# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1366 data_VG9808 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H37 N2 O Al' _chemical_formula_weight 360.51 _chemical_melting_point ? _chemical_compound_source ? 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 10.332(2) _cell_length_b 24.982(4) _cell_length_c 9.729(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.984(12) _cell_angle_gamma 90.00 _cell_volume 2257.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4.64 _cell_measurement_theta_max 12.46 _exptl_crystal_description 'platy needles' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.93 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.061 _exptl_crystal_density_method ? _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 43.58 _diffrn_reflns_number 3134 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0963 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2934 _reflns_number_observed 1646 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 400 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0963P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2534 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1359 _refine_ls_R_factor_obs 0.0673 _refine_ls_wR_factor_all 0.1994 _refine_ls_wR_factor_obs 0.1557 _refine_ls_goodness_of_fit_all 0.993 _refine_ls_goodness_of_fit_obs 1.082 _refine_ls_restrained_S_all 1.013 _refine_ls_restrained_S_obs 1.082 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Al Al 0.1911(2) 0.00561(6) 0.3436(2) 0.0397(4) Uani 1 d . . N1 N 0.2132(5) -0.0898(2) 0.3854(5) 0.0521(12) Uani 1 d . . C2 C 0.1317(7) -0.1083(2) 0.2279(7) 0.057(2) Uani 1 d . . H2A H 0.1211(7) -0.1469(2) 0.2268(7) 0.069 Uiso 1 calc R . H2B H 0.1835(7) -0.0994(2) 0.1686(7) 0.069 Uiso 1 calc R . C3 C -0.0143(6) -0.0825(2) 0.1578(7) 0.057(2) Uani 1 d . . H3A H -0.0578(6) -0.0869(2) 0.0476(7) 0.069 Uiso 1 calc R . H3B H -0.0764(6) -0.0993(2) 0.1964(7) 0.069 Uiso 1 calc R . N4 N 0.0014(4) -0.0245(2) 0.1970(5) 0.0438(11) Uani 1 d . . C5 C -0.1168(5) 0.0028(2) 0.1408(6) 0.0425(12) Uani 1 d . . H5A H -0.2014(5) -0.0164(2) 0.0885(6) 0.051 Uiso 1 calc R . C6 C -0.1321(5) 0.0596(2) 0.1504(6) 0.0408(12) Uani 1 d . . C7 C -0.2721(6) 0.0803(2) 0.0875(6) 0.0493(14) Uani 1 d . . H7A H -0.3499(6) 0.0569(2) 0.0495(6) 0.059 Uiso 1 calc R . C8 C -0.2974(6) 0.1352(2) 0.0804(6) 0.0474(13) Uani 1 d . . C9 C -0.1733(6) 0.1676(2) 0.1458(7) 0.0507(14) Uani 1 d . . H9A H -0.1875(6) 0.2043(2) 0.1455(7) 0.061 Uiso 1 calc R . C10 C -0.0339(6) 0.1499(2) 