# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2001 data_global _journal_coden_Cambridge 440 _publ_requested_journal 'New Journal of Chemistry' loop_ _publ_author_name 'Iwayan Dasna' 'Stéphane Golhen' 'Lahcène Ouahab' 'Nathalie Daro' 'Jean-Pascal Sutter' _publ_contact_author_name 'Dr Lahcene Ouahab' _publ_contact_author_address ; Laboratoire des Composes Solides et Inorganiques Moleculaires Universite de Rennes 1 UMR 6511 CNRS Campus de Beaulieu Rennes Cedex 35042 FRANCE ; _publ_contact_author_email 'OUAHAB@UNIV-RENNES1.FR' _publ_section_title ; Sythesis, X-Ray Crystal Structures and Magnetic Properties of CuII and MnII Complexes Containing Imino Nitroxide Radicals and Dicyanamide Anion ; data_1 _database_code_CSD 164372 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H64 Cu2 N24 O4' _chemical_formula_weight 1264.39 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 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 22.2730(11) _cell_length_b 23.3463(12) _cell_length_c 7.1583(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.960(3) _cell_angle_gamma 90.00 _cell_volume 3713.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13156 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.103 _exptl_crystal_description parallelepipede _exptl_crystal_colour orange _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1316 _exptl_absorpt_coefficient_mu 0.627 _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 ? _diffrn_measurement_device 'KappaCCD' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7350 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.12 _reflns_number_total 4096 _reflns_number_gt 3149 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1308P)^2^+3.2370P] 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 4096 _refine_ls_number_parameters 206 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.2081 _refine_ls_wR_factor_gt 0.1931 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.12153(2) 0.2500 0.0421(2) Uani 1 2 d S . . N1 N 0.44755(13) 0.18320(11) 0.1238(3) 0.0428(6) Uani 1 1 d . . . C2 C 0.39866(17) 0.22209(15) -0.1535(5) 0.0538(9) Uani 1 1 d . . . H2 H 0.3910 0.2198 -0.2827 0.065 Uiso 1 1 calc R . . C1 C 0.43475(17) 0.18237(14) -0.0607(4) 0.0497(8) Uani 1 1 d . . . H1 H 0.4512 0.1533 -0.1300 0.060 Uiso 1 1 calc R . . C5 C 0.42303(18) 0.22519(14) 0.2221(5) 0.0515(8) Uani 1 1 d . . . H5 H 0.4312 0.2262 0.3512 0.062 Uiso 1 1 calc R . . C4 C 0.38639(18) 0.26663(15) 0.1393(5) 0.0557(9) Uani 1 1 d . . . H4 H 0.3703 0.2951 0.2118 0.067 Uiso 1 1 calc R . . N2 N 0.32855(16) 0.32219(14) -0.3250(4) 0.0610(8) Uani 1 1 d . . . C3 C 0.37351(17) 0.26589(14) -0.0526(5) 0.0497(8) Uani 1 1 d . . . N3 N 0.2976(2) 0.34109(16) -0.0426(5) 0.0795(12) Uani 1 1 d . . . O1A O 0.3580(2) 0.30203(19) -0.4490(5) 0.0901(18) Uani 