Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Huang, Yi-Lun' 'Huang, Bor-Hunn' 'Ko, Bao-Tsan' 'Lin, Chu-Chieh' _publ_contact_author_name 'Prof Chu-Chieh Lin' _publ_contact_author_address ; Prof Chu-Chieh Lin Department of Chemistry National Chung-Hsing University Taichung 402 TAIWAN ; data_1 _database_code_CSD 152733 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H20 Al N O' _chemical_formula_weight 233.28 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 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 22.798(3) _cell_length_b 11.0091(16) _cell_length_c 12.5820(18) _cell_angle_alpha 90.00 _cell_angle_beta 112.375(2) _cell_angle_gamma 90.00 _cell_volume 2920.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelapiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.60 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.061 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 8063 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 26.04 _reflns_number_total 2875 _reflns_number_gt 2109 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2875 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0750 _refine_ls_R_factor_gt 0.0582 _refine_ls_wR_factor_ref 0.2045 _refine_ls_wR_factor_gt 0.1904 _refine_ls_goodness_of_fit_ref 1.419 _refine_ls_restrained_S_all 1.419 _refine_ls_shift/su_max 0.087 _refine_ls_shift/su_mean 0.013 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 0.06120(3) 0.41807(6) 0.04589(6) 0.0541(3) Uani 1 1 d . . . O O 0.03373(8) 0.58331(13) 0.02356(16) 0.0657(5) Uani 1 1 d . . . N N 0.13408(10) 0.55549(17) 0.09964(19) 0.0610(5) Uani 1 1 d . . . C1 C 0.09079(11) 0.6364(2) 0.06635(19) 0.0535(6) Uani 1 1 d . . . C2 C 0.09191(11) 0.77050(19) 0.06760(19) 0.0534(6) Uani 1 1 d . . . C3 C 0.09947(16) 0.8347(2) -0.0200(2) 0.0787(8) Uani 1 1 d . . . H3A H 0.1052 0.7937 -0.0799 0.094 Uiso 1 1 calc R . . C4 C 0.09855(19) 0.9595(3) -0.0191(3) 0.0958(11) Uani 1 1 d . . . H4A H 0.1045 1.0023 -0.0780 0.115 Uiso 1 1 calc R . . C5 C 0.08916(15) 1.0211(2) 0.0658(3) 0.0844(9) Uani 1 1 d . . . H5A H 0.0886 1.1055 0.0652 0.101 Uiso 1 1 calc R . . C6 C 0.08061(16) 0.9597(3) 0.1515(3) 0.0839(9) Uani 1 1 d . . . H6A H 0.0736 1.0019 0.2096 0.101 Uiso 1 1 calc R . . C7 C 0.08223(14) 0.8344(2) 0.1533(2) 0.0717(7) Uani 1 1 d . . . H7A H 0.0767 0.7927 0.2131 0.086 Uiso 1 1 calc R . . C8 C 0.20334(13) 0.5717(2) 0.1567(3) 0.0791(8) Uani 1 1 d . . . C9 C 0.2304(2) 0.6607(5) 0.1019(5) 0.183(3) Uani 1 1 d . . . H9A H 0.2129 0.7394 0.1046 0.275 Uiso 1 1 calc R . . H9B H 0.2204 0.6379 0.0233 0.275 Uiso 1 1 calc R . . H9C H 0.2756 0.6632 0.1418 0.275 Uiso 1 1 calc R . . C10 C 0.2181(2) 0.6123(7) 0.2771(4) 0.186(3) Uani 1 1 d . . . H10A H 0.1998 0.6909 0.2765 0.278 Uiso 1 1 calc R . . H10B H 0.2632 0.6168 0.3174 0.278 Uiso 1 1 calc R . . H10C H 0.2008 0.5553 0.3151 0.278 Uiso 1 1 calc R . . C11 C 0.2313(2) 0.4492(5) 0.1597(7) 0.215(4) Uani 1 1 d . . . H11A H 0.2235 0.4230 0.0827 0.323 Uiso 1 1 calc R . . H11B H 0.2124 0.3927 0.1953 0.323 Uiso 1 1 calc R . . H11C H 0.2762 0.4526 0.2031 0.323 Uiso 1 1 calc R . . C12 C 0.07886(16) 0.3398(3) -0.0782(3) 0.0810(8) Uani 1 1 d . . . H12A H 0.0667 0.2559 -0.0831 0.121 Uiso 1 1 calc R . . H12B H 0.1234 0.3456 -0.0629 0.121 Uiso 1 1 calc R . . H12C H 0.0552 0.3796 -0.1497 0.121 Uiso 1 1 calc R . . C13 C 0.07491(14) 0.3397(2) 0.1922(2) 0.0748(8) Uani 1 1 d . . . H13A H 0.0627 0.2559 0.1792 0.112 Uiso 1 1 calc R . . H13B H 0.0498 0.3795 0.2282 0.112 Uiso 1 1 calc R . . H13C H 0.1190 0.3450 0.2413 0.112 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 0.0556(5) 0.0359(4) 0.0688(5) 0.0029(3) 0.0215(4) 0.0011(3) O 0.0498(9) 0.0363(9) 0.1003(13) -0.0017(7) 0.0165(9) -0.0070(6) N 0.0514(11) 0.0444(11) 0.0828(14) 0.0019(9) 0.0204(10) -0.0035(8) C1 0.0514(13) 0.0425(12) 0.0635(13) -0.0001(9) 0.0185(10) -0.0073(10) C2 0.0534(13) 0.0406(12) 0.0616(13) -0.0006(9) 0.0166(10) -0.0082(9) C3 0.117(2) 0.0554(15) 0.0741(17) 0.0006(12) 0.0478(17) -0.0109(15) C4 0.149(3) 0.0523(16) 0.088(2) 0.0146(15) 0.048(2) -0.0147(18) C5 0.105(2) 0.0395(14) 0.092(2) 0.0007(13) 0.0191(17) -0.0046(14) C6 0.112(3) 0.0544(16) 0.0808(18) -0.0144(14) 0.0321(17) 0.0022(15) C7 0.095(2) 0.0558(15) 0.0671(15) 0.0007(11) 0.0346(15) -0.0058(13) C8 0.0502(15) 0.0641(17) 0.112(2) 0.0051(14) 0.0191(15) -0.0074(12) C9 0.068(2) 0.229(6) 0.243(6) 0.084(5) 0.048(3) -0.023(3) C10 0.068(3) 0.319(9) 0.130(4) -0.039(4) -0.007(3) -0.005(3) C11 0.058(2) 0.106(3) 0.412(10) -0.016(5) 0.011(4) 0.015(2) C12 0.099(2) 0.0650(17) 0.0888(19) -0.0066(14) 0.0466(17) -0.0051(15) C13 0.0846(19) 0.0606(16) 0.0809(18) 0.0068(12) 0.0333(15) -0.0002(13) _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 O 1.9096(17) . ? Al C13 1.947(3) . ? Al C12 1.955(3) . ? Al O 2.0019(18) 5_565 ? Al N 2.157(2) . ? Al C1 2.484(2) . ? O C1 1.338(3) . ? O Al 2.0019(18) 5_565 ? N C1 1.276(3) . ? N C8 1.475(3) . ? C1 C2 1.476(3) . ? C2 C7 1.374(3) . ? C2 C3 1.375(3) . ? C3 C4 1.374(4) . ? C4 C5 1.349(4) . ? C5 C6 1.348(4) . ? C6 C7 1.380(4) . ? C8 C9 1.463(5) . ? C8 C10 1.490(6) . ? C8 C11 1.486(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 O Al C13 119.13(11) . . ? O Al C12 117.26(12) . . ? C13 Al C12 123.51(13) . . ? O Al O 72.75(7) . 