# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Munoz-Hernandez, Miguel-Angel' _publ_contact_author_name 'Munoz-Hernandez, Miguel-Angel' _publ_contact_author_email mamund2@buzon.uaem.mx _publ_section_title ; Steric control of conformation in self-assembly metallacalix[4]arenes derived from AlMe3 or GaMe3 with benzimidazolyl ligands ; # Attachment '- complexes cif.cif' data_complex_1 _database_code_depnum_ccdc_archive 'CCDC 803985' #TrackingRef '- complexes cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 Al4 N8' _chemical_formula_weight 696.71 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 P2(1)/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 10.108(3) _cell_length_b 11.423(3) _cell_length_c 17.530(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.999(4) _cell_angle_gamma 90.00 _cell_volume 1999.1(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(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 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9674 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4628 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_sigmaI/netI 0.1019 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3071 _reflns_number_gt 2023 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.1016P)^2^+0.1288P] 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 3071 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.2014 _refine_ls_wR_factor_gt 0.1676 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.304 _refine_ls_shift/su_mean 0.005 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 0.18279(11) 0.78817(12) 0.04194(7) 0.0214(4) Uani 1 1 d . . . Al2 Al 0.64781(12) 1.00247(13) 0.23165(7) 0.0255(4) Uani 1 1 d . . . N3 N 0.1753(3) 0.8413(3) -0.0627(2) 0.0233(9) Uani 1 1 d . . . N1 N 0.3677(3) 0.8239(3) 0.07859(19) 0.0223(9) Uani 1 1 d . . . N2 N 0.5481(3) 0.9045(3) 0.1535(2) 0.0253(10) Uani 1 1 d . . . N4 N 0.7665(3) 1.0742(3) 0.1692(2) 0.0256(9) Uani 1 1 d . . . C1 C 0.4140(4) 0.8991(4) 0.1336(2) 0.0238(11) Uani 1 1 d . . . H1 H 0.3558 0.9468 0.1578 0.029 Uiso 1 1 calc R . . C2 C 0.4834(4) 0.7690(4) 0.0602(2) 0.0178(10) Uani 1 1 d . . . C3 C 0.5937(4) 0.8164(4) 0.1073(2) 0.0221(11) Uani 1 1 d . . . C16 C 0.0761(4) 0.8881(5) 0.0965(3) 0.0381(13) Uani 1 1 d . . . H16A H 0.1104 0.9684 0.0968 0.057 Uiso 1 1 calc R . . H16B H 0.0809 0.8603 0.1497 0.057 Uiso 1 1 calc R . . H16C H -0.0171 0.8865 0.0707 0.057 Uiso 1 1 calc R . . C4 C 0.7232(4) 0.7809(5) 0.1021(3) 0.0319(12) Uani 1 1 d . . . H4 H 0.7991 0.8143 0.1334 0.038 Uiso 1 1 calc R . . C18 C 0.7528(5) 0.9119(5) 0.3132(3) 0.0403(14) Uani 1 1 d . . . H18A H 0.6941 0.8575 0.3353 0.060 Uiso 1 1 calc R . . H18B H 0.7958 0.9649 0.3537 0.060 Uiso 1 1 calc R . . H18C H 0.8217 0.8677 0.2919 0.060 Uiso 1 1 calc R . . C6 C 0.6246(4) 0.6459(5) 0.0023(3) 0.0378(13) Uani 1 1 d . . . H6 H 0.6388 0.5869 -0.0337 0.045 Uiso 1 1 calc R . . C5 C 0.7354(4) 0.6949(5) 0.0493(3) 0.0359(13) Uani 1 1 d . . . H5 H 0.8223 0.6674 0.0444 0.043 Uiso 1 1 calc R . . C15 C 0.1515(4) 0.6202(4) 0.0389(3) 0.0335(13) Uani 1 1 d . . . H15A H 0.1161 0.5964 -0.0140 0.050 Uiso 1 1 calc R . . H15B H 0.0867 0.6004 0.0730 0.050 Uiso 1 1 calc R . . H15C H 0.2360 0.5792 0.0563 0.050 Uiso 1 1 calc R . . C7 C 0.4958(4) 0.6806(4) 0.0067(3) 0.0291(12) Uani 1 1 d . . . H7 H 0.4202 0.6468 -0.0246 0.035 Uiso 1 1 calc R . . C17 C 0.5162(5) 1.1186(5) 0.2545(3) 0.0433(14) Uani 1 1 d . . . H17A H 0.4759 1.1572 0.2065 0.065 Uiso 1 1 calc R . . H17B H 0.5610 1.1772 0.2904 0.065 Uiso 1 1 calc R . . H17C H 0.4462 1.0794 0.2779 0.065 Uiso 1 1 calc R . . C14 C 0.7322(4) 1.1037(4) 0.0952(2) 0.0223(11) Uani 1 1 d . . . H14 H 0.6462 1.0862 0.0673 0.027 Uiso 1 1 calc R . . C11 C 0.0663(4) 0.8324(4) -0.1225(2) 0.0241(11) Uani 1 1 d . . . C10 C -0.0580(4) 0.7812(5) -0.1223(3) 0.0352(13) Uani 1 1 d . . . H10 H -0.0802 0.7428 -0.0780 0.042 Uiso 1 1 calc R . . C13 C 0.8988(4) 1.1153(4) 0.1877(2) 0.0228(11) Uani 1 1 d . . . C9 C -0.1474(4) 0.7890(5) -0.1898(3) 0.0380(14) Uani 1 1 d . . . H9 H -0.2342 0.7561 -0.1919 0.046 Uiso 1 1 calc R . . C12 C 0.9887(4) 1.1076(4) 0.2565(3) 0.0320(12) Uani 1 1 d . . . H12 H 0.9654 1.0714 0.3013 0.038 Uiso 1 1 calc R . . C8 C -0.1141(4) 0.8438(5) -0.2554(3) 0.0367(13) Uani 1 1 d . . . H8 H -0.1794 0.8479 -0.3007 0.044 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 0.0180(6) 0.0190(10) 0.0265(7) -0.0015(6) 0.0008(5) -0.0013(6) Al2 0.0234(7) 0.0275(11) 0.0238(7) -0.0012(7) -0.0016(5) -0.0058(6) N3 0.0166(17) 0.027(3) 0.025(2) -0.0028(18) -0.0006(14) -0.0025(16) N1 0.0200(18) 0.023(3) 0.0229(19) -0.0044(17) -0.0004(14) 0.0026(16) N2 0.0181(17) 0.031(3) 0.026(2) -0.0003(18) -0.0016(14) 0.0005(16) N4 0.0179(17) 0.033(3) 0.023(2) -0.0025(18) -0.0037(14) -0.0048(17) C1 0.026(2) 0.018(3) 0.027(2) 0.003(2) 0.0033(18) 0.001(2) C2 0.019(2) 0.004(3) 0.030(2) 0.001(2) 0.0011(17) 0.0024(17) C3 0.021(2) 0.017(3) 0.026(2) 0.003(2) -0.0017(17) 0.0002(19) C16 0.023(2) 0.043(4) 0.049(3) -0.006(3) 0.007(2) -0.003(2) C4 0.022(2) 0.037(4) 0.036(3) 0.005(3) 0.0009(19) -0.001(2) C18 0.049(3) 0.030(4) 0.038(3) 0.010(3) -0.006(2) -0.015(3) C6 