Supplementary Material (ESI) for Dalton Transactions This journal is (C) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 222 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Norbert Mitzel' _publ_contact_author_name 'Norbert Mitzel' _publ_contact_author_address ; Fakult\"at f\"ur Chemie Universit\"at Bielefeld Lehrstuhl f\"ur Anorganische Chemie u Universit\"atsstrasse 25 Bielefeld D-33615 GERMANY ; _publ_contact_author_email MITZEL@UNI-BIELEFELD.DE _publ_section_title ; Structural Diversity in Bishydroxylamine Complexes of Gallium ; # Attachment 'Compound_3a.cif' data_patr03 _database_code_depnum_ccdc_archive 'CCDC 668793' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2,2,4,5,5-Hexamethyl-2,5-digalla-3,6-dioxa-1,4-diazabicyclo[2,2,2]octan ; _chemical_name_common "N,N'-Bis-oxo-N,N'-dimethylethylenediamine tetramethyldigallate" _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H22 Ga2 N2 O2' _chemical_formula_weight 317.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.183(3) _cell_length_b 7.5160(18) _cell_length_c 16.303(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1370.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2000 _cell_measurement_theta_min 4.71 _cell_measurement_theta_max 25.58 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 3.914 _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 153(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 'STOE IPDS-1' _diffrn_measurement_method '\phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9857 _diffrn_reflns_av_R_equivalents 0.1875 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.71 _diffrn_reflns_theta_max 25.58 _reflns_number_total 1258 _reflns_number_gt 1173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS-1 software package' _computing_cell_refinement 'X-AREA (STOE 2003)' _computing_data_reduction 'X-AREA (STOE 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.01' _computing_publication_material 'SHELXTL 5.01' _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^)+(0.0699P)^2^+10.9479P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1258 _refine_ls_number_parameters 78 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.2063 _refine_ls_wR_factor_gt 0.2041 _refine_ls_goodness_of_fit_ref 1.272 _refine_ls_restrained_S_all 1.272 _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 Ga1 Ga 0.06548(7) 0.17386(11) 0.35266(6) 0.0254(4) Uani 1 1 d . . . N1 N -0.0863(6) 0.3007(8) 0.3118(5) 0.0254(14) Uani 1 1 d . . . O1 O -0.1428(5) 0.1924(6) 0.2508(4) 0.0277(12) Uani 1 1 d . . . C1 C 0.1358(9) 0.3376(13) 0.4345(6) 0.045(2) Uani 1 1 d . . . H1A H 0.2220 0.3159 0.4386 0.10(5) Uiso 1 1 calc R . . H1B H 0.0983 0.3173 0.4880 0.12(6) Uiso 1 1 calc R . . H1C H 0.1219 0.4609 0.4174 0.09(4) Uiso 1 1 calc R . . C2 C 0.0316(10) -0.0800(13) 0.3715(8) 0.051(3) Uani 1 1 d . . . H2A H 0.0950 -0.1522 0.3466 0.12(8) Uiso 1 1 calc R . . H2B H -0.0454 -0.1108 0.3466 0.03(2) Uiso 1 1 calc R . . H2C H 0.0285 -0.1033 0.4306 0.06(3) Uiso 1 1 calc R . . C3 C -0.1774(8) 0.3234(14) 0.3765(6) 0.043(2) Uani 1 1 d . . . H3A H -0.2458 0.3893 0.3543 0.05(3) Uiso 1 1 calc R . . H3B H -0.1428 0.3896 0.4225 0.03(2) Uiso 1 1 calc R . . H3C H -0.2041 0.2063 0.3956 0.03(2) Uiso 1 1 calc R . . C4 C -0.0570(7) 0.4770(10) 0.2762(6) 0.0310(19) Uani 1 1 d . . . H4A H -0.0473 0.5639 0.3213 0.04(3) Uiso 1 1 calc R . . H4B H -0.1249 0.5170 0.2419 0.03(2) 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 0.0245(6) 0.0219(6) 0.0300(6) 0.0031(3) -0.0025(3) -0.0065(3) N1 0.022(3) 0.020(3) 0.034(4) -0.007(3) 0.007(3) -0.003(2) O1 0.023(3) 0.023(2) 0.037(3) -0.015(2) 0.003(2) -0.006(2) C1 0.041(5) 0.053(6) 0.041(5) -0.001(4) -0.008(5) -0.022(4) C2 0.053(6) 0.036(5) 0.063(7) 0.022(5) -0.008(6) -0.016(5) C3 0.032(5) 0.056(6) 0.042(5) -0.025(5) 0.015(4) -0.003(4) C4 0.032(4) 0.012(3) 0.049(5) -0.005(3) -0.001(4) 0.003(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 O1 1.901(6) 3 ? Ga1 C2 1.969(9) . ? Ga1 C1 1.978(9) . ? Ga1 N1 2.058(7) . ? N1 O1 1.431(8) . ? N1 C3 1.477(11) . ? N1 C4 1.484(10) . ? O1 Ga1 1.901(6) 3 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C4 1.535(16) 3 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ga1 C2 107.3(4) 3 . ? O1 Ga1 C1 111.8(4) 3 . ? C2 Ga1 C1 125.0(5) . . ? O1 Ga1 N1 93.1(3) 3 . ? C2 Ga1 N1 109.9(4) . . ? C1 Ga1 N1 105.0(4) . . ? O1 N1 C3 104.9(6) . . ? O1 N1 C4 109.5(6) . . ? C3 N1 C4 109.2(6) . . ? O1 N1 Ga1 109.0(4) . . ? C3 N1 Ga1 113.0(6) . . ? C4 N1 Ga1 111.0(5) . . ? N1 O1 Ga1 117.2(4) . 3 ? Ga1 C1 H1A 109.5 . . ? Ga1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Ga1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? Ga1 C2 H2A 109.5 . . ? Ga1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Ga1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C4 113.6(4) . 3 ? N1 C4 H4A 108.8 . . ? C4 C4 H4A 108.8 3 . ? N1 C4 H4B 108.8 . . ? C4 C4 H4B 108.8 3 . ? H4A C4 H4B 107.7 . . ? 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 O1 Ga1 N1 O1 65.5(4) 3 . . . ? C2 Ga1 N1 O1 -44.1(6) . . . . ? C1 Ga1 N1 O1 179.1(5) . . . . ? O1 Ga1 N1 C3 -178.3(6) 3 . . . ? C2 Ga1 N1 C3 72.1(7) . . . . ? C1 Ga1 N1 C3 -64.7(6) . . . . ? O1 Ga1 N1 C4 -55.2(6) 3 . . . ? C2 Ga1 N1 C4 -164.8(6) . . . . ? C1 Ga1 N1 C4 58.4(6) . . . . ? C3 N1 O1 Ga1 167.4(6) . . . 3 ? C4 N1 O1 Ga1 50.4(6) . . . 3 ? Ga1 N1 O1 Ga1 -71.2(5) . . . 3 ? O1 N1 C4 C4 -79.8(10) . . . 3 ? C3 N1 C4 C4 165.9(9) . . . 3 ? Ga1 N1 C4 C4 40.7(11) . . . 3 ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.58 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.999 _refine_diff_density_min -1.240 _refine_diff_density_rms 0.173 # Attachment 'Compound_3b.CIF' data_ppp _database_code_depnum_ccdc_archive 'CCDC 668794' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Di-tert.-Butyl-2,2,5,5-tetramethyl-2,5-digalla -3,6-dioxa-1,4-diazabicyclo[2,2,2]octane ; _chemical_name_common ; N,N'-Bis-oxo-N,N'-di-tert-butylethylenediamine tetramethyldigallate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H34 Ga2 N2 O2' _chemical_formula_weight 401.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.896(3) _cell_length_b 7.5020(15) _cell_length_c 17.432(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.90(3) _cell_angle_gamma 90.00 _cell_volume 1943.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 2000 _cell_measurement_theta_min 4.72 _cell_measurement_theta_max 25.