# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and The Centre National de la Recherche Scientifique, 2010 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Perutz, Robin' 'Gibson, Elizabeth' 'Duhme-Klair, Anne' _publ_contact_author_name 'Perutz, Robin' _publ_contact_author_email RNP1@YORK.AC.UK _publ_section_title ; Design and synthesis of water soluble (metallo)porphyrins with pendant arms: studies of binding to xanthine oxidase ; # Attachment '- rnp0618m.cif' data_rnp0618m _database_code_depnum_ccdc_archive 'CCDC 757513' #TrackingRef '- rnp0618m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 N2 O4' _chemical_formula_sum 'C15 H14 N2 O4' _chemical_formula_weight 286.28 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.6031(9) _cell_length_b 8.0726(5) _cell_length_c 13.6339(9) _cell_angle_alpha 90.00 _cell_angle_beta 118.0610(10) _cell_angle_gamma 90.00 _cell_volume 1321.17(15) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5822 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 28.30 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.906 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 13200 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3270 _reflns_number_gt 2937 _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, 1997)' _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^)+(0.0556P)^2^+0.4670P] 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 3270 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C1 C 0.66305(8) 0.56500(13) 0.92848(8) 0.0155(2) Uani 1 1 d . . . C2 C 0.75532(8) 0.46464(13) 0.93080(8) 0.0151(2) Uani 1 1 d . . . C3 C 0.85447(8) 0.41938(12) 1.02619(8) 0.0145(2) Uani 1 1 d . . . C4 C 0.93668(8) 0.32896(13) 1.01578(8) 0.0156(2) Uani 1 1 d . . . H4 H 1.0035 0.2996 1.0802 0.019 Uiso 1 1 calc R . . C5 C 0.92065(8) 0.28188(13) 0.91082(8) 0.0151(2) Uani 1 1 d . . . C6 C 0.82165(8) 0.32304(13) 0.81578(8) 0.0172(2) Uani 1 1 d . . . H6 H 0.8096 0.2886 0.7444 0.021 Uiso 1 1 calc R . . C7 C 0.74201(8) 0.41405(13) 0.82711(8) 0.0169(2) Uani 1 1 d . . . H7 H 0.6757 0.4436 0.7622 0.020 Uiso 1 1 calc R . . C8 C 1.10223(8) 0.14084(13) 0.97162(8) 0.0158(2) Uani 1 1 d . . . C9 C 1.17451(8) 0.06261(13) 0.92800(8) 0.0158(2) Uani 1 1 d . . . C10 C 1.25409(9) -0.05021(13) 0.99722(9) 0.0191(2) Uani 1 1 d . . . H10 H 1.2618 -0.0752 1.0686 0.023 Uiso 1 1 calc R . . C11 C 1.32205(10) -0.12562(14) 0.95996(10) 0.0237(2) Uani 1 1 d . . . H11 H 1.3750 -0.2044 1.0072 0.028 Uiso 1 1 calc R . . C12 C 1.24234(9) 0.01801(15) 0.79698(9) 0.0220(2) Uani 1 1 d . . . H12 H 1.2386 0.0439 0.7273 0.026 Uiso 1 1 calc R . . C13 C 1.16924(9) 0.09904(14) 0.82589(9) 0.0188(2) Uani 1 1 d . . . H13 H 1.1170 0.1773 0.7770 0.023 Uiso 1 1 calc R . . C14 C 0.57528(9) 0.68597(15) 1.02253(9) 0.0217(2) Uani 1 1 d . . . H14A H 0.5847 0.7997 1.0031 0.033 Uiso 