Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Sean Barry' _publ_contact_author_address ; Department of Chemistry Carleton University 2240 Herzberg Pavilion 1125 Colonel By Drive Ottawa ON K1S 5B6 CANADA ; _publ_contact_author_email SBARRY@CCS.CARLETON.CA _publ_section_title ; Mechanistic Investigation of Ligand Exchange in Guanidinate Ligand Systems,Mechanistic Investigation of Ligand Exchange in Guanidinate Ligand Systems ; loop_ _publ_author_name 'Sean Barry' 'Allison L. Brazeau' 'Gino DiLabio' 'Kevin Kreisel' 'Wesley Monillas' 'Glenn P. A. Yap' data_seab005 _database_code_depnum_ccdc_archive 'CCDC 621800' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21.50 H44 Al2 Cl4 N6' _chemical_formula_weight 582.39 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.383(5) _cell_length_b 14.935(6) _cell_length_c 31.025(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6201(4) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2472 _exptl_absorpt_coefficient_mu 0.460 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8304 _exptl_absorpt_correction_T_max 0.9642 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30371 _diffrn_reflns_av_R_equivalents 0.0849 _diffrn_reflns_av_sigmaI/netI 0.0511 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 22.50 _reflns_number_total 4053 _reflns_number_gt 3626 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4053 _refine_ls_number_parameters 363 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0900 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.2538 _refine_ls_wR_factor_gt 0.2462 _refine_ls_goodness_of_fit_ref 1.992 _refine_ls_restrained_S_all 1.992 _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 -0.09557(11) 0.62841(11) 0.16670(5) 0.0505(5) Uani 1 1 d . A . Al2 Al 0.09639(9) 0.51609(11) 0.11828(4) 0.0429(5) Uani 1 1 d . A . Cl1 Cl -0.25072(10) 0.59293(11) 0.15904(6) 0.0822(6) Uani 1 1 d . . . Cl2 Cl -0.08056(14) 0.74455(10) 0.20742(5) 0.0807(6) Uani 1 1 d . . . Cl3 Cl 0.20711(9) 0.43928(11) 0.15305(4) 0.0649(5) Uani 1 1 d . . . Cl4 Cl 0.13054(10) 0.50813(11) 0.05056(4) 0.0596(5) Uani 1 1 d . . . N1 N -0.0389(3) 0.5307(3) 0.19406(13) 0.0476(11) Uani 1 1 d . . . N2 N -0.0845(3) 0.3771(3) 0.19189(15) 0.0558(12) Uani 1 1 d . . . N3 N -0.0215(3) 0.4522(2) 0.13076(11) 0.0360(9) Uani 1 1 d . . . N4 N 0.1140(3) 0.6388(3) 0.12924(12) 0.0480(11) Uani 1 1 d . . . N5 N 0.0754(3) 0.7715(3) 0.09165(15) 0.0606(13) Uani 1 1 d . . . N6 N -0.0498(3) 0.6698(2) 0.11276(12) 0.0404(10) Uani 1 1 d . . . C1 C -0.0054(18) 0.4996(13) 0.2391(7) 0.045(2) Uani 0.335(8) 1 d P A 1 H1A H -0.0027 0.4329 0.2414 0.054 Uiso 0.335(8) 1 calc PR A 1 C1' C -0.0024(7) 0.5446(7) 0.2412(3) 0.045(2) Uani 0.665(8) 1 d P A 2 H1'A H 0.0412 0.5989 0.2407 0.054 Uiso 0.665(8) 1 calc PR A 2 C2 C -0.108(2) 0.547(3) 0.2706(12) 0.062(3) Uani 0.335(8) 1 d P A 1 H2A H -0.0955 0.5367 0.3014 0.093 Uiso 0.335(8) 1 calc PR A 1 H2B H -0.1708 0.5178 0.2624 0.093 Uiso 0.335(8) 1 calc PR A 1 H2C H -0.1128 0.6113 0.2651 0.093 Uiso 0.335(8) 1 calc PR A 1 C2' C -0.0713(8) 0.5580(13) 0.2749(5) 0.062(3) Uani 0.665(8) 1 d P A 2 H2'A H -0.1155 0.6081 0.2677 0.093 Uiso 0.665(8) 1 calc PR A 2 H2'B H -0.0351 0.5717 0.3016 0.093 Uiso 0.665(8) 1 calc PR A 2 H2'C H -0.1112 0.5036 0.2790 0.093 Uiso 0.665(8) 1 calc PR A 2 C3 C 0.0952(12) 0.5416(10) 0.2456(5) 0.0500(18) Uani 0.335(8) 1 d P A 1 H3A H 0.1441 0.5124 0.2267 0.075 Uiso 0.335(8) 1 calc PR A 1 H3B H 0.1157 0.5343 0.2757 0.075 Uiso 0.335(8) 1 calc PR A 1 H3C H 0.0916 0.6055 0.2386 0.075 Uiso 0.335(8) 1 calc PR A 1 C3' C 0.0632(6) 0.4685(5) 0.2551(2) 0.0500(18) Uani 0.665(8) 1 d P A 2 H3'A H 0.1196 0.4629 0.2351 0.075 Uiso 0.665(8) 1 calc PR A 2 H3'B H 0.0245 0.4128 0.2550 0.075 Uiso 0.665(8) 1 calc PR A 2 H3'C H 0.0884 0.4800 0.2842 0.075 Uiso 0.665(8) 1 calc PR A 2 C4 C -0.0485(3) 0.4515(3) 0.17260(16) 0.0433(12) Uani 1 1 d . A . C5 C -0.1674(4) 0.3802(5) 0.2227(2) 0.078(2) Uani 1 1 d . A . H5A H -0.1420 0.3691 0.2518 0.117 Uiso 1 1 calc R . . H5B H -0.2167 0.3341 0.2152 0.117 Uiso 1 1 calc R . . H5C H -0.1991 0.4393 0.2216 0.117 Uiso 1 1 calc R . . C6 C -0.0447(5) 0.2888(4) 0.1841(2) 0.082(2) Uani 1 1 d . A . H6A H 0.0203 0.2939 0.1698 0.123 Uiso 1 1 calc R . . H6B H -0.0908 0.2552 0.1657 0.123 Uiso 1 1 calc R . . H6C H -0.0366 0.2574 0.2116 0.123 Uiso 1 1 calc R . . C7 C -0.0748(4) 0.3899(3) 0.10077(17) 0.0480(13) Uani 1 1 d . A . H7A H -0.1255 0.3558 0.1178 0.058 Uiso 1 1 calc R . . C8 C -0.0066(5) 0.3230(4) 0.0788(2) 0.0727(18) Uani 1 1 d . . . H8A H 0.0287 0.2877 0.1006 0.109 Uiso 1 1 calc R A . H8B H 0.0420 0.3550 0.0609 0.109 Uiso 1 1 calc R . . H8C H -0.0465 0.2830 0.0606 0.109 Uiso 1 1 calc R . . C9 C -0.1303(4) 0.4448(3) 0.06621(18) 0.0523(13) Uani 1 1 d . . . H9A H -0.1723 0.4900 0.0803 0.078 Uiso 1 1 calc R A . H9B H -0.1724 0.4049 0.0489 0.078 Uiso 1 1 calc R . . H9C H -0.0816 0.4746 0.0475 0.078 Uiso 1 1 calc R . . C10 C 0.2022(7) 0.6939(8) 0.1482(3) 0.039(2) Uani 0.624(12) 1 d P A 1 H10A H 0.1973 0.7426 0.1262 0.047 Uiso 0.624(12) 1 calc PR A 1 C10' C 0.2141(13) 0.6452(13) 0.1506(5) 0.039(2) Uani 0.376(12) 1 d P A 2 H10B H 0.2132 0.5812 0.1600 0.047 Uiso 0.376(12) 1 calc PR A 2 C11 C 0.3040(17) 0.6563(15) 0.1304(7) 0.055(4) Uani 0.624(12) 1 d P A 1 H11A H 0.3596 0.6910 0.1424 0.082 Uiso 0.624(12) 1 calc PR A 1 H11B H 0.3048 0.6612 0.0989 0.082 Uiso 0.624(12) 1 calc PR A 1 H11C H 0.3111 0.5933 0.1387 0.082 Uiso 0.624(12) 1 calc PR A 1 C11' C 0.301(3) 0.631(3) 0.1211(12) 0.055(4) Uani 0.376(12) 1 d P A 2 H11D H 0.2785 0.6007 0.0949 0.082 Uiso 0.376(12) 1 calc PR A 2 H11E H 0.3516 0.5949 0.1356 0.082 Uiso 0.376(12) 1 calc PR A 2 H11F H 0.3297 0.6896 0.1134 0.082 Uiso 0.376(12) 1 calc PR A 2 C12 C 0.2127(12) 0.7350(10) 0.1723(5) 0.0464(17) Uani 0.342(8) 1 d P A 1 H12A H 0.1489 0.7624 0.1804 0.070 Uiso 0.342(8) 1 calc PR A 1 H12B H 0.2599 0.7818 0.1637 0.070 Uiso 0.342(8) 1 calc PR A 1 H12C H 0.2398 0.7019 0.1969 0.070 Uiso 0.342(8) 1 calc PR A 1 C12' C 0.2004(6) 0.6810(5) 0.1969(2) 0.0464(17) Uani 0.658(8) 1 d P A 2 H12D H 0.2658 0.6855 0.2110 0.070 Uiso 0.658(8) 1 calc PR A 2 H12E H 0.1577 0.6398 0.2132 0.070 Uiso 0.658(8) 1 calc PR A 2 H12F H 0.1691 0.7402 0.1959 0.070 Uiso 0.658(8) 1 calc PR A 2 C13 C 0.0469(4) 0.6945(3) 0.11070(15) 0.0471(13) Uani 1 1 d . A . C14 C 0.1621(4) 0.7786(5) 0.0636(2) 0.0768(19) Uani 1 1 d . A . H14A H 0.1867 0.7185 0.0566 0.115 Uiso 1 1 calc R . . H14B H 0.2149 0.8124 0.0783 0.115 Uiso 1 1 calc R . . H14C H 0.1433 0.8096 0.0370 0.115 Uiso 1 1 calc R . . C15 C 0.0228(6) 0.8561(4) 0.0991(2) 0.084(2) Uani 1 1 d . A . H15A H -0.0310 0.8466 0.1200 0.126 Uiso 1 1 calc R . . H15B H -0.0056 0.8776 0.0719 0.126 Uiso 1 1 calc R . . H15C H 0.0698 0.9007 0.1103 0.126 Uiso 1 1 calc R . . C16 C -0.1219(4) 0.6868(3) 0.07745(17) 0.0508(13) Uani 1 1 d . A . H16 H -0.1648 0.6320 0.0764 0.061 Uiso 1 1 calc R . . C17 C -0.0752(4) 0.6932(3) 0.03316(17) 0.0542(14) Uani 1 1 d . . . H17A H -0.1274 0.6877 0.0111 0.081 Uiso 1 1 calc R A . H17B H -0.0265 0.6448 0.0295 0.081 Uiso 1 1 calc R . . H17C H -0.0415 0.7511 0.0301 0.081 Uiso 1 1 calc R . . C18 C -0.1951(4) 0.7647(4) 0.0857(2) 0.0701(17) Uani 1 1 d . . . H18A H -0.2145 0.7651 0.1162 0.105 Uiso 1 1 calc R A . H18B H -0.2547 0.7570 0.0677 0.105 Uiso 1 1 calc R . . H18C H -0.1625 0.8215 0.0785 0.105 Uiso 1 1 calc R . . C19 C -0.081(2) 0.9711(17) -0.0188(14) 0.055(8) Uani 0.50 1 d P B -1 H19A H -0.1493 0.9594 -0.0239 0.066 Uiso 0.50 1 calc PR B -1 C20 C -0.0030(14) 0.9291(8) -0.0440(7) 0.069(4) Uani 0.50 1 d P B -1 H20A H -0.0198 0.8871 -0.0658 0.083 Uiso 0.50 1 calc PR B -1 C21 C 0.0940(19) 0.9498(14) -0.0364(7) 0.080(7) Uani 0.50 1 d P B -1 H21A H 0.1443 0.9200 -0.0526 0.097 Uiso 0.50 1 calc PR B -1 C22 C 0.1210(14) 1.0092(16) -0.0077(7) 0.082(6) Uani 0.50 1 d P B -1 H22A H 0.1892 1.0255 -0.0043 0.099 Uiso 0.50 1 calc PR B -1 C23 C 0.047(2) 1.048(2) 0.0178(10) 0.059(8) Uani 0.50 1 d P B -1 H23A H 0.0666 1.0894 0.0395 0.070 Uiso 0.50 1 calc PR B -1 C24 C -0.0499(10) 1.0292(8) 0.0131(5) 0.058(3) Uani 0.50 1 d P B -1 C25 C -0.124(2) 1.0684(16) 0.0454(9) 0.114(11) Uani 0.50 1 d P B -1 H25A H -0.0885 1.1075 0.0656 0.171 Uiso 0.50 1 calc PR B -1 H25B H -0.1562 1.0196 0.0614 0.171 Uiso 0.50 1 calc