# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'D. S. Wright' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email DSW1000@CAM.AC.UK _publ_section_title ; Pyridyl 'Ring-Flipping' in the Dimers [Me2E(2-py)2]2 (E= B, Al, Ga; 2-py= 2-pyridyl) ; loop_ _publ_author_name 'D. S. Wright' 'Felipe Garcia' 'Alexander Hopkins' 'Richard A. Kowenicki' 'M. McPartlin' ; M.C.Rogers ; 'Jared Silvia' # Attachment 'comp3.cif' data_mw0530 _database_code_depnum_ccdc_archive 'CCDC 621854' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 Ga2 N2' _chemical_formula_weight 355.76 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.016(3) _cell_length_b 16.479(3) _cell_length_c 14.743(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.21(3) _cell_angle_gamma 90.00 _cell_volume 3152.4(11) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 23909 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 20.39 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 3.404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_correction_T_max 0.915 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 9210 _diffrn_reflns_av_R_equivalents 0.0633 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.83 _diffrn_reflns_theta_max 20.39 _reflns_number_total 1553 _reflns_number_gt 1331 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0590P)^2^+3.0330P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1553 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1226 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.367 _refine_ls_restrained_S_all 1.367 _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 0.03635(5) 0.15634(4) 0.07352(4) 0.0359(4) Uani 1 1 d . . . Ga2 Ga 0.02961(5) 0.34555(4) -0.04347(5) 0.0391(4) Uani 1 1 d . . . N1 N 0.0803(4) 0.1696(3) -0.0418(4) 0.0351(14) Uani 0.50 1 d P A 1 C1 C 0.0833(4) 0.2429(3) -0.0830(3) 0.0392(14) Uani 0.50 1 d P A 1 N1' N 0.0833(4) 0.2429(3) -0.0830(3) 0.0392(14) Uani 0.50 1 d P A 2 C1' C 0.0803(4) 0.1696(3) -0.0418(4) 0.0351(14) Uani 0.50 1 d P A 2 C2 C 0.1171(5) 0.2466(5) -0.1584(5) 0.0547(18) Uani 1 1 d . . . H2 H 0.1210 0.2970 -0.1853 0.066 Uiso 1 1 calc R A 1 C3 C 0.1456(6) 0.1786(6) -0.1964(5) 0.064(2) Uani 1 1 d . A . H3 H 0.1669 0.1825 -0.2488 0.077 Uiso 1 1 calc R . . C4 C 0.1418(5) 0.1056(5) -0.1552(5) 0.066(2) Uani 1 1 d . . . H4 H 0.1613 0.0586 -0.1786 0.080 Uiso 1 1 calc R A . C5 C 0.1089(5) 0.1018(4) -0.0785(5) 0.0515(18) Uani 1 1 d . A . H5 H 0.1061 0.0517 -0.0508 0.062 Uiso 1 1 calc R B 1 N2 N 0.0792(4) 0.3350(3) 0.1036(4) 0.0343(14) Uani 0.50 1 d P A 1 C6 C 0.0834(4) 0.2613(3) 0.1491(4) 0.0344(13) Uani 0.50 1 d P A 1 N2' N 0.0834(4) 0.2613(3) 0.1491(4) 0.0344(13) Uani 0.50 1 d P A 2 C6' C 0.0792(4) 0.3350(3) 0.1036(4) 