0.812(9) 1 d P . . O1B O 0.2647(11) 0.3236(11) 0.096(3) 0.116(10) Uani 0.190(10) 1 d P . . C7 C 0.2665(2) 0.38352(18) -0.1700(7) 0.0752(13) Uani 1 1 d . . . C6 C 0.33275(18) 0.30997(16) -0.1392(5) 0.0558(9) Uani 1 1 d . . . C8 C 0.2769(2) 0.3623(2) -0.3667(7) 0.0740(12) Uani 1 1 d . . . C12 C 0.2918(4) 0.4051(3) -0.5117(9) 0.152(4) Uani 1 1 d . . . H12A H 0.2969 0.3859 -0.6281 0.229 Uiso 1 1 calc R . . H12B H 0.3285 0.4245 -0.4716 0.229 Uiso 1 1 calc R . . H12C H 0.2598 0.4325 -0.5286 0.229 Uiso 1 1 calc R . . N4 N 0.44986(14) 0.06132(12) 0.1208(4) 0.0538(7) Uani 1 1 d . . . C13 C 0.42475(15) 0.01880(14) 0.0972(5) 0.0465(7) Uani 1 1 d . . . C9 C 0.3021(5) 0.4401(2) -0.1211(11) 0.149(4) Uani 1 1 d . . . H9A H 0.3431 0.4358 -0.1524 0.224 Uiso 1 1 calc R . . H9B H 0.3012 0.4479 0.0103 0.224 Uiso 1 1 calc R . . H9C H 0.2839 0.4713 -0.1914 0.224 Uiso 1 1 calc R . . C11 C 0.2261(3) 0.3248(3) -0.4499(12) 0.142(3) Uani 1 1 d . . . H11A H 0.2155 0.2971 -0.3586 0.213 Uiso 1 1 calc R . . H11B H 0.2390 0.3053 -0.5583 0.213 Uiso 1 1 calc R . . H11C H 0.1917 0.3482 -0.4852 0.213 Uiso 1 1 calc R . . C10 C 0.2017(4) 0.3894(4) -0.1218(12) 0.139(3) Uani 1 1 d . . . H10A H 0.2005 0.4027 0.0048 0.209 Uiso 1 1 calc R . . H10B H 0.1821 0.3528 -0.1343 0.209 Uiso 1 1 calc R . . H10C H 0.1814 0.4163 -0.2054 0.209 Uiso 1 1 calc R . . C14 C 0.41534(15) -0.07604(14) 0.0461(4) 0.0457(7) Uani 1 1 d . . . N5 N 0.39111(14) -0.02601(14) 0.0680(6) 0.0682(10) Uani 1 1 d . . . N6 N 0.43224(17) -0.12208(12) 0.0223(4) 0.0560(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 0.0574(4) 0.0267(3) 0.0407(3) 0.000 -0.0062(2) 0.000 N1 0.0583(16) 0.0330(13) 0.0362(13) -0.0017(10) -0.0035(11) 0.0053(11) C2 0.072(2) 0.053(2) 0.0355(16) -0.0029(13) -0.0033(14) 0.0186(17) C1 0.067(2) 0.0426(17) 0.0390(16) -0.0073(13) -0.0032(14) 0.0116(15) C5 0.074(2) 0.0429(18) 0.0366(16) -0.0021(13) 0.0003(14) 0.0125(16) C4 0.085(3) 0.0431(18) 0.0395(17) -0.0022(13) 0.0057(16) 0.0198(17) N2 0.078(2) 0.0541(18) 0.0501(18) 0.0102(13) 0.0015(15) 0.0177(16) C3 0.062(2) 0.0428(17) 0.0437(17) 0.0021(13) 0.0015(14) 0.0129(15) N3 0.111(3) 0.065(2) 0.063(2) 0.0066(17) 0.014(2) 0.044(2) O1A 0.126(4) 0.096(3) 0.050(2) 0.0141(19) 0.017(2) 0.053(3) O1B 0.125(18) 0.15(2) 0.068(13) -0.011(12) 0.002(11) 0.058(16) C7 0.095(3) 0.054(2) 0.077(3) 0.0023(19) 0.000(2) 0.031(2) C6 0.069(2) 0.0469(19) 0.0514(19) 0.0069(15) 0.0021(16) 0.0152(17) C8 0.096(3) 0.053(2) 0.071(3) 0.009(2) -0.012(2) 0.022(2) C12 0.271(11) 0.093(5) 0.095(5) 0.051(4) 0.024(6) 0.060(6) N4 0.0649(18) 0.0361(15) 0.0592(18) -0.0086(12) -0.0038(14) -0.0007(13) C13 0.0496(18) 0.0404(18) 0.0491(18) -0.0070(13) -0.0004(14) 0.0047(14) C9 0.259(11) 0.053(3) 0.128(6) -0.019(3) -0.037(6) 0.015(5) C11 0.109(5) 0.122(6) 0.185(8) -0.063(5) -0.064(5) 0.046(4) C10 0.116(6) 