# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Cameron Jones' 'Richard P. Rose' _publ_contact_author_name 'Cameron Jones' _publ_contact_author_address ; School of Chemistry Monash University PO Box 23 Clayton Victoria 3800 AUSTRALIA ; _publ_contact_author_email CAMERON.JONES@SCI.MONASH.EDU.AU _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Synthesis and Characterisation of Tetramethylpiperidinyloxide (TEMPO) Complexes of Group 13 Metal Hydrides ; data_compound1 _database_code_depnum_ccdc_archive 'CCDC 645534' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H33 Al N2 O' _chemical_formula_weight 296.42 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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.3500(13) _cell_length_b 10.747(2) _cell_length_c 13.239(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.69(3) _cell_angle_gamma 90.00 _cell_volume 902.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.091 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6069 _diffrn_reflns_av_R_equivalents 0.0913 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1674 _reflns_number_gt 1127 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The hydride ligand was located from difference maps and refine isotropically. ; _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^)+(0.0680P)^2^+0.5442P] 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 1674 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1679 _refine_ls_wR_factor_gt 0.1507 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.0110(2) 0.2500 0.61435(9) 0.0336(4) Uani 1 2 d S . . O1 O 0.2313(4) 0.2500 0.69939(17) 0.0306(7) Uani 1 2 d S . . N1 N 0.1836(5) 0.2500 0.4916(2) 0.0235(8) Uani 1 2 d S . . N2 N 0.1768(5) 0.2500 0.8050(2) 0.0295(8) Uani 1 2 d S . . C1 C 0.0485(7) 0.2500 0.3966(3) 0.0462(13) Uani 1 2 d S . . H1A H -0.0433 0.3245 0.3954 0.055 Uiso 0.50 1 calc PR . . H1B H -0.0433 0.1755 0.3954 0.055 Uiso 0.50 1 calc PR . . C2 C 0.1789(7) 0.2500 0.3029(3) 0.0357(11) Uani 1 2 d S . . H2A H 0.1449 0.1754 0.2615 0.043 Uiso 0.50 1 calc PR . . H2B H 0.1449 0.3246 0.2615 0.043 Uiso 0.50 1 calc PR . . C3 C 0.4122(7) 0.2500 0.3348(3) 0.0315(10) Uani 1 2 d S . . H3 H 0.5005 0.2500 0.2742 0.038 Uiso 1 2 calc SR . . C4 C 0.3206(5) 0.1378(3) 0.4915(2) 0.0365(8) Uani 1 1 d . . . H4A H 0.2313 0.0623 0.4918 0.044 Uiso 1 1 calc R . . H4B H 0.4130 0.1371 0.5538 0.044 Uiso 1 1 calc R . . C5 C 0.4570(5) 0.1345(3) 0.3992(2) 0.0360(8) Uani 1 1 d . . . H5A H 0.6080 0.1322 0.4215 0.043 Uiso 1 1 calc R . . H5B H 0.4247 0.0587 0.3589 0.043 Uiso 1 1 calc R . . C6 C 0.2608(5) 0.1312(3) 0.8500(2) 0.0360(8) Uani 1 1 d . . . C7 C 0.2164(6) 0.1355(4) 0.9628(2) 0.0557(10) Uani 1 1 d . . . H7A H 0.0621 0.1334 0.9703 0.067 Uiso 1 1 calc R . . H7B H 0.2774 0.0605 0.9962 0.067 Uiso 1 1 calc R . . C8 C 0.3061(10) 0.2500 1.0155(3) 0.0654(17) Uani 1 2 d S . . H8A H 0.4617 0.2500 1.0133 0.078 Uiso 1 2 calc SR . . H8B H 0.2685 0.2500 1.0873 0.078 Uiso 1 2 calc SR . . C9 C 0.1287(6) 0.0264(3) 0.8017(3) 0.0536(10) Uani 1 1 d . . . H9A H -0.0214 0.0455 0.8069 0.080 Uiso 1 1 calc R . . H9B H 0.1616 -0.0519 0.8370 0.080 Uiso 1 1 calc R . . H9C H 0.1609 0.0184 0.7304 0.080 Uiso 1 1 calc R . . C10 