0.0343(14) Uani 0.50 1 d P A 2 C7 C 0.1170(4) 0.2598(4) 0.2493(4) 0.0430(17) Uani 1 1 d . . . H7 H 0.1211 0.2101 0.2806 0.052 Uiso 1 1 calc R A 1 C8 C 0.1445(5) 0.3284(6) 0.3047(5) 0.057(2) Uani 1 1 d . A . H8 H 0.1662 0.3254 0.3725 0.068 Uiso 1 1 calc R . . C9 C 0.1402(5) 0.4013(5) 0.2601(6) 0.063(2) Uani 1 1 d . . . H9 H 0.1587 0.4489 0.2965 0.075 Uiso 1 1 calc R A . C10 C 0.1081(4) 0.4025(4) 0.1611(5) 0.0457(16) Uani 1 1 d . A . H10 H 0.1057 0.4523 0.1306 0.055 Uiso 1 1 calc R C 1 C11 C 0.1206(6) 0.0673(4) 0.1571(5) 0.062(2) Uani 1 1 d . A . H11A H 0.1924 0.0798 0.1762 0.094 Uiso 1 1 calc R . . H11B H 0.1055 0.0173 0.1209 0.094 Uiso 1 1 calc R . . H11C H 0.1043 0.0617 0.2145 0.094 Uiso 1 1 calc R . . C12 C -0.1159(6) 0.1443(4) 0.0250(5) 0.0528(19) Uani 1 1 d . A . H12A H -0.1481 0.1906 -0.0142 0.079 Uiso 1 1 calc R . . H12B H -0.1370 0.1405 0.0797 0.079 Uiso 1 1 calc R . . H12C H -0.1362 0.0960 -0.0140 0.079 Uiso 1 1 calc R . . C21 C 0.1021(5) 0.4380(4) -0.0754(5) 0.0595(19) Uani 1 1 d . A . H21A H 0.1752 0.4304 -0.0438 0.089 Uiso 1 1 calc R . . H21B H 0.0827 0.4876 -0.0528 0.089 Uiso 1 1 calc R . . H21C H 0.0835 0.4407 -0.1451 0.089 Uiso 1 1 calc R . . C22 C -0.1223(6) 0.3487(4) -0.0999(5) 0.0522(19) Uani 1 1 d . A . H22A H -0.1491 0.3011 -0.0803 0.078 Uiso 1 1 calc R . . H22B H -0.1460 0.3503 -0.1701 0.078 Uiso 1 1 calc R . . H22C H -0.1459 0.3961 -0.0769 0.078 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 Ga1 0.0412(6) 0.0325(5) 0.0339(5) 0.0026(3) 0.0141(4) -0.0011(3) Ga2 0.0405(6) 0.0381(6) 0.0405(5) 0.0107(3) 0.0172(4) 0.0055(3) N1 0.031(3) 0.040(4) 0.034(3) -0.004(3) 0.011(3) 0.004(3) C1 0.033(3) 0.055(4) 0.031(3) -0.002(3) 0.014(3) 0.006(3) N1' 0.033(3) 0.055(4) 0.031(3) -0.002(3) 0.014(3) 0.006(3) C1' 0.031(3) 0.040(4) 0.034(3) -0.004(3) 0.011(3) 0.004(3) C2 0.054(5) 0.073(5) 0.046(4) 0.007(4) 0.029(4) 0.004(4) C3 0.050(5) 0.108(7) 0.040(4) -0.006(5) 0.025(4) 0.001(5) C4 0.044(4) 0.095(7) 0.061(5) -0.041(5) 0.021(4) 0.006(4) C5 0.047(4) 0.049(5) 0.060(4) -0.021(4) 0.022(3) -0.002(4) N2 0.031(3) 0.039(4) 0.033(3) -0.004(3) 0.013(3) 0.003(3) C6 0.028(3) 0.045(4) 0.033(3) 0.002(3) 0.016(2) 0.000(3) N2' 0.028(3) 0.045(4) 0.033(3) 0.002(3) 0.016(2) 0.000(3) C6' 0.031(3) 0.039(4) 0.033(3) -0.004(3) 0.013(3) 0.003(3) C7 0.036(4) 0.066(5) 0.029(4) 0.004(3) 0.014(3) 0.001(3) C8 0.034(4) 0.105(7) 0.032(4) -0.027(5) 0.014(3) -0.004(4) C9 0.038(4) 0.077(6) 0.074(6) -0.048(5) 0.023(4) -0.008(4) C10 0.035(4) 0.036(4) 0.067(5) -0.014(4) 0.020(3) 0.000(3) C11 0.074(5) 0.045(4) 0.059(4) 0.011(3) 0.014(4) 0.008(4) C12 0.054(5) 0.049(4) 0.057(4) -0.008(3) 0.022(4) -0.010(3) C21 0.056(5) 0.056(5) 0.068(4) 0.023(4) 0.026(4) 0.000(4) C22 0.052(5) 0.050(5) 0.053(4) 0.005(3) 