0.171(8) 0.132(6) 0.002(5) 0.019(5) 0.067(5) C14 0.0509(18) 0.0452(19) 0.0407(16) -0.0040(13) 0.0004(13) -0.0109(14) N5 0.0507(18) 0.0463(18) 0.107(3) -0.0186(17) 0.0037(17) -0.0035(14) N6 0.079(2) 0.0384(16) 0.0500(17) -0.0029(11) -0.0004(15) -0.0055(14) _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 N4 1.984(3) . ? Cu1 N4 1.984(3) 2_655 ? Cu1 N1 2.027(3) 2_655 ? Cu1 N1 2.027(3) . ? N1 C1 1.332(4) . ? N1 C5 1.344(4) . ? C2 C1 1.369(5) . ? C2 C3 1.392(5) . ? C5 C4 1.374(5) . ? C4 C3 1.383(5) . ? N2 O1A 1.234(5) . ? N2 C6 1.357(5) . ? N2 C8 1.498(5) . ? C3 C6 1.480(5) . ? N3 C6 1.302(5) . ? N3 O1B 1.34(2) . ? N3 C7 1.485(5) . ? C7 C10 1.515(9) . ? C7 C8 1.525(7) . ? C7 C9 1.568(8) . ? C8 C12 1.496(8) . ? C8 C11 1.520(8) . ? N4 C13 1.146(4) . ? C13 N5 1.295(5) . ? C14 N6 1.155(4) . ? C14 N5 1.301(5) . ? 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 N4 Cu1 N4 89.77(18) . 2_655 ? N4 Cu1 N1 178.55(11) . 2_655 ? N4 Cu1 N1 90.40(12) 2_655 2_655 ? N4 Cu1 N1 90.40(12) . . ? N4 Cu1 N1 178.55(11) 2_655 . ? N1 Cu1 N1 89.46(15) 2_655 . ? C1 N1 C5 117.6(3) . . ? C1 N1 Cu1 120.6(2) . . ? C5 N1 Cu1 121.8(2) . . ? C1 C2 C3 119.3(3) . . ? N1 C1 C2 123.3(3) . . ? N1 C5 C4 122.6(3) . . ? C5 C4 C3 119.7(3) . . ? O1A N2 C6 128.4(3) . . ? O1A N2 C8 122.3(3) . . ? C6 N2 C8 109.1(3) . . ? C4 C3 C2 117.5(3) . . ? C4 C3 C6 119.1(3) . . ? C2 C3 C6 123.4(3) . . ? C6 N3 O1B 127.1(11) . . ? C6 N3 C7 108.5(3) . . ? O1B N3 C7 113.8(10) . . ? N3 C7 C10 109.3(5) . . ? N3 C7 C8 104.9(3) . . ? C10 C7 C8 116.5(5) . . ? N3 C7 C9 102.6(5) . . ? C10 C7 C9 110.4(6) . . ? C8 C7 C9 111.9(5) . . ? N3 C6 N2 113.6(3) . . ? N3 C6 C3 122.7(3) . . ? N2 C6 C3 123.8(3) . . ? C12 C8 N2 110.6(5) . . ? C12 C8 C11 108.0(6) . . ? N2 C8 C11 105.0(4) . . ? C12 C8 C7 118.6(5) . . ? N2 C8 C7 100.5(3) . . ? C11 C8 C7 113.1(5) . . ? C13 N4 Cu1 159.3(3) . . ? N4 C13 N5 173.8(4) . . ? N6 C14 N5 174.4(4) . . ? C13 N5 C14 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.882 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.114 #===END data_2 _database_code_CSD 164373 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H36 Mn N12 O4' _chemical_formula_weight 659.63 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1089(2) _cell_length_b 9.9495(3) _cell_length_c 13.2518(6) _cell_angle_alpha 69.3961(14) _cell_angle_beta 88.9996(14) _cell_angle_gamma 71.461(2) _cell_volume 827.09(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3591 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 345 _exptl_absorpt_coefficient_mu 0.451 _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_measurement_device_type 'KappaCCD' _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method 'CCD' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6724 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0557 