Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Jones, Cameron' 'Baker, Robert J.' 'Cole, Marcus L.' 'Mahon, M.' _publ_contact_author_name 'Dr Cameron Jones' _publ_contact_author_address ; Department of Chemistry University of Wales P.O. Box 912 Park Place Cardiff CF10 3TB UNITED KINGDOM ; _publ_contact_author_email 'JONESCA6@CARDIFF.AC.UK' _publ_section_title ; Bidentate N-Heterocyclic Carbene Complexes of Group 13 Trihydrides and Trihalides ; data_cmpd11 _database_code_CSD 177618 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H30 Cl4 N4' _chemical_formula_weight 432.25 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' _symmetry_cell_setting orthorhombic _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 13.401(3) _cell_length_b 15.748(3) _cell_length_c 11.461(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.40(3) _cell_angle_gamma 90.00 _cell_volume 2281.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.527 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _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 14903 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 26.09 _reflns_number_total 2244 _reflns_number_gt 2004 _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^)+(0.0303P)^2^+1.9135P] 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 2244 _refine_ls_number_parameters 117 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0771 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 Cl1 Cl 0.17839(3) 0.33863(2) 0.58872(3) 0.02327(12) Uani 1 1 d . . . Cl2 Cl -0.59168(5) 0.26362(4) 0.13628(6) 0.0686(2) Uani 1 1 d . . . N1 N -0.21279(9) 0.41879(7) 0.22326(10) 0.0187(3) Uani 1 1 d . . . N2 N -0.09034(9) 0.32442(7) 0.29077(11) 0.0211(3) Uani 1 1 d . . . C1 C -0.18497(11) 0.33999(9) 0.20670(13) 0.0197(3) Uani 1 1 d . . . H1 H -0.2245 0.3021 0.1469 0.024 Uiso 1 1 calc R . . C2 C -0.13316(11) 0.45482(9) 0.32100(13) 0.0240(3) Uani 1 1 d . . . H2 H -0.1326 0.5095 0.3519 0.029 Uiso 1 1 calc R . . C3 C -0.05687(12) 0.39595(10) 0.36278(14) 0.0258(3) Uani 1 1 d . . . H3 H 0.0064 0.4022 0.4278 0.031 Uiso 1 1 calc R . . C4 C -0.02788(12) 0.24702(9) 0.29817(14) 0.0252(3) Uani 1 1 d . . . H4A H -0.0740 0.1979 0.2853 0.030 Uiso 1 1 calc R . . H4B H 0.0244 0.2426 0.3801 0.030 Uiso 1 1 calc R . . C5 C -0.31164(11) 0.46413(9) 0.14817(12) 0.0202(3) Uani 1 1 d . . . C6 C -0.27821(13) 0.54033(10) 0.08743(14) 0.0284(3) Uani 1 1 d . . . H6A H -0.2376 0.5788 0.1502 0.043 Uiso 1 1 calc R . . H6B H -0.3400 0.5689 0.0345 0.043 Uiso 1 1 calc R . . H6C H -0.2360 0.5212 0.0393 0.043 Uiso 1 1 calc R . . C7 C -0.36912(12) 0.49254(10) 0.23609(14) 0.0264(3) Uani 1 1 d . . . H7A H -0.3855 0.4438 0.2767 0.040 Uiso 1 1 calc R . . H7B H -0.4334 0.5212 0.1901 0.040 Uiso 1 1 calc R . . H7C H -0.3246 0.5305 0.2968 0.040 Uiso 1 1 calc R . . C8 C -0.37975(12) 0.40257(10) 0.05154(14) 0.0269(3) Uani 1 1 d . . . H8A H -0.3418 0.3847 -0.0019 0.040 Uiso 1 1 calc R . . H8B H -0.4441 0.4303 0.0036 0.040 Uiso 1 1 calc R . . H8C H -0.3963 0.3539 0.0922 0.040 Uiso 1 1 calc R . . C9 C -0.5000 0.20117(17) 0.2500 0.0488(7) Uani 1 2 d S . . H9A H -0.5379 0.1649 0.2894 0.059 Uiso 0.50 1 calc PR . . H9B H -0.4621 0.1649 0.2106 0.059 Uiso 0.50 1 calc PR . . 