# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name R.Gudavarthy _publ_contact_author_email 'rghy7@mail.mst.edu, rakeshvathsal@gmail.com' loop_ _publ_author_name R.Gudavarthy E.Kulp S.Limmer E.Sinn J.A.Switze N.Burla # Attachment '- Cu(II)Dmalate_CCDC_634400.cif' data_sad2 _database_code_depnum_ccdc_archive 'CCDC 634400' #TrackingRef '- Cu(II)Dmalate_CCDC_634400.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(ii)malate enantiomer D' _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 Cu O10, 2(H2 O)' _chemical_formula_sum 'C8 H14 Cu O12' _chemical_formula_weight 365.73 _chemical_absolute_configuration rmad 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' 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) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.591(6) _cell_length_b 10.230(8) _cell_length_c 8.184(6) _cell_angle_alpha 90.00 _cell_angle_beta 92.799(11) _cell_angle_gamma 90.00 _cell_volume 634.8(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(11) _cell_measurement_reflns_used 945 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 28.45 _exptl_crystal_description fragment _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.913 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 1.787 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5351 _exptl_absorpt_correction_T_max 0.7164 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(11) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Smart-Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6530 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.46 _reflns_number_total 3095 _reflns_number_gt 3042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT (Bruker, 2008)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.DFIX Restraints have used for the O-H distances in water molecules as well as temperature factors hydrogens on the water molecules were set to 1.2 times of parent oxygen. ; _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^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.026(10) _refine_ls_number_reflns 3095 _refine_ls_number_parameters 202 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0243 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0661 _refine_ls_wR_factor_gt 0.0659 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.058 _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 0.26975(3) 0.26825(3) 0.25879(3) 0.02705(8) Uani 1 1 d . . . O1 O 0.12698(18) 0.12132(15) 0.31054(18) 0.0283(3) Uani 1 1 d . . . O2 O 0.1354(2) -0.09136(17) 0.3565(2) 0.0410(4) Uani 1 1 d . . . O3 O 0.46601(19) 0.14955(14) 0.3214(2) 0.0316(3) Uani 1 1 d . . . H3C H 0.5620 0.1670 0.3665 0.038 Uiso 1 1 calc R . . O4 O 0.7317(2) -0.13066(19) 0.4851(2) 0.0419(4) Uani 1 1 d . . . O5 O 0.8075(3) -0.0783(2) 0.2354(2) 0.0392(4) Uani 1 1 d . . . H5A H 0.9071 -0.0900 0.2763 0.047 Uiso 1 1 calc R . . O6 O 0.40437(18) 0.41507(15) 0.18154(19) 0.0296(3) Uani 1 1 d . . . O7 O 0.37621(19) 0.62420(16) 0.1101(2) 0.0364(4) Uani 1 1 d . . . O8 O 0.07200(19) 0.37803(14) 0.1834(2) 0.0341(3) Uani 1 1 d . . . H8A H -0.0350 0.3718 