C 0.4929(5) 0.1041(3) 0.8343(2) 0.0464(9) Uani 1 1 d . . . H10A H 0.5258 0.1256 0.7649 0.070 Uiso 1 1 calc R . . H10B H 0.5210 0.0156 0.8462 0.070 Uiso 1 1 calc R . . H10C H 0.5808 0.1539 0.8818 0.070 Uiso 1 1 calc R . . H1 H -0.121(5) 0.125(3) 0.603(2) 0.052(9) 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 0.0304(8) 0.0466(8) 0.0236(6) 0.000 0.0017(5) 0.000 O1 0.0375(18) 0.0397(17) 0.0144(13) 0.000 0.0004(12) 0.000 N1 0.0236(19) 0.0254(18) 0.0212(16) 0.000 -0.0028(14) 0.000 N2 0.041(2) 0.0277(19) 0.0203(17) 0.000 0.0030(15) 0.000 C1 0.026(3) 0.089(4) 0.023(2) 0.000 -0.0054(19) 0.000 C2 0.038(3) 0.047(3) 0.022(2) 0.000 0.0023(19) 0.000 C3 0.034(3) 0.034(2) 0.027(2) 0.000 0.0115(18) 0.000 C4 0.050(2) 0.0213(16) 0.0387(17) 0.0023(13) 0.0084(15) 0.0051(14) C5 0.0372(19) 0.0316(17) 0.0400(18) -0.0018(13) 0.0094(14) 0.0026(14) C6 0.045(2) 0.0337(18) 0.0288(16) 0.0089(13) -0.0022(14) 0.0015(15) C7 0.067(3) 0.067(3) 0.0335(18) 0.0188(17) 0.0044(17) -0.003(2) C8 0.085(4) 0.095(5) 0.017(2) 0.000 0.007(2) 0.000 C9 0.064(3) 0.036(2) 0.060(2) 0.0125(16) -0.0094(19) -0.0063(18) C10 0.050(2) 0.046(2) 0.0421(19) 0.0018(15) -0.0080(16) 0.0139(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al1 O1 1.754(3) . ? Al1 N1 2.003(3) . ? Al1 H1 1.59(3) . ? O1 N2 1.456(4) . ? N1 C4 1.487(3) . ? N1 C4 1.487(3) 4_565 ? N1 C1 1.488(4) . ? N2 C6 1.497(3) 4_565 ? N2 C6 1.497(3) . ? C1 C2 1.524(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.521(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.525(4) . ? C3 C5 1.525(4) 4_565 ? C3 H3 1.0000 . ? C4 C5 1.531(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C10 1.526(4) . ? C6 C9 1.527(4) . ? C6 C7 1.533(4) . ? C7 C8 1.513(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C7 1.513(4) 4_565 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 O1 Al1 N1 94.04(13) . . ? O1 Al1 H1 117.7(10) . . ? N1 Al1 H1 103.2(11) . . ? N2 O1 Al1 113.4(2) . . ? C4 N1 C4 108.4(3) . 4_565 ? C4 N1 C1 108.3(2) . . ? C4 N1 C1 108.3(2) 4_565 . ? C4 N1 Al1 110.06(17) . . ? C4 N1 Al1 110.06(17) 4_565 . ? C1 N1 Al1 111.7(2) . . ? O1 N2 C6 106.64(19) . 4_565 ? O1 N2 C6 106.64(19) . . ? C6 N2 C6 117.1(3) 4_565 . ? N1 C1 C2 112.0(3) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C1 109.5(3) . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C5 108.0(2) . . ? C2 C3 C5 108.0(2) . 4_565 ? C5 C3 C5 109.0(3) . 4_565 ? C2 C3 H3 110.6 . . ? C5 C3 H3 110.6 . . ? C5 C3 H3 110.6 4_565 . ? N1 C4 C5 111.9(2) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C3 C5 C4 109.2(3) . . ? C3 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? C3 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? N2 C6 C10 115.9(3) . . ? N2 C6 C9 106.5(2) . . ? C10 C6 C9 108.5(3) . . ? N2 C6 C7 106.5(3) . . ? C10 C6 C7 111.2(3) . . ? C9 C6 C7 107.9(3) . . ? C8 C7 C6 113.1(3) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C7 108.8(4) . 