# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sg090268 _database_code_depnum_ccdc_archive 'CCDC 916837' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C6 H18 Al N' _chemical_formula_sum 'C6 H18 Al N' _exptl_crystal_recrystallization_method sublimation _chemical_melting_point ? _exptl_crystal_description Irregular _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 131.19 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 orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' _symmetry_int_tables_number 62 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 12.186(5) _cell_length_b 11.131(4) _cell_length_c 6.739(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 914.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 2493 _cell_measurement_theta_min 3.344 _cell_measurement_theta_max 27.051 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.953 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9447 _exptl_absorpt_correction_T_max 0.9649 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5894 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_unetI/netI 0.0188 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1089 _reflns_number_gt 892 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0447P)^2^+0.1849P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1089 _refine_ls_number_parameters 93 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.248 _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 0.85138(5) 0.7500 1.05515(8) 0.0356(2) Uani 1 2 d S . . N1 N 0.96012(13) 0.7500 0.8281(2) 0.0321(4) Uani 1 2 d SD . . C1 C 1.0630(2) 0.6809(2) 0.8904(4) 0.0370(6) Uani 0.50 1 d PD . 1 C2 C 1.1229(2) 0.7500 1.0624(4) 0.0538(6) Uani 1 2 d SD . 1 C3 C 0.9909(3) 0.6279(2) 0.7656(5) 0.0411(6) Uani 0.50 1 d PD . 2 C4 C 0.8971(17) 0.5526(17) 0.691(4) 0.0485(19) Uani 0.50 1 d PD . 2 H4A H 0.8370 0.5544 0.7870 0.073 Uiso 0.50 1 calc PR . 2 H4B H 0.9219 0.4696 0.6722 0.073 Uiso 0.50 1 calc PR . 2 H4C H 0.8714 0.5848 0.5634 0.073 Uiso 0.50 1 calc PR . 2 C5 C 0.9144(3) 0.6813(3) 0.6514(4) 0.0407(7) Uani 0.50 1 d PD . 3 C6 C 0.8783(18) 0.5544(16) 0.684(4) 0.0485(19) Uani 0.50 1 d PD . 3 H6A H 0.9419 0.5051 0.7203 0.073 Uiso 0.50 1 calc PR . 3 H6B H 0.8451 0.5230 0.5625 0.073 Uiso 0.50 1 calc PR . 3 H6C H 0.8243 0.5520 0.7921 0.073 Uiso 0.50 1 calc PR . 3 H1 H 0.8783(14) 0.6380(16) 1.171(3) 0.054(5) Uiso 1 1 d . . . H2 H 0.736(2) 0.7500 0.954(4) 0.057(7) Uiso 1 2 d S . . H1A H 1.0338(14) 0.5935(17) 0.904(3) 0.055(5) Uiso 1 1 d . . . H5A H 0.850(2) 0.7500 0.616(5) 0.075(9) Uiso 1 2 d S . . H2A H 1.1667(18) 0.6924(19) 1.068(3) 0.076(7) Uiso 1 1 d . . . H2B H 1.074(2) 0.7500 1.176(4) 0.057(7) Uiso 1 2 d S . . H1B H 1.114(3) 0.681(3) 0.769(6) 0.058(10) Uiso 0.50 1 d P . . H3B H 1.050(4) 0.643(3) 0.668(6) 0.062(11) Uiso 0.50 1 d P . . H5B H 0.968(3) 0.689(3) 0.547(5) 0.046(9) 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 0.0311(3) 0.0479(4) 0.0278(3) 0.000 0.0016(2) 0.000 N1 0.0359(9) 0.0348(8) 0.0257(7) 0.000 0.0001(6) 0.000 C1 0.0332(14) 0.0405(15) 0.0372(14) 0.0009(12) 0.0048(12) -0.0005(11) C2 0.0323(11) 0.0717(17) 0.0572(16) 0.000 -0.0076(11) 0.000 C3 0.0505(17) 0.0344(13) 0.0386(14) -0.0033(12) 0.0086(14) 0.0028(12) C4 0.062(5) 0.0387(8) 0.0450(14) -0.0063(10) -0.008(3) -0.003(2) C5 0.0543(18) 0.0400(15) 0.0278(13) -0.0030(11) -0.0030(13) 0.0014(13) C6 0.062(5) 0.0387(8) 