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 Cl1 0.0243(2) 0.02000(19) 0.0244(2) -0.00013(13) 0.00658(14) 0.00337(13) Cl2 0.0739(4) 0.0560(4) 0.0873(4) 0.0164(3) 0.0422(3) 0.0082(3) N1 0.0167(6) 0.0191(6) 0.0190(6) -0.0009(5) 0.0041(5) -0.0003(5) N2 0.0196(6) 0.0170(6) 0.0240(6) 0.0010(5) 0.0039(5) 0.0000(5) C1 0.0180(7) 0.0192(7) 0.0208(7) -0.0003(5) 0.0051(5) -0.0015(5) C2 0.0222(7) 0.0221(7) 0.0233(7) -0.0062(6) 0.0016(6) -0.0010(6) C3 0.0215(7) 0.0248(8) 0.0253(7) -0.0042(6) -0.0003(6) -0.0008(6) C4 0.0230(8) 0.0155(7) 0.0332(8) 0.0040(6) 0.0044(6) 0.0014(6) C5 0.0172(7) 0.0225(7) 0.0185(7) 0.0012(6) 0.0026(5) 0.0031(6) C6 0.0300(8) 0.0281(8) 0.0258(8) 0.0054(6) 0.0073(6) 0.0025(7) C7 0.0213(7) 0.0326(9) 0.0246(7) -0.0014(6) 0.0069(6) 0.0046(6) C8 0.0203(7) 0.0300(8) 0.0253(8) -0.0033(6) 0.0009(6) 0.0027(6) C9 0.0585(18) 0.0337(14) 0.0706(19) 0.000 0.0436(16) 0.000 _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 Cl2 C9 1.7639(17) . ? N1 C1 1.3274(18) . ? N1 C2 1.3862(18) . ? N1 C5 1.4993(18) . ? N2 C1 1.3360(19) . ? N2 C3 1.3804(19) . ? N2 C4 1.4650(18) . ? C2 C3 1.345(2) . ? C4 C4 1.525(3) 2 ? C5 C7 1.525(2) . ? C5 C8 1.526(2) . ? C5 C6 1.527(2) . ? C9 Cl2 1.7639(17) 2_455 ? 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 C1 N1 C2 108.71(12) . . ? C1 N1 C5 126.85(12) . . ? C2 N1 C5 124.41(12) . . ? C1 N2 C3 108.88(12) . . ? C1 N2 C4 125.56(12) . . ? C3 N2 C4 125.34(12) . . ? N1 C1 N2 108.23(12) . . ? C3 C2 N1 107.20(13) . . ? C2 C3 N2 106.98(12) . . ? N2 C4 C4 111.47(10) . 2 ? N1 C5 C7 107.72(11) . . ? N1 C5 C8 108.40(12) . . ? C7 C5 C8 110.76(12) . . ? N1 C5 C6 107.40(11) . . ? C7 C5 C6 111.08(12) . . ? C8 C5 C6 111.33(12) . . ? Cl2 C9 Cl2 112.23(16) 2_455 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.236 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.055 data_cmpd9 _database_code_CSD 177619 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H30 Br3 Cl4 In N4' _chemical_formula_weight 798.81 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'In' 'In' -0.7276 1.3100 '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.0470(3) _cell_length_b 14.3610(3) _cell_length_c 16.8110(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.8870(10) _cell_angle_gamma 90.00 _cell_volume 2797.33(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1552 _exptl_absorpt_coefficient_mu 5.526 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.41 _exptl_absorpt_correction_T_max 0.49 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32746 