4_565 ? C7 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 4_565 . ? C7 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 4_565 . ? H8A C8 H8B 108.3 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.414 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.060 # Attachment 'cmpd2.CIF' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 645535' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H33 Ga N2 O' _chemical_formula_weight 339.16 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' Ga Ga 0.2307 1.6083 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 6.3500(13) _cell_length_b 10.729(2) _cell_length_c 13.273(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.61(3) _cell_angle_gamma 90.00 _cell_volume 903.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 1.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.787 _exptl_absorpt_correction_T_max 0.862 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4659 _diffrn_reflns_av_R_equivalents 0.1353 _diffrn_reflns_av_sigmaI/netI 0.0968 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1672 _reflns_number_gt 1492 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The hydride ligand was located from difference maps and refined isotropically. The largest residual electron density peak in the final difference map (2.488 e/ang.3) was found close to Ga(1). ; _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^)+(0.1289P)^2^+1.7128P] 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 1672 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0962 _refine_ls_R_factor_gt 0.0897 _refine_ls_wR_factor_ref 0.2302 _refine_ls_wR_factor_gt 0.2239 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _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 Ga1 Ga -0.00665(13) 0.2500 0.61429(6) 0.0328(5) Uani 1 2 d S . . O1 O 0.2316(9) 0.2500 0.6999(4) 0.0302(12) Uani 1 2 d S . . N1 N 0.1785(10) 0.2500 0.4892(5) 0.0260(14) Uani 1 2 d S . . N2 N 0.1820(10) 0.2500 0.8053(5) 0.0282(14) Uani 1 2 d S . . C1 C 0.0475(12) 0.2500 0.3921(6) 0.044(3) Uani 1 2 d S . . H1A H -0.0444 0.3246 0.3899 0.053 Uiso 0.50 1 calc PR . . H1B H -0.0444 0.1754 0.3899 0.053 Uiso 0.50 1 calc PR . . C2 C 0.1805(14) 0.2500 0.3013(6) 0.038(2) Uani 1 2 d S . . H2A H 0.1488 0.3248 0.2597 0.046 Uiso 0.50 1 calc PR . . H2B H 0.1488 0.1752 0.2597 0.046 Uiso 0.50 1 calc PR . . C3 C 0.4148(13) 0.2500 0.3370(6) 0.0321(18) Uani 1 2 d S . . H3 H 0.5069 0.2500 0.2779 0.038 Uiso 1 2 calc SR . . C4 C 0.3122(10) 0.1379(5) 0.4919(5) 0.0353(14) Uani 1 1 d . . . H4A H 0.2217 0.0627 0.4908 0.042 Uiso 1 1 calc R . . H4B H 0.4002 0.1370 0.5554 0.042 Uiso 1 1 calc R . . C5 C 0.4559(9) 0.1340(6) 0.4016(5) 0.0353(13) Uani 1 1 d . . . H5A H 0.6055 0.1317 0.4260 0.042 Uiso 1 1 calc R . . H5B H 0.4261 0.0581 0.3610 0.042 Uiso 1 1 calc R . . C6 C 0.2619(9) 0.1312(5) 0.8498(4) 0.0352(14) Uani 1 1 d . . . C7 C 0.2218(12) 0.1349(8) 0.9629(5) 0.0554(19) Uani 1 1 d . . . H7A H 0.0680 0.1313 0.9718 0.066 Uiso 1 1 calc R . . H7B H 0.2860 0.0602 0.9956 0.066 Uiso 1 1 calc R . . C8 C 0.310(2) 0.2500 1.0150(7) 0.073(4) Uani 1 2 d S . . H8A H 0.4657 0.2500 1.0130 0.087 Uiso 1 2 calc SR . . H8B H 0.2722 0.2500 1.0865 0.087 Uiso 1 2 calc SR . . C9 C 0.1311(12) 0.0266(6) 0.8024(6) 0.0525(18) Uani 1 1 d . . . H9A H -0.0189 0.0449 0.8085 0.079 Uiso 1 1 calc R . . H9B H 0.1661 -0.0519 0.8371 0.079 Uiso 1 1 calc R . . H9C H 0.1617 0.0190 0.7309 0.079 Uiso 1 1 calc R . . C10 C 0.4942(11) 0.1045(7) 0.8326(5) 0.0492(17) Uani 1 1 d . . . H10A H 0.5237 