0.2097(6) 0.0415(12) Uani 1 d . . C11 C -0.0105(5) 0.0932(2) 0.2150(6) 0.0378(12) Uani 1 d . . O12 O 0.1197(3) 0.07316(13) 0.2705(5) 0.0475(10) Uani 1 d . . C13 C 0.2268(7) 0.0161(2) 0.5589(7) 0.0580(15) Uani 1 d . . H13A H 0.1379(7) 0.0124(2) 0.5672(7) 0.087 Uiso 1 d R . H13B H 0.2657(7) 0.0512(2) 0.5920(7) 0.087 Uiso 1 d R . H13C H 0.2941(7) -0.0103(2) 0.6220(7) 0.087 Uiso 1 d R . C14 C 0.3448(5) 0.0054(2) 0.2746(6) 0.0515(13) Uani 1 d . . H14A H 0.4363(5) 0.0000(2) 0.3609(6) 0.077 Uiso 1 d R . H14B H 0.3452(5) 0.0391(2) 0.2273(6) 0.077 Uiso 1 d R . H14C H 0.3275(5) -0.0230(2) 0.2021(6) 0.077 Uiso 1 d R . C15 C 0.3613(7) -0.1099(3) 0.4462(10) 0.084(2) Uani 1 d . . H15A H 0.4052(7) -0.0975(3) 0.3832(10) 0.127 Uiso 1 calc R . H15B H 0.3603(7) -0.1484(3) 0.4464(10) 0.127 Uiso 1 calc R . H15C H 0.4153(7) -0.0971(3) 0.5488(10) 0.127 Uiso 1 calc R . C16 C 0.1456(9) -0.1084(2) 0.4799(8) 0.074(2) Uani 1 d . . H16A H 0.1999(9) -0.0961(2) 0.5829(8) 0.112 Uiso 1 calc R . H16B H 0.1429(9) -0.1469(2) 0.4789(8) 0.112 Uiso 1 calc R . H16C H 0.0492(9) -0.0947(2) 0.4403(8) 0.112 Uiso 1 calc R . C17 C -0.4474(6) 0.1597(3) 0.0106(7) 0.060(2) Uani 1 d . . C18 C -0.5640(8) 0.1184(4) -0.0403(15) 0.138(5) Uani 1 d . . H18A H -0.5541(8) 0.0950(4) -0.1134(15) 0.207 Uiso 1 calc R . H18B H -0.6561(8) 0.1358(4) -0.0866(15) 0.207 Uiso 1 calc R . H18C H -0.5566(8) 0.0980(4) 0.0464(15) 0.207 Uiso 1 calc R . C19 C -0.4671(10) 0.1953(5) 0.1245(12) 0.132(4) Uani 1 d . . H19A H -0.3935(10) 0.2223(5) 0.1593(12) 0.198 Uiso 1 calc R . H19B H -0.4605(10) 0.1743(5) 0.2100(12) 0.198 Uiso 1 calc R . H19C H -0.5600(10) 0.2121(5) 0.0770(12) 0.198 Uiso 1 calc R . C20 C -0.4639(11) 0.1933(5) -0.1266(12) 0.143(5) Uani 1 d . . H20A H -0.3893(11) 0.2199(5) -0.0948(12) 0.214 Uiso 1 calc R . H20B H -0.5562(11) 0.2106(5) -0.1690(12) 0.214 Uiso 1 calc R . H20C H -0.4565(11) 0.1706(5) -0.2026(12) 0.214 Uiso 1 calc R . C21 C 0.0965(6) 0.1876(2) 0.2793(7) 0.0488(14) Uani 1 d . . C22 C 0.1921(7) 0.1816(2) 0.1965(9) 0.070(2) Uani 1 d . . H22A H 0.2729(7) 0.2054(2) 0.2413(9) 0.106 Uiso 1 calc R . H22B H 0.1375(7) 0.1903(2) 0.0903(9) 0.106 Uiso 1 calc R . H22C H 0.2259(7) 0.1454(2) 0.2059(9) 0.106 Uiso 1 calc R . C23 C 0.1834(7) 0.1768(3) 0.4517(8) 0.068(2) Uani 1 d . . H23A H 0.1217(7) 0.1807(3) 0.5016(8) 0.102 Uiso 1 calc R . H23B H 0.2614(7) 0.2018(3) 0.4943(8) 0.102 Uiso 1 calc R . H23C H 0.2210(7) 0.1410(3) 0.4668(8) 0.102 Uiso 1 calc R . C24 C 0.0469(7) 0.2471(2) 0.2613(9) 0.077(2) Uani 1 d . . H24A H -0.0136(7) 