# Copyright The Royal Society of Chemistry, 1998 # CCDC Number: 186/1165 data_LH9707 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H18 N2 O8 Mn' _chemical_formula_weight 349.20 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' -0.5299 2.8052 '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 8.510(2) _cell_length_b 11.981(2) _cell_length_c 8.157(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.57(2) _cell_angle_gamma 90.00 _cell_volume 768.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 12.15 _cell_measurement_theta_max 25.67 _exptl_crystal_description needles _exptl_crystal_colour Clear _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method ? _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 7.367 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.4915 _exptl_absorpt_correction_T_max 0.6557 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5.91 _diffrn_reflns_number 1233 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0723 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 5.63 _diffrn_reflns_theta_max 60.01 _reflns_number_total 1143 _reflns_number_observed 864 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.1649P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0042(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1143 _refine_ls_number_parameters 106 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_obs 0.0498 _refine_ls_wR_factor_all 0.1276 _refine_ls_wR_factor_obs 0.1136 _refine_ls_goodness_of_fit_all 1.038 _refine_ls_goodness_of_fit_obs 1.078 _refine_ls_restrained_S_all 1.037 _refine_ls_restrained_S_obs 1.077 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn Mn 1.0000 0.0000 1.0000 0.0215(3) Uani 1 d S . O1 O 0.9955(5) 0.0751(3) 0.7554(5) 0.0352(9) Uani 1 d . . C2 C 0.9970(6) 0.0328(4) 0.6158(6) 0.0258(10) Uani 1 d . . C3 C 0.9564(7) -0.0753(4) 0.5274(6) 0.0277(11) Uani 1 d . . O4 O 0.9022(6) -0.1663(3) 0.5599(5) 0.0464(11) Uani 1 d . . O5 O 0.7598(5) 0.0840(3) 0.9709(6) 0.0470(10) Uani 1 d . . C6 C 0.7295(8) 0.1836(5) 0.9760(11) 0.058(2) Uani 1 d . . H6A H 0.8197(8) 0.2328(5) 0.9972(11) 0.069 Uiso 1 calc R . N7 N 0.5823(6) 0.2267(4) 0.9544(7) 0.0505(13) Uani 1 d . . C8 C 0.4368(9) 0.1562(7) 0.9172(13) 0.080(3) Uani 1 d . . H8A H 0.3437(9) 0.1891(7) 0.8183(13) 0.121 Uiso 1 d R . H8B H 0.4058(9) 0.1512(7) 1.0206(13) 0.121 Uiso 1 d R . H8C H 0.4602(9) 0.0823(7) 0.8840(13) 0.121 Uiso 1 d R . C9 C 0.5598(11) 0.3473(7) 0.9655(14) 0.101(4) Uani 1 d . . H9A H 0.4872(11) 0.3628(7) 1.0307(14) 0.152 Uiso 1 d R . H9B H 0.5074(11) 0.3762(7) 0.8449(14) 0.152 Uiso 1 d R . H9C H 0.6695(11) 0.3826(7) 1.0253(14) 0.152 Uiso 1 d R . O10 O 0.8599(5) -0.1458(3) 0.8661(4) 0.0306(8) Uani 1 d D . H10B H 0.8771(99) -0.2118(30) 0.9230(88) 0.078(25) Uiso 1 d D . H10A H 0.8843(75) -0.1653(52) 0.7720(51) 0.052(19) Uiso 1 d 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 Mn 0.0283(5) 0.0222(5) 0.0176(5) 0.0004(5) 0.0128(4) 0.0011(5) O1 0.064(2) 0.027(2) 0.022(2) -0.006(2) 0.025(2) -0.008(2) C2 0.041(3) 0.019(2) 0.020(2) 0.000(2) 0.015(2) -0.002(2) C3 0.049(3) 0.021(2) 0.020(2) 0.000(2) 0.020(2) 0.000(2) O4 0.096(3) 0.027(2) 0.033(2) -0.006(2) 0.044(2) -0.018(2) O5 0.036(2) 0.042(2) 0.071(3) 0.002(2) 0.028(2) 0.013(2) C6 0.035(3) 0.039(3) 0.099(6) -0.005(3) 0.025(3) 0.000(3) N7 0.038(3) 0.048(3) 0.060(3) -0.005(3) 0.012(2) 0.016(2) C8 0.047(4) 0.072(5) 0.138(8) 0.036(5) 0.052(5) 0.018(4) C9 0.062(5) 0.064(5) 0.139(9) -0.033(6) -0.004(5) 0.032(4) O10 0.047(2) 0.025(2) 0.024(2) -0.0001(15) 0.018(2) -0.004(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 Mn O10 2.160(3) 3_757 ? Mn O10 2.160(3) . ? Mn O1 2.176(3) . ? Mn O1 2.176(3) 3_757 ? Mn O5 2.208(4) 3_757 ? Mn O5 2.208(4) . ? O1 C2 1.251(6) . ? C2 C3 1.458(6) . ? C2 C3 1.462(6) 3_756 ? C3 O4 1.251(6) . ? C3 C2 1.462(6) 3_756 ? O5 C6 1.225(7) . ? C6 N7 1.303(7) . ? N7 C8 1.432(9) . ? N7 C9 1.465(9) . ? 