# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_c:\monomeoh _database_code_depnum_ccdc_archive 'CCDC 884011' #TrackingRef 'PES1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 Cu N2 O4, 2(C0.50 H1.50 O0.50), 2(C0.50 H1.50 O0.50)' _chemical_formula_sum 'C18 H18 Cu N2 O6' _chemical_formula_weight 421.88 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 8.2220(16) _cell_length_b 10.509(2) _cell_length_c 11.250(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.63(3) _cell_angle_gamma 90.00 _cell_volume 972.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16525 _cell_measurement_theta_min 4.60 _cell_measurement_theta_max 28.86 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 434 _exptl_absorpt_coefficient_mu 1.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8013 _exptl_absorpt_correction_T_max 0.8013 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; The alcohol hydrogen atoms could not be located for either methanol molecule on the difference map. Additionally the bond length between the oxygen and carbon wis fixed to 1.42 angstroms by means of the DFIX command in both instances. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 16525 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 28.86 _reflns_number_total 2443 _reflns_number_gt 2317 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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^)+(0.0667P)^2^+2.5091P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2443 _refine_ls_number_parameters 124 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.099 _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 Cu1 Cu 0.0000 0.5000 0.5000 0.01084(17) Uani 1 2 d S . . O1 O 0.4923(2) 0.85749(18) 0.88748(16) 0.0159(4) Uani 1 1 d . . . O2 O 0.8063(2) 0.6072(2) 0.62572(18) 0.0223(4) Uani 1 1 d . . . N1 N 0.1912(2) 0.5723(2) 0.58514(18) 0.0123(4) Uani 1 1 d . . . C1 C 0.1976(3) 0.6935(2) 0.6191(2) 0.0156(5) Uani 1 1 d . . . H1 H 0.1055 0.7461 0.6048 0.019 Uiso 1 1 calc R . . C2 C 0.3324(3) 0.7458(2) 0.6742(2) 0.0169(5) Uani 1 1 d . . . H2 H 0.3314 0.8324 0.6985 0.020 Uiso 1 1 calc R . . C3 C 0.4699(3) 0.6712(2) 0.6942(2) 0.0137(4) Uani 1 1 d . . . C7 C 0.6179(3) 0.8148(2) 0.8346(2) 0.0159(5) Uani 1 1 d . . . H7 H 0.7203 0.8482 0.8590 0.019 Uiso 1 1 calc R . . C5 C 0.3203(3) 0.4986(2) 0.6076(2) 0.0152(5) Uani 1 1 d . . . H5 H 0.3154 0.4113 0.5860 0.018 Uiso 1 1 calc R . . C6 C 0.6187(3) 0.7242(3) 0.7450(2) 0.0167(5) Uani 1 1 d . . . C4 C 0.4599(3) 0.5441(2) 0.6609(2) 0.0153(5) Uani 1 1 d . . . H4 H 0.5495 0.4888 0.6749 0.018 Uiso 1 1 calc R . . C8 C 0.7759(3) 0.6866(3) 0.7032(2) 0.0207(5) Uani 1 1 d . . . H8 H 0.8668 0.7276 0.7392 0.025 Uiso 1 1 calc R . . O3 O -0.1588(11) 0.8890(9) 0.4848(8) 0.077(2) Uiso 0.50 1 d PD A 2 C9 C -0.0770(11) 0.9359(9) 0.5773(8) 0.052(2) Uiso 0.50 1 d PD A 2 H9A H 0.0061 0.9953 0.5492 0.078 Uiso 0.50 1 calc PR A 2 H9B H -0.0246 0.8663 0.6212 0.078 Uiso 0.50 1 calc PR A 2 H9C H -0.1521 0.9809 0.6296 0.078 Uiso 0.50 1 calc PR A 2 C10 C 1.1869(17) 0.5729(14) 0.9821(12) 