0.033(3) 0.040(4) 0.040(3) -0.008(3) 0.005(2) 0.004(2) C5 0.023(2) 0.032(4) 0.052(3) 0.006(3) 0.005(2) 0.006(2) C15 0.026(2) 0.034(4) 0.040(3) -0.007(3) 0.002(2) -0.002(2) C7 0.030(2) 0.021(3) 0.035(3) -0.006(2) 0.001(2) 0.003(2) C17 0.040(3) 0.036(4) 0.054(3) -0.021(3) 0.008(2) -0.011(3) C14 0.019(2) 0.021(3) 0.024(2) 0.001(2) -0.0036(17) 0.0001(19) C11 0.0136(19) 0.032(3) 0.025(2) -0.010(2) -0.0042(17) 0.0032(19) C10 0.024(2) 0.048(4) 0.032(3) -0.003(3) 0.000(2) -0.009(2) C13 0.021(2) 0.022(3) 0.024(2) -0.006(2) 0.0009(17) -0.0009(19) C9 0.022(2) 0.049(4) 0.041(3) -0.007(3) -0.001(2) -0.004(2) C12 0.027(2) 0.040(4) 0.027(3) -0.007(2) -0.0020(19) 0.002(2) C8 0.027(2) 0.043(4) 0.036(3) -0.012(3) -0.008(2) 0.001(2) _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 N3 1.922(4) . ? Al1 C16 1.924(5) . ? Al1 N1 1.923(3) . ? Al1 C15 1.943(5) . ? Al2 N2 1.927(4) . ? Al2 N4 1.929(4) . ? Al2 C18 1.941(5) . ? Al2 C17 1.963(5) . ? N3 C14 1.327(5) 3_675 ? N3 C11 1.401(5) . ? N1 C1 1.320(5) . ? N1 C2 1.408(5) . ? N2 C1 1.347(5) . ? N2 C3 1.412(6) . ? N4 C14 1.331(5) . ? N4 C13 1.406(5) . ? C1 H1 0.9500 . ? C2 C3 1.390(5) . ? C2 C7 1.396(6) . ? C3 C4 1.388(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C4 C5 1.367(7) . ? C4 H4 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C6 C7 1.374(6) . ? C6 C5 1.399(7) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C7 H7 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C14 N3 1.327(5) 3_675 ? C14 H14 0.9500 . ? C11 C13 1.384(6) 3_675 ? C11 C10 1.386(6) . ? C10 C9 1.374(6) . ? C10 H10 0.9500 . ? C13 C11 1.384(6) 3_675 ? C13 C12 1.394(6) . ? C9 C8 1.395(7) . ? C9 H9 0.9500 . ? C12 C8 1.387(6) 3_675 ? C12 H12 0.9500 . ? C8 C12 1.387(6) 3_675 ? C8 H8 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 N3 Al1 C16 110.2(2) . . ? N3 Al1 N1 98.20(15) . . ? C16 Al1 N1 107.40(18) . . ? N3 Al1 C15 107.71(19) . . ? C16 Al1 C15 119.8(2) . . ? N1 Al1 C15 111.35(18) . . ? N2 Al2 N4 98.39(16) . . ? N2 Al2 C18 112.3(2) . . ? N4 Al2 C18 109.13(19) . . ? N2 Al2 C17 104.00(19) . . ? N4 Al2 C17 109.3(2) . . ? C18 Al2 C17 121.3(2) . . ? C14 N3 C11 103.7(3) 3_675 . ? C14 N3 Al1 129.4(3) 3_675 . ? C11 N3 Al1 126.8(3) . . ? C1 N1 C2 104.2(3) . . ? C1 N1 Al1 126.6(3) . . ? C2 N1 Al1 128.9(3) . . ? C1 N2 C3 102.9(3) . . ? C1 N2 Al2 127.2(3) . . ? C3 N2 Al2 129.8(3) . . ? C14 N4 C13 103.5(3) . . ? C14 N4 Al2 124.7(3) . . ? C13 N4 Al2 131.6(3) . . ? N1 C1 N2 116.5(4) . . ? N1 C1 H1 121.8 . . ? N2 C1 H1 121.8 . . ? C3 C2 C7 122.2(4) . . ? C3 C2 N1 107.9(4) . . ? C7 C2 N1 129.9(4) . . ? C4 C3 C2 121.6(4) . . ? C4 C3 N2 129.9(4) . . ? C2 C3 N2 108.4(4) . . ? Al1 C16 H16A 109.5 . . ? Al1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Al1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C5 C4 C3 116.1(4) . . ? C5 C4 H4 121.9 . . ? C3 C4 H4 121.9 . . ? Al2 C18 H18A 109.5 . . ? Al2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Al2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C7 C6 C5 122.0(5) . . ? C7 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? C4 C5 C6 122.5(4) . . ? C4 C5 H5 118.8 . . ? C6 C5 H5 118.8 . . ? Al1 C15 H15A 109.5 . . ? Al1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Al1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C6 C7 C2 115.5(4) . . ? C6 C7 H7 122.2 . . ? C2 C7 H7 122.2 . . ? Al2 C17 H17A 109.5 . . ? Al2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Al2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N3 C14 N4 116.4(3) 3_675 . ? N3 C14 H14 121.8 3_675 . ? N4 C14 H14 121.8 . . ? C13 C11 C10 122.2(4) 3_675 . ? C13 C11 N3 108.3(4) 3_675 . ? C10 C11 N3 129.5(4) . . ? C9 C10 C11 116.4(5) . . ? C9 C10 H10 121.8 . . ? C11 C10 H10 121.8 . . ? C11 C13 C12 121.7(4) 3_675 . ? C11 C13 N4 108.0(4) 3_675 . ? C12 C13 N4 130.3(4) . . ? C10 C9 C8 121.8(4) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C8 C12 C13 115.9(4) 3_675 . ? C8 C12 H12 122.0 3_675 . ? C13 C12 H12 122.0 . . ? C12 C8 C9 121.9(4) 3_675 . ? C12 C8 H8 119.0 3_675 . ? C9 C8 H8 119.0 . . ? 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 C16 Al1 N3 C14 106.1(4) . . . 3_675 ? N1 Al1 N3 C14 -5.9(4) . . . 3_675 ? C15 Al1 N3 C14 -121.6(4) . . . 3_675 ? C16 Al1 N3 C11 -72.3(4) . . . . ? N1 Al1 N3 C11 175.7(4) . . . . ? C15 Al1 N3 C11 60.1(4) . . . . ? N3 Al1 N1 C1 117.1(4) . . . . ? C16 Al1 N1 C1 2.9(4) . . . . ? C15 Al1 N1 C1 -130.1(4) . . . . ? N3 Al1 N1 C2 -70.5(4) . . . . ? C16 Al1 N1 C2 175.3(4) . . . . ? C15 Al1 N1 C2 42.2(4) . . . . ? N4 Al2 N2 C1 -126.9(4) . . . . ? C18 Al2 N2 C1 118.3(4) . . . . ? C17 Al2 N2 C1 -14.6(4) . . . . ? N4 Al2 N2 C3 57.9(4) . . . . ? C18 Al2 N2 C3 -56.8(4) . . . . ? C17 Al2 N2 C3 170.3(4) . . . . ? N2 Al2 N4 C14 36.2(4) . . . . ? C18 Al2 N4 C14 153.4(4) . . . . ? C17 Al2 N4 C14 -71.9(4) . . . . ? N2 Al2 N4 C13 -148.9(4) . . . . ? C18 Al2 N4 C13 -31.7(5) . . . . ? C17 Al2 N4 C13 103.0(4) . . . . ? C2 N1 C1 N2 1.8(5) . . . . ? Al1 N1 C1 N2 175.7(3) . . . . ? C3 N2 C1 N1 -3.1(5) . . . . ? Al2 N2 C1 N1 -179.2(3) . . . . ? C1 N1 C2 C3 0.4(5) . . . . ? Al1 N1 C2 C3 -173.3(3) . . . . ? C1 N1 C2 C7 179.0(5) . . . . ? Al1 N1 C2 C7 5.4(7) . . . . ? C7 C2 C3 C4 2.0(7) . . . . ? N1 C2 C3 C4 -179.1(4) . . . . ? C7 C2 C3 N2 179.0(4) . . . . ? N1 C2 C3 N2 -2.2(5) . . . . ? C1 N2 C3 C4 179.7(5) . . . . ? Al2 N2 C3 C4 -4.3(7) . . . . ? C1 N2 C3 C2 3.1(5) . . . . ? Al2 N2 C3 C2 179.1(3) . . . . ? C2 C3 C4 C5 -1.5(7) . . . . ? N2 C3 C4 C5 -177.7(5) . . . . ? C3 C4 C5 C6 0.7(7) . . . . ? C7 C6 C5 C4 -0.5(8) . . . . ? C5 C6 C7 C2 1.0(7) . . . . ? C3 C2 C7 C6 -1.7(7) . . . . ? N1 C2 C7 C6 179.8(4) . . . . ? C13 N4 C14 N3 0.0(5) . . . 