0.1665 0.041 Uiso 1 1 calc R . . O9 O -0.2225(2) 0.5845(2) 0.2835(2) 0.0402(5) Uani 1 1 d . . . O10 O -0.2972(2) 0.64511(18) 0.02828(19) 0.0361(4) Uani 1 1 d . . . H10A H -0.3834 0.5968 0.0271 0.043 Uiso 1 1 calc R . . C1 C 0.2085(3) 0.0154(2) 0.3448(2) 0.0267(4) Uani 1 1 d . . . C2 C 0.4093(2) 0.02244(19) 0.3739(2) 0.0252(4) Uani 1 1 d . . . H2A H 0.4388 0.0128 0.4912 0.030 Uiso 1 1 calc R . . C3 C 0.5024(3) -0.0850(2) 0.2810(3) 0.0297(4) Uani 1 1 d . . . H3A H 0.4396 -0.1669 0.2922 0.036 Uiso 1 1 calc R . . H3B H 0.5008 -0.0630 0.1656 0.036 Uiso 1 1 calc R . . C4 C 0.6905(3) -0.10122(19) 0.3456(3) 0.0258(4) Uani 1 1 d . . . C5 C 0.3142(3) 0.5189(2) 0.1575(2) 0.0257(4) Uani 1 1 d . . . C6 C 0.1199(2) 0.51375(19) 0.1980(2) 0.0242(4) Uani 1 1 d . . . H6A H 0.1096 0.5407 0.3121 0.029 Uiso 1 1 calc R . . C7 C 0.0037(3) 0.6011(2) 0.0901(2) 0.0295(4) Uani 1 1 d . . . H7A H 0.0538 0.6883 0.0898 0.035 Uiso 1 1 calc R . . H7B H 0.0009 0.5681 -0.0211 0.035 Uiso 1 1 calc R . . C8 C -0.1818(3) 0.6081(2) 0.1471(3) 0.0260(4) Uani 1 1 d . . . O1W O 0.2228(2) -0.30822(19) 0.5441(2) 0.0427(4) Uani 1 1 d D . . H1A H 0.140(3) -0.337(3) 0.580(4) 0.051 Uiso 1 1 d D . . H1B H 0.210(4) -0.238(2) 0.500(3) 0.051 Uiso 1 1 d D . . O2W O -0.2536(2) 0.3281(2) 0.0983(3) 0.0515(5) Uani 1 1 d D . . H2B H -0.264(4) 0.262(2) 0.043(4) 0.062 Uiso 1 1 d D . . H2C H -0.353(3) 0.348(3) 0.130(4) 0.062 Uiso 1 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 Cu1 0.01970(11) 0.02243(11) 0.03887(13) 0.00366(10) 0.00005(8) 0.00025(12) O1 0.0195(6) 0.0267(7) 0.0388(7) 0.0037(6) 0.0009(5) 0.0005(6) O2 0.0223(7) 0.0298(8) 0.0706(11) 0.0120(8) -0.0007(7) -0.0021(6) O3 0.0202(7) 0.0241(7) 0.0498(9) 0.0042(6) -0.0060(6) -0.0024(5) O4 0.0390(9) 0.0522(10) 0.0343(8) 0.0067(7) -0.0008(7) 0.0051(8) O5 0.0228(7) 0.0543(11) 0.0410(10) 0.0044(8) 0.0048(7) -0.0027(8) O6 0.0201(7) 0.0265(7) 0.0424(8) 0.0041(6) 0.0031(6) 0.0015(6) O7 0.0212(7) 0.0290(8) 0.0590(10) 0.0115(7) 0.0020(7) -0.0004(6) O8 0.0185(7) 0.0248(8) 0.0584(10) 0.0038(7) -0.0057(6) -0.0010(5) O9 0.0298(9) 0.0589(12) 0.0324(8) 0.0030(8) 0.0052(7) 0.0019(7) O10 0.0210(7) 0.0469(9) 0.0404(8) 0.0113(7) 0.0011(6) 0.0010(6) C1 0.0197(9) 0.0295(10) 0.0310(9) 0.0009(7) 0.0022(7) -0.0001(8) C2 0.0191(8) 0.0239(8) 0.0326(9) 0.0008(7) 0.0010(7) 0.0002(7) C3 0.0216(9) 0.0299(9) 0.0374(10) -0.0061(8) 0.0005(8) -0.0005(8) C4 0.0241(9) 0.0193(8) 0.0340(9) -0.0021(7) 0.0012(7) 0.0011(7) C5 0.0200(9) 0.0260(9) 0.0308(9) 0.0003(7) -0.0014(7) 0.0005(7) C6 0.0174(8) 0.0256(9) 0.0296(9) 0.0020(7) -0.0002(7) -0.0007(7) C7 0.0204(9) 0.0339(10) 0.0345(10) 0.0081(8) 0.0041(7) 0.0046(8) C8 0.0199(9) 0.0229(9) 0.0351(10) 0.0008(7) 0.0026(8) 0.0010(7) O1W 0.0326(9) 0.0396(10) 0.0552(11) 0.0093(8) -0.0049(7) 0.0044(7) O2W 0.0243(8) 0.0503(11) 0.0797(14) -0.0297(10) -0.0006(8) -0.0009(7) _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 1.9126(18) . ? Cu1 O6 1.9399(18) . ? Cu1 O8 1.9506(17) . ? Cu1 O3 1.9704(18) . ? Cu1 O4 2.338(2) 2_656 ? O1 C1 1.272(3) . ? O2 C1 1.231(3) . ? O3 C2 1.442(3) . ? O3 H3C 0.8200 . ? O4 C4 1.207(3) . ? O4 Cu1 