0.076(3) Uiso 0.50 1 d PD B 1 H10A H 1.2148 0.6558 1.0166 0.115 Uiso 0.50 1 calc PR B 1 H10B H 1.2758 0.5439 0.9315 0.115 Uiso 0.50 1 calc PR B 1 H10C H 1.1698 0.5111 1.0459 0.115 Uiso 0.50 1 calc PR B 1 O4 O 1.040(2) 0.585(3) 0.912(2) 0.255(11) Uiso 0.50 1 d PD B 1 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 Cu1 0.0078(2) 0.0133(2) 0.0113(2) 0.00244(13) -0.00297(14) -0.00221(12) O1 0.0103(8) 0.0194(8) 0.0180(8) -0.0077(7) -0.0016(6) 0.0011(6) O2 0.0129(8) 0.0293(10) 0.0247(10) -0.0124(8) 0.0017(7) 0.0008(7) N1 0.0092(8) 0.0155(9) 0.0120(9) -0.0004(7) -0.0020(7) -0.0008(7) C1 0.0112(10) 0.0162(11) 0.0195(11) -0.0032(9) -0.0026(8) 0.0016(8) C2 0.0126(11) 0.0169(11) 0.0211(12) -0.0058(9) -0.0031(9) 0.0010(8) C3 0.0096(10) 0.0188(11) 0.0125(10) -0.0040(9) -0.0007(8) -0.0011(8) C7 0.0109(10) 0.0194(11) 0.0175(11) -0.0049(9) -0.0017(8) -0.0006(8) C5 0.0117(12) 0.0161(12) 0.0176(12) -0.0012(8) -0.0031(9) 0.0002(8) C6 0.0090(10) 0.0223(12) 0.0187(11) -0.0078(10) -0.0013(8) -0.0012(9) C4 0.0093(10) 0.0179(11) 0.0186(11) -0.0030(9) -0.0030(8) 0.0017(8) C8 0.0101(11) 0.0287(13) 0.0233(12) -0.0110(11) -0.0006(9) -0.0012(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 Cu1 O1 1.9615(18) 4_575 ? Cu1 O1 1.9615(18) 2_546 ? Cu1 N1 1.983(2) 3_566 ? Cu1 N1 1.983(2) . ? Cu1 O2 2.4201(19) 3_666 ? Cu1 O2 2.4201(19) 1_455 ? O1 C7 1.279(3) . ? O1 Cu1 1.9615(18) 2_556 ? O2 C8 1.234(3) . ? O2 Cu1 2.4201(19) 1_655 ? N1 C1 1.331(3) . ? N1 C5 1.336(3) . ? C1 C2 1.378(3) . ? C1 H1 0.9500 . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 C6 1.455(3) . ? C7 C6 1.387(3) . ? C7 H7 0.9500 . ? C5 C4 1.375(3) . ? C5 H5 0.9500 . ? C6 C8 1.435(3) . ? C4 H4 0.9500 . ? C8 H8 0.9500 . ? O3 C9 1.327(8) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O4 1.438(10) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.0 4_575 2_546 ? O1 Cu1 N1 87.75(8) 4_575 3_566 ? O1 Cu1 N1 92.25(8) 2_546 3_566 ? O1 Cu1 N1 92.25(8) 4_575 . ? O1 Cu1 N1 87.75(8) 2_546 . ? N1 Cu1 N1 180.0 3_566 . ? O1 Cu1 O2 89.73(8) 4_575 3_666 ? O1 Cu1 O2 90.27(8) 2_546 3_666 ? N1 Cu1 O2 93.60(8) 3_566 3_666 ? N1 Cu1 O2 86.40(8) . 3_666 ? O1 Cu1 O2 90.27(8) 4_575 1_455 ? O1 Cu1 O2 89.73(8) 2_546 1_455 ? N1 Cu1 O2 86.40(8) 3_566 1_455 ? N1 Cu1 O2 93.60(8) . 1_455 ? O2 Cu1 O2 180.0 3_666 1_455 ? C7 O1 Cu1 123.20(16) . 2_556 ? C8 O2 Cu1 150.15(18) . 1_655 ? C1 N1 C5 118.2(2) . . ? C1 N1 Cu1 122.25(16) . . ? C5 N1 Cu1 119.57(17) . . ? N1 C1 C2 122.7(2) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C1 C2 C3 119.7(2) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 116.9(2) . . ? C4 C3 C6 121.4(2) . . ? C2 C3 C6 121.7(2) . . ? O1 C7 C6 126.1(2) . . ? O1 C7 H7 116.9 . . ? C6 C7 H7 116.9 . . ? N1 C5 C4 122.6(2) . . ? N1 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C7 C6 C8 116.0(2) . . ? C7 C6 C3 122.5(2) . . ? C8 C6 C3 121.5(2) . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? O2 C8 C6 127.4(2) . . ? O2 C8 H8 116.3 . . ? C6 C8 H8 116.3 . . ? O3 C9 H9A 109.5 . . ? O3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.539 _refine_diff_density_min -0.790 _refine_diff_density_rms 0.113 data_pierre\monop _database_code_depnum_ccdc_archive 'CCDC 884012' #TrackingRef 'PES2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 Cu N2 O4, 2(C2 H3 N)' _chemical_formula_sum 'C20 H18 Cu N4 O4' _chemical_formula_weight 441.92 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' Cu Cu 0.3201 1.2651 '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 8.2896(6) _cell_length_b 10.1177(8) _cell_length_c 11.5102(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.944(2) _cell_angle_gamma 90.00 _cell_volume 965.25(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6224 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 28.45 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 454 _exptl_absorpt_coefficient_mu 1.166 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.710698 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 6074 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 28.45 _reflns_number_total 2360 _reflns_number_gt 1992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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^)+(0.0406P)^2^+0.2973P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2360 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0400 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Cu1 Cu 0.0000 0.5000 0.0000 0.00910(10) Uani 1 2 d S . . O1 O 0.19697(15) 0.59073(14) 0.13693(12) 0.0181(3) Uani 1 1 d . . . N1 N 0.18899(17) 0.43564(15) -0.09049(13) 0.0103(3) Uani 1 1 d . . . C1 C 0.2294(2) 0.66440(19) 0.21949(17) 0.0134(4) Uani 1 1 d . . . H1 H 0.144(3) 0.705(2) 0.2611(19) 0.016(6) Uiso 1 1 d . . . H3 H 0.218(2) 0.318(2) 0.1209(18) 0.010(5) Uiso 1 1 d . . . O2 O -0.01011(14) 0.33527(12) 0.09207(11) 0.0125(3) Uani 1 1 d . . . N2 N 0.5166(3) 0.1779(2) 0.0469(2) 0.0370(5) Uani 1 1 d . . . C2 C 0.3867(2) 0.70103(18) 0.26203(16) 0.0119(4) Uani 1 1 d . . . C3 C 0.1137(2) 0.29012(18) 0.14556(17) 0.0118(4) Uani 1 1 d . . . C4 C 0.5347(2) 0.65200(18) 0.20801(16) 0.0106(3) Uani 1 1 d . . . C5 C 0.5423(2) 0.52703(18) 0.15704(17) 0.0126(4) Uani 1 1 d . . . H5 H 0.454(3) 0.468(2) 0.1610(19) 0.012(5) Uiso 1 1 d . . . C6 C 0.3203(2) 0.51277(18) -0.10026(17) 0.0122(4) Uani 1 1 d . . . H6 H 0.315(2) 0.5963(19) -0.0650(16) 0.000(4) Uiso 1 1 d . . . H8 H 0.321(2) 0.187(2) -0.2314(19) 0.013(5) Uiso 1 1 d . . . C7 C 0.1935(2) 0.31618(18) -0.14170(17) 0.0127(4) Uani 1 1 d . . . H7 H 0.098(3) 0.261(2) -0.1316(19) 0.013(5) Uiso 1 1 d . . . C8 C 0.3254(2) 0.26988(18) -0.20066(17) 0.0132(4) Uani 1 1 d . . . C9 C 0.6338(3) 0.1248(2) 0.0245(2) 0.0287(5) Uani 1 1 d . . . C10 C 0.7839(3) 0.0594(3) -0.0049(3) 0.0421(7) Uani 1 1 d . . . H10A H 0.7907 0.0515 -0.0877 0.063 Uiso 1 1 calc R . . H10B H 0.7866 -0.0270 0.0296 0.063 Uiso 1 1 calc R . . H10C H 0.8734 0.1105 0.0242 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.00758(15) 0.00968(16) 0.01011(17) 0.00200(12) 0.00243(11) 0.00173(11) O1 0.0124(6) 0.0237(8) 0.0180(7) -0.0076(6) -0.0004(5) -0.0022(5) N1 0.0081(6) 0.0126(8) 0.0104(8) 0.0006(6) 