# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name D.S.Wright _publ_contact_author_name 'Dominic S.Wright' data_dw1065 _database_code_depnum_ccdc_archive 'CCDC 803522' #TrackingRef '- DW1065.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H29 Al B2 N4' _chemical_formula_sum 'C8 H29 Al B2 N4' _chemical_formula_weight 229.95 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' B B 0.0013 0.0007 '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 Pnn2 _symmetry_space_group_name_Hall P2-2n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 10.1260(5) _cell_length_b 11.6705(6) _cell_length_c 6.4209(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 758.79(6) _cell_formula_units_Z 2 _cell_measurement_temperature 250(2) _cell_measurement_reflns_used 3254 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.10 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.006 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.788 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 250(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_reflns_number 3182 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 27.06 _reflns_number_total 1490 _reflns_number_gt 1297 _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 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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 structure was solved and refinec in the polar space group Pnn2. The determination of the absolute structure via the Flack parameter is unreliable for light atom structures. As a consequence the Friedel pairs were merged. In the latter stages of refinement residual electron density (> 2e-) indicated some disorder of the Al. The sof's were refined using a common Uiso and then fixed. The thermal parameters were then refined anisotropically but constrained to share common parameters (EADP). H atoms were added at calculated positions and refined with a riding model for those bound to C and B. The H atoms bound to Al were constrained to lie on the special positions (0,0,z) and the Al-H bond length restrained (DFIX). ; _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^)+(0.1278P)^2^+0.0446P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(9) _refine_ls_number_reflns 1490 _refine_ls_number_parameters 80 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0627 _refine_ls_R_factor_gt 0.0574 _refine_ls_wR_factor_ref 0.1710 _refine_ls_wR_factor_gt 0.1662 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.061 _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 Al1A Al 0.0000 0.0000 0.36251(13) 0.0331(3) Uani 0.89 2 d SPD . 1 H1A H 0.0000 0.0000 0.590(7) 0.050 Uiso 0.89 1 d PD A 1 Al1B Al 0.0000 0.0000 0.2049(17) 0.0331(3) Uani 0.11 2 d SPD . 2 H1B H 0.0000 0.0000 -0.028(8) 0.050 Uiso 0.11 1 d PD B 2 B1 B 0.1696(3) 0.15453(19) 0.3205(6) 0.0535(7) Uani 1 1 d . . . H1C H 0.1812 0.1898 0.4577 0.064 Uiso 1 1 calc R . . H1D H 0.2254 0.1944 0.2189 0.064 Uiso 1 1 calc R . . N1 N 0.02069(19) 0.15524(17) 0.2519(4) 0.0480(6) Uani 1 1 d . . . C11 C -0.0569(3) 0.24503(19) 0.3476(8) 0.0719(9) Uani 1 1 d . . . H11A H -0.0184 0.3189 0.3148 0.108 Uiso 1 1 calc R . . H11B H -0.0578 0.2343 0.4974 0.108 Uiso 1 1 calc R . . H11C H -0.1466 0.2420 0.2947 0.108 Uiso 1 1 calc R . . C12 C 0.0097(3) 0.1710(3) 0.0180(6) 0.0680(9) Uani 1 1 d . . . H12A H -0.0820 0.1639 -0.0238 0.102 Uiso 1 1 calc R . . H12B H 0.0619 0.1128 -0.0519 0.102 Uiso 1 1 calc R . . H12C H 