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 O10 Mn O10 180.0 3_757 . ? O10 Mn O1 86.62(13) 3_757 . ? O10 Mn O1 93.38(13) . . ? O10 Mn O1 93.38(13) 3_757 3_757 ? O10 Mn O1 86.62(13) . 3_757 ? O1 Mn O1 180.0 . 3_757 ? O10 Mn O5 90.32(15) 3_757 3_757 ? O10 Mn O5 89.68(15) . 3_757 ? O1 Mn O5 88.7(2) . 3_757 ? O1 Mn O5 91.3(2) 3_757 3_757 ? O10 Mn O5 89.68(15) 3_757 . ? O10 Mn O5 90.32(15) . . ? O1 Mn O5 91.3(2) . . ? O1 Mn O5 88.7(2) 3_757 . ? O5 Mn O5 180.0 3_757 . ? C2 O1 Mn 131.6(3) . . ? O1 C2 C3 136.7(5) . . ? O1 C2 C3 133.3(4) . 3_756 ? C3 C2 C3 90.0(4) . 3_756 ? O4 C3 C2 134.9(4) . . ? O4 C3 C2 135.1(5) . 3_756 ? C2 C3 C2 90.0(4) . 3_756 ? C6 O5 Mn 129.7(4) . . ? O5 C6 N7 125.8(6) . . ? C6 N7 C8 120.2(6) . . ? C6 N7 C9 121.6(6) . . ? C8 N7 C9 118.1(6) . . ? _refine_diff_density_max 0.300 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.080 #=END data_l9803 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H18 Mn N2 O8' _chemical_formula_weight 349.20 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Mn' 'Mn' -0.5299 2.8052 '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 8.4991(4) _cell_length_b 11.9831(4) _cell_length_c 8.1392(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.347(3) _cell_angle_gamma 90.00 _cell_volume 761.07(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 22 _cell_measurement_theta_min 5.67 _cell_measurement_theta_max 36.45 _exptl_crystal_description rhombs _exptl_crystal_colour Clear _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method ? _exptl_crystal_F_000 362 _exptl_absorpt_coefficient_mu 7.434 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2866 _exptl_absorpt_correction_T_max 0.7407 _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1227 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.67 _diffrn_reflns_theta_max 59.98 _reflns_number_total 1137 _reflns_number_observed 963 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 57 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.2878P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0908(52) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1080 _refine_ls_number_parameters 106 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_obs 0.0442 _refine_ls_wR_factor_all 0.1175 _refine_ls_wR_factor_obs 0.1093 _refine_ls_goodness_of_fit_all 1.046 _refine_ls_goodness_of_fit_obs 1.073 _refine_ls_restrained_S_all 1.052 _refine_ls_restrained_S_obs 1.072 _refine_ls_shift/esd_max 0.010 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Mn Mn 1.0000 0.0000 1.0000 0.0169(4) Uani 1 d S . O1 O 0.9923(4) 0.0755(2) 0.7547(4) 0.0266(7) Uani 1 d . . C2 C 0.9967(5) 0.0321(3) 0.6153(5) 0.0214(9) Uani 1 d . . C3 C 0.9576(5) -0.0750(3) 0.5267(5) 0.0212(9) Uani 1 d . . O4 O 0.9045(4) -0.1670(2) 0.5604(4) 0.0365(8) Uani 1 d . . O5 O 0.7590(4) 0.0839(2) 0.9718(4) 0.0364(8) Uani 1 d . . C6 C 0.7304(6) 0.1834(4) 0.9807(7) 0.0442(13) Uani 1 d . . H6A H 0.8223(6) 0.2331(4) 1.0039(7) 0.053 Uiso 1 calc R . N7 N 0.5809(5) 0.2264(3) 0.9603(5) 0.0398(10) Uani 1 d . . C8 C 0.4360(7) 0.1562(5) 0.9246(10) 0.074(2) Uani 1 d . . H8A H 0.3430(7) 0.1890(5) 0.8258(10) 0.112 Uiso 1 d R . H8B H 0.4051(7) 0.1512(5) 1.0281(10) 