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 2.776 _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 153(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 'STOE IPDS-1' _diffrn_measurement_method '\phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11029 _diffrn_reflns_av_R_equivalents 0.1254 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.72 _diffrn_reflns_theta_max 25.51 _reflns_number_total 1770 _reflns_number_gt 1657 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS-1 software package' _computing_cell_refinement 'X-AREA (STOE 2003)' _computing_data_reduction 'X-AREA (STOE 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.01' _computing_publication_material 'SHELXTL 5.01' _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^)+(0.0107P)^2^+4.8729P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1770 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0928 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.241 _refine_ls_restrained_S_all 1.241 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga1 Ga 0.55068(2) 0.60618(4) 0.84730(2) 0.02139(16) Uani 1 1 d . . . O1 O 0.39893(16) 0.6167(3) 0.74984(14) 0.0239(5) Uani 1 1 d . . . N1 N 0.43364(18) 0.7400(3) 0.80781(16) 0.0222(6) Uani 1 1 d . . . C1 C 0.6242(3) 0.7541(6) 0.9210(2) 0.0398(9) Uani 1 1 d . . . H1A H 0.6881 0.7291 0.9160 0.060 Uiso 1 1 calc R . . H1B H 0.6088 0.7263 0.9735 0.060 Uiso 1 1 calc R . . H1C H 0.6123 0.8804 0.9102 0.060 Uiso 1 1 calc R . . C2 C 0.5243(3) 0.3520(5) 0.8630(3) 0.0368(9) Uani 1 1 d . . . H2A H 0.5742 0.2796 0.8464 0.055 Uiso 1 1 calc R . . H2B H 0.4688 0.3197 0.8328 0.055 Uiso 1 1 calc R . . H2C H 0.5168 0.3302 0.9176 0.055 Uiso 1 1 calc R . . C3 C 0.3584(2) 0.7686(5) 0.8623(2) 0.0316(8) Uani 1 1 d . . . C4 C 0.4545(2) 0.9096(4) 0.7679(2) 0.0259(7) Uani 1 1 d . . . H4A H 0.4536 1.0089 0.8052 0.031 Uiso 1 1 calc R . . H4B H 0.4066 0.9324 0.7269 0.031 Uiso 1 1 calc R . . C31 C 0.3938(3) 0.8883(6) 0.9288(3) 0.0441(10) Uani 1 1 d . . . H31A H 0.3488 0.8955 0.9672 0.066 Uiso 1 1 calc R . . H31B H 0.4055 1.0079 0.9092 0.066 Uiso 1 1 calc R . . H31C H 0.4497 0.8381 0.9526 0.066 Uiso 1 1 calc R . . C32 C 0.3344(3) 0.5873(6) 0.8946(3) 0.0468(11) Uani 1 1 d . . . H32A H 0.2857 0.6015 0.9293 0.070 Uiso 1 1 calc R . . H32B H 0.3873 0.5364 0.9231 0.070 Uiso 1 1 calc R . . H32C H 0.3146 0.5075 0.8523 0.070 Uiso 1 1 calc R . . C33 C 0.2761(3) 0.8518(7) 0.8199(3) 0.0547(13) Uani 1 1 d . . . H33A H 0.2265 0.8554 0.8540 0.082 Uiso 1 1 calc R . . H33B H 0.2584 0.7803 0.7744 0.082 Uiso 1 1 calc R . . H33C H 0.2905 0.9733 0.8041 0.082 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 0.0240(2) 0.0196(2) 0.0203(2) 0.00225(14) -0.00070(15) -0.00240(13) O1 0.0254(11) 0.0225(11) 0.0238(12) -0.0064(9) 0.0015(9) -0.0049(9) N1 0.0266(14) 0.0184(12) 0.0217(14) -0.0039(11) 0.0038(11) -0.0034(10) C1 0.040(2) 0.047(2) 0.032(2) 0.0003(17) -0.0069(17) -0.0058(17) C2 0.043(2) 0.0232(17) 0.044(2) 0.0083(16) 0.0010(18) 0.0003(15) C3 0.0300(18) 0.0352(19) 0.0307(19) -0.0032(15) 0.0107(15) 0.0042(15) C4 0.0359(19) 0.0159(14) 0.0261(17) -0.0013(13) 0.0041(15) 0.0008(13) C31 0.055(3) 0.047(2) 0.033(2) -0.0098(18) 0.0182(19) -0.0033(19) C32 0.049(3) 0.041(2) 0.054(3) -0.002(2) 0.033(2) -0.0079(18) C33 0.037(2) 0.076(3) 0.052(3) -0.001(2) 0.012(2) 0.020(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 Ga1 O1 1.900(3) 2_656 ? Ga1 C2 1.970(3) . ? Ga1 C1 1.973(4) . ? Ga1 N1 2.088(3) . ? O1 N1 1.440(3) . ? O1 Ga1 1.900(3) 2_656 ? N1 C4 1.493(4) . ? N1 C3 1.533(4) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C33 1.522(6) . ? C3 C32 1.524(6) . ? C3 C31 1.531(5) . ? C4 C4 1.529(7) 2_656 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ga1 C2 105.00(15) 2_656 . ? O1 Ga1 C1 108.76(15) 2_656 . ? C2 Ga1 C1 124.13(17) . . ? O1 Ga1 N1 93.32(10) 2_656 . ? C2 Ga1 N1 109.98(14) . . ? C1 Ga1 N1 111.01(15) . . ? N1 O1 Ga1 120.50(19) . 2_656 ? O1 N1 C4 107.2(2) . . ? O1 N1 C3 106.4(2) . . ? C4 N1 C3 110.8(3) . . ? O1 N1 Ga1 100.04(17) . . ? C4 N1 Ga1 111.6(2) . . ? C3 N1 Ga1 119.5(2) . . ? Ga1 C1 H1A 109.5 . . ? Ga1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? Ga1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? Ga1 C2 H2A 109.5 . . ? Ga1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? Ga1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C33 C3 C32 110.1(4) . . ? C33 C3 C31 110.6(3) . . ? C32 C3 C31 108.7(3) . . ? C33 C3 N1 110.8(3) . . ? C32 C3 N1 107.7(3) . . ? C31 C3 N1 108.9(3) . . ? N1 C4 C4 114.1(2) . 2_656 ? N1 C4 H4A 108.7 . . ? C4 C4 H4A 108.7 2_656 . ? N1 C4 H4B 108.7 . . ? C4 C4 H4B 108.7 2_656 . ? H4A C4 H4B 107.6 . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 H32A 109.5 . . ? C3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C3 C33 H33A 109.5 . . ? C3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 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 Ga1 O1 N1 C4 39.2(3) 2_656 . . . ? Ga1 O1 N1 C3 157.7(2) 2_656 . . . ? Ga1 O1 N1 Ga1 -77.31(19) 2_656 . . . ? O1 Ga1 N1 O1 61.83(17) 2_656 . . . ? C2 Ga1 N1 O1 -45.4(2) . . . . ? C1 Ga1 N1 O1 173.4(2) . . . . ? O1 Ga1 N1 C4 -51.4(2) 2_656 . . . ? C2 Ga1 N1 C4 -158.6(2) . . . . ? C1 Ga1 N1 C4 60.2(3) . . . . ? O1 Ga1 N1 C3 177.3(2) 2_656 . . . ? C2 Ga1 N1 C3 70.0(3) . . . . ? C1 Ga1 N1 C3 -71.2(3) . . . . ? O1 N1 C3 C33 -62.3(4) . . . . ? C4 N1 C3 C33 53.9(4) . . . . ? Ga1 N1 C3 C33 -174.4(3) . . . . ? O1 N1 C3 C32 58.1(4) . . . . ? C4 N1 C3 C32 174.4(3) . . . . ? Ga1 N1 C3 C32 -53.9(4) . . . . ? O1 N1 C3 C31 175.9(3) . . . . ? C4 N1 C3 C31 -67.9(4) . . . . ? Ga1 N1 C3 C31 63.9(3) . . . . ? O1 N1 C4 C4 -82.0(4) . . . 2_656 ? C3 N1 C4 C4 162.3(3) . . . 2_656 ? Ga1 N1 C4 C4 26.6(4) . . . 2_656 ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.51 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.346 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.074 # Attachment 'Compound_4a.cif' data_serrano _database_code_depnum_ccdc_archive 'CCDC 668795' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Dimethyl-2,2,5,5-Tetrakis-isopropyl-2,5-digalla -3,6-dioxa-1,4-diazabicyclo[2,2,2]octan ; _chemical_name_common ; N,N'-Bis-oxo-N,N'-dimethylethylenediamine tetrakis.isopropyldigallate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H38 Ga2 N2 O2' _chemical_formula_weight 429.92 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4306(17) _cell_length_b 9.9648(18) _cell_length_c 13.183(2) _cell_angle_alpha 104.349(18) _cell_angle_beta 109.081(18) _cell_angle_gamma 101.892(18) _cell_volume 1077.