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3787 _reflns_number_gt 2924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0753P)^2^+0.1378P] 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 3787 _refine_ls_number_parameters 216 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1201 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.030 _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 Mn Mn 0.0000 0.0000 0.0000 0.03234(16) Uani 1 2 d S . . OW1 O 0.0646(2) 0.17547(18) 0.04029(15) 0.0457(4) Uani 1 1 d . . . O1A O 0.5940(4) 0.1782(5) -0.4534(3) 0.0891(16) Uani 0.700(7) 1 d P . . O1B O -0.0492(10) 0.3988(10) -0.5854(6) 0.096(4) Uani 0.335(7) 1 d P . . N4 N 0.3095(3) -0.1530(2) 0.05661(18) 0.0454(5) Uani 1 1 d . . . N1 N 0.0938(3) 0.0811(2) -0.17075(15) 0.0393(4) Uani 1 1 d . . . C13 C 0.4558(3) -0.2344(3) 0.0435(2) 0.0394(5) Uani 1 1 d . . . C1 C 0.2634(3) 0.1129(3) -0.18832(19) 0.0448(5) Uani 1 1 d . . . H1 H 0.3473 0.0950 -0.1286 0.054 Uiso 1 1 calc R . . C3 C 0.1991(3) 0.1967(3) -0.38040(19) 0.0424(5) Uani 1 1 d . . . C2 C 0.3205(4) 0.1707(3) -0.2900(2) 0.0475(6) Uani 1 1 d . . . H2 H 0.4393 0.1921 -0.2979 0.057 Uiso 1 1 calc R . . C6 C 0.2520(4) 0.2542(3) -0.4914(2) 0.0481(6) Uani 1 1 d . . . C4 C 0.0232(3) 0.1625(3) -0.3627(2) 0.0497(6) Uani 1 1 d . . . H4 H -0.0624 0.1776 -0.4209 0.060 Uiso 1 1 calc R . . N2 N 0.4416(3) 0.2420(3) -0.51475(18) 0.0546(6) Uani 1 1 d . . . N5 N 0.6293(3) -0.3087(3) 0.0263(3) 0.0673(8) Uani 1 1 d . . . C14 C 0.6880(3) -0.4538(3) 0.0422(2) 0.0474(6) Uani 1 1 d . . . N3 N 0.1206(4) 0.3212(3) -0.57746(19) 0.0688(7) Uani 1 1 d . . . N6 N 0.7575(3) -0.5790(3) 0.0533(2) 0.0672(7) Uani 1 1 d . . . C5 C -0.0226(3) 0.1062(3) -0.2583(2) 0.0463(6) Uani 1 1 d . . . H5 H -0.1409 0.0844 -0.2479 0.056 Uiso 1 1 calc R . . C7 C 0.4402(4) 0.3248(3) -0.6327(2) 0.0553(6) Uani 1 1 d . . . C8 C 0.2281(4) 0.3434(3) -0.6755(2) 0.0575(7) Uani 1 1 d . . . C11 C 0.1141(7) 0.4986(4) -0.7603(3) 0.0994(13) Uani 1 1 d . . . H11A H 0.1159 0.5771 -0.7345 0.149 Uiso 1 1 calc R . . H11B H -0.0214 0.5050 -0.7735 0.149 Uiso 1 1 calc R . . H11C H 0.1759 0.5115 -0.8265 0.149 Uiso 1 1 calc R . . C10 C 0.6150(6) 0.2320(5) -0.6745(3) 0.0962(13) Uani 1 1 d . . . H10A H 0.5963 0.1383 -0.6690 0.144 Uiso 1 1 calc R . . H10B H 0.7365 0.2100 -0.6320 0.144 Uiso 1 1 calc R . . H10C H 0.6226 0.2889 -0.7490 0.144 Uiso 1 1 calc R . . C12 C 0.2224(6) 0.2201(5) -0.7153(3) 0.0841(10) Uani 1 1 d . . . H12A H 0.2932 0.1222 -0.6614 0.126 Uiso 1 1 calc R . . H12B H 0.2842 0.2317 -0.7814 0.126 Uiso 1 1 calc R . . H12C H 0.0863 0.2277 -0.7282 0.126 Uiso 1 1 calc R . . C9 C 0.4703(7) 0.4742(5) -0.6416(3) 0.0925(12) Uani 1 1 d . . . H9A H 0.3599 0.5329 -0.6152 0.139 Uiso 1 1 calc R . . H9B H 0.4779 0.5312 -0.7160 0.139 Uiso 1 1 calc R . . H9C H 