0.112 Uiso 1 d R . H8C H 0.4595(7) 0.0823(5) 0.8915(10) 0.112 Uiso 1 d R . C9 C 0.5583(8) 0.3460(5) 0.9738(10) 0.085(3) Uani 1 d . . H9A H 0.4857(8) 0.3615(5) 1.0391(10) 0.128 Uiso 1 d R . H9B H 0.5059(8) 0.3748(5) 0.8533(10) 0.128 Uiso 1 d R . H9C H 0.6680(8) 0.3813(5) 1.0336(10) 0.128 Uiso 1 d R . O10 O 0.8576(3) -0.1455(2) 0.8640(3) 0.0237(7) Uani 1 d D . H10B H 0.8672(70) -0.2115(22) 0.9201(63) 0.054(16) Uiso 1 d D . H10A H 0.8747(59) -0.1573(43) 0.7631(35) 0.047(15) Uiso 1 d 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 Mn 0.0236(5) 0.0189(5) 0.0142(5) 0.0005(3) 0.0140(3) 0.0006(3) O1 0.046(2) 0.0221(14) 0.0206(14) -0.0017(12) 0.0227(13) -0.0022(12) C2 0.031(2) 0.019(2) 0.018(2) -0.001(2) 0.014(2) 0.001(2) C3 0.035(2) 0.018(2) 0.019(2) 0.003(2) 0.020(2) -0.001(2) O4 0.074(2) 0.023(2) 0.028(2) -0.0054(13) 0.037(2) -0.0144(15) O5 0.032(2) 0.030(2) 0.055(2) 0.0004(15) 0.0266(15) 0.0074(13) C6 0.025(2) 0.038(3) 0.067(4) -0.003(2) 0.016(2) 0.005(2) N7 0.031(2) 0.040(2) 0.045(2) -0.006(2) 0.011(2) 0.013(2) C8 0.047(3) 0.069(4) 0.130(6) 0.049(4) 0.060(4) 0.023(3) C9 0.049(3) 0.058(4) 0.112(6) -0.036(4) -0.008(4) 0.024(3) O10 0.038(2) 0.0229(15) 0.0159(14) -0.0002(12) 0.0164(12) -0.0023(12) _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 Mn O10 2.161(3) 3_757 ? Mn O10 2.161(3) . ? Mn O1 2.169(3) . ? Mn O1 2.169(3) 3_757 ? Mn O5 2.210(3) 3_757 ? Mn O5 2.210(3) . ? O1 C2 1.262(5) . ? C2 C3 1.445(5) . ? C2 C3 1.452(5) 3_756 ? C3 O4 1.262(5) . ? C3 C2 1.452(5) 3_756 ? O5 C6 1.225(5) . ? C6 N7 1.319(6) . ? N7 C8 1.423(7) . ? N7 C9 1.455(7) . ? 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 O10 Mn O10 180.0 3_757 . ? O10 Mn O1 86.63(10) 3_757 . ? O10 Mn O1 93.37(10) . . ? O10 Mn O1 93.37(10) 3_757 3_757 ? O10 Mn O1 86.63(10) . 3_757 ? O1 Mn O1 180.0 . 3_757 ? O10 Mn O5 90.33(11) 3_757 3_757 ? O10 Mn O5 89.67(11) . 3_757 ? O1 Mn O5 88.50(11) . 3_757 ? O1 Mn O5 91.50(11) 3_757 3_757 ? O10 Mn O5 89.67(11) 3_757 . ? O10 Mn O5 90.33(11) . . ? O1 Mn O5 91.50(11) . . ? O1 Mn O5 88.50(11) 3_757 . ? O5 Mn O5 180.0 3_757 . ? C2 O1 Mn 130.9(2) . . ? O1 C2 C3 137.0(4) . . ? O1 C2 C3 133.1(4) . 3_756 ? C3 C2 C3 89.9(3) . 3_756 ? O4 C3 C2 134.4(4) . . ? O4 C3 C2 135.5(4) . 3_756 ? C2 C3 C2 90.1(3) . 3_756 ? C6 O5 Mn 129.3(3) . . ? O5 C6 N7 125.2(5) . . ? C6 N7 C8 120.4(4) . . ? C6 N7 C9 121.6(5) . . ? C8 N7 C9 117.9(4) . . ? _refine_diff_density_max 0.336 _refine_diff_density_min -0.808 _refine_diff_density_rms 0.083 data_LH9705 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H18 N2 O8 Ni' _chemical_formula_weight 352.97 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Ni' 'Ni' -3.0029 0.5091 '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 8.3659(4) _cell_length_b 11.9298(15) _cell_length_c 7.9281(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.242(4) _cell_angle_gamma 90.00 _cell_volume 732.38(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 9.39 _cell_measurement_theta_max 24.84 _exptl_crystal_description plates _exptl_crystal_colour 'Very pale blue' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.601 _exptl_crystal_density_method ? _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 2.307 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 7.99 _diffrn_reflns_number 1167 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 5.71 _diffrn_reflns_theta_max 59.99 _reflns_number_total 1080 _reflns_number_observed 1023 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 19 