# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_cupurpbm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 Cu N2 O10' _chemical_formula_weight 581.96 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.118(3) _cell_length_b 11.051(3) _cell_length_c 21.051(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.029(5) _cell_angle_gamma 90.00 _cell_volume 2324.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Purple _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 1.007 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9477 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0533 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.73 _reflns_number_total 2364 _reflns_number_gt 1630 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0613P)^2^+3.8083P] 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 2364 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 0.25545(5) 0.2500 0.0258(2) Uani 1 2 d S . . O1 O 0.4010(3) 0.0419(3) 0.04890(13) 0.0494(8) Uani 1 1 d . . . O2 O 0.3415(3) 0.0171(3) -0.05651(14) 0.0482(8) Uani 1 1 d . . . H2A H 0.419(5) -0.007(4) -0.050(2) 0.050(15) Uiso 1 1 d . . . O3 O 0.0809(2) 0.2469(2) 0.17112(11) 0.0286(6) Uani 1 1 d . . . O4 O -0.1328(3) 0.2426(2) 0.12932(13) 0.0356(6) Uani 1 1 d . . . O5 O -0.1134(4) 0.1767(4) -0.11065(15) 0.0651(11) Uani 1 1 d . . . H5 H -0.183(6) 0.206(5) -0.108(3) 0.077(19) Uiso 1 1 d . . . N1 N 0.0000 0.0744(3) 0.2500 0.0280(10) Uani 1 2 d S . . N2 N 0.0000 0.4364(3) 0.2500 0.0264(10) Uani 1 2 d S . . C1 C -0.0482(5) 0.4996(3) 0.1976(2) 0.0444(11) Uani 1 1 d . . . H1 H -0.0825 0.4575 0.1604 0.053 Uiso 1 1 calc R . . C2 C -0.0495(4) 0.6238(3) 0.19571(19) 0.0428(11) Uani 1 1 d . . . H2 H -0.0839 0.6639 0.1579 0.051 Uiso 1 1 calc R . . C3 C 0.0000 0.6888(4) 0.2500 0.0281(12) Uani 1 2 d S . . C4 C 0.0000 -0.1764(4) 0.2500 0.0258(11) Uani 1 2 d S . . C5 C -0.1151(4) -0.1116(3) 0.22745(19) 0.0351(9) Uani 1 1 d . . . H5A H -0.1942 -0.1517 0.2115 0.042 Uiso 1 1 calc R . . C6 C -0.1111(4) 0.0122(3) 0.22892(19) 0.0347(9) Uani 1 1 d . . . H6 H -0.1894 0.0548 0.2146 0.042 Uiso 1 1 calc R . . C7 C -0.0303(4) 0.1669(4) -0.05350(19) 0.0398(10) Uani 1 1 d . . . C8 C -0.0630(4) 0.2064(4) 0.00448(19) 0.0372(9) Uani 1 1 d . . . H8 H -0.1458 0.2423 0.0056 0.045 Uiso 1 1 calc R . . C9 C 0.0268(4) 0.1927(3) 0.06100(18) 0.0287(8) Uani 1 1 d . . . C10 C 0.1500(4) 0.1414(3) 0.05934(18) 0.0311(8) Uani 1 1 d . . . H10 H 0.2111 0.1331 0.0970 0.037 Uiso 1 1 calc R . . C11 C 0.1830(4) 0.1019(3) 0.00108(17) 0.0302(8) Uani 1 1 d . . . C12 C 0.0931(4) 0.1137(4) -0.05489(18) 0.0365(9) Uani 1 1 d . . . H12 H 0.1152 0.0859 -0.0936 0.044 Uiso 1 1 calc R . . C13 C 0.3179(4) 0.0506(3) 0.00031(18) 0.0342(9) Uani 1 1 d . . . C14 C -0.0129(4) 0.2315(3) 0.12390(17) 