3_675 ? Al2 N4 C14 N3 176.1(3) . . . 3_675 ? C14 N3 C11 C13 -0.6(5) 3_675 . . 3_675 ? Al1 N3 C11 C13 178.1(3) . . . 3_675 ? C14 N3 C11 C10 178.9(5) 3_675 . . . ? Al1 N3 C11 C10 -2.4(7) . . . . ? C13 C11 C10 C9 -2.4(7) 3_675 . . . ? N3 C11 C10 C9 178.1(5) . . . . ? C14 N4 C13 C11 0.4(5) . . . 3_675 ? Al2 N4 C13 C11 -175.3(3) . . . 3_675 ? C14 N4 C13 C12 -178.4(5) . . . . ? Al2 N4 C13 C12 6.0(8) . . . . ? C11 C10 C9 C8 1.0(8) . . . . ? C11 C13 C12 C8 0.4(7) 3_675 . . 3_675 ? N4 C13 C12 C8 179.0(5) . . . 3_675 ? C10 C9 C8 C12 0.7(8) . . . 3_675 ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.874 _refine_diff_density_max 0.565 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.082 #===END data_complex_2 _database_code_depnum_ccdc_archive 'CCDC 803986' #TrackingRef '- complexes cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H44 Ga4 N8' _chemical_formula_weight 867.67 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' 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 P2(1)/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 10.101(3) _cell_length_b 11.384(4) _cell_length_c 17.487(6) _cell_angle_alpha 90.00 _cell_angle_beta 98.261(10) _cell_angle_gamma 90.00 _cell_volume 1989.8(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 1.448 _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 2.714 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5066 _exptl_absorpt_correction_T_max 0.6408 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7122 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0805 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3389 _reflns_number_gt 2495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0300P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3389 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0699 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.0951 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.132 _refine_ls_shift/su_mean 0.002 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 Ga1 Ga 0.67641(5) 0.71439(5) 0.04652(3) 0.01624(16) Uani 1 1 d . . . Ga2 Ga 1.14639(5) 0.49223(5) 0.23661(3) 0.01904(16) Uani 1 1 d . . . N1 N 0.8669(4) 0.6748(3) 0.0816(2) 0.0184(9) Uani 1 1 d . . . N3 N 0.6724(4) 0.6608(3) -0.0620(2) 0.0140(9) Uani 1 1 d . . . N2 N 1.0449(4) 0.5951(3) 0.1552(2) 0.0167(9) Uani 1 1 d . . . N4 N 1.2683(3) 0.4210(3) 0.1694(2) 0.0154(9) Uani 1 1 d . . . C10 C 0.4393(5) 0.7207(4) -0.1197(3) 0.0233(12) Uani 1 1 d . . . H10 H 0.4159 0.7572 -0.0747 0.028 Uiso 1 1 calc R . . C11 C 0.3503(5) 0.7153(5) -0.1874(3) 0.0247(12) Uani 1 1 d . . . H11 H 0.2638 0.7489 -0.1891 0.030 Uiso 1 1 calc R . . C9 C 0.5648(5) 0.6703(4) -0.1203(3) 0.0176(11) Uani 1 1 d . . . C1 C 0.9130(5) 0.5966(4) 0.1357(3) 0.0188(11) Uani 1 1 d . . . H1 H 0.8555 0.5457 0.1587 0.023 Uiso 1 1 calc R . . C16 C 0.6518(5) 0.8852(4) 0.0426(3) 0.0213(12) Uani 1 1 d . . . H16A H 0.5601 0.9043 0.0504 0.032 Uiso 1 1 calc R . . H16B H 0.6680 0.9146 -0.0079 0.032 Uiso 1 1 calc R . . H16C H 0.7149 0.9220 0.0834 0.032 Uiso 1 1 calc R . . C8 C 0.7656(4) 0.6063(4) -0.0947(3) 0.0165(11) Uani 1 1 d . . . H8 H 0.8509 0.5877 -0.0669 0.020 Uiso 1 1 calc R . . C4 C 1.2201(5) 0.7185(4) 0.1038(3) 0.0213(12) Uani 1 1 d . . . H4 H 1.2955 0.6846 0.1347 0.026 Uiso 1 1 calc R . . C3 C 1.0925(5) 0.6810(4) 0.1094(3) 0.0178(11) Uani 1 1 d . . . C18 C 1.2533(5) 0.5866(5) 0.3154(3) 0.0320(14) Uani 1 1 d . . . H18A H 1.1954 0.6430 0.3371 0.048 Uiso 1 1 calc R . . H18B H 1.3220 0.6291 0.2923 0.048 Uiso 1 1 calc R . . H18C H 1.2963 0.5352 0.3566 0.048 Uiso 1 1 calc R . . C2 C 0.9824(5) 0.7300(4) 0.0637(3) 0.0184(11) Uani 1 1 d . . . C6 C 1.1251(5) 0.8543(4) 0.0058(3) 0.0246(12) Uani 1 1 d . . . H6 H 1.1392 0.9144 -0.0299 0.030 Uiso 1 1 calc R . . C15 C 0.5704(5) 0.6057(4) 0.0985(3) 0.0274(13) Uani 1 1 d . . . H15A H 0.5628 0.6354 0.1503 0.041 Uiso 1 1 calc R . . H15B H 0.6140 0.5286 0.1027 0.041 Uiso 1 1 calc R . . H15C H 0.4809 0.5983 0.0687 0.041 Uiso 1 1 calc R . . C5 C 1.2352(5) 0.8065(5) 0.0521(3) 0.0288(13) Uani 1 1 d . . . H5 H 1.3222 0.8352 0.0479 0.035 Uiso 1 1 calc R . . C7 C 0.9969(5) 0.8180(4) 0.0098(3) 0.0204(12) Uani 1 1 d . . . H7 H 0.9221 0.8508 -0.0223 0.024 Uiso 1 1 calc R . . C12 C 0.3849(5) 0.6618(4) -0.2527(3) 0.0283(13) Uani 1 1 d . . . H12 H 0.3200 0.6576 -0.2977 0.034 Uiso 1 1 calc R . . C13 C 0.5091(5) 0.6144(4) -0.2552(3) 0.0234(12) Uani 1 1 d . . . H13 H 0.5323 0.5802 -0.3010 0.028 Uiso 1 1 calc R . . C14 C 1.4008(4) 0.3812(4) 0.1873(3) 0.0155(11) Uani 1 1 d . . . C17 C 1.0140(5) 0.3743(5) 0.2549(3) 0.0301(14) Uani 1 1 