2.338(2) 2_646 ? O5 C4 1.317(3) . ? O5 H5A 0.8200 . ? O6 C5 1.273(3) . ? O7 C5 1.245(3) . ? O8 C6 1.439(3) . ? O8 H8A 0.8200 . ? O9 C8 1.197(3) . ? O10 C8 1.332(3) . ? O10 H10A 0.8200 . ? C1 C2 1.533(3) . ? C2 C3 1.530(3) . ? C2 H2A 0.9800 . ? C3 C4 1.508(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.529(3) . ? C6 C7 1.509(3) . ? C6 H6A 0.9800 . ? C7 C8 1.507(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O1W H1A 0.767(16) . ? O1W H1B 0.803(17) . ? O2W H2B 0.810(17) . ? O2W H2C 0.833(17) . ? 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 O6 173.66(7) . . ? O1 Cu1 O8 94.98(8) . . ? O6 Cu1 O8 81.99(8) . . ? O1 Cu1 O3 83.54(8) . . ? O6 Cu1 O3 99.10(8) . . ? O8 Cu1 O3 175.98(7) . . ? O1 Cu1 O4 96.99(8) . 2_656 ? O6 Cu1 O4 88.58(8) . 2_656 ? O8 Cu1 O4 89.53(8) . 2_656 ? O3 Cu1 O4 94.36(7) . 2_656 ? C1 O1 Cu1 116.32(14) . . ? C2 O3 Cu1 113.58(12) . . ? C2 O3 H3C 109.5 . . ? Cu1 O3 H3C 128.8 . . ? C4 O4 Cu1 161.10(17) . 2_646 ? C4 O5 H5A 109.5 . . ? C5 O6 Cu1 114.10(14) . . ? C6 O8 Cu1 110.00(12) . . ? C6 O8 H8A 109.5 . . ? Cu1 O8 H8A 138.5 . . ? C8 O10 H10A 109.5 . . ? O2 C1 O1 123.82(19) . . ? O2 C1 C2 118.56(19) . . ? O1 C1 C2 117.62(18) . . ? O3 C2 C3 110.36(16) . . ? O3 C2 C1 107.78(16) . . ? C3 C2 C1 111.67(17) . . ? O3 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? C4 C3 C2 110.94(17) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.0 . . ? O4 C4 O5 122.7(2) . . ? O4 C4 C3 123.80(19) . . ? O5 C4 C3 113.53(19) . . ? O7 C5 O6 124.15(19) . . ? O7 C5 C6 118.71(18) . . ? O6 C5 C6 117.07(18) . . ? O8 C6 C7 112.62(16) . . ? O8 C6 C5 104.92(16) . . ? C7 C6 C5 113.28(16) . . ? O8 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C8 C7 C6 112.05(17) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O9 C8 O10 123.2(2) . . ? O9 C8 C7 124.49(19) . . ? O10 C8 C7 112.30(18) . . ? H1A O1W H1B 116(2) . . ? H2B O2W H2C 108(2) . . ? 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 O8 Cu1 O1 C1 170.27(15) . . . . ? O3 Cu1 O1 C1 -5.97(15) . . . . ? O4 Cu1 O1 C1 -99.60(15) 2_656 . . . ? O1 Cu1 O3 C2 -1.12(13) . . . . ? O6 Cu1 O3 C2 -175.30(13) . . . . ? O4 Cu1 O3 C2 95.44(14) 2_656 . . . ? O8 Cu1 O6 C5 15.38(15) . . . . ? O3 Cu1 O6 C5 -168.53(15) . . . . ? O4 Cu1 O6 C5 -74.34(15) 2_656 . . . ? O1 Cu1 O8 C6 155.80(13) . . . . ? O6 Cu1 O8 C6 -29.81(13) . . . . ? O4 Cu1 O8 C6 58.82(13) 2_656 . . . ? Cu1 O1 C1 O2 -168.66(18) . . . . ? Cu1 O1 C1 C2 11.6(2) . . . . ? Cu1 O3 C2 C3 128.64(15) . . . . ? Cu1 O3 C2 C1 6.46(19) . . . . ? O2 C1 C2 O3 168.52(19) . . . . ? O1 C1 C2 O3 -11.8(3) . . . . ? O2 C1 C2 C3 47.1(3) . . . . ? O1 C1 C2 C3 -133.1(2) . . . . ? O3 C2 C3 C4 76.0(2) . . . . ? C1 C2 C3 C4 -164.18(17) . . . . ? Cu1 O4 C4 O5 -141.9(4) 2_646 . . . ? Cu1 O4 C4 C3 39.1(6) 2_646 . . . ? C2 C3 C4 O4 60.2(3) . . . . ? C2 C3 C4 O5 -118.8(2) . . . . ? Cu1 O6 C5 O7 179.03(17) . . . . ? Cu1 O6 C5 C6 2.1(2) . . . . ? Cu1 O8 C6 C7 159.52(13) . . . . ? Cu1 O8 C6 C5 35.88(17) . . . . ? O7 C5 C6 O8 157.53(19) . . . . ? O6 C5 C6 O8 -25.4(2) . . . . ? O7 C5 C6 C7 34.3(3) . . . . ? O6 C5 C6 C7 -148.58(19) . . . . ? O8 C6 C7 C8 68.9(2) . . . . ? C5 C6 C7 C8 -172.26(17) . . . . ? C6 C7 C8 O9 22.2(3) . . . . ? C6 C7 C8 O10 -158.43(18) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 28.46 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.349 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.065 # Attachment '- Cu(II)Lmalate_CCDC_634735.cif' data_sad3 _database_code_depnum_ccdc_archive 'CCDC 634735' #TrackingRef '- Cu(II)Lmalate_CCDC_634735.