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 4.57 _cell_measurement_theta_max 26.90 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 2.509 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.166 _exptl_absorpt_correction_T_max 0.478 _exptl_absorpt_process_details ; Absorption correction was done with the program ABSCOR from the IPDS-1 software package. ABSCOR works similar to the well known DIFABS, but reads and provides Fo^2^ values instead of Fo ones. ; _exptl_special_details ; ; _diffrn_ambient_temperature 163(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 'STOE IPDS 1' _diffrn_measurement_method '\phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16845 _diffrn_reflns_av_R_equivalents 0.1183 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.57 _diffrn_reflns_theta_max 26.90 _reflns_number_total 4304 _reflns_number_gt 3622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS 1 software package' _computing_cell_refinement 'STOE IPDS 1 software package' _computing_data_reduction 'STOE IPDS 1 software package' _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^)+(0.0997P)^2^+8.2187P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4304 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.2023 _refine_ls_wR_factor_gt 0.1942 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 Ga2 Ga 0.91483(7) 0.83239(7) 0.70043(5) 0.0206(2) Uani 1 1 d . . . Ga1 Ga 0.68948(7) 0.59833(7) 0.80534(5) 0.0203(2) Uani 1 1 d . . . O1 O 0.7571(5) 0.6472(4) 0.6192(3) 0.0237(9) Uani 1 1 d . . . O2 O 0.8708(5) 0.7679(5) 0.8890(4) 0.0235(9) Uani 1 1 d . . . N1 N 0.7592(6) 0.5369(5) 0.6734(4) 0.0191(10) Uani 1 1 d . . . N2 N 0.9936(6) 0.7830(5) 0.8482(4) 0.0202(10) Uani 1 1 d . . . C1 C 0.7089(8) 0.4584(7) 0.8894(6) 0.0305(14) Uani 1 1 d . . . H1B H 0.8093 0.4354 0.8966 0.037 Uiso 1 1 calc R . . C11 C 0.5721(11) 0.3141(8) 0.8345(8) 0.048(2) Uani 1 1 d . . . H11D H 0.5906 0.2534 0.8826 0.071 Uiso 1 1 calc R . . H11E H 0.5658 0.2624 0.7587 0.071 Uiso 1 1 calc R . . H11F H 0.4726 0.3346 0.8271 0.071 Uiso 1 1 calc R . . C12 C 0.7215(10) 0.5364(9) 1.0092(7) 0.0425(18) Uani 1 1 d . . . H12D H 0.7163 0.4667 1.0499 0.064 Uiso 1 1 calc R . . H12E H 0.6340 0.5769 1.0032 0.064 Uiso 1 1 calc R . . H12F H 0.8222 0.6154 1.0511 0.064 Uiso 1 1 calc R . . C2 C 0.5014(7) 0.6626(7) 0.7532(6) 0.0266(13) Uani 1 1 d . . . H1A H 0.5103 0.7060 0.6939 0.032 Uiso 1 1 calc R . . C21 C 0.3457(8) 0.5395(8) 0.6974(7) 0.0363(16) Uani 1 1 d . . . H12A H 0.2591 0.5774 0.6667 0.054 Uiso 1 1 calc R . . H12B H 0.3290 0.4981 0.7543 0.054 Uiso 1 1 calc R . . H12C H 0.3485 0.4635 0.6352 0.054 Uiso 1 1 calc R . . C22 C 0.5026(8) 0.7833(8) 0.8508(7) 0.0372(17) Uani 1 1 d . . . H11A H 0.4148 0.8207 0.8219 0.056 Uiso 1 1 calc R . . H11B H 0.6028 0.8626 0.8833 0.056 Uiso 1 1 calc R . . H11C H 0.4910 0.7443 0.9100 0.056 Uiso 1 1 calc R . . C3 C 0.6502(8) 0.4012(7) 0.5815(6) 0.0289(14) Uani 1 1 d . . . H3A H 0.6810 0.3870 0.5164 0.043 Uiso 1 1 calc R . . H3B H 0.5424 0.4071 0.5576 0.043 Uiso 1 1 calc R . . H3C H 0.6543 0.3187 0.6091 0.043 Uiso 1 1 calc R . . C4 C 0.9219(7) 0.5268(6) 0.7143(5) 0.0239(13) Uani 1 1 d . . . H4A H 0.9653 0.5339 0.6562 0.029 Uiso 1 1 calc R . . H4B H 0.9172 0.4301 0.7227 0.029 Uiso 1 1 calc R . . C5 C 1.0906(8) 0.8411(8) 0.6472(7) 0.0323(15) Uani 1 1 d . . . H5A H 1.1490 0.7764 0.6767 0.039 Uiso 1 1 calc R . . C51 C 1.2101(10) 0.9930(9) 0.6919(8) 0.0458(19) Uani 1 1 d . . . H51A H 1.2950 0.9883 0.6651 0.069 Uiso 1 1 calc R . . H51B H 1.2547 1.0290 0.7756 0.069 Uiso 1 1 calc R . . H51C H 1.1572 1.0594 0.6637 0.069 Uiso 1 1 calc R . . C52 C 1.0275(11) 0.7807(11) 0.5172(8) 0.053(2) Uani 1 1 d . . . H52A H 1.1161 0.7913 0.4934 0.079 Uiso 1 1 calc R . . H52B H 0.9594 0.8347 0.4848 0.079 Uiso 1 1 calc R . . H52C H 0.9663 0.6772 0.4898 0.079 Uiso 1 1 calc R . . C6 C 0.8043(8) 0.9791(7) 0.7200(6) 0.0292(14) Uani 1 1 d . . . H6A H 0.7507 0.9598 0.7714 0.035 Uiso 1 1 calc R . . C61 C 0.9127(10) 1.1364(7) 0.7765(7) 0.0403(18) Uani 1 1 d . . . H61A H 0.8501 1.2018 0.7870 0.060 Uiso 1 1 calc R . . H61B H 0.9663 1.1604 0.7279 0.060 Uiso 1 1 calc R . . H61C H 0.9916 1.1480 0.8509 0.060 Uiso 1 1 calc R . . C62 C 0.6765(11) 0.9604(9) 0.6082(8) 0.050(2) Uani 1 1 d . . . H62A H 0.6073 1.0171 0.6226 0.076 Uiso 1 1 calc R . . H62B H 0.6143 0.8571 0.5692 0.076 Uiso 1 1 calc R . . H62C H 0.7247 0.9950 0.5600 0.076 Uiso 1 1 calc R . . C7 C 1.1291(8) 0.8997(7) 0.9419(5) 0.0290(14) Uani 1 1 d . . . H7A H 1.1587 0.8707 1.0098 0.043 Uiso 1 1 calc R . . H7B H 1.1005 0.9893 0.9592 0.043 Uiso 1 1 calc R . . H7C H 1.2186 0.9171 0.9193 0.043 Uiso 1 1 calc R . . C8 C 1.0331(7) 0.6451(7) 0.8280(5) 0.0235(12) Uani 1 1 d . . . H8A H 1.0314 0.6074 0.8905 0.028 Uiso 1 1 calc R . . H8B H 1.1420 0.6662 0.8310 0.028 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 Ga2 0.0220(4) 0.0191(3) 0.0173(3) 0.0039(2) 0.0074(3) 0.0032(2) Ga1 0.0188(3) 0.0217(3) 0.0185(4) 0.0051(3) 0.0080(3) 0.0040(2) O1 0.028(2) 0.023(2) 0.0131(19) 0.0031(16) 0.0018(17) 0.0082(17) O2 0.019(2) 0.025(2) 0.022(2) 0.0034(17) 0.0098(17) 0.0023(16) N1 0.017(2) 0.017(2) 0.019(2) 0.0025(18) 0.0065(19) 0.0019(18) N2 0.016(2) 0.022(2) 0.018(2) 0.0059(19) 0.0050(19) 0.0026(18) C1 0.029(3) 0.030(3) 0.035(4) 0.013(3) 0.015(3) 0.008(3) C11 0.061(5) 0.033(4) 0.049(5) 0.016(4) 0.029(4) 0.004(4) C12 0.048(4) 0.053(5) 0.029(4) 0.023(3) 0.016(3) 0.010(4) C2 0.018(3) 0.033(3) 0.027(3) 0.007(3) 0.009(2) 0.006(2) C21 0.028(3) 0.033(3) 0.036(4) 0.001(3) 0.009(3) 0.003(3) C22 0.026(3) 0.036(4) 0.039(4) -0.002(3) 0.010(3) 0.010(3) C3 0.031(3) 0.018(3) 0.026(3) -0.002(2) 0.011(3) -0.004(2) C4 0.025(3) 0.020(3) 0.026(3) 0.004(2) 0.011(3) 0.010(2) C5 0.026(3) 0.033(3) 0.041(4) 0.015(3) 0.017(3) 0.007(3) C51 0.041(4) 0.049(5) 0.043(4) 0.015(4) 0.020(4) -0.001(3) C52 0.056(5) 0.062(5) 0.038(4) 0.007(4) 0.033(4) 0.002(4) C6 0.032(3) 0.023(3) 0.030(3) 0.006(3) 0.010(3) 0.009(3) C61 0.048(4) 0.025(3) 0.039(4) 0.006(3) 0.011(3) 0.008(3) C62 0.049(5) 0.041(4) 0.048(5) 0.017(4) 0.000(4) 0.017(4) C7 0.025(3) 0.030(3) 0.017(3) 0.001(2) 0.000(2) 0.003(3) C8 0.021(3) 0.027(3) 0.022(3) 0.007(2) 0.010(2) 0.005(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 Ga2 O1 1.900(4) . ? Ga2 C6 1.977(6) . ? Ga2 C5 1.995(7) . ? Ga2 N2 2.065(5) . ? Ga1 O2 1.910(4) . ? Ga1 C2 1.979(6) . ? Ga1 C1 1.986(7) . ? Ga1 N1 2.054(5) . ? O1 N1 1.453(6) . ? O2 N2 1.425(7) . ? N1 C3 1.468(7) . ? N1 C4 1.484(7) . ? N2 C7 1.468(7) . ? N2 C8 1.481(8) . ? C1 C12 1.531(11) . ? C1 C11 1.538(10) . ? C1 H1B 1.0000 . ? C11 H11D 0.9800 . ? C11 H11E 0.9800 . ? C11 H11F 0.9800 . ? C12 H12D 0.9800 . ? C12 H12E 0.9800 . ? C12 H12F 0.9800 . ? C2 C21 1.518(9) . ? C2 C22 1.524(9) . ? C2 H1A 1.0000 . ? C21 H12A 0.9800 . ? C21 H12B 0.9800 . ? C21 H12C 0.9800 . ? C22 H11A 0.9800 . ? C22 H11B 0.9800 . ? C22 H11C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C8 1.524(8) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C52 1.526(11) . ? C5 C51 1.526(10) . ? C5 H5A 1.0000 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C6 C62 1.507(10) . ? C6 C61 1.523(9) . ? C6 H6A 1.0000 . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 H61C 0.9800 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Ga2 C6 107.1(2) . . ? O1 Ga2 C5 109.7(2) . . ? C6 Ga2 C5 127.4(3) . . ? O1 Ga2 N2 92.71(19) . . ? C6 Ga2 N2 110.0(3) . . ? C5 Ga2 N2 104.6(3) . . ? O2 Ga1 C2 108.2(2) . . ? O2 Ga1 C1 107.8(2) . . ? C2 Ga1 C1 124.8(3) . . ? O2 Ga1 N1 93.08(19) . . ? C2 Ga1 N1 109.6(2) . . ? C1 Ga1 N1 108.7(2) . . ? N1 O1 Ga2 117.9(3) . . ? N2 O2 Ga1 117.4(3) . . ? O1 N1 C3 104.4(4) . . ? O1 N1 C4 108.3(4) . . ? C3 N1 C4 110.1(5) . . ? O1 N1 Ga1 107.8(3) . . ? C3 N1 Ga1 113.9(4) . . ? C4 N1 Ga1 111.8(4) . . ? O2 N2 C7 104.9(5) . . ? O2 N2 C8 108.7(4) . . ? C7 N2 C8 109.4(5) . . ? O2 N2 Ga2 108.1(3) . . ? C7 N2 Ga2 113.6(4) . . ? C8 N2 Ga2 111.9(4) . . ? C12 C1 C11 109.2(7) . . ? C12 C1 Ga1 107.0(5) . . ? C11 C1 Ga1 115.3(5) . . ? C12 C1 H1B 108.4 . . ? C11 C1 H1B 108.4 . . ? Ga1 C1 H1B 108.4 . . ? C1 C11 H11D 109.5 . . ? C1 C11 H11E 109.5 . . ? H11D C11 H11E 109.5 . . ? C1 C11 H11F 109.5 . . ? H11D C11 H11F 109.5 . . ? H11E C11 H11F 109.5 . . ? C1 C12 H12D 109.5 . . ? C1 C12 H12E 109.5 . . ? H12D C12 H12E 109.5 . . ? C1 C12 H12F 109.5 . . ? H12D C12 H12F 109.5 . . ? H12E C12 H12F 109.5 . . ? C21 C2 C22 111.3(6) . . ? C21 C2 Ga1 114.0(5) . . ? C22 C2 Ga1 110.4(4) . . ? C21 C2 H1A 106.9 . . ? C22 C2 H1A 106.9 . . ? Ga1 C2 H1A 106.9 . . ? C2 C21 H12A 109.5 . . ? C2 C21 H12B 109.5 . . ? H12A C21 H12B 109.5 . . ? C2 C21 H12C 109.5 . . ? H12A C21 H12C 109.5 . . ? H12B C21 H12C 109.5 . . ? C2 C22 H11A 109.5 . . ? C2 C22 H11B 109.5 . . ? H11A C22 H11B 109.5 . . ? C2 C22 H11C 109.5 . . ? H11A C22 H11C 109.5 . . ? H11B C22 H11C 109.5 . . ? N1 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C8 113.2(5) . . ? N1 C4 H4A 108.9 . . ? C8 C4 H4A 108.9 . . ? N1 C4 H4B 108.9 . . ? C8 C4 H4B 108.9 . . ? H4A C4 H4B 107.8 . . ? C52 C5 C51 109.8(7) . . ? C52 C5 Ga2 111.3(5) . . ? C51 C5 Ga2 114.0(5) . . ? C52 C5 H5A 107.1 . . ? C51 C5 H5A 107.1 . . ? Ga2 C5 H5A 107.1 . . ? C5 C51 H51A 109.5 . . ? C5 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C5 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C5 C52 H52A 109.5 . . ? C5 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C5 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C62 C6 C61 110.4(6) . . ? C62 C6 Ga2 111.1(5) . . ? C61 C6 Ga2 114.4(5) . . ? C62 C6 H6A 106.8 . . ? C61 C6 H6A 106.8 . . ? Ga2 C6 H6A 106.8 . . ? C6 C61 H61A 109.5 . . ? C6 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C6 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? C6 C62 H62A 109.5 . . ? C6 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C6 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? N2 C7 H7A 109.5 . . ? N2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 C4 114.3(5) . . ? N2 C8 H8A 108.7 . . ? C4 C8 H8A 108.7 . . ? N2 C8 H8B 108.7 . . ? C4 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? 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 C6 Ga2 O1 N1 -120.7(4) . . . . ? C5 Ga2 O1 N1 97.7(4) . . . . ? N2 Ga2 O1 N1 -8.8(4) . . . . ? C2 Ga1 O2 N2 -120.9(4) . . . . ? C1 Ga1 O2 N2 101.7(4) . . . . ? N1 Ga1 O2 N2 -9.1(4) . . . . ? Ga2 O1 N1 C3 -167.4(4) . . . . ? Ga2 O1 N1 C4 -50.1(5) . . . . ? Ga2 O1 N1 Ga1 71.1(4) . . . . ? O2 Ga1 N1 O1 -65.2(3) . . . . ? C2 Ga1 N1 O1 45.3(4) . . . . ? C1 Ga1 N1 O1 -175.2(3) . . . . ? O2 Ga1 N1 C3 179.4(4) . . . . ? C2 Ga1 N1 C3 -70.0(5) . . . . ? C1 Ga1 N1 C3 69.4(5) . . . . ? O2 Ga1 N1 C4 53.8(4) . . . . ? C2 Ga1 N1 C4 164.4(4) . . . . ? C1 Ga1 N1 C4 -56.2(4) . . . . ? Ga1 O2 N2 C7 -166.5(4) . . . . ? Ga1 O2 N2 C8 -49.6(5) . . . . ? Ga1 O2 N2 Ga2 72.0(4) . . . . ? O1 Ga2 N2 O2 -66.1(3) . . . . ? C6 Ga2 N2 O2 43.2(4) . . . . ? C5 Ga2 N2 O2 -177.3(3) . . . . ? O1 Ga2 N2 C7 177.9(4) . . . . ? C6 Ga2 N2 C7 -72.8(5) . . . . ? C5 Ga2 N2 C7 66.8(5) . . . . ? O1 Ga2 N2 C8 53.5(4) . . . . ? C6 Ga2 N2 C8 162.8(4) . . . . ? C5 Ga2 N2 C8 -57.6(4) . . . . ? O2 Ga1 C1 C12 58.1(5) . . . . ? C2 Ga1 C1 C12 -70.4(6) . . . . ? N1 Ga1 C1 C12 157.8(5) . . . . ? O2 Ga1 C1 C11 179.8(5) . . . . ? C2 Ga1 C1 C11 51.3(7) . . . . ? N1 Ga1 C1 C11 -80.5(6) . . . . ? O2 Ga1 C2 C21 -173.1(5) . . . . ? C1 Ga1 C2 C21 -44.7(6) . . . . ? N1 Ga1 C2 C21 86.7(6) . . . . ? O2 Ga1 C2 C22 -46.9(6) . . . . ? C1 Ga1 C2 C22 81.5(6) . . . . ? N1 Ga1 C2 C22 -147.1(5) . . . . ? O1 N1 C4 C8 81.0(6) . . . . ? C3 N1 C4 C8 -165.4(5) . . . . ? Ga1 N1 C4 C8 -37.7(6) . . . . ? O1 Ga2 C5 C52 45.3(6) . . . . ? C6 Ga2 C5 C52 -86.5(7) . . . . ? N2 Ga2 C5 C52 143.6(6) . . . . ? O1 Ga2 C5 C51 170.2(5) . . . . ? C6 Ga2 C5 C51 38.4(7) . . . . ? N2 Ga2 C5 C51 -91.5(6) . . . . ? O1 Ga2 C6 C62 -50.0(6) . . . . ? C5 Ga2 C6 C62 82.7(7) . . . . ? N2 Ga2 C6 C62 -149.5(6) . . . . ? O1 Ga2 C6 C61 -175.9(5) . . . . ? C5 Ga2 C6 C61 -43.2(7) . . . . ? N2 Ga2 C6 C61 84.7(6) . . . . ? O2 N2 C8 C4 81.5(6) . . . . ? C7 N2 C8 C4 -164.5(5) . . . . ? Ga2 N2 C8 C4 -37.7(6) . . . . ? N1 C4 C8 N2 -29.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.925 _diffrn_reflns_theta_full 26.90 _diffrn_measured_fraction_theta_full 0.925 _refine_diff_density_max 2.651 _refine_diff_density_min -1.389 _refine_diff_density_rms 0.177 # Attachment 'Compound_4b.cif' data_paul _database_code_depnum_ccdc_archive 'CCDC 668796' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-Di-tert-butyl-2,2,5,5-tetrakis-isopropyl-2,5-digalla -3,6-dioxa-1,4-diazabicyclo[2,2,2]octan ; _chemical_name_common ; N,N'-Bis-oxo-N,N'-di-tert-butylethylenediamine tetrakis-isopropyl-digallate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H50 Ga2 N2 O2' _chemical_formula_weight 514.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.421(3) _cell_length_b 9.5007(11) _cell_length_c 14.505(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.257(16) _cell_angle_gamma 90.00 _cell_volume 2687.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 1454 _cell_measurement_theta_min 4.42 _cell_measurement_theta_max 27.