PR B -1 H25C H -0.1749 1.1030 0.0300 0.171 Uiso 0.50 1 calc PR B -1 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 0.0387(9) 0.0526(10) 0.0600(10) 0.0063(7) 0.0180(7) 0.0014(7) Al2 0.0226(8) 0.0708(11) 0.0352(8) 0.0042(7) -0.0003(5) 0.0024(6) Cl1 0.0302(8) 0.0855(12) 0.1309(15) 0.0491(10) 0.0199(8) 0.0070(7) Cl2 0.1051(13) 0.0664(11) 0.0706(11) -0.0088(8) 0.0338(9) 0.0153(9) Cl3 0.0303(8) 0.1074(12) 0.0571(9) 0.0030(7) -0.0084(6) 0.0210(7) Cl4 0.0450(8) 0.0942(11) 0.0397(8) -0.0055(6) 0.0058(5) -0.0053(7) N1 0.031(2) 0.071(3) 0.041(2) 0.013(2) 0.0087(17) -0.0013(19) N2 0.042(2) 0.059(3) 0.066(3) 0.035(2) -0.002(2) 0.005(2) N3 0.0273(19) 0.041(2) 0.040(2) 0.0096(16) -0.0021(16) 0.0047(16) N4 0.030(2) 0.084(3) 0.030(2) 0.003(2) 0.0009(16) -0.019(2) N5 0.067(3) 0.060(3) 0.055(3) 0.004(2) 0.006(2) -0.032(2) N6 0.036(2) 0.037(2) 0.048(2) 0.0065(17) 0.0034(17) -0.0064(17) C1 0.062(4) 0.038(6) 0.036(3) -0.007(5) 0.021(3) -0.013(6) C1' 0.062(4) 0.038(6) 0.036(3) -0.007(5) 0.021(3) -0.013(6) C2 0.042(9) 0.095(7) 0.048(5) 0.004(4) 0.025(7) -0.017(8) C2' 0.042(9) 0.095(7) 0.048(5) 0.004(4) 0.025(7) -0.017(8) C3 0.062(5) 0.050(4) 0.038(4) 0.005(3) -0.012(3) -0.007(4) C3' 0.062(5) 0.050(4) 0.038(4) 0.005(3) -0.012(3) -0.007(4) C4 0.021(2) 0.054(3) 0.055(3) 0.020(3) -0.006(2) 0.005(2) C5 0.049(3) 0.098(5) 0.088(5) 0.051(4) 0.004(3) -0.016(3) C6 0.100(5) 0.067(4) 0.080(4) 0.044(3) -0.019(4) 0.018(4) C7 0.051(3) 0.038(3) 0.056(3) 0.017(2) -0.014(2) 0.002(2) C8 0.100(5) 0.046(3) 0.073(4) 0.005(3) -0.018(4) 0.015(3) C9 0.053(3) 0.043(3) 0.061(3) 0.020(2) -0.021(3) -0.010(2) C10 0.041(4) 0.039(6) 0.037(3) -0.003(6) -0.001(3) -0.021(5) C10' 0.041(4) 0.039(6) 0.037(3) -0.003(6) -0.001(3) -0.021(5) C11 0.034(3) 0.096(14) 0.034(10) -0.009(7) -0.010(6) -0.038(7) C11' 0.034(3) 0.096(14) 0.034(10) -0.009(7) -0.010(6) -0.038(7) C12 0.053(4) 0.046(4) 0.040(4) -0.011(3) -0.001(3) -0.022(3) C12' 0.053(4) 0.046(4) 0.040(4) -0.011(3) -0.001(3) -0.022(3) C13 0.050(3) 0.052(3) 0.039(3) -0.008(2) 0.008(2) -0.023(3) C14 0.064(4) 0.104(5) 0.063(4) 0.020(4) -0.002(3) -0.041(4) C15 0.106(5) 0.050(4) 0.097(5) -0.004(3) 0.006(4) -0.035(4) C16 0.041(3) 0.038(3) 0.073(4) 0.009(2) -0.004(2) -0.007(2) C17 0.057(3) 0.041(3) 0.065(4) 0.013(2) -0.017(3) -0.006(2) C18 0.061(4) 0.044(3) 0.105(5) 0.021(3) 0.010(3) 0.013(3) C19 0.021(12) 0.034(9) 0.111(19) 0.009(10) -0.005(11) -0.016(9) C20 0.068(11) 0.039(7) 0.100(13) 0.000(7) 0.001(10) 0.002(6) C21 0.107(19) 0.066(13) 0.068(13) 0.015(11) 0.087(15) 0.040(11) C22 0.054(12) 0.112(16) 0.080(13) 0.045(12) 0.021(9) -0.001(11) C23 0.05(2) 0.071(17) 0.055(11) 0.017(11) 0.001(14) -0.020(13) C24 0.048(10) 0.043(7) 0.084(11) 0.008(7) 0.028(8) -0.011(7) C25 0.15(2) 0.064(12) 0.124(16) -0.029(10) 0.128(15) -0.008(13) _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 N1 1.851(4) . ? Al1 N6 1.886(4) . ? Al1 Cl2 2.155(2) . ? Al1 Cl1 2.156(2) . ? Al2 N4 1.879(5) . ? Al2 N3 1.885(4) . ? Al2 Cl4 2.154(2) . ? Al2 Cl3 2.1624(19) . ? N1 C4 1.363(7) . ? N1 C1 1.54(2) . ? N1 C1' 1.556(10) . ? N2 C4 1.351(6) . ? N2 C6 1.442(8) . ? N2 C5 1.465(7) . ? N3 C4 1.347(6) . ? N3 C7 1.497(6) . ? N4 C13 1.353(7) . ? N4 C10' 1.497(17) . ? N4 C10 1.555(10) . ? N5 C13 1.348(6) . ? N5 C14 1.455(7) . ? N5 C15 1.464(8) . ? N6 C13 1.347(6) . ? N6 C16 1.482(6) . ? C1 C3 1.50(3) . ? C1 C2 1.83(4) . ? C1' C2' 1.408(17) . ? C1' C3' 1.499(14) . ? C7 C8 1.515(8) . ? C7 C9 1.541(6) . ? C10 C12 0.976(16) . ? C10 C11 1.58(3) . ? C10' C11' 1.49(5) . ? C10' C12' 1.543(18) . ? C16 C17 1.513(7) . ? C16 C18 1.542(7) . ? C19 C24 1.38(4) . ? C19 C20 1.44(3) . ? C20 C21 1.35(3) . ? C21 C22 1.31(3) . ? C22 C23 1.39(4) . ? C23 C24 1.34(3) . ? C24 C25 1.527(18) . ? 