5_565 ? C13 Al O 99.62(11) . 5_565 ? C12 Al O 99.50(11) . 5_565 ? O Al N 63.14(7) . . ? C13 Al N 100.79(11) . . ? C12 Al N 101.03(11) . . ? O Al N 135.89(7) 5_565 . ? O Al C1 32.23(8) . . ? C13 Al C1 113.04(10) . . ? C12 Al C1 112.27(11) . . ? O Al C1 104.98(7) 5_565 . ? N Al C1 30.91(7) . . ? C1 O Al 98.22(14) . . ? C1 O Al 154.52(15) . 5_565 ? Al O Al 107.25(7) . 5_565 ? C1 N C8 128.8(2) . . ? C1 N Al 88.83(14) . . ? C8 N Al 142.29(16) . . ? N C1 O 109.81(19) . . ? N C1 C2 133.4(2) . . ? O C1 C2 116.8(2) . . ? N C1 Al 60.26(12) . . ? O C1 Al 49.55(10) . . ? C2 C1 Al 166.36(17) . . ? C7 C2 C3 118.2(2) . . ? C7 C2 C1 120.9(2) . . ? C3 C2 C1 120.9(2) . . ? C4 C3 C2 120.1(2) . . ? C5 C4 C3 121.0(3) . . ? C6 C5 C4 119.8(3) . . ? C5 C6 C7 120.2(3) . . ? C2 C7 C6 120.7(2) . . ? C9 C8 N 114.6(3) . . ? C9 C8 C10 107.8(4) . . ? N C8 C10 108.4(3) . . ? C9 C8 C11 111.5(4) . . ? N C8 C11 105.8(3) . . ? C10 C8 C11 108.5(4) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.373 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.049 #===END data_2 _database_code_CSD 152734 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H29 Al2 N O' _chemical_formula_weight 305.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Al' 'Al' 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.5760(11) _cell_length_b 13.4314(9) _cell_length_c 21.0210(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4115.4(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelapiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.58 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.986 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 22012 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4052 _reflns_number_gt 2721 _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^)+(0.1500P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4052 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.2082 _refine_ls_wR_factor_gt 0.1820 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 5.534 _refine_ls_shift/su_mean 0.515 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 -0.02233(6) 0.56793(6) 0.30325(3) 0.0733(3) Uani 1 1 d . . . Al2 Al 0.17844(5) 0.57381(6) 0.39564(4) 0.0700(3) Uani 1 1 d . . . O O 0.06173(11) 0.62253(12) 0.36419(8) 0.0715(5) Uani 1 1 d . . . N N -0.07529(13) 0.67877(17) 0.35115(9) 0.0665(5) Uani 1 1 d . . . C1 C -0.0693(3) 0.4389(3) 0.3257(2) 0.1276(14) Uani 1 1 d . . . H1A H -0.0737 0.3984 0.2882 0.191 Uiso 1 1 calc R . . H1B H -0.1290 0.4461 0.3444 0.191 Uiso 1 1 calc R . . H1C H -0.0287 0.4078 0.3556 0.191 Uiso 1 1 calc R . . C2 C 0.0091(3) 0.6047(3) 0.21706(15) 0.1081(10) Uani 1 1 d . . . H2A H -0.0021 0.5493 0.1892 0.162 Uiso 1 1 calc R . . H2B H 0.0728 0.6227 0.2151 0.162 Uiso 1 1 calc R . . H2C H -0.0277 0.6603 0.2040 0.162 Uiso 1 1 calc R . . C3 C 0.2043(3) 0.4808(3) 0.32537(19) 0.1223(13) Uani 1 1 d . . . H3A H 0.1608 0.4271 0.3264 0.184 Uiso 1 1 calc R . . H3B H 0.2652 0.4546 0.3300 0.184 Uiso 1 1 calc R . . H3C H 0.1995 0.5153 0.2855 0.184 Uiso 1 1 calc R . . C4 C 0.1502(3) 0.5142(3) 0.47824(18) 0.1246(13) Uani 1 1 d . . . H4A H 0.1390 0.5660 0.5088 0.187 Uiso 1 1 calc R . . H4B H 0.2011 0.4744 0.4920 0.187 Uiso 1 1 calc R . . H4C H 0.0966 0.4731 0.4745 0.187 Uiso 1 1 calc R . . C5 C 0.2629(2) 0.6863(3) 0.39833(19) 0.1069(11) Uani 1 1 d . . . H5A H 0.2473 0.7288 0.4334 0.160 Uiso 1 1 calc R . . H5B H 0.2586 0.7232 0.3593 0.160 Uiso 1 1 calc R . . H5C H 0.3245 0.6623 0.4036 0.160 Uiso 1 1 calc R . . C6 C -0.00081(15) 0.69043(16) 0.38288(11) 0.0610(5) Uani 1 1 d . . . C7 C 0.02626(14) 0.76335(17) 0.43179(11) 0.0640(6) Uani 1 1 d . . . C8 C 0.0090(2) 0.7443(3) 0.49506(13) 0.0934(9) Uani 1 1 d . . . H8A H -0.0206 0.6858 0.5069 0.112 Uiso 1 1 calc R . . C9 C 0.0355(3) 0.8117(3) 0.54047(18) 0.1152(12) Uani 1 1 d . . . H9A H 0.0240 0.7986 0.5832 0.138 Uiso 1 1 calc R . . C10 C 0.0782(3) 0.8971(4) 0.5236(3) 0.1258(15) Uani 1 1 d . . . H10A H 0.0948 0.9430 0.5546 0.151 Uiso 1 1 calc R . . C11 C 0.0970(2) 0.9161(3) 0.4613(3) 0.1169(13) Uani 1 1 d . . . H11A H 0.1278 0.9741 0.4502 0.140 Uiso 1 1 calc R . . C12 C 0.0705(2) 0.8492(2) 0.41429(17) 0.0906(8) Uani 1 1 d . . . H12A H 0.0826 0.8625 0.3717 0.109 Uiso 1 1 calc R . . C13 C -0.16164(18) 0.7392(2) 0.35304(13) 0.0825(8) Uani 1 1 d . . . C14 C -0.1855(9) 0.7669(14) 0.4190(8) 0.128(6) Uani 0.50 1 d P . . H14A H -0.136(9) 0.751(10) 0.449(5) 0.192 Uiso 0.50 1 calc P . . H14B H -0.244(15) 0.784(13) 0.418(8) 0.192 Uiso 0.50 1 d P . . H14C H -0.201(14) 0.693(16) 0.441(11) 0.192 Uiso 0.50 1 d P . . C14' C -0.2146(13) 0.716(3) 0.4081(13) 0.226(15) Uani 0.50 1 d P . . H14D H -0.18(2) 0.66(2) 0.427(18) 0.338 Uiso 0.50 1 calc P . . H14E H -0.278(17) 0.75(3) 0.405(13) 0.338 Uiso 0.50 1 d P . . H14F H -0.099(16) 0.683(18) 0.339(10) 0.338 Uiso 0.50 1 d P . . C15 C -0.1449(11) 0.8212(18) 0.3132(12) 0.194(13) Uani 0.50 1 d P . . H15A H -0.083(16) 0.821(19) 0.296(13) 0.292 Uiso 0.50 1 calc P . . H15B H -0.130(15) 0.82(2) 0.253(12) 