Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Thorsten Glaser' 'Roland Frohlich' 'Ioannis Liratzis' _publ_contact_author_name 'Dr Thorsten Glaser' _publ_contact_author_address ; Westfalische Wilhelms-Universitat Munster Institut fur Anorganische und Analytische Chemie Muenster D-48149 GERMANY ; _publ_contact_author_email TGLASER@UNI-MUENSTER.DE _publ_requested_journal 'Dalton Transactions' _publ_section_title ; A 1,8-Naphthalenediol-Based Unsymmetrical Dinucleating Ligand ; data_han2527 _database_code_depnum_ccdc_archive 'CCDC 273592' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H22 N2 O4' _chemical_formula_weight 414.45 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 14.731(1) _cell_length_b 8.650(1) _cell_length_c 16.954(1) _cell_angle_alpha 90.00 _cell_angle_beta 109.91(1) _cell_angle_gamma 90.00 _cell_volume 2031.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.753 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7046 _exptl_absorpt_correction_T_max 0.9285 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11122 _diffrn_reflns_av_R_equivalents 0.042 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.38 _diffrn_reflns_theta_max 63.65 _reflns_number_total 3209 _reflns_number_gt 1845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Due the weak diffracting power of the crystals and the physical limitations of the instrument used (CCD with Cu-radiation) the resolution and completeness of the data set is limited. ; _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^)+(0.0776P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at nitrogen and oxygen from difmap, other geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3209 _refine_ls_number_parameters 288 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0849 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1449 _refine_ls_wR_factor_gt 0.1274 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 O1 O 1.11716(11) 0.59906(17) -0.33626(10) 0.0679(5) Uani 1 1 d . . . O2 O 1.13394(14) 0.7541(2) -0.45711(13) 0.0918(6) Uani 1 1 d . . . H2 H 1.1061 0.7078 -0.4290 0.138 Uiso 1 1 calc R . . N1 N 1.10205(15) 0.4366(2) -0.21134(13) 0.0608(5) Uani 1 1 d . . . H1 H 1.0683(16) 0.483(2) -0.2652(15) 0.073 Uiso 1 1 d . . . C1 C 1.01496(18) 0.4822(3) -0.11088(15) 0.0653(7) Uani 1 1 d . . . H1A H 0.9783 0.4278 -0.0808 0.078 Uiso 1 1 calc R . . H1B H 1.0732 0.5250 -0.0691 0.078 Uiso 1 1 calc R . . C2 C 1.04403(17) 0.3680(3) -0.16624(15) 0.0664(7) Uani 1 1 d . . . H2A H 1.0806 0.2834 -0.1312 0.080 Uiso 1 1 calc R . . H2B H 0.9855 0.3237 -0.2069 0.080 Uiso 1 1 calc R . . C3 C 1.19577(18) 0.4289(3) -0.18817(16) 0.0662(7) Uani 1 1 d . . . H3 H 1.2281 0.3738 -0.1388 0.079 Uiso 1 1 calc R . . C4 C 1.25208(17) 0.4952(3) -0.23022(16) 0.0659(7) Uani 1 1 d . . . C5 C 1.20866(17) 0.5819(2) -0.30530(15) 0.0589(6) Uani 1 1 d . . . C6 C 1.26983(18) 0.6516(3) -0.34647(17) 0.0680(7) Uani 1 1 d . . . C7 C 1.2305(2) 0.7396(3) -0.4198(2) 0.0751(8) Uani 1 1 d . . . C8 C 1.2890(3) 0.8083(3) -0.4585(2) 0.1023(11) Uani 1 1 d . . . H8 H 1.2620 0.8657 -0.5081 0.123 Uiso 1 1 calc R . . C9 C 1.3872(3) 0.7909(4) -0.4232(3) 0.1338(15) Uani 1 1 d . . . H9 H 1.4272 0.8392 -0.4487 0.161 Uiso 1 1 calc R . . C10 C 1.4296(3) 0.7039(5) -0.3505(3) 0.1366(15) Uani 1 1 d . . . H10 H 1.4971 0.6929 -0.3282 0.164 Uiso 1 1 calc R . . C11 C 1.3712(2) 0.6333(3) -0.3111(2) 0.0963(10) Uani 1 1 d . . . C12 C 1.4110(2) 0.5446(4) -0.2365(3) 0.1171(12) Uani 1 1 d . . . H12 H 1.4783 0.5321 -0.2132 0.141 Uiso 1 1 calc R . . C13 C 1.3540(2) 0.4782(4) -0.1989(2) 0.1007(10) Uani 1 1 d . . . H13 H 1.3825 0.4188 -0.1503 0.121 Uiso 1 1 calc R . . O21 O 0.91250(11) 0.88724(16) 0.00978(9) 0.0636(5) Uani 1 1 d . . . O22 O 0.91568(13) 1.0557(2) 0.13229(12) 0.0840(6) Uani 1 1 d . . . H22 H 0.9338 1.0249 0.0937 0.126 Uiso 1 1 calc R . . N21 N 0.90729(15) 0.6990(2) -0.11278(13) 0.0628(5) Uani 1 1 d . . . H21 H 0.9486(16) 0.764(2) -0.0640(15) 0.075 Uiso 1 1 d . . . C22 C 0.95515(19) 0.6110(3) -0.16084(15) 0.0700(7) Uani 1 1 d . . . H22A H 0.9965 0.6806 -0.1793 0.084 Uiso 1 1 calc R . . H22B H 0.9063 0.5684 -0.2110 0.084 Uiso 1 1 calc R . . C23 C 0.81718(18) 0.6839(2) -0.12034(16) 0.0666(7) Uani 1 1 d . . . H23 H 0.7797 0.6162 -0.1622 0.080 Uiso 1 1 calc R . . C24 C 0.77063(16) 0.7595(2) -0.07165(16) 0.0596(6) Uani 1 1 d . . . C25 C 0.82277(16) 0.8607(2) -0.00600(14) 0.0543(6) Uani 1 1 d . . . C26 C 0.77218(17) 0.9306(2) 0.04501(15) 0.0609(6) Uani 1 1 d . . . C27 C 0.82138(19) 1.0294(3) 0.11245(16) 0.0703(7) Uani 1 1 d . . . C28 C 0.7728(2) 1.0969(3) 0.16019(19) 0.0997(10) Uani 1 1 d . . . H28 H 0.8058 