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6384 _reflns_number_gt 4943 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+16.3297P] 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 SHELXL _refine_ls_extinction_coef 0.00132(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 6384 _refine_ls_number_parameters 278 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group In1 In 0.20076(3) 0.25663(3) 0.12037(3) 0.02140(12) Uani 1 1 d . . . Br1 Br 0.22676(5) 0.18284(4) -0.02304(4) 0.02799(16) Uani 1 1 d . . . Br3 Br 0.17547(5) 0.32001(4) 0.26846(4) 0.02796(16) Uani 1 1 d . . . Br2 Br 0.21596(6) 0.42058(4) 0.06816(4) 0.03105(17) Uani 1 1 d . . . Cl1 Cl 0.42558(15) -0.00048(13) 0.07570(11) 0.0430(4) Uani 1 1 d . . . Cl2 Cl 0.66638(18) -0.02263(18) 0.17070(15) 0.0648(6) Uani 1 1 d . . . Cl3 Cl 0.5369(2) -0.33413(19) 0.1670(2) 0.0850(9) Uani 1 1 d . . . Cl4 Cl 0.6730(2) -0.48283(16) 0.12303(17) 0.0676(6) Uani 1 1 d . . . N1 N -0.0770(4) 0.1934(3) 0.0578(3) 0.0264(11) Uani 1 1 d . . . N2 N 0.0419(4) 0.0829(3) 0.1069(3) 0.0266(11) Uani 1 1 d . . . N3 N 0.4654(4) 0.1890(3) 0.2253(3) 0.0245(10) Uani 1 1 d . . . N4 N 0.3275(4) 0.0996(3) 0.2366(3) 0.0253(10) Uani 1 1 d . . . C1 C 0.0365(5) 0.1751(4) 0.0925(4) 0.0239(12) Uani 1 1 d . . . C2 C -0.1400(5) 0.1114(5) 0.0499(4) 0.0344(15) Uani 1 1 d . . . H2 H -0.2209 0.1051 0.0267 0.041 Uiso 1 1 calc R . . C3 C -0.0651(6) 0.0424(5) 0.0812(4) 0.0385(16) Uani 1 1 d . . . H3 H -0.0828 -0.0216 0.0847 0.046 Uiso 1 1 calc R . . C4 C 0.1495(5) 0.0308(4) 0.1419(4) 0.0284(13) Uani 1 1 d . . . H4A H 0.2015 0.0396 0.1060 0.034 Uiso 1 1 calc R . . H4B H 0.1313 -0.0364 0.1422 0.034 Uiso 1 1 calc R . . C5 C 0.2117(5) 0.0614(4) 0.2296(4) 0.0269(13) Uani 1 1 d . . . H5A H 0.1647 0.1092 0.2477 0.032 Uiso 1 1 calc R . . H5B H 0.2189 0.0073 0.2672 0.032 Uiso 1 1 calc R . . C6 C 0.4273(6) 0.0611(4) 0.2860(4) 0.0318(14) Uani 1 1 d . . . H6 H 0.4338 0.0062 0.3184 0.038 Uiso 1 1 calc R . . C7 C 0.5143(5) 0.1176(4) 0.2790(4) 0.0312(14) Uani 1 1 d . . . H7 H 0.5940 0.1096 0.3059 0.037 Uiso 1 1 calc R . . C8 C 0.3506(5) 0.1772(4) 0.1986(4) 0.0232(12) Uani 1 1 d . . . C9 C -0.1282(5) 0.2870(4) 0.0267(4) 0.0302(14) Uani 1 1 d . . . C10 C -0.0921(6) 0.3572(5) 0.0978(4) 0.0372(16) Uani 1 1 d . . . H10A H -0.1172 0.3347 0.1452 0.056 Uiso 1 1 calc R . . H10B H -0.1281 0.4176 0.0798 0.056 Uiso 1 1 calc R . . H10C H -0.0080 0.3640 0.1140 0.056 Uiso 1 1 calc R . . C11 C -0.0840(6) 0.3136(5) -0.0468(4) 0.0353(15) Uani 1 1 d . . . H11A H 0.0006 0.3116 -0.0305 0.053 Uiso 1 1 calc R . . H11B H -0.1100 0.3766 -0.0651 0.053 Uiso 1 1 calc R . . H11C H -0.1140 0.2696 -0.0922 0.053 Uiso 1 1 calc R . . C12 C -0.2593(6) 0.2791(6) -0.0003(5) 0.0406(17) Uani 1 1 d . . . H12A H -0.2827 0.2347 -0.0462 0.061 Uiso 1 1 calc R . . H12B H -0.2930 0.3403 -0.0184 0.061 Uiso 1 1 calc R . . H12C