0.018(4) 0.006(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 C12 1.988(7) . ? Ga1 C11 1.992(6) . ? Ga1 N1 2.027(5) . ? Ga1 C6 2.027(5) . ? Ga2 C22 1.973(7) . ? Ga2 C21 1.984(6) . ? Ga2 C1 2.025(5) . ? Ga2 N2 2.019(5) . ? N1 C5 1.366(8) . ? N1 C1 1.360(7) . ? C1 C2 1.364(7) . ? C2 C3 1.379(10) . ? C3 C4 1.357(10) . ? C4 C5 1.374(9) . ? N2 C10 1.365(8) . ? N2 C6 1.378(7) . ? C6 C7 1.371(7) . ? C7 C8 1.362(9) . ? C8 C9 1.360(10) . ? C9 C10 1.355(9) . ? 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 C12 Ga1 C11 117.0(3) . . ? C12 Ga1 N1 109.5(3) . . ? C11 Ga1 N1 107.6(3) . . ? C12 Ga1 C6 111.4(2) . . ? C11 Ga1 C6 107.2(3) . . ? N1 Ga1 C6 103.3(2) . . ? C22 Ga2 C21 116.6(3) . . ? C22 Ga2 C1 111.1(2) . . ? C21 Ga2 C1 107.1(3) . . ? C22 Ga2 N2 109.5(3) . . ? C21 Ga2 N2 108.8(3) . . ? C1 Ga2 N2 102.9(2) . . ? C5 N1 C1 119.0(5) . . ? C5 N1 Ga1 118.2(4) . . ? C1 N1 Ga1 122.8(4) . . ? C2 C1 N1 118.9(5) . . ? C2 C1 Ga2 118.6(5) . . ? N1 C1 Ga2 122.3(4) . . ? C1 C2 C3 122.5(7) . . ? C4 C3 C2 118.2(6) . . ? C3 C4 C5 119.4(7) . . ? N1 C5 C4 122.0(7) . . ? C10 N2 C6 117.9(5) . . ? C10 N2 Ga2 119.9(4) . . ? C6 N2 Ga2 122.2(4) . . ? N2 C6 C7 118.3(5) . . ? N2 C6 Ga1 122.6(4) . . ? C7 C6 Ga1 119.0(4) . . ? C8 C7 C6 122.3(6) . . ? C9 C8 C7 119.5(6) . . ? C8 C9 C10 118.0(6) . . ? N2 C10 C9 123.8(6) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 20.39 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.239 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.093 # Attachment 'comp21.cif' data_dw0451 _database_code_depnum_ccdc_archive 'CCDC 621855' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 Al2 N2' _chemical_formula_sum 'C14 H20 Al2 N2' _chemical_formula_weight 270.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.027(3) _cell_length_b 16.564(3) _cell_length_c 14.656(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.26(3) _cell_angle_gamma 90.00 _cell_volume 3151.5(11) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11466 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description rods _exptl_crystal_colour colourless _exptl_crystal_size_max 0.81 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 12895 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3605 _reflns_number_gt 2441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0590P)^2^+3.0330P] 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 3605 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0846 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1404 _refine_ls_wR_factor_gt 0.1208 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.04043(5) 0.15710(4) 0.07423(5) 0.03324(19) Uani 1 1 d . . . Al2 Al 0.03265(5) 0.34477(4) -0.04015(5) 0.03499(19) Uani 1 1 d . . . N1 N 