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 Al1 N6 122.18(18) . . ? N1 Al1 Cl2 109.13(17) . . ? N6 Al1 Cl2 103.05(14) . . ? N1 Al1 Cl1 104.54(14) . . ? N6 Al1 Cl1 107.20(14) . . ? Cl2 Al1 Cl1 110.62(9) . . ? N4 Al2 N3 124.19(17) . . ? N4 Al2 Cl4 101.76(14) . . ? N3 Al2 Cl4 110.50(13) . . ? N4 Al2 Cl3 109.95(14) . . ? N3 Al2 Cl3 101.69(13) . . ? Cl4 Al2 Cl3 108.18(8) . . ? C4 N1 C1 102.1(8) . . ? C4 N1 C1' 127.2(5) . . ? C1 N1 C1' 25.2(6) . . ? C4 N1 Al1 114.9(3) . . ? C1 N1 Al1 140.6(8) . . ? C1' N1 Al1 117.0(5) . . ? C4 N2 C6 123.1(5) . . ? C4 N2 C5 122.2(5) . . ? C6 N2 C5 114.7(5) . . ? C4 N3 C7 117.8(4) . . ? C4 N3 Al2 115.2(3) . . ? C7 N3 Al2 125.9(3) . . ? C13 N4 C10' 137.9(9) . . ? C13 N4 C10 109.8(6) . . ? C10' N4 C10 28.3(6) . . ? C13 N4 Al2 116.1(3) . . ? C10' N4 Al2 104.8(8) . . ? C10 N4 Al2 132.9(5) . . ? C13 N5 C14 123.4(5) . . ? C13 N5 C15 122.0(5) . . ? C14 N5 C15 114.5(5) . . ? C13 N6 C16 123.0(4) . . ? C13 N6 Al1 116.3(3) . . ? C16 N6 Al1 120.0(3) . . ? C3 C1 N1 105.0(13) . . ? C3 C1 C2 116.2(16) . . ? N1 C1 C2 98.7(18) . . ? C2' C1' C3' 106.1(10) . . ? C2' C1' N1 120.8(9) . . ? C3' C1' N1 110.6(7) . . ? N3 C4 N2 121.9(5) . . ? N3 C4 N1 116.0(4) . . ? N2 C4 N1 122.1(5) . . ? N3 C7 C8 113.8(4) . . ? N3 C7 C9 109.3(4) . . ? C8 C7 C9 109.1(5) . . ? C12 C10 N4 137.0(12) . . ? C12 C10 C11 111.6(12) . . ? N4 C10 C11 109.5(7) . . ? C11' C10' N4 114.6(17) . . ? C11' C10' C12' 135.3(17) . . ? N4 C10' C12' 109.1(11) . . ? N6 C13 N5 121.7(5) . . ? N6 C13 N4 116.7(4) . . ? N5 C13 N4 121.5(4) . . ? N6 C16 C17 114.4(4) . . ? N6 C16 C18 114.8(5) . . ? C17 C16 C18 111.5(4) . . ? C24 C19 C20 117(2) . . ? C21 C20 C19 119.7(18) . . ? C22 C21 C20 122.5(15) . . ? C21 C22 C23 118(2) . . ? C24 C23 C22 123(3) . . ? C23 C24 C19 120(2) . . ? C23 C24 C25 119(2) . . ? C19 C24 C25 121(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N6 Al1 N1 C4 -63.5(4) . . . . ? Cl2 Al1 N1 C4 176.5(3) . . . . ? Cl1 Al1 N1 C4 58.1(3) . . . . ? N6 Al1 N1 C1 137.8(13) . . . . ? Cl2 Al1 N1 C1 17.8(14) . . . . ? Cl1 Al1 N1 C1 -100.6(13) . . . . ? N6 Al1 N1 C1' 126.3(4) . . . . ? Cl2 Al1 N1 C1' 6.2(5) . . . . ? Cl1 Al1 N1 C1' -112.1(4) . . . . ? N4 Al2 N3 C4 -60.1(4) . . . . ? Cl4 Al2 N3 C4 178.7(3) . . . . ? Cl3 Al2 N3 C4 64.1(3) . . . . ? N4 Al2 N3 C7 132.1(3) . . . . ? Cl4 Al2 N3 C7 11.0(4) . . . . ? Cl3 Al2 N3 C7 -103.7(3) . . . . ? N3 Al2 N4 C13 -57.0(4) . . . . ? Cl4 Al2 N4 C13 68.0(3) . . . . ? Cl3 Al2 N4 C13 -177.5(3) . . . . ? N3 Al2 N4 C10' 133.2(7) . . . . ? Cl4 Al2 N4 C10' -101.8(7) . . . . ? Cl3 Al2 N4 C10' 12.7(7) . . . . ? N3 Al2 N4 C10 137.0(5) . . . . ? Cl4 Al2 N4 C10 -98.0(5) . . . . ? Cl3 Al2 N4 C10 16.5(6) . . . . ? N1 Al1 N6 C13 -58.9(4) . . . . ? Cl2 Al1 N6 C13 64.0(3) . . . . ? Cl1 Al1 N6 C13 -179.2(3) . . . . ? N1 Al1 N6 C16 130.3(3) . . . . ? Cl2 Al1 N6 C16 -106.8(3) . . . . ? Cl1 Al1 N6 C16 10.0(4) . . . . ? C4 N1 C1 C3 119.1(12) . . . . ? C1' N1 C1 C3 -56(2) . . . . ? Al1 N1 C1 C3 -80.6(18) . . . . ? C4 N1 C1 C2 -120.7(13) . . . . ? C1' N1 C1 C2 64(2) . . . . ? Al1 N1 C1 C2 40(2) . . . . ? C4 N1 C1' C2' -99.7(12) . . . . ? C1 N1 C1' C2' -94(3) . . . . ? Al1 N1 C1' C2' 69.1(11) . . . . ? C4 N1 C1' C3' 25.1(9) . . . . ? C1 N1 C1' C3' 31(2) . . . . ? Al1 N1 C1' C3' -166.1(5) . . . . ? C7 N3 C4 N2 29.7(6) . . . . ? Al2 N3 C4 N2 -139.1(4) . . . . ? C7 N3 C4 N1 -149.3(4) . . . . ? Al2 N3 C4 N1 41.9(4) . . . . ? C6 N2 C4 N3 40.3(7) . . . . ? C5 N2 C4 N3 -139.9(5) . . . . ? C6 N2 C4 N1 -140.8(5) . . . . ? C5 N2 C4 N1 39.0(7) . . . . ? C1 N1 C4 N3 -143.6(9) . . . . ? C1' N1 C4 N3 -140.9(6) . . . . ? Al1 N1 C4 N3 50.1(4) . . . . ? C1 N1 C4 N2 37.5(10) . . . . ? C1' N1 C4 N2 40.2(7) . . . . ? Al1 N1 C4 N2 -128.9(4) . . . . ? C4 N3 C7 C8 -119.8(5) . . . . ? Al2 N3 C7 C8 47.7(5) . . . . ? C4 N3 C7 C9 117.9(5) . . . . ? Al2 N3 C7 C9 -74.6(5) . . . . ? C13 N4 C10 C12 71(2) . . . . ? C10' N4 C10 C12 -115(3) . . . . ? Al2 N4 C10 C12 -123(2) . . . . ? C13 N4 C10 C11 -126.8(12) . . . . ? C10' N4 C10 C11 47.6(18) . . . . ? Al2 N4 C10 C11 39.8(13) . . . . ? C13 N4 C10' C11' -93(2) . . . . ? C10 N4 C10' C11' -101(3) . . . . ? Al2 N4 C10' C11' 73(2) . . . . ? C13 N4 C10' C12' 77.3(14) . . . . ? C10 N4 C10' C12' 69.5(17) . . . . ? Al2 N4 C10' C12' -116.5(11) . . . . ? C16 N6 C13 N5 36.8(7) . . . . ? Al1 N6 C13 N5 -133.8(4) . . . . ? C16 N6 C13 N4 -144.1(4) . . . . ? Al1 N6 C13 N4 45.4(5) . . . . ? C14 N5 C13 N6 -137.7(5) . . . . ? C15 N5 C13 N6 44.7(7) . . . . ? C14 N5 C13 N4 43.3(7) . . . . ? C15 N5 C13 N4 -134.4(6) . . . . ? C10' N4 