H -0.2867 0.2573 0.0462 0.061 Uiso 1 1 calc R . . C13 C 0.5342(5) 0.2692(4) 0.2051(4) 0.0247(12) Uani 1 1 d . . . C14 C 0.5009(5) 0.3561(5) 0.2470(4) 0.0328(14) Uani 1 1 d . . . H14A H 0.4176 0.3666 0.2265 0.049 Uiso 1 1 calc R . . H14B H 0.5422 0.4104 0.2342 0.049 Uiso 1 1 calc R . . H14C H 0.5218 0.3467 0.3070 0.049 Uiso 1 1 calc R . . C15 C 0.5023(6) 0.2802(5) 0.1116(4) 0.0352(15) Uani 1 1 d . . . H15A H 0.5209 0.2226 0.0866 0.053 Uiso 1 1 calc R . . H15B H 0.5460 0.3320 0.0972 0.053 Uiso 1 1 calc R . . H15C H 0.4195 0.2929 0.0908 0.053 Uiso 1 1 calc R . . C16 C 0.6620(5) 0.2498(5) 0.2388(5) 0.0382(16) Uani 1 1 d . . . H16A H 0.6814 0.2438 0.2992 0.057 Uiso 1 1 calc R . . H16B H 0.7061 0.3012 0.2242 0.057 Uiso 1 1 calc R . . H16C H 0.6812 0.1917 0.2150 0.057 Uiso 1 1 calc R . . C17 C 0.5385(6) -0.0790(6) 0.1189(5) 0.0457(18) Uani 1 1 d . . . H17A H 0.5144 -0.1205 0.1582 0.055 Uiso 1 1 calc R . . H17B H 0.5529 -0.1181 0.0743 0.055 Uiso 1 1 calc R . . C18 C 0.5897(9) -0.3824(7) 0.0899(6) 0.066(3) Uani 1 1 d . . . H18A H 0.6375 -0.3356 0.0714 0.079 Uiso 1 1 calc R . . H18B H 0.5241 -0.3985 0.0419 0.079 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 In1 0.0237(2) 0.0158(2) 0.0244(2) 0.00060(15) 0.00618(15) -0.00017(15) Br1 0.0330(3) 0.0254(3) 0.0263(3) -0.0042(2) 0.0092(2) -0.0019(2) Br3 0.0350(3) 0.0246(3) 0.0252(3) -0.0010(2) 0.0097(2) 0.0024(2) Br2 0.0441(4) 0.0177(3) 0.0329(3) 0.0033(2) 0.0131(3) -0.0007(2) Cl1 0.0387(9) 0.0491(10) 0.0440(10) 0.0003(8) 0.0160(8) 0.0080(8) Cl2 0.0465(11) 0.0759(15) 0.0652(14) -0.0266(12) 0.0036(10) 0.0187(10) Cl3 0.0601(15) 0.0685(16) 0.135(3) -0.0218(17) 0.0417(16) -0.0003(12) Cl4 0.0700(14) 0.0503(12) 0.0918(18) 0.0154(12) 0.0381(13) 0.0087(11) N1 0.026(3) 0.024(3) 0.026(3) -0.001(2) 0.004(2) -0.002(2) N2 0.030(3) 0.017(2) 0.032(3) 0.000(2) 0.007(2) -0.001(2) N3 0.027(3) 0.022(2) 0.026(3) -0.0014(19) 0.009(2) -0.001(2) N4 0.028(3) 0.023(2) 0.024(3) 0.004(2) 0.007(2) 0.002(2) C1 0.031(3) 0.018(3) 0.024(3) -0.001(2) 0.009(2) -0.002(2) C2 0.023(3) 0.036(4) 0.039(4) -0.002(3) 0.000(3) -0.007(3) C3 0.037(4) 0.031(3) 0.044(4) -0.001(3) 0.006(3) -0.012(3) C4 0.029(3) 0.016(3) 0.038(4) 0.002(2) 0.007(3) -0.001(2) C5 0.031(3) 0.020(3) 0.030(3) 0.006(2) 0.008(3) -0.002(2) C6 0.038(3) 0.024(3) 0.033(3) 0.004(3) 0.008(3) 0.008(3) C7 0.027(3) 0.024(3) 0.038(4) 0.004(3) 0.001(3) 0.006(2) C8 0.027(3) 0.016(3) 0.025(3) 0.000(2) 0.005(2) 0.002(2) C9 0.030(3) 0.023(3) 0.035(4) -0.001(3) 0.004(3) 0.004(2) C10 0.033(3) 0.037(4) 0.034(4) -0.007(3) -0.003(3) 0.014(3) C11 0.033(3) 0.037(4) 0.034(4) 0.009(3) 0.008(3) 0.006(3) C12 0.028(3) 0.053(5) 0.038(4) -0.005(3) 0.005(3) 0.009(3) C13 0.027(3) 0.026(3) 0.023(3) -0.001(2) 0.011(2) 0.000(2) C14 0.030(3) 0.034(3) 0.035(4) -0.008(3) 0.010(3) -0.007(3) C15 0.030(3) 0.041(4) 0.034(4) -0.001(3) 0.008(3) -0.006(3) C16 0.026(3) 