N2 C5 1.486(2) . ? N2 Al 1.9277(14) 3 ? C1 C2 1.535(3) . ? C3 C4 1.519(2) . ? C5 C6 1.524(3) . ? C6 C7 1.513(3) . ? C7 C8 1.520(2) . ? C9 C10 1.535(2) . ? C10 C11 1.516(2) . ? C11 C12 1.521(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Al N1 112.72(6) 3 . ? N2 Al C3 109.85(7) 3 . ? N1 Al C3 108.14(7) . . ? N2 Al C1 104.95(7) 3 . ? N1 Al C1 112.01(7) . . ? C3 Al C1 109.12(8) . . ? C8 N1 C10 115.95(13) . . ? C8 N1 Al 117.01(10) . . ? C10 N1 Al 124.38(11) . . ? C8 N2 C5 108.45(13) . . ? C8 N2 Al 126.05(11) . 3 ? C5 N2 Al 121.42(11) . 3 ? C2 C1 Al 111.89(14) . . ? C4 C3 Al 112.26(12) . . ? N2 C5 C6 104.16(14) . . ? C7 C6 C5 103.39(15) . . ? C6 C7 C8 103.43(14) . . ? N1 C8 N2 122.73(14) . . ? N1 C8 C7 125.66(14) . . ? N2 C8 C7 111.50(14) . . ? N1 C10 C11 109.11(13) . . ? N1 C10 C9 112.74(14) . . ? C11 C10 C9 113.74(16) . . ? C10 C11 C12 113.29(16) . . ? 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 N2 Al N1 C8 91.70(12) 3 . . . ? C3 Al N1 C8 -29.93(13) . . . . ? C1 Al N1 C8 -150.20(12) . . . . ? N2 Al N1 C10 -107.58(12) 3 . . . ? C3 Al N1 C10 130.79(12) . . . . ? C1 Al N1 C10 10.52(14) . . . . ? N2 Al C1 C2 -68.81(15) 3 . . . ? N1 Al C1 C2 168.56(13) . . . . ? C3 Al C1 C2 48.86(16) . . . . ? N2 Al C3 C4 176.22(14) 3 . . . ? N1 Al C3 C4 -60.40(16) . . . . ? C1 Al C3 C4 61.67(16) . . . . ? C8 N2 C5 C6 27.63(19) . . . . ? Al N2 C5 C6 -130.94(14) 3 . . . ? N2 C5 C6 C7 -29.70(19) . . . . ? C5 C6 C7 C8 21.54(19) . . . . ? C10 N1 C8 N2 159.76(14) . . . . ? Al N1 C8 N2 -37.89(19) . . . . ? C10 N1 C8 C7 -24.5(2) . . . . ? Al N1 C8 C7 137.83(14) . . . . ? C5 N2 C8 N1 162.28(15) . . . . ? Al N2 C8 N1 -40.4(2) 3 . . . ? C5 N2 C8 C7 -13.98(18) . . . . ? Al N2 C8 C7 143.33(12) 3 . . . ? C6 C7 C8 N1 178.46(16) . . . . ? C6 C7 C8 N2 -5.41(19) . . . . ? C8 N1 C10 C11 -140.77(15) . . . . ? Al N1 C10 C11 58.33(18) . . . . ? C8 N1 C10 C9 91.86(18) . . . . ? Al N1 C10 C9 -69.05(18) . . . . ? N1 C10 C11 C12 171.80(16) . . . . ? C9 C10 C11 C12 -61.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.399 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.055