Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Catalina Ruiz-Perez' 'Maria Hernandez-Molina' 'M. Julve' 'F. Lloret' 'Yolanda Rodriguez-Martin' 'Joaquin Sanchiz' _publ_contact_author_name 'Prof Catalina Ruiz-Perez' _publ_contact_author_address ; Laboratorio de Rayos X y Materiales Moleculares Dpto de Fisica Fundamental II Universidad de La Laguna Facultad de Fisica Avda. Astrofisico La Laguna Tenerife E-38206 SPAIN ; _publ_contact_author_email CARUIZ@ULL.ES _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Crystal structures and magnetic properties of two- and three-dimensional malonato-bridged manganese(II) complexes ; data_COMPOUND_1 _database_code_CSD 185412 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 Mn N2 O5' _chemical_formula_weight 331.19 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P21cn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y, -z' 'x, -y+1/2, z+1/2' 'x+1/2, y+1/2, -z+1/2' _cell_length_a 7.2540(10) _cell_length_b 7.7270(10) _cell_length_c 24.4130(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1368.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 18 _exptl_crystal_description prism _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.988 _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 graphite _diffrn_measurement_device_type 'MACH-3 four-circle diffractometer' _diffrn_measurement_method w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <10% _diffrn_reflns_number 2177 _diffrn_reflns_av_R_equivalents 0.0049 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 2 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 29.96 _reflns_number_total 2133 _reflns_number_gt 1414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD-4 Express' _computing_cell_refinement 'Enraf-Nonius CAD-4 Express' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CrystalMaker _computing_publication_material 'PARST95 (Nardelli, 1995)' _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 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 -0.13(11) _refine_ls_number_reflns 2133 _refine_ls_number_parameters 121 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1630 _refine_ls_R_factor_gt 0.0956 _refine_ls_wR_factor_ref 0.3615 _refine_ls_wR_factor_gt 0.2844 _refine_ls_goodness_of_fit_ref 1.450 _refine_ls_restrained_S_all 1.450 _refine_ls_shift/su_max 1.996 #(at C11) _refine_ls_shift/su_mean 0.153 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 Mn1 Mn 0.7960(5) 0.05592(14) 0.71876(4) 0.0346(5) Uani 1 1 d . . . O1 O 0.9856(16) 0.2190(15) 0.7625(5) 0.043(3) Uani 1 1 d . . . O2 O 1.0718(15) 0.4197(15) 0.8218(5) 0.043(3) Uani 1 1 d . . . O3 O 0.5848(16) 0.2108(14) 0.7624(5) 0.040(3) Uani 1 1 d . . . O4 O 0.5145(17) 0.4181(13) 0.8223(5) 0.046(3) Uani 1 1 d . . . O1W O 0.803(3) -0.1447(9) 0.7853(2) 0.044(2) Uani 1 1 d . . . N1 N 0.789(5) 0.2540(13) 0.6509(4) 0.094(2) Uani 1 1 d . . . N2 N 0.730(4) 0.5511(13) 