0.043(4) 0.045(4) -0.006(3) 0.011(3) -0.004(3) C17 0.049(4) 0.043(4) 0.047(5) 0.005(3) 0.017(4) 0.008(3) C18 0.072(6) 0.057(6) 0.068(6) 0.016(5) 0.017(5) 0.003(5) _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 In1 C8 2.233(6) . ? In1 C1 2.236(6) . ? In1 Br2 2.5367(7) . ? In1 Br1 2.7290(7) . ? In1 Br3 2.7449(7) . ? Cl1 C17 1.763(8) . ? Cl2 C17 1.747(8) . ? Cl3 C18 1.737(11) . ? Cl4 C18 1.758(9) . ? N1 C1 1.357(8) . ? N1 C2 1.388(8) . ? N1 C9 1.512(8) . ? N2 C1 1.345(7) . ? N2 C3 1.371(8) . ? N2 C4 1.472(7) . ? N3 C8 1.344(7) . ? N3 C7 1.387(8) . ? N3 C13 1.510(7) . ? N4 C8 1.351(7) . ? N4 C6 1.376(8) . ? N4 C5 1.473(7) . ? C2 C3 1.347(10) . ? C4 C5 1.525(9) . ? C6 C7 1.356(9) . ? C9 C12 1.523(9) . ? C9 C11 1.522(9) . ? C9 C10 1.533(9) . ? C13 C16 1.514(8) . ? C13 C15 1.520(9) . ? C13 C14 1.539(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 In1 C1 112.5(2) . . ? C8 In1 Br2 123.68(15) . . ? C1 In1 Br2 123.86(15) . . ? C8 In1 Br1 92.98(15) . . ? C1 In1 Br1 85.46(15) . . ? Br2 In1 Br1 91.04(2) . . ? C8 In1 Br3 84.71(15) . . ? C1 In1 Br3 92.97(15) . . ? Br2 In1 Br3 92.44(2) . . ? Br1 In1 Br3 176.50(2) . . ? C1 N1 C2 109.7(5) . . ? C1 N1 C9 126.1(5) . . ? C2 N1 C9 124.1(5) . . ? C1 N2 C3 111.4(5) . . ? C1 N2 C4 124.5(5) . . ? C3 N2 C4 124.0(5) . . ? C8 N3 C7 109.8(5) . . ? C8 N3 C13 126.8(5) . . ? C7 N3 C13 123.3(5) . . ? C8 N4 C6 110.9(5) . . ? C8 N4 C5 125.7(5) . . ? C6 N4 C5 123.4(5) . . ? N2 C1 N1 105.2(5) . . ? N2 C1 In1 118.8(4) . . ? N1 C1 In1 135.9(4) . . ? C3 C2 N1 107.2(5) . . ? C2 C3 N2 106.4(6) . . ? N2 C4 C5 112.7(5) . . ? N4 C5 C4 112.8(5) . . ? C7 C6 N4 106.0(5) . . ? C6 C7 N3 107.4(5) . . ? N3 C8 N4 105.8(5) . . ? N3 C8 In1 136.4(4) . . ? N4 C8 In1 117.5(4) . . ? N1 C9 C12 109.2(5) . . ? N1 C9 C11 107.6(5) . . ? C12 C9 C11 110.0(6) . . ? N1 C9 C10 108.2(5) . . ? C12 C9 C10 109.3(5) . . ? C11 C9 C10 112.4(6) . . ? N3 C13 C16 109.9(5) . . ? N3 C13 C15 108.2(5) . . ? C16 C13 C15 110.5(5) . . ? N3 C13 C14 106.7(5) . . ? C16 C13 C14 110.1(5) . . ? C15 C13 C14 111.4(5) . . ? Cl2 C17 Cl1 112.6(5) . . ? Cl3 C18 Cl4 112.7(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.207 _refine_diff_density_min -1.175 _refine_diff_density_rms 0.154 data_compound7 _database_code_CSD 177620 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 In2 N4' _chemical_formula_weight 510.10 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' 'In' 'In' -0.7276 1.3100 '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 5.61100(10) _cell_length_b 8.2530(2) _cell_length_c 11.6770(3) _cell_angle_alpha 85.4570(10) _cell_angle_beta 85.4100(10) _cell_angle_gamma 76.2580(10) _cell_volume 522.56(2) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 254 _exptl_absorpt_coefficient_mu 2.209 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.80 _exptl_absorpt_process_details 'Sortav Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13602 