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(ii)malate enantiomer L' _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 Cu O10, 2(H2 O)' _chemical_formula_sum 'C8 H14 Cu O12' _chemical_formula_weight 365.73 _chemical_absolute_configuration rmad 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' 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) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.584(4) _cell_length_b 10.214(5) _cell_length_c 8.169(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.778(7) _cell_angle_gamma 90.00 _cell_volume 632.1(5) _cell_formula_units_Z 2 _cell_measurement_temperature 298(11) _cell_measurement_reflns_used 953 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 28.31 _exptl_crystal_description fragment _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.921 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 1.794 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5339 _exptl_absorpt_correction_T_max 0.7746 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(11) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Smart-Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6473 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3072 _reflns_number_gt 3022 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT (Bruker, 2008)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.DFIX Restraints have used for the O-H distances in water molecules as well as temperature factors hydrogens on the water molecules were set to 1.2 times of parent oxygen. ; _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^)+(0.0436P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(9) _refine_ls_number_reflns 3072 _refine_ls_number_parameters 202 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0245 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0666 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.027 _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 0.73009(3) 0.73173(3) 0.74118(3) 0.02647(8) Uani 1 1 d . . . O1 O 0.87260(19) 0.87882(15) 0.68944(19) 0.0277(3) Uani 1 1 d . . . O2 O 0.8645(2) 1.09149(17) 0.6441(2) 0.0399(4) Uani 1 1 d . . . O3 O 0.5337(2) 0.85056(15) 0.6784(2) 0.0308(3) Uani 1 1 d . . . H3C H 0.4377 0.8332 0.6331 0.037 Uiso 1 1 calc R . . O4 O 0.2683(2) 1.13065(19) 0.5153(2) 0.0410(4) Uani 1 1 d . . . O5 O 0.1921(3) 1.0781(2) 0.7651(2) 0.0386(4) Uani 1 1 d . . . H5A H 0.0924 1.0898 0.7243 0.046 Uiso 1 1 calc R . . O6 O 0.59581(18) 0.58485(15) 0.81867(19) 0.0290(3) Uani 1 1 d . . . O7 O 0.6239(2) 0.37543(17) 0.8897(2) 0.0354(4) Uani 1 1 d . . . O8 O 0.92785(19) 0.62213(15) 0.8165(2) 0.0333(3) Uani 1 1 d . . . H8A H 