_publ_contact_author_name 'Dr. Andrea Erxleben' _publ_contact_author_address ; National University of Ireland, Galway Chemistry Department University Road Galway Ireland ; _publ_contact_author_mail 'Andrea.Erxleben@nuigalway.ie' _publ_contact_author_fax '+353-91-525700' _publ_contact_author_phone '+353-91-492483' _publ_contact_letter ? _publ_requested_journal 'Inorganic Chemistry' _publ_title ; GaIII Complexes as Models for the MIII Site of Purple Acid Phosphatase: Ligand Effects on the Hydrolytic Reactivity Toward Bis(2,4-dinitrophenyl) phosphate ; _publ_author_address ; Fergal Coleman, Michael J. Hynes, Andrea Erxleben National University of Ireland, Galway Chemistry Department University Road Galway Ireland ; data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 Ga2 N4 O14' _chemical_formula_weight 689.92 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 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 8.8492(3) _cell_length_b 10.4470(4) _cell_length_c 14.0948(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.216(2) _cell_angle_gamma 90.00 _cell_volume 1303.02(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2653 _cell_measurement_theta_min 2.89 _cell_measurement_theta_max 26.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.146 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6735 _exptl_absorpt_correction_T_max 0.8140 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8736 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2653 _reflns_number_gt 2087 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0551P)^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 'riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2653 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0862 _refine_ls_wR_factor_gt 0.0844 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.003 _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 0.47007(3) 0.41688(3) 0.41700(2) 0.01626(11) Uani 1 1 d . . . O5 O 0.4388(2) 0.42208(17) 0.55613(13) 0.0166(4) Uani 1 1 d . . . H5A H 0.3930 0.3632 0.5964 0.020 Uiso 1 1 calc R . . O4 O 0.7329(3) 0.1103(2) 0.4537(2) 0.0445(7) Uani 1 1 d . . . O3 O 0.6501(2) 0.3093(2) 0.43601(15) 0.0267(5) Uani 1 1 d . . . O1 O 0.5152(2) 0.42102(18) 0.27991(13) 0.0242(5) Uani 1 1 d . . . O2 O 0.5151(2) 0.2984(2) 0.15215(14) 0.0315(5) Uani 1 1 d . . . N1 N 0.2447(2) 0.4670(2) 0.39509(16) 0.0211(5) Uani 1 1 d . . . N2 N 0.3709(2) 0.2380(2) 0.38743(16) 0.0176(5) Uani 1 1 d . . . O1W O 0.8545(3) -0.0972(3) 0.3485(2) 0.0561(8) Uani 1 1 d . . . O2W O 0.8243(3) 0.0671(3) 0.6437(2) 0.0609(8) Uani 1 1 d . . . C1 C 0.1478(3) 0.3691(3) 0.4033(2) 0.0237(6) Uani 1 1 d . . . C2 C -0.0067(3) 0.3851(3) 0.3908(2) 0.0330(8) Uani 1 1 d . . . H2 H -0.0720 0.3157 0.3958 0.040 Uiso 1 1 calc R . . C3 C -0.0616(4) 0.5048(4) 0.3710(3) 0.0407(9) Uani 1 1 d . . . H3 H -0.1650 0.5181 0.3642 0.049 Uiso 1 1 calc R . . C4 C 0.0377(4) 0.6052(3) 0.3612(3) 0.0394(9) Uani 1 1 d . . . H4 H 0.0024 0.6866 0.3462 0.047 Uiso 1 1 calc R . . C5 C 0.1910(4) 0.5836(3) 0.3740(2) 0.0293(7) Uani 1 1 d . . . H5 H 0.2581 0.6515 0.3678 0.035 Uiso 1 1 calc R . . C6 C 0.2167(3) 0.2414(3) 0.4270(2) 0.0246(7) Uani 1 1 d . . . H6A H 0.2205 0.2298 0.4953 0.030 Uiso 1 1 calc R . . H6B H 0.1562 0.1730 