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R- factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0312P)^2^+0.9426P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0021(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1061 _refine_ls_number_parameters 106 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_obs 0.0358 _refine_ls_wR_factor_all 0.0933 _refine_ls_wR_factor_obs 0.0904 _refine_ls_goodness_of_fit_all 1.078 _refine_ls_goodness_of_fit_obs 1.086 _refine_ls_restrained_S_all 1.094 _refine_ls_restrained_S_obs 1.085 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Ni Ni 1.0000 0.0000 1.0000 0.0166(3) Uani 1 d S . O1 O 0.9950(3) 0.07499(15) 0.7636(2) 0.0251(5) Uani 1 d . . C2 C 0.9980(3) 0.0327(2) 0.6201(3) 0.0195(6) Uani 1 d . . C3 C 0.9618(4) -0.0766(2) 0.5307(3) 0.0216(6) Uani 1 d . . O4 O 0.9143(3) -0.1700(2) 0.5683(3) 0.0375(6) Uani 1 d . . O5 O 0.7667(3) 0.0768(2) 0.9717(3) 0.0335(5) Uani 1 d . . C6 C 0.7376(4) 0.1772(3) 0.9733(5) 0.0395(8) Uani 1 d . . H6A H 0.8305(4) 0.2259(3) 0.9975(5) 0.047 Uiso 1 calc R . N7 N 0.5856(3) 0.2218(2) 0.9435(4) 0.0393(7) Uani 1 d . . C8 C 0.4355(5) 0.1523(4) 0.9019(7) 0.0708(14) Uani 1 d . . H8A H 0.3425(5) 0.1852(4) 0.8031(7) 0.106 Uiso 1 d R . H8B H 0.4045(5) 0.1474(4) 1.0054(7) 0.106 Uiso 1 d R . H8C H 0.4589(5) 0.0785(4) 0.8688(7) 0.106 Uiso 1 d R . C9 C 0.5625(5) 0.3429(3) 0.9533(7) 0.080(2) Uani 1 d . . H9A H 0.4899(5) 0.3584(3) 1.0185(7) 0.120 Uiso 1 d R . H9B H 0.5101(5) 0.3718(3) 0.8328(7) 0.120 Uiso 1 d R . H9C H 0.6722(5) 0.3782(3) 1.0131(7) 0.120 Uiso 1 d R . O10 O 0.8602(2) -0.1370(2) 0.8719(2) 0.0219(4) Uani 1 d D . H10B H 0.8746(43) -0.1968(17) 0.9453(37) 0.041(10) Uiso 1 d D . H10A H 0.8806(42) -0.1557(29) 0.7719(27) 0.046(10) Uiso 1 d 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 Ni 0.0211(4) 0.0161(4) 0.0147(4) -0.0001(2) 0.0092(3) 0.0006(2) O1 0.0447(12) 0.0182(10) 0.0169(9) -0.0029(8) 0.0168(8) -0.0029(8) C2 0.0267(14) 0.0147(13) 0.0182(14) -0.0001(11) 0.0097(11) 0.0013(12) C3 0.0345(15) 0.0168(13) 0.0160(13) 0.0002(11) 0.0122(11) -0.0017(12) O4 0.080(2) 0.0166(10) 0.0303(11) -0.0053(9) 0.0369(11) -0.0147(10) O5 0.0291(11) 0.0269(12) 0.0485(13) 0.0021(10) 0.0192(10) 0.0044(9) C6 0.023(2) 0.034(2) 0.056(2) 0.000(2) 0.0091(14) 0.0026(14) N7 0.0276(14) 0.0349(15) 0.051(2) -0.0039(13) 0.0099(12) 0.0102(11) C8 0.037(2) 0.060(3) 0.124(4) 0.030(3) 0.039(2) 0.014(2) C9 0.054(3) 0.042(2) 0.110(4) -0.023(2) -0.008(2) 0.022(2) O10 0.0307(10) 0.0201(10) 0.0173(10) 0.0010(8) 0.0118(8) -0.0025(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ni O10 2.042(2) 3_757 ? Ni O10 2.042(2) . ? Ni O1 2.063(2) . ? Ni O1 2.063(2) 3_757 ? Ni O5 2.090(2) . ? Ni O5 2.090(2) 3_757 ? O1 C2 1.253(3) . ? C2 C3 1.457(4) 3_756 ? C2 C3 1.459(4) . ? C3 O4 1.256(3) . ? C3 C2 1.457(4) 3_756 ? O5 C6 1.224(4) . ? C6 N7 1.315(4) . ? N7 C8 1.435(5) . ? N7 C9 1.463(5) . ? 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 O10 Ni O10 180.0 3_757 . ? O10 Ni O1 85.16(7) 3_757 . ? O10 Ni O1 94.84(7) . . ? O10 Ni O1 94.84(7) 3_757 3_757 ? O10 Ni O1 85.16(7) . 3_757 ? O1 Ni O1 180.0 . 3_757 ? O10 Ni O5 92.22(8) 3_757 . ? O10 Ni O5 87.78(8) . . ? O1 Ni O5 90.89(8) . . ? O1 Ni O5 89.11(8) 3_757 . ? O10 Ni O5 87.78(8) 3_757 3_757 ? O10 Ni O5 92.22(8) . 3_757 ? O1 Ni O5 89.11(8) . 3_757 ? O1 Ni O5 90.89(8) 3_757 3_757 ? O5 Ni O5 180.0 . 3_757 ? C2 O1 Ni 130.5(2) . . ? O1 C2 C3 133.7(2) . 3_756 ? O1 C2 C3 136.8(2) . . ? C3 C2 C3 89.6(2) 3_756 . ? O4 C3 C2 134.9(2) . 