d . . . H17A H 1.0551 0.3172 0.2930 0.045 Uiso 1 1 calc R . . H17B H 0.9815 0.3338 0.2063 0.045 Uiso 1 1 calc R . . H17C H 0.9387 0.4127 0.2744 0.045 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 Ga1 0.0162(3) 0.0189(3) 0.0133(3) 0.0013(2) 0.0009(2) 0.0007(2) Ga2 0.0198(3) 0.0237(3) 0.0129(3) 0.0008(2) -0.0001(2) 0.0040(2) N1 0.018(2) 0.019(2) 0.018(2) 0.0008(19) 0.0034(18) -0.0010(18) N3 0.014(2) 0.017(2) 0.008(2) 0.0015(17) -0.0053(17) 0.0002(17) N2 0.014(2) 0.025(2) 0.009(2) 0.0024(18) -0.0047(17) 0.0036(18) N4 0.015(2) 0.021(2) 0.009(2) 0.0018(18) -0.0062(17) 0.0003(18) C10 0.022(3) 0.025(3) 0.024(3) -0.002(2) 0.007(2) 0.000(2) C11 0.013(3) 0.032(3) 0.027(3) -0.001(3) -0.004(2) 0.004(2) C9 0.016(3) 0.019(3) 0.016(3) 0.001(2) -0.004(2) -0.005(2) C1 0.022(3) 0.018(3) 0.016(3) 0.003(2) 0.001(2) 0.000(2) C16 0.021(3) 0.027(3) 0.015(3) 0.002(2) 0.000(2) 0.003(2) C8 0.011(2) 0.023(3) 0.013(3) 0.001(2) -0.006(2) 0.004(2) C4 0.017(3) 0.025(3) 0.020(3) -0.005(2) -0.006(2) 0.002(2) C3 0.018(3) 0.018(3) 0.017(3) -0.001(2) 0.000(2) -0.001(2) C18 0.036(3) 0.030(3) 0.026(3) -0.005(3) -0.006(3) 0.012(3) C2 0.019(3) 0.018(3) 0.018(3) -0.003(2) 0.002(2) 0.000(2) C6 0.028(3) 0.018(3) 0.029(3) 0.005(2) 0.007(2) -0.005(2) C15 0.021(3) 0.025(3) 0.037(4) 0.001(3) 0.008(2) 0.000(2) C5 0.021(3) 0.034(3) 0.033(3) -0.006(3) 0.008(3) -0.008(3) C7 0.023(3) 0.027(3) 0.009(3) 0.001(2) -0.004(2) 0.002(2) C12 0.022(3) 0.029(3) 0.032(4) 0.003(3) -0.003(2) -0.004(3) C13 0.026(3) 0.027(3) 0.015(3) 0.003(2) -0.001(2) -0.001(2) C14 0.014(3) 0.019(3) 0.011(3) 0.004(2) -0.008(2) -0.003(2) C17 0.023(3) 0.040(4) 0.026(3) 0.013(3) -0.002(2) 0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 C15 1.946(5) . ? Ga1 C16 1.960(5) . ? Ga1 N1 1.985(4) . ? Ga1 N3 1.988(4) . ? Ga2 C18 1.947(5) . ? Ga2 C17 1.954(5) . ? Ga2 N4 1.993(4) . ? Ga2 N2 2.007(4) . ? N1 C1 1.334(6) . ? N1 C2 1.400(6) . ? N3 C8 1.324(6) . ? N3 C9 1.384(6) . ? N2 C1 1.327(5) . ? N2 C3 1.393(6) . ? N4 C8 1.339(6) 3_765 ? N4 C14 1.405(5) . ? C10 C11 1.381(7) . ? C10 C9 1.393(6) . ? C10 H10 0.9500 . ? C11 C12 1.383(7) . ? C11 H11 0.9500 . ? C9 C14 1.397(6) 3_765 ? C1 H1 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C8 N4 1.339(6) 3_765 ? C8 H8 0.9500 . ? C4 C5 1.372(7) . ? C4 C3 1.375(6) . ? C4 H4 0.9500 . ? C3 C2 1.390(6) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C2 C7 1.397(6) . ? C6 C7 1.371(6) . ? C6 C5 1.389(7) . ? C6 H6 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C5 H5 0.9500 . ? C7 H7 0.9500 . ? C12 C13 1.372(7) . ? C12 H12 0.9500 . ? C13 C14 1.390(7) 3_765 ? C13 H13 0.9500 . ? C14 C13 1.390(7) 3_765 ? C14 C9 1.397(6) 3_765 ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 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 C15 Ga1 C16 124.9(2) . . ? C15 Ga1 N1 106.60(19) . . ? C16 Ga1 N1 110.39(18) . . ? C15 Ga1 N3 108.3(2) . . ? C16 Ga1 N3 106.64(18) . . ? N1 Ga1 N3 96.37(15) . . ? C18 Ga2 C17 125.9(2) . . ? C18 Ga2 N4 108.38(19) . . ? C17 Ga2 N4 108.2(2) . . ? C18 Ga2 N2 110.80(19) . . ? C17 Ga2 N2 103.00(19) . . ? N4 Ga2 N2 96.59(15) . . ? C1 N1 C2 104.0(4) . . ? C1 N1 Ga1 126.5(3) . . ? C2 N1 Ga1 129.1(3) . . ? C8 N3 C9 104.5(4) . . ? C8 N3 Ga1 129.6(3) . . ? C9 N3 Ga1 125.9(3) . . ? C1 N2 C3 105.1(4) . . ? C1 N2 Ga2 125.5(3) . . ? C3 N2 Ga2 129.4(3) . . ? C8 N4 C14 104.1(4) 3_765 . ? C8 N4 Ga2 125.2(3) 3_765 . ? C14 N4 Ga2 130.5(3) . . ? C11 C10 C9 117.2(5) . . ? C11 C10 H10 121.4 . . ? C9 C10 H10 121.4 . . ? C10 C11 C12 121.1(5) . . ? C10 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? N3 C9 C10 130.2(5) . . ? N3 C9 C14 108.7(4) . 3_765 ? C10 C9 C14 121.0(4) . 3_765 ? N2 C1 N1 115.2(4) . . ? N2 C1 H1 122.4 . . ? N1 C1 H1 122.4 . . ? Ga1 C16 H16A 109.5 . . ? Ga1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? Ga1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N3 C8 N4 115.6(4) . 3_765 ? N3 C8 H8 122.2 . . ? N4 C8 H8 122.2 3_765 . ? C5 C4 C3 117.8(5) . . ? C5 C4 H4 121.1 . . ? C3 C4 H4 121.1 . . ? C4 C3 C2 121.0(5) . . ? C4 C3 N2 131.6(5) . . ? C2 C3 N2 107.4(4) . . ? Ga2 C18 H18A 109.5 . . ? Ga2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Ga2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C3 C2 C7 121.5(4) . . ? C3 C2 N1 108.4(4) . . ? C7 C2 N1 130.1(4) . . ? C7 C6 C5 122.3(5) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? Ga1 C15 H15A 109.5 . . ? Ga1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? Ga1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 C5 C6 121.0(5) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C6 C7 C2 116.2(5) . . ? C6 C7 H7 121.9 . . ? C2 C7 H7 121.9 . . ? C13 C12 C11 122.7(5) . . ? C13 C12 H12 118.7 . . ? C11 C12 H12 118.7 . . ? C12 C13 C14 116.7(5) . 3_765 ? C12 C13 H13 121.7 . . ? C14 C13 H13 121.7 3_765 . ? C13 C14 C9 121.3(4) 3_765 3_765 ? C13 C14 N4 131.6(4) 3_765 . ? C9 C14 N4 107.0(4) 3_765 . ? Ga2 C17 H17A 109.5 . . ? Ga2 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? Ga2 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? 