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 34.94 _reflns_number_total 4544 _reflns_number_gt 3831 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+0.0675P] 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 SHELXL _refine_ls_extinction_coef 0.045(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4544 _refine_ls_number_parameters 116 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0689 _refine_ls_wR_factor_gt 0.0647 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group In1 In 0.28009(2) 0.801048(13) 0.266550(10) 0.02580(6) Uani 1 1 d D . . H1 H 0.022(5) 0.720(4) 0.281(3) 0.082(11) Uiso 1 1 d D . . H2 H 0.505(5) 0.698(3) 0.356(2) 0.059(9) Uiso 1 1 d D . . H3 H 0.402(5) 0.822(4) 0.1269(19) 0.057(8) Uiso 1 1 d D . . N1 N 0.2186(3) 1.11369(18) 0.42609(12) 0.0214(3) Uani 1 1 d . . . N2 N 0.0201(3) 1.21492(18) 0.27665(12) 0.0216(3) Uani 1 1 d . . . C1 C 0.1523(3) 1.0697(2) 0.32598(14) 0.0195(3) Uani 1 1 d . . . C2 C 0.1354(4) 1.2826(2) 0.43851(19) 0.0368(5) Uani 1 1 d . . . H2A H 0.1605 1.3426 0.5009 0.044 Uiso 1 1 calc R . . C3 C 0.0116(4) 1.3462(2) 0.34482(18) 0.0357(5) Uani 1 1 d . . . H3A H -0.0671 1.4600 0.3285 0.043 Uiso 1 1 calc R . . C4 C 0.3636(3) 1.0028(2) 0.51224(14) 0.0223(3) Uani 1 1 d . . . H4A H 0.3362 0.8889 0.5110 0.027 Uiso 1 1 calc R . . H4B H 0.3098 1.0434 0.5898 0.027 Uiso 1 1 calc R . . C5 C -0.0922(3) 1.2375(2) 0.16216(14) 0.0223(3) Uani 1 1 d . . . C6 C 0.1126(4) 1.2297(3) 0.06806(17) 0.0385(5) Uani 1 1 d . . . H6A H 0.2307 1.1215 0.0755 0.058 Uiso 1 1 calc R . . H6B H 0.1963 1.3197 0.0753 0.058 Uiso 1 1 calc R . . H6C H 0.0430 1.2431 -0.0074 0.058 Uiso 1 1 calc R . . C7 C -0.2744(5) 1.4063(3) 0.1529(2) 0.0408(5) Uani 1 1 d . . . H7A H -0.3508 1.4200 0.0791 0.061 Uiso 1 1 calc R . . H7B H -0.1880 1.4955 0.1577 0.061 Uiso 1 1 calc R . . H7C H -0.4018 1.4122 0.2160 0.061 Uiso 1 1 calc R . . C8 C -0.2310(4) 1.1019(3) 0.15271(18) 0.0345(4) Uani 1 1 d . . . H8A H -0.3596 1.1085 0.2153 0.052 Uiso 1 1 calc R . . H8B H -0.1165 0.9920 0.1583 0.052 Uiso 1 1 calc R . . H8C H -0.3062 1.1179 0.0785 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 In1 0.03104(9) 0.01843(8) 0.02740(8) -0.00353(5) -0.00746(5) -0.00220(5) N1 0.0235(7) 0.0196(7) 0.0202(6) -0.0017(5) -0.0062(5) -0.0019(5) N2 0.0256(7) 0.0180(6) 0.0205(6) -0.0022(5) -0.0049(5) -0.0024(5) C1 0.0195(7) 0.0199(7) 0.0189(7) -0.0004(5) -0.0022(5) -0.0043(5) C2 0.0533(13) 0.0226(9) 0.0328(10) -0.0107(7) -0.0182(9) 0.0025(8) C3 0.0511(13) 0.0185(9) 0.0351(10) -0.0069(7) -0.0174(9) 0.0033(8) C4 0.0243(8) 0.0239(8) 0.0184(7) 0.0013(6) -0.0051(6) -0.0044(6) C5 0.0231(8) 0.0228(8) 0.0207(7) 0.0003(6) -0.0068(6) -0.0033(6) C6 0.0315(11) 0.0592(14) 0.0248(9) 0.0036(9) -0.0018(8) -0.0125(9) C7 0.0472(13) 0.0305(11) 0.0396(11) -0.0020(8) -0.0198(10) 0.0067(9) C8 0.0414(11) 0.0328(10) 0.0341(10) 0.0052(8) -0.0183(9) -0.0150(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 In1 C1 2.3069(16) . ? N1 C1 1.355(2) . ? N1 C2 1.376(2) . ? N1 C4 1.464(2) . ? N2 C1 1.362(2) . ? N2 C3 1.384(2) . ? N2 C5 1.503(2) . ? C2 C3 1.346(3) . ? C4 C4 1.524(3) 2_676 ? C5 C6 1.519(3) . ? C5 C7 1.521(3) . ? C5 C8 1.523(3) . ? 