1.1625 0.2050 0.120 Uiso 1 1 calc R . . C29 C 0.6767(3) 1.0685(4) 0.1423(2) 0.1196(13) Uani 1 1 d . . . H29 H 0.6441 1.1174 0.1744 0.144 Uiso 1 1 calc R . . C30 C 0.6264(2) 0.9701(4) 0.0786(2) 0.1084(11) Uani 1 1 d . . . H30 H 0.5609 0.9493 0.0691 0.130 Uiso 1 1 calc R . . C31 C 0.67305(19) 0.9005(3) 0.02747(18) 0.0792(8) Uani 1 1 d . . . C32 C 0.62393(19) 0.7996(3) -0.0394(2) 0.0939(9) Uani 1 1 d . . . H32 H 0.5580 0.7790 -0.0510 0.113 Uiso 1 1 calc R . . C33 C 0.67068(18) 0.7328(3) -0.08673(19) 0.0858(9) Uani 1 1 d . . . H33 H 0.6363 0.6668 -0.1308 0.103 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 O1 0.0594(10) 0.0820(10) 0.0654(11) 0.0126(9) 0.0252(9) 0.0107(8) O2 0.1018(15) 0.0916(13) 0.0984(16) 0.0285(11) 0.0552(13) 0.0177(11) N1 0.0671(14) 0.0641(12) 0.0522(13) 0.0053(10) 0.0216(11) 0.0086(10) C1 0.0814(17) 0.0638(14) 0.0544(15) 0.0019(12) 0.0281(13) 0.0027(12) C2 0.0885(18) 0.0580(13) 0.0626(16) 0.0109(12) 0.0387(15) 0.0134(12) C3 0.0676(17) 0.0661(14) 0.0580(16) -0.0014(13) 0.0125(13) 0.0105(12) C4 0.0571(15) 0.0696(14) 0.0671(17) -0.0037(14) 0.0159(13) 0.0028(12) C5 0.0623(15) 0.0510(12) 0.0663(17) -0.0134(12) 0.0257(13) -0.0006(11) C6 0.0708(17) 0.0559(13) 0.084(2) -0.0126(14) 0.0357(15) -0.0068(12) C7 0.089(2) 0.0557(14) 0.096(2) -0.0047(15) 0.0518(18) -0.0050(14) C8 0.120(3) 0.0718(17) 0.143(3) 0.0036(18) 0.081(3) -0.0082(18) C9 0.130(3) 0.110(3) 0.197(5) 0.003(3) 0.102(4) -0.036(2) C10 0.090(3) 0.139(3) 0.194(5) 0.014(3) 0.067(3) -0.028(2) C11 0.076(2) 0.094(2) 0.126(3) -0.003(2) 0.045(2) -0.0169(16) C12 0.0555(18) 0.150(3) 0.133(3) 0.019(3) 0.016(2) -0.0071(19) C13 0.0626(19) 0.124(2) 0.101(2) 0.018(2) 0.0094(17) 0.0046(17) O21 0.0641(10) 0.0629(9) 0.0655(11) -0.0065(8) 0.0245(9) -0.0054(7) O22 0.0846(13) 0.0825(12) 0.0758(14) -0.0250(10) 0.0153(10) 0.0041(10) N21 0.0735(14) 0.0620(12) 0.0564(13) -0.0064(10) 0.0267(11) 0.0024(10) C22 0.0963(19) 0.0641(14) 0.0593(16) 0.0002(13) 0.0391(15) 0.0092(13) C23 0.0735(17) 0.0562(13) 0.0620(16) -0.0087(12) 0.0125(14) 0.0018(12) C24 0.0603(15) 0.0564(13) 0.0601(16) -0.0028(12) 0.0180(12) 0.0063(11) C25 0.0643(15) 0.0446(11) 0.0518(14) 0.0050(11) 0.0167(12) 0.0075(11) C26 0.0636(15) 0.0594(13) 0.0557(15) 0.0054(12) 0.0152(12) 0.0192(11) C27 0.0725(18) 0.0707(15) 0.0576(17) -0.0065(13) 0.0088(14) 0.0225(13) C28 0.098(2) 0.112(2) 0.074(2) -0.0215(18) 0.0091(18) 0.0469(19) C29 0.105(3) 0.164(3) 0.086(3) -0.021(2) 0.028(2) 0.065(3) C30 0.079(2) 0.145(3) 0.105(3) -0.012(2) 0.036(2) 0.038(2) C31 0.0637(17) 0.0929(18) 0.078(2) -0.0023(16) 0.0199(15) 0.0239(14) C32 0.0571(16) 0.108(2) 0.112(3) -0.020(2) 0.0232(17) 0.0082(15) C33 0.0634(17) 0.0851(18) 0.096(2) -0.0245(17) 0.0095(16) 0.0005(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 O1 C5 1.278(2) . ? O2 C7 1.351(3) . ? N1 C3 1.302(3) . ? N1 C2 1.453(3) . ? C1 C22 1.493(3) . ? C1 C2 1.521(3) . ? C3 C4 1.388(3) . ? C4 C13 1.419(3) . ? C4 C5 1.427(3) . ? C5 C6 1.446(3) . ? C6 C7 1.404(4) . ? C6 C11 1.415(4) . ? C7 C8 1.382(3) . ? C8 C9 1.373(5) . ? C9 C10 1.397(5) . ? C10 C11 1.398(4) . ? C11 C12 1.424(4) . ? C12 C13 1.344(4) . ? O21 C25 1.277(2) . ? O22 C27 1.333(3) . ? N21 C23 1.296(3) . ? N21 C22 1.460(3) . ? C23 C24 1.402(3) . ? C24 C25 1.418(3) . ? C24 C33 1.425(3) . ? C25 C26 1.452(3) . ? C26 C31 1.412(3) . ? C26 C27 1.414(3) . ? C27 C28 1.379(4) . ? C28 C29 1.365(4) . ? C29 C30 1.377(4) . ? C30 C31 1.412(4) . ? C31 C32 1.419(4) . ? C32 C33 1.352(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C2 125.0(2) . . ? C22 C1 C2 111.7(2) . . ? N1 C2 C1 113.56(18) . . ? N1 C3 C4 125.6(2) . . ? C3 C4 C13 120.4(3) . . ? C3 C4 C5 120.7(2) . . ? C13 C4 C5 118.9(2) . . ? O1 C5 C4 121.1(2) . . ? O1 C5 C6 119.8(2) . . ? C4 C5 C6 119.1(2) . . ? C7 C6 C11 119.6(3) . . ? C7 C6 C5 121.1(2) . . ? C11 C6 C5 119.3(3) . . ? O2 C7 C8 117.7(3) . . ? O2 C7 C6 121.1(2) . . ? C8 C7 C6 121.2(3) . . ? C9 C8 C7 118.7(4) . . ? C8 C9 C10 122.2(3) . . ? C9 C10 C11 119.6(4) . . ? C10 C11 C6 118.8(4) . . ? C10 C11 C12 121.7(4) . . ? C6 C11 C12 119.5(3) . . ? C13 C12 C11 121.1(3) . . ? C12 C13 C4 122.1(3) . . ? C23 N21 C22 124.4(2) . . ? N21 C22 C1 112.12(19) . . ? N21 C23 C24 125.8(2) . . ? C23 C24 C25 120.5(2) . . ? C23 C24 C33 120.1(2) . . ? C25 C24 C33 119.4(2) . . ? O21 C25 C24 121.38(19) . . ? O21 C25 C26 120.3(2) . . ? C24 C25 C26 118.3(2) . . ? C31 C26 C27 119.4(2) . . ? C31 C26 C25 120.1(2) . . ? C27 C26 C25 120.5(2) . . ? O22 C27 C28 118.9(3) . . ? O22 C27 C26 120.7(2) . . ? C28 C27 C26 120.3(3) . . ? C29 C28 C27 120.0(3) . . ? C28 C29 C30 121.8(3) . . ? C29 C30 C31 120.0(3) . . ? C30 C31 C26 118.5(3) . . ? C30 C31 C32 122.1(3) . . ? C26 C31 C32 119.4(2) . . ? C33 C32 C31 120.9(3) . . ? C32 C33 C24 121.