0.0423 0.2463 -0.0199 0.102 Uiso 1 1 calc R . . N2 N 0.20125(18) 0.02187(16) 0.3267(5) 0.0520(7) Uani 1 1 d . . . C21 C 0.2785(4) -0.0116(4) 0.5108(9) 0.0834(14) Uani 1 1 d . . . H21A H 0.2922 -0.0938 0.5097 0.125 Uiso 1 1 calc R . . H21B H 0.2310 0.0099 0.6360 0.125 Uiso 1 1 calc R . . H21C H 0.3633 0.0271 0.5081 0.125 Uiso 1 1 calc R . . C22 C 0.2706(4) -0.0163(4) 0.1416(9) 0.0808(13) Uani 1 1 d . . . H22A H 0.3562 0.0208 0.1346 0.121 Uiso 1 1 calc R . . H22B H 0.2195 0.0035 0.0190 0.121 Uiso 1 1 calc R . . H22C H 0.2825 -0.0987 0.1474 0.121 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 Al1A 0.0364(5) 0.0322(5) 0.0308(5) 0.000 0.000 -0.0007(3) Al1B 0.0364(5) 0.0322(5) 0.0308(5) 0.000 0.000 -0.0007(3) B1 0.0465(13) 0.0412(11) 0.073(2) -0.0047(15) -0.0030(12) -0.0086(9) N1 0.0473(9) 0.0305(9) 0.0662(17) -0.0002(9) 0.0047(11) -0.0008(7) C11 0.0640(16) 0.0437(11) 0.108(3) -0.0142(18) -0.0027(18) 0.0123(11) C12 0.086(2) 0.068(2) 0.0503(18) 0.0162(16) -0.0047(14) -0.0096(13) N2 0.0363(9) 0.0457(8) 0.0741(19) 0.0007(12) -0.0028(10) -0.0009(7) C21 0.0573(19) 0.073(2) 0.120(4) 0.006(2) -0.030(2) 0.0070(16) C22 0.0560(18) 0.0651(17) 0.121(4) -0.018(2) 0.0294(19) -0.0022(16) _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 Al1A N1 1.957(2) 2 ? Al1A N1 1.957(2) . ? Al1A N2 2.0666(18) . ? Al1A N2 2.0666(18) 2 ? Al1A H1A 1.46(4) . ? Al1B N1 1.849(3) 2 ? Al1B N1 1.849(3) . ? Al1B N2 2.198(5) . ? Al1B N2 2.198(5) 2 ? Al1B C12 2.331(7) 2 ? Al1B H1B 1.50(5) . ? B1 N1 1.571(3) . ? B1 N2 1.582(3) . ? B1 H1C 0.9800 . ? B1 H1D 0.9800 . ? N1 C11 1.447(3) . ? N1 C12 1.517(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12 H12C 0.9700 . ? N2 C22 1.451(5) . ? N2 C21 1.470(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? 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 Al1A N1 137.45(16) 2 . ? N1 Al1A N2 100.34(9) 2 . ? N1 Al1A N2 74.92(8) . . ? N1 Al1A N2 74.92(8) 2 2 ? N1 Al1A N2 100.34(9) . 2 ? N2 Al1A N2 167.23(18) . 2 ? N1 Al1A H1A 111.27(8) 2 . ? N1 Al1A H1A 111.27(8) . . ? N2 Al1A H1A 96.38(9) . . ? N2 Al1A H1A 96.38(9) 2 . ? N1 Al1B N1 161.2(7) 2 . ? N1 Al1B N2 99.3(2) 2 . ? N1 Al1B N2 73.92(15) . . ? N1 Al1B N2 73.92(15) 2 2 ? N1 Al1B N2 99.2(2) . 2 ? N2 Al1B N2 138.3(6) . 2 ? N1 Al1B C12 40.55(18) 2 2 ? N1 Al1B C12 158.1(6) . 2 ? N2 Al1B C12 108.78(12) . 2 ? N2 Al1B C12 92.56(11) 2 2 ? N1 Al1B H1B 99.4(4) 2 . ? N1 Al1B H1B 99.4(4) . . ? N2 Al1B H1B 110.9(3) . . ? N2 Al1B H1B 110.9(3) 2 . ? C12 Al1B H1B 59.0(2) 2 . ? N1 B1 N2 101.94(16) . . ? N1 B1 H1C 111.4 . . ? N2 B1 H1C 111.4 . . ? N1 B1 H1D 111.4 . . ? N2 B1 H1D 111.4 . . ? H1C B1 H1D 109.2 . . ? C11 N1 C12 107.0(3) . . ? C11 N1 B1 114.0(2) . . ? C12 N1 B1 110.4(2) . . ? C11 N1 Al1B 135.9(2) . . ? C12 N1 Al1B 87.1(4) . . ? B1 N1 Al1B 98.59(16) . . ? C11 N1 Al1A 117.28(19) . . ? C12 N1 Al1A 117.6(2) . . ? B1 N1 Al1A 89.79(13) . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N1 C12 H12A 109.5 . . ? N1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C22 N2 C21 108.6(3) . . ? C22 N2 B1 112.2(3) . . ? C21 N2 B1 112.9(3) . . ? C22 N2 Al1A 122.0(2) . . ? C21 N2 Al1A 113.7(3) . . ? B1 N2 Al1A 85.63(13) . . ? C22 N2 Al1B 97.0(4) . . ? C21 N2 Al1B 138.5(4) . . ? B1 N2 Al1B 85.22(13) . . ? N2 C21 H21A 109.5 . . ? N2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N2 C22 H22A 109.5 . . ? N2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.417 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.052