0.3999 0.030 Uiso 1 1 calc R . . C7 C 0.3685(3) 0.2279(3) 0.2817(2) 0.0228(6) Uani 1 1 d . . . H7A H 0.2665 0.2439 0.2591 0.027 Uiso 1 1 calc R . . H7B H 0.3956 0.1414 0.2636 0.027 Uiso 1 1 calc R . . C8 C 0.4752(3) 0.3207(3) 0.2338(2) 0.0211(6) Uani 1 1 d . . . C9 C 0.4714(3) 0.1402(3) 0.4304(2) 0.0248(7) Uani 1 1 d . . . H9A H 0.4705 0.0638 0.3912 0.030 Uiso 1 1 calc R . . H9B H 0.4336 0.1172 0.4926 0.030 Uiso 1 1 calc R . . C10 C 0.6311(3) 0.1886(3) 0.4397(2) 0.0259(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.01786(17) 0.01329(16) 0.01761(17) -0.00175(13) 0.00034(11) -0.00087(12) O5 0.0216(10) 0.0131(9) 0.0151(9) -0.0001(8) 0.0018(8) -0.0050(8) O4 0.0336(13) 0.0331(14) 0.0667(18) -0.0026(12) -0.0073(12) 0.0155(11) O3 0.0179(10) 0.0214(11) 0.0407(13) -0.0033(10) -0.0020(9) 0.0013(9) O1 0.0364(12) 0.0183(10) 0.0180(10) -0.0020(9) 0.0042(9) -0.0086(9) O2 0.0478(14) 0.0259(12) 0.0209(11) -0.0044(9) 0.0090(10) -0.0037(10) N1 0.0179(12) 0.0212(12) 0.0244(13) -0.0019(10) -0.0030(10) 0.0018(10) N2 0.0180(11) 0.0156(12) 0.0192(12) 0.0009(10) -0.0003(9) 0.0003(9) O1W 0.0543(17) 0.0504(18) 0.0636(19) -0.0124(14) -0.0033(14) -0.0014(13) O2W 0.0461(16) 0.0551(19) 0.082(2) -0.0057(16) -0.0110(15) 0.0077(14) C1 0.0219(15) 0.0252(15) 0.0242(15) -0.0040(13) 0.0035(12) -0.0016(13) C2 0.0209(15) 0.0381(19) 0.0402(19) -0.0029(15) 0.0022(14) -0.0045(14) C3 0.0210(16) 0.049(2) 0.052(2) -0.0048(19) -0.0047(15) 0.0088(16) C4 0.0341(18) 0.035(2) 0.049(2) 0.0019(16) -0.0064(16) 0.0154(15) C5 0.0293(16) 0.0219(15) 0.0367(18) 0.0000(14) -0.0049(14) 0.0029(13) C6 0.0218(14) 0.0243(16) 0.0279(16) 0.0004(13) 0.0052(13) -0.0050(12) C7 0.0285(15) 0.0189(15) 0.0211(15) -0.0046(12) -0.0020(12) -0.0024(12) C8 0.0241(15) 0.0182(15) 0.0210(15) 0.0007(12) -0.0011(12) 0.0023(12) C9 0.0313(16) 0.0144(14) 0.0289(17) 0.0012(12) -0.0042(13) 0.0005(13) C10 0.0263(15) 0.0248(17) 0.0265(16) -0.0035(13) -0.0024(13) 0.0074(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 O5 1.9033(18) 3_666 ? Ga1 O3 1.967(2) . ? Ga1 O1 1.9750(19) . ? Ga1 O5 1.9823(18) . ? Ga1 N1 2.084(2) . ? Ga1 N2 2.105(2) . ? Ga1 Ga1 2.9600(6) 3_666 ? O5 Ga1 1.9033(18) 3_666 ? O4 C10 1.232(4) . ? O3 C10 1.273(4) . ? O1 C8 1.282(3) . ? O2 C8 1.227(3) . ? N1 C1 1.340(4) . ? N1 C5 1.341(4) . ? N2 C6 1.477(4) . ? N2 C9 1.483(4) . ? N2 C7 1.494(3) . ? C1 C2 1.389(4) . ? C1 C6 1.504(4) . ? C2 C3 1.370(5) . ? C3 C4 1.376(5) . ? C4 C5 1.386(4) . ? C7 C8 1.514(4) . ? C9 C10 1.506(4) . ? 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 O5 Ga1 O3 97.79(8) 3_666 . ? O5 Ga1 O1 95.06(8) 3_666 . ? O3 Ga1 O1 88.80(9) . . ? O5 Ga1 O5 80.77(8) 3_666 . ? O3 Ga1 O5 89.84(8) . . ? O1 Ga1 O5 175.40(8) . . ? O5 Ga1 N1 102.25(9) 3_666 . ? O3 Ga1 N1 159.69(9) . . ? O1 Ga1 N1 92.67(9) . . ? O5 Ga1 N1 90.14(8) . . ? O5 Ga1 N2 179.54(8) 3_666 . ? O3 Ga1 N2 81.75(8) . . ? O1 Ga1 N2 84.92(8) . . ? O5 Ga1 N2 99.23(8) . . ? N1 Ga1 N2 78.21(9) . . ? O5 Ga1 Ga1 41.38(5) 3_666 3_666 ? O3 Ga1 Ga1 94.89(6) . 3_666 ? O1 Ga1 Ga1 136.40(6) . 3_666 ? O5 Ga1 Ga1 39.40(5) . 3_666 ? N1 Ga1 Ga1 97.94(7) . 3_666 ? N2 Ga1 Ga1 138.63(6) . 