0.1221 0.7622 0.074 Uiso 1 1 calc R . . H10B H 0.5248 0.0167 0.8476 0.074 Uiso 1 1 calc R . . H10C H 0.5829 0.1576 0.8772 0.074 Uiso 1 1 calc R . . H1 H -0.121(9) 0.135(5) 0.604(4) 0.026(14) 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 Ga1 0.0325(6) 0.0465(7) 0.0188(6) 0.000 -0.0075(4) 0.000 O1 0.043(3) 0.041(3) 0.006(2) 0.000 -0.003(2) 0.000 N1 0.034(3) 0.024(3) 0.019(3) 0.000 -0.007(3) 0.000 N2 0.032(3) 0.032(3) 0.020(3) 0.000 -0.002(3) 0.000 C1 0.016(4) 0.096(8) 0.020(4) 0.000 -0.013(3) 0.000 C2 0.039(5) 0.053(5) 0.023(4) 0.000 0.003(3) 0.000 C3 0.035(4) 0.032(4) 0.029(4) 0.000 0.002(3) 0.000 C4 0.054(4) 0.022(3) 0.029(3) 0.005(2) -0.001(3) 0.006(2) C5 0.034(3) 0.033(3) 0.039(3) 0.000(3) 0.000(2) 0.007(2) C6 0.040(3) 0.036(3) 0.029(3) 0.007(2) -0.013(2) 0.002(2) C7 0.064(5) 0.072(5) 0.030(3) 0.021(3) -0.004(3) -0.001(4) C8 0.097(9) 0.110(10) 0.010(4) 0.000 -0.001(5) 0.000 C9 0.067(5) 0.031(3) 0.058(5) 0.009(3) -0.018(4) -0.006(3) C10 0.058(4) 0.048(4) 0.040(4) -0.004(3) -0.015(3) 0.008(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 O1 1.850(5) . ? Ga1 N1 2.078(7) . ? Ga1 H1 1.43(6) . ? O1 N2 1.447(8) . ? N1 C4 1.472(7) 4_565 ? N1 C4 1.472(7) . ? N1 C1 1.501(9) . ? N2 C6 1.484(6) 4_565 ? N2 C6 1.484(6) . ? C1 C2 1.503(11) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.540(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.528(8) . ? C3 C5 1.528(8) 4_565 ? C3 H3 1.0000 . ? C4 C5 1.539(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C9 1.516(9) . ? C6 C10 1.530(9) . ? C6 C7 1.535(9) . ? C7 C8 1.511(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C7 1.511(11) 4_565 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 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 O1 Ga1 N1 90.8(2) . . ? O1 Ga1 H1 117(2) . . ? N1 Ga1 H1 103(2) . . ? N2 O1 Ga1 112.7(4) . . ? C4 N1 C4 109.6(6) 4_565 . ? C4 N1 C1 108.5(4) 4_565 . ? C4 N1 C1 108.5(4) . . ? C4 N1 Ga1 109.1(3) 4_565 . ? C4 N1 Ga1 109.1(3) . . ? C1 N1 Ga1 112.0(5) . . ? O1 N2 C6 107.4(4) . 4_565 ? O1 N2 C6 107.4(4) . . ? C6 N2 C6 118.3(6) 4_565 . ? N1 C1 C2 112.2(6) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C1 C2 C3 108.9(7) . . ? C1 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2B 109.9 . . ? C3 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C5 C3 C5 109.2(7) . 4_565 ? C5 C3 C2 108.1(4) . . ? C5 C3 C2 108.1(4) 4_565 . ? C5 C3 H3 110.5 . . ? C5 C3 H3 110.5 4_565 . ? C2 C3 H3 110.5 . . ? N1 C4 C5 111.4(5) . . ? N1 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C3 C5 C4 108.8(5) . . ? C3 C5 H5A 109.9 . . ? C4 C5 H5A 109.9 . . ? C3 C5 H5B 109.9 . . ? C4 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? N2 C6 C9 107.5(5) . . ? N2 C6 C10 114.6(5) . . ? C9 C6 C10 108.3(6) . . ? N2 C6 C7 107.4(5) . . ? C9 C6 C7 108.2(6) . . ? C10 C6 C7 110.7(5) . . ? C8 C7 C6 113.2(6) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 C7 109.7(9) . 