0.08135(15) 0.17070(12) -0.04094(15) 0.0355(5) Uani 0.50 1 d P A 1 C1 C 0.08519(14) 0.24509(12) -0.08155(14) 0.0353(5) Uani 0.50 1 d P A 1 N1' N 0.08519(14) 0.24509(12) -0.08155(14) 0.0353(5) Uani 0.50 1 d P A 2 C1' C 0.08135(15) 0.17070(12) -0.04094(15) 0.0355(5) Uani 0.50 1 d P A 2 C2 C 0.11816(19) 0.24941(17) -0.15859(19) 0.0485(6) Uani 1 1 d . . . H2 H 0.1222 0.3008 -0.1856 0.058 Uiso 1 1 calc R A 1 C3 C 0.1455(2) 0.1823(2) -0.1979(2) 0.0570(7) Uani 1 1 d . A . H3 H 0.1682 0.1872 -0.2511 0.068 Uiso 1 1 calc R . . C4 C 0.13950(19) 0.10867(19) -0.1593(2) 0.0572(8) Uani 1 1 d . . . H4 H 0.1566 0.0611 -0.1861 0.069 Uiso 1 1 calc R A . C5 C 0.10825(18) 0.10400(16) -0.0809(2) 0.0477(6) Uani 1 1 d . A . H5 H 0.1053 0.0525 -0.0536 0.057 Uiso 1 1 calc R B 1 N2 N 0.08130(14) 0.33406(11) 0.10521(14) 0.0320(4) Uani 0.50 1 d P A 1 C6 C 0.08527(14) 0.26027(12) 0.14967(14) 0.0324(4) Uani 0.50 1 d P A 1 N2' N 0.08527(14) 0.26027(12) 0.14967(14) 0.0324(4) Uani 0.50 1 d P A 2 C6' C 0.08130(14) 0.33406(11) 0.10521(14) 0.0320(4) Uani 0.50 1 d P A 2 C7 C 0.11835(17) 0.25762(15) 0.25116(17) 0.0411(5) Uani 1 1 d . . . H7 H 0.1225 0.2068 0.2825 0.049 Uiso 1 1 calc R A 1 C8 C 0.14558(18) 0.32601(19) 0.30859(19) 0.0509(7) Uani 1 1 d . A . H8 H 0.1669 0.3225 0.3782 0.061 Uiso 1 1 calc R . . C9 C 0.14153(18) 0.39902(18) 0.2640(2) 0.0524(7) Uani 1 1 d . . . H9 H 0.1603 0.4471 0.3021 0.063 Uiso 1 1 calc R A . C10 C 0.10984(17) 0.40174(15) 0.1630(2) 0.0455(6) Uani 1 1 d . A . H10 H 0.1077 0.4525 0.1322 0.055 Uiso 1 1 calc R C 1 C11 C 0.1236(2) 0.06904(16) 0.1566(2) 0.0566(7) Uani 1 1 d . A . H11A H 0.1969 0.0817 0.1762 0.085 Uiso 1 1 calc R . . H11B H 0.1080 0.0185 0.1191 0.085 Uiso 1 1 calc R . . H11C H 0.1072 0.0631 0.2157 0.085 Uiso 1 1 calc R . . C12 C -0.10907(19) 0.14123(17) 0.0289(2) 0.0525(7) Uani 1 1 d . A . H12A H -0.1446 0.1874 -0.0114 0.079 Uiso 1 1 calc R . . H12B H -0.1288 0.1366 0.0861 0.079 Uiso 1 1 calc R . . H12C H -0.1284 0.0918 -0.0105 0.079 Uiso 1 1 calc R . . C21 C 0.1005(2) 0.43803(16) -0.0736(2) 0.0547(7) Uani 1 1 d . A . H21A H 0.1754 0.4318 -0.0421 0.082 Uiso 1 1 calc R . . H21B H 0.0796 0.4877 -0.0499 0.082 Uiso 1 1 calc R . . H21C H 0.0802 0.4410 -0.1452 0.082 Uiso 1 1 calc R . . C22 C -0.11803(19) 0.34732(17) -0.0971(2) 0.0511(6) Uani 1 1 d . A . H22A H -0.1451 0.2988 -0.0770 0.077 Uiso 1 1 calc R . . H22B H -0.1419 0.3490 -0.1691 0.077 Uiso 1 1 calc R . . H22C H -0.1425 0.3954 -0.0736 0.077 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 0.0391(4) 0.0285(3) 0.0320(4) 0.0002(3) 0.0133(3) -0.0014(3) Al2 0.0382(4) 0.0320(4) 0.0356(4) 0.0061(3) 0.0149(3) 0.0047(3) N1 0.0344(10) 0.0374(11) 0.0347(11) -0.0045(9) 0.0130(8) 0.0008(8) C1 0.0336(10) 0.0413(12) 0.0314(10) 