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 C1 N1 C2 111.34(14) . . ? C1 N1 C4 126.72(14) . . ? C2 N1 C4 121.93(15) . . ? C1 N2 C3 110.22(15) . . ? C1 N2 C5 126.65(14) . . ? C3 N2 C5 123.05(14) . . ? N1 C1 N2 104.58(14) . . ? N1 C1 In1 122.11(11) . . ? N2 C1 In1 133.21(12) . . ? C3 C2 N1 106.49(17) . . ? C2 C3 N2 107.35(17) . . ? N1 C4 C4 110.47(16) . 2_676 ? N2 C5 C6 108.28(15) . . ? N2 C5 C7 109.43(15) . . ? C6 C5 C7 110.00(17) . . ? N2 C5 C8 109.61(14) . . ? C6 C5 C8 111.28(17) . . ? C7 C5 C8 108.22(17) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 34.94 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.927 _refine_diff_density_min -0.885 _refine_diff_density_rms 0.113 data_cmpd5 _database_code_CSD 177621 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 Al2 N4' _chemical_formula_weight 334.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Al' 'Al' 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0020(2) _cell_length_b 25.0350(8) _cell_length_c 6.8670(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.031(2) _cell_angle_gamma 90.00 _cell_volume 1016.06(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Irregular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.093 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9714 _exptl_absorpt_correction_T_max 0.9785 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13427 _diffrn_reflns_av_R_equivalents 0.0871 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.90 _reflns_number_total 2391 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc [1.00000+0.00000exp(0.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+0.0000+0.6752*P+(0.0555P)^2^+0.0000sin\q/\l] where P = 0.00000Fo^2^ + 1.00000Fc^2^ ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.047(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2391 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0815 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1431 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 1.32959(12) 0.11482(3) 0.46458(10) 0.0298(3) Uani 1 1 d . . . N1 N 0.9814(3) 0.03767(7) 0.2638(3) 0.0252(4) Uani 1 1 d . . . N2 N 0.9227(3) 0.11092(7) 0.1009(3) 0.0241(4) Uani 1 1 d . . . C1 C 1.0569(4) 0.08889(8) 0.2600(3) 0.0240(5) Uani 1 1 d . . . C2 C 1.0671(4) -0.00179(9) 0.4157(3) 0.0282(5) Uani 1 1 d . . . C3 C 0.8048(4) 0.02811(9) 0.1113(3) 0.0285(5) Uani 1 1 d . . . C4 C 0.7666(4) 0.07412(9) 0.0098(3) 0.0280(5) Uani 1 1 d . . . C5 C 0.9324(4) 0.16854(9) 0.0389(3) 0.0278(5) Uani 1 1 d . . . C6 C 0.7747(5) 