0.292 Uiso 0.50 1 d P . . H15C H -0.17(2) 0.89(3) 0.324(11) 0.292 Uiso 0.50 1 d P . . C15' C -0.1474(8) 0.8527(7) 0.3581(11) 0.153(7) Uani 0.50 1 d P . . H15D H -0.082(12) 0.854(10) 0.368(8) 0.229 Uiso 0.50 1 calc P . . H15E H -0.148(15) 0.801(15) 0.292(10) 0.229 Uiso 0.50 1 d P . . H15F H -0.212(16) 0.882(17) 0.347(8) 0.229 Uiso 0.50 1 d P . . C16 C -0.2342(6) 0.663(2) 0.3286(11) 0.172(8) Uani 0.50 1 d P . . H16A H -0.211(13) 0.596(16) 0.323(12) 0.258 Uiso 0.50 1 calc P . . H16B H -0.305(12) 0.692(13) 0.346(10) 0.258 Uiso 0.50 1 d P . . H16C H -0.224(19) 0.682(17) 0.399(12) 0.258 Uiso 0.50 1 d P . . C16' C -0.2072(11) 0.7238(13) 0.2881(8) 0.140(4) Uani 0.50 1 d P . . H16D H -0.160(12) 0.684(14) 0.266(7) 0.210 Uiso 0.50 1 calc P . . H16E H -0.207(12) 0.644(15) 0.272(8) 0.210 Uiso 0.50 1 d P . . H16F H -0.252(10) 0.755(11) 0.289(6) 0.210 Uiso 0.50 1 d P . . 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 0.0788(5) 0.0778(5) 0.0634(5) -0.0071(3) -0.0059(3) -0.0087(3) Al2 0.0658(5) 0.0736(5) 0.0707(5) 0.0000(3) -0.0034(3) 0.0108(3) O 0.0673(10) 0.0704(10) 0.0770(10) -0.0137(8) -0.0125(8) 0.0103(7) N 0.0549(11) 0.0798(13) 0.0647(11) 0.0011(9) -0.0044(8) -0.0025(8) C1 0.168(4) 0.089(2) 0.125(3) -0.002(2) 0.003(3) -0.035(2) C2 0.111(2) 0.137(3) 0.0765(18) -0.0015(18) 0.0063(16) 0.010(2) C3 0.139(3) 0.113(3) 0.115(3) -0.027(2) -0.012(2) 0.048(2) C4 0.110(3) 0.147(3) 0.117(3) 0.054(2) 0.010(2) 0.017(2) C5 0.0728(19) 0.111(3) 0.137(3) 0.0034(19) 0.0009(17) -0.0037(16) C6 0.0580(12) 0.0620(12) 0.0630(12) 0.0041(9) -0.0018(10) -0.0005(9) C7 0.0510(12) 0.0677(14) 0.0734(14) -0.0068(10) -0.0037(10) 0.0035(9) C8 0.108(2) 0.099(2) 0.0731(17) -0.0103(14) -0.0030(14) -0.0027(16) C9 0.131(3) 0.126(3) 0.089(2) -0.037(2) -0.016(2) 0.011(3) C10 0.101(3) 0.123(3) 0.154(4) -0.073(3) -0.038(3) 0.028(2) C11 0.084(2) 0.080(2) 0.187(4) -0.033(2) -0.005(2) -0.0094(16) C12 0.0836(19) 0.0718(16) 0.116(2) -0.0084(15) 0.0096(16) -0.0063(13) C13 0.0531(13) 0.111(2) 0.0835(17) 0.0052(15) -0.0052(11) 0.0086(13) C14 0.080(7) 0.184(14) 0.119(7) -0.038(10) 0.000(6) 0.056(8) C14' 0.092(10) 0.37(3) 0.22(2) 0.18(2) 0.070(12) 0.078(15) C15 0.131(10) 0.23(2) 0.218(19) 0.16(2) 0.055(13) 0.114(15) C15' 0.077(6) 0.081(5) 0.30(2) -0.026(9) -0.034(9) 0.020(4) C16 0.051(4) 0.27(2) 0.198(15) -0.104(15) -0.015(6) -0.009(7) C16' 0.095(7) 0.175(12) 0.151(9) -0.033(9) -0.058(7) 0.039(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 O 1.9184(17) . ? Al1 C1 1.922(4) . ? Al1 C2 1.933(3) . ? Al1 N 1.956(2) . ? Al1 C6 2.368(2) . ? Al2 O 1.9389(17) . ? Al2 C4 1.956(3) . ? Al2 C5 1.950(3) . ? Al2 C3 1.971(3) . ? O C6 1.348(3) . ? N C6 1.284(3) . ? N C13 1.498(3) . ? C6 C7 1.474(3) . ? C7 C8 1.378(4) . ? C7 C12 1.372(4) . ? C8 C9 1.371(5) . ? C9 C10 1.352(6) . ? C10 C11 1.361(6) . ? C11 C12 1.391(5) . ? C13 C15 1.405(12) . ? C13 C14' 1.427(15) . ? C13 C14 1.477(14) . ? C13 C16' 1.533(11) . ? C13 C15' 1.542(10) . ? C13 C16 1.555(14) . ? C14 C14' 0.84(4) . ? C14 C15' 1.81(3) . ? C14' C16 1.83(4) . ? C15 C15' 1.03(3) . ? C15 C16' 1.68(3) . ? C16 C16' 1.24(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 O Al1 C1 114.10(17) . . ? O Al1 C2 112.13(14) . . ? C1 Al1 C2 123.0(2) . . ? O Al1 N 67.50(8) . . ? C1 Al1 N 114.78(16) . . ? C2 Al1 N 112.44(14) . . ? O Al1 C6 34.69(7) . . ? C1 Al1 C6 120.01(16) . . ? C2 Al1 C6 116.98(14) . . ? N Al1 C6 32.81(8) . . ? O Al2 C4 104.84(14) . . ? O Al2 C5 107.60(12) . . ? C4 Al2 C5 115.10(19) . . ? O Al2 C3 97.25(13) . . ? C4 Al2 C3 116.5(2) . . ? C5 Al2 C3 113.09(19) . . ? C6 O Al1 91.22(13) . . ? C6 O Al2 136.24(14) . . ? Al1 O Al2 131.23(9) . . ? C6 N C13 129.1(2) . . ? C6 N Al1 91.52(15) . . ? C13 N Al1 139.25(17) . . ? N C6 O 109.8(2) . . ? N C6 C7 132.1(2) . . ? O C6 C7 118.16(19) . . ? N C6 Al1 55.67(13) . . ? O C6 Al1 54.09(10) . . ? C7 C6 Al1 172.04(16) . . ? C8 C7 C12 120.1(3) . . ? C8 C7 C6 120.1(2) . . ? C12 C7 C6 119.8(2) . . ? C7 C8 C9 119.9(3) . . ? C10 C9 C8 120.5(4) . . ? C9 C10 C11 120.3(3) . . ? C10 C11 C12 120.4(4) . . ? C7 C12 C11 118.9(4) . . ? C15 C13 C14' 138.7(17) . . ? C15 C13 C14 113.8(15) . . ? C14' C13 C14 33.6(16) . . ? C15 C13 N 105.3(5) . . ? C14' C13 N 110.9(9) . . ? C14 C13 N 111.0(6) . . ? C15 C13 C16' 69.5(14) . . ? C14' C13 C16' 117.3(16) . . ? C14 C13 C16' 140.2(8) . . ? N C13 C16' 105.5(6) . . ? C15 C13 C15' 40.8(11) . . ? C14' C13 C15' 103.7(19) . . ? C14 C13 C15' 73.6(12) . . ? N C13 C15' 115.1(5) . . ? C16' C13 C15' 104.6(9) . . ? C15 C13 C16 115.7(17) . . ? C14' C13 C16 76(2) . . ? C14 C13 C16 108.3(10) . . ? N C13 C16 102.0(7) . . ? C16' C13 C16 47.4(10) . . ? C15' C13 C16 139.5(11) . . ? C14' C14 C13 69.9(18) . . ? C14' C14 C15' 119(2) . . ? C13 C14 C15' 54.8(8) . . ? C14 C14' C13 76.5(16) . . ? C14 C14' C16 130(2) . . ? C13 C14' C16 55.2(14) . . ? C15' C15 C13 76.8(11) . . ? C15' C15 C16' 126.0(16) . . ? C13 C15 C16' 58.9(10) . . ? C15 C15' C13 62.5(10) . . ? C15 C15' C14 113.3(15) . . ? C13 C15' C14 51.5(7) . . ? C16' C16 C13 65.4(11) . . ? C16' C16 C14' 109.1(17) . . ? C13 C16 C14' 49.0(8) . . ? C16 C16' C13 67.3(9) . . ? C16 C16' C15 117.7(12) . . ? C13 