0.0450(14) -0.0063(10) -0.008(3) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al1 N1 2.0240(17) . ? Al1 H1 1.507(18) . ? Al1 H2 1.56(3) . ? N1 C3 1.471(3) 7_575 ? N1 C3 1.471(3) . ? N1 C5 1.521(3) . ? N1 C5 1.521(3) 7_575 ? N1 C1 1.530(3) 7_575 ? N1 C1 1.530(3) . ? C1 C1 1.538(6) 7_575 ? C1 C2 1.571(4) . ? C1 H1A 1.040(19) . ? C1 H1B 1.02(4) . ? C2 C1 1.571(4) 7_575 ? C2 H2A 0.84(2) . ? C2 H2B 0.97(3) . ? C3 C4 1.505(15) . ? C3 H1A 1.137(18) . ? C3 H3B 0.99(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.496(17) . ? C5 C5 1.530(6) 7_575 ? C5 H5A 1.13(2) . ? C5 H5B 0.96(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 H1 104.4(6) . . ? N1 Al1 H2 105.0(9) . . ? H1 Al1 H2 115.0(8) . . ? C3 N1 C5 109.49(19) 7_575 . ? C3 N1 C5 109.49(19) . 7_575 ? C3 N1 C1 109.53(19) . 7_575 ? C5 N1 C1 140.2(2) . 7_575 ? C5 N1 C1 105.19(17) 7_575 7_575 ? C3 N1 C1 109.53(19) 7_575 . ? C5 N1 C1 105.19(17) . . ? C5 N1 C1 140.2(2) 7_575 . ? C3 N1 Al1 112.52(13) 7_575 . ? C3 N1 Al1 112.52(13) . . ? C5 N1 Al1 110.61(15) . . ? C5 N1 Al1 110.61(15) 7_575 . ? C1 N1 Al1 109.23(13) 7_575 . ? C1 N1 Al1 109.23(13) . . ? N1 C1 C2 109.69(19) . . ? N1 C1 H1A 102.4(10) . . ? C2 C1 H1A 123.4(11) . . ? N1 C1 H1B 106(2) . . ? C2 C1 H1B 108(2) . . ? H1A C1 H1B 106(2) . . ? C1 C2 H2A 87.3(15) . . ? C1 C2 H2B 107.4(14) . . ? C1 C2 H2B 107.4(14) 7_575 . ? H2A C2 H2B 110.9(19) . . ? N1 C3 C4 114.7(9) . . ? N1 C3 H1A 101.1(10) . . ? C4 C3 H1A 116.0(14) . . ? N1 C3 H3B 103(2) . . ? C4 C3 H3B 115(3) . . ? H1A C3 H3B 105(3) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 N1 117.8(10) . . ? C6 C5 H5A 117.8(14) . . ? N1 C5 H5A 94.7(14) . . ? C6 C5 H5B 113(2) . . ? N1 C5 H5B 106(2) . . ? H5A C5 H5B 105(2) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.213 _refine_diff_density_min -0.137 _refine_diff_density_rms 0.034 data_sg081264 _database_code_depnum_ccdc_archive 'CCDC 916838' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C4 H11 Al O2' _chemical_formula_sum 'C4 H11 Al O2' _exptl_crystal_recrystallization_method ether _chemical_melting_point ? _exptl_crystal_description irregular _exptl_crystal_colour colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 118.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 6.318(3) _cell_length_b 8.570(4) _cell_length_c 6.811(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.450(6) _cell_angle_gamma 90.00 _cell_volume 333.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 1644 _cell_measurement_theta_min 3.57 _cell_measurement_theta_max 27.37 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.178 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 128 _exptl_absorpt_coefficient_mu 0.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8852 _exptl_absorpt_correction_T_max 0.9595 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2161 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_unetI/netI 0.0332 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 737 _reflns_number_gt 647 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0523P)^2^+0.0957P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 737 _refine_ls_number_parameters 62 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Al1 Al 0.0000 0.0000 0.0000 0.0266(3) Uani 1 2 d S . . O1 O 0.3067(2) -0.01437(13) 0.2937(2) 0.0303(3) Uani 1 1 d . . . C2 C 0.7193(3) 0.0351(2) 0.5075(3) 0.0346(4) Uani 1 1 d . . . C1 C 0.4940(3) 0.0949(2) 0.3302(3) 0.0354(4) Uani 1 1 d . . . H1A H 