3_666 ? Ga1 O5 Ga1 99.23(8) 3_666 . ? C10 O3 Ga1 117.70(19) . . ? C8 O1 Ga1 114.94(17) . . ? C1 N1 C5 119.1(3) . . ? C1 N1 Ga1 114.1(2) . . ? C5 N1 Ga1 126.8(2) . . ? C6 N2 C9 114.6(2) . . ? C6 N2 C7 111.6(2) . . ? C9 N2 C7 111.4(2) . . ? C6 N2 Ga1 106.81(17) . . ? C9 N2 Ga1 106.39(16) . . ? C7 N2 Ga1 105.33(16) . . ? N1 C1 C2 121.8(3) . . ? N1 C1 C6 116.0(2) . . ? C2 C1 C6 122.3(3) . . ? C3 C2 C1 119.0(3) . . ? C2 C3 C4 119.4(3) . . ? C3 C4 C5 119.2(3) . . ? N1 C5 C4 121.5(3) . . ? N2 C6 C1 108.2(2) . . ? N2 C7 C8 113.1(2) . . ? O2 C8 O1 123.4(3) . . ? O2 C8 C7 118.6(3) . . ? O1 C8 C7 117.9(2) . . ? N2 C9 C10 111.4(2) . . ? O4 C10 O3 124.6(3) . . ? O4 C10 C9 118.4(3) . . ? O3 C10 C9 116.9(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.703 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.082 #===END data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H30 Ga2 N4 O14' _chemical_formula_weight 593.84 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' 'Ga' 'Ga' 0.2307 1.6083 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8500(7) _cell_length_b 10.0850(12) _cell_length_c 13.983(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.360(13) _cell_angle_gamma 90.00 _cell_volume 1097.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2235 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 26.37 _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.530 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.5173 _exptl_absorpt_correction_T_max 0.6316 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7619 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2235 _reflns_number_gt 1896 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0481P)^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 'riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2235 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0728 _refine_ls_wR_factor_gt 0.0719 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.47630(3) 0.42146(2) 0.410234(17) 0.01762(10) Uani 1 1 d . . . O1 O 0.6966(2) 0.47936(17) 0.36864(12) 0.0291(4) Uani 1 1 d . . . O2 O 0.9549(3) 0.4103(2) 0.35131(19) 0.0550(6) Uani 1 1 d . . . O3 O 0.3560(2) 0.43900(15) 0.27721(12) 0.0237(4) Uani 1 1 d . . . O4 O 0.3183(3) 0.34873(19) 0.13059(13) 0.0413(5) Uani 1 1 d . . . O5 O 0.4147(2) 0.58783(14) 0.45245(12) 0.0200(3) Uani 1 1 d . . . H5 H 0.3029 0.6013 0.4342 0.024 Uiso 1 1 d . . . N1 N 0.5639(3) 0.24566(18) 0.35813(15) 0.0259(5) Uani 1 1 d . . . N2 N 0.2838(3) 0.3070(2) 0.44894(14) 0.0252(4) Uani 1 1 d . . . H2A H 0.2928 0.3011 0.5136 0.030 Uiso 1 1 calc R . . H2B H 0.1815 0.3436 0.4274 0.030 Uiso 1 1 calc R . . C1 C 0.7489(4) 0.2515(3) 0.3799(2) 0.0364(6) Uani 1 1 d . . . H1A H 0.8013 0.1916 0.3380 0.044 Uiso 1 1 calc R . . H1B H 0.7835 0.2246 0.4461 0.044 Uiso 1 1 calc R . . C2 C 0.8073(3) 0.3904(3) 0.3653(2) 0.0349(6) Uani 1 1 d . . . C3 C 0.5080(4) 0.2434(2) 0.25110(18) 0.0318(6) Uani 1 1 d . . . H3A H 0.6089 0.2515 0.2180 0.038 Uiso 1 1 calc R . . H3B H 0.4555 0.1582 0.2339 0.038 Uiso 1 1 calc R . . C4 C 0.3836(3) 0.3509(2) 0.21607(17) 0.0267(5) Uani 1 1 d . . . C5 C 0.4804(4) 0.1416(3) 0.4096(2) 0.0386(7) Uani 1 1 d . . . H5A H 0.5344 0.1359 0.4758 0.046 Uiso 1 1 calc R . . H5B H 0.4922 0.0564 0.3789 0.046 Uiso 1 1 calc R . . C6 C 0.2960(4) 0.1754(3) 0.4072(2) 0.0347(6) Uani 1 1 d . . . H6A H 0.2399 0.1747 0.3412 0.042 Uiso 1 1 calc R . . H6B H 0.2397 0.1108 