0.4676(4) 0.094(2) Uani 1 1 d . . . C1 C 0.972(2) 0.2980(15) 0.8059(6) 0.037(4) Uani 1 1 d . . . C2 C 0.789(3) 0.2643(11) 0.8385(3) 0.041(3) Uani 1 1 d . . . H1 H 0.7827 0.1435 0.8491 0.050 Uiso 1 1 calc R . . H2 H 0.7883 0.3338 0.8716 0.050 Uiso 1 1 calc R . . C3 C 0.627(2) 0.3075(17) 0.8055(6) 0.035(3) Uani 1 1 d . . . C11 C 0.797(7) 0.4213(15) 0.6580(5) 0.094(2) Uani 1 1 d . . . H11 H 0.8116 0.4608 0.6937 0.113 Uiso 1 1 calc R . . C12 C 0.785(7) 0.5438(15) 0.6176(4) 0.094(2) Uani 1 1 d . . . H12 H 0.7600 0.6590 0.6258 0.113 Uiso 1 1 calc R . . C13 C 0.811(5) 0.4901(16) 0.5643(4) 0.094(2) Uani 1 1 d . . . C14 C 0.708(4) 0.3178(17) 0.5577(5) 0.094(2) Uani 1 1 d . . . H14 H 0.6414 0.2926 0.5261 0.113 Uiso 1 1 calc R . . C15 C 0.718(4) 0.2043(17) 0.5996(5) 0.094(2) Uani 1 1 d . . . H15 H 0.6785 0.0911 0.5944 0.113 Uiso 1 1 calc R . . C16 C 0.725(4) 0.6145(16) 0.5181(5) 0.094(2) Uani 1 1 d . . . C17 C 0.666(5) 0.7852(18) 0.5272(5) 0.094(2) Uani 1 1 d . . . H17 H 0.6429 0.8258 0.5624 0.113 Uiso 1 1 calc R . . C18 C 0.643(3) 0.8888(12) 0.4830(4) 0.094(2) Uani 1 1 d . . . H18 H 0.5862 0.9961 0.4864 0.113 Uiso 1 1 calc R . . C19 C 0.707(3) 0.8314(12) 0.4320(4) 0.094(2) Uani 1 1 d R . . H19 H 0.7417 0.9083 0.4046 0.113 Uiso 1 1 d R . . C20 C 0.704(4) 0.6605(16) 0.4245(5) 0.094(2) Uani 1 1 d . . . H20 H 0.6837 0.6157 0.3897 0.113 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 Mn1 0.0552(9) 0.0181(6) 0.0306(6) -0.0004(4) 0.0024(13) -0.0025(14) O1 0.054(7) 0.034(6) 0.042(6) -0.008(5) 0.012(5) 0.002(5) O2 0.049(7) 0.044(6) 0.038(6) -0.007(5) 0.010(5) -0.004(5) O3 0.053(7) 0.029(4) 0.037(5) -0.010(4) 0.000(5) 0.007(4) O4 0.080(10) 0.023(4) 0.035(6) -0.001(4) 0.010(6) 0.015(5) O1W 0.067(6) 0.031(3) 0.033(3) 0.003(2) 0.005(6) -0.020(6) N1 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) N2 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C1 0.064(10) 0.011(5) 0.035(7) 0.000(4) -0.007(7) 0.007(6) C2 0.066(7) 0.030(4) 0.027(3) 0.006(3) 0.005(8) -0.025(8) C3 0.049(9) 0.025(6) 0.030(7) 0.001(5) -0.003(6) 0.008(6) C11 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C12 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C13 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C14 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C15 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C16 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C17 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C18 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C19 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(3) C20 0.205(7) 0.0359(17) 0.0410(16) 0.0034(14) -0.013(3) -0.006(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 Mn1 O1 2.149(13) . ? Mn1 O4 2.157(12) 4_546 ? Mn1 O2 2.176(11) 4_446 ? Mn1 O3 2.217(11) . ? Mn1 O1W 2.247(6) . ? Mn1 N1 2.257(9) . ? O1 C1 1.227(19) . ? O2 C1 1.248(19) . ? O2 Mn1 2.176(11) 4_556 ? O3 C3 1.326(18) . ? O4 