# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Catalina Ruiz-Perez' _publ_contact_author_address ; Departamento de Fisica Fundamental II Universidad de La Laguna Avda Astrofisico Francisco Sanchez La Laguna Tenerife 38204 SPAIN ; _publ_contact_author_email CARUIZ@ULL.ES _publ_section_title ; Metamagnetism in hydrophobically induced carboxylate (phenylmalonate)-bridged copper(II) layers ; loop_ _publ_author_name 'Catalina Ruiz-Perez' 'Javier Campo' 'Miguel Julve' 'F. Lloret' 'Jorge Pasan' 'Joaquin Sanchiz' data_prueba _database_code_depnum_ccdc_archive 'CCDC 297276' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cu N2 O4' _chemical_formula_weight 321.77 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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.446 _cell_length_b 6.446 _cell_length_c 14.444 _cell_angle_alpha 90.00 _cell_angle_beta 98.14 _cell_angle_gamma 90.00 _cell_volume 594.1 _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Sheets _exptl_crystal_colour Blue _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 1.853 _exptl_absorpt_correction_type none _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_number 3279 _diffrn_reflns_av_R_equivalents 0.0857 _diffrn_reflns_av_sigmaI/netI 0.0788 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 31.94 _reflns_number_total 1980 _reflns_number_gt 1781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 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. ; _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^)+(0.2000P)^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 constr _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 0.57(17) _refine_ls_number_reflns 1980 _refine_ls_number_parameters 182 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1344 _refine_ls_R_factor_gt 0.1253 _refine_ls_wR_factor_ref 0.3233 _refine_ls_wR_factor_gt 0.3153 _refine_ls_goodness_of_fit_ref 1.411 _refine_ls_restrained_S_all 1.411 _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 C1 C 0.5920(14) 0.391(2) 0.5692(7) 0.0136(18) Uani 1 1 d . . . C2 C 0.7806(17) 0.280(2) 0.6127(8) 0.019(2) Uani 1 1 d . . . H2 H 0.7732 0.1398 0.5857 0.023 Uiso 1 1 calc R . . C3 C 0.9560(14) 0.396(2) 0.5706(6) 0.0128(17) Uani 1 1 d . . . C4 C 0.810(2) 0.253(2) 0.7174(9) 0.024(3) Uani 1 1 d . . . C5 C 0.817(2) 0.418(4) 0.7756(10) 0.039(4) Uani 1 1 d . . . H5 H 0.7969 0.5513 0.7517 0.047 Uiso 1 1 calc R . . C6 C 0.854(4) 0.387(3) 0.8668(12) 0.046(5) Uani 1 1 d . . . H6 H 0.8644 0.5003 0.9069 0.055 Uiso 1 1 calc R . . C7 C 0.876(3) 0.183(5) 0.9050(11) 0.061(7) Uani 1 1 d . . . H7 H 0.8984 0.1640 0.9695 0.073 Uiso 1 1 calc R . . C8 C 0.864(3) 0.006(4) 0.8431(16) 0.050(5) Uani 1 1 d . . . H8 H 0.8740 -0.1288 0.8661 0.060 Uiso 1 1 calc R . . C9 C 0.840(2) 0.044(4) 0.7524(11) 0.038(4) Uani 1 1 d . . . H9 H 0.8414 -0.0650 0.7105 0.045 Uiso 1 1 calc R . . C10 C 0.658(3) 0.218(3) 0.2069(9) 0.034(3) Uani 1 1 d . . . H10 H 0.6752 0.0802 0.2250 0.041 Uiso 1 1 calc R . . C12 C 0.610(3) 0.460(3) 0.0958(11) 0.039(3) Uani 1 1 d . . . H12 H 0.5864 0.4957 0.0328 0.047 Uiso 1 1 calc R . . C13 C 0.636(3) 0.619(3) 0.1618(13) 0.044(4) Uani 1 1 d . . . H13 H 0.6302 0.7582 0.1441 0.052 Uiso 1 1 calc R . . C14 C 0.6693(19) 0.564(3) 0.2499(11) 0.034(3) Uani 1 1 d . . . H14 H 0.6861 0.6654 0.2961 0.040 Uiso 1 1 calc R . . N1 N 0.6802(18) 0.353(2) 0.2761(8) 0.028(2) Uani 1 1 d . . . N2 N 0.616(4) 0.247(4) 0.1200(12) 