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 C15 Ga1 N1 C1 -5.8(4) . . . . ? C16 Ga1 N1 C1 132.5(4) . . . . ? N3 Ga1 N1 C1 -117.1(4) . . . . ? C15 Ga1 N1 C2 -177.1(4) . . . . ? C16 Ga1 N1 C2 -38.8(4) . . . . ? N3 Ga1 N1 C2 71.6(4) . . . . ? C15 Ga1 N3 C8 -104.0(4) . . . . ? C16 Ga1 N3 C8 119.4(4) . . . . ? N1 Ga1 N3 C8 5.8(4) . . . . ? C15 Ga1 N3 C9 73.7(4) . . . . ? C16 Ga1 N3 C9 -62.9(4) . . . . ? N1 Ga1 N3 C9 -176.5(4) . . . . ? C18 Ga2 N2 C1 -121.9(4) . . . . ? C17 Ga2 N2 C1 15.1(4) . . . . ? N4 Ga2 N2 C1 125.6(4) . . . . ? C18 Ga2 N2 C3 55.6(4) . . . . ? C17 Ga2 N2 C3 -167.4(4) . . . . ? N4 Ga2 N2 C3 -56.9(4) . . . . ? C18 Ga2 N4 C8 -150.5(4) . . . 3_765 ? C17 Ga2 N4 C8 70.0(4) . . . 3_765 ? N2 Ga2 N4 C8 -36.0(4) . . . 3_765 ? C18 Ga2 N4 C14 34.0(4) . . . . ? C17 Ga2 N4 C14 -105.4(4) . . . . ? N2 Ga2 N4 C14 148.5(4) . . . . ? C9 C10 C11 C12 0.1(8) . . . . ? C8 N3 C9 C10 -179.3(5) . . . . ? Ga1 N3 C9 C10 2.5(7) . . . . ? C8 N3 C9 C14 0.3(5) . . . 3_765 ? Ga1 N3 C9 C14 -177.8(3) . . . 3_765 ? C11 C10 C9 N3 -179.0(5) . . . . ? C11 C10 C9 C14 1.3(7) . . . 3_765 ? C3 N2 C1 N1 0.0(5) . . . . ? Ga2 N2 C1 N1 178.0(3) . . . . ? C2 N1 C1 N2 0.3(5) . . . . ? Ga1 N1 C1 N2 -172.8(3) . . . . ? C9 N3 C8 N4 0.5(5) . . . 3_765 ? Ga1 N3 C8 N4 178.6(3) . . . 3_765 ? C5 C4 C3 C2 0.6(7) . . . . ? C5 C4 C3 N2 179.8(5) . . . . ? C1 N2 C3 C4 -179.5(5) . . . . ? Ga2 N2 C3 C4 2.6(8) . . . . ? C1 N2 C3 C2 -0.3(5) . . . . ? Ga2 N2 C3 C2 -178.2(3) . . . . ? C4 C3 C2 C7 0.6(7) . . . . ? N2 C3 C2 C7 -178.7(4) . . . . ? C4 C3 C2 N1 179.8(4) . . . . ? N2 C3 C2 N1 0.4(5) . . . . ? C1 N1 C2 C3 -0.4(5) . . . . ? Ga1 N1 C2 C3 172.3(3) . . . . ? C1 N1 C2 C7 178.6(5) . . . . ? Ga1 N1 C2 C7 -8.6(7) . . . . ? C3 C4 C5 C6 -1.4(8) . . . . ? C7 C6 C5 C4 0.9(8) . . . . ? C5 C6 C7 C2 0.4(7) . . . . ? C3 C2 C7 C6 -1.1(7) . . . . ? N1 C2 C7 C6 179.9(5) . . . . ? C10 C11 C12 C13 -1.9(8) . . . . ? C11 C12 C13 C14 2.1(8) . . . 3_765 ? C8 N4 C14 C13 179.0(5) 3_765 . . 3_765 ? Ga2 N4 C14 C13 -4.8(8) . . . 3_765 ? C8 N4 C14 C9 -1.3(5) 3_765 . . 3_765 ? Ga2 N4 C14 C9 174.9(3) . . . 3_765 ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.671 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.110 #===END data_complex_3 _database_code_depnum_ccdc_archive 'CCDC 803987' #TrackingRef '- complexes cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C76 H88 Al4 N8' _chemical_formula_weight 1221.46 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 Tetragonal _symmetry_space_group_name_H-M P-42(1)c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 16.6460(18) _cell_length_b 16.6460(18) _cell_length_c 12.909(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3577.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas 1.134 _exptl_crystal_density_diffrn 1.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9598 _exptl_absorpt_correction_T_max 0.9704 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16006 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.09 _reflns_number_total 3155 _reflns_number_gt 2921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0530P)^2^+0.5297P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(4) _refine_ls_number_reflns 3155 _refine_ls_number_parameters 225 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.050 _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 Al1 Al 0.70696(3) 0.63769(3) 0.97642(5) 0.01880(16) Uani 1 1 d . . . N1 N 0.69619(9) 0.53307(9) 1.04062(13) 0.0189(4) Uani 1 1 d . . . N2 N 0.59648(9) 0.66248(10) 0.93854(13) 0.0202(4) Uani 1 1 d . . . C1 C 0.63055(15) 0.46577(13) 0.89053(17) 0.0289(5) Uani 1 1 d . . . H1A H 0.5718 0.4690 0.8928 0.145(19) Uiso 1 1 calc R . . H1B H 0.6466 0.4157 0.8563 0.079(11) Uiso 1 1 calc R . . H1C H 0.6518 0.5117 0.8517 0.067(9) Uiso 1 1 calc R . . C2 C 0.66310(11) 0.46711(12) 0.99815(15) 0.0184(4) Uani 1 1 d . . . C3 C 0.72004(12) 0.50972(11) 1.13995(16) 0.0193(4) Uani 1 1 d . . . C4 C 0.75973(13) 0.55184(12) 1.21796(17) 0.0261(5) Uani 1 1 d . . . H4 H 0.7752 0.6063 1.2086 0.013(5) Uiso 1 1 calc R . . C5 C 0.77575(15) 0.51200(13) 1.30892(17) 0.0316(5) Uani 1 1 d . . . H5 H 0.8028 0.5394 1.3632 0.021(5) Uiso 1 1 calc R . . C6 C 0.57035(12) 0.69838(12) 0.84633(16) 0.0198(4) Uani 1 1 d . . . C7 C 0.61025(13) 0.71441(14) 0.75382(16) 0.0287(5) Uani 1 1 d . . . H7 H 0.6647 0.6993 0.7439 0.026(6) Uiso 1 1 calc R . . C8 C 0.56744(13) 0.75317(15) 0.67708(18) 0.0330(6) Uani 1 1 d . . . H8 H 0.5931 0.7647 0.6130 0.045(8) Uiso 1 1 calc R . . C9 C 0.73763(14) 0.72048(13) 1.07606(17) 0.0298(5) Uani 1 1 d . . . H9A H 0.7933 0.7117 1.0981 0.045(7) Uiso 1 1 calc R . . H9B H 0.7021 0.7177 1.1365 0.054(8) Uiso 1 1 calc R . . H9C H 0.7329 0.7735 1.0436 0.047(7) Uiso 1 1 calc R . . C10 C 0.77773(12) 0.62657(14) 0.85660(17) 0.0276(5) Uani 1 1 d . . . H10A H 0.7527 0.5908 0.8056 0.047(8) Uiso 1 1 calc R . . H10B H 0.8293 0.6039 0.8788 0.033(6) Uiso 1 1 calc R . . H10C H 0.7867 0.6795 0.8253 0.046(7) Uiso 1 1 calc R . . C11 C 0.8095(3) 0.87696(18) 0.8606(2) 0.0752(12) Uani 1 1 d DU . . H11 H 0.8113 0.8214 0.8440 0.069(10) Uiso 1 1 calc R . . C12 C 0.8791(3) 0.91823(18) 0.8739(2) 0.0666(10) Uani 1 1 d DU . . H12 H 0.9293 0.8918 0.8661 0.072(11) Uiso 