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 2.022 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.153 _exptl_absorpt_correction_T_max 0.5447 _exptl_absorpt_process_details ; Absorption correction was done with the program ABSCOR from the IPDS-1 software package. ABSCOR works similar to the well known DIFABS, but reads and provides Fo^2^ values instead of Fo ones. ; _exptl_special_details ; ; _diffrn_ambient_temperature 163(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 'STOE IPDS-1' _diffrn_measurement_method '\phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30043 _diffrn_reflns_av_R_equivalents 0.1332 _diffrn_reflns_av_sigmaI/netI 0.0731 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.42 _diffrn_reflns_theta_max 27.03 _reflns_number_total 5780 _reflns_number_gt 4608 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS-1 software package' _computing_cell_refinement 'STOE IPDS-1 software package' _computing_data_reduction 'STOE IPDS-1 software package' _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^)+(0.1164P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5780 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1658 _refine_ls_wR_factor_gt 0.1555 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga1 Ga 0.34009(2) 0.06963(5) 0.17083(3) 0.01476(16) Uani 1 1 d . . . O1 O 0.22953(13) 0.2272(3) 0.1829(2) 0.0152(6) Uani 1 1 d . . . N1 N 0.28218(15) 0.2559(4) 0.1383(3) 0.0133(7) Uani 1 1 d . . . C1 C 0.4107(3) 0.0521(7) 0.1004(5) 0.0458(16) Uani 1 1 d . . . H1A H 0.3913 0.0971 0.0356 0.055 Uiso 1 1 calc R . . C11 C 0.4785(4) 0.1115(10) 0.1435(8) 0.085(3) Uani 1 1 d . . . H11A H 0.5053 0.1040 0.0978 0.127 Uiso 1 1 calc R . . H11B H 0.5017 0.0597 0.2026 0.127 Uiso 1 1 calc R . . H11C H 0.4741 0.2107 0.1591 0.127 Uiso 1 1 calc R . . C12 C 0.4190(5) -0.1041(11) 0.0837(11) 0.123(5) Uani 1 1 d . . . H12A H 0.4418 -0.1164 0.0336 0.185 Uiso 1 1 calc R . . H12B H 0.3737 -0.1489 0.0629 0.185 Uiso 1 1 calc R . . H12C H 0.4467 -0.1478 0.1438 0.185 Uiso 1 1 calc R . . C2 C 0.3624(2) 0.0134(5) 0.3091(3) 0.0249(10) Uani 1 1 d . . . H2A H 0.3325 0.0706 0.3382 0.030 Uiso 1 1 calc R . . C21 C 0.3441(3) -0.1409(6) 0.3175(4) 0.0390(14) Uani 1 1 d . . . H21A H 0.3511 -0.1644 0.3856 0.058 Uiso 1 1 calc R . . H21B H 0.3735 -0.2007 0.2915 0.058 Uiso 1 1 calc R . . H21C H 0.2960 -0.1567 0.2809 0.058 Uiso 1 1 calc R . . C22 C 0.4361(3) 0.0390(8) 0.3698(4) 0.0472(16) Uani 1 1 d . . . H22A H 0.4409 0.0172 0.4375 0.071 Uiso 1 1 calc R . . H22B H 0.4481 0.1379 0.3641 0.071 Uiso 1 1 calc R . . H22C H 0.4669 -0.0215 0.3468 0.071 Uiso 1 1 calc R . . C3 C 0.3133(2) 0.3963(5) 0.1796(4) 0.0257(10) Uani 1 1 d . . . C31 C 0.3405(3) 0.3813(6) 0.2879(4) 0.0372(13) Uani 1 1 d . . . H31A H 0.3038 0.3479 0.3132 0.056 Uiso 1 1 calc R . . H31B H 0.3570 0.4729 0.3167 0.056 Uiso 1 1 calc R . . H31C H 0.3784 0.3136 0.3043 0.056 Uiso 1 1 calc R . . C32 C 0.2604(3) 0.5122(6) 0.1532(5) 0.0522(18) Uani 1 1 d . . . H32A H 0.2188 0.4823 0.1684 0.078 Uiso 1 1 calc R . . H32B H 0.2492 0.5323 0.0840 0.078 Uiso 1 1 calc R . . H32C H 0.2787 0.5973 0.1900 0.078 Uiso 1 1 calc R . . C33 C 0.3722(4) 0.4305(8) 0.1391(6) 0.060(2) Uani 1 1 d . . . H33A H 0.4048 0.3520 0.1520 0.090 Uiso 1 1 calc R . . H33B H 0.3955 0.5160 0.1699 0.090 Uiso 1 1 calc R . . H33C H 0.3542 0.4456 0.0693 0.090 Uiso 1 1 calc R . . C4 C 0.2485(2) 0.2659(5) 0.0323(3) 0.0173(9) Uani 1 1 d . . . H4A H 0.2786 0.3209 0.0033 0.021 Uiso 1 1 calc R . . H4B H 0.2051 0.3189 0.0212 0.021 Uiso 1 1 calc R . . Ga2 Ga 0.153629(19) 0.10856(4) 0.12321(3) 0.00829(15) Uani 1 1 d . . . O2 O 0.26213(13) -0.0416(3) 0.1050(2) 0.0134(6) Uani 1 1 d . . . N2 N 0.20468(15) 0.0188(3) 0.0326(2) 0.0094(6) Uani 1 1 d . . . C5 C 0.06924(19) 0.2213(5) 0.0602(3) 0.0172(9) Uani 1 1 d . . . H5A H 0.0307 0.1521 0.0396 0.021 Uiso 1 1 calc R . . C51 C 0.0645(2) 0.3133(5) -0.0275(4) 0.0249(10) Uani 1 1 d . . . H51A H 0.0179 0.3507 -0.0527 0.037 Uiso 1 1 calc R . . H51B H 0.0756 0.2570 -0.0775 0.037 Uiso 1 1 calc R . . H51C H 0.0971 0.3915 -0.0088 0.037 Uiso 1 1 calc R . . C52 C 0.0548(3) 0.3107(6) 0.1404(4) 0.0323(12) Uani 1 1 d . . . H52A H 0.0123 0.3640 0.1137 0.049 Uiso 1 1 calc R . . H52B H 0.0929 0.3761 0.1664 0.049 Uiso 1 1 calc R . . H52C H 0.0500 0.2489 0.1921 0.049 Uiso 1 1 calc R . . C6 C 0.14718(19) -0.0216(5) 0.2284(3) 0.0146(8) Uani 1 1 d . . . H6A H 0.1767 -0.1052 0.2276 0.017 Uiso 1 1 calc R . . C61 C 0.0750(2) -0.0748(5) 0.2175(4) 0.0263(11) Uani 1 1 d . . . H61A H 0.0760 -0.1404 0.2701 0.039 Uiso 1 1 calc R . . H61B H 0.0573 -0.1233 0.1554 0.039 Uiso 1 1 calc R . . H61C H 0.0451 0.0049 0.2200 0.039 Uiso 1 1 calc R . . C62 C 0.1759(2) 0.0514(5) 0.3261(3) 0.0222(9) Uani 1 1 d . . . H62A H 0.1719 -0.0117 0.3777 0.033 Uiso 1 1 calc R . . H62B H 0.1500 0.1379 0.3272 0.033 Uiso 1 1 calc R . . H62C H 0.2243 0.0747 0.3362 0.033 Uiso 1 1 calc R . . C7 C 0.1697(2) -0.1000(4) -0.0348(3) 0.0170(9) Uani 1 1 d . . . C71 C 0.1470(2) -0.2092(5) 0.0255(3) 0.0230(9) Uani 1 1 d . . . H71A H 0.1093 -0.1712 0.0468 0.035 Uiso 1 1 calc R . . H71B H 0.1856 -0.2331 0.0820 0.035 Uiso 1 1 calc R . . H71C H 0.1315 -0.2940 -0.0133 0.035 Uiso 1 1 calc R . . C72 C 0.1061(2) -0.0427(6) -0.1084(4) 0.0294(11) Uani 1 1 d . . . H72A H 0.0767 0.0031 -0.0750 0.044 Uiso 1 1 calc R . . H72B H 0.0810 -0.1201 -0.1482 0.044 Uiso 1 1 calc R . . H72C H 0.1196 0.0261 -0.1498 0.044 Uiso 1 1 calc R . . C73 C 0.2183(3) -0.1676(6) -0.0840(4) 0.0348(12) Uani 1 1 d . . . H73A H 0.2319 -0.0975 -0.1244 0.052 Uiso 1 1 calc R . . H73B H 0.1951 -0.2462 -0.1243 0.052 Uiso 1 1 calc R . . H73C H 0.2592 -0.2024 -0.0348 0.052 Uiso 1 1 calc R . . C8 C 0.2329(2) 0.1264(5) -0.0195(3) 0.0157(8) Uani 1 1 d . . . H8A H 0.1995 0.1421 -0.0838 0.019 Uiso 1 1 calc R . . H8B H 0.2755 0.0892 -0.0297 0.019 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 0.0104(2) 0.0138(3) 0.0188(3) 0.00383(18) 0.00236(18) 0.00168(15) O1 0.0141(12) 0.0147(16) 0.0185(15) -0.0064(12) 0.0078(11) -0.0034(11) N1 0.0109(14) 0.0063(17) 0.0212(18) 0.0027(14) 0.0022(13) -0.0029(12) C1 0.025(2) 0.061(4) 0.059(4) 0.016(3) 0.025(3) 0.009(3) C11 0.043(4) 0.085(7) 0.134(9) 0.012(6) 0.038(5) -0.005(4) C12 0.082(6) 0.096(8) 0.234(15) -0.063(8) 0.111(9) 0.001(5) C2 0.0175(19) 0.028(3) 0.024(2) 0.007(2) -0.0019(17) 0.0012(17) C21 0.031(3) 0.040(3) 0.038(3) 0.024(3) -0.002(2) -0.001(2) C22 0.032(3) 0.058(4) 0.035(3) 0.012(3) -0.014(2) 0.001(3) C3 0.026(2) 0.014(2) 0.035(3) -0.004(2) 0.005(2) -0.0093(17) C31 0.039(3) 0.025(3) 0.037(3) -0.011(2) -0.004(2) -0.016(2) C32 0.053(3) 0.007(3) 0.077(5) -0.005(3) -0.010(3) 0.002(2) C33 0.056(4) 0.052(4) 0.080(5) -0.016(4) 0.033(4) -0.041(3) C4 0.0166(18) 0.013(2) 0.021(2) 0.0090(17) 0.0035(16) 0.0004(15) Ga2 0.0114(2) 0.0048(2) 0.0088(2) 0.00016(15) 0.00313(16) 0.00061(14) O2 0.0145(12) 0.0090(15) 0.0137(14) 0.0043(11) -0.0002(10) 0.0065(10) N2 0.0132(14) 0.0064(16) 0.0066(15) 0.0020(12) 0.0001(12) 