0.17639(12) -0.1580(4) 0.0395(7) Uani 1 1 d . . . C7 C 0.8535(5) 0.20304(10) 0.1971(4) 0.0346(6) Uani 1 1 d . . . C8 C 1.1718(5) 0.18190(11) 0.0144(4) 0.0350(6) Uani 1 1 d . . . H1 H 1.294(5) 0.0909(13) 0.660(5) 0.065(9) Uiso 1 1 d . . . H2 H 1.543(6) 0.0943(13) 0.400(5) 0.066(9) Uiso 1 1 d . . . H3 H 1.340(5) 0.1733(12) 0.478(4) 0.058(9) Uiso 1 1 d . . . H4 H 1.221(5) 0.0053(10) 0.460(4) 0.032(7) Uiso 1 1 d . . . H5 H 1.047(4) -0.0387(11) 0.360(4) 0.036(7) Uiso 1 1 d . . . H6 H 0.732(4) -0.0060(10) 0.095(4) 0.031(6) Uiso 1 1 d . . . H7 H 0.664(4) 0.0819(10) -0.102(4) 0.033(7) Uiso 1 1 d . . . H8 H 0.814(4) 0.1571(11) -0.256(4) 0.030(7) Uiso 1 1 d . . . H9 H 0.793(5) 0.2086(13) -0.196(4) 0.049(8) Uiso 1 1 d . . . H10 H 0.607(5) 0.1708(10) -0.147(4) 0.040(7) Uiso 1 1 d . . . H11 H 0.709(5) 0.1950(11) 0.206(4) 0.041(8) Uiso 1 1 d . . . H12 H 0.853(4) 0.2394(11) 0.156(3) 0.031(6) Uiso 1 1 d . . . H13 H 0.963(5) 0.1995(11) 0.331(4) 0.043(7) Uiso 1 1 d . . . H14 H 1.174(5) 0.2174(13) -0.034(4) 0.053(8) Uiso 1 1 d . . . H15 H 1.218(5) 0.1593(12) -0.081(4) 0.048(8) Uiso 1 1 d . . . H16 H 1.276(4) 0.1783(9) 0.134(4) 0.026(6) Uiso 1 1 d . . . 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 0.0335(4) 0.0258(4) 0.0267(4) -0.0001(3) -0.0043(3) -0.0002(3) N1 0.0324(11) 0.0200(9) 0.0225(9) 0.0008(7) 0.0027(7) 0.0012(8) N2 0.0272(10) 0.0208(9) 0.0232(9) 0.0018(7) 0.0014(7) -0.0006(7) C1 0.0281(12) 0.0211(11) 0.0223(11) -0.0016(8) 0.0030(8) 0.0015(9) C2 0.0370(14) 0.0210(11) 0.0249(11) 0.0017(8) 0.0010(9) 0.0045(10) C3 0.0326(13) 0.0251(12) 0.0261(12) -0.0013(9) 0.0007(9) -0.0027(10) C4 0.0319(13) 0.0272(12) 0.0229(11) -0.0012(8) -0.0009(9) -0.0003(9) C5 0.0338(13) 0.0202(11) 0.0276(11) 0.0047(8) 0.0007(9) -0.0001(9) C6 0.0476(18) 0.0310(14) 0.0348(15) 0.0119(11) -0.0073(12) -0.0029(12) C7 0.0377(15) 0.0233(13) 0.0430(15) 0.0010(10) 0.0077(12) 0.0033(11) C8 0.0364(14) 0.0342(14) 0.0343(14) 0.0042(11) 0.0059(11) -0.0044(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Al1 C1 2.067(2) . ? N1 C1 1.362(3) . ? N1 C3 1.375(3) . ? N1 C2 1.463(3) . ? N2 C1 1.357(3) . ? N2 C4 1.383(3) . ? N2 C5 1.508(3) . ? C2 C2 1.524(5) 3_756 ? C3 C4 1.345(3) . ? C5 C8 1.513(3) . ? C5 C6 1.523(3) . ? C5 C7 1.526(3) . ? 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 C1 N1 C3 111.35(18) . . ? C1 N1 C2 124.93(19) . . ? C3 N1 C2 123.63(19) . . ? C1 N2 C4 110.71(17) . . ? C1 N2 C5 124.71(17) . . ? C4 N2 C5 124.48(17) . . ? N2 C1 N1 104.21(18) . . ? N2 C1 Al1 135.11(16) . . ? N1 C1 Al1 120.62(15) . . ? N1 C2 C2 109.6(2) . 3_756 ? C4 C3 N1 106.5(2) . . ? C3 C4 N2 107.2(2) . . ? N2 C5 C8 109.08(19) . . ? N2 C5 C6 108.99(19) . . ? C8 C5 C6 109.2(2) . . ? N2 C5 C7 107.99(18) . . ? C8 C5 C7 111.9(2) . . ? C6 C5 C7 109.7(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.314 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.054