# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_d21 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H32 Al N O' _chemical_formula_weight 389.50 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 9.8106(8) _cell_length_b 14.5843(12) _cell_length_c 17.0062(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.4090(10) _cell_angle_gamma 90.00 _cell_volume 2356.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 3062 _cell_measurement_theta_min 2.5583 _cell_measurement_theta_max 25.5872 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.098 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(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 'Bruker APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13004 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 26.03 _reflns_number_total 4614 _reflns_number_gt 3521 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0574P)^2^+0.7254P] 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 4614 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0700 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.23132(6) 0.14643(4) 0.23980(3) 0.03009(16) Uani 1 1 d . . . O1 O 0.36383(12) 0.15792(9) 0.33399(7) 0.0325(3) Uani 1 1 d . . . N1 N 0.33103(15) 0.22457(10) 0.18081(9) 0.0288(3) Uani 1 1 d . . . C11 C 0.49639(18) 0.18100(12) 0.34547(11) 0.0280(4) Uani 1 1 d . . . C3 C 0.46639(18) 0.24066(12) 0.20837(11) 0.0297(4) Uani 1 1 d . . . H3 H 0.5111 0.2724 0.1729 0.036 Uiso 1 1 calc R . . C13 C 0.5395(2) 0.11789(13) 0.48562(11) 0.0339(4) Uani 1 1 d . . . H13 H 0.4486 0.0908 0.4715 0.041 Uiso 1 1 calc R . . C4 C 0.26185(18) 0.27600(13) 0.10868(11) 0.0305(4) Uani 1 1 d . . . C10 C 0.55229(19) 0.21601(13) 0.28477(11) 0.0309(4) Uani 1 1 d . . . C12 C 0.58625(18) 0.16883(12) 0.42815(11) 0.0299(4) Uani 1 1 d . . . C5 C 0.22427(19) 0.36741(13) 0.11934(12) 0.0341(4) Uani 1 1 d . . . C9 C 0.2361(2) 0.23492(14) 0.03221(12) 0.0361(5) Uani 1 1 d . . . C17 C 0.7199(2) 0.21016(14) 0.44945(12) 0.0369(5) Uani 1 1 d . . . C6 C 0.1647(2) 0.41817(15) 0.04966(13) 0.0448(5) Uani 1 1 d . . . H6 H 0.1400 0.4805 0.0548 0.054 Uiso 1 1 calc R . . C8 C 0.1746(2) 0.28882(17) -0.03494(13) 0.0453(5) Uani 1 1 d . . . H8 H 0.1553 0.2626 -0.0877 0.054 Uiso 1 1 calc R . . C15 C 0.7564(2) 0.14643(16) 0.58392(13) 0.0473(6) Uani 1 1 d . . . H15 H 0.8151 0.1385 0.6371 0.057 Uiso 1 1 calc R . . C7 C 0.1413(2) 0.37955(17) -0.02619(14) 0.0494(6) Uani 1 1 d . . . H7 H 0.1019 0.4155 -0.0729 0.059 Uiso 1 1 calc R . . C16 C 0.8033(2) 0.19803(16) 0.52756(13) 0.0474(6) Uani 1 1 d . . . H16 H 0.8938 0.2255 0.5426 0.057 Uiso 1 1 calc R . . C2 C 0.2205(2) 0.01813(15) 0.20453(14) 0.0458(5) Uani 1 1 d . . . H2A H 0.3092 0.0005 0.1920 0.069 Uiso 1 1 calc R . . H2B H 0.1430 0.0108 0.1559 0.069 Uiso 1 1 calc R . . H2C H 0.2040 -0.0211 0.2480 0.069 Uiso 1 1 calc R . . C1 C 0.0509(2) 0.20310(16) 0.24110(13) 0.0428(5) Uani 1 1 d . . . H1A H 0.0066 0.1684 0.2775 0.064 Uiso 1 1 calc R . . H1B H -0.0109 0.2027 0.1861 0.064 Uiso 1 1 calc R . . H1C H 0.0667 0.2665 0.2604 0.064 Uiso 1 1 calc R . . C20 C 0.2500(2) 0.41078(14) 0.20311(13) 0.0385(5) Uani 1 1 d . . . H20 H 0.2628 0.3600 0.2438 0.046 Uiso 1 1 calc R . . C19 C 0.7088(2) 0.23475(16) 0.30281(13) 0.0435(5) Uani 1 1 d . . . H19A H 0.7587 0.1776 0.2956 0.052 Uiso 1 1 calc R . . H19B H 0.7272 0.2807 0.2638 0.052 Uiso 1 1 calc R . . C14 C 0.6246(2) 0.10643(15) 0.56317(12) 0.0404(5) Uani 1 1 d . . . H14 H 0.5925 0.0712 0.6020 0.048 Uiso 1 1 calc R . . C18 C 0.7652(2) 0.26995(16) 0.38834(13) 0.0493(6) Uani 1 1 d . . . H18A H 0.8692 0.2719 0.4011 0.059 Uiso 1 1 calc R . . H18B H 0.7308 0.3332 0.3922 0.059 Uiso 1 1 calc R . . C23 C 0.2773(2) 0.13647(15) 0.02066(13) 0.0461(5) Uani 1 1 d . . . H23 H 0.3099 0.1081 0.0757 0.055 Uiso 1 1 calc R . . C21 C 0.3847(2) 0.46798(17) 0.22262(15) 0.0533(6) Uani 1 1 d . . . H21A H 0.4652 0.4286 0.2217 0.080 Uiso 1 1 calc R . . H21B H 0.3981 0.4954 0.2766 0.080 Uiso 1 1 calc R . . H21C H 0.3772 0.5167 0.1820 0.080 Uiso 1 1 calc R . . C24 C 0.4003(4) 0.13327(19) -0.0197(2) 0.0875(11) Uani 1 1 d . . . H24A H 0.3727 0.1632 -0.0729 0.131 Uiso 1 1 calc R . . H24B H 0.4255 0.0693 -0.0266 0.131 Uiso 1 1 calc R . . H24C H 0.4814 0.1653 0.0145 0.131 Uiso 1 1 calc R . . C22 C 0.1260(2) 0.46910(17) 0.21302(16) 0.0588(7) Uani 1 1 d . . . H22A H 0.1152 0.5222 0.1766 0.088 Uiso 1 1 calc R . . H22B H 0.1434 0.4903 0.2693 0.088 Uiso 1 1 calc R . . H22C H 0.0398 0.4323 0.1995 0.088 Uiso 1 1 calc R . . C25 C 0.1530(3) 0.0801(2) -0.02717(19) 0.0866(10) Uani 1 1 d . . . H25A H 0.0767 0.0819 0.0006 0.130 Uiso 1 1 calc R . . H25B H 0.1828 0.0165 -0.0310 0.130 Uiso 1 1 calc R . . H25C H 0.1198 0.1058 -0.0819 0.130 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 0.0248(3) 0.0351(3) 0.0294(3) 0.0059(2) 0.0049(2) -0.0020(2) O1 0.0240(6) 0.0438(8) 0.0288(7) 0.0049(6) 0.0051(5) -0.0042(6) N1 0.0282(8) 0.0299(8) 0.0280(8) 0.0039(6) 0.0064(6) 0.0006(6) C11 0.0248(9) 0.0255(9) 0.0330(10) 0.0009(8) 0.0060(8) 0.0036(7) C3 0.0300(10) 0.0284(10) 0.0337(10) 0.0049(8) 0.0133(8) 0.0013(7) C13 0.0324(10) 0.0354(11) 0.0328(11) -0.0001(8) 0.0063(8) 0.0011(8) C4 0.0241(9) 0.0373(11) 0.0299(10) 0.0077(8) 0.0062(8) -0.0024(8) C10 0.0265(9) 0.0314(10) 0.0349(11) 0.0063(8) 0.0080(8) 0.0033(8) C12 0.0282(9) 0.0290(10) 0.0318(10) 0.0007(8) 0.0060(8) 0.0050(7) C5 0.0303(10) 0.0345(11) 0.0374(11) 0.0074(9) 0.0086(8) 0.0023(8) C9 0.0338(11) 0.0426(12) 0.0327(11) 0.0036(9) 0.0097(9) -0.0055(9) C17 0.0283(10) 0.0397(11) 0.0392(11) 0.0017(9) 0.0018(9) 0.0003(8) C6 0.0425(12) 0.0434(13) 0.0490(14) 0.0152(10) 0.0123(10) 0.0111(10) C8 0.0409(12) 0.0650(16) 0.0280(11) 0.0051(10) 0.0047(9) -0.0023(11) C15 0.0416(12) 0.0625(15) 0.0310(11) 0.0009(10) -0.0037(9) 0.0074(11) C7 0.0410(12) 0.0645(16) 0.0400(13) 0.0218(11) 0.0050(10) 0.0099(11) C16 0.0334(11) 0.0569(14) 0.0459(13) 0.0005(11) -0.0016(10) -0.0048(10) C2 0.0464(13) 0.0403(12) 0.0479(13) 0.0041(10) 0.0065(10) -0.0081(10) C1 0.0295(11) 0.0572(14) 0.0416(12) 0.0102(10) 0.0086(9) 0.0004(9) C20 0.0404(11) 0.0312(11) 0.0446(12) 0.0013(9) 0.0116(9) 0.0027(9) C19 0.0274(10) 0.0536(14) 0.0498(13) 0.0169(11) 0.0099(9) -0.0012(9) C14 0.0437(12) 0.0452(12) 0.0319(11) 0.0032(9) 0.0085(9) 0.0057(9) C18 0.0300(11) 0.0557(15) 0.0560(15) 0.0130(11) -0.0008(10) -0.0130(10) C23 0.0621(15) 0.0412(13) 0.0372(12) -0.0023(10) 0.0164(11) -0.0067(11) C21 0.0509(14) 0.0469(14) 0.0614(15) -0.0066(11) 0.0126(12) -0.0063(11) C24 0.113(3) 0.0507(17) 0.124(3) 0.0074(17) 0.076(2) 0.0171(16) C22 0.0505(14) 0.0546(15) 0.0720(17) -0.0105(13) 0.0167(13) 0.0094(12) C25 0.107(3) 0.0650(19) 0.079(2) -0.0193(16) 0.0063(19) -0.0266(18) _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 1.8021(13) . ? Al1 N1 1.9366(15) . ? Al1 C1 1.958(2) . ? Al1 C2 1.960(2) . ? O1 C11 1.310(2) . ? N1 C3 1.315(2) . ? N1 C4 1.454(2) . ? C11 C10 1.382(2) . ? C11 C12 1.473(3) . ? C3 C10 1.408(2) . ? C3 H3 0.9500 . ? C13 C14 1.384(3) . ? C13 C12 1.393(3) . ? C13 H13 0.9500 . ? C4 C9 1.397(3) . ? C4 C5 1.407(3) . ? C10 C19 1.514(3) . ? C12 C17 1.406(3) . ? C5 C6 1.396(3) . ? C5 C20 1.521(3) . ? C9 C8 1.394(3) . ? C9 C23 1.518(3) . ? C17 C16 1.387(3) . ? C17 C18 1.506(3) . ? C6 C7 1.374(3) . ? C6 H6 0.9500 . ? C8 C7 1.380(3) . ? C8 H8 0.9500 . ? C15 C14 1.382(3) . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C7 H7 0.9500 . ? C16 H16 0.9500 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C20 C21 1.528(3) . ? C20 C22 1.528(3) . ? C20 H20 1.0000 . ? C19 C18 1.512(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C14 H14 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C23 C25 1.526(3) . ? C23 C24 1.531(3) . ? C23 H23 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 93.44(6) . . ? O1 Al1 C1 113.88(8) . . ? N1 Al1 C1 109.39(8) . . ? O1 Al1 C2 109.45(8) . . ? N1 Al1 C2 113.52(8) . . ? C1 Al1 C2 115.23(10) . . ? C11 O1 Al1 128.77(12) . . ? C3 N1 C4 115.26(15) . . ? C3 N1 Al1 121.07(12) . . ? C4 N1 Al1 123.42(11) . . ? O1 C11 C10 123.19(16) . . ? O1 C11 C12 116.58(15) . . ? C10 C11 C12 120.22(16) . . ? N1 C3 C10 127.07(16) . . ? N1 C3 H3 116.5 . . ? C10 C3 H3 116.5 . . ? C14 C13 C12 120.46(18) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C9 C4 C5 122.26(17) . . ? C9 C4 N1 120.19(17) . . ? C5 C4 N1 117.55(16) . . ? C11 C10 C3 121.75(16) . . ? C11 C10 C19 