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C2 C1 98.4(3) . . . . ? C22 C1 C2 N1 61.1(3) . . . . ? C2 N1 C3 C4 -179.3(2) . . . . ? N1 C3 C4 C13 -179.7(2) . . . . ? N1 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 O1 -0.9(3) . . . . ? C13 C4 C5 O1 179.4(2) . . . . ? C3 C4 C5 C6 178.9(2) . . . . ? C13 C4 C5 C6 -0.9(3) . . . . ? O1 C5 C6 C7 0.6(3) . . . . ? C4 C5 C6 C7 -179.2(2) . . . . ? O1 C5 C6 C11 179.3(2) . . . . ? C4 C5 C6 C11 -0.5(3) . . . . ? C11 C6 C7 O2 177.3(2) . . . . ? C5 C6 C7 O2 -4.1(4) . . . . ? C11 C6 C7 C8 0.4(4) . . . . ? C5 C6 C7 C8 179.0(2) . . . . ? O2 C7 C8 C9 -178.0(3) . . . . ? C6 C7 C8 C9 -0.9(4) . . . . ? C7 C8 C9 C10 1.3(6) . . . . ? C8 C9 C10 C11 -1.0(6) . . . . ? C9 C10 C11 C6 0.3(5) . . . . ? C9 C10 C11 C12 -179.5(3) . . . . ? C7 C6 C11 C10 -0.1(4) . . . . ? C5 C6 C11 C10 -178.7(3) . . . . ? C7 C6 C11 C12 179.8(3) . . . . ? C5 C6 C11 C12 1.1(4) . . . . ? C10 C11 C12 C13 179.5(3) . . . . ? C6 C11 C12 C13 -0.3(5) . . . . ? C11 C12 C13 C4 -1.2(5) . . . . ? C3 C4 C13 C12 -178.0(3) . . . . ? C5 C4 C13 C12 1.7(4) . . . . ? C23 N21 C22 C1 -101.7(3) . . . . ? C2 C1 C22 N21 165.8(2) . . . . ? C22 N21 C23 C24 175.8(2) . . . . ? N21 C23 C24 C25 -1.5(4) . . . . ? N21 C23 C24 C33 179.8(2) . . . . ? C23 C24 C25 O21 1.0(3) . . . . ? C33 C24 C25 O21 179.7(2) . . . . ? C23 C24 C25 C26 -177.2(2) . . . . ? C33 C24 C25 C26 1.5(3) . . . . ? O21 C25 C26 C31 -179.80(19) . . . . ? C24 C25 C26 C31 -1.6(3) . . . . ? O21 C25 C26 C27 0.3(3) . . . . ? C24 C25 C26 C27 178.51(19) . . . . ? C31 C26 C27 O22 177.7(2) . . . . ? C25 C26 C27 O22 -2.4(3) . . . . ? C31 C26 C27 C28 -0.6(4) . . . . ? C25 C26 C27 C28 179.3(2) . . . . ? O22 C27 C28 C29 -178.4(3) . . . . ? C26 C27 C28 C29 0.0(4) . . . . ? C27 C28 C29 C30 1.7(5) . . . . ? C28 C29 C30 C31 -2.6(5) . . . . ? C29 C30 C31 C26 1.9(5) . . . . ? C29 C30 C31 C32 -179.3(3) . . . . ? C27 C26 C31 C30 -0.3(4) . . . . ? C25 C26 C31 C30 179.8(2) . . . . ? C27 C26 C31 C32 -179.1(2) . . . . ? C25 C26 C31 C32 1.0(4) . . . . ? C30 C31 C32 C33 -179.1(3) . . . . ? C26 C31 C32 C33 -0.3(4) . . . . ? C31 C32 C33 C24 0.3(5) . . . . ? C23 C24 C33 C32 177.8(3) . . . . ? C25 C24 C33 C32 -0.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 63.65 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.253 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.034 data_han2555 _database_code_depnum_ccdc_archive 'CCDC 273593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H18 Cu2 N2 O4' _chemical_formula_weight 537.49 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 P21/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 8.612(1) _cell_length_b 18.755(1) _cell_length_c 12.243(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.89(1) _cell_angle_gamma 90.00 _cell_volume 1963.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 2.206 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5123 _exptl_absorpt_correction_T_max 0.7332 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16711 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4773 _reflns_number_gt 3698 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinwoski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (BrukerAXS, 2000)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Disorder in the bridging C12-C13-C14 refined with split positions (PART) with a ratio of 0.41(1) to 0.59(1). ; _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^)+(0.0382P)^2^+1.6761P] 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 4773 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.15056(4) -0.051047(18) -0.15126(3) 0.03872(11) Uani 1 1 d . . . Cu2 Cu 0.16976(3) 0.051100(15) 0.03976(2) 0.02551(9) Uani 1 1 d . . . O1 O 0.0515(2) 0.03708(9) -0.10410(13) 0.0319(4) Uani 1 1 d . . . O2 O 0.03632(19) 0.12528(9) 0.07239(13) 0.0301(4) Uani 1 1 d . . . O3 O 0.2722(2) -0.03181(9) -0.00785(14) 0.0320(4) Uani 1 1 d . . . O4 O 0.2901(2) 0.05649(9) 0.17552(14) 0.0318(4) Uani 1 1 d . . . N1 N 0.0199(3) -0.04730(16) -0.2927(2) 0.0526(7) Uani 1 1 d . . . N2 N 0.2839(3) -0.12985(15) -0.1802(2) 0.0570(8) Uani 1 1 d . . . C1 C -0.0810(3) 0.07379(18) -0.2742(2) 0.0454(7) Uani 1 1 d . . . C2 C -0.0282(3) 0.08766(15) -0.16392(19) 0.0339(6) Uani 1 1 d . A . C3 C -0.0591(3) 0.15532(15) -0.1166(2) 0.0333(6) Uani 1 1 d . . . C4 C -0.0209(3) 0.17217(13) -0.0026(2) 0.0306(5) Uani 1 1 d . A . C5 C -0.0476(3) 0.24114(15) 0.0326(2) 0.0405(6) Uani 1 1 d . . . H5 H -0.0205 0.2529 0.1080 0.049 Uiso 1 1 calc R A . C6 C -0.1126(4) 0.29313(17) -0.0394(3) 0.0519(8) Uani 1 1 