4_565 ? C7 C8 H8A 109.7 . . ? C7 C8 H8A 109.7 4_565 . ? C7 C8 H8B 109.7 . . ? C7 C8 H8B 109.7 4_565 . ? H8A C8 H8B 108.2 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C6 C10 H10A 109.5 . . ? C6 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C6 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 2.488 _refine_diff_density_min -0.963 _refine_diff_density_rms 0.171 # Attachment 'cmpd3.CIF' data_compound3 _database_code_depnum_ccdc_archive 'CCDC 645536' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H50 Al N3 O2' _chemical_formula_weight 451.66 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)/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 12.707(3) _cell_length_b 11.963(2) _cell_length_c 17.660(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.14(3) _cell_angle_gamma 90.00 _cell_volume 2673.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18772 _diffrn_reflns_av_R_equivalents 0.0763 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.64 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6103 _reflns_number_gt 4199 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. The hydride ligand was located from difference maps and refined isotropically. ; _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^)+(0.0402P)^2^+1.5346P] 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 6103 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0970 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1197 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 0.66298(4) 0.15287(5) 0.06821(3) 0.02280(17) Uani 1 1 d . . . O1 O 0.75949(10) 0.10132(11) 0.13551(8) 0.0257(3) Uani 1 1 d . . . O2 O 0.65403(10) 0.29702(11) 0.05081(8) 0.0262(3) Uani 1 1 d . . . N1 N 0.84562(12) 0.03104(13) 0.11347(9) 0.0228(4) Uani 1 1 d . . . N2 N 0.74659(12) 0.36018(13) 0.03347(9) 0.0237(4) Uani 1 1 d . . . N3 N 0.53377(12) 0.14997(14) 0.12714(9) 0.0240(4) Uani 1 1 d . . . C1 C 0.82907(15) -0.08365(16) 0.14461(11) 0.0262(4) Uani 1 1 d . . . C2 C 0.92598(16) -0.15441(18) 0.13147(12) 0.0323(5) Uani 1 1 d . . . H2A H 0.9181 -0.2290 0.1545 0.039 Uiso 1 1 calc R . . H2B H 0.9291 -0.1650 0.0761 0.039 Uiso 1 1 calc R . . C3 C 1.02886(17) -0.10256(18) 0.16469(13) 0.0340(5) Uani 1 1 d . . . H3A H 1.0284 -0.0942 0.2204 0.041 Uiso 1 1 calc R . . H3B H 1.0892 -0.1509 0.1543 0.041 Uiso 1 1 calc R . . C4 C 1.03948(16) 0.01070(18) 0.12803(13) 0.0325(5) Uani 1 1 d . . . H4A H 1.0450 0.0001 0.0729 0.039 Uiso 1 1 calc R . . H4B H 1.1058 0.0462 0.1498 0.039 Uiso 1 1 calc R . . C5 C 0.94678(15) 0.08980(17) 0.13884(12) 0.0259(4) Uani 1 1 d . . . C6 C 0.73548(17) -0.13494(18) 0.09646(14) 0.0370(5) Uani 1 1 d . . . H6A H 0.6707 -0.0948 0.1058 0.055 Uiso 1 1 calc R . . H6B H 0.7284 -0.2138 0.1102 0.055 Uiso 1 1 calc R . . H6C H 0.7473 -0.1292 0.0425 0.055 Uiso 1 1 calc R . . C7 C 0.80695(18) -0.08719(19) 0.22867(12) 0.0352(5) Uani 1 1 d . . . H7A H 0.8728 -0.0740 0.2607 0.053 Uiso 1 1 calc R . . H7B H 0.7785 -0.1607 0.2405 0.053 Uiso 1 1 calc R . . H7C H 0.7554 -0.0292 0.2384 0.053 Uiso 1 1 calc R . . C8 C 0.95380(17) 0.13365(18) 0.22071(12) 0.0334(5) Uani 1 1 d . . . H8A H 0.8867 0.1690 0.2304 0.050 Uiso 1 1 calc R . . H8B H 1.0109 0.1887 0.2280 0.050 Uiso 1 1 calc R . . H8C H 0.9682 0.0713 0.2561 0.050 Uiso 1 1 calc R . . C9 C 0.95546(16) 0.18776(18) 0.08393(13) 0.0344(5) Uani 1 1 d . . . H9A H 0.9525 0.1595 0.0317 0.052 Uiso 1 1 calc R . . H9B H 1.0226 0.2267 0.0963 0.052 Uiso 1 1 calc R . . H9C H 0.8968 0.2397 0.0886 0.052 Uiso 1 1 calc R . . C10 C 