0.514(3) 0.103(2) 0.197(3) 0.043(5) Uiso 1 1 d . . . H1B H 0.444(4) 0.193(3) 0.366(3) 0.044(5) Uiso 1 1 d . . . H2A H 0.758(4) -0.064(3) 0.462(4) 0.050(6) Uiso 1 1 d . . . H2B H 0.839(4) 0.107(3) 0.539(3) 0.044(6) Uiso 1 1 d . . . H1 H -0.145(7) -0.070(5) 0.094(7) 0.049(12) Uiso 0.50 1 d P . . H2 H 0.032(8) 0.174(7) -0.004(7) 0.065(15) Uiso 0.50 1 d P . . H3 H -0.125(8) 0.101(5) 0.098(8) 0.057(13) 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 0.0213(4) 0.0300(4) 0.0226(4) -0.0004(2) 0.0039(3) 0.0005(2) O1 0.0211(6) 0.0426(7) 0.0202(6) 0.0016(4) 0.0023(4) -0.0053(4) C2 0.0211(7) 0.0519(10) 0.0264(8) 0.0052(7) 0.0061(6) -0.0051(7) C1 0.0249(8) 0.0475(11) 0.0267(7) 0.0083(6) 0.0045(6) -0.0069(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al1 O1 2.1071(14) 3 ? Al1 O1 2.1071(14) . ? Al1 H1 1.45(4) . ? Al1 H2 1.51(6) . ? Al1 H3 1.50(5) . ? O1 C2 1.444(2) 3_656 ? O1 C1 1.4440(19) . ? C2 O1 1.444(2) 3_656 ? C2 C1 1.506(2) . ? C2 H2A 0.97(2) . ? C2 H2B 0.93(2) . ? C1 H1A 0.97(2) . ? C1 H1B 0.96(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 O1 Al1 O1 180.0 3 . ? O1 Al1 H1 86.8(16) 3 . ? O1 Al1 H1 93.2(16) . . ? O1 Al1 H2 90.0(16) 3 . ? O1 Al1 H2 90.0(16) . . ? H1 Al1 H2 122(2) . . ? O1 Al1 H3 86.8(17) 3 . ? O1 Al1 H3 93.2(17) . . ? H1 Al1 H3 60(2) . . ? H2 Al1 H3 63(2) . . ? C2 O1 C1 109.48(13) 3_656 . ? C2 O1 Al1 117.95(10) 3_656 . ? C1 O1 Al1 118.48(9) . . ? O1 C2 C1 110.16(14) 3_656 . ? O1 C2 H2A 109.8(14) 3_656 . ? C1 C2 H2A 108.8(14) . . ? O1 C2 H2B 105.8(13) 3_656 . ? C1 C2 H2B 111.1(13) . . ? H2A C2 H2B 111.2(19) . . ? O1 C1 C2 109.86(14) . . ? O1 C1 H1A 108.2(12) . . ? C2 C1 H1A 108.3(12) . . ? O1 C1 H1B 106.0(12) . . ? C2 C1 H1B 113.0(12) . . ? H1A C1 H1B 111.5(17) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.298 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.063 data_sg081156 _database_code_depnum_ccdc_archive 'CCDC 916839' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H28.90 Al Cl0.10 N2' _chemical_formula_sum 'C18 H28.90 Al Cl0.10 N2' _exptl_crystal_recrystallization_method Pentane _chemical_melting_point ? _exptl_crystal_description Irregular _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 303.86 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' Al Al 0.0645 0.0514 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41 21 2' _symmetry_space_group_name_Hall 'P 4abw 2nw' _symmetry_int_tables_number 92 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+1/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+3/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-x+1/2, y+1/2, -z+1/4' '-y, -x, -z+1/2' _cell_length_a 6.7718(12) _cell_length_b 6.7718(12) _cell_length_c 40.619(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1862.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 5753 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.94 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.084 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 662 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9590 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12829 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0179 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_limit_l_max 52 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2121 _reflns_number_gt 1901 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0364P)^2^+0.4510P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; Flack