1 1 calc R . . C13 C 0.8765(2) 0.99833(18) 0.8989(2) 0.0639(9) Uani 1 1 d DU . . H13 H 0.9251 1.0273 0.9089 0.082(12) Uiso 1 1 calc R . . C14 C 0.8040(2) 1.03661(16) 0.9095(2) 0.0587(9) Uani 1 1 d DU . . H14 H 0.8027 1.0920 0.9269 0.055(8) Uiso 1 1 calc R . . C15 C 0.7336(2) 0.99588(18) 0.8952(2) 0.0604(9) Uani 1 1 d DU . . H15 H 0.6835 1.0226 0.9018 0.096(14) Uiso 1 1 calc R . . C16 C 0.7367(3) 0.9145(2) 0.8708(2) 0.0698(10) Uani 1 1 d DU . . H16 H 0.6884 0.8850 0.8612 0.076(11) Uiso 1 1 calc R . . C17 C 0.9604(3) 0.4914(3) 0.1102(3) 0.114(2) Uani 1 1 d DU . . H17 H 0.9325 0.4859 0.1741 0.123(16) Uiso 1 1 calc R . . C18 C 0.9195(3) 0.4820(3) 0.0177(3) 0.0923(14) Uani 1 1 d DU . . H18 H 0.8638 0.4695 0.0176 0.084(12) Uiso 1 1 calc R . . C19 C 0.9602(2) 0.4908(2) -0.0736(3) 0.0803(13) Uani 1 1 d DU . . H19 H 0.9327 0.4840 -0.1375 0.082(11) 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 0.0183(3) 0.0194(3) 0.0187(3) 0.0027(3) -0.0014(3) -0.0013(2) N1 0.0193(8) 0.0213(8) 0.0161(9) 0.0013(7) -0.0019(7) -0.0005(7) N2 0.0193(8) 0.0229(9) 0.0185(9) 0.0034(7) -0.0002(7) 0.0025(7) C1 0.0388(13) 0.0255(12) 0.0223(12) 0.0023(9) -0.0108(10) -0.0032(10) C2 0.0200(10) 0.0192(9) 0.0160(11) 0.0003(7) -0.0005(8) 0.0001(7) C3 0.0180(10) 0.0207(10) 0.0190(10) 0.0024(8) -0.0012(8) 0.0024(8) C4 0.0330(12) 0.0194(11) 0.0259(12) -0.0001(9) -0.0058(10) -0.0042(9) C5 0.0428(14) 0.0296(12) 0.0225(12) -0.0024(9) -0.0133(11) -0.0057(10) C6 0.0214(10) 0.0208(10) 0.0171(10) 0.0023(8) -0.0018(8) 0.0024(8) C7 0.0214(11) 0.0398(13) 0.0250(12) 0.0069(10) 0.0042(9) 0.0051(10) C8 0.0260(12) 0.0516(15) 0.0214(12) 0.0134(11) 0.0037(9) 0.0025(11) C9 0.0389(13) 0.0248(11) 0.0257(13) 0.0012(9) -0.0058(10) -0.0068(10) C10 0.0226(11) 0.0327(12) 0.0276(12) 0.0059(10) 0.0035(9) 0.0026(10) C11 0.166(4) 0.0319(16) 0.0282(16) 0.0003(13) 0.016(2) -0.001(2) C12 0.128(3) 0.0398(17) 0.0316(17) -0.0036(13) -0.0184(19) 0.0206(19) C13 0.101(3) 0.0472(17) 0.0432(18) -0.0082(14) -0.0350(18) 0.0178(18) C14 0.102(3) 0.0333(15) 0.0406(16) -0.0009(13) -0.0293(17) 0.0099(16) C15 0.097(3) 0.0499(17) 0.0338(16) 0.0080(14) -0.0041(17) 0.0000(18) C16 0.123(3) 0.0532(19) 0.0335(18) 0.0015(14) 0.011(2) -0.030(2) C17 0.126(4) 0.164(5) 0.051(2) 0.017(3) 0.017(2) 0.109(4) C18 0.083(3) 0.128(3) 0.066(2) 0.018(2) 0.011(2) 0.070(2) C19 0.077(2) 0.114(3) 0.050(2) 0.000(2) -0.0057(17) 0.066(2) _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 1.9369(17) . ? Al1 N2 1.9471(17) . ? Al1 C9 1.953(2) . ? Al1 C10 1.953(2) . ? N1 C2 1.345(3) . ? N1 C3 1.397(3) . ? N2 C2 1.337(3) 4_657 ? N2 C6 1.401(3) . ? C1 C2 1.491(3) . ? C2 N2 1.337(3) 3_567 ? C3 C6 1.392(3) 3_567 ? C3 C4 1.394(3) . ? C4 C5 1.375(3) . ? C5 C8 1.387(3) 3_567 ? C6 C3 1.392(3) 4_657 ? C6 C7 1.392(3) . ? C7 C8 1.380(3) . ? C8 C5 1.387(3) 4_657 ? C11 C12 1.358(5) . ? C11 C16 1.369(5) . ? C12 C13 1.372(4) . ? C13 C14 1.372(5) . ? C14 C15 1.366(4) . ? C15 C16 1.392(4) . ? C17 C17 1.350(10) 2_765 ? C17 C18 1.384(5) . ? C18 C19 1.368(5) . ? C19 C19 1.360(8) 2_765 ? 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 N2 102.16(7) . . ? N1 Al1 C9 112.14(8) . . ? N2 Al1 C9 105.23(9) . . ? N1 Al1 C10 108.03(8) . . ? N2 Al1 C10 113.01(8) . . ? C9 Al1 C10 115.51(10) . . ? C2 N1 C3 105.26(15) . . ? C2 N1 Al1 126.68(13) . . ? C3 N1 Al1 128.05(13) . . ? C2 N2 C6 105.68(16) 4_657 . ? C2 N2 Al1 126.56(14) 4_657 . ? C6 N2 Al1 126.65(13) . . ? N2 C2 N1 113.59(16) 3_567 . ? N2 C2 C1 123.69(18) 3_567 . ? N1 C2 C1 122.72(18) . . ? C6 C3 C4 120.83(19) 3_567 . ? C6 C3 N1 108.02(17) 3_567 . ? C4 C3 N1 131.14(18) . . ? C5 C4 C3 117.81(19) . . ? C4 C5 C8 121.3(2) . 3_567 ? C3 C6 C7 121.07(19) 4_657 . ? C3 C6 N2 107.44(17) 4_657 . ? C7 C6 N2 131.48(18) . . ? C8 C7 C6 117.32(19) . . ? C7 C8 C5 121.7(2) . 4_657 ? C12 C11 C16 120.8(3) . . ? C11 C12 C13 119.6(4) . . ? C12 C13 C14 120.2(4) . . ? C15 C14 C13 120.7(3) . . ? C14 C15 C16 118.8(3) . . ? C11 C16 C15 119.9(3) . . ? C17 C17 C18 120.3(3) 2_765 . ? C19 C18 C17 119.2(4) . . ? C19 C19 C18 120.5(3) 2_765 . ? 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 Al1 N1 C2 55.69(17) . . . . ? C9 Al1 N1 C2 167.89(16) . . . . ? C10 Al1 N1 C2 -63.69(18) . . . . ? N2 Al1 N1 C3 -123.78(16) . . . . ? C9 Al1 N1 C3 -11.58(19) . . . . ? C10 Al1 N1 C3 116.84(17) . . . . ? N1 Al1 N2 C2 54.74(17) . . . 4_657 ? C9 Al1 N2 C2 -62.53(18) . . . 4_657 ? C10 Al1 N2 C2 170.55(16) . . . 4_657 ? N1 Al1 N2 C6 -139.06(16) . . . . ? C9 Al1 N2 C6 103.67(17) . . . . ? C10 Al1 N2 C6 -23.25(19) . . . . ? C3 N1 C2 N2 0.8(2) . . . 3_567 ? Al1 N1 C2 N2 -178.77(12) . . . 3_567 ? C3 N1 C2 C1 -179.10(19) . . . . ? Al1 N1 C2 C1 1.3(3) . . . . ? C2 N1 C3 C6 -1.2(2) . . . 3_567 ? Al1 N1 C3 C6 178.40(13) . . . 3_567 ? C2 N1 C3 C4 177.8(2) . . . . ? Al1 N1 C3 C4 -2.7(3) . . . . ? C6 C3 C4 C5 -0.8(3) 3_567 . . . ? N1 C3 C4 C5 -179.6(2) . . . . ? C3 C4 C5 C8 -0.1(4) . . . 3_567 ? C2 N2 C6 C3 0.6(2) 4_657 . . 4_657 ? Al1 N2 C6 C3 -167.88(13) . . . 4_657 ? C2 N2 C6 C7 179.6(2) 4_657 . . . ? Al1 N2 C6 C7 11.1(3) . . . . ? C3 C6 C7 C8 0.6(3) 4_657 . . . ? N2 C6 C7 C8 -178.2(2) . . . . ? C6 C7 C8 C5 0.3(4) . . . 