1.0350 0.6285 0.8334 0.040 Uiso 1 1 calc R . . O9 O 1.2225(2) 0.4155(2) 0.7162(2) 0.0393(5) Uani 1 1 d . . . O10 O 1.2975(2) 0.35491(18) 0.9717(2) 0.0351(4) Uani 1 1 d . . . H10A H 1.3839 0.4033 0.9729 0.042 Uiso 1 1 calc R . . C1 C 0.7912(3) 0.9846(2) 0.6553(3) 0.0262(4) Uani 1 1 d . . . C2 C 0.5905(2) 0.9778(2) 0.6263(3) 0.0249(4) Uani 1 1 d . . . H2A H 0.5611 0.9876 0.5088 0.030 Uiso 1 1 calc R . . C3 C 0.4971(3) 1.0853(2) 0.7192(3) 0.0290(4) Uani 1 1 d . . . H3A H 0.4987 1.0634 0.8348 0.035 Uiso 1 1 calc R . . H3B H 0.5597 1.1674 0.7078 0.035 Uiso 1 1 calc R . . C4 C 0.3090(3) 1.1011(2) 0.6545(3) 0.0250(4) Uani 1 1 d . . . C5 C 0.6861(2) 0.4809(2) 0.8424(2) 0.0241(4) Uani 1 1 d . . . C6 C 0.8802(2) 0.48623(19) 0.8019(2) 0.0229(4) Uani 1 1 d . . . H6A H 0.8906 0.4592 0.6876 0.028 Uiso 1 1 calc R . . C7 C 0.9966(3) 0.3990(2) 0.9100(2) 0.0282(4) Uani 1 1 d . . . H7A H 0.9993 0.4321 1.0214 0.034 Uiso 1 1 calc R . . H7B H 0.9468 0.3116 0.9105 0.034 Uiso 1 1 calc R . . C8 C 1.1822(3) 0.3921(2) 0.8531(3) 0.0248(4) Uani 1 1 d . . . O1W O 0.7773(2) 1.3083(2) 0.4560(2) 0.0421(4) Uani 1 1 d D . . H1A H 0.862(3) 1.335(3) 0.419(4) 0.051 Uiso 1 1 d D . . H1B H 0.791(4) 1.239(2) 0.503(3) 0.051 Uiso 1 1 d D . . O2W O 1.2533(2) 0.6721(2) 0.9014(3) 0.0509(5) Uani 1 1 d D . . H2B H 1.262(4) 0.741(2) 0.955(4) 0.061 Uiso 1 1 d D . . H2C H 1.354(3) 0.653(3) 0.874(4) 0.061 Uiso 1 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 Cu1 0.01854(11) 0.02223(11) 0.03848(13) 0.00370(10) -0.00016(8) 0.00026(12) O1 0.0186(7) 0.0260(7) 0.0383(7) 0.0043(6) 0.0005(5) 0.0008(5) O2 0.0209(7) 0.0295(8) 0.0690(11) 0.0115(8) -0.0010(7) -0.0020(6) O3 0.0194(7) 0.0238(7) 0.0485(9) 0.0031(6) -0.0066(6) -0.0018(5) O4 0.0379(9) 0.0499(10) 0.0347(8) 0.0059(7) -0.0022(7) 0.0044(8) O5 0.0213(8) 0.0550(11) 0.0397(10) 0.0041(8) 0.0045(7) -0.0035(8) O6 0.0188(7) 0.0262(7) 0.0421(8) 0.0039(6) 0.0030(6) 0.0015(6) O7 0.0197(7) 0.0289(8) 0.0576(10) 0.0117(7) 0.0015(6) -0.0007(6) O8 0.0179(7) 0.0246(8) 0.0566(10) 0.0038(7) -0.0065(6) -0.0014(5) O9 0.0280(9) 0.0588(13) 0.0313(8) 0.0023(8) 0.0052(7) 0.0022(7) O10 0.0189(7) 0.0453(9) 0.0411(9) 0.0118(7) -0.0003(6) 0.0007(6) C1 0.0184(9) 0.0285(10) 0.0317(10) 0.0019(8) 0.0027(7) -0.0005(7) C2 0.0190(9) 0.0233(9) 0.0323(9) 0.0014(7) 0.0002(7) 0.0011(7) C3 0.0206(9) 0.0298(10) 0.0366(10) -0.0064(8) -0.0004(8) -0.0006(8) C4 0.0229(9) 0.0191(9) 0.0330(9) -0.0025(7) 0.0011(7) 0.0006(7) C5 0.0190(9) 0.0242(9) 0.0289(9) 0.0004(7) -0.0012(7) 0.0004(7) C6 0.0167(8) 0.0239(9) 0.0281(9) 0.0023(7) 0.0002(6) -0.0010(7) C7 0.0190(9) 0.0317(10) 0.0341(10) 0.0079(8) 0.0028(7) 0.0044(7) C8 0.0181(9) 0.0217(9) 0.0345(10) 0.0007(7) 0.0014(8) 0.0005(7) O1W 0.0304(9) 0.0390(10) 0.0563(11) 0.0089(8) -0.0054(8) 0.0044(7) O2W 0.0230(8) 0.0483(11) 0.0811(15) -0.0300(10) -0.0012(8) -0.0006(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 Cu1 O1 1.9101(16) . ? Cu1 O6 1.9369(17) . ? Cu1 O8 1.9473(16) . ? Cu1 O3 1.9698(17) . ? Cu1 O4 2.336(2) 2_646 ? O1 C1 1.269(3) . ? O2 C1 1.230(3) . ? O3 C2 1.440(3) . ? O3 H3C 0.8200 . ? O4 C4 1.202(3) . ? O4 Cu1 2.336(2) 