H D (1983), Acta Cryst. A39, 876-881, 759 Friedel Pairs ; _refine_ls_abs_structure_Flack -0.1(2) _refine_ls_number_reflns 2121 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Al1 Al 0.23891(6) 0.23891(6) 0.0000 0.02845(15) Uani 1 2 d SD . . H1A H 0.210(3) 0.423(2) 0.0216(4) 0.045(5) Uiso 1 1 d D . . H1B H 0.077(2) 0.077(2) 0.0000 0.060(14) Uiso 0.90 2 d SPD . . Cl1 Cl 0.0289(6) 0.0289(6) 0.0000 0.0372(13) Uani 0.10 2 d SP . . N1 N 0.38999(18) 0.10024(17) 0.04142(3) 0.0275(3) Uani 1 1 d . . . C1 C 0.4200(2) -0.1139(2) 0.03424(3) 0.0296(3) Uani 1 1 d . . . H1C H 0.4800 -0.1259 0.0121 0.036 Uiso 1 1 calc R . . H1D H 0.2889 -0.1783 0.0334 0.036 Uiso 1 1 calc R . . C2 C 0.5475(2) -0.2267(2) 0.05836(3) 0.0285(3) Uani 1 1 d . . . C3 C 0.4687(2) -0.3121(2) 0.08664(4) 0.0333(3) Uani 1 1 d . . . H3 H 0.3320 -0.2972 0.0913 0.040 Uiso 1 1 calc R . . C4 C 0.5871(3) -0.4190(2) 0.10822(4) 0.0409(4) Uani 1 1 d . . . H4 H 0.5312 -0.4755 0.1275 0.049 Uiso 1 1 calc R . . C5 C 0.7852(3) -0.4432(2) 0.10168(4) 0.0440(4) Uani 1 1 d . . . H5 H 0.8662 -0.5157 0.1165 0.053 Uiso 1 1 calc R . . C6 C 0.8660(3) -0.3613(2) 0.07344(5) 0.0444(4) Uani 1 1 d . . . H6 H 1.0022 -0.3793 0.0687 0.053 Uiso 1 1 calc R . . C7 C 0.7480(2) -0.2531(2) 0.05217(4) 0.0360(3) Uani 1 1 d . . . H7 H 0.8050 -0.1959 0.0330 0.043 Uiso 1 1 calc R . . C15 C 0.2687(3) 0.1279(2) 0.07120(3) 0.0388(4) Uani 1 1 d . . . H15A H 0.3389 0.0743 0.0903 0.058 Uiso 1 1 calc R . . H15B H 0.1426 0.0586 0.0685 0.058 Uiso 1 1 calc R . . H15C H 0.2440 0.2690 0.0746 0.058 Uiso 1 1 calc R . . C16 C 0.5809(2) 0.2029(2) 0.04550(4) 0.0354(3) Uani 1 1 d . . . H16A H 0.5584 0.3457 0.0467 0.053 Uiso 1 1 calc R . . H16B H 0.6665 0.1731 0.0267 0.053 Uiso 1 1 calc R . . H16C H 0.6445 0.1581 0.0658 0.053 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 0.02902(19) 0.02902(19) 0.0273(3) 0.00166(16) -0.00166(16) 0.0053(3) Cl1 0.0301(16) 0.0301(16) 0.051(3) 0.0110(18) -0.0110(18) -0.008(2) N1 0.0323(6) 0.0246(6) 0.0256(5) -0.0021(5) -0.0038(5) 0.0030(5) C1 0.0360(8) 0.0257(7) 0.0272(6) -0.0018(6) -0.0062(6) 0.0025(6) C2 0.0367(7) 0.0206(7) 0.0281(6) -0.0035(5) -0.0072(6) 0.0019(6) C3 0.0403(8) 0.0277(7) 0.0321(7) -0.0002(6) -0.0031(6) 0.0012(6) C4 0.0644(11) 0.0299(8) 0.0283(7) 0.0023(6) -0.0067(8) 0.0023(7) C5 0.0566(11) 0.0297(8) 0.0458(9) -0.0023(7) -0.0271(9) 0.0080(7) C6 0.0347(9) 0.0339(9) 0.0645(11) -0.0031(8) -0.0126(8) 0.0045(6) C7 0.0367(7) 0.0297(7) 0.0415(8) 0.0008(6) -0.0008(6) 0.0008(7) C15 0.0501(10) 0.0397(8) 0.0268(7) 0.0003(6) 0.0017(7) 0.0121(8) C16 0.0385(8) 0.0275(7) 0.0403(8) -0.0001(6) -0.0130(7) -0.0005(6) _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 Cl1 2.012(6) . ? Al1 N1 2.1814(11) . ? Al1 N1 2.1814(11) 6 ? Al1 H1A 1.537(16) . ? Al1 H1B 1.55(2) . ? N1 C15 1.4743(19) . ? N1 C16 1.4775(19) . ? N1 C1 1.4929(18) . ? C1 C2 1.5128(19) . ? C1 H1C 0.9900 . ? C1 H1D 0.9900 . ? C2 C7 1.392(2) . ? C2 C3 1.393(2) . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 C7 1.386(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 Cl1 Al1 N1 91.56(4) . . ? Cl1 Al1 N1 91.56(4) . 6 ? N1 Al1 N1 176.88(7) . 