0.2525(2) 0.3120(9) 0.115 Uiso 1 calc R . H24B H -0.0060(7) 0.2555(2) 0.1547(9) 0.115 Uiso 1 calc R . H24C H 0.1296(7) 0.2700(2) 0.3062(9) 0.115 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Al 0.0390(7) 0.0387(8) 0.0402(8) -0.0020(7) 0.0162(6) -0.0007(6) N1 0.068(3) 0.044(2) 0.047(3) 0.002(2) 0.027(3) 0.003(2) C2 0.072(4) 0.036(3) 0.065(4) -0.006(3) 0.032(3) 0.003(3) C3 0.059(3) 0.036(3) 0.062(4) -0.015(3) 0.015(3) -0.009(2) N4 0.049(2) 0.032(2) 0.047(3) -0.008(2) 0.018(2) -0.005(2) C5 0.037(2) 0.046(3) 0.041(3) -0.002(2) 0.013(2) -0.007(2) C6 0.043(3) 0.039(3) 0.038(3) 0.000(2) 0.016(2) 0.000(2) C7 0.045(3) 0.053(3) 0.046(3) 0.006(3) 0.016(3) 0.001(2) C8 0.044(3) 0.059(3) 0.041(3) 0.006(3) 0.020(2) 0.008(2) C9 0.062(3) 0.039(3) 0.052(3) 0.003(3) 0.026(3) 0.010(2) C10 0.051(3) 0.035(3) 0.042(3) -0.003(2) 0.024(2) 0.003(2) C11 0.040(3) 0.039(3) 0.035(3) 0.002(2) 0.017(2) 0.001(2) O12 0.037(2) 0.035(2) 0.063(2) 0.002(2) 0.015(2) -0.0040(14) C13 0.066(3) 0.057(3) 0.048(3) -0.003(3) 0.023(3) 0.004(3) C14 0.052(3) 0.056(3) 0.049(3) 0.002(3) 0.024(2) -0.004(2) C15 0.065(4) 0.065(4) 0.105(7) 0.011(4) 0.020(4) 0.017(3) C16 0.121(6) 0.052(4) 0.060(4) 0.007(3) 0.048(4) -0.010(3) C17 0.047(3) 0.074(4) 0.059(4) 0.005(3) 0.023(3) 0.021(3) C18 0.046(4) 0.118(7) 0.211(13) 0.014(8) 0.020(6) 0.014(4) C19 0.092(6) 0.166(10) 0.125(9) -0.025(7) 0.035(6) 0.066(7) C20 0.108(7) 0.209(12) 0.104(8) 0.081(8) 0.039(6) 0.084(8) C21 0.057(3) 0.037(3) 0.055(4) -0.003(2) 0.026(3) -0.004(2) C22 0.068(4) 0.055(4) 0.095(5) -0.011(3) 0.042(4) -0.023(3) C23 0.066(4) 0.060(4) 0.065(4) -0.010(3) 0.017(3) -0.015(3) C24 0.079(4) 0.038(3) 0.107(6) -0.004(3) 0.035(4) -0.005(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 Al O12 1.854(4) . ? Al C14 1.976(5) . ? Al C13 1.978(6) . ? Al N4 1.998(4) . ? Al N1 2.413(5) . ? N1 C16 1.453(8) . ? N1 C2 1.463(8) . ? N1 C15 1.466(8) . ? C2 C3 1.502(8) . ? C3 N4 1.488(7) . ? N4 C5 1.294(6) . ? C5 C6 1.434(7) . ? C6 C7 1.399(7) . ? C6 C11 1.409(7) . ? C7 C8 1.392(8) . ? C8 C9 1.410(8) . ? C8 C17 1.521(8) . ? C9 C10 1.368(8) . ? C10 C11 1.433(7) . ? C10 C21 1.538(7) . ? C11 O12 1.310(6) . ? C17 C18 1.495(11) . ? C17 C19 1.504(11) . ? C17 C20 1.522(11) . ? C21 C22 1.531(9) . ? C21 C23 1.541(9) . ? C21 C24 1.556(8) . ? 