2_656 ? O5 C4 1.317(3) . ? O5 H5A 0.8200 . ? O6 C5 1.273(3) . ? O7 C5 1.245(3) . ? O8 C6 1.438(3) . ? O8 H8A 0.8200 . ? O9 C8 1.198(3) . ? O10 C8 1.329(3) . ? O10 H10A 0.8200 . ? C1 C2 1.531(3) . ? C2 C3 1.528(3) . ? C2 H2A 0.9800 . ? C3 C4 1.506(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C5 C6 1.526(3) . ? C6 C7 1.509(3) . ? C6 H6A 0.9800 . ? C7 C8 1.505(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O1W H1A 0.777(16) . ? O1W H1B 0.805(17) . ? O2W H2B 0.829(18) . ? O2W H2C 0.825(17) . ? 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 O6 173.60(7) . . ? O1 Cu1 O8 94.98(7) . . ? O6 Cu1 O8 81.98(7) . . ? O1 Cu1 O3 83.48(7) . . ? O6 Cu1 O3 99.18(7) . . ? O8 Cu1 O3 175.98(7) . . ? O1 Cu1 O4 96.98(7) . 2_646 ? O6 Cu1 O4 88.66(7) . 2_646 ? O8 Cu1 O4 89.53(7) . 2_646 ? O3 Cu1 O4 94.33(7) . 2_646 ? C1 O1 Cu1 116.36(14) . . ? C2 O3 Cu1 113.59(12) . . ? C2 O3 H3C 109.5 . . ? Cu1 O3 H3C 128.9 . . ? C4 O4 Cu1 161.24(17) . 2_656 ? C4 O5 H5A 109.5 . . ? C5 O6 Cu1 114.10(13) . . ? C6 O8 Cu1 110.01(12) . . ? C6 O8 H8A 109.5 . . ? Cu1 O8 H8A 138.5 . . ? C8 O10 H10A 109.5 . . ? O2 C1 O1 123.74(19) . . ? O2 C1 C2 118.55(19) . . ? O1 C1 C2 117.71(18) . . ? O3 C2 C3 110.49(16) . . ? O3 C2 C1 107.73(16) . . ? C3 C2 C1 111.83(17) . . ? O3 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C4 C3 C2 110.90(17) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.0 . . ? O4 C4 O5 122.9(2) . . ? O4 C4 C3 123.7(2) . . ? O5 C4 C3 113.44(18) . . ? O7 C5 O6 124.04(19) . . ? O7 C5 C6 118.85(18) . . ? O6 C5 C6 117.04(18) . . ? O8 C6 C7 112.56(16) . . ? O8 C6 C5 104.93(16) . . ? C7 C6 C5 113.28(16) . . ? O8 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C8 C7 C6 112.08(17) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? O9 C8 O10 123.3(2) . . ? O9 C8 C7 124.33(19) . . ? O10 C8 C7 112.36(18) . . ? H1A O1W H1B 114(3) . . ? H2B O2W H2C 107(2) . . ? 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 O8 Cu1 O1 C1 -170.23(15) . . . . ? O3 Cu1 O1 C1 6.05(15) . . . . ? O4 Cu1 O1 C1 99.64(16) 2_646 . . . ? O1 Cu1 O3 C2 0.94(13) . . . . ? O6 Cu1 O3 C2 175.06(13) . . . . ? O4 Cu1 O3 C2 -95.60(14) 2_646 . . . ? O8 Cu1 O6 C5 -15.52(15) . . . . ? O3 Cu1 O6 C5 168.37(15) . . . . ? O4 Cu1 O6 C5 74.20(15) 2_646 . . . ? O1 Cu1 O8 C6 -155.81(13) . . . . ? O6 Cu1 O8 C6 29.86(13) . . . . ? O4 Cu1 O8 C6 -58.85(14) 2_646 . . . ? Cu1 O1 C1 O2 168.52(18) . . . . ? Cu1 O1 C1 C2 -11.6(2) . . . . ? Cu1 O3 C2 C3 -128.64(14) . . . . ? Cu1 O3 C2 C1 -6.2(2) . . . . ? O2 C1 C2 O3 -168.53(19) . . . . ? O1 C1 C2 O3 11.6(3) . . . . ? O2 C1 C2 C3 -46.9(3) . . . . ? O1 C1 C2 C3 133.2(2) . . . . ? O3 C2 C3 C4 -75.7(2) . . . . ? C1 C2 C3 C4 164.32(18) . . . . ? Cu1 O4 C4 O5 142.0(4) 2_656 . . . ? Cu1 O4 C4 C3 -38.7(6) 2_656 . . . ? C2 C3 C4 O4 -60.5(3) . . . . ? C2 C3 C4 O5 118.9(2) . . . . ? Cu1 O6 C5 O7 -178.89(17) . . . . ? Cu1 O6 C5 C6 -1.9(2) . . . . ? Cu1 O8 C6 C7 -159.50(13) . . . . ? Cu1 O8 C6 C5 -35.88(17) . . . . ? O7 C5 C6 O8 -157.64(19) . . . . ? O6 C5 C6 O8 25.2(2) . . . . ? O7 C5 C6 C7 -34.5(3) . . . . ? O6 C5 C6 C7 148.39(18) . . . . ? O8 C6 C7 C8 -68.9(2) . . . . ? C5 C6 C7 C8 172.27(17) . . . . ? C6 C7 C8 O9 -22.3(3) . . . . ? C6 C7 C8 O10 158.66(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.428 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.067 data_sad _database_code_depnum_ccdc_archive 'CCDC 634933' #TrackingRef '- Cu(II)DLmalate_CCDC_634933.