6 ? Cl1 Al1 H1A 119.0(7) . . ? N1 Al1 H1A 88.2(6) . . ? N1 Al1 H1A 90.3(6) 6 . ? N1 Al1 H1B 91.56(4) . . ? N1 Al1 H1B 91.56(4) 6 . ? H1A Al1 H1B 119.0(7) . . ? C15 N1 C16 109.62(12) . . ? C15 N1 C1 111.06(12) . . ? C16 N1 C1 111.09(11) . . ? C15 N1 Al1 108.48(9) . . ? C16 N1 Al1 107.12(9) . . ? C1 N1 Al1 109.36(8) . . ? N1 C1 C2 116.21(11) . . ? N1 C1 H1C 108.2 . . ? C2 C1 H1C 108.2 . . ? N1 C1 H1D 108.2 . . ? C2 C1 H1D 108.2 . . ? H1C C1 H1D 107.4 . . ? C7 C2 C3 118.00(14) . . ? C7 C2 C1 120.28(13) . . ? C3 C2 C1 121.69(13) . . ? C4 C3 C2 121.01(15) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 120.11(16) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.76(15) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 119.97(16) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C2 121.15(15) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.197 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.033 data_sg081159 _database_code_depnum_ccdc_archive 'CCDC 916840' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C6 H19 Al N2' _chemical_formula_sum 'C6 H19 Al N2' _exptl_crystal_recrystallization_method THF _chemical_melting_point ? _exptl_crystal_description Plate _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 146.21 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 9.3788(18) _cell_length_b 10.114(2) _cell_length_c 11.122(2) _cell_angle_alpha 90.00 _cell_angle_beta 111.542(2) _cell_angle_gamma 90.00 _cell_volume 981.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 2330 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.28 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.990 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.142 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9195 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6524 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2186 _reflns_number_gt 1618 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008)' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008)' _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^)+(0.0332P)^2^+0.4408P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2186 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.0829 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _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 0.28693(5) 0.62152(5) 0.22368(4) 0.02725(16) Uani 1 1 d . . . N1 N 0.28478(15) 0.40396(14) 0.23161(13) 0.0292(3) Uani 1 1 d . . . N2 N 0.70986(15) 0.33600(14) 0.30069(12) 0.0275(3) Uani 1 1 d . . . C1 C 0.4216(2) 0.34227(19) 0.21717(17) 0.0330(4) Uani 1 1 d . . . C2 C 0.57092(19) 0.38409(19) 0.32254(16) 0.0311(4) Uani 1 1 d . . . C3 C 0.2657(2) 0.3597(2) 0.3514(2) 0.0408(5) Uani 1 1 d . . . C4 C 0.1497(2) 0.3592(2) 0.1197(2) 0.0449(5) Uani 1 1 d . . . C5 C 0.7275(3) 0.4028(2) 0.1895(2) 0.0422(5) Uani 1 1 d . . . C6 C 0.8423(2) 0.3712(2) 0.41839(19) 0.0399(4) Uani 1 1 d . . . H1 H 0.402(2) 0.6320(17) 0.3647(18) 0.040(5) Uiso 1 1 d . . . H2 H 0.339(2) 0.6063(18) 0.1086(18) 0.047(6) Uiso 1 1 d . . . H3 H 0.117(2) 0.6256(18) 0.2069(19) 0.047(6) Uiso 1 1 d . . . H1A H 0.412(2) 0.246(2) 0.2188(17) 0.039(5) Uiso 1 1 d . . . H2A H 0.575(2) 0.3495(19) 0.405(2) 0.044(5) Uiso 1 1 d . . . H3A H 0.256(2) 0.266(2) 0.352(2) 0.055(6) Uiso 1 1 d . . . H4A H 0.146(2) 0.261(2) 0.119(2) 0.053(6) Uiso 1 1 d . . . H5A H 0.643(3) 0.382(2) 0.109(2) 0.049(6) Uiso 1 1 d . . . H6A H 0.938(3) 0.343(2) 0.4068(19) 0.047(6) Uiso 1 1 d . . . H1B H 0.420(2) 0.3697(17) 0.1301(18) 0.033(5) Uiso 1 1 d . . . H2B H 0.575(2) 0.480(2) 0.3284(17) 0.035(5) Uiso 1 1 d . . . H3B H 0.354(2) 0.391(2) 0.429(2) 0.046(6) Uiso 1 1 d . . . H4B H 0.054(3) 0.395(2) 0.127(2) 0.052(6) Uiso 1 1 d . . . H5B H 0.821(2) 0.3754(18) 0.1873(17) 0.034(5) Uiso 1 1 d . . . H6B H 0.844(2) 0.469(2) 0.4323(19) 0.048(6) Uiso 1 1 d . . . H3C H 0.174(2) 0.3978(19) 0.3531(19) 0.043(6) Uiso 1 1 d . . . H4C H 0.159(2) 0.387(2) 0.044(2) 0.046(6) Uiso 1 1 d . . . H5C H 0.733(3) 0.500(3) 0.201(2) 0.064(7) Uiso 1 1 d . . . H6C H 0.833(2) 0.328(2) 0.4905(19) 0.041(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Al1 0.0239(3) 0.0325(3) 0.0243(2) -0.0001(2) 0.00776(19) 0.0001(2) N1 0.0209(7) 0.0336(8) 0.0309(7) -0.0029(6) 0.0067(6) -0.0024(6) N2 0.0224(7) 0.0315(8) 0.0271(7) -0.0017(6) 0.0073(5) -0.0021(6) C1 0.0280(9) 0.0356(10) 0.0333(9) -0.0055(8) 0.0087(7) 0.0005(8) C2 0.0265(8) 0.0363(10) 0.0291(8) -0.0049(8) 0.0084(7) 0.0002(8) C3 0.0401(11) 0.0393(12) 0.0488(11) 0.0037(9) 0.0232(9) -0.0043(9) C4 0.0294(10) 0.0455(13) 0.0490(12) -0.0123(10) 0.0016(9) -0.0049(9) C5 0.0470(12) 0.0427(13) 0.0429(11) 0.0061(9) 0.0237(10) -0.0042(10) C6 0.0283(9) 0.0453(12) 0.0391(10) -0.0092(9) 0.0042(8) -0.0046(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 Al1 N2 2.1878(16) 2_655 ? Al1 N1 2.2027(16) . ? Al1 H1 1.546(18) . ? Al1 H2 1.537(19) . ? Al1 H3 1.54(2) . ? N1 C3 1.478(2) . ? N1 C4 1.483(2) . ? N1 C1 1.488(2) . ? N2 C5 1.471(2) . ? N2 C6 1.479(2) . ? N2 C2 1.492(2) . ? N2 Al1 2.1878(16) 2_645 ? C1 C2 1.519(2) . ? C1 H1A 0.97(2) . ? C1 H1B 1.003(18) . ? C2 H2A 0.97(2) . ? C2 H2B 0.98(2) . ? C3 H3A 0.95(2) . ? C3 H3B 1.00(2) . ? C3 H3C 0.95(2) . ? C4 H4A 0.99(2) . ? C4 H4B 1.00(2) . ? C4 H4C 0.92(2) . ? C5 H5A 0.98(2) . ? C5 H5B 0.93(2) . ? C5 H5C 0.99(3) . ? C6 H6A 0.99(2) . ? C6 H6B 1.00(2) . ? C6 H6C 0.94(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 Al1 N1 175.07(6) 2_655 . ? N2 Al1 H1 91.2(7) 2_655 . ? N1 Al1 H1 92.4(7) . . ? N2 Al1 H2 88.5(7) 2_655 . ? N1 Al1 H2 86.8(7) . . ? H1 Al1 H2 122.4(10) . . ? N2 Al1 H3 91.1(7) 2_655 . ? N1 Al1 H3 90.4(7) . . ? H1 Al1 H3 115.3(10) . . ? H2 Al1 H3 122.3(10) . . ? C3 N1 C4 108.39(16) . . ? C3 N1 C1 111.41(15) . . ? C4 N1 C1 106.65(14) . . ? C3 N1 Al1 110.16(12) . . ? C4 N1 Al1 106.77(12) . . ? C1 N1 Al1 113.18(11) . . ? C5 N2 C6 108.46(15) . . ? C5 N2 C2 111.20(15) . . ? C6 N2 C2 106.08(13) . . ? C5 N2 Al1 109.89(12) . 2_645 ? C6 N2 Al1 107.64(12) . 2_645 ? C2 N2 Al1 113.33(10) . 2_645 ? N1 C1 C2 112.78(14) . . ? N1 C1 H1A 108.8(11) . . ? C2 C1 H1A 109.3(11) . . ? N1 C1 H1B 106.5(10) . . ? C2 C1 H1B 110.4(10) . . ? H1A C1 H1B 109.0(15) . . ? N2 C2 C1 113.35(14) . . ? N2 C2 H2A 107.7(12) . . ? C1 C2 H2A 109.5(12) . . ? N2 C2 H2B 109.0(11) . . ? C1 C2 H2B 109.2(11) . . ? H2A C2 H2B 108.0(15) . . ? N1 C3 H3A 110.7(13) . . ? N1 C3 H3B 110.2(11) . . ? H3A C3 H3B 110.7(17) . . ? N1 C3 H3C 107.8(12) . . ? H3A C3 H3C 108.4(17) . . ? H3B C3 H3C 109.0(17) . . ? N1 C4 H4A 109.1(13) . . ? N1 C4 H4B 109.8(12) . . ? H4A C4 H4B 109.6(17) . . ? N1 C4 H4C 109.8(13) . . ? H4A C4 H4C 108.0(17) . . ? H4B C4 H4C 110.6(18) . . ? N2 C5 H5A 111.3(12) . . ? N2 C5 H5B 106.5(11) . . ? H5A C5 H5B 111.7(17) . . ? N2 C5 H5C 111.3(13) . . ? H5A C5 H5C 108.8(18) . . ? H5B C5 H5C 107.1(17) . . ? N2 C6 H6A 108.7(12) . . ? N2 C6 H6B 109.5(12) . . ? H6A C6 H6B 110.1(16) . . ? N2 C6 H6C 109.5(12) . . ? H6A C6 H6C 110.3(17) . . ? H6B C6 H6C 108.8(17) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.326 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.045 data_sg090908 _database_code_depnum_ccdc_archive 'CCDC 916841' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C7 H21 Al N2' _chemical_formula_sum 'C7 H21 Al N2' _exptl_crystal_recrystallization_method THF _chemical_melting_point ? _exptl_crystal_description Plate _exptl_crystal_colour Colourless _diffrn_ambient_temperature 173(1) _chemical_formula_weight 160.24 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_int_tables_number 61 _chemical_absolute_configuration ? 