C3 1.254(17) . ? O4 Mn1 2.157(12) 4_456 ? N1 C11 1.305(15) . ? N1 C15 1.41(2) . ? N2 C16 1.327(15) . ? N2 C20 1.363(15) . ? C1 C2 1.57(2) . ? C2 C3 1.46(2) . ? C2 H1 0.9700 . ? C2 H2 0.9700 . ? C11 C12 1.369(15) . ? C11 H11 0.9300 . ? C12 C13 1.379(18) . ? C12 H12 0.9300 . ? C13 C14 1.53(3) . ? C13 C16 1.61(2) . ? C14 C15 1.349(16) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.40(2) . ? C17 C18 1.354(16) . ? C17 H17 0.9300 . ? C18 C19 1.3996 . ? C18 H18 0.9300 . ? C19 C20 1.333(15) . ? C19 H19 0.9300 . ? C20 H20 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 O1 Mn1 O4 92.9(4) . 4_546 ? O1 Mn1 O2 171.1(4) . 4_446 ? O4 Mn1 O2 95.7(3) 4_546 4_446 ? O1 Mn1 O3 83.5(3) . . ? O4 Mn1 O3 176.2(5) 4_546 . ? O2 Mn1 O3 87.9(5) 4_446 . ? O1 Mn1 O1W 91.7(5) . . ? O4 Mn1 O1W 88.8(5) 4_546 . ? O2 Mn1 O1W 90.7(5) 4_446 . ? O3 Mn1 O1W 92.4(5) . . ? O1 Mn1 N1 89.0(8) . . ? O4 Mn1 N1 90.6(8) 4_546 . ? O2 Mn1 N1 88.7(8) 4_446 . ? O3 Mn1 N1 88.3(8) . . ? O1W Mn1 N1 179.1(3) . . ? C1 O1 Mn1 132.0(12) . . ? C1 O2 Mn1 131.1(10) . 4_556 ? C3 O3 Mn1 121.6(11) . . ? C3 O4 Mn1 131.6(10) . 4_456 ? C11 N1 C15 113.9(16) . . ? C11 N1 Mn1 124.9(8) . . ? C15 N1 Mn1 118.5(11) . . ? C16 N2 C20 119.0(11) . . ? O1 C1 O2 126.6(16) . . ? O1 C1 C2 115.0(13) . . ? O2 C1 C2 117.3(11) . . ? C3 C2 C1 111.2(7) . . ? C3 C2 H1 109.4 . . ? C1 C2 H1 109.4 . . ? C3 C2 H2 109.5 . . ? C1 C2 H2 109.3 . . ? H1 C2 H2 108.0 . . ? O4 C3 O3 119.5(15) . . ? O4 C3 C2 119.9(13) . . ? O3 C3 C2 119.7(12) . . ? N1 C11 C12 125.8(12) . . ? N1 C11 H11 116.2 . . ? C12 C11 H11 116.0 . . ? C13 C12 C11 117.6(15) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.8 . . ? C12 C13 C14 107(2) . . ? C12 C13 C16 115(2) . . ? C14 C13 C16 104.9(19) . . ? C15 C14 C13 117.2(16) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.4 . . ? C14 C15 N1 121.2(14) . . ? C14 C15 H15 119.6 . . ? N1 C15 H15 119.2 . . ? N2 C16 C17 120.2(13) . . ? N2 C16 C13 114.8(14) . . ? C17 C16 C13 124.6(12) . . ? C18 C17 C16 117.7(13) . . ? C18 C17 H17 121.1 . . ? C16 C17 H17 121.2 . . ? C17 C18 C19 118.8(10) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 115.5(9) . . ? C20 C19 H19 122.6 . . ? C18 C19 H19 121.8 . . ? C19 C20 N2 120.4(11) . . ? C19 C20 H20 119.8 . . ? N2 C20 H20 119.8 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.186 #(0.06 A from C11) _refine_diff_density_min -1.163 #(0.03 A from C18) _refine_diff_density_rms 0.203 data_COMPOUND_2 _database_code_CSD 185413 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Mn2 N2 O10' _chemical_formula_weight 506.18 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' Mn Mn 0.3368 0.7283 '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 7.291(2) _cell_length_b 18.454(3) _cell_length_c 7.532(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.68(3) _cell_angle_gamma 90.00 _cell_volume 1013.