d . A . H6 H -0.1268 0.3400 -0.0131 0.062 Uiso 1 1 calc R . . C7 C -0.1562(3) 0.27773(18) -0.1473(3) 0.0530(8) Uani 1 1 d . . . H7 H -0.2023 0.3137 -0.1953 0.064 Uiso 1 1 calc R A . C8 C -0.1336(3) 0.20936(17) -0.1879(2) 0.0435(7) Uani 1 1 d . A . C9 C -0.1850(3) 0.1932(2) -0.2986(3) 0.0570(9) Uani 1 1 d . . . H9 H -0.2351 0.2289 -0.3453 0.068 Uiso 1 1 calc R A . C10 C -0.1639(4) 0.1280(2) -0.3388(2) 0.0615(10) Uani 1 1 d . A . H10 H -0.2054 0.1176 -0.4124 0.074 Uiso 1 1 calc R . . C11 C -0.0614(4) 0.0070(2) -0.3266(2) 0.0563(10) Uani 1 1 d . A . H11 H -0.1177 0.0022 -0.3979 0.068 Uiso 1 1 calc R . . C12A C -0.0160(15) -0.0963(6) -0.3812(9) 0.041(2) Uani 0.407(9) 1 d P A 1 H12A H 0.0287 -0.0802 -0.4478 0.049 Uiso 0.407(9) 1 calc PR A 1 H12B H -0.1304 -0.1022 -0.3992 0.049 Uiso 0.407(9) 1 calc PR A 1 C13A C 0.0583(9) -0.1639(5) -0.3382(6) 0.041(2) Uani 0.407(9) 1 d P A 1 H13A H 0.0383 -0.2012 -0.3954 0.050 Uiso 0.407(9) 1 calc PR A 1 H13B H 0.0078 -0.1793 -0.2736 0.050 Uiso 0.407(9) 1 calc PR A 1 C14A C 0.2320(11) -0.1588(6) -0.3049(9) 0.044(3) Uani 0.407(9) 1 d P A 1 H14A H 0.2769 -0.1266 -0.3570 0.053 Uiso 0.407(9) 1 calc PR A 1 H14B H 0.2785 -0.2066 -0.3121 0.053 Uiso 0.407(9) 1 calc PR A 1 C12B C 0.0260(10) -0.1191(5) -0.3545(7) 0.047(2) Uani 0.593(9) 1 d P A 2 H12C H -0.0328 -0.1549 -0.3165 0.056 Uiso 0.593(9) 1 calc PR A 2 H12D H -0.0296 -0.1129 -0.4295 0.056 Uiso 0.593(9) 1 calc PR A 2 C13B C 0.1852(8) -0.1489(3) -0.3648(5) 0.0483(18) Uani 0.593(9) 1 d P A 2 H13C H 0.2537 -0.1097 -0.3846 0.058 Uiso 0.593(9) 1 calc PR A 2 H13D H 0.1764 -0.1840 -0.4255 0.058 Uiso 0.593(9) 1 calc PR A 2 C14B C 0.2608(9) -0.1842(4) -0.2618(5) 0.0424(16) Uani 0.593(9) 1 d P A 2 H14C H 0.1924 -0.2222 -0.2382 0.051 Uiso 0.593(9) 1 calc PR A 2 H14D H 0.3621 -0.2057 -0.2744 0.051 Uiso 0.593(9) 1 calc PR A 2 C15 C 0.4040(4) -0.14887(16) -0.1148(3) 0.0587(10) Uani 1 1 d . A . H15 H 0.4632 -0.1867 -0.1408 0.070 Uiso 1 1 calc R . . C16 C 0.4624(3) -0.12175(14) -0.0089(3) 0.0469(7) Uani 1 1 d . . . C17 C 0.3957(3) -0.06531(13) 0.0444(2) 0.0346(6) Uani 1 1 d . A . C18 C 0.4599(3) -0.04512(13) 0.1533(2) 0.0333(6) Uani 1 1 d . . . C19 C 0.4012(3) 0.01241(13) 0.2139(2) 0.0317(5) Uani 1 1 d . A . C20 C 0.4667(3) 0.02364(16) 0.3227(2) 0.0406(6) Uani 1 1 d . . . H20 H 0.4255 0.0603 0.3644 0.049 Uiso 1 1 calc R A . C21 C 0.5904(3) -0.01730(18) 0.3714(3) 0.0509(8) Uani 1 1 d . A . H21 H 0.6313 -0.0087 0.4458 0.061 Uiso 1 1 calc R . . C22 C 0.6531(3) -0.06933(18) 0.3141(3) 0.0549(9) Uani 1 1 d . . . H22 H 0.7403 -0.0957 0.3475 0.066 Uiso 1 1 calc R A . C23 C 0.5908(3) -0.08458(15) 0.2061(3) 0.0449(7) Uani 1 1 d . A . C24 C 0.6571(4) -0.13964(17) 0.1485(3) 0.0577(9) Uani 1 1 d . . . H24 H 0.7457 -0.1647 0.1828 0.069 Uiso 1 1 calc R A . C25 C 0.5970(4) -0.15705(16) 0.0462(4) 0.0610(10) Uani 1 1 d . A . H25 H 0.6450 -0.1939 0.0090 0.073 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 0.0447(2) 0.0407(2) 0.03353(19) -0.01469(14) 0.01607(14) -0.01434(14) Cu2 0.02921(16) 0.02458(16) 0.02252(15) -0.00069(11) 0.00218(11) -0.00080(11) O1 0.0368(9) 0.0371(10) 0.0215(8) -0.0025(7) 0.0024(7) -0.0079(7) O2 0.0349(9) 0.0298(9) 0.0251(8) 0.0024(7) 0.0019(7) 0.0041(7) O3 0.0345(9) 0.0274(9) 0.0352(9) -0.0064(7) 0.0094(7) -0.0037(7) O4 0.0345(9) 0.0309(9) 0.0283(9) -0.0004(7) -0.0031(7) 0.0035(7) N1 0.0645(17) 0.0658(19) 0.0306(13) -0.0193(13) 0.0184(12) -0.0362(15) N2 0.0538(17) 0.0521(16) 0.0723(19) -0.0366(14) 0.0372(15) -0.0255(13) C1 0.0441(16) 0.067(2) 0.0240(13) 0.0063(13) -0.0007(11) -0.0246(14) C2 0.0315(13) 0.0466(16) 0.0231(12) 0.0091(11) 0.0010(10) -0.0110(11) C3 0.0241(12) 0.0417(15) 0.0338(13) 0.0106(11) 0.0025(9) -0.0048(10) C4 0.0247(12) 0.0324(13) 0.0354(13) 0.0057(11) 0.0060(9) 0.0012(9) C5 0.0411(15) 0.0365(15) 0.0448(16) 0.0068(12) 0.0082(12) 0.0075(11) C6 0.0533(18) 0.0427(17) 0.062(2) 0.0142(15) 0.0174(15) 0.0167(14) C7 0.0410(16) 0.056(2) 0.063(2) 0.0284(17) 0.0093(14) 0.0164(14) C8 0.0294(14) 0.0584(19) 0.0427(16) 0.0219(14) 0.0037(11) 0.0002(12) C9 0.0416(17) 0.085(3) 0.0415(18) 0.0288(18) -0.0075(13) -0.0089(16) C10 0.0546(19) 0.099(3) 0.0271(15) 0.0192(17) -0.0095(13) -0.0303(19) C11 0.060(2) 0.088(3) 0.0208(14) -0.0055(16) 0.0032(13) -0.040(2) C12A 0.056(6) 0.037(6) 0.029(6) -0.007(4) -0.001(4) -0.006(4) C13A 0.050(5) 0.033(4) 0.040(4) -0.016(4) 0.000(3) -0.002(4) C14A 0.045(5) 0.051(7) 0.036(7) -0.025(5) -0.003(5) 0.007(4) C12B 0.062(5) 0.044(6) 0.032(4) -0.008(4) -0.004(3) -0.011(4) C13B 0.068(5) 0.044(3) 0.035(3) -0.024(3) 0.015(3) -0.021(3) C14B 0.055(4) 0.039(4) 0.034(4) -0.013(3) 0.008(3) -0.005(3) C15 0.059(2) 0.0317(16) 