0.0037(12) C5 0.0132(17) 0.016(2) 0.024(2) 0.0050(18) 0.0076(16) 0.0045(15) C51 0.025(2) 0.017(2) 0.030(3) 0.012(2) 0.0041(18) 0.0083(17) C52 0.034(2) 0.031(3) 0.039(3) 0.002(2) 0.021(2) 0.016(2) C6 0.0184(18) 0.012(2) 0.0124(19) 0.0048(16) 0.0037(15) 0.0004(15) C61 0.028(2) 0.028(3) 0.027(3) 0.006(2) 0.015(2) -0.0100(19) C62 0.036(2) 0.021(3) 0.013(2) -0.0006(18) 0.0124(18) 0.0008(19) C7 0.022(2) 0.013(2) 0.014(2) -0.0067(16) 0.0013(16) 0.0024(15) C71 0.032(2) 0.012(2) 0.021(2) -0.0041(18) 0.0021(18) -0.0023(17) C72 0.030(2) 0.025(3) 0.026(3) -0.001(2) -0.0041(19) -0.0003(19) C73 0.049(3) 0.030(3) 0.031(3) -0.022(2) 0.020(2) 0.000(2) C8 0.0226(19) 0.015(2) 0.0102(19) 0.0049(16) 0.0056(15) 0.0018(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 O2 1.913(3) . ? Ga1 C2 1.994(5) . ? Ga1 C1 2.007(5) . ? Ga1 N1 2.102(3) . ? O1 N1 1.436(4) . ? O1 Ga2 1.904(3) . ? N1 C4 1.489(5) . ? N1 C3 1.522(5) . ? C1 C11 1.453(10) . ? C1 C12 1.521(12) . ? C1 H1A 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C2 C22 1.521(6) . ? C2 C21 1.527(8) . ? C2 H2A 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C3 C31 1.511(8) . ? C3 C32 1.511(7) . ? C3 C33 1.522(7) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C4 C8 1.511(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? Ga2 C6 1.999(4) . ? Ga2 C5 2.004(4) . ? Ga2 N2 2.087(3) . ? O2 N2 1.441(4) . ? N2 C8 1.485(5) . ? N2 C7 1.525(5) . ? C5 C51 1.523(6) . ? C5 C52 1.537(6) . ? C5 H5A 1.0000 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C6 C61 1.522(6) . ? C6 C62 1.530(6) . ? C6 H6A 1.0000 . ? C61 H61A 0.9800 . ? C61 H61B 0.9800 . ? C61 H61C 0.9800 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C7 C71 1.515(6) . ? C7 C72 1.517(6) . ? C7 C73 1.526(6) . ? C71 H71A 0.9800 . ? C71 H71B 0.9800 . ? C71 H71C 0.9800 . ? C72 H72A 0.9800 . ? C72 H72B 0.9800 . ? C72 H72C 0.9800 . ? C73 H73A 0.9800 . ? C73 H73B 0.9800 . ? C73 H73C 0.9800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 O2 Ga1 C2 105.22(16) . . ? O2 Ga1 C1 108.5(2) . . ? C2 Ga1 C1 120.4(2) . . ? O2 Ga1 N1 91.34(12) . . ? C2 Ga1 N1 113.41(18) . . ? C1 Ga1 N1 113.4(2) . . ? N1 O1 Ga2 121.6(2) . . ? O1 N1 C4 107.4(3) . . ? O1 N1 C3 105.7(3) . . ? C4 N1 C3 111.2(3) . . ? O1 N1 Ga1 100.7(2) . . ? C4 N1 Ga1 110.0(3) . . ? C3 N1 Ga1 120.5(3) . . ? C11 C1 C12 108.1(6) . . ? C11 C1 Ga1 119.0(6) . . ? C12 C1 Ga1 107.0(5) . . ? C11 C1 H1A 107.4 . . ? C12 C1 H1A 107.4 . . ? Ga1 C1 H1A 107.4 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C22 C2 C21 109.3(4) . . ? C22 C2 Ga1 115.5(4) . . ? C21 C2 Ga1 110.4(3) . . ? C22 C2 H2A 107.0 . . ? C21 C2 H2A 107.0 . . ? Ga1 C2 H2A 107.0 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22A 109.5 . . ? C2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C31 C3 C32 110.3(5) . . ? C31 C3 C33 109.4(5) . . ? C32 C3 C33 109.5(5) . . ? C31 C3 N1 108.0(4) . . ? C32 C3 N1 110.8(4) . . ? C33 C3 N1 108.7(4) . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 H32A 109.5 . . ? C3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C3 C33 H33A 109.5 . . ? C3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N1 C4 C8 115.0(3) . . ? N1 C4 H4A 108.5 . . ? C8 C4 H4A 108.5 . . ? N1 C4 H4B 108.5 . . ? C8 C4 H4B 108.5 . . ? H4A C4 H4B 107.5 . . ? O1 Ga2 C6 104.36(14) . . ? O1 Ga2 C5 111.41(16) . . ? C6 Ga2 C5 115.86(16) . . ? O1 Ga2 N2 92.11(12) . . ? C6 Ga2 N2 112.74(15) . . ? C5 Ga2 N2 116.99(15) . . ? N2 O2 Ga1 121.4(2) . . ? O2 N2 C8 106.9(3) . . ? O2 N2 C7 107.3(3) . . ? C8 N2 C7 111.2(3) . . ? O2 N2 Ga2 98.89(19) . . ? C8 N2 Ga2 112.4(2) . . ? C7 N2 Ga2 118.7(2) . . ? C51 C5 C52 109.6(4) . . ? C51 C5 Ga2 121.4(3) . . ? C52 C5 Ga2 106.4(3) . . ? C51 C5 H5A 106.2 . . ? C52 C5 H5A 106.2 . . ? Ga2 C5 H5A 106.2 . . ? C5 C51 H51A 109.5 . . ? C5 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C5 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C5 C52 H52A 109.5 . . ? C5 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C5 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C61 C6 C62 109.9(4) . . ? C61 C6 Ga2 114.0(3) . . ? C62 C6 Ga2 109.5(3) . . ? C61 C6 H6A 107.7 . . ? C62 C6 H6A 107.7 . . ? Ga2 C6 H6A 107.7 . . ? C6 C61 H61A 109.5 . . ? C6 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C6 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? C6 C62 H62A 109.5 . . ? C6 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C6 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C71 C7 C72 107.9(4) . . ? C71 C7 N2 107.6(3) . . ? C72 C7 N2 109.0(3) . . ? C71 C7 C73 109.6(4) . . ? C72 C7 C73 111.2(4) . . ? N2 C7 C73 111.4(3) . . ? C7 C71 H71A 109.5 . . ? C7 C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? C7 C71 H71C 109.5 . . ? H71A C71 H71C 109.5 . . ? H71B C71 H71C 109.5 . . ? C7 C72 H72A 109.5 . . ? C7 C72 H72B 109.5 . . ? H72A C72 H72B 109.5 . . ? C7 C72 H72C 109.5 . . ? H72A C72 H72C 109.5 . . ? H72B C72 H72C 109.5 . . ? C7 C73 H73A 109.5 . . ? C7 C73 H73B 109.5 . . ? H73A C73 H73B 109.5 . . ? C7 C73 H73C 109.5 . . ? H73A C73 H73C 109.5 . . ? H73B C73 H73C 109.5 . . ? N2 C8 C4 114.0(3) . . ? N2 C8 H8A 108.7 . . ? C4 C8 H8A 108.7 . . ? N2 C8 H8B 108.7 . . ? C4 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? 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 Ga2 O1 N1 C4 36.5(4) . . . . ? Ga2 O1 N1 C3 155.3(3) . . . . ? Ga2 O1 N1 Ga1 -78.6(2) . . . . ? O2 Ga1 N1 O1 58.9(2) . . . . ? C2 Ga1 N1 O1 -48.3(3) . . . . ? C1 Ga1 N1 O1 169.7(3) . . . . ? O2 Ga1 N1 C4 -54.2(2) . . . . ? C2 Ga1 N1 C4 -161.5(2) . . . . ? C1 Ga1 N1 C4 56.6(3) . . . . ? O2 Ga1 N1 C3 174.4(3) . . . . ? C2 Ga1 N1 C3 67.1(3) . . . . ? C1 Ga1 N1 C3 -74.8(4) . . . . ? O2 Ga1 C1 C11 -171.7(6) . . . . ? C2 Ga1 C1 C11 -50.6(7) . . . . ? N1 Ga1 C1 C11 88.4(6) . . . . ? O2 Ga1 C1 C12 -48.9(7) . . . . ? C2 Ga1 C1 C12 72.2(7) . . . . ? N1 Ga1 C1 C12 -148.8(7) . . . . ? O2 Ga1 C2 C22 156.4(4) . . . . ? C1 Ga1 C2 C22 33.7(5) . . . . ? N1 Ga1 C2 C22 -105.3(4) . . . . ? O2 Ga1 C2 C21 31.7(3) . . . . ? C1 Ga1 C2 C21 -91.0(4) . . . . ? N1 Ga1 C2 C21 130.0(3) . . . . ? O1 N1 C3 C31 58.6(4) . . . . ? C4 N1 C3 C31 174.8(4) . . . . ? Ga1 N1 C3 C31 -54.3(5) . . . . ? O1 N1 C3 C32 -62.3(5) . . . . ? C4 N1 C3 C32 53.9(5) . . . . ? Ga1 N1 C3 C32 -175.2(4) . . . . ? O1 N1 C3 C33 177.3(5) . . . . ? C4 N1 C3 C33 -66.5(5) . . . . ? Ga1 N1 C3 C33 64.4(5) . . . . ? O1 N1 C4 C8 -80.4(4) . . . . ? C3 N1 C4 C8 164.5(3) . . . . ? Ga1 N1 C4 C8 28.4(4) . . . . ? N1 O1 Ga2 C6 132.7(3) . . . . ? N1 O1 Ga2 C5 -101.6(3) . . . . ? N1 O1 Ga2 N2 18.6(3) . . . . ? C2 Ga1 O2 N2 136.4(3) . . . . ? C1 Ga1 O2 N2 -93.5(3) . . . . ? N1 