C16' C15 51.7(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.211 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.040 #===END data_3 _database_code_CSD 152735 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Al N O2' _chemical_formula_weight 283.29 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1019(8) _cell_length_b 9.7458(8) _cell_length_c 16.2491(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.007(2) _cell_angle_gamma 90.00 _cell_volume 1552.2(2) _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 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 8412 _diffrn_reflns_av_R_equivalents 0.0142 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3034 _reflns_number_gt 2594 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3034 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0366 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1281 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.004 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 0.34664(4) 0.09287(4) 0.02461(2) 0.04560(18) Uani 1 1 d . . . O1 O 0.36443(10) -0.04653(10) -0.04625(6) 0.0482(3) Uani 1 1 d . . . O2 O 0.67599(14) -0.02952(15) -0.43204(8) 0.0762(4) Uani 1 1 d . . . N N 0.51227(11) -0.05019(11) -0.12786(7) 0.0436(3) Uani 1 1 d . . . C1 C 0.38617(13) -0.03770(13) -0.12171(8) 0.0415(3) Uani 1 1 d . . . C2 C 0.26343(13) -0.01996(14) -0.19293(8) 0.0427(3) Uani 1 1 d . . . C3 C 0.14189(16) -0.07772(16) -0.18302(10) 0.0550(4) Uani 1 1 d . . . H3A H 0.1402 -0.1238 -0.1332 0.066 Uiso 1 1 calc R . . C4 C 0.02375(16) -0.06675(17) -0.24709(12) 0.0634(4) Uani 1 1 d . . . H4A H -0.0566 -0.1071 -0.2406 0.076 Uiso 1 1 calc R . . C5 C 0.02501(16) 0.00375(18) -0.32028(11) 0.0615(4) Uani 1 1 d . . . H5A H -0.0541 0.0095 -0.3636 0.074 Uiso 1 1 calc R . . C6 C 0.14269(17) 0.06557(18) -0.32952(10) 0.0604(4) Uani 1 1 d . . . H6A H 0.1423 0.1155 -0.3783 0.072 Uiso 1 1 calc R . . C7 C 0.26204(15) 0.05381(16) -0.26631(9) 0.0510(3) Uani 1 1 d . . . H7A H 0.3416 0.0955 -0.2731 0.061 Uiso 1 1 calc R . . C8 C 0.54891(13) -0.04844(13) -0.20842(8) 0.0415(3) Uani 1 1 d . . . C9 C 0.62222(15) 0.06262(15) -0.22775(9) 0.0503(3) Uani 1 1 d . . . H9A H 0.6440 0.1354 -0.1899 0.060 Uiso 1 1 calc R . . C10 C 0.66279(16) 0.06519(17) -0.30282(10) 0.0565(4) Uani 1 1 d . . . H10A H 0.7113 0.1401 -0.3155 0.068 Uiso 1 1 calc R . . C11 C 0.63191(15) -0.04295(17) -0.35941(9) 0.0524(4) Uani 1 1 d . . . C12 C 0.56037(16) -0.15465(16) -0.34002(9) 0.0549(4) Uani 1 1 d . . . H12A H 0.5397 -0.2280 -0.3775 0.066 Uiso 1 1 calc R . . C13 C 0.51968(15) -0.15667(15) -0.26430(9) 0.0496(3) Uani 1 1 d . . . H13A H 0.4721 -0.2320 -0.2512 0.059 Uiso 1 1 calc R . . C14 C 0.6498(3) -0.1376(3) -0.49175(13) 0.0942(7) Uani 1 1 d . . . H14A H 0.6860 -0.1143 -0.5394 0.141 Uiso 1 1 calc R . . H14B H 0.5532 -0.1518 -0.5106 0.141 Uiso 1 1 calc R . . H14C H 0.6926 -0.2201 -0.4658 0.141 Uiso 1 1 calc R . . C15 C 0.3826(2) 0.26585(17) -0.02632(11) 0.0718(5) Uani 1 1 d . . . H15A H 0.4713 0.2626 -0.0379 0.108 Uiso 1 1 calc R . . H15B H 0.3792 0.3398 0.0121 0.108 Uiso 1 1 calc R . . H15C H 0.3148 0.2802 -0.0783 0.108 Uiso 1 1 calc R . . C16 C 0.17021(17) 0.0769(2) 0.05384(12) 0.0688(5) Uani 1 1 d . . . H16A H 0.1632 -0.0119 0.0781 0.103 Uiso 1 1 calc R . . H16B H 0.0980 0.0879 0.0036 0.103 Uiso 1 1 calc R . . H16C H 0.1630 0.1467 0.0942 0.103 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 0.0430(3) 0.0593(3) 0.0351(3) 0.00164(15) 0.01069(18) 0.00351(16) O1 0.0501(5) 0.0631(6) 0.0342(5) -0.0010(4) 0.0155(4) -0.0051(4) O2 0.0769(8) 0.1107(11) 0.0515(7) -0.0001(6) 0.0359(6) -0.0147(7) N 0.0425(6) 0.0556(6) 0.0341(6) 0.0011(4) 0.0121(4) 0.0006(5) C1 0.0443(7) 0.0460(7) 0.0352(6) -0.0007(5) 0.0117(5) -0.0038(5) C2 0.0423(7) 0.0489(7) 0.0382(6) -0.0043(5) 0.0120(5) 0.0014(5) C3 0.0490(8) 0.0619(9) 0.0538(9) 0.0035(6) 0.0119(7) -0.0056(6) C4 0.0443(8) 0.0707(10) 0.0722(11) -0.0062(8) 0.0085(7) -0.0069(7) C5 0.0489(8) 0.0776(10) 0.0519(9) -0.0138(7) 0.0004(6) 0.0108(7) C6 0.0570(9) 0.0833(11) 0.0413(8) 0.0050(7) 0.0127(7) 0.0208(7) C7 0.0432(7) 0.0663(9) 0.0458(8) 0.0058(6) 0.0152(6) 0.0064(6) C8 0.0386(6) 0.0531(7) 0.0340(6) 0.0040(5) 0.0112(5) 0.0027(5) C9 0.0517(8) 0.0551(8) 0.0451(8) -0.0022(6) 0.0138(6) -0.0083(6) C10 0.0538(8) 0.0665(9) 0.0526(9) 0.0083(7) 0.0193(7) -0.0130(7) C11 0.0457(7) 0.0758(9) 0.0394(7) 0.0061(6) 0.0173(6) 0.0008(7) C12 0.0633(9) 0.0605(9) 0.0451(8) -0.0064(6) 0.0212(6) -0.0034(7) C13 0.0571(8) 0.0498(7) 0.0457(7) 0.0019(6) 0.0200(6) -0.0058(6) C14 0.1091(15) 0.1331(19) 0.0525(10) -0.0115(11) 0.0434(10) -0.0035(15) C15 0.0897(12) 0.0627(9) 0.0587(9) 0.0092(8) 0.0096(8) 0.0014(9) C16 0.0460(8) 0.1027(13) 0.0590(10) -0.0067(9) 0.0151(7) 0.0079(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 O1 1.8177(10) . ? Al C15 1.9503(17) . ? Al C16 1.9587(17) . ? Al N 1.9650(11) 3_655 ? O1 C1 1.2997(15) . ? O2 C11 1.3648(17) . ? O2 C14 1.413(3) . ? N C1 1.3073(18) . ? N C8 1.4442(16) . ? N Al 1.9650(11) 3_655 ? C1 C2 1.4872(18) . ? C2 C7 1.390(2) . ? C2 C3 1.395(2) . ? C3 C4 1.385(2) . ? C4 C5 1.376(2) . ? C5 C6 1.373(3) . ? C6 C7 1.386(2) . ? C8 C13 1.3764(19) . ? C8 C9 1.3897(19) . ? C9 C10 1.378(2) . ? C10 C11 1.384(2) . ? C11 C12 1.385(2) . ? C12 C13 1.3885(18) . ? 