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 O12 Al C14 96.6(2) . . ? O12 Al C13 98.3(2) . . ? C14 Al C13 123.7(3) . . ? O12 Al N4 88.2(2) . . ? C14 Al N4 116.0(2) . . ? C13 Al N4 118.4(2) . . ? O12 Al N1 163.0(2) . . ? C14 Al N1 91.4(2) . . ? C13 Al N1 89.5(2) . . ? N4 Al N1 74.9(2) . . ? C16 N1 C2 110.2(5) . . ? C16 N1 C15 110.0(6) . . ? C2 N1 C15 109.5(5) . . ? C16 N1 Al 112.7(4) . . ? C2 N1 Al 99.6(3) . . ? C15 N1 Al 114.3(4) . . ? N1 C2 C3 110.0(5) . . ? N4 C3 C2 109.1(4) . . ? C5 N4 C3 115.4(4) . . ? C5 N4 Al 123.5(3) . . ? C3 N4 Al 120.8(3) . . ? N4 C5 C6 127.2(4) . . ? C7 C6 C11 121.6(5) . . ? C7 C6 C5 117.3(5) . . ? C11 C6 C5 121.1(4) . . ? C8 C7 C6 121.4(5) . . ? C7 C8 C9 115.4(5) . . ? C7 C8 C17 123.4(5) . . ? C9 C8 C17 121.2(5) . . ? C10 C9 C8 126.0(5) . . ? C9 C10 C11 117.6(5) . . ? C9 C10 C21 123.1(5) . . ? C11 C10 C21 119.2(4) . . ? O12 C11 C6 120.7(4) . . ? O12 C11 C10 121.3(4) . . ? C6 C11 C10 118.0(4) . . ? C11 O12 Al 132.1(3) . . ? C18 C17 C19 107.6(8) . . ? C18 C17 C8 112.7(6) . . ? C19 C17 C8 110.4(6) . . ? C18 C17 C20 109.0(8) . . ? C19 C17 C20 108.7(8) . . ? C8 C17 C20 108.3(6) . . ? C22 C21 C10 110.6(5) . . ? C22 C21 C23 110.7(5) . . ? C10 C21 C23 110.6(5) . . ? C22 C21 C24 106.9(5) . . ? C10 C21 C24 110.7(5) . . ? C23 C21 C24 107.2(5) . . ? _refine_diff_density_max 0.260 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.053 data_VG9923 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C23 H33 N2 O Al' _chemical_formula_weight 380.49 _chemical_melting_point ? _chemical_compound_source ? 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 15.009(2) _cell_length_b 12.2073(15) _cell_length_c 14.1285(13) _cell_angle_alpha 90.00 _cell_angle_beta 116.357(6) _cell_angle_gamma 90.00 _cell_volume 2319.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 4.66 _cell_measurement_theta_max 12.98 _exptl_crystal_description prisms _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.93 _exptl_crystal_size_mid 0.90 _exptl_crystal_size_min 0.80 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.090 _exptl_crystal_density_method ? _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.56 _diffrn_reflns_number 5517 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5299 _reflns_number_observed 3526 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 551 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0126(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4748 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_obs 0.0539 _refine_ls_wR_factor_all 0.1630 _refine_ls_wR_factor_obs 0.1364 _refine_ls_goodness_of_fit_all 1.014 _refine_ls_goodness_of_fit_obs 1.069 _refine_ls_restrained_S_all 1.033 _refine_ls_restrained_S_obs 1.069 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Al