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 12.1703(16) _cell_length_b 12.4077(16) _cell_length_c 14.2504(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2151.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 7076 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 28.39 _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.989 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9177 _exptl_absorpt_correction_T_max 0.9801 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART1000/P4' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11653 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_unetI/netI 0.0315 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2409 _reflns_number_gt 1997 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Sheldrick, 2008' _computing_publication_material 'Bruker SHELXTL (Sheldrick, 2008' _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^)+(0.0553P)^2^+0.4779P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2409 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.1059 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 0.14237(3) 0.13806(3) 0.62213(2) 0.02527(14) Uani 1 1 d . . . N1 N 0.22291(9) 0.04914(8) 0.73672(7) 0.0256(2) Uani 1 1 d . . . N2 N 0.06786(9) 0.26948(8) 1.00768(7) 0.0260(2) Uani 1 1 d . . . C1 C 0.23634(10) 0.11380(11) 0.82376(9) 0.0277(3) Uani 1 1 d . . . C2 C 0.12981(11) 0.15347(12) 0.86779(9) 0.0312(3) Uani 1 1 d . . . C3 C 0.15936(10) 0.22133(10) 0.95344(9) 0.0276(3) Uani 1 1 d . . . C4 C 0.16322(13) -0.05184(11) 0.75655(11) 0.0345(3) Uani 1 1 d . . . C5 C 0.33431(12) 0.02126(14) 0.70350(11) 0.0390(3) Uani 1 1 d . . . C6 C -0.00420(12) 0.18604(12) 1.04824(10) 0.0348(3) Uani 1 1 d . . . C7 C 0.00088(14) 0.34284(13) 0.94961(10) 0.0383(3) Uani 1 1 d . . . H1 H 0.0262(13) 0.1181(13) 0.6612(11) 0.038(4) Uiso 1 1 d . . . H2 H 0.1926(14) 0.0597(13) 0.5502(12) 0.048(5) Uiso 1 1 d . . . H3 H 0.2080(13) 0.2400(14) 0.6529(11) 0.045(4) Uiso 1 1 d . . . H1A H 0.2753(14) 0.0727(13) 0.8682(11) 0.038(4) Uiso 1 1 d . . . H1B H 0.2794(13) 0.1758(12) 0.8057(11) 0.034(4) Uiso 1 1 d . . . H2A H 0.0797(14) 0.0934(15) 0.8851(11) 0.043(4) Uiso 1 1 d . . . H2B H 0.0896(14) 0.1930(13) 0.8243(12) 0.043(5) Uiso 1 1 d . . . H3A H 0.2010(13) 0.1761(12) 0.9964(10) 0.030(4) Uiso 1 1 d . . . H3B H 0.2044(13) 0.2826(13) 0.9339(11) 0.036(4) Uiso 1 1 d . . . H4A H 0.1664(14) -0.0976(15) 0.7004(13) 0.049(5) Uiso 1 1 d . . . H4B H 0.0874(13) -0.0376(12) 0.7723(10) 0.031(4) Uiso 1 1 d . . . H4C H 0.1981(14) -0.0901(14) 0.8086(12) 0.047(5) Uiso 1 1 d . . . H5A H 0.3284(14) -0.0200(15) 0.6471(13) 0.048(5) Uiso 1 1 d . . . H5B H 0.3720(14) 0.0836(15) 0.6877(12) 0.043(5) Uiso 1 1 d . . . H5C H 0.3739(15) -0.0131(17) 0.7506(12) 0.047(5) Uiso 1 1 d . . . H6A H -0.0563(14) 0.2181(14) 1.0912(12) 0.047(5) Uiso 1 1 d . . . H6B H 0.0392(16) 0.1384(15) 1.0850(14) 0.055(5) Uiso 1 1 d . . . H6C H -0.0433(14) 0.1451(13) 0.9995(12) 0.043(4) Uiso 1 1 d . . . H7A H 0.0488(15) 0.3950(15) 0.9220(13) 0.054(5) Uiso 1 