0.4438 0.042 Uiso 1 1 calc R . . O1W O 0.9053(3) 0.1582(3) 0.1108(3) 0.1006(11) Uani 1 1 d . . . O2W O 0.9822(4) 0.4199(3) 0.1421(2) 0.0797(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.02016(15) 0.01650(15) 0.01599(15) -0.00203(9) 0.00151(10) 0.00088(10) O1 0.0228(9) 0.0294(9) 0.0360(10) 0.0000(8) 0.0076(8) -0.0003(7) O2 0.0233(11) 0.0721(16) 0.0717(18) 0.0043(12) 0.0141(11) 0.0055(10) O3 0.0298(9) 0.0230(8) 0.0175(8) -0.0017(6) 0.0002(7) 0.0029(7) O4 0.0546(13) 0.0467(12) 0.0200(10) -0.0080(8) -0.0045(9) 0.0066(10) O5 0.0204(8) 0.0194(8) 0.0192(8) -0.0027(6) -0.0018(7) 0.0050(6) N1 0.0353(12) 0.0212(10) 0.0213(11) -0.0026(8) 0.0045(9) 0.0056(9) N2 0.0244(11) 0.0297(11) 0.0212(10) 0.0024(8) 0.0018(8) -0.0039(9) C1 0.0338(15) 0.0368(15) 0.0382(16) -0.0019(12) 0.0030(12) 0.0167(12) C2 0.0260(14) 0.0486(17) 0.0302(15) 0.0011(12) 0.0039(12) 0.0062(12) C3 0.0459(16) 0.0279(13) 0.0217(13) -0.0070(10) 0.0051(11) 0.0045(11) C4 0.0331(14) 0.0283(13) 0.0195(13) -0.0016(10) 0.0058(11) -0.0055(11) C5 0.064(2) 0.0178(13) 0.0338(16) 0.0008(11) 0.0071(14) -0.0004(13) C6 0.0477(17) 0.0273(13) 0.0288(14) -0.0032(11) 0.0039(12) -0.0153(12) O1W 0.0501(16) 0.076(2) 0.160(3) 0.034(2) -0.0470(17) -0.0232(15) O2W 0.0596(18) 0.084(2) 0.093(2) -0.0034(15) -0.0003(17) 0.0119(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 O5 1.8629(14) . ? Ga1 O1 1.9818(16) . ? Ga1 O3 1.9833(17) . ? Ga1 O5 2.0016(17) 3_666 ? Ga1 N2 2.0291(19) . ? Ga1 N1 2.0676(18) . ? O1 C2 1.254(3) . ? O2 C2 1.216(3) . ? O3 C4 1.271(3) . ? O4 C4 1.239(3) . ? O5 Ga1 2.0016(17) 3_666 ? O5 H5 0.8926 . ? N1 C1 1.446(3) . ? N1 C5 1.472(3) . ? N1 C3 1.505(3) . ? N2 C6 1.458(3) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? C1 C2 1.495(4) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C3 C4 1.499(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.484(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? 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 O5 Ga1 O1 95.69(7) . . ? O5 Ga1 O3 96.03(7) . . ? O1 Ga1 O3 91.56(7) . . ? O5 Ga1 O5 80.48(7) . 3_666 ? O1 Ga1 O5 90.78(7) . 3_666 ? O3 Ga1 O5 175.98(6) . 3_666 ? O5 Ga1 N2 101.27(7) . . ? O1 Ga1 N2 162.45(8) . . ? O3 Ga1 N2 91.11(8) . . ? O5 Ga1 N2 87.64(7) 3_666 . ? O5 Ga1 N1 174.52(7) . . ? O1 Ga1 N1 78.88(8) . . ? O3 Ga1 N1 83.45(7) . . ? O5 Ga1 N1 100.21(7) 3_666 . ? N2 Ga1 N1 84.20(8) . . ? C2 O1 Ga1 115.78(17) . . ? C4 O3 Ga1 117.82(16) . . ? Ga1 O5 Ga1 99.52(7) . 3_666 ? Ga1 O5 H5 109.4 . . ? Ga1 O5 H5 124.4 3_666 . ? C1 N1 C5 115.1(2) . . ? C1 N1 C3 111.51(19) . . ? C5 N1 C3 112.6(2) . . ? C1 N1 Ga1 105.13(15) . . ? C5 N1 Ga1 104.48(14) . . ? C3 N1 Ga1 107.20(14) . . ? C6 N2 Ga1 108.75(15) . . ? C6 N2 H2A 109.9 . . ? Ga1 N2 H2A 109.9 . . ? C6 N2 H2B 109.9 . . ? Ga1 N2 H2B 109.9 . . ? H2A N2 H2B 108.3 . . ? N1 C1 C2 109.1(2) . . ? N1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? N1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? O2 C2 O1 124.5(3) . . ? O2 C2 C1 119.5(2) . . ? O1 C2 C1 116.0(2) . . ? C4 C3 N1 114.13(19) . . ? C4 C3 H3A 108.7 . . ? N1 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? N1 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? O4 C4 O3 125.2(2) . . ? O4 C4 C3 118.3(2) . . ? O3 C4 C3 116.5(2) . . ? N1 C5 C6 