119.10(17) . . ? C3 C10 C19 119.00(16) . . ? C13 C12 C17 119.78(17) . . ? C13 C12 C11 120.71(16) . . ? C17 C12 C11 119.51(17) . . ? C6 C5 C4 117.45(19) . . ? C6 C5 C20 120.75(18) . . ? C4 C5 C20 121.79(17) . . ? C8 C9 C4 117.53(19) . . ? C8 C9 C23 120.16(19) . . ? C4 C9 C23 122.27(18) . . ? C16 C17 C12 118.81(19) . . ? C16 C17 C18 121.98(18) . . ? C12 C17 C18 119.13(17) . . ? C7 C6 C5 121.1(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C7 C8 C9 121.2(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C14 C15 C16 120.23(19) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C6 C7 C8 120.4(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C15 C16 C17 120.9(2) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C5 C20 C21 111.32(17) . . ? C5 C20 C22 112.54(18) . . ? C21 C20 C22 109.98(18) . . ? C5 C20 H20 107.6 . . ? C21 C20 H20 107.6 . . ? C22 C20 H20 107.6 . . ? C18 C19 C10 111.47(17) . . ? C18 C19 H19A 109.3 . . ? C10 C19 H19A 109.3 . . ? C18 C19 H19B 109.3 . . ? C10 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? C15 C14 C13 119.77(19) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C17 C18 C19 111.55(17) . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C9 C23 C25 112.0(2) . . ? C9 C23 C24 110.62(19) . . ? C25 C23 C24 111.0(2) . . ? C9 C23 H23 107.7 . . ? C25 C23 H23 107.7 . . ? C24 C23 H23 107.7 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.337 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.043 _database_code_depnum_ccdc_archive 'CCDC 946613' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_l _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 Al N O' _chemical_formula_weight 305.34 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1373(5) _cell_length_b 14.8039(8) _cell_length_c 14.8329(8) _cell_angle_alpha 117.5840(10) _cell_angle_beta 94.5200(10) _cell_angle_gamma 104.3280(10) _cell_volume 1678.77(16) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 1999 _cell_measurement_theta_min 2.3612 _cell_measurement_theta_max 23.9783 _exptl_crystal_description BLOCK _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9608 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(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 'Bruker APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9262 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.03 _reflns_number_total 6483 _reflns_number_gt 4590 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^+0.4660P] 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 6483 _refine_ls_number_parameters 401 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1200 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Al1 Al 0.75918(9) 0.59518(6) 0.25281(6) 0.0339(2) Uani 1 1 d . . . Al2 Al 0.71425(9) 0.04272(6) 0.26847(6) 0.0350(2) Uani 1 1 d . . . O1 O 0.62229(19) 0.50189(13) 0.27624(13) 0.0389(4) Uani 1 1 d . . . O2 O 0.7924(2) 0.08831(14) 0.18402(14) 0.0424(4) Uani 1 1 d . . . N2 N 0.5231(2) 0.07561(15) 0.25418(15) 0.0342(5) Uani 1 1 d . . . N1 N 0.9349(2) 0.55491(15) 0.28590(15) 0.0336(5) Uani 1 1 d . . . C3 C 0.9249(3) 0.49313(18) 0.32811(18) 0.0329(5) Uani 1 1 d . . . H3 H 1.0166 0.4784 0.3428 0.040 Uiso 1 1 calc R . . C4 C 1.0787(3) 0.58779(19) 0.25930(18) 0.0329(5) Uani 1 1 d . . . C10 C 0.7928(3) 0.44674(18) 0.35376(18) 0.0332(5) Uani 1 1 d . . . C11 C 0.6479(3) 0.45127(18) 0.32519(18) 0.0334(6) Uani 1 1 d . . . C12 C 0.5110(3) 0.39271(18) 0.34589(19) 0.0355(6) Uani 1 1 d . . . C23 C 0.4032(3) 0.04684(19) 0.3025(2) 0.0355(6) Uani 1 1 d . . . C30 C 0.7339(3) 0.12782(19) 0.13250(18) 0.0345(6) Uani 1 1 d . . . C29 C 0.5894(3) 0.14064(19) 0.13405(19) 0.0348(6) Uani 1 1 d . . . C22 C 0.4919(3) 0.11346(19) 0.19288(19) 0.0350(6) Uani 1 1 d . . . H22 H 0.3935 0.1235 0.1878 0.042 Uiso 1 1 calc R . . C19 C 0.8050(3) 0.3805(2) 0.40553(19) 0.0374(6) Uani 1 1 d . . . H19A H 0.9127 0.4057 0.4455 0.045 Uiso 1 1 calc R . . H19B H 0.7800 0.3041 0.3513 0.045 Uiso 1 1 calc R . . C31 C 0.8337(3) 0.16114(19) 0.07228(18) 0.0373(6) Uani 1 1 d . . . C17 C 0.5324(3) 0.36305(19) 0.4214(2) 0.0400(6) Uani 1 1 d . . . C36 C 0.7983(3) 0.2275(2) 0.03624(19) 0.0424(7) Uani 1 1 d . . . C2 C 0.7818(3) 0.7436(2) 0.3555(2) 0.0444(7) Uani 1 1 d . . . H2A H 0.6791 0.7521 0.3592 0.067 Uiso 1 1 calc R . . H2B H 0.8423 0.7925 0.3346 0.067 Uiso 1 1 calc R . . H2C H 0.8353 0.7607 0.4241 0.067 Uiso 1 1 calc R . . C38 C 0.5296(3) 0.1794(2) 0.0644(2) 0.0437(6) Uani 1 1 d . . . H38A H 0.4483 0.2110 0.0918 0.052 Uiso 1 1 calc R . . H38B H 0.4822 0.1173 -0.0068 0.052 Uiso 1 1 calc R . . C24 C 0.4444(3) 0.0667(2) 0.4035(2) 0.0407(6) Uani 1 1 d . . . H24 H 0.5502 0.0993 0.4397 0.049 Uiso 1 1 calc R . . C9 C 1.1534(3) 0.5147(2) 0.2054(2) 0.0396(6) Uani 1 1 d . . . H9 H 1.1109 0.4414 0.1869 0.047 Uiso 1 1 calc R . . C20 C 0.6580(3) -0.1135(2) 0.2071(2) 0.0465(7) Uani 1 1 d . . . H20A H 0.5516 -0.1477 0.1649 0.070 Uiso 1 1 calc R . . H20B H 0.6652 -0.1313 0.2629 0.070 Uiso 1 1 calc R . . H20C H 0.7291 -0.1398 0.1628 0.070 Uiso 1 1 calc R . . C27 C 0.1376(3) -0.0304(2) 0.2987(2) 0.0503(7) Uani 1 1 d . . . H27 H 0.0318 -0.0640 0.2625 0.060 Uiso 1 1 calc R . . C25 C 0.3312(3) 0.0391(2) 0.4519(2) 0.0468(7) Uani 1 1 d . . . H25 H 0.3597 0.0532 0.5213 0.056 Uiso 1 1 calc R . . C13 C 0.3623(3) 0.3675(2) 0.2910(2) 0.0430(6) Uani 1 1 d . . . H13 H 0.3487 0.3873 0.2392 0.052 Uiso 1 1 calc R . . C37 C 0.6588(3) 0.2631(2) 0.0590(2) 0.0469(7) Uani 1 1 d . . . H37A H 0.6198 0.2767 0.0038 0.056 Uiso 1 1 calc R . . H37B H 0.6893 0.3315 0.1263 0.056 Uiso 1 1 calc R . . C5 C 1.1411(3) 0.6945(2) 0.2850(2) 0.0446(7) Uani 1 1 d . . . H5 H 1.0901 0.7450 0.3211 0.054 Uiso 1 1 calc R . . C18 C 0.6947(3) 0.3904(2) 0.4786(2) 0.0442(7) Uani 1 1 d . . . H18A H 0.6963 0.3410 0.5060 0.053 Uiso 1 1 calc R . . H18B H 0.7286 0.4648 0.5385 0.053 Uiso 1 1 calc R . . C26 C 0.1785(3) -0.0085(2) 0.3996(2) 0.0492(7) Uani 1 1 d . . . H26 H 0.1011 -0.0264 0.4331 0.059 Uiso 1 1 calc R . . C7 C 1.3520(3) 0.6543(2) 0.2047(2) 0.0480(7) Uani 1 1 d . . . H7 H 1.4458 0.6772 0.1863 0.058 Uiso 1 1 calc R . . C21 C 0.8495(3) 0.1312(2) 0.4083(2) 0.0463(7) Uani 1 1 d . . . H21A H 0.9529 0.1237 0.4052 0.069 Uiso 1 1 calc R . . H21B H 0.8062 0.1075 0.4550 0.069 Uiso 1 1 calc R . . H21C H 0.8573 0.2068 0.4347 0.069 Uiso 1 1 calc R . . C28 C 0.2492(3) -0.0037(2) 0.2489(2) 0.0429(6) Uani 1 1 d . . . H28 H 0.2203 -0.0199 0.1788 0.051 Uiso 1 1 calc R . . C6 C 1.2774(3) 0.7272(2) 0.2580(2) 0.0506(7) Uani 1 1 d . . . H6 H 1.3204 0.8003 0.2761 0.061 Uiso 1 1 calc R . . C32 C 0.9656(3) 0.1305(2) 0.0550(2) 0.0466(7) Uani 1 1 d . . . H32 H 0.9890 0.0855 0.0795 0.056 Uiso 1 1 calc R . . C8 C 1.2894(3) 0.5485(2) 0.1786(2) 0.0470(7) Uani 1 1 d . . . H8 H 1.3402 0.4981 0.1418 0.056 Uiso 1 1 calc R . . C16 C 0.4026(4) 0.3122(2) 0.4437(2) 0.0525(8) Uani 1 1 d . . . H16 H 0.4153 0.2942 0.4968 0.063 Uiso 1 1 calc R . . C34 C 1.0294(4) 0.2314(3) -0.0323(2) 0.0594(9) Uani 1 1 d . . . H34 H 1.0965 0.2559 -0.0678 0.071 Uiso 1 1 calc R . . C35 C 0.8990(4) 0.2619(2) -0.0156(2) 0.0517(8) Uani 1 1 d . . . H35 H 0.8773 0.3074 -0.0399 0.062 Uiso 1 1 calc R . . C14 C 0.2340(3) 0.3135(2) 0.3116(3) 0.0534(8) Uani 1 1 d . . . H14 H 0.1327 0.2945 0.2729 0.064 Uiso 1 1 calc R . . C33 C 1.0629(4) 0.1653(2) 0.0024(2) 0.0559(8) Uani 1 1 d . . . H33 H 1.1524 0.1437 -0.0098 0.067 Uiso 1 1 calc R . . C15 C 0.2553(4) 0.2877(2) 0.3892(3) 0.0589(9) Uani 1 1 d . . . H15 H 0.1678 0.2527 0.4052 0.071 Uiso 1 1 calc R . . C1 C 0.7179(3) 0.5529(2) 0.1049(2) 0.0489(7) Uani 1 1 d . . . H1A H 0.6295 0.4864 0.0662 0.073 Uiso 1 1 calc R . . H1B H 0.8095 0.5408 0.0773 0.073 Uiso 1 1 calc R . . H1C H 0.6939 0.6101 0.0970 0.073 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 0.0332(4) 0.0373(4) 0.0371(4) 0.0235(4) 0.0083(3) 0.0105(3) Al2 0.0309(4) 0.0424(5) 0.0388(4) 0.0267(4) 0.0083(3) 0.0100(3) O1 0.0339(10) 0.0470(11) 0.0469(11) 0.0321(9) 0.0111(8) 0.0126(8) O2 0.0388(10) 0.0576(12) 0.0498(11) 0.0389(10) 0.0169(8) 0.0190(9) N2 0.0318(11) 0.0353(12) 0.0351(12) 0.0190(10) 0.0086(9) 0.0068(9) N1 0.0310(11) 0.0331(11) 0.0374(12) 0.0193(10) 0.0093(9) 0.0077(9) C3 0.0314(13) 0.0341(13) 0.0304(13) 0.0146(11) 0.0038(10) 0.0101(11) C4 0.0277(13) 0.0389(14) 0.0334(14) 0.0207(12) 0.0057(10) 0.0077(11) C10 0.0361(14) 0.0299(13) 0.0293(13) 0.0133(11) 0.0063(11) 