0.0010(6) 0.0012(5) C1 0.0107(8) 0.0147(9) 0.0149(10) -0.0006(7) 0.0022(7) -0.0001(7) O2 0.0101(6) 0.0140(6) 0.0134(7) 0.0045(5) -0.0002(5) 0.0006(5) N2 0.0396(12) 0.0336(12) 0.0379(13) -0.0036(10) 0.0036(10) -0.0044(9) C2 0.0099(8) 0.0125(9) 0.0132(9) -0.0012(7) 0.0013(7) -0.0001(6) C3 0.0093(8) 0.0114(9) 0.0147(10) 0.0003(7) 0.0023(7) -0.0009(6) C4 0.0091(7) 0.0134(9) 0.0093(9) -0.0001(7) 0.0004(6) 0.0004(6) C5 0.0102(8) 0.0139(9) 0.0137(10) -0.0014(7) 0.0017(7) -0.0013(6) C6 0.0121(8) 0.0108(9) 0.0137(9) -0.0017(7) 0.0002(7) 0.0004(6) C7 0.0103(8) 0.0148(9) 0.0129(10) -0.0007(7) 0.0008(7) -0.0028(7) C8 0.0125(8) 0.0111(9) 0.0162(10) -0.0047(7) 0.0021(7) -0.0015(7) C9 0.0341(12) 0.0234(11) 0.0286(13) -0.0005(10) -0.0010(10) -0.0083(9) C10 0.0355(13) 0.0343(15) 0.0567(19) -0.0105(13) 0.0023(13) -0.0001(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.9776(12) . ? Cu1 O2 1.9776(12) 3_565 ? Cu1 N1 2.0043(15) 3_565 ? Cu1 N1 2.0043(15) . ? Cu1 O1 2.4306(13) 3_565 ? Cu1 O1 2.4306(13) . ? O1 C1 1.234(2) . ? N1 C6 1.345(2) . ? N1 C7 1.346(2) . ? C1 C2 1.434(2) . ? C1 H1 0.95(2) . ? O2 C3 1.273(2) . ? N2 C9 1.143(3) . ? C2 C3 1.394(3) 2 ? C2 C4 1.471(2) . ? C3 C2 1.394(3) 2_545 ? C3 H3 0.96(2) . ? C4 C5 1.396(3) . ? C4 C8 1.407(2) 3_665 ? C5 C6 1.383(3) 3_665 ? C5 H5 0.95(2) . ? C6 C5 1.383(3) 3_665 ? C6 H6 0.939(19) . ? C7 C8 1.378(2) . ? C7 H7 0.97(2) . ? C8 C4 1.407(2) 3_665 ? C8 H8 0.91(2) . ? C9 C10 1.454(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.00(7) . 3_565 ? O2 Cu1 N1 87.42(6) . 3_565 ? O2 Cu1 N1 92.58(6) 3_565 3_565 ? O2 Cu1 N1 92.58(6) . . ? O2 Cu1 N1 87.42(6) 3_565 . ? N1 Cu1 N1 180.0 3_565 . ? O2 Cu1 O1 89.73(5) . 3_565 ? O2 Cu1 O1 90.27(5) 3_565 3_565 ? N1 Cu1 O1 86.40(5) 3_565 3_565 ? N1 Cu1 O1 93.60(5) . 3_565 ? O2 Cu1 O1 90.27(5) . . ? O2 Cu1 O1 89.73(5) 3_565 . ? N1 Cu1 O1 93.60(5) 3_565 . ? N1 Cu1 O1 86.40(5) . . ? O1 Cu1 O1 180.00(8) 3_565 . ? C1 O1 Cu1 149.68(12) . . ? C6 N1 C7 117.14(15) . . ? C6 N1 Cu1 119.69(12) . . ? C7 N1 Cu1 123.17(12) . . ? O1 C1 C2 127.21(17) . . ? O1 C1 H1 119.3(13) . . ? C2 C1 H1 113.4(13) . . ? C3 O2 Cu1 121.37(11) . . ? C3 C2 C1 114.43(16) 2 . ? C3 C2 C4 123.61(16) 2 . ? C1 C2 C4 121.91(16) . . ? O2 C3 C2 126.04(16) . 2_545 ? O2 C3 H3 118.5(12) . . ? C2 C3 H3 115.5(12) 2_545 . ? C5 C4 C8 116.15(16) . 3_665 ? C5 C4 C2 121.81(16) . . ? C8 C4 C2 122.00(16) 3_665 . ? C6 C5 C4 120.38(16) 3_665 . ? C6 C5 H5 119.1(14) 3_665 . ? C4 C5 H5 120.5(14) . . ? N1 C6 C5 122.99(17) . 3_665 ? N1 C6 H6 116.1(11) . . ? C5 C6 H6 120.9(11) 3_665 . ? N1 C7 C8 123.30(16) . . ? N1 C7 H7 115.6(13) . . ? C8 C7 H7 121.1(13) . . ? C7 C8 C4 119.99(17) . 3_665 ? C7 C8 H8 118.4(13) . . ? C4 C8 H8 121.6(13) 3_665 . ? N2 C9 C10 179.0(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.45 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.442 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.073 data_c:\monop _database_code_depnum_ccdc_archive 'CCDC 884013' #TrackingRef 'PES3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 Co N2 O4, 2(C H4 O)' _chemical_formula_sum 'C18 H20 Co N2 O6' _chemical_formula_weight 419.29 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_hall_group_name_H-M '-P 2yn' 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 8.2010(16) _cell_length_b 10.492(2) _cell_length_c 11.125(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.28(3) _cell_angle_gamma 90.00 _cell_volume 953.