0.068(7) Uani 1 1 d . . . O1 O 0.4893(10) 0.4914(17) 0.6227(5) 0.0156(15) Uani 1 1 d . . . O2 O 0.5450(10) 0.3781(16) 0.4810(5) 0.0160(14) Uani 1 1 d . . . O3 O 1.0780(12) 0.5018(19) 0.6236(5) 0.0211(17) Uani 1 1 d . . . O4 O 0.9484(11) 0.3811(16) 0.4833(5) 0.0184(15) Uani 1 1 d . . . Cu1 Cu 0.72661(15) 0.2034(3) 0.41826(7) 0.0171(4) 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 0.011(3) 0.010(5) 0.022(4) 0.002(4) 0.011(3) 0.000(4) C2 0.018(4) 0.014(5) 0.026(5) -0.003(4) 0.009(3) -0.008(4) C3 0.011(3) 0.012(5) 0.016(4) 0.006(4) 0.005(3) 0.003(4) C4 0.035(6) 0.019(8) 0.017(4) -0.001(4) 0.004(4) -0.006(5) C5 0.035(7) 0.061(13) 0.020(6) 0.011(7) 0.000(5) 0.017(8) C6 0.079(13) 0.028(9) 0.026(7) 0.000(7) -0.012(7) -0.012(9) C7 0.054(8) 0.091(19) 0.033(7) 0.044(12) -0.008(6) -0.025(12) C8 0.038(8) 0.038(11) 0.075(15) 0.006(10) 0.012(8) -0.003(8) C9 0.029(6) 0.054(12) 0.032(7) 0.002(7) 0.010(5) 0.009(7) C10 0.061(8) 0.011(7) 0.029(5) -0.009(6) 0.007(5) -0.012(7) C12 0.048(8) 0.040(9) 0.028(6) 0.002(6) 0.002(5) -0.003(7) C13 0.048(8) 0.027(8) 0.056(9) 0.007(8) 0.008(7) 0.010(7) C14 0.015(5) 0.031(7) 0.053(8) -0.011(7) -0.001(5) 0.008(5) N1 0.022(4) 0.026(6) 0.037(5) 0.000(5) 0.006(4) -0.004(5) N2 0.083(12) 0.069(19) 0.047(8) 0.002(9) -0.006(8) -0.022(12) O1 0.014(3) 0.016(4) 0.018(3) -0.001(3) 0.008(2) 0.009(3) O2 0.008(3) 0.015(4) 0.025(3) -0.005(3) 0.003(2) 0.004(3) O3 0.018(3) 0.028(5) 0.016(3) 0.002(3) -0.002(2) -0.007(3) O4 0.022(3) 0.012(4) 0.022(3) -0.004(3) 0.005(3) -0.012(3) Cu1 0.0128(5) 0.0163(7) 0.0226(6) -0.0023(7) 0.0040(4) -0.0012(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 C1 O1 1.264(12) . ? C1 O2 1.271(12) . ? C1 C2 1.474(17) . ? C2 C4 1.507(17) . ? C2 C3 1.552(15) . ? C3 O3 1.223(14) . ? C3 O4 1.259(12) . ? C4 C5 1.35(2) . ? C4 C9 1.44(3) . ? C5 C6 1.32(2) . ? C6 C7 1.42(3) . ? C7 C8 1.44(4) . ? C8 C9 1.32(3) . ? C10 N2 1.26(2) . ? C10 N1 1.31(2) . ? C12 C13 1.39(3) . ? C12 N2 1.42(3) . ? C13 C14 1.31(2) . ? C14 N1 1.41(2) . ? N1 Cu1 2.249(13) . ? O1 Cu1 1.980(9) 2_656 ? O2 Cu1 1.939(8) . ? O3 Cu1 1.964(10) 2_756 ? O4 Cu1 1.964(8) . ? Cu1 O3 1.964(10) 2_746 ? Cu1 O1 1.980(9) 2_646 ? 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 C1 O2 125.1(9) . . ? O1 C1 C2 117.5(9) . . ? O2 C1 C2 117.4(9) . . ? C1 C2 C4 117.5(10) . . ? C1 C2 C3 101.5(10) . . ? C4 C2 C3 116.8(10) . . ? O3 C3 O4 126.9(10) . . ? O3 C3 C2 117.7(9) . . ? O4 C3 C2 115.3(9) . . ? C5 C4 C9 121.6(13) . . ? C5 C4 C2 121.6(13) . . ? C9 C4 C2 116.7(12) . . ? C6 C5 C4 119.2(19) . . ? C5 C6 C7 121(2) . . ? C6 C7 C8 119.6(14) . . ? C9 C8 C7 117(2) . . ? C8 C9 C4 120.9(19) . . ? N2 C10 N1 130(2) . . ? C13 C12 N2 123.3(16) . . ? C14 C13 C12 116.8(18) . . ? C13 C14 N1 121.3(16) . . ? C10 N1 C14 115.8(13) . . ? C10 N1 Cu1 113.5(11) . . ? C14 N1 Cu1 130.7(11) . . ? C10 N2 C12 112.5(19) . . ? C1 O1 Cu1 125.3(7) . 2_656 ? C1 O2 Cu1 115.6(6) . . ? C3 O3 Cu1 124.0(7) . 2_756 ? C3 O4 Cu1 116.5(7) . . ? O2 Cu1 O3 169.8(4) . 2_746 ? O2 Cu1 O4 83.4(4) . . ? O3 Cu1 O4 94.5(3) 2_746 . ? O2 Cu1 O1 95.5(3) . 2_646 ? O3 Cu1 O1 84.6(5) 2_746 2_646 ? O4 Cu1 O1 168.1(4) . 2_646 ? O2 Cu1 N1 99.6(5) . . ? O3 Cu1 N1 90.6(4) 2_746 . ? O4 Cu1 N1 100.4(5) . . ? O1 Cu1 N1 91.5(4) 2_646 . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 31.94 _diffrn_measured_fraction_theta_full 0.888 _refine_diff_density_max 7.946 _refine_diff_density_min -1.710 _refine_diff_density_rms 0.371