3_756 ? O4 C3 C2 134.7(2) . . ? C2 C3 C2 90.4(2) 3_756 . ? C6 O5 Ni 127.5(2) . . ? O5 C6 N7 125.2(3) . . ? C6 N7 C8 120.7(3) . . ? C6 N7 C9 121.9(3) . . ? C8 N7 C9 117.4(3) . . ? _refine_diff_density_max 0.258 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.064 #=END data_LH9704 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H18 N2 O8 Co' _chemical_formula_weight 353.19 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Co' 'Co' -2.3653 3.6143 '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 8.4130(4) _cell_length_b 11.9029(5) _cell_length_c 8.0070(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.268(4) _cell_angle_gamma 90.00 _cell_volume 742.02(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 43 _cell_measurement_theta_min 7.50 _cell_measurement_theta_max 32.82 _exptl_crystal_description 'Square plates' _exptl_crystal_colour Pink _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method ? _exptl_crystal_F_000 366 _exptl_absorpt_coefficient_mu 9.458 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.4165 _exptl_absorpt_correction_T_max 0.7772 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 4.30 _diffrn_reflns_number 1107 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_sigmaI/netI 0.0687 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 5.68 _diffrn_reflns_theta_max 59.95 _reflns_number_total 1026 _reflns_number_observed 774 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 9 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+1.3032P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0023(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1017 _refine_ls_number_parameters 106 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_obs 0.0520 _refine_ls_wR_factor_all 0.1285 _refine_ls_wR_factor_obs 0.1134 _refine_ls_goodness_of_fit_all 1.042 _refine_ls_goodness_of_fit_obs 1.098 _refine_ls_restrained_S_all 1.082 _refine_ls_restrained_S_obs 1.096 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Co Co 1.0000 0.0000 1.0000 0.0220(4) Uani 1 d S . O1 O 0.9952(6) 0.0764(3) 0.7602(5) 0.0329(10) Uani 1 d . . C2 C 0.9987(7) 0.0337(4) 0.6186(7) 0.0248(12) Uani 1 d . . C3 C 0.9589(8) -0.0764(4) 0.5286(7) 0.0287(12) Uani 1 d . . O4 O 0.9074(7) -0.1686(3) 0.5652(6) 0.0464(12) Uani 1 d . . O5 O 0.7644(6) 0.0795(3) 0.9728(6) 0.0439(11) Uani 1 d . . C6 C 0.7333(9) 0.1795(6) 0.9737(10) 0.053(2) Uani 1 d . . H6A H 0.8251(9) 0.2285(6) 0.9958(10) 0.064 Uiso 1 calc R . N7 N 0.5859(7) 0.2245(4) 0.9473(8) 0.0474(14) Uani 1 d . . C8 C 0.4348(10) 0.1549(7) 0.9055(14) 0.080(3) Uani 1 d . . H8A H 0.3418(10) 0.1877(7) 0.8067(14) 0.120 Uiso 1 d R . H8B H 0.4038(10) 0.1499(7) 1.0090(14) 0.120 Uiso 1 d R . H8C H 0.4582(10) 0.0810(7) 0.8724(14) 0.120 Uiso 1 d R . C9 C 0.5610(11) 0.3460(6) 0.9541(14) 0.093(4) Uani 1 d . . H9A H 0.4884(11) 0.3616(6) 1.0193(14) 0.139 Uiso 1 d R . H9B H 0.5086(11) 0.3749(6) 0.8336(14) 0.139 Uiso 1 d R . H9C H 0.6707(11) 0.3813(6) 1.0139(14) 0.139 Uiso 1 d R . O10 O 0.8618(5) -0.1397(3) 0.8720(5) 0.0292(9) Uani 1 d D . H10B H 0.8959(67) -0.2010(25) 0.9424(56) 0.023(14) Uiso 1 d D . H10A H 0.8886(65) -0.1521(42) 0.7749(43) 0.021(14) Uiso 1 d 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 Co 0.0275(6) 0.0197(6) 0.0204(6) -0.0004(6) 0.0107(5) 0.0004(6) O1 0.055(3) 0.021(2) 0.026(2) -0.001(2) 0.020(2) -0.002(2) C2 0.034(3) 0.020(3) 0.022(3) 0.000(2) 0.012(2) -0.002(2) C3 0.042(3) 0.020(2) 0.027(3) -0.002(2) 0.017(3) -0.001(2) O4 0.091(4) 0.025(2) 0.038(2) -0.006(2) 0.040(3) -0.014(2) O5 0.041(3) 0.035(2) 0.059(3) 0.005(2) 0.022(2) 0.006(2) C6 0.038(4) 0.041(4) 0.072(5) 0.001(4) 0.013(4) -0.002(3) N7 0.033(3) 0.038(3) 