1 d . . . H7B H -0.0402(14) 0.3054(14) 0.9016(12) 0.044(4) Uiso 1 1 d . . . H7C H -0.0511(13) 0.3779(13) 0.9888(12) 0.040(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Al1 0.0274(2) 0.0265(2) 0.0219(2) -0.00151(13) 0.00122(14) -0.00512(13) N1 0.0242(5) 0.0264(5) 0.0263(5) -0.0050(4) 0.0003(4) -0.0004(4) N2 0.0266(5) 0.0283(5) 0.0230(5) 0.0024(4) 0.0003(4) 0.0056(4) C1 0.0263(6) 0.0331(6) 0.0237(6) -0.0054(5) -0.0026(5) 0.0003(5) C2 0.0289(7) 0.0389(7) 0.0259(7) -0.0064(5) -0.0008(5) 0.0020(5) C3 0.0265(6) 0.0327(7) 0.0236(6) -0.0033(5) 0.0009(5) 0.0016(5) C4 0.0402(8) 0.0247(6) 0.0386(8) 0.0004(6) -0.0046(6) -0.0016(5) C5 0.0271(7) 0.0523(9) 0.0375(8) -0.0137(7) -0.0008(6) 0.0074(6) C6 0.0329(7) 0.0373(7) 0.0343(7) 0.0008(6) 0.0049(6) -0.0017(6) C7 0.0440(8) 0.0378(8) 0.0333(7) 0.0006(6) -0.0096(7) 0.0136(6) _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 N2 2.1906(11) 7_565 ? Al1 N1 2.2010(11) . ? Al1 H1 1.539(16) . ? Al1 H2 1.539(17) . ? Al1 H3 1.559(17) . ? N1 C4 1.4756(16) . ? N1 C5 1.4771(17) . ? N1 C1 1.4863(15) . ? N2 C6 1.4748(17) . ? N2 C7 1.4757(16) . ? N2 C3 1.4814(15) . ? N2 Al1 2.1906(11) 7_566 ? C1 C2 1.5222(18) . ? C1 H1A 0.941(17) . ? C1 H1B 0.965(16) . ? C2 C3 1.5257(17) . ? C2 H2A 0.995(18) . ? C2 H2B 0.930(17) . ? C3 H3A 0.973(15) . ? C3 H3B 0.978(16) . ? C4 H4A 0.982(19) . ? C4 H4B 0.966(16) . ? C4 H4C 0.978(18) . ? C5 H5A 0.956(18) . ? C5 H5B 0.927(19) . ? C5 H5C 0.930(18) . ? C6 H6A 0.967(18) . ? C6 H6B 0.950(19) . ? C6 H6C 0.983(17) . ? C7 H7A 0.96(2) . ? C7 H7B 0.966(18) . ? C7 H7C 0.950(17) . ? 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 Al1 N1 177.78(4) 7_565 . ? N2 Al1 H1 88.5(6) 7_565 . ? N1 Al1 H1 93.4(6) . . ? N2 Al1 H2 89.9(6) 7_565 . ? N1 Al1 H2 90.1(6) . . ? H1 Al1 H2 120.3(9) . . ? N2 Al1 H3 89.8(6) 7_565 . ? N1 Al1 H3 88.3(6) . . ? H1 Al1 H3 119.9(8) . . ? H2 Al1 H3 119.8(9) . . ? C4 N1 C5 108.33(11) . . ? C4 N1 C1 110.65(10) . . ? C5 N1 C1 107.03(10) . . ? C4 N1 Al1 110.39(8) . . ? C5 N1 Al1 106.76(9) . . ? C1 N1 Al1 113.43(8) . . ? C6 N2 C7 108.92(12) . . ? C6 N2 C3 111.62(10) . . ? C7 N2 C3 111.80(10) . . ? C6 N2 Al1 108.78(8) . 7_566 ? C7 N2 Al1 108.85(8) . 7_566 ? C3 N2 Al1 106.77(7) . 7_566 ? N1 C1 C2 115.14(10) . . ? N1 C1 H1A 108.9(10) . . ? C2 C1 H1A 109.1(10) . . ? N1 C1 H1B 105.5(9) . . ? C2 C1 H1B 108.3(9) . . ? H1A C1 H1B 109.7(14) . . ? C1 C2 C3 107.91(11) . . ? C1 C2 H2A 112.5(10) . . ? C3 C2 H2A 111.1(9) . . ? C1 C2 H2B 110.1(10) . . ? C3 C2 H2B 111.5(10) . . ? H2A C2 H2B 103.8(14) . . ? N2 C3 C2 117.57(11) . . ? N2 C3 H3A 107.2(9) . . ? C2 C3 H3A 107.9(9) . . ? N2 C3 H3B 104.9(9) . . ? C2 C3 H3B 109.5(9) . . ? H3A C3 H3B 109.6(13) . . ? N1 C4 H4A 108.4(11) . . ? N1 C4 H4B 111.0(9) . . ? H4A C4 H4B 109.4(13) . . ? N1 C4 H4C 110.1(10) . . ? H4A C4 H4C 108.7(14) . . ? H4B C4 H4C 109.1(13) . . ? N1 C5 H5A 109.0(10) . . ? N1 C5 H5B 109.7(11) . . ? H5A C5 H5B 106.2(15) . . ? N1 C5 H5C 110.6(11) . . ? H5A C5 H5C 113.6(16) . . ? H5B C5 H5C 107.5(16) . . ? N2 C6 H6A 110.4(10) . . ? N2 C6 H6B 108.8(11) . . ? H6A C6 H6B 105.7(15) . . ? N2 C6 H6C 112.0(10) . . ? H6A C6 H6C 110.0(14) . . ? H6B C6 H6C 109.7(15) . . ? N2 C7 H7A 108.1(11) . . ? N2 C7 H7B 112.7(10) . . ? H7A C7 H7B 110.5(15) . . ? N2 C7 H7C 108.7(10) . . ? H7A C7 H7C 109.8(15) . . ? H7B C7 H7C 107.0(14) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.298 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.043