108.6(2) . . ? N1 C5 H5A 110.0 . . ? C6 C5 H5A 110.0 . . ? N1 C5 H5B 110.0 . . ? C6 C5 H5B 110.0 . . ? H5A C5 H5B 108.3 . . ? N2 C6 C5 108.3(2) . . ? N2 C6 H6A 110.0 . . ? C5 C6 H6A 110.0 . . ? N2 C6 H6B 110.0 . . ? C5 C6 H6B 110.0 . . ? H6A C6 H6B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.617 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.073 #===END data_4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H26 Cl Ga N4 O10' _chemical_formula_weight 491.54 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 12.3409(7) _cell_length_b 16.9744(10) _cell_length_c 9.6776(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2027.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 14392 _cell_measurement_theta_min 2.93 _cell_measurement_theta_max 26.37 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 1.546 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7474 _exptl_absorpt_correction_T_max 0.9267 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14392 _diffrn_reflns_av_R_equivalents 0.0946 _diffrn_reflns_av_sigmaI/netI 0.0473 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2072 _reflns_number_gt 1470 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0866P)^2^+4.2101P] 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 'riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2072 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1695 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.0000 0.0000 0.0000 0.0263(3) Uani 1 2 d S . . N1 N 0.0654(3) 0.0340(2) 0.1896(3) 0.0248(8) Uani 1 1 d . . . O1 O 0.1450(3) -0.0387(2) -0.0414(3) 0.0446(9) Uani 1 1 d . . . O3 O -0.0312(3) -0.0997(2) 0.0915(3) 0.0476(10) Uani 1 1 d . . . O2 O 0.3101(3) -0.0488(3) 0.0449(4) 0.0494(10) Uani 1 1 d . . . N2 N 0.0619(4) 0.2199(2) 0.4054(5) 0.0464(11) Uani 1 1 d . . . H2A H 0.0952 0.2327 0.4838 0.070 Uiso 1 1 calc R . . H2B H -0.0094 0.2239 0.4168 0.070 Uiso 1 1 calc R . . H2C H 0.0831 0.2524 0.3385 0.070 Uiso 1 1 calc R . . O4 O -0.0148(4) -0.1610(3) 0.2920(4) 0.0740(16) Uani 1 1 d . . . Cl1 Cl 0.2500 0.2500 0.1241(2) 0.0558(6) Uani 1 2 d S . . C1 C 0.2161(4) -0.0253(3) 0.0496(5) 0.0322(10) Uani 1 1 d . . . C2 C 0.1841(3) 0.0270(3) 0.1696(5) 0.0338(11) Uani 1 1 d . . . H2D H 0.2161 0.0062 0.2536 0.041 Uiso 1 1 calc R . . H2E H 0.2140 0.0792 0.1547 0.041 Uiso 1 1 calc R . . C3 C 0.0240(4) -0.0260(3) 0.2880(4) 0.0303(10) Uani 1 1 d . . . H3A H -0.0384 -0.0046 0.3360 0.036 Uiso 1 1 calc R . . H3B H 0.0795 -0.0366 0.3565 0.036 Uiso 1 1 calc R . . C4 C -0.0079(4) -0.1020(3) 0.2207(5) 0.0376(12) Uani 1 1 d . . . C5 C 0.0355(4) 0.1151(3) 0.2342(5) 0.0305(10) Uani 1 1 d . . . H5A H -0.0425 0.1180 0.2458 0.037 Uiso 1 1 calc R . . H5B H 0.0558 0.1521 0.1624 0.037 Uiso 1 1 calc R . . C6 C 0.0896(4) 0.1388(3) 0.3678(5) 0.0384(11) Uani 1 1 d . . . H6A H 0.0669 0.1034 0.4410 0.046 Uiso 1 1 calc R . . H6B H 0.1676 0.1342 0.3578 0.046 Uiso 1 1 calc R . . O1W O 0.8423(6) 0.2084(5) 0.4846(12) 0.181(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0323(4) 0.0292(4) 0.0175(4) -0.0021(3) -0.0038(2) 0.0009(3) N1 0.0308(19) 0.0249(19) 0.0188(17) -0.0006(14) -0.0022(14) 0.0014(16) O1 0.0368(18) 0.069(3) 0.0283(16) -0.0188(18) -0.0031(14) 0.0119(18) O3 0.080(3) 0.038(2) 0.0254(17) 