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16040 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 31.49 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.01 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 434 _exptl_absorpt_coefficient_mu 0.937 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.710698 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Australian synchrotron MX1' _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'ADSC Quantum 210r' _diffrn_measurement_method 'scans in phi' _diffrn_detector_area_resol_mean none _diffrn_standards_number 0 _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 16040 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 31.49 _reflns_number_total 2363 _reflns_number_gt 2241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Blu-Ice (McPhillips et al, 2002)' _computing_cell_refinement 'XDS (Kabsch, 1993)' _computing_data_reduction 'XDS (Kabsch, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics X-SEED _computing_publication_material 'XCIF V6.12 (BrukerAXS, 2001).' _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^)+(0.0790P)^2^+2.7483P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2363 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.1534 _refine_ls_wR_factor_gt 0.1517 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Co1 Co 1.0000 0.5000 0.0000 0.00721(18) Uani 1 2 d S . . C1 C 1.3147(3) 0.5127(2) 0.1202(2) 0.0129(5) Uani 1 1 d . . . H1 H 1.2984 0.5999 0.0996 0.015 Uiso 1 1 calc R . . N1 N 1.1951(2) 0.4308(2) 0.09728(18) 0.0102(4) Uani 1 1 d . . . C2 C 1.4554(3) 0.4752(3) 0.1711(2) 0.0125(5) Uani 1 1 d . . . H2 H 1.5420 0.5345 0.1877 0.015 Uiso 1 1 calc R . . C4 C 1.3514(3) 0.2632(2) 0.1793(2) 0.0127(5) Uani 1 1 d . . . H4 H 1.3630 0.1759 0.2010 0.015 Uiso 1 1 calc R . . C5 C 1.2146(3) 0.3078(2) 0.1277(2) 0.0122(5) Uani 1 1 d . . . H5 H 1.1251 0.2511 0.1109 0.015 Uiso 1 1 calc R . . C3 C 1.4779(3) 0.3475(2) 0.2011(2) 0.0105(5) Uani 1 1 d . . . O1 O 1.0011(2) 0.33585(18) -0.10306(17) 0.0140(4) Uani 1 1 d . . . O2 O 1.1907(2) 0.57570(19) -0.11698(16) 0.0140(4) Uani 1 1 d . . . C6 C 1.6291(3) 0.3031(2) 0.2493(2) 0.0118(5) Uani 1 1 d . . . C8 C 1.6277(3) 0.2117(2) 0.3412(2) 0.0122(5) Uani 1 1 d . . . H8 H 1.7320 0.1779 0.3685 0.015 Uiso 1 1 calc R . . C7 C 1.7844(3) 0.3461(3) 0.2009(2) 0.0136(5) Uani 1 1 d . . . H7 H 1.8809 0.3087 0.2394 0.016 Uiso 1 1 calc R . . O3 O 0.8883(7) 0.0996(5) 0.0363(9) 0.146(4) Uani 1 1 d . . . H3 H 0.9038 0.1783 0.0289 0.175 Uiso 1 1 calc R . . C9 C 0.7339(12) 0.0728(7) 0.0035(7) 0.095(3) Uani 1 1 d . . . H9A H 0.7018 -0.0032 0.0468 0.142 Uiso 1 1 calc R . . H9B H 0.7200 0.0567 -0.0836 0.142 Uiso 1 1 calc