0.73725(16) 0.38404(19) -0.04970(12) 0.0314(5) Uani 1 1 d . . . C11 C 0.83455(18) 0.4529(2) -0.06517(15) 0.0491(7) Uani 1 1 d . . . H11A H 0.8983 0.4056 -0.0558 0.059 Uiso 1 1 calc R . . H11B H 0.8286 0.4751 -0.1194 0.059 Uiso 1 1 calc R . . C12 C 0.8481(2) 0.5571(2) -0.01633(17) 0.0542(7) Uani 1 1 d . . . H12A H 0.9142 0.5960 -0.0265 0.065 Uiso 1 1 calc R . . H12B H 0.7882 0.6087 -0.0290 0.065 Uiso 1 1 calc R . . C13 C 0.85248(17) 0.5251(2) 0.06644(15) 0.0409(6) Uani 1 1 d . . . H13A H 0.8575 0.5939 0.0977 0.049 Uiso 1 1 calc R . . H13B H 0.9172 0.4805 0.0797 0.049 Uiso 1 1 calc R . . C14 C 0.75641(15) 0.45758(17) 0.08635(12) 0.0287(5) Uani 1 1 d . . . C15 C 0.63454(17) 0.4421(2) -0.08173(14) 0.0400(6) Uani 1 1 d . . . H15A H 0.5738 0.4050 -0.0621 0.060 Uiso 1 1 calc R . . H15B H 0.6282 0.4375 -0.1374 0.060 Uiso 1 1 calc R . . H15C H 0.6362 0.5207 -0.0661 0.060 Uiso 1 1 calc R . . C16 C 0.7429(2) 0.2720(2) -0.09021(13) 0.0446(6) Uani 1 1 d . . . H16A H 0.8001 0.2269 -0.0649 0.067 Uiso 1 1 calc R . . H16B H 0.7565 0.2846 -0.1433 0.067 Uiso 1 1 calc R . . H16C H 0.6756 0.2323 -0.0885 0.067 Uiso 1 1 calc R . . C17 C 0.65723(17) 0.53117(18) 0.08678(15) 0.0386(6) Uani 1 1 d . . . H17A H 0.6511 0.5787 0.0414 0.058 Uiso 1 1 calc R . . H17B H 0.6628 0.5782 0.1324 0.058 Uiso 1 1 calc R . . H17C H 0.5945 0.4835 0.0868 0.058 Uiso 1 1 calc R . . C18 C 0.78129(17) 0.41133(19) 0.16656(12) 0.0345(5) Uani 1 1 d . . . H18A H 0.7193 0.3718 0.1823 0.052 Uiso 1 1 calc R . . H18B H 0.7994 0.4731 0.2018 0.052 Uiso 1 1 calc R . . H18C H 0.8411 0.3595 0.1671 0.052 Uiso 1 1 calc R . . C19 C 0.44009(16) 0.1930(2) 0.07777(12) 0.0338(5) Uani 1 1 d . . . H19A H 0.4250 0.1422 0.0339 0.041 Uiso 1 1 calc R . . H19B H 0.4567 0.2677 0.0579 0.041 Uiso 1 1 calc R . . C20 C 0.34200(18) 0.2013(3) 0.12246(15) 0.0555(8) Uani 1 1 d . . . H20A H 0.3227 0.2807 0.1286 0.067 Uiso 1 1 calc R . . H20B H 0.2816 0.1629 0.0942 0.067 Uiso 1 1 calc R . . C21 C 0.36520(16) 0.14755(19) 0.19994(13) 0.0335(5) Uani 1 1 d . . . H21 H 0.3002 0.1467 0.2280 0.040 Uiso 1 1 calc R . . C22 C 0.45211(18) 0.2149(2) 0.24359(14) 0.0451(6) Uani 1 1 d . . . H22A H 0.4728 0.1788 0.2931 0.054 Uiso 1 1 calc R . . H22B H 0.4262 0.2911 0.2534 0.054 Uiso 1 1 calc R . . C23 C 0.54819(16) 0.22169(19) 0.19663(12) 0.0310(5) Uani 1 1 d . . . H23A H 0.5588 0.3002 0.1814 0.037 Uiso 1 1 calc R . . H23B H 0.6122 0.1974 0.2284 0.037 Uiso 1 1 calc R . . C24 C 0.4049(2) 0.0301(2) 0.18994(18) 0.0552(8) Uani 1 1 d . . . H24A H 0.3512 -0.0136 0.1584 0.066 Uiso 1 1 calc R . . H24B H 0.4171 -0.0067 0.2401 0.066 Uiso 1 1 calc R . . C25 C 0.50858(16) 0.03323(17) 0.15122(13) 0.0332(5) Uani 1 1 d . . . H25A H 0.5670 0.0048 0.1869 0.040 Uiso 1 1 calc R . . H25B H 0.5023 -0.0163 0.1061 0.040 Uiso 1 1 calc R . . H1 H 0.6310(17) 0.0760(19) -0.0009(13) 0.041(6) 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 0.0238(3) 0.0198(3) 0.0249(3) -0.0004(2) 0.0026(2) -0.0008(2) O1 0.0224(7) 0.0237(7) 0.0310(8) -0.0027(6) 0.0022(6) 0.0047(6) O2 0.0261(7) 0.0213(7) 0.0316(8) 0.0023(6) 0.0058(6) -0.0027(6) N1 0.0225(8) 0.0198(8) 0.0262(8) -0.0019(7) 0.0032(6) 0.0051(7) N2 0.0216(8) 0.0219(9) 0.0278(9) 0.0048(7) 0.0044(7) 0.0000(7) N3 0.0232(8) 0.0223(9) 