0.0031(15) -0.0127(17) -0.0204(19) O2 0.0316(19) 0.073(3) 0.0433(19) -0.014(2) 0.0029(16) 0.0064(18) N2 0.064(3) 0.032(2) 0.043(2) -0.0125(19) -0.012(2) 0.001(2) O4 0.143(5) 0.046(2) 0.033(2) 0.0103(19) -0.012(2) -0.037(3) Cl1 0.0512(11) 0.0746(14) 0.0415(10) 0.000 0.000 -0.0138(11) C1 0.033(2) 0.039(3) 0.024(2) -0.001(2) 0.0006(18) -0.002(2) C2 0.023(2) 0.051(3) 0.028(2) -0.009(2) -0.0002(17) 0.000(2) C3 0.041(3) 0.032(2) 0.018(2) -0.0035(19) 0.0026(18) -0.0040(19) C4 0.046(3) 0.038(3) 0.029(2) -0.002(2) 0.004(2) -0.011(2) C5 0.036(2) 0.028(2) 0.028(2) -0.0030(19) -0.0039(19) 0.0029(19) C6 0.058(3) 0.032(3) 0.026(2) -0.008(2) -0.007(2) 0.006(2) O1W 0.088(5) 0.107(6) 0.349(17) -0.008(7) 0.025(7) 0.007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ga1 O3 1.948(3) 5 ? Ga1 O3 1.948(3) . ? Ga1 O1 1.948(3) 5 ? Ga1 O1 1.948(3) . ? Ga1 N1 2.086(3) . ? Ga1 N1 2.086(3) 5 ? N1 C2 1.482(5) . ? N1 C3 1.486(6) . ? N1 C5 1.489(6) . ? O1 C1 1.264(6) . ? O3 C4 1.284(6) . ? O2 C1 1.228(6) . ? N2 C6 1.465(6) . ? O4 C4 1.218(7) . ? C1 C2 1.515(6) . ? C3 C4 1.498(7) . ? C5 C6 1.509(6) . ? 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 O3 180.0(3) 5 . ? O3 Ga1 O1 88.99(18) 5 5 ? O3 Ga1 O1 91.01(18) . 5 ? O3 Ga1 O1 91.01(18) 5 . ? O3 Ga1 O1 88.99(18) . . ? O1 Ga1 O1 180.0(2) 5 . ? O3 Ga1 N1 94.75(13) 5 . ? O3 Ga1 N1 85.25(13) . . ? O1 Ga1 N1 94.66(13) 5 . ? O1 Ga1 N1 85.34(13) . . ? O3 Ga1 N1 85.25(13) 5 5 ? O3 Ga1 N1 94.75(13) . 5 ? O1 Ga1 N1 85.34(13) 5 5 ? O1 Ga1 N1 94.66(13) . 5 ? N1 Ga1 N1 180.0(3) . 5 ? C2 N1 C3 111.6(4) . . ? C2 N1 C5 110.9(4) . . ? C3 N1 C5 111.2(3) . . ? C2 N1 Ga1 104.2(2) . . ? C3 N1 Ga1 103.9(2) . . ? C5 N1 Ga1 114.5(3) . . ? C1 O1 Ga1 115.7(3) . . ? C4 O3 Ga1 115.2(3) . . ? O2 C1 O1 124.8(5) . . ? O2 C1 C2 117.7(4) . . ? O1 C1 C2 117.3(4) . . ? N1 C2 C1 113.9(4) . . ? N1 C3 C4 113.7(4) . . ? O4 C4 O3 124.2(5) . . ? O4 C4 C3 118.6(4) . . ? O3 C4 C3 117.1(4) . . ? N1 C5 C6 112.6(4) . . ? N2 C6 C5 111.1(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.111 _refine_diff_density_min -0.429 _refine_diff_density_rms 0.112 #===END data_6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H36 Ga2 N8 O15' _chemical_formula_weight 864.09 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' 'Ga' 'Ga' 0.2307 1.6083 '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' _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 12.1675(4) _cell_length_b 10.1530(3) _cell_length_c 14.3743(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.478(2) _cell_angle_gamma 90.00 _cell_volume 1770.33(9) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3536 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 26.37 _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 1.603 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.6449 _exptl_absorpt_correction_T_max 0.7950 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9049 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3536 _reflns_number_gt 2751 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET) (compiled Jan 8 2009,16:24:04) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0856P)^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 'riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3536 