0.0074(11) C11 0.0382(14) 0.0295(13) 0.0303(13) 0.0141(11) 0.0090(11) 0.0083(11) C12 0.0371(14) 0.0278(13) 0.0388(14) 0.0141(12) 0.0150(12) 0.0092(11) C23 0.0341(14) 0.0323(13) 0.0434(15) 0.0199(12) 0.0152(11) 0.0123(11) C30 0.0388(15) 0.0332(13) 0.0294(13) 0.0160(12) 0.0057(11) 0.0081(11) C29 0.0388(14) 0.0332(14) 0.0312(13) 0.0163(12) 0.0064(11) 0.0097(11) C22 0.0314(13) 0.0348(14) 0.0358(14) 0.0157(12) 0.0048(11) 0.0109(11) C19 0.0410(15) 0.0332(14) 0.0349(14) 0.0177(12) 0.0037(11) 0.0069(11) C31 0.0406(15) 0.0348(14) 0.0285(13) 0.0148(12) 0.0049(11) 0.0024(11) C17 0.0514(17) 0.0305(13) 0.0373(15) 0.0160(12) 0.0177(13) 0.0113(12) C36 0.0549(18) 0.0301(14) 0.0293(14) 0.0117(12) 0.0041(12) 0.0010(12) C2 0.0437(16) 0.0433(16) 0.0460(16) 0.0217(14) 0.0070(13) 0.0158(13) C38 0.0488(17) 0.0458(16) 0.0418(16) 0.0256(14) 0.0069(13) 0.0173(13) C24 0.0378(15) 0.0430(15) 0.0461(16) 0.0257(14) 0.0119(12) 0.0127(12) C9 0.0365(15) 0.0372(14) 0.0462(16) 0.0220(13) 0.0103(12) 0.0112(12) C20 0.0424(16) 0.0495(17) 0.0560(18) 0.0335(15) 0.0091(13) 0.0142(13) C27 0.0336(15) 0.0496(17) 0.064(2) 0.0258(16) 0.0184(14) 0.0102(13) C25 0.0569(19) 0.0501(17) 0.0465(17) 0.0291(15) 0.0244(14) 0.0241(15) C13 0.0396(16) 0.0391(15) 0.0495(17) 0.0210(14) 0.0147(13) 0.0124(12) C37 0.071(2) 0.0372(15) 0.0344(15) 0.0213(13) 0.0067(14) 0.0158(14) C5 0.0398(16) 0.0404(15) 0.0577(18) 0.0266(14) 0.0172(13) 0.0131(12) C18 0.0591(18) 0.0411(15) 0.0340(15) 0.0222(13) 0.0109(13) 0.0115(13) C26 0.0476(18) 0.0476(17) 0.063(2) 0.0306(16) 0.0326(15) 0.0209(14) C7 0.0353(15) 0.0586(19) 0.0580(19) 0.0369(16) 0.0150(13) 0.0106(14) C21 0.0344(15) 0.0575(18) 0.0481(17) 0.0314(15) 0.0053(12) 0.0076(13) C28 0.0363(15) 0.0421(15) 0.0467(16) 0.0199(14) 0.0119(12) 0.0108(12) C6 0.0443(17) 0.0430(16) 0.066(2) 0.0312(16) 0.0175(15) 0.0059(13) C32 0.0426(16) 0.0538(17) 0.0436(16) 0.0274(15) 0.0118(13) 0.0085(13) C8 0.0420(16) 0.0541(18) 0.0553(18) 0.0300(15) 0.0208(14) 0.0236(14) C16 0.066(2) 0.0413(16) 0.061(2) 0.0314(16) 0.0305(16) 0.0157(15) C34 0.061(2) 0.062(2) 0.0457(18) 0.0303(17) 0.0173(15) -0.0036(16) C35 0.073(2) 0.0382(16) 0.0347(16) 0.0197(13) 0.0091(15) 0.0006(15) C14 0.0359(16) 0.0420(16) 0.070(2) 0.0207(16) 0.0165(14) 0.0072(13) C33 0.0474(18) 0.067(2) 0.0476(18) 0.0289(17) 0.0155(14) 0.0068(15) C15 0.057(2) 0.0454(18) 0.077(2) 0.0327(17) 0.0367(18) 0.0105(15) C1 0.0537(18) 0.0547(18) 0.0414(16) 0.0282(15) 0.0091(13) 0.0139(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 Al1 O1 1.8028(17) . ? Al1 N1 1.948(2) . ? Al1 C2 1.954(3) . ? Al1 C1 1.957(3) . ? Al2 O2 1.7943(17) . ? Al2 N2 1.946(2) . ? Al2 C21 1.955(3) . ? Al2 C20 1.957(3) . ? O1 C11 1.307(3) . ? O2 C30 1.310(3) . ? N2 C22 1.316(3) . ? N2 C23 1.439(3) . ? N1 C3 1.317(3) . ? N1 C4 1.436(3) . ? C3 C10 1.406(3) . ? C3 H3 0.9500 . ? C4 C9 1.388(3) . ? C4 C5 1.389(3) . ? C10 C11 1.385(3) . ? C10 C19 1.517(3) . ? C11 C12 1.477(3) . ? C12 C13 1.393(4) . ? C12 C17 1.396(4) . ? C23 C24 1.385(4) . ? C23 C28 1.388(4) . ? C30 C29 1.381(3) . ? C30 C31 1.479(3) . ? C29 C22 1.409(3) . ? C29 C38 1.520(3) . ? C22 H22 0.9500 . ? C19 C18 1.521(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C31 C32 1.390(4) . ? C31 C36 1.404(4) . ? C17 C16 1.389(4) . ? C17 C18 1.507(4) . ? C36 C35 1.392(3) . ? C36 C37 1.501(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C38 C37 1.522(4) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C24 C25 1.390(3) . ? C24 H24 0.9500 . ? C9 C8 1.381(3) . ? C9 H9 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C27 C26 1.375(4) . ? C27 C28 1.389(3) . ? C27 H27 0.9500 . ? C25 C26 1.372(4) . ? C25 H25 0.9500 . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C26 H26 0.9500 . ? C7 C8 1.375(4) . ? C7 C6 1.383(4) . ? C7 H7 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C28 H28 0.9500 . ? C6 H6 0.9500 . ? C32 C33 1.386(3) . ? C32 H32 0.9500 . ? C8 H8 0.9500 . ? C16 C15 1.382(4) . ? C16 H16 0.9500 . ? C34 C35 1.376(4) . ? C34 C33 1.380(4) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C14 C15 1.385(4) . ? C14 H14 0.9500 . ? C33 H33 0.9500 . ? C15 H15 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 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 93.85(8) . . ? O1 Al1 C2 110.76(10) . . ? N1 Al1 C2 110.82(11) . . ? O1 Al1 C1 110.87(11) . . ? N1 Al1 C1 109.74(11) . . ? C2 Al1 C1 118.15(12) . . ? O2 Al2 N2 94.26(8) . . ? O2 Al2 C21 109.16(10) . . ? N2 Al2 C21 114.47(11) . . ? O2 Al2 C20 112.59(10) . . ? N2 Al2 C20 107.24(10) . . ? C21 Al2 C20 116.93(12) . . ? C11 O1 Al1 129.32(16) . . ? C30 O2 Al2 130.45(16) . . ? C22 N2 C23 117.8(2) . . ? C22 N2 Al2 122.32(16) . . ? C23 N2 Al2 119.48(16) . . ? C3 N1 C4 117.7(2) . . ? C3 N1 Al1 122.05(16) . . ? C4 N1 Al1 120.16(15) . . ? N1 C3 C10 126.8(2) . . ? N1 C3 H3 116.6 . . ? C10 C3 H3 116.6 . . ? C9 C4 C5 119.5(2) . . ? C9 C4 N1 121.5(2) . . ? C5 C4 N1 119.0(2) . . ? C11 C10 C3 122.2(2) . . ? C11 C10 C19 118.2(2) . . ? C3 C10 C19 119.3(2) . . ? O1 C11 C10 123.6(2) . . ? O1 C11 C12 116.5(2) . . ? C10 C11 C12 119.8(2) . . ? C13 C12 C17 120.3(2) . . ? C13 C12 C11 120.5(2) . . ? C17 C12 C11 119.1(2) . . ? C24 C23 C28 119.7(2) . . ? C24 C23 N2 118.8(2) . . ? C28 C23 N2 121.5(2) . . ? O2 C30 C29 123.5(2) . . ? O2 C30 C31 116.1(2) . . ? C29 C30 C31 120.4(2) . . ? C30 C29 C22 122.7(2) . . ? C30 C29 C38 118.4(2) . . ? C22 C29 C38 118.9(2) . . ? N2 C22 C29 126.8(2) . . ? N2 C22 H22 116.6 . . ? C29 C22 H22 116.6 . . ? C10 C19 C18 110.8(2) . . ? C10 C19 H19A 109.5 . . ? C18 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C32 C31 C36 120.1(2) . . ? C32 C31 C30 120.1(2) . . ? C36 C31 C30 119.7(2) . . ? C16 C17 C12 118.8(3) . . ? C16 C17 C18 122.1(3) . . ? C12 C17 C18 119.1(2) . . ? C35 C36 C31 118.3(3) . . ? C35 C36 C37 122.3(3) . . ? C31 C36 C37 119.4(2) . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C29 C38 C37 111.7(2) . . ? C29 C38 H38A 109.3 . . ? C37 C38 H38A 109.3 . . ? C29 C38 H38B 109.3 . . ? C37 C38 H38B 109.3 . . ? H38A C38 H38B 107.9 . . ? C23 C24 C25 120.1(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C8 C9 C4 120.0(2) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? Al2 C20 H20A 109.5 . . ? Al2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? Al2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C26 C27 C28 120.8(3) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C26 C25 C24 120.1(3) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C36 C37 C38 112.0(2) . . ? C36 C37 H37A 109.2 . . ? C38 C37 H37A 109.2 . . ? C36 C37 H37B 109.2 . . ? C38 C37 H37B 109.2 . . ? H37A C37 H37B 107.9 . . ? C6 C5 C4 119.9(2) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C17 C18 C19 110.1(2) . . ? C17 C18 H18A 109.6 . . ? C19 C18 H18A 109.6 . . ? C17 C18 H18B 109.6 . . ? C19 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C25 C26 C27 119.9(3) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C8 C7 C6 119.5(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? Al2 C21 H21A 109.5 . . ? Al2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? Al2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C28 C27 119.4(3) . . ? C23 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C5 C6 C7 120.6(3) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C33 C32 C31 120.3(3) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C7 C8 C9 120.6(2) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C15 C16 C17 120.6(3) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C35 C34 C33 120.2(3) . . ? C35 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? C34 C35 C36 121.4(3) . . ? C34 C35 H35 119.3 . . ? C36 C35 H35 119.3 . . ? C15 C14 C13 119.2(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C34 C33 C32 119.8(3) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.03 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.276 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 946614' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ly _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 Al F5 N O' _chemical_formula_weight 395.30 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' F F 0.0171 0.0103 '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 7.9649(7) _cell_length_b 15.0918(13) _cell_length_c 15.0663(13) _cell_angle_alpha 90.00 _cell_angle_beta 102.838(2) _cell_angle_gamma 90.00 _cell_volume 1765.