Ga1 O2 N2 21.7(2) . . . . ? Ga1 O2 N2 C8 35.2(3) . . . . ? Ga1 O2 N2 C7 154.5(2) . . . . ? Ga1 O2 N2 Ga2 -81.6(2) . . . . ? O1 Ga2 N2 O2 61.0(2) . . . . ? C6 Ga2 N2 O2 -45.5(2) . . . . ? C5 Ga2 N2 O2 176.4(2) . . . . ? O1 Ga2 N2 C8 -51.4(3) . . . . ? C6 Ga2 N2 C8 -158.0(2) . . . . ? C5 Ga2 N2 C8 63.9(3) . . . . ? O1 Ga2 N2 C7 176.4(3) . . . . ? C6 Ga2 N2 C7 69.9(3) . . . . ? C5 Ga2 N2 C7 -68.2(3) . . . . ? O1 Ga2 C5 C51 67.2(4) . . . . ? C6 Ga2 C5 C51 -173.7(3) . . . . ? N2 Ga2 C5 C51 -36.9(4) . . . . ? O1 Ga2 C5 C52 -58.9(3) . . . . ? C6 Ga2 C5 C52 60.1(3) . . . . ? N2 Ga2 C5 C52 -163.1(3) . . . . ? O1 Ga2 C6 C61 151.3(3) . . . . ? C5 Ga2 C6 C61 28.4(4) . . . . ? N2 Ga2 C6 C61 -110.2(3) . . . . ? O1 Ga2 C6 C62 27.7(3) . . . . ? C5 Ga2 C6 C62 -95.2(3) . . . . ? N2 Ga2 C6 C62 126.2(3) . . . . ? O2 N2 C7 C71 59.6(4) . . . . ? C8 N2 C7 C71 176.1(3) . . . . ? Ga2 N2 C7 C71 -51.2(4) . . . . ? O2 N2 C7 C72 176.4(3) . . . . ? C8 N2 C7 C72 -67.0(4) . . . . ? Ga2 N2 C7 C72 65.6(4) . . . . ? O2 N2 C7 C73 -60.5(4) . . . . ? C8 N2 C7 C73 56.0(5) . . . . ? Ga2 N2 C7 C73 -171.3(3) . . . . ? O2 N2 C8 C4 -80.9(4) . . . . ? C7 N2 C8 C4 162.3(3) . . . . ? Ga2 N2 C8 C4 26.5(4) . . . . ? N1 C4 C8 N2 42.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.03 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 2.177 _refine_diff_density_min -1.131 _refine_diff_density_rms 0.173 # Attachment 'Compound_5.cif' data_sad _database_code_depnum_ccdc_archive 'CCDC 668797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H58 Ga2 N4 O4' _chemical_formula_weight 606.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2833(15) _cell_length_b 11.7371(19) _cell_length_c 15.234(3) _cell_angle_alpha 82.631(3) _cell_angle_beta 89.375(3) _cell_angle_gamma 73.776(3) _cell_volume 1580.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 1.737 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5897 _exptl_absorpt_correction_T_max 0.8187 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.722770 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18329 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0570 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 30.04 _reflns_number_total 9100 _reflns_number_gt 7017 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT (Bruker AXS, 2000)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _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^)+(0.0333P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9100 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0803 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 0.986 _refine_ls_restrained_S_all 0.986 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ga1 Ga 0.71941(2) -0.069030(18) 0.223816(13) 0.01649(6) Uani 1 1 d . . . Ga2 Ga 0.79275(2) 0.289320(18) 0.318349(13) 0.01615(6) Uani 1 1 d . . . N1 N 0.58258(18) 0.12230(14) 0.08267(11) 0.0192(3) Uani 1 1 d . . . H1N H 0.607(3) 0.160(2) 0.1232(15) 0.038(7) Uiso 1 1 d . . . N2 N 0.36817(17) 0.37445(14) 0.10254(11) 0.0209(3) Uani 1 1 d . . . N3 N 0.74257(17) 0.12213(14) 0.33313(10) 0.0172(3) Uani 1 1 d . . . N4 N 0.49455(17) 0.35050(14) 0.34535(10) 0.0205(3) Uani 1 1 d . . . O1 O 0.61510(15) -0.00128(11) 0.11027(9) 0.0236(3) Uani 1 1 d . . . O2 O 0.52864(15) 0.35920(13) 0.11027(9) 0.0230(3) Uani 1 1 d . . . H2O H 0.534(3) 0.369(2) 0.1627(17) 0.045(8) Uiso 1 1 d . . . O3 O 0.72373(14) 0.08816(11) 0.24776(8) 0.0185(3) Uani 1 1 d . . . O4 O 0.59697(14) 0.36793(12) 0.27510(8) 0.0192(3) Uani 1 1 d . . . C1 C 0.9250(2) -0.16567(17) 0.19130(13) 0.0218(4) Uani 1 1 d . . . C2 C 1.0293(2) -0.0877(2) 0.16532(16) 0.0322(5) Uani 1 1 d . . . H2A H 1.0415 -0.0455 0.2150 0.048 Uiso 1 1 calc R . . H2B H 0.9860 -0.0293 0.1139 0.048 Uiso 1 1 calc R . . H2C H 1.1273 -0.1383 0.1504 0.048 Uiso 1 1 calc R . . C3 C 0.9986(2) -0.2602(2) 0.26831(14) 0.0332(5) Uani 1 1 d . . . H3A H 1.0955 -0.3088 0.2502 0.050 Uiso 1 1 calc R . . H3B H 0.9333 -0.3117 0.2853 0.050 Uiso 1 1 calc R . . H3C H 1.0140 -0.2206 0.3189 0.050 Uiso 1 1 calc R . . C4 C 0.9083(2) -0.2291(2) 0.11206(14) 0.0317(5) Uani 1 1 d . . . H4A H 1.0075 -0.2758 0.0955 0.048 Uiso 1 1 calc R . . H4B H 0.8614 -0.1696 0.0620 0.048 Uiso 1 1 calc R . . H4C H 0.8453 -0.2828 0.1279 0.048 Uiso 1 1 calc R . . C5 C 0.5753(2) -0.14964(17) 0.28831(13) 0.0229(4) Uani 1 1 d . . . C6 C 0.6215(2) -0.19900(19) 0.38506(14) 0.0293(5) Uani 1 1 d . . . H6A H 0.6127 -0.1324 0.4194 0.044 Uiso 1 1 calc R . . H6B H 0.7256 -0.2493 0.3882 0.044 Uiso 1 1 calc R . . H6C H 0.5557 -0.2469 0.4094 0.044 Uiso 1 1 calc R . . C7 C 0.5770(3) -0.25528(19) 0.23804(15) 0.0335(5) Uani 1 1 d . . . H7A H 0.5025 -0.2946 0.2628 0.050 Uiso 1 1 calc R . . H7B H 0.6769 -0.3128 0.2440 0.050 Uiso 1 1 calc R . . H7C H 0.5525 -0.2259 0.1753 0.050 Uiso 1 1 calc R . . C8 C 0.4141(2) -0.0679(2) 0.28365(16) 0.0319(5) Uani 1 1 d . . . H8A H 0.3820 -0.0410 0.2215 0.048 Uiso 1 1 calc R . . H8B H 0.4098 0.0017 0.3139 0.048 Uiso 1 1 calc R . . H8C H 0.3474 -0.1120 0.3125 0.048 Uiso 1 1 calc R . . C9 C 0.6701(2) 0.14120(19) 0.00330(13) 0.0275(5) Uani 1 1 d . . . H9A H 0.7770 0.1030 0.0168 0.041 Uiso 1 1 calc R . . H9B H 0.6539 0.2272 -0.0144 0.041 Uiso 1 1 calc R . . H9C H 0.6376 0.1060 -0.0451 0.041 Uiso 1 1 calc R . . C10 C 0.4166(2) 0.16806(17) 0.06604(14) 0.0233(4) Uani 1 1 d . . . H10A H 0.3662 0.1495 0.1215 0.028 Uiso 1 1 calc R . . H10B H 0.3882 0.1237 0.0211 0.028 Uiso 1 1 calc R . . C11 C 0.3566(2) 0.30071(17) 0.03482(13) 0.0242(4) Uani 1 1 d . . . H11A H 0.4130 0.3217 -0.0174 0.029 Uiso 1 1 calc R . . H11B H 0.2500 0.3186 0.0160 0.029 Uiso 1 1 calc R . . C12 C 0.3001(2) 0.50099(18) 0.06979(14) 0.0288(5) Uani 1 1 d . . . H12A H 0.3468 0.5221 0.0144 0.043 Uiso 1 1 calc R . . H12B H 0.3157 0.5505 0.1139 0.043 Uiso 1 1 calc R . . H12C H 0.1922 0.5150 0.0592 0.043 Uiso 1 1 calc R . . C13 C 0.9376(2) 0.29937(18) 0.22104(14) 0.0238(4) Uani 1 1 d . . . C14 C 0.8920(2) 0.2681(2) 0.13358(13) 0.0308(5) Uani 1 1 d . . . H14A H 0.9659 0.2777 0.0889 0.046 Uiso 1 1 calc R . . H14B H 0.7931 0.3216 0.1140 0.046 Uiso 1 1 calc R . . H14C H 0.8874 0.1850 0.1414 0.046 Uiso 1 1 calc R . . C15 C 1.0953(2) 0.2179(2) 0.24711(16) 0.0372(6) Uani 1 1 d . . . H15A H 1.1659 0.2327 0.2017 0.056 Uiso 1 1 calc R . . H15B H 1.0944 0.1340 0.2521 0.056 Uiso 1 1 calc R . . H15C H 1.1265 0.2349 0.3041 0.056 Uiso 1 1 calc R . . C16 C 0.9450(3) 0.4291(2) 0.20645(18) 0.0480(7) Uani 1 1 d . . . H16A H 0.9803 0.4494 0.2612 0.072 Uiso 1 1 calc R . . H16B H 0.8448 0.4826 0.1899 0.072 Uiso 1 1 calc R . . H16C H 1.0144 0.4384 0.1589 0.072 Uiso 1 1 calc R . . C17 C 