C13 N6 -150.8(10) . . . . ? C10 N4 C13 N6 -146.8(5) . . . . ? Al2 N4 C13 N6 44.1(5) . . . . ? C10' N4 C13 N5 28.3(12) . . . . ? C10 N4 C13 N5 32.3(7) . . . . ? Al2 N4 C13 N5 -136.8(4) . . . . ? C13 N6 C16 C17 26.8(6) . . . . ? Al1 N6 C16 C17 -163.0(3) . . . . ? C13 N6 C16 C18 -103.9(5) . . . . ? Al1 N6 C16 C18 66.3(5) . . . . ? C24 C19 C20 C21 -2(3) . . . . ? C19 C20 C21 C22 -2(3) . . . . ? C20 C21 C22 C23 4(2) . . . . ? C21 C22 C23 C24 -2(3) . . . . ? C22 C23 C24 C19 -2(4) . . . . ? C22 C23 C24 C25 174(2) . . . . ? C20 C19 C24 C23 4(4) . . . . ? C20 C19 C24 C25 -172(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.785 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.096 # Attachment 'compound_3.cif' data_seab009 _database_code_depnum_ccdc_archive 'CCDC 644809' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H38 Al Cl N4' _chemical_formula_weight 372.95 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' 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' Cl Cl 0.1484 0.1585 '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 18.821(3) _cell_length_b 8.0375(13) _cell_length_c 15.060(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.269(2) _cell_angle_gamma 90.00 _cell_volume 2207.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 985 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.84 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type multi _exptl_absorpt_correction_T_min 0.8792 _exptl_absorpt_correction_T_max 0.9074 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 120(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 AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 8812 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.10 _reflns_number_total 2499 _reflns_number_gt 2261 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0602P)^2^+0.8074P] 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 2499 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0370 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0959 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _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 Al Al 1.0000 0.54828(5) 0.2500 0.01932(13) Uani 1 2 d S . . Cl Cl 1.0000 0.27540(5) 0.2500 0.03267(14) Uani 1 2 d S . . N1 N 0.89503(5) 0.57270(11) 0.18569(6) 0.0221(2) Uani 1 1 d . . . N2 N 0.98679(5) 0.68066(11) 0.14081(6) 0.0222(2) Uani 1 1 d . . . C1 C 0.82101(6) 0.50650(14) 0.17740(8) 0.0256(2) Uani 1 1 d . . . H1A H 0.7845 0.5940 0.1498 0.031 Uiso 1 1 calc R . . C2 C 0.80693(6) 0.35210(15) 0.11648(8) 0.0304(3) Uani 1 1 d . . . H2A H 0.8130 0.3802 0.0554 0.046 Uiso 1 1 calc R . . H2B H 0.7569 0.3123 0.1114 0.046 Uiso 1 1 calc R . . H2C H 0.8419 0.2647 0.1435 0.046 Uiso 1 1 calc R . . C3 C 0.81162(7) 0.46379(19) 0.27234(10) 0.0411(3) Uani 1 1 d . . . H3A H 0.8160 0.5653 0.3093 0.062 Uiso 1 1 calc R . . H3B H 0.8496 0.3844 0.3020 0.062 Uiso 1 1 calc R . . H3C H 0.7632 0.4141 0.2668 0.062 Uiso 1 1 calc R . . C4 C 1.02347(6) 0.79544(14) 0.09073(8) 0.0251(2) Uani 1 1 d . . . H4A H 0.9860 0.8762 0.0570 0.030 Uiso 1 1 calc R . . C5 C 1.05458(8) 0.70300(17) 0.02062(9) 0.0370(3) Uani 1 1 d . . . H5A H 1.0146 0.6487 -0.0241 0.055 Uiso 1 1 calc R . . H5B H 1.0896 0.6188 0.0518 0.055 Uiso 1 1 calc R . . H5C H 1.0796 0.7820 -0.0109 0.055 Uiso 1 1 calc R . . C6 C 1.08256(7) 0.89364(15) 0.15772(9) 0.0326(3) Uani 1 1 d . . . H6A H 1.0603 0.9549 0.2003 0.049 Uiso 1 1 calc R . . H6B H 1.1057 0.9723 0.1237 0.049 Uiso 1 1 calc R . . H6C H 1.1197 0.8168 0.1922 0.049 Uiso 1 1 calc R . . C7 C 0.91377(6) 0.66329(13) 0.12192(7) 0.0221(2) Uani 1 1 d . . . C8 C 0.86126(6) 0.74540(15) 0.04226(8) 0.0276(2) Uani 1 1 d . . . H8A H 0.8173 0.6747 0.0212 0.033 Uiso 1 1 calc R . . H8B H 0.8849 0.7583 -0.0092 0.033 Uiso 1 1 calc R . . C9 C 0.83862(7) 0.91621(15) 0.07089(9) 0.0333(3) Uani 1 1 d . . . H9A H 0.8090 0.9740 0.0171 0.050 Uiso 1 1 calc R . . H9B H 0.8826 0.9820 0.0975 0.050 Uiso 1 1 calc R . . H9C H 0.8098 0.9021 0.1164 0.050 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 Al 0.0214(2) 0.0188(2) 0.0195(2) 0.000 0.00817(16) 0.000 Cl 0.0362(2) 