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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 0.02533(3) 0.42206(3) 0.416424(19) 0.02012(14) Uani 1 1 d . . . O1 O 0.0122(2) 0.4349(2) 0.27884(14) 0.0284(5) Uani 1 1 d . . . O3 O -0.03472(19) 0.58673(18) 0.44543(13) 0.0227(5) Uani 1 1 d . . . H3 H -0.0614 0.6538 0.4058 0.027 Uiso 1 1 calc R . . N2 N 0.1901(2) 0.4686(3) 0.41561(17) 0.0283(6) Uani 1 1 d . . . N1 N -0.1174(2) 0.3121(3) 0.40094(17) 0.0264(6) Uani 1 1 d . . . N3 N 0.0922(2) 0.2363(2) 0.39521(16) 0.0215(6) Uani 1 1 d . . . O6 O 0.3283(8) 0.3281(7) 0.1563(6) 0.249(5) Uani 1 1 d . . . O4 O 0.4634(4) 0.2440(7) 0.2241(4) 0.147(2) Uani 1 1 d . . . O5 O 0.3250(6) 0.1396(6) 0.1824(6) 0.189(3) Uani 1 1 d . . . N4 N 0.3739(4) 0.2382(5) 0.1837(3) 0.0661(11) Uani 1 1 d . . . O2 O 0.0198(3) 0.3135(2) 0.15250(14) 0.0445(7) Uani 1 1 d . . . O1W O 0.5809(9) 0.4890(11) 0.1499(7) 0.120(3) Uiso 0.50 1 d P . . O2W O 0.7755(10) 0.4167(9) 0.1197(8) 0.119(3) Uiso 0.50 1 d P . . O3W O 0.5073(16) 0.4144(14) 0.0247(12) 0.203(7) Uiso 0.50 1 d P . . C1 C -0.1013(3) 0.1803(3) 0.4048(2) 0.0281(8) Uani 1 1 d . . . C2 C -0.1869(4) 0.0949(4) 0.3851(3) 0.0440(10) Uani 1 1 d . . . H2 H -0.1751 0.0044 0.3882 0.053 Uiso 1 1 calc R . . C3 C -0.2899(4) 0.1436(5) 0.3607(3) 0.0562(12) Uani 1 1 d . . . H3A H -0.3487 0.0864 0.3469 0.067 Uiso 1 1 calc R . . C4 C -0.3064(4) 0.2787(5) 0.3566(3) 0.0525(11) Uani 1 1 d . . . H4 H -0.3760 0.3134 0.3403 0.063 Uiso 1 1 calc R . . C5 C -0.2180(3) 0.3599(4) 0.3772(2) 0.0383(9) Uani 1 1 d . . . H5 H -0.2282 0.4506 0.3747 0.046 Uiso 1 1 calc R . . C7 C 0.0147(3) 0.1385(3) 0.4317(2) 0.0274(8) Uani 1 1 d . . . H7A H 0.0266 0.1330 0.4991 0.033 Uiso 1 1 calc R . . H7B H 0.0279 0.0521 0.4059 0.033 Uiso 1 1 calc R . . C8 C 0.2042(3) 0.2358(3) 0.4458(2) 0.0330(8) Uani 1 1 d . . . H8A H 0.2476 0.1633 0.4243 0.040 Uiso 1 1 calc R . . H8B H 0.1983 0.2256 0.5124 0.040 Uiso 1 1 calc R . . C9 C 0.2579(3) 0.3645(4) 0.4262(2) 0.0349(8) Uani 1 1 d . . . C10 C 0.3695(4) 0.3794(5) 0.4184(3) 0.0573(12) Uani 1 1 d . . . H10 H 0.4163 0.3071 0.4257 0.069 Uiso 1 1 calc R . . C11 C 0.4109(4) 0.5008(6) 0.3998(4) 0.0675(14) Uani 1 1 d . . . H11 H 0.4862 0.5115 0.3949 0.081 Uiso 1 1 calc R . . C12 C 0.3417(4) 0.6065(5) 0.3886(3) 0.0556(12) Uani 1 1 d . . . H12 H 0.3688 0.6895 0.3754 0.067 Uiso 1 1 calc R . . C13 C 0.2313(3) 0.5877(4) 0.3972(2) 0.0387(9) Uani 1 1 d . . . H13 H 0.1837 0.6594 0.3901 0.046 Uiso 1 1 calc R . . C14 C 0.0975(3) 0.2219(3) 0.29277(19) 0.0284(8) Uani 1 1 d . . . H14A H 0.0656 0.1377 0.2735 0.034 Uiso 1 1 calc R . . H14B H 0.1742 0.2212 0.2788 0.034 Uiso 1 1 calc R . . C15 C 0.0380(3) 0.3300(3) 0.23661(19) 0.0268(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ga1 0.0357(2) 0.0123(2) 0.01250(19) -0.00173(12) 0.00331(13) -0.00012(15) O1 0.0557(16) 0.0157(11) 0.0138(10) 0.0010(8) 0.0030(10) 0.0061(11) O3 0.0422(14) 0.0137(10) 0.0121(9) 0.0002(8) 0.0024(8) 0.0059(9) N2 0.0377(17) 0.0258(14) 0.0215(13) -0.0020(11) 0.0038(11) -0.0053(13) N1 0.0370(17) 0.0223(14) 0.0200(13) -0.0038(11) 0.0024(11) -0.0013(12) N3 0.0348(16) 0.0144(12) 0.0155(12) -0.0002(10) 0.0031(10) 0.0014(11) O6 0.331(12) 0.118(6) 0.268(9) 0.011(6) -0.173(9) 0.056(7) O4 0.072(4) 0.200(6) 0.162(5) -0.046(4) -0.028(3) 0.024(4) O5 