0.063(4) -0.005(3) 0.009(3) 0.012(3) C8 0.044(5) 0.073(5) 0.131(8) 0.028(6) 0.042(5) 0.012(4) C9 0.053(5) 0.046(4) 0.137(9) -0.022(5) -0.011(5) 0.023(4) O10 0.041(2) 0.024(2) 0.027(2) 0.003(2) 0.018(2) 0.000(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 Co O10 2.064(4) 3_757 ? Co O10 2.064(4) . ? Co O1 2.111(3) . ? Co O1 2.111(3) 3_757 ? Co O5 2.131(4) 3_757 ? Co O5 2.131(4) . ? O1 C2 1.253(6) . ? C2 C3 1.447(7) 3_756 ? C2 C3 1.472(7) . ? C3 O4 1.254(6) . ? C3 C2 1.447(7) 3_756 ? O5 C6 1.220(7) . ? C6 N7 1.292(8) . ? N7 C8 1.446(10) . ? N7 C9 1.466(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O10 Co O10 180.0 3_757 . ? O10 Co O1 85.28(14) 3_757 . ? O10 Co O1 94.72(14) . . ? O10 Co O1 94.72(14) 3_757 3_757 ? O10 Co O1 85.28(14) . 3_757 ? O1 Co O1 180.000(1) . 3_757 ? O10 Co O5 88.8(2) 3_757 3_757 ? O10 Co O5 91.2(2) . 3_757 ? O1 Co O5 88.9(2) . 3_757 ? O1 Co O5 91.1(2) 3_757 3_757 ? O10 Co O5 91.2(2) 3_757 . ? O10 Co O5 88.8(2) . . ? O1 Co O5 91.1(2) . . ? O1 Co O5 88.9(2) 3_757 . ? O5 Co O5 180.0 3_757 . ? C2 O1 Co 130.5(3) . . ? O1 C2 C3 133.8(5) . 3_756 ? O1 C2 C3 136.5(5) . . ? C3 C2 C3 89.7(4) 3_756 . ? O4 C3 C2 135.3(5) . 3_756 ? O4 C3 C2 134.4(5) . . ? C2 C3 C2 90.3(4) 3_756 . ? C6 O5 Co 128.8(5) . . ? O5 C6 N7 126.7(7) . . ? C6 N7 C8 120.4(6) . . ? C6 N7 C9 122.9(7) . . ? C8 N7 C9 116.7(6) . . ? _refine_diff_density_max 0.433 _refine_diff_density_min -0.569 _refine_diff_density_rms 0.076 #=END data_LH9609 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H18 N2 O8 Cu' _chemical_formula_weight 357.80 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.6319(11) _cell_length_b 7.7182(12) _cell_length_c 11.220(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.414(11) _cell_angle_gamma 90.00 _cell_volume 717.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 5.74 _cell_measurement_theta_max 25.62 _exptl_crystal_description 'Platy needles' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method ? _exptl_crystal_F_000 370 _exptl_absorpt_coefficient_mu 2.555 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.41 _diffrn_reflns_number 1049 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.75 _diffrn_reflns_theta_max 57.20 _reflns_number_total 977 _reflns_number_observed 907 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.6117P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0034(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 977 _refine_ls_number_parameters 106 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_obs 0.0342 _refine_ls_wR_factor_all 0.0980 _refine_ls_wR_factor_obs 0.0943 _refine_ls_goodness_of_fit_all 1.081 _refine_ls_goodness_of_fit_obs 1.084 _refine_ls_restrained_S_all 1.079 _refine_ls_restrained_S_obs 1.083 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu Cu 0.0000 0.0000 0.0000 0.0105(3) Uani 1 d S . O1 O 0.0951(2) 0.2276(2) 0.0601(2) 0.0140(5) Uani 1 d . . C2 C 0.0413(3) 0.3756(4) 0.0257(2) 0.0120(6) Uani 1 d . . C3 C -0.0768(3) 0.4530(4) -0.0826(3) 0.0125(6) Uani 1 d . . O4 O -0.1667(2) 0.3954(2) -0.1822(2) 0.0191(5) Uani 1 d . . O5 O -0.2481(2) 0.1218(3) 0.0215(2) 0.0247(6) Uani 1 d . . C6 C -0.3706(4) 0.1493(4) -0.0652(3) 0.0207(7) Uani 1 d . . H6A H -0.3604(4) 0.1268(4) -0.1404(3) 0.025 Uiso 1 d R . N7 N -0.5043(3) 0.2231(3) -0.0546(2) 0.0209(6) Uani 1 d . . C8 C -0.5182(4) 0.2768(5) 0.0663(3) 0.0287(8) Uani 1 d . . H8C H -0.5394(4) 0.4003(5) 0.0653(3) 0.043 Uiso 1 d R . H8B H -0.4181(4) 0.2515(5) 0.1295(3) 0.043 Uiso 1 d R . H8A H -0.6062(4) 0.2145(5) 0.0848(3) 0.043 Uiso 1 d R . C9 