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 18 _exptl_crystal_description sheet _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 1.303 _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 graphite _diffrn_measurement_device_type 'MACH-3 four-circle diffractometer' _diffrn_measurement_method w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% <10% _diffrn_reflns_number 3144 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0740 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 29.96 _reflns_number_total 2942 _reflns_number_gt 1897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf-Nonius CAD-4 Express' _computing_cell_refinement 'Enraf-Nonius CAD-4 Express' _computing_data_reduction 'HELENA (Spek, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CrystalMaker _computing_publication_material 'PARST95 (Nardelli, 1995)' _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^)+(0.0794P)^2^+1.7242P] 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 2942 _refine_ls_number_parameters 113 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1145 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1692 _refine_ls_wR_factor_gt 0.1462 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 Mn1 Mn 0.09591(8) 0.20604(3) 0.11173(7) 0.02383(18) Uani 1 1 d . . . O1 O -0.0678(4) 0.26897(17) -0.0770(4) 0.0343(7) Uani 1 1 d . . . O2 O 0.2194(4) 0.15071(16) 0.3386(4) 0.0324(7) Uani 1 1 d . . . O3 O -0.0619(4) 0.26511(16) 0.3043(4) 0.0321(6) Uani 1 1 d . . . O4 O 0.2317(4) 0.15501(16) -0.1078(4) 0.0343(7) Uani 1 1 d . . . C1 C -0.1624(5) 0.3255(2) -0.0524(5) 0.0248(8) Uani 1 1 d . . . C2 C -0.1284(6) 0.3679(2) 0.1191(5) 0.0299(9) Uani 1 1 d . . . C3 C -0.1555(5) 0.3222(2) 0.2842(5) 0.0247(7) Uani 1 1 d . . . C11 C -0.4127(8) 0.0706(4) 0.1558(9) 0.0698(11) Uani 1 1 d . . . H11 H -0.5085 0.0719 0.2347 0.084 Uiso 1 1 calc R . . C12 C -0.2625(8) 0.1159(4) 0.1818(9) 0.0698(11) Uani 1 1 d . . . H12 H -0.2612 0.1466 0.2799 0.084 Uiso 1 1 calc R . . C13 C -0.1301(8) 0.0734(4) -0.0578(9) 0.0698(11) Uani 1 1 d . . . H13 H -0.0328 0.0732 -0.1349 0.084 Uiso 1 1 calc R . . C14 C -0.2730(2) 0.02632(10) -0.0931(3) 0.0698(11) Uani 1 1 d . . . H14 H -0.2698 -0.0043 -0.1910 0.084 Uiso 1 1 calc R . . C15 C -0.4201(2) 0.02462(10) 0.0162(3) 0.0316(9) Uani 1 1 d R . . N1 N -0.1215(2) 0.11834(10) 0.0764(3) 0.0342(8) Uani 1 1 d R . . O1W O 0.3142(2) 0.29113(10) 0.1124(3) 0.0329(6) Uani 1 1 d RD . . H2 H -0.2156 0.4129 0.1077 0.038(13) Uiso 1 1 d R . . H11W H 0.3819 0.2764 0.0059 0.047(15) Uiso 1 1 d RD . . H12W H 0.3895 0.2780 0.2186 0.07(2) Uiso 1 1 d RD . . H1 H -0.0166 0.3795 0.1226 0.063(19) Uiso 1 1 d 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 Mn1 0.0222(3) 0.0291(3) 0.0202(3) -0.0008(2) 0.00038(19) -0.0017(2) O1 0.0420(18) 0.0396(16) 0.0208(13) -0.0042(12) -0.0065(12) 0.0106(14) O2 0.0339(15) 0.0337(16) 0.0291(15) -0.0011(12) -0.0061(12) -0.0029(13) O3 0.0386(16) 0.0359(15) 0.0223(13) 0.0038(12) 0.0066(12) 0.0101(13) O4 