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 C15 108.67(6) . . ? O1 Al C16 109.23(7) . . ? C15 Al C16 116.45(9) . . ? O1 Al N 102.72(5) . 3_655 ? C15 Al N 111.98(7) . 3_655 ? C16 Al N 106.90(6) . 3_655 ? C1 O1 Al 127.83(8) . . ? C11 O2 C14 118.45(15) . . ? C1 N C8 122.44(11) . . ? C1 N Al 118.25(9) . 3_655 ? C8 N Al 118.97(8) . 3_655 ? O1 C1 N 117.14(11) . . ? O1 C1 C2 116.25(11) . . ? N C1 C2 126.56(11) . . ? C7 C2 C3 118.79(12) . . ? C7 C2 C1 124.14(12) . . ? C3 C2 C1 117.04(12) . . ? C4 C3 C2 120.29(15) . . ? C5 C4 C3 120.11(15) . . ? C6 C5 C4 120.20(13) . . ? C5 C6 C7 120.23(15) . . ? C6 C7 C2 120.32(14) . . ? C13 C8 C9 119.26(12) . . ? C13 C8 N 121.85(11) . . ? C9 C8 N 118.79(12) . . ? C10 C9 C8 120.21(13) . . ? C9 C10 C11 120.46(13) . . ? O2 C11 C10 115.68(14) . . ? O2 C11 C12 124.74(14) . . ? C10 C11 C12 119.58(14) . . ? C11 C12 C13 119.71(14) . . ? C8 C13 C12 120.76(13) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.253 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.050 #===END data_7 _database_code_CSD 139979 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H31 Al Cl2 N2' _chemical_formula_weight 541.47 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 9.8996(7) _cell_length_b 25.1651(18) _cell_length_c 12.5368(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.797(2) _cell_angle_gamma 90.00 _cell_volume 3112.3(4) _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 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 17736 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.04 _reflns_number_total 6131 _reflns_number_gt 2837 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6131 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1503 _refine_ls_R_factor_gt 0.0771 _refine_ls_wR_factor_ref 0.2463 _refine_ls_wR_factor_gt 0.2182 _refine_ls_goodness_of_fit_ref 1.236 _refine_ls_restrained_S_all 1.236 _refine_ls_shift/su_max 0.344 _refine_ls_shift/su_mean 0.018 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 0.0763(2) 0.16944(6) 0.23112(13) 0.0878(6) Uani 1 1 d . . . Cl1 Cl 0.20712(15) 0.40944(4) -0.02208(12) 0.0911(5) Uani 1 1 d . . . Cl2 Cl 0.24004(15) 0.02201(5) 0.69568(9) 0.0873(5) Uani 1 1 d . . . N1 N 0.1582(4) 0.18314(12) 0.1005(3) 0.0631(10) Uani 1 1 d . . . N2 N 0.1709(4) 0.10272(12) 0.2503(3) 0.0609(10) Uani 1 1 d . . . C1 C 0.1863(4) 0.14411(15) 0.0326(3) 0.0556(11) Uani 1 1 d . . . C2 C 0.1965(5) 0.09044(15) 0.0625(3) 0.0574(11) Uani 1 1 d . . . C3 C 0.2006(4) 0.07243(15) 0.1680(3) 0.0536(10) Uani 1 1 d . . . C4 C 0.1728(5) 0.23798(15) 0.0691(3) 0.0593(11) Uani 1 1 d . . . C5 C 0.0615(5) 0.27108(17) 0.0653(4) 0.0693(13) Uani 1 1 d . . . H5A H -0.0218 0.2577 0.0817 0.083 Uiso 1 1 calc R . . C6 C 0.0722(5) 0.32305(16) 0.0378(4) 0.0703(13) Uani 1 1 d . . . H6A H -0.0037 0.3450 0.0345 0.084 Uiso 1 1 calc R . . C7 C 0.1944(5) 0.34296(16) 0.0149(4) 0.0629(12) Uani 1 1 d . . . C8 C 0.3071(5) 0.31211(17) 0.0201(4) 0.0687(13) Uani 1 1 d . . . H8A H 0.3903 0.3263 0.0054 0.082 Uiso 1 1 calc R . . C9 C 0.2962(5) 0.25889(17) 0.0477(3) 0.0657(12) Uani 1 1 d . . . H9A H 0.3727 0.2373 0.0517 0.079 Uiso 1 1 calc R . . C10 C 0.2008(5) 0.15911(15) -0.0815(3) 0.0584(11) Uani 1 1 d . . . C11 C 0.0910(6) 0.17747(18) -0.1434(4) 0.0771(14) Uani 1 1 d . . . H11A H 0.0084 0.1814 -0.1139 0.093 Uiso 1 1 calc R . . C12 C 0.1012(8) 0.1905(2) -0.2515(5) 0.1024(19) Uani 1 1 d . . . H12A H 0.0261 0.2028 -0.2940 0.123 Uiso 1 1 calc R . . C13 C 0.2243(9) 0.1847(2) -0.2931(5) 0.099(2) Uani 1 1 d . . . H13A H 0.2325 0.1930 -0.3645 0.118 Uiso 1 1 calc R . . C14 C 0.3353(7) 0.1667(2) -0.2308(5) 0.0930(18) Uani 1 1 d . . . H14A H 0.4181 0.1629 -0.2600 0.112 Uiso 1 1 calc R . . C15 C 0.3242(5) 0.15440(17) -0.1266(4) 0.0741(14) Uani 1 1 d . . . H15A H 0.4002 0.1426 -0.0846 0.089 Uiso 1 1 calc R . . C16 C 0.2016(6) 0.04925(17) -0.0261(4) 0.0828(16) Uani 1 1 d . . . H16A H 0.1981 0.0668 -0.0942 0.124 Uiso 1 1 calc R . . H16B H 0.1257 0.0256 -0.0245 0.124 Uiso 1 1 calc R . . H16C H 0.2843 0.0293 -0.0153 0.124 Uiso 1 1 calc R . . C17 C 0.2340(5) 0.01553(16) 0.1891(3) 0.0564(11) Uani 1 1 d . . . C18 C 0.3630(6) -0.0033(2) 0.1812(4) 0.0827(15) Uani 1 1 d . . . H18A H 0.4313 0.0198 0.1638 0.099 Uiso 1 1 calc R . . C19 C 0.3916(8) -0.0574(3) 0.1994(5) 0.112(2) Uani 1 1 d . . . H19A H 0.4793 -0.0700 0.1949 0.134 Uiso 1 1 calc R . . C20 C 0.2935(10) -0.0908(2) 0.2232(5) 0.112(2) Uani 1 1 d . . . H20A H 0.3129 -0.1267 0.2337 0.135 Uiso 1 1 calc R . . C21 C 0.1634(9) -0.0723(2) 0.2322(4) 0.103(2) Uani 1 1 d . . . H21A H 0.0954 -0.0957 0.2487 0.124 Uiso 1 1 calc R . . C22 C 0.1348(5) -0.01937(17) 0.2167(4) 0.0728(13) Uani 1 1 d . . . H22A H 0.0479 -0.0068 0.2249 0.087 Uiso 1 1 calc R . . C23 C 0.1908(5) 0.08249(15) 0.3577(3) 0.0570(11) Uani 1 1 d . . . C24 C 0.3164(5) 0.07079(16) 0.4046(3) 0.0626(12) Uani 1 1 d . . . H24A H 0.3917 0.0749 0.3656 0.075 Uiso 1 1 calc R . . C25 C 0.3340(5) 0.05273(16) 0.5104(4) 0.0634(12) Uani 1 1 d . . . H25A