0.160(7) 0.102(4) 0.310(9) -0.060(5) 0.054(6) -0.060(5) N4 0.057(3) 0.059(3) 0.081(3) -0.014(2) -0.001(2) 0.016(2) O2 0.095(2) 0.0237(13) 0.0151(11) -0.0014(9) 0.0021(12) 0.0075(14) C1 0.047(2) 0.0195(15) 0.0189(15) -0.0026(12) 0.0083(14) -0.0053(15) C2 0.055(3) 0.029(2) 0.049(2) -0.0062(17) 0.0082(19) -0.0125(19) C3 0.046(3) 0.051(3) 0.072(3) -0.016(2) 0.007(2) -0.020(2) C4 0.034(2) 0.066(3) 0.057(3) -0.013(2) -0.0015(19) -0.003(2) C5 0.040(2) 0.036(2) 0.0385(19) -0.0081(16) 0.0016(16) -0.0011(18) C7 0.050(2) 0.0140(15) 0.0186(14) 0.0020(12) 0.0034(14) -0.0031(15) C8 0.041(2) 0.0251(18) 0.0315(17) 0.0004(14) -0.0039(15) 0.0069(16) C9 0.038(2) 0.036(2) 0.0301(17) -0.0025(15) 0.0007(15) -0.0001(17) C10 0.044(3) 0.057(3) 0.071(3) -0.001(2) 0.007(2) 0.004(2) C11 0.046(3) 0.079(4) 0.078(3) -0.003(3) 0.011(2) -0.018(3) C12 0.058(3) 0.050(3) 0.060(3) -0.001(2) 0.010(2) -0.022(2) C13 0.050(2) 0.034(2) 0.0327(19) -0.0011(15) 0.0091(16) -0.0108(18) C14 0.053(2) 0.0164(15) 0.0169(15) -0.0041(12) 0.0090(14) 0.0014(15) C15 0.048(2) 0.0166(15) 0.0158(14) -0.0021(12) 0.0059(13) -0.0036(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 O3 1.8843(19) . ? Ga1 O1 1.976(2) . ? Ga1 O3 1.9822(19) 3_566 ? Ga1 N2 2.061(3) . ? Ga1 N1 2.062(3) . ? Ga1 N3 2.086(2) . ? O1 C15 1.277(4) . ? O3 Ga1 1.9822(19) 3_566 ? N2 C9 1.341(5) . ? N2 C13 1.344(4) . ? N1 C5 1.336(5) . ? N1 C1 1.353(4) . ? N3 C14 1.486(3) . ? N3 C8 1.493(4) . ? N3 C7 1.493(4) . ? O6 N4 1.123(7) . ? O4 N4 1.195(6) . ? O5 N4 1.164(7) . ? O2 C15 1.224(3) . ? C1 C2 1.368(5) . ? C1 C7 1.495(5) . ? C2 C3 1.368(6) . ? C3 C4 1.387(7) . ? C4 C5 1.369(5) . ? C8 C9 1.498(5) . ? C9 C10 1.380(6) . ? C10 C11 1.366(7) . ? C11 C12 1.366(7) . ? C12 C13 1.372(6) . ? C14 C15 1.513(4) . ? 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 99.22(8) . . ? O3 Ga1 O3 79.12(9) . 3_566 ? O1 Ga1 O3 178.19(9) . 3_566 ? O3 Ga1 N2 101.08(11) . . ? O1 Ga1 N2 88.97(10) . . ? O3 Ga1 N2 92.07(10) 3_566 . ? O3 Ga1 N1 99.57(11) . . ? O1 Ga1 N1 85.76(10) . . ? O3 Ga1 N1 93.78(9) 3_566 . ? N2 Ga1 N1 159.25(11) . . ? O3 Ga1 N3 175.60(8) . . ? O1 Ga1 N3 85.16(9) . . ? O3 Ga1 N3 96.50(8) 3_566 . ? N2 Ga1 N3 79.36(11) . . ? N1 Ga1 N3 80.20(11) . . ? C15 O1 Ga1 114.64(19) . . ? Ga1 O3 Ga1 100.88(9) . 3_566 ? C9 N2 C13 119.8(3) . . ? C9 N2 Ga1 114.1(2) . . ? C13 N2 Ga1 125.8(3) . . ? C5 N1 C1 119.8(3) . . ? C5 N1 Ga1 125.3(2) . . ? C1 N1 Ga1 114.4(2) . . ? C14 N3 C8 112.0(3) . . ? C14 N3 C7 111.1(2) . . ? C8 N3 C7 113.8(2) . . ? C14 N3 Ga1 106.32(18) . . ? C8 N3 Ga1 106.46(19) . . ? C7 N3 Ga1 106.60(19) . . ? O6 N4 O5 117.1(8) . . ? O6 N4 O4 122.5(7) . . ? O5 N4 O4 119.7(7) . . ? N1 C1 C2 120.9(3) . . ? N1 C1 C7 115.0(3) . . ? C2 C1 C7 124.2(3) . . ? C3 C2 C1 119.5(4) . . ? C2 C3 C4 119.7(4) . . ? C5 C4 C3 118.5(4) . . ? N1 C5 C4 121.7(4) . . ? N3 C7 C1 109.3(3) . . ? N3 C8 C9 107.4(3) . . ? N2 C9 C10 120.3(4) . . ? N2 C9 C8 115.8(3) . . ? C10 C9 C8 123.9(4) . . ? C11 C10 C9 119.7(5) . . ? C10 C11 C12 119.9(5) . . ? C11 C12 C13 118.7(4) . . ? N2 C13 C12 121.7(4) . . ? N3 C14 C15 113.7(2) . . ? O2 C15 O1 123.5(3) . . ? O2 C15 C14 118.0(3) . . ? O1 C15 C14 118.5(3) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.129 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.092