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 185(2) _cell_measurement_reflns_used 1727 _cell_measurement_theta_min 2.6228 _cell_measurement_theta_max 22.3867 _exptl_crystal_description BLOCK _exptl_crystal_colour yellow _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9481 _exptl_absorpt_correction_T_max 0.9761 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 185(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 'Bruker APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10242 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3110 _reflns_number_gt 2201 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0511P)^2^+0.2669P] 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 3110 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Al1 Al 0.61702(10) 0.10523(5) 0.70695(5) 0.0347(2) Uani 1 1 d . . . F5 F 0.44581(19) 0.40000(9) 0.61853(10) 0.0489(4) Uani 1 1 d . . . F1 F 0.55625(19) 0.11388(9) 0.51704(10) 0.0483(4) Uani 1 1 d . . . F2 F 0.3841(2) 0.15671(10) 0.34795(10) 0.0528(4) Uani 1 1 d . . . N1 N 0.6028(2) 0.22822(12) 0.66132(13) 0.0320(5) Uani 1 1 d . . . O1 O 0.6659(2) 0.14111(11) 0.82466(11) 0.0374(4) Uani 1 1 d . . . F3 F 0.2424(2) 0.31983(11) 0.31348(10) 0.0585(5) Uani 1 1 d . . . F4 F 0.2833(2) 0.44181(10) 0.44926(11) 0.0606(5) Uani 1 1 d . . . C5 C 0.4877(3) 0.19567(16) 0.50153(18) 0.0354(6) Uani 1 1 d . . . C12 C 0.8690(3) 0.19972(16) 0.95005(16) 0.0333(6) Uani 1 1 d . . . C7 C 0.3306(3) 0.29942(18) 0.39721(17) 0.0398(6) Uani 1 1 d . . . C4 C 0.5118(3) 0.25534(16) 0.57404(16) 0.0322(6) Uani 1 1 d . . . C11 C 0.7714(3) 0.20577(15) 0.85532(16) 0.0326(6) Uani 1 1 d . . . C13 C 0.8816(3) 0.11847(16) 0.99576(17) 0.0393(6) Uani 1 1 d . . . H13 H 0.8217 0.0683 0.9664 0.047 Uiso 1 1 calc R . . C9 C 0.4379(3) 0.33845(16) 0.55291(17) 0.0356(6) Uani 1 1 d . . . C6 C 0.4002(3) 0.21658(17) 0.41542(17) 0.0378(6) Uani 1 1 d . . . C3 C 0.7048(3) 0.28824(16) 0.71233(17) 0.0340(6) Uani 1 1 d . . . H3 H 0.7167 0.3436 0.6843 0.041 Uiso 1 1 calc R . . C10 C 0.7953(3) 0.27817(15) 0.80209(16) 0.0317(6) Uani 1 1 d . . . C8 C 0.3512(3) 0.36052(16) 0.46617(18) 0.0404(6) Uani 1 1 d . . . C16 C 1.0523(3) 0.26493(19) 1.08167(18) 0.0441(7) Uani 1 1 d . . . H16 H 1.1104 0.3150 1.1124 0.053 Uiso 1 1 calc R . . C19 C 0.9248(3) 0.34905(16) 0.84288(17) 0.0371(6) Uani 1 1 d . . . H19A H 0.8919 0.4058 0.8107 0.045 Uiso 1 1 calc R . . H19B H 1.0399 0.3321 0.8338 0.045 Uiso 1 1 calc R . . C1 C 0.3979(3) 0.04224(17) 0.67929(19) 0.0458(7) Uani 1 1 d . . . H1A H 0.4166 -0.0199 0.6976 0.069 Uiso 1 1 calc R . . H1B H 0.3481 0.0455 0.6138 0.069 Uiso 1 1 calc R . . H1C H 0.3187 0.0695 0.7126 0.069 Uiso 1 1 calc R . . C14 C 0.9801(4) 0.11066(19) 1.08292(17) 0.0451(7) Uani 1 1 d . . . H14 H 0.9886 0.0552 1.1135 0.054 Uiso 1 1 calc R . . C2 C 0.8266(3) 0.04908(18) 0.68862(19) 0.0493(7) Uani 1 1 d . . . H2A H 0.9240 0.0896 0.7080 0.074 Uiso 1 1 calc R . . H2B H 0.8138 0.0348 0.6240 0.074 Uiso 1 1 calc R . . H2C H 0.8476 -0.0055 0.7247 0.074 Uiso 1 1 calc R . . C17 C 0.9550(3) 0.27429(16) 0.99384(17) 0.0360(6) Uani 1 1 d . . . C18 C 0.9344(4) 0.36195(16) 0.94427(18) 0.0414(7) Uani 1 1 d . . . H18A H 1.0332 0.4008 0.9704 0.050 Uiso 1 1 calc R . . H18B H 0.8281 0.3915 0.9527 0.050 Uiso 1 1 calc R . . C15 C 1.0663(4) 0.18346(19) 1.12560(18) 0.0472(7) Uani 1 1 d . . . H15 H 1.1357 0.1779 1.1854 0.057 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 0.0344(5) 0.0270(4) 0.0417(5) -0.0014(3) 0.0061(3) -0.0006(3) F5 0.0579(11) 0.0362(8) 0.0488(9) -0.0081(7) 0.0036(8) 0.0087(7) F1 0.0529(10) 0.0360(9) 0.0529(10) -0.0060(7) 0.0049(8) 0.0121(7) F2 0.0563(11) 0.0551(10) 0.0442(9) -0.0130(8) 0.0049(8) 0.0024(8) N1 0.0294(11) 0.0279(11) 0.0376(12) -0.0010(9) 0.0053(9) 0.0011(9) O1 0.0399(11) 0.0300(9) 0.0405(10) -0.0010(8) 0.0051(8) -0.0098(8) F3 0.0662(11) 0.0615(11) 0.0410(9) 0.0095(8) -0.0026(8) 0.0014(9) F4 0.0765(12) 0.0401(9) 0.0587(10) 0.0084(8) 0.0010(9) 0.0158(9) C5 0.0286(14) 0.0286(13) 0.0498(16) -0.0013(12) 0.0107(12) 0.0017(11) C12 0.0307(14) 0.0341(14) 0.0364(14) -0.0024(11) 0.0103(11) 0.0014(11) C7 0.0364(16) 0.0457(16) 0.0351(15) 0.0067(13) 