0.0277(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0334(4) 0.0200(3) 0.0244(4) 0.000 0.0059(3) 0.000 O1 0.0409(17) 0.079(2) 0.0281(16) -0.0020(15) 0.0041(14) 0.0199(16) O2 0.0386(18) 0.074(2) 0.0323(17) -0.0123(15) 0.0069(14) 0.0152(16) O3 0.0327(14) 0.0300(13) 0.0239(13) -0.0033(11) 0.0071(11) -0.0003(11) O4 0.0302(15) 0.0430(15) 0.0355(15) -0.0020(12) 0.0107(12) 0.0059(12) O5 0.041(2) 0.123(3) 0.0302(18) -0.0051(18) -0.0002(16) 0.025(2) N1 0.034(3) 0.024(2) 0.027(2) 0.000 0.007(2) 0.000 N2 0.042(3) 0.0199(19) 0.019(2) 0.000 0.009(2) 0.000 C1 0.069(3) 0.0259(19) 0.032(2) -0.0036(17) -0.008(2) -0.0009(19) C2 0.067(3) 0.0238(19) 0.033(2) 0.0052(16) -0.007(2) 0.0010(19) C3 0.034(3) 0.024(2) 0.027(3) 0.000 0.005(2) 0.000 C4 0.039(3) 0.022(2) 0.017(3) 0.000 0.005(2) 0.000 C5 0.039(2) 0.0261(18) 0.039(2) 0.0004(16) 0.0012(19) -0.0036(17) C6 0.034(2) 0.0310(19) 0.038(2) 0.0042(16) 0.0013(19) 0.0074(17) C7 0.036(2) 0.051(2) 0.030(2) -0.0036(18) -0.0028(18) 0.0033(19) C8 0.029(2) 0.051(2) 0.032(2) 0.0003(18) 0.0067(18) 0.0038(18) C9 0.029(2) 0.0264(17) 0.031(2) -0.0013(15) 0.0061(17) -0.0013(15) C10 0.034(2) 0.0320(19) 0.026(2) -0.0001(15) 0.0019(16) 0.0011(16) C11 0.030(2) 0.036(2) 0.026(2) -0.0005(16) 0.0093(16) 0.0010(17) C12 0.036(2) 0.053(2) 0.021(2) -0.0041(18) 0.0079(17) 0.0004(19) C13 0.037(2) 0.039(2) 0.027(2) -0.0025(17) 0.0068(18) 0.0025(18) C14 0.033(2) 0.0239(17) 0.027(2) 0.0031(14) 0.0077(17) 0.0001(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.965(2) . ? Cu1 O3 1.965(2) 2 ? Cu1 N2 2.000(4) . ? Cu1 N1 2.001(4) . ? O1 C13 1.221(5) . ? O2 C13 1.309(4) . ? O2 H2A 0.82(5) . ? O3 C14 1.274(4) . ? O4 C14 1.242(4) . ? O5 C7 1.360(5) . ? O5 H5 0.79(6) . ? N1 C6 1.333(4) . ? N1 C6 1.333(4) 2 ? N2 C1 1.332(4) 2 ? N2 C1 1.332(4) . ? C1 C2 1.373(5) . ? C1 H1 0.9300 . ? C2 C3 1.376(5) . ? C2 H2 0.9300 . ? C3 C2 1.376(5) 2 ? C3 C4 1.489(6) 1_565 ? C4 C5 1.386(4) 2 ? C4 C5 1.386(4) . ? C4 C3 1.489(6) 1_545 ? C5 C6 1.368(5) . ? C5 H5A 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.384(6) . ? C7 C12 1.385(6) . ? C8 C9 1.388(5) . ? C8 H8 0.9300 . ? C9 C10 1.375(5) . ? C9 C14 1.505(5) . ? C10 C11 1.391(5) . ? C10 H10 0.9300 . ? C11 C12 1.377(5) . ? C11 C13 1.480(5) . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O3 174.50(13) . 2 ? O3 Cu1 N2 92.75(7) . . ? O3 Cu1 N2 92.75(7) 2 . ? O3 Cu1 N1 87.25(7) . . ? O3 Cu1 N1 87.25(7) 2 . ? N2 Cu1 N1 180.000(1) . . ? C13 O2 H2A 104(3) . . ? C14 O3 Cu1 107.9(2) . . ? C7 O5 H5 114(4) . . ? C6 N1 C6 117.9(4) . 2 ? C6 N1 Cu1 121.1(2) . . ? C6 N1 Cu1 121.1(2) 2 . ? C1 N2 C1 116.8(4) 2 . ? C1 N2 Cu1 121.6(2) 2 . ? C1 N2 Cu1 121.6(2) . . ? N2 C1 C2 123.2(4) . . ? N2 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C1 C2 C3 119.8(4) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C2 117.0(5) . 