0.095(3) -0.0211(17) 0.050(2) -0.0122(14) C16 0.0502(17) 0.0237(13) 0.073(2) 0.0013(14) 0.0344(15) -0.0007(12) C17 0.0331(13) 0.0212(12) 0.0524(17) 0.0061(11) 0.0176(12) -0.0036(9) C18 0.0287(12) 0.0264(13) 0.0461(15) 0.0116(11) 0.0098(11) -0.0031(9) C19 0.0279(12) 0.0302(14) 0.0364(14) 0.0093(11) 0.0013(10) -0.0079(10) C20 0.0386(15) 0.0415(15) 0.0396(15) 0.0049(13) -0.0042(11) -0.0038(12) C21 0.0411(16) 0.058(2) 0.0497(18) 0.0199(16) -0.0086(13) -0.0071(14) C22 0.0356(16) 0.058(2) 0.070(2) 0.0342(18) 0.0006(14) 0.0047(14) C23 0.0343(14) 0.0341(15) 0.068(2) 0.0235(14) 0.0149(13) 0.0020(11) C24 0.0454(18) 0.0366(17) 0.095(3) 0.0266(18) 0.0267(18) 0.0104(13) C25 0.059(2) 0.0261(15) 0.107(3) 0.0126(17) 0.050(2) 0.0110(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 Cu1 N2 1.930(3) . ? Cu1 N1 1.950(3) . ? Cu1 O3 1.9669(18) . ? Cu1 O1 1.9776(18) . ? Cu1 O2 2.4153(17) 3 ? Cu1 Cu2 3.0124(4) . ? Cu2 O4 1.8530(17) . ? Cu2 O2 1.8778(17) . ? Cu2 O3 1.9127(17) . ? Cu2 O1 1.9437(16) . ? O1 C2 1.337(3) . ? O2 C4 1.323(3) . ? O2 Cu1 2.4153(17) 3 ? O3 C17 1.331(3) . ? O4 C19 1.308(3) . ? N1 C11 1.277(5) . ? N1 C12A 1.426(12) . ? N1 C12B 1.548(9) . ? N2 C15 1.280(5) . ? N2 C14B 1.424(6) . ? N2 C14A 1.631(10) . ? C1 C2 1.397(4) . ? C1 C10 1.426(5) . ? C1 C11 1.427(5) . ? C2 C3 1.433(4) . ? C3 C4 1.431(4) . ? C3 C8 1.438(4) . ? C4 C5 1.391(4) . ? C5 C6 1.387(4) . ? C6 C7 1.360(5) . ? C7 C8 1.397(5) . ? C8 C9 1.407(4) . ? C9 C10 1.337(5) . ? C12A C13A 1.487(13) . ? C13A C14A 1.506(12) . ? C12B C13B 1.500(10) . ? C13B C14B 1.502(9) . ? C15 C16 1.427(5) . ? C16 C17 1.403(4) . ? C16 C25 1.431(5) . ? C17 C18 1.431(4) . ? C18 C19 1.435(4) . ? C18 C23 1.436(4) . ? C19 C20 1.399(4) . ? C20 C21 1.388(4) . ? C21 C22 1.352(5) . ? C22 C23 1.395(5) . ? C23 C24 1.410(5) . ? C24 C25 1.338(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 N2 Cu1 N1 99.04(13) . . ? N2 Cu1 O3 92.26(11) . . ? N1 Cu1 O3 167.13(10) . . ? N2 Cu1 O1 168.64(10) . . ? N1 Cu1 O1 90.35(10) . . ? O3 Cu1 O1 77.77(7) . . ? N2 Cu1 O2 94.11(8) . 3 ? N1 Cu1 O2 91.99(8) . 3 ? O3 Cu1 O2 93.31(6) . 3 ? O1 Cu1 O2 91.93(6) . 3 ? N2 Cu1 Cu2 130.61(9) . . ? N1 Cu1 Cu2 129.70(9) . . ? O3 Cu1 Cu2 38.42(5) . . ? O1 Cu1 Cu2 39.40(5) . . ? O2 Cu1 Cu2 91.91(4) 3 . ? O4 Cu2 O2 93.41(7) . . ? O4 Cu2 O3 95.11(8) . . ? O2 Cu2 O3 169.56(7) . . ? O4 Cu2 O1 174.89(8) . . ? O2 Cu2 O1 91.46(7) . . ? O3 Cu2 O1 79.89(8) . . ? O4 Cu2 Cu1 134.73(5) . . ? O2 Cu2 Cu1 131.18(5) . . ? O3 Cu2 Cu1 39.72(5) . . ? O1 Cu2 Cu1 40.22(5) . . ? C2 O1 Cu2 125.40(16) . . ? C2 O1 Cu1 130.11(16) . . ? Cu2 O1 Cu1 100.38(8) . . ? C4 O2 Cu2 122.12(15) . . ? C4 O2 Cu1 116.73(14) . 3 ? Cu2 O2 Cu1 96.43(7) . 3 ? C17 O3 Cu2 127.46(17) . . ? C17 O3 Cu1 130.66(16) . . ? Cu2 O3 Cu1 101.87(8) . . ? C19 O4 Cu2 126.44(16) . . ? C11 N1 C12A 102.0(5) . . ? C11 N1 C12B 125.7(4) . . ? C11 N1 Cu1 123.6(2) . . ? C12A N1 Cu1 134.5(5) . . ? C12B N1 Cu1 110.7(3) . . ? C15 N2 C14B 105.8(4) . . ? C15 N2 C14A 127.0(4) . . ? C15 N2 Cu1 123.6(2) . . ? C14B N2 Cu1 129.8(4) . . ? C14A N2 Cu1 108.9(4) . . ? C2 C1 C10 119.1(3) . . ? C2 C1 C11 123.8(3) . . ? C10 C1 C11 117.1(3) . . ? O1 C2 C1 118.9(3) . . ? O1 C2 C3 121.0(2) . . ? C1 C2 C3 120.1(3) . . ? C4 C3 C2 123.9(2) . . ? C4 C3 C8 118.1(3) . . ? C2 C3 C8 118.0(2) . . ? O2 C4 C5 117.7(2) . . ? O2 C4 C3 123.6(2) . . ? C5 C4 C3 118.7(2) . . ? C6 C5 C4 121.7(3) . . ? C7 C6 C5 120.8(3) . . ? C6 C7 C8 120.4(3) . . ? C7 C8 C9 120.0(3) . . ? C7 C8 C3 120.1(3) . . ? C9 C8 C3 119.9(3) . . ? C10 C9 C8 120.7(3) . . ? C9 C10 C1 122.0(3) . . ? N1 C11 C1 130.1(3) . . ? N1 C12A C13A 103.6(7) . . ? C12A C13A C14A 114.3(9) . . ? C13A C14A N2 115.3(7) . . ? C13B C12B N1 116.7(6) . . ? C12B C13B C14B 113.7(6) . . ? N2 C14B C13B 106.4(5) . . ? N2 C15 C16 129.7(3) . . ? C17 C16 C15 124.9(3) . . ? C17 C16 C25 118.9(3) . . ? C15 C16 C25 116.1(3) . . ? O3 C17 C16 118.7(3) . . ? O3 C17 C18 121.3(2) . . ? C16 C17 C18 119.9(3) . . ? C17 C18 C19 124.0(2) . . ? C17 C18 C23 118.5(3) . . ? C19 C18 C23 117.4(3) . . ? O4 C19 C20 116.2(2) . . ? O4 C19 C18 125.2(2) . . ? C20 C19 C18 118.6(2) . . ? C21 C20 C19 121.8(3) . . ? C22 C21 C20 120.7(3) . . ? C21 C22 C23 120.5(3) . . ? C22 C23 C24 119.4(3) . . ? C22 C23 C18 120.9(3) . . ? C24 C23 C18 119.7(3) . . ? C25 C24 C23 120.9(3) . . ? C24 C25 C16 121.