0.0365(16) 0.0358(16) 0.0313(15) -0.0048(13) 0.0108(12) -0.0081(13) C1 0.0251(18) 0.031(2) 0.0187(16) 0.0033(14) 0.0006(14) -0.0035(16) C2 0.041(2) 0.029(2) 0.0204(18) 0.0008(15) 0.0006(16) -0.0075(17) C3 0.0234(17) 0.0311(19) 0.0196(16) -0.0028(14) -0.0012(13) -0.0032(16) C11 0.0541(18) 0.081(2) 0.076(2) -0.0466(18) 0.0327(16) -0.0395(17) C12 0.0541(18) 0.081(2) 0.076(2) -0.0466(18) 0.0327(16) -0.0395(17) C13 0.0541(18) 0.081(2) 0.076(2) -0.0466(18) 0.0327(16) -0.0395(17) C14 0.0541(18) 0.081(2) 0.076(2) -0.0466(18) 0.0327(16) -0.0395(17) C15 0.0212(18) 0.027(2) 0.047(2) -0.0041(18) -0.0013(17) -0.0032(15) N1 0.0242(16) 0.0328(18) 0.046(2) -0.0059(16) 0.0018(15) -0.0073(15) O1W 0.0344(15) 0.0401(16) 0.0242(13) -0.0013(13) 0.0001(12) -0.0052(13) _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 Mn1 O2 2.164(3) . ? Mn1 O1 2.167(3) . ? Mn1 O4 2.168(3) . ? Mn1 O3 2.171(3) . ? Mn1 O1W 2.2354(18) . ? Mn1 N1 2.2755(18) . ? O1 C1 1.267(5) . ? O2 C1 1.252(5) 4_666 ? O3 C3 1.262(5) . ? O4 C3 1.247(5) 4_665 ? C1 O2 1.252(5) 4_565 ? C1 C2 1.525(5) . ? C2 C3 1.521(5) . ? C2 H2 1.0478 . ? C2 H1 0.8423 . ? C3 O4 1.247(5) 4_566 ? C11 C15 1.351(6) . ? C11 C12 1.387(7) . ? C11 H11 0.9300 . ? C12 N1 1.318(6) . ? C12 H12 0.9300 . ? C13 N1 1.308(6) . ? C13 C14 1.376(5) . ? C13 H13 0.9300 . ? C14 C15 1.3715 . ? C14 H14 0.9300 . ? C15 C15 1.492(3) 3_455 ? O1W H11W 0.9919 . ? O1W H12W 0.9877 . ? 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 Mn1 O1 168.35(12) . . ? O2 Mn1 O4 102.04(12) . . ? O1 Mn1 O4 89.29(12) . . ? O2 Mn1 O3 85.75(11) . . ? O1 Mn1 O3 82.90(11) . . ? O4 Mn1 O3 172.19(11) . . ? O2 Mn1 O1W 92.87(10) . . ? O1 Mn1 O1W 90.20(11) . . ? O4 Mn1 O1W 88.04(10) . . ? O3 Mn1 O1W 92.13(10) . . ? O2 Mn1 N1 91.67(9) . . ? O1 Mn1 N1 86.33(10) . . ? O4 Mn1 N1 86.21(9) . . ? O3 Mn1 N1 93.11(10) . . ? O1W Mn1 N1 173.31(10) . . ? C1 O1 Mn1 129.6(2) . . ? C1 O2 Mn1 127.9(3) 4_666 . ? C3 O3 Mn1 129.4(2) . . ? C3 O4 Mn1 132.5(3) 4_665 . ? O2 C1 O1 124.0(4) 4_565 . ? O2 C1 C2 117.9(4) 4_565 . ? O1 C1 C2 118.1(3) . . ? C3 C2 C1 112.7(3) . . ? C3 C2 H2 114.4 . . ? C1 C2 H2 104.7 . . ? C3 C2 H1 105.3 . . ? C1 C2 H1 106.9 . . ? H2 C2 H1 112.7 . . ? O4 C3 O3 124.6(4) 4_566 . ? O4 C3 C2 116.7(4) 4_566 . ? O3 C3 C2 118.6(3) . . ? C15 C11 C12 120.1(5) . . ? C15 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? N1 C12 C11 124.2(5) . . ? N1 C12 H12 117.9 . . ? C11 C12 H12 117.9 . . ? N1 C13 C14 124.6(4) . . ? N1 C13 H13 117.7 . . ? C14 C13 H13 117.7 . . ? C15 C14 C13 119.9(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C11 C15 C14 116.0(2) . . ? C11 C15 C15 121.5(3) . 3_455 ? C14 C15 C15 122.45(15) . 3_455 ? C13 N1 C12 115.1(4) . . ? C13 N1 Mn1 124.0(3) . . ? C12 N1 Mn1 120.4(3) . . ? Mn1 O1W H11W 100.2 . . ? Mn1 O1W H12W 102.1 . . ? H11W O1W H12W 108.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.991 _refine_diff_density_min -0.917 _refine_diff_density_rms 0.123