H 0.4201 0.0453 0.5423 0.076 Uiso 1 1 calc R . . C26 C 0.2213(5) 0.04626(16) 0.5660(3) 0.0579(11) Uani 1 1 d . . . C27 C 0.0965(6) 0.05836(17) 0.5213(4) 0.0710(13) Uani 1 1 d . . . H27A H 0.0219 0.0543 0.5610 0.085 Uiso 1 1 calc R . . C28 C 0.0781(5) 0.07688(17) 0.4160(3) 0.0641(12) Uani 1 1 d . . . H28A H -0.0081 0.0853 0.3854 0.077 Uiso 1 1 calc R . . C29 C 0.1285(10) 0.2182(2) 0.3416(6) 0.150(3) Uani 1 1 d . . . H29A H 0.0722 0.2496 0.3301 0.180 Uiso 1 1 calc R . . H29B H 0.1064 0.2025 0.4086 0.180 Uiso 1 1 calc R . . C30 C 0.2578(12) 0.2345(5) 0.3546(9) 0.243(7) Uani 1 1 d . . . H30A H 0.2684 0.2593 0.4127 0.365 Uiso 1 1 calc R . . H30B H 0.2819 0.2513 0.2901 0.365 Uiso 1 1 calc R . . H30C H 0.3158 0.2044 0.3703 0.365 Uiso 1 1 calc R . . C31 C -0.1217(8) 0.1612(3) 0.2072(7) 0.135(3) Uani 1 1 d . . . H31A H -0.1560 0.1494 0.2735 0.161 Uiso 1 1 calc R . . H31B H -0.1612 0.1957 0.1900 0.161 Uiso 1 1 calc R . . C32 C -0.1682(10) 0.1241(5) 0.1224(10) 0.222(5) Uani 1 1 d . . . H32A H -0.2654 0.1226 0.1165 0.333 Uiso 1 1 calc R . . H32B H -0.1323 0.0893 0.1394 0.333 Uiso 1 1 calc R . . H32C H -0.1374 0.1358 0.0558 0.333 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 0.1405(16) 0.0623(9) 0.0659(10) 0.0047(7) 0.0403(9) 0.0160(9) Cl1 0.1075(11) 0.0516(7) 0.1187(12) 0.0187(7) 0.0354(8) -0.0003(7) Cl2 0.1265(12) 0.0902(9) 0.0461(7) 0.0082(6) 0.0129(6) -0.0089(8) N1 0.099(3) 0.0427(18) 0.049(2) 0.0016(16) 0.0167(18) 0.0007(19) N2 0.094(3) 0.0496(19) 0.041(2) 0.0034(16) 0.0163(18) 0.0027(18) C1 0.072(3) 0.054(2) 0.042(2) 0.0001(19) 0.0142(19) 0.000(2) C2 0.087(3) 0.044(2) 0.043(2) -0.0009(18) 0.015(2) 0.003(2) C3 0.063(3) 0.046(2) 0.053(3) -0.0014(19) 0.013(2) -0.002(2) C4 0.088(4) 0.047(2) 0.044(2) -0.0011(18) 0.012(2) 0.002(3) C5 0.076(3) 0.054(3) 0.083(3) 0.008(2) 0.030(2) 0.001(2) C6 0.077(3) 0.055(3) 0.083(3) 0.011(2) 0.028(3) 0.011(2) C7 0.082(4) 0.047(2) 0.062(3) 0.003(2) 0.018(2) 0.003(2) C8 0.076(4) 0.056(3) 0.076(3) 0.000(2) 0.019(2) -0.005(3) C9 0.072(3) 0.062(3) 0.064(3) 0.000(2) 0.010(2) 0.005(2) C10 0.087(4) 0.046(2) 0.043(2) -0.0001(18) 0.013(2) 0.000(2) C11 0.093(4) 0.077(3) 0.061(3) 0.005(3) 0.005(3) -0.001(3) C12 0.141(6) 0.099(4) 0.063(4) 0.013(3) -0.012(4) -0.003(4) C13 0.164(7) 0.080(4) 0.054(3) 0.004(3) 0.029(4) -0.015(4) C14 0.132(5) 0.081(4) 0.072(4) 0.010(3) 0.046(4) -0.002(3) C15 0.100(4) 0.067(3) 0.058(3) 0.006(2) 0.020(3) 0.012(3) C16 0.143(5) 0.054(3) 0.052(3) -0.003(2) 0.015(3) 0.001(3) C17 0.075(3) 0.050(2) 0.045(2) 0.0021(18) 0.010(2) 0.001(2) C18 0.088(4) 0.072(3) 0.090(4) -0.008(3) 0.022(3) 0.004(3) C19 0.136(6) 0.085(4) 0.113(5) -0.002(4) 0.002(4) 0.053(4) C20 0.192(8) 0.056(4) 0.089(5) 0.013(3) 0.008(5) 0.011(5) C21 0.168(7) 0.067(4) 0.076(4) 0.007(3) 0.018(4) -0.030(4) C22 0.097(4) 0.056(3) 0.067(3) 0.000(2) 0.014(3) -0.007(3) C23 0.083(4) 0.046(2) 0.043(2) 0.0009(18) 0.014(2) -0.005(2) C24 0.075(4) 0.062(3) 0.053(3) 0.003(2) 0.017(2) -0.010(2) C25 0.076(3) 0.059(3) 0.056(3) 0.001(2) 0.006(2) -0.004(2) C26 0.085(4) 0.048(2) 0.042(2) -0.0017(18) 0.010(2) -0.013(2) C27 0.097(4) 0.066(3) 0.053(3) -0.003(2) 0.027(3) -0.012(3) C28 0.072(3) 0.073(3) 0.049(3) 0.002(2) 0.012(2) 0.000(2) C29 0.286(12) 0.075(4) 0.094(5) -0.008(4) 0.044(6) -0.022(5) C30 0.259(13) 0.264(13) 0.189(11) 0.014(9) -0.084(10) -0.127(11) C31 0.136(7) 0.142(6) 0.133(7) 0.062(5) 0.056(5) 0.041(5) C32 0.134(9) 0.314(15) 0.220(13) 0.007(12) 0.028(8) -0.011(9) _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 C29 1.890(7) . ? Al N1 1.918(4) . ? Al N2 1.928(4) . ? Al C31 1.969(8) . ? Cl1 C7 1.744(4) . ? Cl2 C26 1.731(4) . ? N1 C1 1.344(5) . ? N1 C4 1.446(5) . ? N2 C3 1.335(5) . ? N2 C23 1.438(5) . ? C1 C2 1.403(5) . ? C1 C10 1.498(5) . ? C2 C3 1.396(5) . ? C2 C16 1.523(5) . ? C3 C17 1.488(5) . ? C4 C9 1.377(6) . ? C4 C5 1.379(6) . ? C5 C6 1.359(6) . ? C6 C7 1.362(6) . ? C7 C8 1.356(6) . ? C8 C9 1.390(6) . ? C10 C11 1.363(6) . ? C10 C15 1.394(6) . ? C11 C12 1.406(7) . ? C12 C13 1.373(8) . ? C13 C14 1.371(8) . ? C14 C15 1.355(7) . ? C17 C18 1.373(6) . ? C17 C22 1.383(6) . ? C18 C19 1.405(7) . ? C19 C20 1.338(9) . ? C20 C21 1.383(9) . ? C21 C22 1.373(7) . ? C23 C24 1.362(6) . ? C23 C28 1.392(6) . ? C24 C25 1.399(6) . ? C25 C26 1.374(6) . ? C26 C27 1.348(6) . ? C27 C28 1.398(6) . ? C29 C30 1.341(12) . ? C31 C32 1.460(12) . ? 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 C29 Al N1 113.6(3) . . ? C29 Al N2 112.0(3) . . ? N1 Al N2 91.57(15) . . ? C29 Al C31 112.8(4) . . ? N1 Al C31 112.0(3) . . ? N2 Al C31 113.2(3) . . ? C1 N1 C4 119.6(3) . . ? C1 N1 Al 122.3(3) . . ? C4 N1 Al 117.6(3) . . ? C3 N2 C23 120.0(3) . . ? C3 N2 Al 122.5(3) . . ? C23 N2 Al 116.9(3) . . ? N1 C1 C2 123.3(4) . . ? N1 C1 C10 117.5(3) . . ? C2 C1 C10 119.1(3) . . ? C3 C2 C1 124.1(3) . . ? C3 C2 C16 118.0(3) . . ? C1 C2 C16 117.9(4) . . ? N2 C3 C2 123.8(4) . . ? N2 C3 C17 118.2(4) . . ? C2 C3 C17 118.0(3) . . ? C9 C4 C5 118.8(4) . . ? C9 C4 N1 121.9(4) . . ? C5 C4 N1 119.2(4) . . ? C6 C5 C4 120.7(4) . . ? C5 C6 C7 119.8(4) . . ? C8 C7 C6 121.4(4) . . ? C8 C7 Cl1 119.0(4) . . ? C6 C7 Cl1 119.6(4) . . ? C7 C8 C9 