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 Cu2 O4 -8.90(13) . . . . ? N1 Cu1 Cu2 O4 -177.66(12) . . . . ? O3 Cu1 Cu2 O4 -4.76(11) . . . . ? O1 Cu1 Cu2 O4 178.87(11) . . . . ? O2 Cu1 Cu2 O4 88.16(9) 3 . . . ? N2 Cu1 Cu2 O2 -176.80(12) . . . . ? N1 Cu1 Cu2 O2 14.44(12) . . . . ? O3 Cu1 Cu2 O2 -172.66(10) . . . . ? O1 Cu1 Cu2 O2 10.97(10) . . . . ? O2 Cu1 Cu2 O2 -79.74(9) 3 . . . ? N2 Cu1 Cu2 O3 -4.14(13) . . . . ? N1 Cu1 Cu2 O3 -172.90(12) . . . . ? O1 Cu1 Cu2 O3 -176.37(11) . . . . ? O2 Cu1 Cu2 O3 92.92(9) 3 . . . ? N2 Cu1 Cu2 O1 172.22(13) . . . . ? N1 Cu1 Cu2 O1 3.47(11) . . . . ? O3 Cu1 Cu2 O1 176.37(11) . . . . ? O2 Cu1 Cu2 O1 -90.71(9) 3 . . . ? O2 Cu2 O1 C2 29.21(19) . . . . ? O3 Cu2 O1 C2 -156.68(19) . . . . ? Cu1 Cu2 O1 C2 -159.0(2) . . . . ? O2 Cu2 O1 Cu1 -171.76(8) . . . . ? O3 Cu2 O1 Cu1 2.36(7) . . . . ? N2 Cu1 O1 C2 126.2(5) . . . . ? N1 Cu1 O1 C2 -19.7(2) . . . . ? O3 Cu1 O1 C2 155.3(2) . . . . ? O2 Cu1 O1 C2 -111.8(2) 3 . . . ? Cu2 Cu1 O1 C2 157.6(2) . . . . ? N2 Cu1 O1 Cu2 -31.4(5) . . . . ? N1 Cu1 O1 Cu2 -177.33(9) . . . . ? O3 Cu1 O1 Cu2 -2.31(7) . . . . ? O2 Cu1 O1 Cu2 90.67(7) 3 . . . ? O4 Cu2 O2 C4 143.10(18) . . . . ? O3 Cu2 O2 C4 -72.3(5) . . . . ? O1 Cu2 O2 C4 -38.42(18) . . . . ? Cu1 Cu2 O2 C4 -45.5(2) . . . . ? O4 Cu2 O2 Cu1 -89.66(7) . . . 3 ? O3 Cu2 O2 Cu1 55.0(4) . . . 3 ? O1 Cu2 O2 Cu1 88.83(7) . . . 3 ? Cu1 Cu2 O2 Cu1 81.76(7) . . . 3 ? O4 Cu2 O3 C17 -4.5(2) . . . . ? O2 Cu2 O3 C17 -149.1(4) . . . . ? O1 Cu2 O3 C17 176.5(2) . . . . ? Cu1 Cu2 O3 C17 178.8(2) . . . . ? O4 Cu2 O3 Cu1 176.61(8) . . . . ? O2 Cu2 O3 Cu1 32.1(4) . . . . ? O1 Cu2 O3 Cu1 -2.38(7) . . . . ? N2 Cu1 O3 C17 -1.9(2) . . . . ? N1 Cu1 O3 C17 -153.5(4) . . . . ? O1 Cu1 O3 C17 -176.4(2) . . . . ? O2 Cu1 O3 C17 92.3(2) 3 . . . ? Cu2 Cu1 O3 C17 -178.8(2) . . . . ? N2 Cu1 O3 Cu2 176.85(9) . . . . ? N1 Cu1 O3 Cu2 25.3(4) . . . . ? O1 Cu1 O3 Cu2 2.36(7) . . . . ? O2 Cu1 O3 Cu2 -88.90(7) 3 . . . ? O2 Cu2 O4 C19 172.49(19) . . . . ? O3 Cu2 O4 C19 -1.5(2) . . . . ? Cu1 Cu2 O4 C19 1.6(2) . . . . ? N2 Cu1 N1 C11 -161.3(3) . . . . ? O3 Cu1 N1 C11 -10.1(6) . . . . ? O1 Cu1 N1 C11 12.3(3) . . . . ? O2 Cu1 N1 C11 104.2(3) 3 . . . ? Cu2 Cu1 N1 C11 10.1(3) . . . . ? N2 Cu1 N1 C12A 19.6(8) . . . . ? O3 Cu1 N1 C12A 170.8(8) . . . . ? O1 Cu1 N1 C12A -166.8(8) . . . . ? O2 Cu1 N1 C12A -74.9(8) 3 . . . ? Cu2 Cu1 N1 C12A -169.0(8) . . . . ? N2 Cu1 N1 C12B 20.3(4) . . . . ? O3 Cu1 N1 C12B 171.5(5) . . . . ? O1 Cu1 N1 C12B -166.1(4) . . . . ? O2 Cu1 N1 C12B -74.2(4) 3 . . . ? Cu2 Cu1 N1 C12B -168.3(4) . . . . ? N1 Cu1 N2 C15 172.0(3) . . . . ? O3 Cu1 N2 C15 -1.8(3) . . . . ? O1 Cu1 N2 C15 26.6(7) . . . . ? O2 Cu1 N2 C15 -95.3(3) 3 . . . ? Cu2 Cu1 N2 C15 0.7(3) . . . . ? N1 Cu1 N2 C14B -19.5(4) . . . . ? O3 Cu1 N2 C14B 166.7(4) . . . . ? O1 Cu1 N2 C14B -164.9(5) . . . . ? O2 Cu1 N2 C14B 73.2(4) 3 . . . ? Cu2 Cu1 N2 C14B 169.2(4) . . . . ? N1 Cu1 N2 C14A -0.4(5) . . . . ? O3 Cu1 N2 C14A -174.2(5) . . . . ? O1 Cu1 N2 C14A -145.8(6) . . . . ? O2 Cu1 N2 C14A 92.3(5) 3 . . . ? Cu2 Cu1 N2 C14A -171.6(5) . . . . ? Cu2 O1 C2 C1 167.14(17) . . . . ? Cu1 O1 C2 C1 14.5(3) . . . . ? Cu2 O1 C2 C3 -12.6(3) . . . . ? Cu1 O1 C2 C3 -165.18(16) . . . . ? C10 C1 C2 O1 -179.0(2) . . . . ? C11 C1 C2 O1 3.1(4) . . . . ? C10 C1 C2 C3 0.7(4) . . . . ? C11 C1 C2 C3 -177.2(2) . . . . ? O1 C2 C3 C4 -5.6(4) . . . . ? C1 C2 C3 C4 174.7(2) . . . . ? O1 C2 C3 C8 174.8(2) . . . . ? C1 C2 C3 C8 -4.9(3) . . . . ? Cu2 O2 C4 C5 -147.94(18) . . . . ? Cu1 O2 C4 C5 94.4(2) 3 . . . ? Cu2 O2 C4 C3 33.2(3) . . . . ? Cu1 O2 C4 C3 -84.5(2) 3 . . . ? C2 C3 C4 O2 -5.1(4) . . . . ? C8 C3 C4 O2 174.5(2) . . . . ? C2 C3 C4 C5 176.0(2) . . . . ? C8 C3 C4 C5 -4.4(3) . . . . ? O2 C4 C5 C6 -177.6(2) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C7 1.6(4) . . . . ? C5 C6 C7 C8 -1.1(5) . . . . ? C6 C7 C8 C9 177.4(3) . . . . ? C6 C7 C8 C3 -2.1(4) . . . . ? C4 C3 C8 C7 4.9(4) . . . . ? C2 C3 C8 C7 -175.5(2) . . . . ? C4 C3 C8 C9 -174.7(2) . . . . ? C2 C3 C8 C9 5.0(4) . . . . ? C7 C8 C9 C10 179.8(3) . . . . ? C3 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 C1 -3.9(5) . . . . ? C2 C1 C10 C9 3.9(4) . . . . ? C11 C1 C10 C9 -178.1(3) . . . . ? C12A N1 C11 C1 177.8(6) . . . . ? C12B N1 C11 C1 176.6(5) . . . . ? Cu1 N1 C11 C1 -1.5(5) . . . . ? C2 C1 C11 N1 -10.0(5) . . . . ? C10 C1 C11 N1 172.0(3) . . . . ? C11 N1 C12A C13A -172.1(7) . . . . ? C12B N1 C12A C13A 5.5(13) . . . . ? Cu1 N1 C12A C13A 7.1(13) . . . . ? N1 C12A C13A C14A -58.6(11) . . . . ? C12A C13A C14A N2 85.1(12) . . . . ? C15 N2 C14A C13A 145.7(7) . . . . ? C14B N2 C14A C13A 103.5(17) . . . . ? Cu1 N2 C14A C13A -42.3(10) . . . . ? C11 N1 C12B C13B 131.3(5) . . . . ? C12A N1 C12B C13B 128(2) . . . . ? Cu1 N1 C12B C13B -50.3(7) . . . . ? N1 C12B C13B C14B 78.0(8) . . . . ? C15 N2 C14B C13B -151.0(5) . . . . ? C14A N2 C14B C13B -4.8(9) . . . . ? Cu1 N2 C14B C13B 39.0(7) . . . . ? C12B C13B C14B N2 -63.9(7) . . . . ? C14B N2 C15 C16 -167.3(4) . . . . ? C14A N2 