Al 0.38994(4) 0.79064(5) 0.04803(5) 0.0415(2) Uani 1 d . . N1 N 0.26970(15) 0.8752(2) 0.0751(2) 0.0570(5) Uani 1 d . . C2 C 0.1897(2) 0.8268(3) 0.0751(3) 0.0867(10) Uani 1 d . . H2A H 0.1820(2) 0.7515(3) 0.0644(3) 0.104 Uiso 1 calc R . C3 C 0.1184(3) 0.8843(4) 0.0904(4) 0.1011(13) Uani 1 d . . H3A H 0.0635(3) 0.8485(4) 0.0900(4) 0.121 Uiso 1 calc R . C4 C 0.1294(2) 0.9947(4) 0.1063(3) 0.0907(11) Uani 1 d . . H4A H 0.0819(2) 1.0351(4) 0.1167(3) 0.109 Uiso 1 calc R . C5 C 0.2109(2) 1.0458(3) 0.1069(2) 0.0691(7) Uani 1 d . . H5A H 0.2196(2) 1.1210(3) 0.1175(2) 0.083 Uiso 1 calc R . C6 C 0.2805(2) 0.9825(2) 0.0910(2) 0.0500(5) Uani 1 d . . C7 C 0.3706(2) 1.0305(2) 0.0879(2) 0.0545(5) Uani 1 d . . H7A H 0.3515(2) 1.0712(2) 0.0228(2) 0.065 Uiso 1 calc R . H7B H 0.4029(2) 1.0807(2) 0.1466(2) 0.065 Uiso 1 calc R . N8 N 0.43993(13) 0.94261(14) 0.09449(14) 0.0422(4) Uani 1 d . . C9 C 0.5334(2) 0.9679(2) 0.1402(2) 0.0440(4) Uani 1 d . . H9A H 0.5496(2) 1.0380(2) 0.1684(2) 0.053 Uiso 1 calc R . C10 C 0.61461(15) 0.8982(2) 0.1515(2) 0.0428(4) Uani 1 d . . C11 C 0.7113(2) 0.9384(2) 0.2127(2) 0.0480(5) Uani 1 d . . H11A H 0.7197(2) 1.0048(2) 0.2479(2) 0.058 Uiso 1 calc R . C12 C 0.7935(2) 0.8814(2) 0.2214(2) 0.0505(5) Uani 1 d . . C13 C 0.7757(2) 0.7819(2) 0.1646(2) 0.0519(5) Uani 1 d . . H13A H 0.8308(2) 0.7430(2) 0.1693(2) 0.062 Uiso 1 calc R . C14 C 0.6831(2) 0.7380(2) 0.1027(2) 0.0468(5) Uani 1 d . . C15 C 0.59805(14) 0.7971(2) 0.0967(2) 0.0415(4) Uani 1 d . . O16 O 0.50730(10) 0.76216(13) 0.03910(13) 0.0477(4) Uani 1 d . . C17 C 0.4077(2) 0.6869(2) 0.1629(2) 0.0625(6) Uani 1 d . . H17A H 0.4574(2) 0.7146(2) 0.2288(2) 0.094 Uiso 1 calc R . H17B H 0.4283(2) 0.6170(2) 0.1485(2) 0.094 Uiso 1 calc R . H17C H 0.3458(2) 0.6788(2) 0.1670(2) 0.094 Uiso 1 calc R . C18 C 0.2951(2) 0.7673(2) -0.1015(2) 0.0605(6) Uani 1 d . . H18A H 0.2990(2) 0.8276(2) -0.1431(2) 0.091 Uiso 1 calc R . H18B H 0.2288(2) 0.7624(2) -0.1078(2) 0.091 Uiso 1 calc R . H18C H 0.3113(2) 0.7006(2) -0.1262(2) 0.091 Uiso 1 calc R . C19 C 0.9002(2) 0.9222(3) 0.2863(2) 0.0662(7) Uani 1 d . . C20 C 0.9045(2) 1.0265(3) 0.3482(3) 0.0844(10) Uani 1 d . . H20A H 0.8771(2) 1.0121(3) 0.3967(3) 0.127 Uiso 1 calc R . H20B H 0.8668(2) 1.0833(3) 0.3000(3) 0.127 Uiso 1 calc R . H20C H 0.9724(2) 1.0496(3) 0.3867(3) 0.127 Uiso 1 calc R . C21 C 0.9443(3) 0.9489(6) 0.2110(4) 0.138(2) Uani 1 d . . H21A H 0.9043(3) 1.0037(6) 0.1616(4) 0.207 Uiso 1 calc R . H21B H 0.9456(3) 0.8839(6) 0.1734(4) 0.207 Uiso 1 calc R . H21C H 1.0107(3) 0.9761(6) 0.2503(4) 0.207 Uiso 1 calc R . C22 C 0.9609(3) 0.8353(4) 0.3668(4) 0.118(2) Uani 1 d . . H22A H 0.9310(3) 0.8205(4) 0.4131(4) 0.178 Uiso 1 calc R . H22B H 1.0275(3) 0.8615(4) 0.4075(4) 0.178 Uiso 1 calc R . H22C H 0.9624(3) 0.7693(4) 0.3306(4) 0.178 Uiso 1 calc R . C23 C 0.6702(2) 0.6288(2) 0.0438(2) 0.0561(6) Uani 1 d . . C24 C 0.7707(2) 0.5818(3) 0.0573(3) 0.0907(11) Uani 1 d . . H24A H 0.8019(2) 0.6329(3) 0.0299(3) 0.136 Uiso 1 calc R . H24B H 0.7596(2) 0.5138(3) 0.0196(3) 0.136 Uiso 1 calc R . H24C H 0.8130(2) 0.5693(3) 0.1310(3) 0.136 Uiso 1 calc R . C25 C 0.6238(2) 0.5447(2) 0.0884(3) 0.0698(7) Uani 1 d . . H25A H 0.6157(2) 0.4764(2) 0.0517(3) 0.105 Uiso 1 calc R . H25B H 0.5601(2) 0.5706(2) 0.0792(3) 0.105 Uiso 1 calc R . H25C H 0.6664(2) 0.5341(2) 0.1622(3) 0.105 Uiso 1 calc R . C26 C 0.6037(2) 0.6451(3) -0.0755(2) 0.0710(8) Uani 1 d . . H26A H 0.6336(2) 0.6981(3) -0.1027(2) 0.107 Uiso 1 calc R . H26B H 0.5394(2) 0.6706(3) -0.0863(2) 0.107 Uiso 1 calc R . H26C H 0.5967(2) 0.5767(3) -0.1116(2) 0.107 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Al 0.0385(3) 0.0397(3) 0.0430(3) 0.0012(3) 0.0151(2) -0.0032(2) N1 0.0460(9) 0.0625(12) 0.0677(12) -0.0009(10) 0.0300(9) -0.0025(9) C2 0.060(2) 0.085(2) 0.127(3) -0.003(2) 0.052(2) -0.0114(15) C3 0.059(2) 0.125(3) 0.137(4) -0.003(3) 0.060(2) -0.009(2) C4 0.061(2) 0.126(3) 0.104(3) -0.005(2) 0.053(2) 0.015(2) C5 0.0585(14) 0.081(2) 0.073(2) -0.0031(14) 0.0347(13) 0.0171(13) C6 0.0435(10) 0.0628(13) 0.0437(10) 0.0021(9) 0.0196(8) 0.0072(9) C7 0.0521(12) 0.0445(11) 0.0745(15) 0.0003(10) 0.0348(11) 0.0057(9) N8 0.0422(8) 0.0398(8) 0.0493(9) -0.0016(7) 0.0245(7) 0.0005(7) C9 0.0466(10) 0.0410(10) 0.0489(11) -0.0093(8) 0.0254(9) -0.0053(8) C10 0.0410(9) 0.0461(10) 0.0427(9) -0.0064(8) 0.0198(8) -0.0040(8) C11 0.0459(10) 0.0520(11) 0.0463(10) -0.0111(9) 0.0206(9) -0.0089(9) C12 0.0395(10) 0.0619(13) 0.0466(11) -0.0051(10) 0.0160(8) -0.0069(9) C13 0.0392(9) 0.0608(13) 0.0544(12) -0.0020(10) 0.0198(9) 0.0049(9) C14 0.0433(10) 0.0463(11) 0.0498(11) -0.0038(8) 0.0198(9) 0.0032(8) C15 0.0393(9) 0.0412(9) 0.0439(9) -0.0033(8) 0.0185(7) -0.0027(8) O16 0.0377(7) 0.0445(8) 0.0566(9) -0.0130(6) 0.0170(6) -0.0033(6) C17 0.078(2) 0.0547(14) 0.0561(13) 0.0098(11) 0.0314(12) 0.0013(12) C18 0.0535(12) 0.064(2) 0.0504(12) -0.0006(11) 0.0110(10) 0.0007(11) C19 0.0393(11) 0.088(2) 0.0602(14) -0.0131(13) 0.0121(10) -0.0101(12) C20 0.060(2) 0.092(2) 0.077(2) -0.024(2) 0.0093(14) -0.021(2) C21 0.079(2) 0.245(7) 