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cu(ii)malate racemic DL' _chemical_melting_point ? _chemical_formula_moiety 'C8 H14 Cu O12' _chemical_formula_sum 'C8 H14 Cu O12' _chemical_formula_weight 365.73 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' 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)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 8.478(6) _cell_length_b 7.430(5) _cell_length_c 10.295(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.581(9) _cell_angle_gamma 90.00 _cell_volume 632.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(11) _cell_measurement_reflns_used 4859 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 28.37 _exptl_crystal_description fragment _exptl_crystal_colour blue _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 374 _exptl_absorpt_coefficient_mu 1.792 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3669 _exptl_absorpt_correction_T_max 0.4678 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(11) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Smart-Apex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6116 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 28.37 _reflns_number_total 1556 _reflns_number_gt 1448 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT (Bruker, 2008)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. DFIX Restraints have used for the O-H distances in water molecule as well as temperature factors hydrogens on the water molecules were set to 1.2 times of parent oxygen. ; _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^)+(0.0444P)^2^+0.2266P] 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 1556 _refine_ls_number_parameters 103 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.130 _refine_ls_restrained_S_all 1.137 _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 0.5000 0.5000 0.0000 0.02712(12) Uani 1 2 d S . . O1 O 0.53769(16) 0.30566(18) -0.11108(12) 0.0309(3) Uani 1 1 d . . . O2 O 0.66974(19) 0.05066(19) -0.11533(13) 0.0366(3) Uani 1 1 d . . . O3 O 0.66184(15) 0.37595(17) 0.13425(12) 0.0285(3) Uani 1 1 d . . . H3C H 0.6713 0.3790 0.2152 0.034 Uiso 1 1 calc R . . O4 O 0.89470(17) 0.1002(2) 0.35178(14) 0.0391(3) Uani 1 1 d . . . O5 O 1.11283(17) 0.2163(2) 0.29631(15) 0.0448(4) Uani 1 1 d . . . H5A H 1.1568 0.1859 0.3721 0.054 Uiso 1 1 calc R . . C1 C 0.6316(2) 0.1830(2) -0.05495(16) 0.0256(3) Uani 1 1 d . . . C2 C 0.7025(2) 0.1998(2) 0.09528(16) 0.0251(3) Uani 1 1 d . . . H2A H 0.6549 0.1083 0.1436 0.030 Uiso 1 1 calc R . . C3 C 0.8851(2) 0.1770(3) 0.12334(18) 0.0309(4) Uani 1 1 d . . . H3A H 0.9106 0.0702 0.0777 0.037 Uiso 1 1 calc R . . H3B H 0.9319 0.2796 0.0873 0.037 Uiso 1 1 calc R . . C4 C 0.9614(2) 0.1603(2) 0.26934(18) 0.0280(3) Uani 1 1 d . . . O1W