0.0265(9) 0.0023(7) 0.0014(7) -0.0007(7) C1 0.0306(10) 0.0196(10) 0.0281(11) 0.0010(8) 0.0016(8) 0.0005(8) C2 0.0389(11) 0.0227(10) 0.0345(12) -0.0015(9) -0.0005(9) 0.0058(10) C3 0.0332(11) 0.0296(12) 0.0387(12) -0.0004(10) 0.0010(9) 0.0099(9) C4 0.0262(10) 0.0323(12) 0.0393(12) 0.0007(10) 0.0035(9) 0.0045(9) C5 0.0237(9) 0.0231(10) 0.0305(11) 0.0005(9) 0.0012(8) 0.0010(8) C6 0.0380(12) 0.0245(11) 0.0468(14) -0.0061(10) -0.0060(10) -0.0012(10) C7 0.0405(12) 0.0295(12) 0.0361(12) 0.0056(10) 0.0071(10) -0.0003(10) C8 0.0336(11) 0.0294(12) 0.0357(12) -0.0079(10) -0.0046(9) -0.0018(9) C9 0.0281(11) 0.0303(12) 0.0454(13) 0.0065(10) 0.0076(9) 0.0005(9) C10 0.0270(10) 0.0389(13) 0.0285(11) 0.0121(10) 0.0040(8) 0.0041(9) C11 0.0331(12) 0.0706(19) 0.0443(14) 0.0279(14) 0.0066(10) -0.0031(13) C12 0.0369(13) 0.0510(16) 0.0746(19) 0.0279(15) 0.0049(13) -0.0150(12) C13 0.0304(11) 0.0322(13) 0.0595(16) 0.0051(12) 0.0006(11) -0.0066(10) C14 0.0239(10) 0.0225(10) 0.0396(12) -0.0008(9) 0.0025(9) 0.0010(8) C15 0.0356(12) 0.0430(14) 0.0399(13) 0.0141(11) -0.0040(10) 0.0020(11) C16 0.0486(14) 0.0588(16) 0.0272(12) 0.0032(11) 0.0083(10) 0.0151(13) C17 0.0331(11) 0.0257(11) 0.0573(15) -0.0049(11) 0.0050(11) 0.0043(10) C18 0.0358(11) 0.0318(12) 0.0354(12) -0.0083(10) 0.0005(9) 0.0003(10) C19 0.0257(10) 0.0443(13) 0.0312(11) 0.0072(10) 0.0013(9) 0.0021(10) C20 0.0285(12) 0.092(2) 0.0463(15) 0.0206(15) 0.0059(11) 0.0092(13) C21 0.0259(10) 0.0377(12) 0.0384(12) 0.0060(10) 0.0104(9) 0.0007(10) C22 0.0389(13) 0.0546(16) 0.0440(14) -0.0076(12) 0.0159(11) -0.0045(12) C23 0.0311(10) 0.0323(12) 0.0298(11) -0.0043(9) 0.0037(9) -0.0039(9) C24 0.0545(15) 0.0319(13) 0.086(2) 0.0038(13) 0.0416(15) -0.0038(12) C25 0.0336(11) 0.0213(11) 0.0459(13) 0.0038(10) 0.0110(10) -0.0010(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 O1 1.7423(15) . ? Al1 O2 1.7535(15) . ? Al1 N3 2.0215(17) . ? Al1 H1 1.55(2) . ? O1 N1 1.4602(19) . ? O2 N2 1.453(2) . ? N1 C5 1.498(2) . ? N1 C1 1.500(2) . ? N2 C10 1.490(3) . ? N2 C14 1.492(3) . ? N3 C23 1.495(3) . ? N3 C19 1.502(3) . ? N3 C25 1.503(3) . ? C1 C6 1.527(3) . ? C1 C2 1.529(3) . ? C1 C7 1.536(3) . ? C2 C3 1.517(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.513(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.536(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C9 1.531(3) . ? C5 C8 1.533(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C16 1.524(3) . ? C10 C11 1.531(3) . ? C10 C15 1.541(3) . ? C11 C12 1.516(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.507(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.531(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C18 1.527(3) . ? C14 C17 1.538(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.537(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.516(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C24 1.508(3) . ? C21 C22 1.520(3) . ? C21 H21 1.0000 . ? C22 C23 1.538(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.539(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Al1 O2 119.89(7) . . ? O1 Al1 N3 101.38(7) . . ? O2 Al1 N3 93.68(7) . . ? O1 Al1 H1 116.5(8) . . ? O2 Al1 H1 115.8(8) . . ? N3 Al1 H1 103.1(8) . . ? N1 O1 Al1 121.37(11) . . ? N2 