0.0189(2) 0.0403(3) 0.000 0.00462(17) 0.000 N1 0.0210(4) 0.0225(5) 0.0241(5) 0.0004(3) 0.0081(3) -0.0021(3) N2 0.0224(4) 0.0229(4) 0.0231(4) 0.0027(3) 0.0090(3) -0.0005(3) C1 0.0221(5) 0.0262(6) 0.0309(6) -0.0020(4) 0.0108(4) -0.0037(4) C2 0.0276(5) 0.0283(6) 0.0362(6) -0.0047(5) 0.0096(5) -0.0055(4) C3 0.0402(7) 0.0522(8) 0.0374(7) -0.0074(6) 0.0222(6) -0.0190(6) C4 0.0272(5) 0.0234(5) 0.0277(6) 0.0056(4) 0.0124(4) -0.0006(4) C5 0.0479(7) 0.0371(7) 0.0339(7) -0.0003(5) 0.0251(6) -0.0058(5) C6 0.0349(6) 0.0263(6) 0.0400(7) -0.0008(5) 0.0156(5) -0.0072(5) C7 0.0248(5) 0.0202(5) 0.0225(5) -0.0021(4) 0.0081(4) -0.0003(4) C8 0.0255(5) 0.0295(6) 0.0269(6) 0.0036(4) 0.0045(4) -0.0009(4) C9 0.0304(6) 0.0289(6) 0.0406(7) 0.0083(5) 0.0086(5) 0.0052(4) _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 N2 1.9225(10) 2_755 ? Al N2 1.9226(10) . ? Al N1 1.9841(9) . ? Al N1 1.9841(9) 2_755 ? Al Cl 2.1933(7) . ? Al C7 2.3802(11) 2_755 ? Al C7 2.3803(11) . ? N1 C7 1.3205(14) . ? N1 C1 1.4674(13) . ? N2 C7 1.3404(13) . ? N2 C4 1.4673(13) . ? C1 C3 1.5225(17) . ? C1 C2 1.5271(16) . ? C4 C5 1.5213(16) . ? C4 C6 1.5246(16) . ? C7 C8 1.5057(15) . ? C8 C9 1.5305(17) . ? 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 N2 Al N2 112.79(6) 2_755 . ? N2 Al N1 105.43(4) 2_755 . ? N2 Al N1 67.94(4) . . ? N2 Al N1 67.95(4) 2_755 2_755 ? N2 Al N1 105.43(4) . 2_755 ? N1 Al N1 168.65(6) . 2_755 ? N2 Al Cl 123.60(3) 2_755 . ? N2 Al Cl 123.60(3) . . ? N1 Al Cl 95.68(3) . . ? N1 Al Cl 95.68(3) 2_755 . ? N2 Al C7 34.25(4) 2_755 2_755 ? N2 Al C7 113.37(4) . 2_755 ? N1 Al C7 139.04(4) . 2_755 ? N1 Al C7 33.70(4) 2_755 2_755 ? Cl Al C7 112.85(3) . 2_755 ? N2 Al C7 113.37(4) 2_755 . ? N2 Al C7 34.25(4) . . ? N1 Al C7 33.69(4) . . ? N1 Al C7 139.04(4) 2_755 . ? Cl Al C7 112.85(3) . . ? C7 Al C7 134.29(5) 2_755 . ? C7 N1 C1 123.79(9) . . ? C7 N1 Al 89.84(6) . . ? C1 N1 Al 144.67(8) . . ? C7 N2 C4 122.96(9) . . ? C7 N2 Al 91.92(6) . . ? C4 N2 Al 144.05(7) . . ? N1 C1 C3 109.23(9) . . ? N1 C1 C2 111.49(9) . . ? C3 C1 C2 109.74(10) . . ? N2 C4 C5 111.10(9) . . ? N2 C4 C6 110.13(9) . . ? C5 C4 C6 111.67(10) . . ? N1 C7 N2 110.29(9) . . ? N1 C7 C8 125.49(9) . . ? N2 C7 C8 124.11(10) . . ? N1 C7 Al 56.46(6) . . ? N2 C7 Al 53.83(5) . . ? C8 C7 Al 176.78(8) . . ? C7 C8 C9 110.02(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Al N1 C7 109.14(7) 2_755 . . . ? N2 Al N1 C7 0.37(6) . . . . ? N1 Al N1 C7 56.32(6) 2_755 . . . ? Cl Al N1 C7 -123.67(6) . . . . ? C7 Al N1 C7 101.10(10) 2_755 . . . ? N2 Al N1 C1 -87.56(13) 2_755 . . . ? N2 Al N1 C1 163.67(14) . . . . ? N1 Al N1 C1 -140.39(13) 2_755 . . . ? Cl Al N1 C1 39.62(13) . . . . ? C7 Al N1 C1 -95.60(14) 2_755 . . . ? C7 Al N1 C1 163.29(16) . . . . ? N2 Al N2 C7 -98.48(6) 2_755 . . . ? N1 Al N2 C7 -0.37(6) . . . . ? N1 Al N2 C7 -170.63(6) 2_755 . . . ? Cl Al N2 C7 81.52(6) . . . . ? C7 Al N2 C7 -135.81(7) 2_755 . . . ? N2 Al N2 C4 68.32(12) 2_755 . . . ? N1 Al N2 C4 166.43(14) . . . . ? N1 Al N2 C4 -3.83(14) 2_755 . . . ? Cl Al N2 C4 -111.69(12) . . . . ? C7 Al N2 C4 30.98(14) 2_755 . . . ? C7 Al N2 C4 166.79(17) . . . . ? C7 N1 C1 C3 -160.07(11) . . . . ? Al N1 C1 C3 40.16(17) . . . . ? C7 N1 C1 C2 78.47(13) . . . . ? Al N1 C1 C2 -81.29(15) . . . . ? C7 N2 C4 C5 -101.49(12) . . . . ? Al N2 C4 C5 94.30(15) . . . . ? C7 N2 C4 C6 134.25(11) . . . . ? Al N2 C4 C6 -29.96(17) . . . . ? C1 N1 C7 N2 -168.99(9) . . . . ? Al N1 C7 N2 -0.53(9) . . . . ? C1 N1 C7 C8 14.65(17) . . . . ? Al N1 C7 C8 -176.89(10) . . . . ? C1 N1 C7 Al -168.46(11) . . . . ? C4 N2 C7 N1 -170.25(10) . . . . ? Al N2 C7 N1 0.55(9) . . . . ? C4 N2 C7 C8 6.17(16) . . . . ? Al N2 C7 C8 176.97(10) . . . . ? C4 N2 C7 Al -170.80(12) . . . . ? N2 Al C7 N1 -82.77(7) 2_755 . . . ? N2 Al C7 N1 -179.38(10) . . . . ? N1 Al C7 N1 -165.53(7) 2_755 . . . ? Cl Al C7 N1 63.99(6) . . . . ? C7 Al C7 N1 -116.01(6) 2_755 . . . ? N2 Al C7 N2 96.61(8) 2_755 . . . ? N1 Al C7 N2 179.38(10) . . . . ? N1 Al C7 N2 13.86(9) 2_755 . . . ? Cl Al C7 N2 -116.63(6) . . . . ? C7 Al C7 N2 63.37(6) 2_755 . . . ? N2 Al C7 C8 45.5(14) 2_755 . . . ? N2 Al C7 C8 -51.1(14) . . . . ? N1 Al C7 C8 128.3(14) . . . . ? N1 Al C7 C8 -37.2(14) 2_755 . . . ? Cl Al C7 C8 -167.7(14) . . . . ? C7 Al C7 C8 12.3(14) 2_755 . . . ? N1 C7 C8 C9 86.12(13) . . . . ? N2 C7 C8 C9 -89.76(13) . . . . ? Al C7 C8 C9 -40.4(14) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.341 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.048 data_seab011 _database_code_depnum_ccdc_archive 'CCDC 644810' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H34 Cl Ga N4' _chemical_formula_weight 387.64 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' Cl Cl 0.1484 0.1585 '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 11.505(8) _cell_length_b 12.788(8) _cell_length_c 14.102(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.130(9) _cell_angle_gamma 90.00 _cell_volume 1972(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 938 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 28.01 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.55 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.534 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4241 _exptl_absorpt_correction_T_max 0.4880 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; Data collection is performed with four batch runs at \f = 0.00 \% (600 frames), at \f = 90.00 \% (600 frames), at \f = 180 \% (600 frames) and at \f = 270 \% (600 frames). Frame width = 0.30 \& in \w. Data is merged, corrected for decay, and treated with multi-scan absorption corrections. ; _diffrn_ambient_temperature 120(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 AXS APEX diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 836.6 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 1 _diffrn_reflns_number 7012 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.17 _reflns_number_total 2206 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2001)' _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^)+(0.0545P)^2^] 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 2206 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0842 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Ga Ga 0.5000 0.240534(18) 0.2500 0.01915(11) Uani 1 2 d S . . Cl Cl 0.5000 0.41276(4) 0.2500 0.02868(16) Uani 1 2 d S . . N1 N 0.64898(12) 0.16481(10) 0.32134(10) 0.0218(3) Uani 1 1 d . . . N2 N 0.52595(12) 0.21547(12) 0.40447(10) 0.0209(3) Uani 1 1 d . . . C1 C 0.62711(14) 0.16473(12) 0.40967(12) 0.0209(3) Uani 1 1 d . . . C2 C 0.70998(15) 0.11249(14) 0.50141(11) 0.0258(3) Uani 1 1 d . . . H2A H 0.6995 0.1453 0.5610 0.039 Uiso 1 1 calc R . . H2B H 0.7952 0.1200 0.5025 0.039 Uiso 1 1 calc R . . H2C H 0.6892 0.0381 0.5005 0.039 Uiso 1 1 calc R . . C3 C 0.73791(14) 0.09697(12) 0.29662(11) 0.0227(3) Uani 1 1 d . . . H3A H 0.7995 0.0737 0.3603 0.027 Uiso 1 1 calc R . . C4 C 0.80395(16) 0.15855(15) 0.23686(14) 0.0315(4) Uani 1 1 d . . . H4A H 0.8435 0.2198 0.2753 0.047 Uiso 1 1 calc R . . H4B H 0.7450 0.1815 0.1739 0.047 Uiso 1 1 calc R . . H4C H 0.8660 0.1141 0.2228 0.047 Uiso 1 1 calc R . . C5 C 0.67462(16) 0.00001(15) 0.24013(14) 0.0331(4) Uani 1 1 d . . . H5A H 0.6330 -0.0376 0.2808 0.050 Uiso 1 1 calc R . . H5B H 0.7357 -0.0458 0.2264 0.050 Uiso 1 1 calc R . . H5C H 0.6146 0.0214 0.1770 0.050 Uiso 1 1 calc R . . C6 C 0.49738(17) 0.24978(12) 0.49436(14) 0.0250(4) Uani 1 1 d . . . H6A H 0.5764 0.2650 0.5473 0.030 Uiso 1 1 calc R . . C7 C 0.43004(17) 0.16605(15) 0.53453(14) 0.0334(4) Uani 1 1 d . . . H7A H 0.4792 0.1020 0.5486 0.050 Uiso 1 1 calc R . . H7B H 0.3509 0.1513 0.4847 0.050 Uiso 1 1 calc R . . H7C H 0.4169 0.1912 0.5960 0.050 Uiso 1 1 calc R . . C8 C 0.42384(17) 0.35056(16) 0.47216(15) 0.0346(4) Uani 1 1 d . . . H8A H 0.4686 0.4030 0.4466 0.052 Uiso 1 1 calc R . . H8B H 0.4110 0.3766 0.5335 0.052 Uiso 1 1 calc R . . H8C H 0.3445 0.3371 0.4221 0.052 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 Ga 0.01834(15) 0.02099(17) 0.01710(16) 0.000 0.00406(11) 0.000 Cl 0.0337(3) 0.0205(3) 0.0340(3) 0.000 0.0137(2) 0.000 N1 0.0220(6) 0.0249(7) 0.0164(6) 0.0000(5) 0.0031(5) 0.0035(5) N2 0.0227(6) 0.0242(7) 0.0156(6) -0.0025(5) 0.0058(5) -0.0031(5) C1 