O 0.27253(17) 0.3175(2) 0.05092(15) 0.0347(3) Uani 1 1 d D . . H1A H 0.299(3) 0.222(2) 0.084(2) 0.042 Uiso 1 1 d D . . H1B H 0.242(3) 0.383(3) 0.099(2) 0.042 Uiso 1 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 Cu1 0.02932(19) 0.0317(2) 0.01771(17) -0.00237(10) -0.00054(12) 0.00850(11) O1 0.0354(7) 0.0357(7) 0.0184(6) -0.0027(5) -0.0008(5) 0.0075(5) O2 0.0546(9) 0.0302(6) 0.0229(6) -0.0028(5) 0.0039(6) 0.0078(6) O3 0.0357(6) 0.0317(6) 0.0156(5) -0.0012(5) 0.0001(5) 0.0078(5) O4 0.0382(7) 0.0526(9) 0.0261(7) 0.0022(6) 0.0059(5) -0.0043(6) O5 0.0322(7) 0.0632(10) 0.0348(8) 0.0142(7) -0.0017(6) -0.0047(7) C1 0.0273(8) 0.0295(8) 0.0193(7) -0.0018(6) 0.0032(6) -0.0015(6) C2 0.0288(8) 0.0266(8) 0.0190(7) -0.0002(6) 0.0030(6) 0.0017(6) C3 0.0292(8) 0.0399(10) 0.0229(8) 0.0023(7) 0.0042(6) 0.0051(7) C4 0.0287(8) 0.0280(8) 0.0253(8) 0.0009(6) 0.0019(6) 0.0058(6) O1W 0.0361(7) 0.0349(7) 0.0336(7) 0.0032(6) 0.0084(6) 0.0042(6) _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 1.9115(15) 3_665 ? Cu1 O1 1.9115(15) . ? Cu1 O3 1.9536(14) 3_665 ? Cu1 O3 1.9536(14) . ? Cu1 O1W 2.5047(19) . ? O1 C1 1.264(2) . ? O2 C1 1.243(2) . ? O3 C2 1.433(2) . ? O3 H3C 0.8200 . ? O4 C4 1.203(2) . ? O5 C4 1.321(2) . ? O5 H5A 0.8200 . ? C1 C2 1.537(2) . ? C2 C3 1.522(3) . ? C2 H2A 0.9800 . ? C3 C4 1.506(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? O1W H1A 0.797(16) . ? O1W H1B 0.779(16) . ? 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 180.00(6) 3_665 . ? O1 Cu1 O3 83.32(7) 3_665 3_665 ? O1 Cu1 O3 96.68(7) . 3_665 ? O1 Cu1 O3 96.68(7) 3_665 . ? O1 Cu1 O3 83.32(7) . . ? O3 Cu1 O3 180.00(7) 3_665 . ? O1 Cu1 O1W 92.70(7) 3_665 . ? O1 Cu1 O1W 87.30(7) . . ? O3 Cu1 O1W 87.09(7) 3_665 . ? O3 Cu1 O1W 92.91(7) . . ? C1 O1 Cu1 116.22(12) . . ? C2 O3 Cu1 114.05(10) . . ? C2 O3 H3C 109.5 . . ? Cu1 O3 H3C 127.2 . . ? C4 O5 H5A 109.5 . . ? O2 C1 O1 123.24(16) . . ? O2 C1 C2 118.70(15) . . ? O1 C1 C2 118.06(15) . . ? O3 C2 C3 110.20(14) . . ? O3 C2 C1 106.91(13) . . ? C3 C2 C1 109.90(14) . . ? O3 C2 H2A 109.9 . . ? C3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? C4 C3 C2 113.36(15) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? O4 C4 O5 123.59(17) . . ? O4 C4 C3 124.66(17) . . ? O5 C4 C3 111.73(16) . . ? Cu1 O1W H1A 114.3(19) . . ? Cu1 O1W H1B 100(2) . . ? H1A O1W H1B 113(2) . . ? 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 O3 Cu1 O1 C1 -174.95(13) 3_665 . . . ? O3 Cu1 O1 C1 5.05(13) . . . . ? O1W Cu1 O1 C1 -88.20(14) . . . . ? O1 Cu1 O3 C2 169.52(11) 3_665 . . . ? O1 Cu1 O3 C2 -10.48(11) . . . . ? O1W Cu1 O3 C2 76.46(12) . . . . ? Cu1 O1 C1 O2 -178.42(14) . . . . ? Cu1 O1 C1 C2 1.2(2) . . . . ? Cu1 O3 C2 C3 132.15(12) . . . . ? Cu1 O3 C2 C1 12.74(16) . . . . ? O2 C1 C2 O3 170.39(16) . . . . ? O1 C1 C2 O3 -9.3(2) . . . . ? O2 C1 C2 C3 50.8(2) . . . . ? O1 C1 C2 C3 -128.86(17) . . . . ? O3 C2 C3 C4 72.15(19) . . . . ? C1 C2 C3 C4 -170.28(15) . . . . ? C2 C3 C4 O4 28.2(3) . . . . ? C2 C3 C4 O5 -153.15(17) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.460 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.085