C15 C16 174.4(6) . . . . ? Cu1 N2 C15 C16 3.5(5) . . . . ? N2 C15 C16 C17 -1.2(5) . . . . ? N2 C15 C16 C25 177.2(3) . . . . ? Cu2 O3 C17 C16 -174.33(17) . . . . ? Cu1 O3 C17 C16 4.2(3) . . . . ? Cu2 O3 C17 C18 6.1(3) . . . . ? Cu1 O3 C17 C18 -175.37(16) . . . . ? C15 C16 C17 O3 -2.8(4) . . . . ? C25 C16 C17 O3 178.9(2) . . . . ? C15 C16 C17 C18 176.7(2) . . . . ? C25 C16 C17 C18 -1.6(4) . . . . ? O3 C17 C18 C19 -1.3(4) . . . . ? C16 C17 C18 C19 179.1(2) . . . . ? O3 C17 C18 C23 178.4(2) . . . . ? C16 C17 C18 C23 -1.1(3) . . . . ? Cu2 O4 C19 C20 -174.53(17) . . . . ? Cu2 O4 C19 C18 5.9(3) . . . . ? C17 C18 C19 O4 -5.0(4) . . . . ? C23 C18 C19 O4 175.2(2) . . . . ? C17 C18 C19 C20 175.4(2) . . . . ? C23 C18 C19 C20 -4.3(3) . . . . ? O4 C19 C20 C21 -176.9(2) . . . . ? C18 C19 C20 C21 2.7(4) . . . . ? C19 C20 C21 C22 0.8(4) . . . . ? C20 C21 C22 C23 -2.4(5) . . . . ? C21 C22 C23 C24 -179.3(3) . . . . ? C21 C22 C23 C18 0.6(4) . . . . ? C17 C18 C23 C22 -176.9(2) . . . . ? C19 C18 C23 C22 2.8(4) . . . . ? C17 C18 C23 C24 2.9(4) . . . . ? C19 C18 C23 C24 -177.3(2) . . . . ? C22 C23 C24 C25 177.9(3) . . . . ? C18 C23 C24 C25 -1.9(4) . . . . ? C23 C24 C25 C16 -0.9(5) . . . . ? C17 C16 C25 C24 2.7(4) . . . . ? C15 C16 C25 C24 -175.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.329 _refine_diff_density_min -0.828 _refine_diff_density_rms 0.070 data_sad _database_code_depnum_ccdc_archive 'CCDC 273594' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H16 O5' _chemical_formula_weight 276.28 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' 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 4.5003(7) _cell_length_b 13.713(2) _cell_length_c 21.761(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.422(3) _cell_angle_gamma 90.00 _cell_volume 1340.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 1 _cell_measurement_theta_max 22.5 _exptl_crystal_description 'transparent needles' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.369 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9465 _exptl_absorpt_correction_T_max 0.9979 _exptl_absorpt_process_details ; Corrections were done with the SADABS program, utilizing the none merged raw data obtained from the integration process. Integration and final cell refinement were done with SAINT. SADABS reports ratio of Tmin/Tmax = 0.852113 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'Omega and Phi scans' _diffrn_detector_area_resol_mean 80 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12720 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3059 _reflns_number_gt 2126 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker AXS, 2000)' _computing_cell_refinement 'SAINT (Bruker AXS, 2000)' _computing_data_reduction 'SAINT,SADABS (Bruker AXS, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565 ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3059 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 O1 O 0.2665(2) 0.26138(7) 0.19930(4) 0.0270(2) Uani 1 1 d . . . O2 O -0.0587(2) 0.37994(7) 0.12890(5) 0.0308(3) Uani 1 1 d . . . C2 C 0.2760(3) 0.09542(11) 0.17029(7) 0.0297(3) Uani 1 1 d . . . O3 O -0.2481(2) 0.52507(7) 0.08340(5) 0.0336(3) Uani 1 1 d . . . C6 C -0.0482(3) 0.20844(10) 0.11019(6) 0.0248(3) Uani 1 1 d . . . O4 O 0.0786(2) 0.23202(8) 0.29521(4) 0.0358(3) Uani 1 1 d . . . C1 C 0.1645(3) 0.18826(10) 0.16022(6) 0.0247(3) Uani 1 1 d . . . C8 C -0.3844(3) 0.31351(12) 0.04786(7) 0.0317(4) Uani 1 1 d . . . C7 C -0.1703(3) 0.30260(10) 0.09515(6) 0.0260(3) Uani 1 1 d . . . C5 C -0.1460(3) 0.12804(11) 0.07235(6) 0.0289(3) Uani 1 1 d . . . C3 C 0.1764(4) 0.01789(12) 0.13150(8) 0.0357(4) Uani 1 1 d . . . O5 O 0.5823(3) -0.00521(9) 0.23537(6) 0.0561(4) Uani 1 1 d . . . C9 C -0.4804(4) 0.23289(13) 0.01249(7) 0.0359(4) Uani 1 1 d . . . C15 C 0.4958(4) 0.07554(13) 0.22138(8) 0.0371(4) Uani 1 1 d . . . C13 C 0.0577(4) 0.29139(12) 0.24307(7) 0.0293(3) Uani 1 1 d . . . C4 C -0.0269(4) 0.03365(11) 0.08455(8) 0.0346(4) Uani 1 1 d . . . C11 C -0.2418(4) 0.46431(11) 0.13457(8) 0.0332(4) Uani 1 1 d . . . C10 C -0.3615(4) 0.14322(13) 0.02344(7) 0.0354(4) Uani 1 1 d . . . C14 C 0.3197(4) 0.25838(15) 0.33751(8) 0.0422(4) Uani 1 1 d . . . C12 C 0.0338(4) 0.56749(14) 0.07376(10) 0.0435(4) Uani 1 1 d . . . H13A H -0.147(3) 0.2842(11) 0.2241(6) 0.025(4) Uiso 1 1 d . . . H11A H -0.451(4) 0.4434(11) 0.1400(7) 0.031(4) Uiso 1 1 d . . . H11B H -0.155(3) 0.4962(11) 0.1723(7) 0.029(4) Uiso 1 1 d . . . H13B H 0.109(3) 0.3592(12) 0.2539(6) 0.026(4) Uiso 1 1 d . . . H12A H 0.172(4) 0.5184(13) 0.0587(8) 0.045(5) Uiso 1 1 d . . . H4 H -0.093(4) -0.0169(12) 0.0582(7) 0.034(4) Uiso 