C -0.6459(4) 0.2446(5) -0.1619(3) 0.0331(9) Uani 1 d . . H9C H -0.6804(4) 0.3647(5) -0.1677(3) 0.050 Uiso 1 d R . H9B H -0.7327(4) 0.1712(5) -0.1521(3) 0.050 Uiso 1 d R . H9A H -0.6185(4) 0.2122(5) -0.2370(3) 0.050 Uiso 1 d R . O10 O 0.0673(2) -0.0678(3) 0.1767(2) 0.0137(5) Uani 1 d D . H10A H 0.1039(40) -0.1774(16) 0.1885(32) 0.028(9) Uiso 1 d D . H10B H 0.1432(33) 0.0048(37) 0.2215(34) 0.041(13) Uiso 1 d 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 Cu 0.0120(4) 0.0078(4) 0.0090(4) 0.0005(2) -0.0014(3) -0.0004(2) O1 0.0129(10) 0.0086(10) 0.0150(10) 0.0009(8) -0.0048(8) 0.0009(8) C2 0.0085(13) 0.014(2) 0.0109(14) 0.0005(12) -0.0015(11) -0.0011(13) C3 0.0089(14) 0.0151(14) 0.012(2) 0.0009(13) -0.0004(12) -0.0005(12) O4 0.0235(11) 0.0115(10) 0.0132(11) -0.0010(8) -0.0095(9) 0.0001(9) O5 0.0154(12) 0.0344(13) 0.0222(12) 0.0004(10) 0.0019(10) 0.0020(9) C6 0.021(2) 0.024(2) 0.018(2) -0.0035(13) 0.0082(14) -0.0065(14) N7 0.0139(13) 0.029(2) 0.0169(13) -0.0007(12) 0.0006(10) -0.0014(11) C8 0.020(2) 0.042(2) 0.024(2) -0.006(2) 0.0063(14) 0.002(2) C9 0.020(2) 0.047(2) 0.027(2) 0.005(2) -0.0038(15) -0.0004(15) O10 0.0159(11) 0.0108(11) 0.0120(10) -0.0002(8) 0.0002(8) -0.0021(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 Cu O10 1.973(2) 3 ? Cu O10 1.973(2) . ? Cu O1 1.975(2) 3 ? Cu O1 1.975(2) . ? Cu O5 2.413(2) . ? Cu O5 2.413(2) 3 ? O1 C2 1.253(3) . ? C2 C3 1.463(4) 3_565 ? C2 C3 1.473(4) . ? C3 O4 1.249(3) . ? C3 C2 1.463(4) 3_565 ? O5 C6 1.236(4) . ? C6 N7 1.323(4) . ? N7 C8 1.456(4) . ? N7 C9 1.462(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 O10 Cu O10 180.0 3 . ? O10 Cu O1 85.21(8) 3 3 ? O10 Cu O1 94.79(8) . 3 ? O10 Cu O1 94.79(8) 3 . ? O10 Cu O1 85.21(8) . . ? O1 Cu O1 180.0 3 . ? O10 Cu O5 88.84(7) 3 . ? O10 Cu O5 91.16(7) . . ? O1 Cu O5 94.93(7) 3 . ? O1 Cu O5 85.07(7) . . ? O10 Cu O5 91.16(7) 3 3 ? O10 Cu O5 88.84(7) . 3 ? O1 Cu O5 85.07(8) 3 3 ? O1 Cu O5 94.93(7) . 3 ? O5 Cu O5 180.0 . 3 ? C2 O1 Cu 128.6(2) . . ? O1 C2 C3 132.6(2) . 3_565 ? O1 C2 C3 137.2(3) . . ? C3 C2 C3 90.2(2) 3_565 . ? O4 C3 C2 135.5(3) . 3_565 ? O4 C3 C2 134.7(3) . . ? C2 C3 C2 89.8(2) 3_565 . ? C6 O5 Cu 125.0(2) . . ? O5 C6 N7 125.3(3) . . ? C6 N7 C8 120.6(3) . . ? C6 N7 C9 121.5(3) . . ? C8 N7 C9 117.7(3) . . ? _refine_diff_density_max 0.317 _refine_diff_density_min -0.776 _refine_diff_density_rms 0.080 #=END data_LH9610 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C10 H18 N2 O8 Zn' _chemical_formula_weight 359.63 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Zn' 'Zn' -1.5491 0.6778 '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 8.4436(13) _cell_length_b 11.9088(4) _cell_length_c 7.9992(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.512(9) _cell_angle_gamma 90.00 _cell_volume 743.05(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16 _cell_measurement_theta_min 12.28 _cell_measurement_theta_max 19.89 _exptl_crystal_description Needles _exptl_crystal_colour Clear _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method ? _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.686 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.6931 _exptl_absorpt_correction_T_max 0.9231 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.01 _diffrn_reflns_number 1196 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 5.67 _diffrn_reflns_theta_max 59.99 _reflns_number_total 1107 _reflns_number_observed 1037 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.8512P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0067(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1107 _refine_ls_number_parameters 106 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_obs 0.0444 _refine_ls_wR_factor_all 0.1180 _refine_ls_wR_factor_obs 0.1155 _refine_ls_goodness_of_fit_all 1.087 _refine_ls_goodness_of_fit_obs 1.103 _refine_ls_restrained_S_all 1.085 _refine_ls_restrained_S_obs 1.102 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Zn Zn 1.0000 0.0000 1.0000 0.0193(3) Uani 1 d S . O1 O 0.9937(3) 0.0759(2) 0.7601(3) 0.0275(6) Uani 1 d . . C2 C 0.9973(4) 0.0335(3) 0.6189(4) 0.0208(7) Uani 1 d . . C3 C 0.9609(4) -0.0763(3) 0.5302(4) 0.0229(7) Uani 1 d . . O4 O 0.9121(4) -0.1693(2) 0.5669(3) 0.0398(7) Uani 1 d . . O5 O 0.7616(3) 0.0790(2) 0.9705(4) 0.0390(7) Uani 1 d . . C6 C 0.7326(5) 0.1799(4) 0.9753(6) 0.0442(10) Uani 1 d . . H6A H 0.8250(5) 0.2287(4) 1.0016(6) 0.053 Uiso 1 calc R . N7 N 0.5824(4) 0.2244(3) 0.9464(5) 0.0432(9) Uani 1 d . . C8 C 0.4333(6) 0.1540(5) 0.9064(9) 0.075(2) Uani 1 d . . H8A H 0.3447(6) 0.1784(5) 0.7956(9) 0.113 Uiso 1 d R . H8B H 0.3929(6) 0.1592(5) 1.0032(9) 0.113 Uiso 1 d R . H8C H 0.4630(6) 0.0775(5) 0.8938(9) 0.113 Uiso 1 d R . C9 C 0.5598(7) 0.3454(4) 0.9543(9) 0.086(2) Uani 1 d . . H9A H 0.5245(7) 0.3627(4) 1.0521(9) 0.128 Uiso 1 d R . H9B H 0.4737(7) 0.3707(4) 0.8424(9) 0.128 Uiso 1 d R . H9C H 0.6662(7) 0.3827(4) 0.9736(9) 0.128 Uiso 1 d R . O10 O 0.8629(3) -0.1389(2) 0.8717(3) 0.0238(6) Uani 1 d D . H10B H 0.8822(63) -0.1997(24) 0.9436(53) 0.065(16) Uiso 1 d D . H10A H 0.8741(61) -0.1534(41) 0.7664(33) 0.066(15) Uiso 1 d 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 Zn 0.0258(5) 0.0191(5) 0.0162(5) -0.0005(2) 0.0116(3) 0.0003(2) O1 0.0523(15) 0.0198(12) 0.0172(12) -0.0034(9) 0.0210(10) -0.0032(11) C2 0.032(2) 0.015(2) 0.016(2) -0.0002(15) 0.0103(14) 0.0011(15) C3 0.038(2) 0.016(2) 0.017(2) -0.0012(13) 0.0139(14) 0.0000(14) O4 0.084(2) 0.0188(13) 0.0311(14) -0.0067(10) 0.0379(14) -0.0160(13) O5 0.0317(14) 0.031(2) 0.058(2) 0.0017(12) 0.0222(12) 0.0059(12) C6 0.026(2) 0.036(2) 0.068(3) 0.002(2) 0.015(2) 0.002(2) N7 0.032(2) 0.038(2) 0.056(2) -0.005(2) 0.012(2) 0.0093(14) C8 0.042(3) 0.064(3) 0.132(5) 0.033(3) 0.048(3) 0.014(2) C9 0.056(3) 0.049(3) 0.119(5) -0.020(3) -0.004(3) 0.023(3) O10 0.0343(13) 0.0218(12) 0.0183(12) 0.0006(9) 0.0134(10) -0.0032(10) _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 Zn O10 2.054(2) . ? Zn O10 2.054(2) 3_757 ? Zn O1 2.103(2) . ? Zn O1 2.103(2) 3_757 ? Zn O5 2.151(2) 3_757 ? Zn O5 2.151(2) . ? O1 C2 1.249(4) . ? C2 C3 1.459(5) 3_756 ? C2 C3 1.463(5) . ? C3 O4 1.255(4) . ? C3 C2 1.459(5) 3_756 ? O5 C6 1.229(5) . ? C6 N7 1.311(5) . ? N7 C8 1.443(6) . ? N7 C9 1.459(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 O10 Zn O10 180.0 . 3_757 ? O10 Zn O1 94.45(9) . . ? O10 Zn O1 85.55(9) 3_757 . ? O10 Zn O1 85.55(9) . 3_757 ? O10 Zn O1 94.45(9) 3_757 3_757 ? O1 Zn O1 180.0 . 3_757 ? O10 Zn O5 91.57(10) . 3_757 ? O10 Zn O5 88.43(10) 3_757 3_757 ? O1 Zn O5 89.08(10) . 3_757 ? O1 Zn O5 90.92(10) 3_757 3_757 ? O10 Zn O5 88.43(10) . . ? O10 Zn O5 91.57(10) 3_757 . ? O1 Zn O5 90.92(10) . . ? O1 Zn O5 89.08(10) 3_757 . ? O5 Zn O5 180.0 3_757 . ? C2 O1 Zn 130.6(2) . . ? O1 C2 C3 134.1(3) . 3_756 ? O1 C2 C3 136.6(3) . . ? C3 C2 C3 89.3(2) 3_756 . ? O4 C3 C2 134.7(3) . 3_756 ? O4 C3 C2 134.6(3) . . ? C2 C3 C2 90.7(2) 3_756 . ? C6 O5 Zn 127.8(3) . . ? O5 C6 N7 125.5(4) . . ? C6 N7 C8 120.5(4) . . ? C6 N7 C9 121.7(4) . . ? C8 N7 C9 117.8(4) . . ? _refine_diff_density_max 0.779 _refine_diff_density_min -0.910 _refine_diff_density_rms 0.098