O2 Al1 120.48(10) . . ? O1 N1 C5 107.08(13) . . ? O1 N1 C1 107.22(14) . . ? C5 N1 C1 117.67(15) . . ? O2 N2 C10 108.22(14) . . ? O2 N2 C14 107.35(14) . . ? C10 N2 C14 117.52(16) . . ? C23 N3 C19 108.20(16) . . ? C23 N3 C25 108.34(16) . . ? C19 N3 C25 107.74(16) . . ? C23 N3 Al1 111.55(12) . . ? C19 N3 Al1 109.47(12) . . ? C25 N3 Al1 111.41(12) . . ? N1 C1 C6 106.92(16) . . ? N1 C1 C2 108.03(16) . . ? C6 C1 C2 106.90(17) . . ? N1 C1 C7 115.04(16) . . ? C6 C1 C7 109.04(18) . . ? C2 C1 C7 110.55(17) . . ? C3 C2 C1 113.13(17) . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 107.92(17) . . ? C4 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? C4 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C3 C4 C5 113.56(18) . . ? C3 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? C3 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N1 C5 C9 106.16(16) . . ? N1 C5 C8 114.74(16) . . ? C9 C5 C8 109.50(17) . . ? N1 C5 C4 108.72(16) . . ? C9 C5 C4 107.04(17) . . ? C8 C5 C4 110.34(17) . . ? C1 C6 H6A 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C16 106.92(17) . . ? N2 C10 C11 106.55(17) . . ? C16 C10 C11 108.5(2) . . ? N2 C10 C15 115.98(17) . . ? C16 C10 C15 107.33(18) . . ? C11 C10 C15 111.28(19) . . ? C12 C11 C10 113.2(2) . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11B 108.9 . . ? C10 C11 H11B 108.9 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 109.6(2) . . ? C13 C12 H12A 109.8 . . ? C11 C12 H12A 109.8 . . ? C13 C12 H12B 109.8 . . ? C11 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? C12 C13 C14 113.33(19) . . ? C12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? N2 C14 C18 107.25(16) . . ? N2 C14 C13 106.98(17) . . ? C18 C14 C13 107.52(17) . . ? N2 C14 C17 115.32(16) . . ? C18 C14 C17 107.72(18) . . ? C13 C14 C17 111.71(18) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C10 C16 H16A 109.5 . . ? C10 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C10 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 C20 111.17(17) . . ? N3 C19 H19A 109.4 . . ? C20 C19 H19A 109.4 . . ? N3 C19 H19B 109.4 . . ? C20 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C21 C20 C19 109.57(18) . . ? C21 C20 H20A 109.8 . . ? C19 C20 H20A 109.8 . . ? C21 C20 H20B 109.8 . . ? C19 C20 H20B 109.8 . . ? H20A C20 H20B 108.2 . . ? C24 C21 C20 109.2(2) . . ? C24 C21 C22 108.5(2) . . ? C20 C21 C22 107.9(2) . . ? C24 C21 H21 110.4 . . ? C20 C21 H21 110.4 . . ? C22 C21 H21 110.4 . . ? C21 C22 C23 109.28(19) . . ? C21 C22 H22A 109.8 . . ? C23 C22 H22A 109.8 . . ? C21 C22 H22B 109.8 . . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.3 . . ? N3 C23 C22 111.57(17) . . ? N3 C23 H23A 109.3 . . ? C22 C23 H23A 109.3 . . ? N3 C23 H23B 109.3 . . ? C22 C23 H23B 109.3 . . ? H23A C23 H23B 108.0 . . ? C21 C24 C25 109.78(18) . . ? C21 C24 H24A 109.7 . . ? C25 C24 H24A 109.7 . . ? C21 C24 H24B 109.7 . . ? C25 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? N3 C25 C24 111.14(17) . . ? N3 C25 H25A 109.4 . . ? C24 C25 H25A 109.4 . . ? N3 C25 H25B 109.4 . . ? C24 C25 H25B 109.4 . . ? H25A C25 H25B 108.0 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.335 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.049