1 1 d . . . H12B H 0.001(4) 0.6153(13) 0.0412(8) 0.044(5) Uiso 1 1 d . . . H9 H -0.630(4) 0.2436(11) -0.0224(7) 0.035(4) Uiso 1 1 d . . . H3 H 0.262(4) -0.0442(12) 0.1409(7) 0.037(4) Uiso 1 1 d . . . H14A H 0.509(5) 0.2643(13) 0.3173(8) 0.053(5) Uiso 1 1 d . . . H8 H -0.462(3) 0.3763(12) 0.0381(7) 0.031(4) Uiso 1 1 d . . . H14B H 0.276(4) 0.3241(15) 0.3578(9) 0.062(6) Uiso 1 1 d . . . H15 H 0.574(4) 0.1304(14) 0.2457(7) 0.042(5) Uiso 1 1 d . . . H14C H 0.342(4) 0.2095(14) 0.3697(9) 0.057(6) Uiso 1 1 d . . . H10 H -0.424(3) 0.0895(11) -0.0021(7) 0.032(4) Uiso 1 1 d . . . H12C H 0.125(4) 0.5966(14) 0.1117(9) 0.062(6) Uiso 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 O1 0.0255(6) 0.0260(5) 0.0295(5) 0.0000(4) 0.0008(4) -0.0029(4) O2 0.0336(6) 0.0219(5) 0.0360(6) -0.0011(4) -0.0056(5) 0.0020(4) C2 0.0282(8) 0.0274(8) 0.0342(8) 0.0042(6) 0.0086(7) 0.0013(7) O3 0.0273(6) 0.0283(6) 0.0453(6) 0.0064(5) 0.0026(5) 0.0031(5) C6 0.0235(7) 0.0247(8) 0.0269(7) 0.0002(6) 0.0070(6) -0.0034(6) O4 0.0380(6) 0.0409(6) 0.0281(6) 0.0032(5) 0.0000(5) -0.0096(5) C1 0.0242(7) 0.0233(7) 0.0274(7) 0.0004(6) 0.0076(6) -0.0032(6) C8 0.0302(9) 0.0344(9) 0.0304(8) 0.0042(7) 0.0022(7) 0.0014(7) C7 0.0264(8) 0.0271(7) 0.0251(7) -0.0003(6) 0.0046(6) -0.0033(6) C5 0.0288(8) 0.0291(8) 0.0296(8) -0.0032(6) 0.0087(6) -0.0056(7) C3 0.0396(10) 0.0228(8) 0.0458(10) 0.0004(7) 0.0130(8) 0.0024(7) O5 0.0682(9) 0.0404(7) 0.0594(9) 0.0117(6) 0.0004(7) 0.0235(7) C9 0.0337(9) 0.0464(10) 0.0273(8) -0.0003(7) -0.0016(7) -0.0053(8) C15 0.0353(9) 0.0352(9) 0.0417(9) 0.0067(8) 0.0089(8) 0.0075(8) C13 0.0310(9) 0.0295(9) 0.0275(8) -0.0026(6) 0.0020(7) -0.0022(7) C4 0.0393(10) 0.0258(8) 0.0394(9) -0.0082(7) 0.0094(8) -0.0047(7) C11 0.0362(10) 0.0273(8) 0.0364(9) -0.0008(7) 0.0049(7) 0.0052(7) C10 0.0367(10) 0.0375(9) 0.0322(8) -0.0090(7) 0.0035(7) -0.0098(8) C14 0.0447(11) 0.0513(11) 0.0298(9) 0.0008(9) -0.0033(8) -0.0075(9) C12 0.0339(10) 0.0355(10) 0.0617(13) 0.0080(10) 0.0094(9) 0.0005(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 O1 C1 1.3757(17) . ? O1 C13 1.4376(18) . ? O2 C7 1.3686(17) . ? O2 C11 1.4300(18) . ? C2 C1 1.381(2) . ? C2 C3 1.414(2) . ? C2 C15 1.469(2) . ? O3 C11 1.3897(18) . ? O3 C12 1.423(2) . ? C6 C5 1.430(2) . ? C6 C1 1.433(2) . ? C6 C7 1.433(2) . ? O4 C13 1.3950(18) . ? O4 C14 1.427(2) . ? C8 C7 1.375(2) . ? C8 C9 1.401(2) . ? C8 H8 0.948(16) . ? C5 C10 1.412(2) . ? C5 C4 1.420(2) . ? C3 C4 1.347(3) . ? C3 H3 0.951(17) . ? O5 C15 1.207(2) . ? C9 C10 1.356(2) . ? C9 H9 0.995(17) . ? C15 H15 0.974(19) . ? C13 H13A 0.992(15) . ? C13 H13B 0.984(16) . ? C4 H4 0.936(17) . ? C11 H11A 0.999(16) . ? C11 H11B 0.991(16) . ? C10 H10 0.955(16) . ? C14 H14A 0.99(2) . ? C14 H14B 1.03(2) . ? C14 H14C 0.97(2) . ? C12 H12A 0.984(19) . ? C12 H12B 0.970(18) . ? C12 H12C 0.99(2) . ? 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 C1 O1 C13 114.28(11) . . ? C7 O2 C11 118.58(12) . . ? C1 C2 C3 119.95(14) . . ? C1 C2 C15 120.86(14) . . ? C3 C2 C15 119.18(14) . . ? C11 O3 C12 112.80(13) . . ? C5 C6 C1 117.21(13) . . ? C5 C6 C7 117.55(13) . . ? C1 C6 C7 125.24(12) . . ? C13 O4 C14 112.88(13) . . ? O1 C1 C2 117.98(13) . . ? O1 C1 C6 120.80(12) . . ? C2 C1 C6 121.22(13) . . ? C7 C8 C9 120.32(16) . . ? C7 C8 H8 119.9(9) . . ? C9 C8 H8 119.8(9) . . ? O2 C7 C8 122.39(13) . . ? O2 C7 C6 116.87(12) . . ? C8 C7 C6 120.71(13) . . ? C10 C5 C4 120.66(14) . . ? C10 C5 C6 119.63(14) . . ? C4 C5 C6 119.71(14) . . ? C4 C3 C2 120.59(15) . . ? C4 C3 H3 123.6(10) . . ? C2 C3 H3 115.8(10) . . ? C10 C9 C8 120.89(15) . . ? C10 C9 H9 120.6(9) . . ? C8 C9 H9 118.4(9) . . ? O5 C15 C2 123.62(17) . . ? O5 C15 H15 118.1(10) . . ? C2 C15 H15 118.3(10) . . ? O4 C13 O1 110.90(12) . . ? O4 C13 H13A 107.3(8) . . ? O1 C13 H13A 108.8(8) . . ? O4 C13 H13B 110.8(8) . . ? O1 C13 H13B 106.0(8) . . ? H13A C13 H13B 113.1(12) . . ? C3 C4 C5 121.30(15) . . ? C3 C4 H4 121.4(10) . . ? C5 C4 H4 117.2(10) . . ? O3 C11 O2 113.60(12) . . ? O3 C11 H11A 107.0(9) . . ? O2 C11 H11A 109.3(9) . . ? O3 C11 H11B 112.9(9) . . ? O2 C11 H11B 103.1(9) . . ? H11A C11 H11B 110.9(12) . . ? C9 C10 C5 120.81(15) . . ? C9 C10 H10 119.8(9) . . ? C5 C10 H10 119.4(9) . . ? O4 C14 H14A 112.3(11) . . ? O4 C14 H14B 109.9(11) . . ? H14A C14 H14B 108.3(16) . . ? O4 C14 H14C 109.4(11) . . ? H14A C14 H14C 109.0(16) . . ? H14B C14 H14C 108.0(15) . . ? O3 C12 H12A 110.8(10) . . ? O3 C12 H12B 106.7(10) . . ? H12A C12 H12B 106.9(14) . . ? O3 C12 H12C 112.0(12) . . ? H12A C12 H12C 108.4(15) . . ? H12B C12 H12C 112.1(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.212 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.041