0.8285(2) 0.33676(18) 0.43769(13) 0.0243(4) Uani 1 1 d . . . C18 C 0.9959(3) 0.3074(2) 0.46072(15) 0.0398(6) Uani 1 1 d . . . H18A H 1.0090 0.3356 0.5171 0.060 Uiso 1 1 calc R . . H18B H 1.0451 0.3472 0.4140 0.060 Uiso 1 1 calc R . . H18C H 1.0410 0.2207 0.4658 0.060 Uiso 1 1 calc R . . C19 C 0.7520(3) 0.2875(2) 0.51685(13) 0.0304(5) Uani 1 1 d . . . H19A H 0.7707 0.3220 0.5694 0.046 Uiso 1 1 calc R . . H19B H 0.7923 0.2002 0.5275 0.046 Uiso 1 1 calc R . . H19C H 0.6437 0.3086 0.5045 0.046 Uiso 1 1 calc R . . C20 C 0.7621(3) 0.4734(2) 0.42520(15) 0.0376(6) Uani 1 1 d . . . H20A H 0.6539 0.4935 0.4130 0.056 Uiso 1 1 calc R . . H20B H 0.8100 0.5088 0.3754 0.056 Uiso 1 1 calc R . . H20C H 0.7802 0.5051 0.4792 0.056 Uiso 1 1 calc R . . C21 C 0.8645(2) 0.02708(17) 0.38179(13) 0.0246(4) Uani 1 1 d . . . H21A H 0.8366 -0.0481 0.3898 0.037 Uiso 1 1 calc R . . H21B H 0.8811 0.0495 0.4398 0.037 Uiso 1 1 calc R . . H21C H 0.9568 0.0167 0.3481 0.037 Uiso 1 1 calc R . . C22 C 0.6008(2) 0.13279(17) 0.38119(13) 0.0210(4) Uani 1 1 d . . . H22A H 0.6177 0.1446 0.4430 0.025 Uiso 1 1 calc R . . H22B H 0.5739 0.0566 0.3830 0.025 Uiso 1 1 calc R . . C23 C 0.4703(2) 0.23374(18) 0.34103(13) 0.0227(4) Uani 1 1 d . . . H23A H 0.4552 0.2244 0.2784 0.027 Uiso 1 1 calc R . . H23B H 0.3780 0.2295 0.3729 0.027 Uiso 1 1 calc R . . C24 C 0.3559(2) 0.44618(19) 0.32337(14) 0.0296(5) Uani 1 1 d . . . H24A H 0.3774 0.5239 0.3187 0.044 Uiso 1 1 calc R . . H24B H 0.2833 0.4419 0.3700 0.044 Uiso 1 1 calc R . . H24C H 0.3142 0.4370 0.2668 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 Ga1 0.01681(11) 0.01528(10) 0.01595(11) -0.00126(8) -0.00101(8) -0.00244(8) Ga2 0.01505(10) 0.01788(11) 0.01570(11) -0.00138(8) -0.00044(8) -0.00524(8) N1 0.0217(8) 0.0175(8) 0.0161(8) -0.0024(6) -0.0006(6) -0.0016(7) N2 0.0171(8) 0.0199(8) 0.0231(9) -0.0018(7) -0.0015(6) -0.0015(6) N3 0.0181(8) 0.0195(8) 0.0137(7) -0.0026(6) -0.0008(6) -0.0044(6) N4 0.0177(8) 0.0229(9) 0.0204(8) -0.0048(7) 0.0056(6) -0.0040(7) O1 0.0321(8) 0.0144(7) 0.0209(7) -0.0001(5) -0.0079(6) -0.0014(6) O2 0.0185(7) 0.0304(8) 0.0188(7) -0.0038(6) -0.0006(6) -0.0048(6) O3 0.0258(7) 0.0181(7) 0.0123(6) -0.0033(5) -0.0006(5) -0.0065(6) O4 0.0160(6) 0.0232(7) 0.0173(7) -0.0016(5) 0.0013(5) -0.0043(5) C1 0.0202(9) 0.0214(10) 0.0196(10) -0.0042(8) -0.0018(8) 0.0016(8) C2 0.0225(11) 0.0355(13) 0.0371(13) -0.0099(10) 0.0083(9) -0.0037(9) C3 0.0306(12) 0.0314(12) 0.0281(12) -0.0015(9) -0.0066(9) 0.0061(9) C4 0.0313(12) 0.0325(12) 0.0258(11) -0.0122(9) -0.0019(9) 0.0040(9) C5 0.0249(10) 0.0187(10) 0.0251(10) 0.0014(8) -0.0006(8) -0.0080(8) C6 0.0355(12) 0.0243(11) 0.0285(12) 0.0029(9) 0.0043(9) -0.0119(9) C7 0.0395(13) 0.0254(11) 0.0379(13) -0.0038(10) -0.0028(10) -0.0131(10) C8 0.0233(11) 0.0326(12) 0.0411(14) -0.0025(10) 0.0033(9) -0.0114(9) C9 0.0287(11) 0.0294(11) 0.0209(10) -0.0021(9) 0.0054(8) -0.0031(9) C10 0.0194(9) 0.0227(10) 0.0261(11) -0.0037(8) -0.0030(8) -0.0030(8) C11 0.0219(10) 0.0231(10) 0.0237(10) -0.0012(8) -0.0063(8) -0.0005(8) C12 0.0304(11) 0.0205(10) 0.0300(12) 0.0016(9) 0.0006(9) -0.0004(9) C13 0.0191(9) 0.0242(10) 0.0279(11) -0.0006(8) 0.0037(8) -0.0069(8) C14 0.0228(10) 0.0440(14) 0.0230(11) -0.0005(10) 0.0067(8) -0.0070(10) C15 0.0185(10) 0.0527(16) 0.0399(14) -0.0095(12) 0.0040(9) -0.0078(10) C16 0.0601(17) 0.0348(14) 0.0557(17) -0.0066(12) 0.0307(14) -0.0249(13) C17 0.0307(11) 0.0245(10) 0.0207(10) -0.0028(8) -0.0042(8) -0.0123(9) C18 0.0370(13) 0.0582(17) 0.0301(13) -0.0023(12) -0.0095(10) -0.0242(12) C19 0.0388(13) 0.0367(13) 0.0195(11) -0.0063(9) 0.0001(9) -0.0154(10) C20 0.0620(17) 0.0287(12) 0.0250(12) -0.0083(10) -0.0034(11) -0.0152(11) C21 0.0264(11) 0.0214(10) 0.0230(10) 0.0004(8) -0.0051(8) -0.0031(8) C22 0.0231(10) 0.0253(10) 0.0174(9) -0.0029(8) 0.0037(8) -0.0112(8) C23 0.0181(9) 0.0288(11) 0.0230(10) -0.0057(8) 0.0049(8) -0.0090(8) C24 0.0213(10) 0.0311(12) 0.0323(12) -0.0073(9) 0.0053(9) 0.0007(9) _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 O3 1.9372(13) . ? Ga1 O1 1.9534(13) . ? Ga1 C1 2.0219(19) . ? Ga1 C5 2.0225(19) . ? Ga2 O4 1.8766(13) . ? Ga2 C13 2.005(2) . ? Ga2 C17 2.025(2) . ? Ga2 N3 2.1246(16) . ? N1 H1N 0.87(2) . ? N1 O1 1.405(2) . ? N1 C9 1.477(2) . ? N1 C10 1.496(2) . ? N2 C11 1.452(2) . ? N2 O2 1.454(2) . ? N2 C12 1.465(2) . ? N3 O3 1.4345(19) . ? N3 C21 1.475(2) . ? N3 C22 1.482(2) . ? N4 O4 1.4564(19) . ? N4 C23 1.459(2) . ? N4 C24 1.461(2) . ? O2 H2O 0.83(3) . ? C1 C2 1.525(3) . ? C1 C3 1.527(3) . ? C1 C4 1.528(3) . ? C5 C6 1.532(3) . ? C5 C8 1.532(3) . ? C5 C7 1.535(3) . ? C10 C11 1.514(3) . ? C13 C14 1.521(3) . ? C13 C16 1.531(3) . ? C13 C15 1.533(3) . ? C17 C19 1.525(3) . ? C17 C18 1.529(3) . ? C17 C20 1.536(3) . ? C22 C23 1.508(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 O3 Ga1 O1 91.06(5) . . ? O3 Ga1 C1 110.76(7) . . ? O1 Ga1 C1 104.55(7) . . ? O3 Ga1 C5 119.98(7) . . ? O1 Ga1 C5 102.76(7) . . ? C1 Ga1 C5 120.94(8) . . ? O4 Ga2 C13 109.20(7) . . ? O4 Ga2 C17 110.89(7) . . ? C13 Ga2 C17 119.83(8) . . ? O4 Ga2 N3 90.64(6) . . ? C13 Ga2 N3 111.44(7) . . ? C17 Ga2 N3 111.01(7) . . ? H1N N1 O1 111.7(16) . . ? H1N N1 C9 108.3(15) . . ? O1 N1 C9 108.51(14) . . ? H1N N1 C10 108.1(15) . . ? O1 N1 C10 106.95(14) . . ? C9 N1 C10 113.27(15) . . ? C11 N2 O2 103.36(14) . . ? C11 N2 C12 110.01(16) . . ? O2 N2 C12 106.11(14) . . ? O3 N3 C21 108.12(14) . . ? O3 N3 C22 108.45(13) . . ? C21 N3 C22 109.55(15) . . ? O3 N3 Ga2 109.97(10) . . ? C21 N3 Ga2 111.21(11) . . ? C22 N3 Ga2 109.49(11) . . ? O4 N4 C23 106.76(13) . . ? O4 N4 C24 105.32(14) . . ? C23 N4 C24 110.71(16) . . ? N1 O1 Ga1 119.68(10) . . ? H2O O2 N2 99.4(17) . . ? N3 O3 Ga1 126.15(10) . . ? N4 O4 Ga2 107.52(10) . . ? C2 C1 C3 108.53(17) . . ? C2 C1 C4 107.75(17) . . ? C3 C1 C4 108.51(17) . . ? C2 C1 Ga1 112.37(13) . . ? C3 C1 Ga1 110.73(14) . . ? C4 C1 Ga1 108.84(13) . . ? C6 C5 C8 109.48(17) . . ? C6 C5 C7 108.22(17) . . ? C8 C5 C7 107.48(17) . . ? C6 C5 Ga1 113.94(13) . . ? C8 C5 Ga1 112.28(13) . . ? C7 C5 Ga1 105.07(14) . . ? N1 C10 C11 115.83(16) . . ? N2 C11 C10 112.91(16) . . ? C14 C13 C16 108.22(19) . . ? C14 C13 C15 107.85(17) . . ? C16 C13 C15 108.34(18) . . ? C14 C13 Ga2 114.13(13) . . ? C16 C13 Ga2 106.62(14) . . ? C15 C13 Ga2 111.50(14) . . ? C19 C17 C18 108.16(17) . . ? C19 C17 C20 106.93(18) . . ? C18 C17 C20 108.51(18) . . ? C19 C17 Ga2 117.20(14) . . ? C18 C17 Ga2 111.77(15) . . ? C20 C17 Ga2 103.81(13) . . ? N3 C22 C23 114.24(15) . . ? N4 C23 C22 111.92(16) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.597 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.077