4_657 ? C16 C11 C12 C13 0.6(5) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C12 C13 C14 C15 -0.2(5) . . . . ? C13 C14 C15 C16 0.7(4) . . . . ? C12 C11 C16 C15 0.0(5) . . . . ? C14 C15 C16 C11 -0.6(5) . . . . ? C17 C17 C18 C19 -0.5(8) 2_765 . . . ? C17 C18 C19 C19 -0.5(7) . . . 2_765 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.257 _refine_diff_density_min -0.128 _refine_diff_density_rms 0.040 #===END data_complex_4 _database_code_depnum_ccdc_archive 'CCDC 803988' #TrackingRef '- complexes cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C76 H88 Ga4 N8' _chemical_formula_weight 1392.42 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' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P-42(1)c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-y+1/2, -x+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 16.8104(15) _cell_length_b 16.8104(15) _cell_length_c 13.0585(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3690.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 1.253 _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 1.490 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5942 _exptl_absorpt_correction_T_max 0.7071 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 34450 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3251 _reflns_number_gt 3084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0405P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(10) _refine_ls_number_reflns 3251 _refine_ls_number_parameters 224 _refine_ls_number_restraints 92 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0567 _refine_ls_wR_factor_gt 0.0563 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.041 _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 Ga1 Ga 0.642510(11) 0.707865(12) 0.975777(19) 0.02931(8) Uani 1 1 d . . . N1 N 0.69678(9) 0.46484(9) 0.95870(12) 0.0278(4) Uani 1 1 d . . . N2 N 0.66501(10) 0.59375(9) 0.93835(13) 0.0290(4) Uani 1 1 d . . . C1 C 0.63045(16) 0.53224(14) 1.10665(18) 0.0433(6) Uani 1 1 d . . . H1A H 0.6354 0.5861 1.1348 0.112(14) Uiso 1 1 calc R . . H1B H 0.6597 0.4948 1.1501 0.138(15) Uiso 1 1 calc R . . H1C H 0.5742 0.5170 1.1046 0.16(2) Uiso 1 1 calc R . . C2 C 0.66404(10) 0.53048(11) 1.00055(14) 0.0274(4) Uani 1 1 d . . . C3 C 0.72172(11) 0.48769(12) 0.86130(15) 0.0293(4) Uani 1 1 d . . . C4 C 0.76182(15) 0.44592(13) 0.78449(17) 0.0424(5) Uani 1 1 d . . . H4 H 0.7763 0.3918 0.7937 0.050(7) Uiso 1 1 calc R . . C5 C 0.77971(17) 0.48543(15) 0.69534(18) 0.0541(7) Uani 1 1 d . . . H5 H 0.8074 0.4583 0.6424 0.058(8) Uiso 1 1 calc R . . C6 C 0.75789(19) 0.56490(16) 0.68120(19) 0.0566(7) Uani 1 1 d . . . H6 H 0.7697 0.5904 0.6181 0.062(8) Uiso 1 1 calc R . . C7 C 0.71958(16) 0.60700(13) 0.75722(18) 0.0470(6) Uani 1 1 d . . . H7 H 0.7058 0.6613 0.7477 0.066(8) Uiso 1 1 calc R . . C8 C 0.70169(12) 0.56801(12) 0.84799(15) 0.0316(4) Uani 1 1 d . . . C9 C 0.62809(16) 0.77554(13) 0.85447(19) 0.0468(6) Uani 1 1 d . . . H9A H 0.6016 0.8251 0.8745 0.088(11) Uiso 1 1 calc R . . H9B H 0.5954 0.7475 0.8039 0.068(9) Uiso 1 1 calc R . . H9C H 0.6801 0.7878 0.8245 0.091(11) Uiso 1 1 calc R . . C10 C 0.72549(14) 0.73327(17) 1.07763(19) 0.0516(6) Uani 1 1 d . . . H10A H 0.7781 0.7256 1.0469 0.073(9) Uiso 1 1 calc R . . H10B H 0.7198 0.6981 1.1370 0.070(9) Uiso 1 1 calc R . . H10C H 0.7198 0.7887 1.0996 0.078(10) Uiso 1 1 calc R . . C11 C 0.6964(3) 0.4636(2) 0.4094(3) 0.1142(17) Uani 1 1 d DU . . H11 H 0.6972 0.4089 0.4272 0.119(14) Uiso 1 1 calc R . . C12 C 0.7661(4) 0.5030(3) 0.3955(3) 0.1164(15) Uani 1 1 d DU . . H12 H 0.8155 0.4761 0.4026 0.18(3) Uiso 1 1 calc R . . C13 C 0.7637(4) 0.5830(3) 0.3708(3) 0.132(2) Uani 1 1 d DU . . H13 H 0.8116 0.6120 0.3610 0.16(2) Uiso 1 1 calc R . . C14 C 0.6917(5) 0.6201(3) 0.3605(3) 0.135(2) Uani 1 1 d DU . . H14 H 0.6902 0.6751 0.3439 0.23(3) Uiso 1 1 calc R . . C15 C 0.6236(4) 0.5805(3) 0.3734(3) 0.131(2) Uani 1 1 d DU . . H15 H 0.5741 0.6072 0.3655 0.125(18) Uiso 1 1 calc R . . C16 C 0.6252(4) 0.5015(3) 0.3981(3) 0.1284(19) Uani 1 1 d DU . . H156 H 0.5769 0.4730 0.4074 0.17(3) Uiso 1 1 calc R . . C17 C 0.9595(3) 0.5083(3) 1.0783(4) 0.1206(18) Uani 1 1 d DU . . H17 H 0.9316 0.5146 1.1411 0.095(12) Uiso 1 1 calc R . . C18 C 0.9211(3) 0.5155(4) 0.9886(4) 0.152(2) Uani 1 1 d DU . . H18 H 0.8654 0.5252 0.9886 0.145(19) Uiso 1 1 calc R . . C19 C 0.9602(4) 0.5091(5) 0.8977(4) 0.190(4) Uani 1 1 d DU . . H19 H 0.9328 0.5172 0.8350 0.26(4) 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 Ga1 0.03007(12) 0.02708(12) 0.03077(12) -0.00241(10) 0.00540(10) -0.00338(8) N1 0.0303(8) 0.0283(8) 0.0246(9) 0.0018(6) 0.0041(7) 0.0020(6) N2 0.0358(9) 0.0259(8) 0.0252(8) -0.0008(7) 0.0061(7) 0.0022(7) C1 0.0584(16) 0.0366(12) 0.0350(12) 0.0013(10) 0.0136(11) 0.0068(11) C2 0.0259(9) 0.0296(9) 0.0268(11) -0.0002(7) 0.0033(7) -0.0008(8) C3 0.0291(10) 0.0299(10) 0.0289(9) 0.0012(8) 0.0054(8) -0.0010(8) C4 0.0553(14) 0.0315(12) 0.0403(12) -0.0002(10) 0.0168(11) 0.0065(10) C5 0.0791(19) 0.0436(14) 0.0398(13) -0.0012(11) 0.0297(13) 0.0094(13) C6 0.092(2) 0.0423(14) 0.0355(12) 0.0075(11) 0.0252(13) 0.0055(14) C7 