2 ? C2 C3 C4 121.5(2) . 1_565 ? C2 C3 C4 121.5(2) 2 1_565 ? C5 C4 C5 117.8(4) 2 . ? C5 C4 C3 121.1(2) 2 1_545 ? C5 C4 C3 121.1(2) . 1_545 ? C6 C5 C4 119.2(4) . . ? C6 C5 H5A 120.4 . . ? C4 C5 H5A 120.4 . . ? N1 C6 C5 122.9(4) . . ? N1 C6 H6 118.5 . . ? C5 C6 H6 118.5 . . ? O5 C7 C8 123.7(4) . . ? O5 C7 C12 116.7(4) . . ? C8 C7 C12 119.6(4) . . ? C7 C8 C9 120.4(4) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.8(4) . . ? C10 C9 C14 120.6(3) . . ? C8 C9 C14 119.6(3) . . ? C9 C10 C11 119.7(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.5(4) . . ? C12 C11 C13 120.9(3) . . ? C10 C11 C13 118.6(3) . . ? C11 C12 C7 119.9(4) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? O1 C13 O2 122.9(4) . . ? O1 C13 C11 122.4(3) . . ? O2 C13 C11 114.8(3) . . ? O4 C14 O3 122.3(3) . . ? O4 C14 C9 120.6(3) . . ? O3 C14 C9 117.1(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 O3 Cu1 O3 C14 82.82(19) 2 . . . ? N2 Cu1 O3 C14 -97.18(19) . . . . ? N1 Cu1 O3 C14 82.82(19) . . . . ? O3 Cu1 N1 C6 -100.8(2) . . . . ? O3 Cu1 N1 C6 79.2(2) 2 . . . ? N2 Cu1 N1 C6 -157(100) . . . . ? O3 Cu1 N1 C6 79.2(2) . . . 2 ? O3 Cu1 N1 C6 -100.8(2) 2 . . 2 ? N2 Cu1 N1 C6 23(100) . . . 2 ? O3 Cu1 N2 C1 -130.6(2) . . . 2 ? O3 Cu1 N2 C1 49.4(2) 2 . . 2 ? N1 Cu1 N2 C1 -74(100) . . . 2 ? O3 Cu1 N2 C1 49.4(2) . . . . ? O3 Cu1 N2 C1 -130.6(2) 2 . . . ? N1 Cu1 N2 C1 106(100) . . . . ? C1 N2 C1 C2 0.1(3) 2 . . . ? Cu1 N2 C1 C2 -179.9(3) . . . . ? N2 C1 C2 C3 -0.3(7) . . . . ? C1 C2 C3 C2 0.1(3) . . . 2 ? C1 C2 C3 C4 -179.9(3) . . . 1_565 ? C5 C4 C5 C6 -0.7(3) 2 . . . ? C3 C4 C5 C6 179.3(3) 1_545 . . . ? C6 N1 C6 C5 -0.7(3) 2 . . . ? Cu1 N1 C6 C5 179.3(3) . . . . ? C4 C5 C6 N1 1.4(5) . . . . ? O5 C7 C8 C9 179.7(4) . . . . ? C12 C7 C8 C9 -0.1(6) . . . . ? C7 C8 C9 C10 1.0(6) . . . . ? C7 C8 C9 C14 -177.4(4) . . . . ? C8 C9 C10 C11 -0.9(5) . . . . ? C14 C9 C10 C11 177.6(3) . . . . ? C9 C10 C11 C12 -0.1(6) . . . . ? C9 C10 C11 C13 178.1(3) . . . . ? C10 C11 C12 C7 1.0(6) . . . . ? C13 C11 C12 C7 -177.1(4) . . . . ? O5 C7 C12 C11 179.3(4) . . . . ? C8 C7 C12 C11 -0.9(6) . . . . ? C12 C11 C13 O1 178.1(4) . . . . ? C10 C11 C13 O1 -0.1(6) . . . . ? C12 C11 C13 O2 -1.0(5) . . . . ? C10 C11 C13 O2 -179.2(3) . . . . ? Cu1 O3 C14 O4 11.3(4) . . . . ? Cu1 O3 C14 C9 -165.7(2) . . . . ? C10 C9 C14 O4 -157.9(3) . . . . ? C8 C9 C14 O4 20.6(5) . . . . ? C10 C9 C14 O3 19.2(5) . . . . ? C8 C9 C14 O3 -162.3(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O1 0.82(5) 1.86(5) 2.667(4) 168(5) 5_655 O5 H5 O4 0.79(6) 1.93(6) 2.688(4) 161(6) 7_455 _diffrn_measured_fraction_theta_max 0.957 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.877 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.095 _database_code_depnum_ccdc_archive 'CCDC 657329'