0.0030(12) -0.0038(13) C4 0.0267(14) 0.0312(14) 0.0394(15) 0.0004(11) 0.0092(11) -0.0012(11) C11 0.0296(14) 0.0285(13) 0.0407(14) -0.0048(11) 0.0096(11) 0.0009(11) C13 0.0463(16) 0.0342(14) 0.0386(15) -0.0024(12) 0.0120(12) -0.0020(12) C9 0.0366(15) 0.0314(14) 0.0392(15) -0.0024(12) 0.0093(12) 0.0003(11) C6 0.0365(15) 0.0400(15) 0.0368(15) -0.0045(12) 0.0079(12) -0.0038(13) C3 0.0296(14) 0.0295(13) 0.0448(15) 0.0030(12) 0.0122(12) 0.0008(11) C10 0.0290(14) 0.0293(13) 0.0373(14) -0.0022(11) 0.0082(11) -0.0004(11) C8 0.0404(16) 0.0308(14) 0.0492(17) 0.0082(13) 0.0082(13) 0.0060(12) C16 0.0426(17) 0.0495(17) 0.0402(16) -0.0103(13) 0.0088(13) -0.0046(14) C19 0.0337(15) 0.0303(13) 0.0465(16) 0.0007(12) 0.0072(12) -0.0049(11) C1 0.0454(17) 0.0354(15) 0.0553(17) -0.0052(13) 0.0084(14) -0.0014(13) C14 0.0527(19) 0.0472(17) 0.0367(15) 0.0065(13) 0.0130(13) 0.0037(14) C2 0.0464(18) 0.0402(16) 0.0604(19) 0.0029(14) 0.0101(14) 0.0064(14) C17 0.0330(15) 0.0389(15) 0.0384(15) -0.0072(12) 0.0127(12) -0.0012(12) C18 0.0384(16) 0.0359(14) 0.0499(16) -0.0097(13) 0.0100(13) -0.0053(12) C15 0.0458(18) 0.063(2) 0.0324(15) -0.0004(14) 0.0087(13) 0.0010(15) _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 1.8121(18) . ? Al1 C2 1.945(3) . ? Al1 C1 1.950(3) . ? Al1 N1 1.974(2) . ? F5 C9 1.348(3) . ? F1 C5 1.349(3) . ? F2 C6 1.345(3) . ? N1 C3 1.339(3) . ? N1 C4 1.414(3) . ? O1 C11 1.304(3) . ? F3 C7 1.336(3) . ? F4 C8 1.342(3) . ? C5 C6 1.366(3) . ? C5 C4 1.396(3) . ? C12 C13 1.399(3) . ? C12 C17 1.404(3) . ? C12 C11 1.468(3) . ? C7 C6 1.371(4) . ? C7 C8 1.371(3) . ? C4 C9 1.392(3) . ? C11 C10 1.393(3) . ? C13 C14 1.377(4) . ? C13 H13 0.9500 . ? C9 C8 1.376(3) . ? C3 C10 1.392(3) . ? C3 H3 0.9500 . ? C10 C19 1.518(3) . ? C16 C17 1.384(3) . ? C16 C15 1.389(4) . ? C16 H16 0.9500 . ? C19 C18 1.525(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C14 C15 1.377(4) . ? C14 H14 0.9500 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C17 C18 1.510(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C15 H15 0.9500 . ? 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 C2 105.34(11) . . ? O1 Al1 C1 110.01(10) . . ? C2 Al1 C1 120.86(12) . . ? O1 Al1 N1 92.47(8) . . ? C2 Al1 N1 110.17(11) . . ? C1 Al1 N1 113.87(10) . . ? C3 N1 C4 117.3(2) . . ? C3 N1 Al1 117.10(16) . . ? C4 N1 Al1 125.03(16) . . ? C11 O1 Al1 123.48(16) . . ? F1 C5 C6 118.5(2) . . ? F1 C5 C4 118.3(2) . . ? C6 C5 C4 123.1(2) . . ? C13 C12 C17 119.8(2) . . ? C13 C12 C11 119.8(2) . . ? C17 C12 C11 120.3(2) . . ? F3 C7 C6 120.2(2) . . ? F3 C7 C8 120.6(2) . . ? C6 C7 C8 119.1(2) . . ? C9 C4 C5 115.1(2) . . ? C9 C4 N1 125.2(2) . . ? C5 C4 N1 119.6(2) . . ? O1 C11 C10 122.9(2) . . ? O1 C11 C12 117.3(2) . . ? C10 C11 C12 119.9(2) . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? F5 C9 C8 117.5(2) . . ? F5 C9 C4 120.3(2) . . ? C8 C9 C4 122.2(2) . . ? F2 C6 C5 120.4(2) . . ? F2 C6 C7 119.7(2) . . ? C5 C6 C7 119.9(2) . . ? N1 C3 C10 126.9(2) . . ? N1 C3 H3 116.5 . . ? C10 C3 H3 116.5 . . ? C3 C10 C11 122.5(2) . . ? C3 C10 C19 118.3(2) . . ? C11 C10 C19 119.1(2) . . ? F4 C8 C7 119.7(2) . . ? F4 C8 C9 119.8(2) . . ? C7 C8 C9 120.5(2) . . ? C17 C16 C15 121.0(3) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C10 C19 C18 112.0(2) . . ? C10 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? C10 C19 H19B 109.2 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? Al1 C1 H1A 109.5 . . ? Al1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Al1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C15 C14 C13 119.8(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? Al1 C2 H2A 109.5 . . ? Al1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Al1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C16 C17 C12 118.6(2) . . ? C16 C17 C18 122.6(2) . . ? C12 C17 C18 118.8(2) . . ? C17 C18 C19 111.1(2) . . ? C17 C18 H18A 109.4 . . ? C19 C18 H18A 109.4 . . ? C17 C18 H18B 109.4 . . ? C19 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C14 C15 C16 120.3(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.234 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.046 _database_code_depnum_ccdc_archive 'CCDC 946615'