0.0737(17) 0.0320(12) 0.0353(12) 0.0069(10) 0.0168(12) 0.0086(11) C8 0.0344(10) 0.0311(10) 0.0293(10) -0.0011(8) 0.0045(9) 0.0020(9) C9 0.0606(16) 0.0337(12) 0.0462(14) 0.0094(11) 0.0133(12) 0.0064(11) C10 0.0352(13) 0.0729(18) 0.0468(14) -0.0160(13) 0.0025(11) -0.0164(12) C11 0.205(5) 0.064(2) 0.073(2) 0.0078(19) 0.052(3) 0.022(3) C12 0.198(5) 0.093(3) 0.059(2) -0.010(2) -0.001(3) 0.007(3) C13 0.237(6) 0.095(3) 0.065(2) 0.000(3) -0.035(4) -0.044(4) C14 0.293(8) 0.063(3) 0.048(2) 0.0007(19) -0.030(4) -0.003(3) C15 0.252(6) 0.078(3) 0.063(2) 0.005(2) 0.043(3) 0.036(4) C16 0.207(5) 0.091(3) 0.086(3) 0.023(2) 0.070(3) 0.050(4) C17 0.116(3) 0.158(4) 0.087(3) -0.007(3) 0.013(2) -0.087(4) C18 0.128(4) 0.212(6) 0.118(4) 0.027(4) -0.016(3) -0.107(4) C19 0.181(6) 0.294(9) 0.095(3) 0.031(5) -0.021(3) -0.160(7) _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 Ga1 C9 1.965(2) . ? Ga1 C10 1.974(2) . ? Ga1 N1 2.0059(15) 4_657 ? Ga1 N2 2.0154(15) . ? N1 C2 1.349(2) . ? N1 C3 1.393(2) . ? N1 Ga1 2.0059(15) 3_567 ? N2 C2 1.338(2) . ? N2 C8 1.400(3) . ? C1 C2 1.496(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C4 1.398(3) . ? C3 C8 1.402(3) . ? C4 C5 1.374(3) . ? C4 H4 0.9500 . ? C5 C6 1.398(4) . ? C5 H5 0.9500 . ? C6 C7 1.379(3) . ? C6 H6 0.9500 . ? C7 C8 1.387(3) . ? C7 H7 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.359(6) . ? C11 C16 1.362(6) . ? C11 H11 0.9500 . ? C12 C13 1.384(6) . ? C12 H12 0.9500 . ? C13 C14 1.367(7) . ? C13 H13 0.9500 . ? C14 C15 1.335(7) . ? C14 H14 0.9500 . ? C15 C16 1.368(6) . ? C15 H15 0.9500 . ? C16 H156 0.9500 . ? C17 C18 1.343(6) . ? C17 C17 1.391(10) 2_765 ? C17 H17 0.9500 . ? C18 C19 1.361(7) . ? C18 H18 0.9500 . ? C19 C19 1.371(15) 2_765 ? C19 H19 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 C9 Ga1 C10 120.33(12) . . ? C9 Ga1 N1 106.65(9) . 4_657 ? C10 Ga1 N1 111.62(8) . 4_657 ? C9 Ga1 N2 112.25(8) . . ? C10 Ga1 N2 103.69(10) . . ? N1 Ga1 N2 100.60(6) 4_657 . ? C2 N1 C3 105.50(15) . . ? C2 N1 Ga1 126.95(12) . 3_567 ? C3 N1 Ga1 127.55(13) . 3_567 ? C2 N2 C8 105.74(15) . . ? C2 N2 Ga1 127.37(13) . . ? C8 N2 Ga1 125.54(13) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 N1 113.53(15) . . ? N2 C2 C1 123.42(17) . . ? N1 C2 C1 123.05(17) . . ? N1 C3 C4 131.44(19) . . ? N1 C3 C8 107.83(17) . . ? C4 C3 C8 120.70(19) . . ? C5 C4 C3 118.1(2) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C4 C5 C6 121.1(2) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 121.2(2) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 118.3(2) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C7 C8 N2 132.04(19) . . ? C7 C8 C3 120.57(19) . . ? N2 C8 C3 107.39(17) . . ? Ga1 C9 H9A 109.5 . . ? Ga1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? Ga1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? Ga1 C10 H10A 109.5 . . ? Ga1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? Ga1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 121.1(4) . . ? C12 C11 H11 119.5 . . ? C16 C11 H11 119.5 . . ? C11 C12 C13 118.6(6) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 119.5(5) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C15 C14 C13 121.3(4) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 119.8(5) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 119.8(6) . . ? C11 C16 H156 120.1 . . ? C15 C16 H156 120.1 . . ? C18 C17 C17 119.2(4) . 2_765 ? C18 C17 H17 120.4 . . ? C17 C17 H17 120.4 2_765 . ? C17 C18 C19 121.4(6) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C19 119.3(4) . 2_765 ? C18 C19 H19 120.4 . . ? C19 C19 H19 120.4 2_765 . ? 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 C9 Ga1 N2 C2 -167.41(17) . . . . ? C10 Ga1 N2 C2 61.20(17) . . . . ? N1 Ga1 N2 C2 -54.36(17) 4_657 . . . ? C9 Ga1 N2 C8 27.80(19) . . . . ? C10 Ga1 N2 C8 -103.60(17) . . . . ? N1 Ga1 N2 C8 140.85(16) 4_657 . . . ? C8 N2 C2 N1 -0.2(2) . . . . ? Ga1 N2 C2 N1 -167.43(13) . . . . ? C8 N2 C2 C1 179.35(19) . . . . ? Ga1 N2 C2 C1 12.2(3) . . . . ? C3 N1 C2 N2 0.5(2) . . . . ? Ga1 N1 C2 N2 179.98(12) 3_567 . . . ? C3 N1 C2 C1 -179.07(19) . . . . ? Ga1 N1 C2 C1 0.4(3) 3_567 . . . ? C2 N1 C3 C4 177.6(2) . . . . ? Ga1 N1 C3 C4 -1.9(3) 3_567 . . . ? C2 N1 C3 C8 -0.6(2) . . . . ? Ga1 N1 C3 C8 179.96(13) 3_567 . . . ? N1 C3 C4 C5 -179.0(2) . . . . ? C8 C3 C4 C5 -1.1(3) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C7 1.8(5) . . . . ? C5 C6 C7 C8 -1.2(4) . . . . ? C6 C7 C8 N2 179.0(2) . . . . ? C6 C7 C8 C3 -0.4(4) . . . . ? C2 N2 C8 C7 -179.6(3) . . . . ? Ga1 N2 C8 C7 -12.1(4) . . . . ? C2 N2 C8 C3 -0.1(2) . . . . ? Ga1 N2 C8 C3 167.35(13) . . . . ? N1 C3 C8 C7 180.0(2) . . . . ? C4 C3 C8 C7 1.6(3) . . . . ? N1 C3 C8 N2 0.5(2) . . . . ? C4 C3 C8 N2 -177.93(19) . . . . ? C16 C11 C12 C13 0.8(6) . . . . ? C11 C12 C13 C14 -0.3(6) . . . . ? C12 C13 C14 C15 -0.3(7) . . . . ? C13 C14 C15 C16 0.5(7) . . . . ? C12 C11 C16 C15 -0.6(6) . . . . ? C14 C15 C16 C11 0.0(7) . . . . ? C17 C17 C18 C19 -2.0(11) 2_765 . . . ? C17 C18 C19 C19 3.4(13) . . . 2_765 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.281 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.044