0.0230(7) 0.0199(8) 0.0185(8) -0.0023(6) 0.0044(6) -0.0061(6) C2 0.0261(7) 0.0293(9) 0.0194(8) 0.0030(6) 0.0033(6) -0.0019(7) C3 0.0221(7) 0.0263(8) 0.0186(7) -0.0005(6) 0.0045(6) 0.0037(6) C4 0.0283(8) 0.0380(10) 0.0294(9) 0.0009(7) 0.0107(7) 0.0037(7) C5 0.0329(8) 0.0299(9) 0.0362(10) -0.0100(8) 0.0102(7) 0.0007(7) C6 0.0243(8) 0.0341(10) 0.0182(8) -0.0059(6) 0.0089(7) -0.0061(6) C7 0.0343(9) 0.0433(12) 0.0264(9) 0.0027(7) 0.0147(8) -0.0037(7) C8 0.0411(10) 0.0348(10) 0.0337(10) -0.0082(8) 0.0201(8) -0.0013(8) _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 Ga N1 1.9531(16) 2_655 ? Ga N1 1.9531(16) . ? Ga N2 2.1288(19) . ? Ga N2 2.1289(19) 2_655 ? Ga Cl 2.2025(16) . ? Ga C1 2.4696(19) 2_655 ? Ga C1 2.4696(19) . ? N1 C1 1.345(2) . ? N1 C3 1.464(2) . ? N2 C1 1.315(2) . ? N2 C6 1.472(2) . ? C1 C2 1.504(2) . ? C3 C4 1.519(3) . ? C3 C5 1.530(2) . ? C6 C8 1.520(3) . ? C6 C7 1.530(2) . ? 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 Ga N1 120.55(9) 2_655 . ? N1 Ga N2 105.87(6) 2_655 . ? N1 Ga N2 64.99(6) . . ? N1 Ga N2 64.99(6) 2_655 2_655 ? N1 Ga N2 105.87(6) . 2_655 ? N2 Ga N2 162.68(8) . 2_655 ? N1 Ga Cl 119.73(4) 2_655 . ? N1 Ga Cl 119.72(4) . . ? N2 Ga Cl 98.66(4) . . ? N2 Ga Cl 98.66(4) 2_655 . ? N1 Ga C1 32.86(5) 2_655 2_655 ? N1 Ga C1 116.79(6) . 2_655 ? N2 Ga C1 136.76(6) . 2_655 ? N2 Ga C1 32.14(6) 2_655 2_655 ? Cl Ga C1 113.11(4) . 2_655 ? N1 Ga C1 116.79(6) 2_655 . ? N1 Ga C1 32.86(5) . . ? N2 Ga C1 32.15(6) . . ? N2 Ga C1 136.76(6) 2_655 . ? Cl Ga C1 113.11(4) . . ? C1 Ga C1 133.78(8) 2_655 . ? C1 N1 C3 124.47(13) . . ? C1 N1 Ga 95.18(10) . . ? C3 N1 Ga 137.53(11) . . ? C1 N2 C6 122.02(14) . . ? C1 N2 Ga 88.35(10) . . ? C6 N2 Ga 146.98(12) . . ? N2 C1 N1 111.43(14) . . ? N2 C1 C2 125.50(15) . . ? N1 C1 C2 123.07(15) . . ? N2 C1 Ga 59.50(9) . . ? N1 C1 Ga 51.96(9) . . ? C2 C1 Ga 174.74(12) . . ? N1 C3 C4 109.41(14) . . ? N1 C3 C5 110.46(13) . . ? C4 C3 C5 111.75(15) . . ? N2 C6 C8 109.55(15) . . ? N2 C6 C7 112.62(14) . . ? C8 C6 C7 110.86(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Ga N1 C1 -92.92(9) 2_655 . . . ? N2 Ga N1 C1 1.39(8) . . . . ? N2 Ga N1 C1 -162.88(9) 2_655 . . . ? Cl Ga N1 C1 87.08(9) . . . . ? C1 Ga N1 C1 -130.29(10) 2_655 . . . ? N1 Ga N1 C3 67.24(15) 2_655 . . . ? N2 Ga N1 C3 161.54(17) . . . . ? N2 Ga N1 C3 -2.72(17) 2_655 . . . ? Cl Ga N1 C3 -112.76(15) . . . . ? C1 Ga N1 C3 29.86(17) 2_655 . . . ? C1 Ga N1 C3 160.2(2) . . . . ? N1 Ga N2 C1 115.36(10) 2_655 . . . ? N1 Ga N2 C1 -1.41(9) . . . . ? N2 Ga N2 C1 59.74(9) 2_655 . . . ? Cl Ga N2 C1 -120.25(9) . . . . ? C1 Ga N2 C1 101.88(14) 2_655 . . . ? N1 Ga N2 C6 -86.4(2) 2_655 . . . ? N1 Ga N2 C6 156.9(2) . . . . ? N2 Ga N2 C6 -142.0(2) 2_655 . . . ? Cl Ga N2 C6 38.0(2) . . . . ? C1 Ga N2 C6 -99.8(2) 2_655 . . . ? C1 Ga N2 C6 158.3(2) . . . . ? C6 N2 C1 N1 -164.24(14) . . . . ? Ga N2 C1 N1 2.00(12) . . . . ? C6 N2 C1 C2 15.7(2) . . . . ? Ga N2 C1 C2 -178.05(14) . . . . ? C6 N2 C1 Ga -166.24(16) . . . . ? C3 N1 C1 N2 -166.04(14) . . . . ? Ga N1 C1 N2 -2.18(13) . . . . ? C3 N1 C1 C2 14.0(2) . . . . ? Ga N1 C1 C2 177.86(13) . . . . ? C3 N1 C1 Ga -163.86(17) . . . . ? N1 Ga C1 N2 -76.84(11) 2_655 . . . ? N1 Ga C1 N2 177.64(14) . . . . ? N2 Ga C1 N2 -157.95(11) 2_655 . . . ? Cl Ga C1 N2 68.20(10) . . . . ? C1 Ga C1 N2 -111.81(10) 2_655 . . . ? N1 Ga C1 N1 105.52(12) 2_655 . . . ? N2 Ga C1 N1 -177.64(14) . . . . ? N2 Ga C1 N1 24.41(13) 2_655 . . . ? Cl Ga C1 N1 -109.44(9) . . . . ? C1 Ga C1 N1 70.55(9) 2_655 . . . ? N1 Ga C1 C2 85.6(12) 2_655 . . . ? N1 Ga C1 C2 -19.9(12) . . . . ? N2 Ga C1 C2 162.4(13) . . . . ? N2 Ga C1 C2 4.5(13) 2_655 . . . ? Cl Ga C1 C2 -129.4(12) . . . . ? C1 Ga C1 C2 50.6(12) 2_655 . . . ? C1 N1 C3 C4 -140.05(15) . . . . ? Ga N1 C3 C4 64.2(2) . . . . ? C1 N1 C3 C5 96.53(18) . . . . ? Ga N1 C3 C5 -59.3(2) . . . . ? C1 N2 C6 C8 148.21(16) . . . . ? Ga N2 C6 C8 -5.9(3) . . . . ? C1 N2 C6 C7 -87.9(2) . . . . ? Ga N2 C6 C7 117.95(19) . . . . ? _diffrn_measured_fraction_theta_max 0.909 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.458 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.064