1 1 calc R . . H14B H 0.5778 0.6852 1.0956 0.033 Uiso 1 1 calc R . . H14C H 0.5033 0.6427 0.9666 0.033 Uiso 1 1 calc R . . C15 C 0.96516(9) 0.41730(16) 1.22416(9) 0.0227(2) Uani 1 1 d . . . H15A H 0.9683 0.2961 1.2286 0.034 Uiso 1 1 calc R . . H15B H 0.9638 0.4623 1.2902 0.034 Uiso 1 1 calc R . . H15C H 1.0309 0.4592 1.2204 0.034 Uiso 1 1 calc R . . N1 N 1.00100(7) 0.19667(11) 0.89325(7) 0.01576(19) Uani 1 1 d . . . H1 H 0.9794(12) 0.1722(18) 0.8241(13) 0.025(4) Uiso 1 1 d . . . N2 N 1.31763(8) -0.09434(13) 0.86164(9) 0.0242(2) Uani 1 1 d . . . O1 O 0.66382(6) 0.58327(10) 1.02590(6) 0.01957(18) Uani 1 1 d . . . O2 O 0.58976(7) 0.62519(12) 0.84396(7) 0.0266(2) Uani 1 1 d . . . O3 O 0.86665(6) 0.46738(10) 1.12678(6) 0.01891(18) Uani 1 1 d . . . O4 O 1.13537(7) 0.14996(11) 1.07154(6) 0.0248(2) 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 C1 0.0144(4) 0.0174(5) 0.0155(5) 0.0004(4) 0.0077(4) -0.0013(4) C2 0.0138(4) 0.0171(5) 0.0147(5) 0.0014(4) 0.0071(4) 0.0002(4) C3 0.0150(5) 0.0165(5) 0.0121(4) -0.0002(3) 0.0065(4) -0.0014(4) C4 0.0131(4) 0.0193(5) 0.0131(4) 0.0008(4) 0.0052(4) 0.0003(4) C5 0.0135(4) 0.0171(5) 0.0155(5) 0.0000(4) 0.0073(4) -0.0004(4) C6 0.0165(5) 0.0222(5) 0.0123(4) -0.0012(4) 0.0063(4) 0.0006(4) C7 0.0139(5) 0.0215(5) 0.0133(5) 0.0015(4) 0.0048(4) 0.0008(4) C8 0.0153(5) 0.0166(5) 0.0158(5) -0.0006(4) 0.0077(4) 0.0000(4) C9 0.0137(4) 0.0171(5) 0.0170(5) -0.0030(4) 0.0076(4) -0.0025(4) C10 0.0187(5) 0.0192(5) 0.0218(5) 0.0017(4) 0.0116(4) 0.0002(4) C11 0.0225(5) 0.0200(5) 0.0330(6) 0.0037(4) 0.0168(5) 0.0043(4) C12 0.0197(5) 0.0296(6) 0.0197(5) -0.0050(4) 0.0118(4) -0.0034(4) C13 0.0149(5) 0.0246(5) 0.0163(5) -0.0016(4) 0.0068(4) -0.0011(4) C14 0.0195(5) 0.0250(5) 0.0218(5) -0.0016(4) 0.0108(4) 0.0066(4) C15 0.0182(5) 0.0362(6) 0.0118(5) 0.0005(4) 0.0055(4) 0.0052(4) N1 0.0140(4) 0.0219(4) 0.0114(4) -0.0021(3) 0.0060(3) 0.0008(3) N2 0.0231(5) 0.0250(5) 0.0303(5) -0.0043(4) 0.0173(4) -0.0005(4) O1 0.0191(4) 0.0251(4) 0.0155(4) 0.0010(3) 0.0090(3) 0.0078(3) O2 0.0206(4) 0.0423(5) 0.0178(4) 0.0086(3) 0.0095(3) 0.0130(4) O3 0.0160(4) 0.0282(4) 0.0117(3) -0.0008(3) 0.0059(3) 0.0043(3) O4 0.0218(4) 0.0366(5) 0.0138(4) -0.0002(3) 0.0064(3) 0.0100(3) _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 C1 O2 1.2153(13) . ? C1 O1 1.3315(12) . ? C1 C2 1.4817(14) . ? C2 C7 1.3991(14) . ? C2 C3 1.4120(13) . ? C3 O3 1.3583(12) . ? C3 C4 1.3974(14) . ? C4 C5 1.3951(14) . ? C4 H4 0.9500 . ? C5 C6 1.4004(14) . ? C5 N1 1.4042(13) . ? C6 C7 1.3765(14) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 O4 1.2194(13) . ? C8 N1 1.3627(13) . ? C8 C9 1.5064(14) . ? C9 C10 1.3896(15) . ? C9 C13 1.3913(14) . ? C10 C11 1.3875(15) . ? C10 H10 0.9500 . ? C11 N2 1.3373(16) . ? C11 H11 0.9500 . ? C12 N2 1.3413(16) . ? C12 C13 