R . . H9C H 0.6650 0.1449 0.0229 0.142 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0055(3) 0.0086(3) 0.0066(3) -0.00019(14) -0.00430(16) 0.00009(14) C1 0.0114(12) 0.0128(11) 0.0135(12) 0.0006(8) -0.0041(9) 0.0004(9) N1 0.0081(9) 0.0128(9) 0.0086(9) 0.0012(7) -0.0050(7) 0.0013(7) C2 0.0106(11) 0.0118(10) 0.0140(11) 0.0018(9) -0.0052(9) -0.0012(9) C4 0.0112(11) 0.0120(11) 0.0138(11) 0.0024(8) -0.0055(9) -0.0009(9) C5 0.0102(11) 0.0128(11) 0.0125(11) 0.0014(8) -0.0045(8) -0.0023(9) C3 0.0077(10) 0.0146(11) 0.0087(10) 0.0022(8) -0.0027(8) 0.0003(9) O1 0.0107(8) 0.0148(9) 0.0151(9) -0.0063(7) -0.0060(6) 0.0011(7) O2 0.0094(8) 0.0188(9) 0.0130(8) 0.0048(7) -0.0028(6) -0.0014(7) C6 0.0103(11) 0.0132(11) 0.0112(11) 0.0027(8) -0.0034(8) 0.0008(9) C8 0.0090(10) 0.0134(11) 0.0133(11) 0.0028(9) -0.0044(8) 0.0015(9) C7 0.0094(11) 0.0162(11) 0.0143(11) 0.0028(9) -0.0040(8) 0.0005(9) O3 0.094(4) 0.072(3) 0.287(10) -0.096(5) 0.104(5) -0.048(3) C9 0.167(9) 0.055(4) 0.070(4) -0.018(3) 0.047(5) -0.020(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 Co1 N1 1.9851(19) 3_765 ? Co1 N1 1.9851(19) . ? Co1 O1 2.0695(18) 3_765 ? Co1 O1 2.0695(18) . ? Co1 O2 2.268(2) 3_765 ? Co1 O2 2.268(2) . ? C1 C2 1.298(3) . ? C1 N1 1.312(3) . ? C1 H1 0.9500 . ? N1 C5 1.339(3) . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? C4 C5 1.300(3) . ? C4 C3 1.368(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C3 C6 1.386(3) . ? O1 C8 1.352(3) 4_565 ? O2 C7 1.273(3) 3_865 ? C6 C8 1.402(3) . ? C6 C7 1.497(4) . ? C8 O1 1.352(3) 4_666 ? C8 H8 0.9500 . ? C7 O2 1.273(3) 3_865 ? C7 H7 0.9500 . ? O3 C9 1.315(10) . ? O3 H3 0.8400 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Co1 N1 180.00(11) 3_765 . ? N1 Co1 O1 87.30(8) 3_765 3_765 ? N1 Co1 O1 92.70(8) . 3_765 ? N1 Co1 O1 92.70(8) 3_765 . ? N1 Co1 O1 87.30(8) . . ? O1 Co1 O1 180.00(10) 3_765 . ? N1 Co1 O2 82.95(8) 3_765 3_765 ? N1 Co1 O2 97.05(8) . 3_765 ? O1 Co1 O2 86.27(8) 3_765 3_765 ? O1 Co1 O2 93.73(8) . 3_765 ? N1 Co1 O2 97.05(8) 3_765 . ? N1 Co1 O2 82.95(8) . . ? O1 Co1 O2 93.73(8) 3_765 . ? O1 Co1 O2 86.27(8) . . ? O2 Co1 O2 180.00(9) 3_765 . ? C2 C1 N1 120.3(2) . . ? C2 C1 H1 119.8 . . ? N1 C1 H1 119.8 . . ? C1 N1 C5 120.8(2) . . ? C1 N1 Co1 114.65(17) . . ? C5 N1 Co1 124.17(16) . . ? C1 C2 C3 119.4(2) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C5 C4 C3 117.1(2) . . ? C5 C4 H4 121.5 . . ? C3 C4 H4 121.5 . . ? C4 C5 N1 122.5(2) . . ? C4 C5 H5 118.8 . . ? N1 C5 H5 118.8 . . ? C4 C3 C6 119.2(2) . . ? C4 C3 C2 119.9(2) . . ? C6 C3 C2 120.8(2) . . ? C8 O1 Co1 127.16(15) 4_565 . ? C7 O2 Co1 144.30(17) 3_865 . ? C3 C6 C8 116.4(2) . . ? C3 C6 C7 121.3(2) . . ? C8 C6 C7 122.2(2) . . ? O1 C8 C6 130.2(2) 4_666 . ? O1 C8 H8 114.9 4_666 . ? C6 C8 H8 114.9 . . ? O2 C7 C6 131.1(2) 3_865 . ? O2 C7 H7 114.5 3_865 . ? C6 C7 H7 114.5 . . ? C9 O3 H3 109.5 . . ? O3 C9 H9A 109.5 . . ? O3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.744 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.012 _refine_diff_density_min -1.330 _refine_diff_density_rms 0.132