118.8(4) . . ? C4 C9 C8 120.4(4) . . ? C11 C10 C15 118.8(4) . . ? C11 C10 C1 119.6(4) . . ? C15 C10 C1 121.6(4) . . ? C10 C11 C12 120.7(5) . . ? C13 C12 C11 118.6(6) . . ? C14 C13 C12 120.9(6) . . ? C15 C14 C13 119.9(6) . . ? C14 C15 C10 121.1(5) . . ? C18 C17 C22 118.9(4) . . ? C18 C17 C3 120.9(4) . . ? C22 C17 C3 120.2(4) . . ? C17 C18 C19 119.9(5) . . ? C20 C19 C18 120.4(6) . . ? C19 C20 C21 120.4(6) . . ? C22 C21 C20 119.8(6) . . ? C21 C22 C17 120.7(5) . . ? C24 C23 C28 119.7(4) . . ? C24 C23 N2 122.0(4) . . ? C28 C23 N2 118.3(4) . . ? C23 C24 C25 121.0(4) . . ? C26 C25 C24 118.6(4) . . ? C27 C26 C25 121.1(4) . . ? C27 C26 Cl2 119.5(4) . . ? C25 C26 Cl2 119.4(4) . . ? C26 C27 C28 120.7(4) . . ? C23 C28 C27 118.9(5) . . ? C30 C29 Al 119.1(8) . . ? C32 C31 Al 115.3(6) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.882 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.076 #===END data_8 _database_code_CSD 139980 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H25 Al Cl2 N2' _chemical_formula_weight 499.39 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)/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 7.3864(5) _cell_length_b 20.7461(14) _cell_length_c 17.5176(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.0910(10) _cell_angle_gamma 90.00 _cell_volume 2657.7(3) _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 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 14731 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.02 _reflns_number_total 5226 _reflns_number_gt 4214 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5226 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0528 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1407 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 0.08542(7) 0.33345(2) 0.55113(3) 0.04660(17) Uani 1 1 d . . . Cl1 Cl 0.83596(8) 0.54008(3) 0.64406(4) 0.0893(2) Uani 1 1 d . . . Cl2 Cl -0.21987(8) 0.04052(3) 0.38017(3) 0.0825(2) Uani 1 1 d . . . N1 N 0.20415(19) 0.36430(7) 0.64931(8) 0.0465(3) Uani 1 1 d . . . N2 N -0.0271(2) 0.26080(7) 0.59311(8) 0.0508(4) Uani 1 1 d . . . C1 C 0.1500(2) 0.34884(8) 0.71655(10) 0.0463(4) Uani 1 1 d . . . C2 C 0.0155(2) 0.30211(8) 0.72239(10) 0.0504(4) Uani 1 1 d . . . H2A H -0.0258 0.2992 0.7700 0.061 Uiso 1 1 calc R . . C3 C -0.0640(2) 0.25955(8) 0.66597(10) 0.0484(4) Uani 1 1 d . . . C4 C 0.3594(2) 0.40607(8) 0.64805(9) 0.0441(4) Uani 1 1 d . . . C5 C 0.3400(3) 0.46220(9) 0.60491(11) 0.0541(4) Uani 1 1 d . . . H5A H 0.2270 0.4722 0.5770 0.065 Uiso 1 1 calc R . . C6 C 0.4857(3) 0.50346(9) 0.60276(11) 0.0561(4) Uani 1 1 d . . . H6A H 0.4718 0.5413 0.5740 0.067 Uiso 1 1 calc R . . C7 C 0.6525(2) 0.48737(9) 0.64416(11) 0.0542(4) Uani 1 1 d . . . C8 C 0.6765(2) 0.43075(10) 0.68466(11) 0.0559(4) Uani 1 1 d . . . H8A H 0.7910 0.4200 0.7107 0.067 Uiso 1 1 calc R . . C9 C 0.5298(2) 0.38968(8) 0.68668(10) 0.0491(4) Uani 1 1 d . . . H9A H 0.5456 0.3511 0.7139 0.059 Uiso 1 1 calc R . . C10 C 0.2224(2) 0.38285(9) 0.78959(10) 0.0491(4) Uani 1 1 d . . . C11 C 0.2220(3) 0.44987(10) 0.79360(12) 0.0590(5) Uani 1 1 d . . . H11A H 0.1858 0.4741 0.7494 0.071 Uiso 1 1 calc R . . C12 C 0.2756(3) 0.48042(13) 0.86338(15) 0.0754(6) Uani 1 1 d . . . H12A H 0.2747 0.5252 0.8660 0.090 Uiso 1 1 calc R . . C13 C 0.3296(3) 0.44526(15) 0.92836(14) 0.0824(7) Uani 1 1 d . . . H13A H 0.3647 0.4662 0.9751 0.099 Uiso 1 1 calc R . . C14 C 0.3325(3) 0.37877(14) 0.92513(12) 0.0752(6) Uani 1 1 d . . . H14A H 0.3710 0.3550 0.9695 0.090 Uiso 1 1 calc R . . C15 C 0.2785(3) 0.34764(11) 0.85653(11) 0.0602(5) Uani 1 1 d . . . H15A H 0.2794 0.3028 0.8547 0.072 Uiso 1 1 calc R . . C16 C -0.2050(2) 0.21446(9) 0.68900(10) 0.0529(4) Uani 1 1 d . . . C17 C -0.1693(3) 0.17572(11) 0.75410(13) 0.0741(6) Uani 1 1 d . . . H17A H -0.0539 0.1763 0.7833 0.089 Uiso 1 1 calc R . . C18 C -0.3045(5) 0.13631(16) 0.77576(16) 0.1043(10) Uani 1 1 d . . . H18A H -0.2790 0.1095 0.8185 0.125 Uiso 1 1 calc R . . C19 C -0.4766(5) 0.13689(19) 0.7339(2) 0.1192(12) Uani 1 1 d . . . H19A H -0.5682 0.1109 0.7487 0.143 Uiso 1 1 calc R . . C20 C -0.5127(4) 0.17572(17) 0.6706(2) 0.1061(10) Uani 1 1 d . . . H20A H -0.6299 0.1764 0.6430 0.127 Uiso 1 1 calc R . . C21 C -0.3781(3) 0.21398(13) 0.64701(14) 0.0741(6) Uani 1 1 d . . . H21A H -0.4038 0.2393 0.6030 0.089 Uiso 1 1 calc R . . C22 C -0.0772(2) 0.20701(9) 0.54297(10) 0.0503(4) Uani 1 1 d . . . C23 C -0.0294(2) 0.14441(9) 0.56515(10) 0.0536(4) Uani 1 1 d . . . H23A H 0.0334 0.1367 0.6141 0.064 Uiso 1 1 calc R . . C24 C -0.0736(2) 0.09345(10) 0.51563(11) 0.0576(5) Uani 1 1 d . . . H24A H -0.0426 0.0516 0.5313 0.069 Uiso 1 1 calc R . . C25 C -0.1643(3) 0.10505(11) 0.44252(11) 0.0600(5) Uani 1 1 d . . . C26 C -0.2107(3) 0.16658(12) 0.41856(12) 0.0688(6) Uani 1 1 d . . . H26A H -0.2707 0.1739 0.3690 0.083 Uiso 1 1 calc R . . C27 C -0.1673(3) 0.21786(11) 0.46883(11) 0.0655(5) Uani 1 1 d . . . H27A H -0.1985 0.2596 0.4528 0.079 Uiso 1 1 calc R . . C28 C 0.2693(3) 0.30687(11) 0.48773(13) 0.0675(5) Uani 1 1 d . . . H28A H 0.3547 0.2781 0.5167 0.101 Uiso 1 1 calc R . . H28B H 0.3331 0.3441 0.4729 0.101 Uiso 1 