0.106(3) -0.058(4) 0.055(2) -0.083(3) C22 0.066(2) 0.111(3) 0.115(3) -0.009(3) -0.017(2) 0.012(2) C23 0.0509(12) 0.0488(12) 0.0644(14) -0.0098(10) 0.0216(10) 0.0082(9) C24 0.066(2) 0.076(2) 0.124(3) -0.032(2) 0.038(2) 0.0152(15) C25 0.074(2) 0.0469(13) 0.075(2) -0.0037(12) 0.0218(14) 0.0014(12) C26 0.089(2) 0.063(2) 0.0587(15) -0.0124(12) 0.0309(14) 0.0104(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al O16 1.854(2) . ? Al C18 1.975(2) . ? Al C17 1.982(3) . ? Al N8 1.999(2) . ? Al N1 2.254(2) . ? N1 C6 1.326(3) . ? N1 C2 1.339(4) . ? C2 C3 1.375(5) . ? C3 C4 1.364(6) . ? C4 C5 1.370(5) . ? C5 C6 1.396(3) . ? C6 C7 1.493(3) . ? C7 N8 1.468(3) . ? N8 C9 1.295(3) . ? C9 C10 1.436(3) . ? C10 C11 1.408(3) . ? C10 C15 1.418(3) . ? C11 C12 1.373(3) . ? C12 C13 1.415(3) . ? C12 C19 1.533(3) . ? C13 C14 1.381(3) . ? C14 C15 1.435(3) . ? C14 C23 1.539(3) . ? C15 O16 1.310(2) . ? C19 C21 1.517(5) . ? C19 C22 1.526(5) . ? C19 C20 1.529(5) . ? C23 C25 1.525(4) . ? C23 C24 1.543(4) . ? C23 C26 1.543(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 O16 Al C18 98.97(10) . . ? O16 Al C17 98.61(11) . . ? C18 Al C17 123.69(12) . . ? O16 Al N8 88.11(7) . . ? C18 Al N8 118.18(10) . . ? C17 Al N8 115.47(10) . . ? O16 Al N1 162.52(8) . . ? C18 Al N1 89.78(10) . . ? C17 Al N1 88.87(11) . . ? N8 Al N1 74.41(8) . . ? C6 N1 C2 118.6(3) . . ? C6 N1 Al 115.7(2) . . ? C2 N1 Al 125.7(2) . . ? N1 C2 C3 122.4(4) . . ? C4 C3 C2 119.0(3) . . ? C3 C4 C5 119.6(3) . . ? C4 C5 C6 118.5(3) . . ? N1 C6 C5 122.0(2) . . ? N1 C6 C7 115.3(2) . . ? C5 C6 C7 122.7(3) . . ? N8 C7 C6 109.7(2) . . ? C9 N8 C7 116.0(2) . . ? C9 N8 Al 123.39(14) . . ? C7 N8 Al 120.35(14) . . ? N8 C9 C10 126.3(2) . . ? C11 C10 C15 121.5(2) . . ? C11 C10 C9 117.0(2) . . ? C15 C10 C9 121.4(2) . . ? C12 C11 C10 121.2(2) . . ? C11 C12 C13 116.7(2) . . ? C11 C12 C19 123.2(2) . . ? C13 C12 C19 120.1(2) . . ? C14 C13 C12 125.1(2) . . ? C13 C14 C15 117.5(2) . . ? C13 C14 C23 121.9(2) . . ? C15 C14 C23 120.6(2) . . ? O16 C15 C10 120.3(2) . . ? O16 C15 C14 121.7(2) . . ? C10 C15 C14 118.0(2) . . ? C15 O16 Al 130.85(14) . . ? C21 C19 C22 111.8(4) . . ? C21 C19 C20 107.5(3) . . ? C22 C19 C20 107.0(3) . . ? C21 C19 C12 108.4(2) . . ? C22 C19 C12 109.8(3) . . ? C20 C19 C12 112.3(2) . . ? C25 C23 C14 109.3(2) . . ? C25 C23 C24 107.4(2) . . ? C14 C23 C24 112.0(2) . . ? C25 C23 C26 110.2(2) . . ? C14 C23 C26 110.1(2) . . ? C24 C23 C26 107.9(3) . . ? _refine_diff_density_max 0.229 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.044