1.3931(15) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.4450(12) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O3 1.4311(12) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? N1 H1 0.868(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 121.30(9) . . ? O2 C1 C2 123.21(9) . . ? O1 C1 C2 115.48(9) . . ? C7 C2 C3 117.94(9) . . ? C7 C2 C1 115.62(9) . . ? C3 C2 C1 126.42(9) . . ? O3 C3 C4 121.89(9) . . ? O3 C3 C2 117.78(9) . . ? C4 C3 C2 120.33(9) . . ? C5 C4 C3 120.00(9) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.18(9) . . ? C4 C5 N1 123.36(9) . . ? C6 C5 N1 116.44(9) . . ? C7 C6 C5 119.20(9) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C6 C7 C2 122.32(9) . . ? C6 C7 H7 118.8 . . ? C2 C7 H7 118.8 . . ? O4 C8 N1 124.21(9) . . ? O4 C8 C9 119.97(9) . . ? N1 C8 C9 115.82(9) . . ? C10 C9 C13 118.36(9) . . ? C10 C9 C8 116.83(9) . . ? C13 C9 C8 124.78(9) . . ? C11 C10 C9 118.64(10) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? N2 C11 C10 124.10(11) . . ? N2 C11 H11 117.9 . . ? C10 C11 H11 118.0 . . ? N2 C12 C13 123.88(10) . . ? N2 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? C9 C13 C12 118.44(10) . . ? C9 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 N1 C5 127.50(9) . . ? C8 N1 H1 118.5(10) . . ? C5 N1 H1 113.8(10) . . ? C11 N2 C12 116.54(10) . . ? C1 O1 C14 114.62(8) . . ? C3 O3 C15 118.19(8) . . ? 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 O2 C1 C2 C7 -12.45(15) . . . . ? O1 C1 C2 C7 166.31(9) . . . . ? O2 C1 C2 C3 166.15(11) . . . . ? O1 C1 C2 C3 -15.09(15) . . . . ? C7 C2 C3 O3 -179.40(9) . . . . ? C1 C2 C3 O3 2.03(15) . . . . ? C7 C2 C3 C4 0.94(15) . . . . ? C1 C2 C3 C4 -177.63(10) . . . . ? O3 C3 C4 C5 179.86(9) . . . . ? C2 C3 C4 C5 -0.48(15) . . . . ? C3 C4 C5 C6 -0.87(16) . . . . ? C3 C4 C5 N1 177.43(9) . . . . ? C4 C5 C6 C7 1.73(16) . . . . ? N1 C5 C6 C7 -176.68(9) . . . . ? C5 C6 C7 C2 -1.28(16) . . . . ? C3 C2 C7 C6 -0.05(16) . . . . ? C1 C2 C7 C6 178.67(10) . . . . ? O4 C8 C9 C10 24.21(15) . . . . ? N1 C8 C9 C10 -155.31(10) . . . . ? O4 C8 C9 C13 -153.76(11) . . . . ? N1 C8 C9 C13 26.72(15) . . . . ? C13 C9 C10 C11 -2.17(15) . . . . ? C8 C9 C10 C11 179.72(10) . . . . ? C9 C10 C11 N2 1.39(18) . . . . ? C10 C9 C13 C12 1.36(15) . . . . ? C8 C9 C13 C12 179.31(10) . . . . ? N2 C12 C13 C9 0.36(17) . . . . ? O4 C8 N1 C5 4.27(17) . . . . ? C9 C8 N1 C5 -176.23(9) . . . . ? C4 C5 N1 C8 2.93(17) . . . . ? C6 C5 N1 C8 -178.71(10) . . . . ? C10 C11 N2 C12 0.30(17) . . . . ? C13 C12 N2 C11 -1.20(17) . . . . ? O2 C1 O1 C14 -3.14(15) . . . . ? C2 C1 O1 C14 178.07(9) . . . . ? C4 C3 O3 C15 -2.42(15) . . . . ? C2 C3 O3 C15 177.92(9) . . . . ? 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 N1 H1 O2 0.868(15) 2.062(15) 2.9257(12) 173.4(14) 2_646 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.377 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.048