1 calc R . . H28C H 0.2107 0.2853 0.4424 0.101 Uiso 1 1 calc R . . C29 C -0.1071(3) 0.39269(10) 0.50576(11) 0.0633(5) Uani 1 1 d . . . H29A H -0.1875 0.4020 0.5429 0.095 Uiso 1 1 calc R . . H29B H -0.1755 0.3731 0.4611 0.095 Uiso 1 1 calc R . . H29C H -0.0526 0.4320 0.4911 0.095 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 0.0540(3) 0.0447(3) 0.0407(3) 0.0064(2) 0.0053(2) -0.0019(2) Cl1 0.0662(4) 0.0754(4) 0.1295(6) 0.0055(4) 0.0249(3) -0.0216(3) Cl2 0.0777(4) 0.1006(5) 0.0689(4) -0.0313(3) 0.0097(3) -0.0132(3) N1 0.0493(8) 0.0444(7) 0.0449(8) 0.0049(6) 0.0039(6) -0.0029(6) N2 0.0547(8) 0.0526(8) 0.0432(7) 0.0080(6) 0.0002(6) -0.0086(7) C1 0.0472(9) 0.0462(9) 0.0453(9) 0.0032(7) 0.0055(7) 0.0022(7) C2 0.0551(10) 0.0513(10) 0.0454(9) 0.0049(7) 0.0090(7) -0.0046(8) C3 0.0459(9) 0.0487(9) 0.0492(9) 0.0096(7) 0.0013(7) -0.0011(7) C4 0.0508(9) 0.0408(8) 0.0410(8) 0.0010(6) 0.0079(7) -0.0010(7) C5 0.0543(10) 0.0502(10) 0.0564(10) 0.0094(8) 0.0029(8) 0.0005(8) C6 0.0627(11) 0.0438(9) 0.0633(11) 0.0095(8) 0.0139(9) 0.0016(8) C7 0.0528(10) 0.0503(10) 0.0633(11) -0.0041(8) 0.0217(8) -0.0053(8) C8 0.0456(9) 0.0635(11) 0.0596(11) 0.0034(9) 0.0111(8) 0.0041(8) C9 0.0519(9) 0.0475(9) 0.0486(9) 0.0047(7) 0.0089(7) 0.0058(7) C10 0.0448(9) 0.0564(10) 0.0473(9) -0.0022(7) 0.0110(7) -0.0026(7) C11 0.0557(10) 0.0595(11) 0.0642(12) -0.0069(9) 0.0174(9) -0.0014(8) C12 0.0728(13) 0.0741(14) 0.0849(16) -0.0315(12) 0.0304(11) -0.0157(11) C13 0.0697(13) 0.117(2) 0.0634(14) -0.0321(14) 0.0215(11) -0.0296(14) C14 0.0682(13) 0.108(2) 0.0495(11) -0.0038(11) 0.0079(9) -0.0177(13) C15 0.0611(11) 0.0726(13) 0.0471(10) 0.0029(9) 0.0087(8) -0.0082(9) C16 0.0529(10) 0.0536(10) 0.0521(10) 0.0062(8) 0.0069(8) -0.0069(8) C17 0.0789(14) 0.0794(14) 0.0615(12) 0.0183(11) 0.0015(10) -0.0240(12) C18 0.125(2) 0.112(2) 0.0767(17) 0.0295(15) 0.0173(16) -0.0475(19) C19 0.105(2) 0.151(3) 0.106(2) 0.021(2) 0.0287(18) -0.068(2) C20 0.0634(15) 0.141(3) 0.112(2) 0.0144(19) 0.0076(14) -0.0401(16) C21 0.0544(11) 0.0896(16) 0.0767(14) 0.0129(12) 0.0041(10) -0.0132(11) C22 0.0497(9) 0.0542(10) 0.0454(9) 0.0057(7) 0.0015(7) -0.0109(8) C23 0.0537(10) 0.0603(11) 0.0459(9) 0.0041(8) 0.0038(7) -0.0046(8) C24 0.0553(10) 0.0615(11) 0.0560(10) -0.0027(9) 0.0083(8) -0.0037(9) C25 0.0507(10) 0.0771(13) 0.0534(10) -0.0086(10) 0.0122(8) -0.0149(9) C26 0.0671(12) 0.0906(16) 0.0447(10) 0.0038(10) -0.0059(9) -0.0185(11) C27 0.0729(13) 0.0657(12) 0.0534(11) 0.0115(9) -0.0063(9) -0.0107(10) C28 0.0743(13) 0.0660(13) 0.0644(12) -0.0048(10) 0.0171(10) 0.0015(10) C29 0.0695(12) 0.0654(12) 0.0536(11) 0.0097(9) 0.0033(9) 0.0063(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 Al N2 1.9170(15) . ? Al N1 1.9266(15) . ? Al C28 1.951(2) . ? Al C29 1.961(2) . ? Cl1 C7 1.7418(18) . ? Cl2 C25 1.740(2) . ? N1 C1 1.335(2) . ? N1 C4 1.440(2) . ? N2 C3 1.343(2) . ? N2 C22 1.436(2) . ? C1 C2 1.402(2) . ? C1 C10 1.493(2) . ? C2 C3 1.392(2) . ? C3 C16 1.497(2) . ? C4 C5 1.385(2) . ? C4 C9 1.385(2) . ? C5 C6 1.380(3) . ? C6 C7 1.380(3) . ? C7 C8 1.371(3) . ? C8 C9 1.383(3) . ? C10 C11 1.392(3) . ? C10 C15 1.394(3) . ? C11 C12 1.384(3) . ? C12 C13 1.363(4) . ? C13 C14 1.381(4) . ? C14 C15 1.373(3) . ? C16 C21 1.382(3) . ? C16 C17 1.390(3) . ? C17 C18 1.384(3) . ? C18 C19 1.375(4) . ? C19 C20 1.366(5) . ? C20 C21 1.380(3) . ? C22 C23 1.387(3) . ? C22 C27 1.392(3) . ? C23 C24 1.377(3) . ? C24 C25 1.380(3) . ? C25 C26 1.372(3) . ? C26 C27 1.389(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 N2 Al N1 94.94(6) . . ? N2 Al C28 111.72(9) . . ? N1 Al C28 109.64(8) . . ? N2 Al C29 108.63(8) . . ? N1 Al C29 111.51(8) . . ? C28 Al C29 118.01(9) . . ? C1 N1 C4 119.73(14) . . ? C1 N1 Al 123.54(12) . . ? C4 N1 Al 116.72(10) . . ? C3 N2 C22 119.80(14) . . ? C3 N2 Al 122.48(12) . . ? C22 N2 Al 117.70(11) . . ? N1 C1 C2 122.25(15) . . ? N1 C1 C10 121.82(15) . . ? C2 C1 C10 115.85(15) . . ? C3 C2 C1 128.26(16) . . ? N2 C3 C2 122.73(15) . . ? N2 C3 C16 120.70(15) . . ? C2 C3 C16 116.43(15) . . ? C5 C4 C9 119.38(16) . . ? C5 C4 N1 119.52(15) . . ? C9 C4 N1 121.05(15) . . ? C6 C5 C4 121.01(17) . . ? C5 C6 C7 118.54(17) . . ? C8 C7 C6 121.35(17) . . ? C8 C7 Cl1 119.64(15) . . ? C6 C7 Cl1 119.01(15) . . ? C7 C8 C9 119.77(17) . . ? C8 C9 C4 119.84(16) . . ? C11 C10 C15 118.90(17) . . ? C11 C10 C1 120.82(16) . . ? C15 C10 C1 120.10(17) . . ? C12 C11 C10 120.0(2) . . ? C13 C12 C11 120.4(2) . . ? C12 C13 C14 120.3(2) . . ? C15 C14 C13 120.1(2) . . ? C14 C15 C10 120.3(2) . . ? C21 C16 C17 119.15(19) . . ? C21 C16 C3 119.19(16) . . ? C17 C16 C3 121.56(16) . . ? C18 C17 C16 120.4(2) . . ? C19 C18 C17 119.8(3) . . ? C20 C19 C18 119.9(2) . . ? C19 C20 C21 121.0(3) . . ? C20 C21 C16 119.7(2) . . ? C23 C22 C27 118.83(17) . . ? C23 C22 N2 121.51(15) . . ? C27 C22 N2 119.57(17) . . ? C24 C23 C22 120.93(17) . . ? C23 C24 C25 119.44(19) . . ? C26 C25 C24 120.91(19) . . ? C26 C25 Cl2 119.80(16) . . ? C24 C25 Cl2 119.28(17) . . ? C25 C26 C27 119.54(18) . . ? C26 C27 C22 120.3(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.262 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.040 #===END