0.0024(9) 0.0128(8) 0.0054(8) N1' 0.0336(10) 0.0413(12) 0.0314(10) 0.0024(9) 0.0128(8) 0.0054(8) C1' 0.0344(10) 0.0374(11) 0.0347(11) -0.0045(9) 0.0130(8) 0.0008(8) C2 0.0469(14) 0.0647(17) 0.0395(13) 0.0092(12) 0.0227(11) 0.0071(12) C3 0.0446(14) 0.090(2) 0.0434(15) -0.0073(15) 0.0240(12) 0.0063(14) C4 0.0456(14) 0.070(2) 0.0611(18) -0.0301(16) 0.0257(13) 0.0006(13) C5 0.0484(14) 0.0396(14) 0.0572(16) -0.0098(12) 0.0223(12) 0.0016(10) N2 0.0304(10) 0.0302(10) 0.0343(10) -0.0025(8) 0.0110(8) 0.0028(7) C6 0.0309(9) 0.0369(11) 0.0303(10) -0.0018(8) 0.0125(8) -0.0015(8) N2' 0.0309(9) 0.0369(11) 0.0303(10) -0.0018(8) 0.0125(8) -0.0015(8) C6' 0.0304(10) 0.0302(10) 0.0343(10) -0.0025(8) 0.0110(8) 0.0028(7) C7 0.0365(12) 0.0536(15) 0.0320(12) 0.0018(11) 0.0115(9) -0.0021(10) C8 0.0366(13) 0.082(2) 0.0342(13) -0.0164(13) 0.0138(10) -0.0052(12) C9 0.0404(13) 0.0598(18) 0.0550(17) -0.0307(14) 0.0158(11) -0.0007(11) C10 0.0433(13) 0.0323(12) 0.0595(16) -0.0095(11) 0.0179(11) 0.0032(10) C11 0.0737(18) 0.0377(14) 0.0536(16) 0.0065(12) 0.0187(14) 0.0076(12) C12 0.0457(14) 0.0525(16) 0.0582(17) -0.0151(13) 0.0185(12) -0.0076(11) C21 0.0566(16) 0.0456(15) 0.0632(18) 0.0168(13) 0.0240(13) 0.0016(11) C22 0.0427(14) 0.0588(17) 0.0497(15) -0.0031(13) 0.0152(11) 0.0034(11) _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 C12 1.963(3) . ? Al1 C11 1.970(3) . ? Al1 N1 1.991(2) . ? Al1 C6 2.003(2) . ? Al2 C22 1.957(3) . ? Al2 C21 1.971(3) . ? Al2 N2 1.983(2) . ? Al2 C1 1.994(2) . ? N1 C5 1.369(3) . ? N1 C1 1.378(3) . ? C1 C2 1.375(3) . ? C2 C3 1.372(4) . ? C3 C4 1.360(4) . ? C4 C5 1.379(4) . ? N2 C10 1.371(3) . ? N2 C6 1.376(3) . ? C6 C7 1.381(3) . ? C7 C8 1.376(3) . ? C8 C9 1.365(4) . ? C9 C10 1.376(4) . ? 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 C12 Al1 C11 114.65(13) . . ? C12 Al1 N1 110.02(11) . . ? C11 Al1 N1 108.04(11) . . ? C12 Al1 C6 111.90(10) . . ? C11 Al1 C6 107.70(11) . . ? N1 Al1 C6 103.91(8) . . ? C22 Al2 C21 114.98(12) . . ? C22 Al2 N2 109.65(11) . . ? C21 Al2 N2 109.57(11) . . ? C22 Al2 C1 110.62(10) . . ? C21 Al2 C1 107.74(11) . . ? N2 Al2 C1 103.67(8) . . ? C5 N1 C1 118.3(2) . . ? C5 N1 Al1 119.10(17) . . ? C1 N1 Al1 122.57(15) . . ? C2 C1 N1 118.8(2) . . ? C2 C1 Al2 119.01(17) . . ? N1 C1 Al2 121.97(15) . . ? C1 C2 C3 122.5(3) . . ? C4 C3 C2 118.7(2) . . ? C3 C4 C5 119.1(2) . . ? N1 C5 C4 122.5(3) . . ? C10 N2 C6 118.9(2) . . ? C10 N2 Al2 119.47(17) . . ? C6 N2 Al2 121.59(14) . . ? N2 C6 C7 118.36(19) . . ? N2 C6 Al1 123.26(14) . . ? C7 C6 Al1 118.34(16) . . ? C6 C7 C8 122.3(2) . . ? C9 C8 C7 119.0(2) . . ? C8 C9 C10 118.8(2) . . ? N2 C10 C9 122.6(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.329 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.049