0.5918 0.4522 -0.5991 0.139 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 Mn 0.0300(2) 0.0312(3) 0.0362(3) -0.01390(19) 0.00782(17) -0.00906(17) OW1 0.0402(8) 0.0407(9) 0.0658(11) -0.0285(8) 0.0148(7) -0.0165(7) O1A 0.0437(17) 0.136(3) 0.054(2) 0.0003(19) 0.0036(13) -0.0259(17) O1B 0.051(4) 0.128(7) 0.071(5) -0.004(4) -0.002(3) -0.016(4) N4 0.0348(10) 0.0411(11) 0.0583(13) -0.0206(10) 0.0055(8) -0.0075(8) N1 0.0391(10) 0.0445(11) 0.0378(10) -0.0159(8) 0.0083(7) -0.0180(8) C13 0.0343(11) 0.0366(11) 0.0504(14) -0.0170(10) 0.0056(9) -0.0146(9) C1 0.0450(12) 0.0593(15) 0.0359(12) -0.0168(11) 0.0059(9) -0.0256(11) C3 0.0402(11) 0.0503(14) 0.0345(12) -0.0133(10) 0.0070(9) -0.0149(10) C2 0.0455(13) 0.0618(16) 0.0407(13) -0.0153(11) 0.0093(10) -0.0290(11) C6 0.0493(13) 0.0511(14) 0.0355(13) -0.0114(11) 0.0087(10) -0.0111(10) C4 0.0393(12) 0.0700(17) 0.0395(13) -0.0179(12) 0.0021(9) -0.0199(11) N2 0.0445(11) 0.0646(14) 0.0435(12) -0.0081(10) 0.0119(9) -0.0168(10) N5 0.0378(11) 0.0480(13) 0.130(2) -0.0462(15) 0.0297(12) -0.0182(9) C14 0.0327(11) 0.0494(15) 0.0661(17) -0.0291(13) 0.0135(10) -0.0131(10) N3 0.0532(14) 0.100(2) 0.0376(13) -0.0199(13) 0.0022(10) -0.0106(13) N6 0.0534(13) 0.0522(14) 0.099(2) -0.0411(14) 0.0124(13) -0.0066(10) C5 0.0381(11) 0.0612(15) 0.0421(13) -0.0170(11) 0.0090(9) -0.0222(10) C7 0.0686(16) 0.0539(15) 0.0420(14) -0.0121(12) 0.0227(12) -0.0254(12) C8 0.0725(17) 0.0603(17) 0.0324(13) -0.0138(12) 0.0057(11) -0.0162(13) C11 0.129(3) 0.077(3) 0.057(2) -0.0055(18) -0.018(2) -0.008(2) C10 0.083(2) 0.122(3) 0.093(3) -0.052(3) 0.048(2) -0.034(2) C12 0.104(3) 0.099(3) 0.072(2) -0.047(2) 0.0199(19) -0.045(2) C9 0.137(4) 0.084(3) 0.069(2) -0.0173(19) 0.020(2) -0.067(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 Mn OW1 2.1722(15) 2 ? Mn OW1 2.1722(15) . ? Mn N4 2.2012(18) 2 ? Mn N4 2.2012(18) . ? Mn N1 2.2847(19) . ? Mn N1 2.2847(19) 2 ? O1A N2 1.211(4) . ? O1B N3 1.191(7) . ? N4 C13 1.151(3) . ? N1 C1 1.337(3) . ? N1 C5 1.338(3) . ? C13 N5 1.284(3) . ? C1 C2 1.376(3) . ? C3 C2 1.387(3) . ? C3 C4 1.393(3) . ? C3 C6 1.469(3) . ? C6 N3 1.313(3) . ? C6 N2 1.355(3) . ? C4 C5 1.374(3) . ? N2 C7 1.487(3) . ? N5 C14 1.307(3) . ? C14 N6 1.140(3) . ? N3 C8 1.481(4) . ? C7 C10 1.520(4) . ? C7 C9 1.532(5) . ? C7 C8 1.551(4) . ? C8 C12 1.508(5) . ? C8 C11 1.522(4) . ? 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 OW1 Mn OW1 180.00(8) 2 . ? OW1 Mn N4 90.54(7) 2 2 ? OW1 Mn N4 89.46(7) . 2 ? OW1 Mn N4 89.46(7) 2 . ? OW1 Mn N4 90.54(7) . . ? N4 Mn N4 180.0(2) 2 . ? OW1 Mn N1 87.04(7) 2 . ? OW1 Mn N1 92.96(7) . . ? N4 Mn N1 91.49(7) 2 . ? N4 Mn N1 88.51(7) . . ? OW1 Mn N1 92.96(7) 2 2 ? OW1 Mn N1 87.04(7) . 2 ? N4 Mn N1 88.51(7) 2 2 ? N4 Mn N1 91.49(7) . 2 ? N1 Mn N1 180.00(13) . 2 ? C13 N4 Mn 150.59(19) . . ? C1 N1 C5 116.78(19) . . ? C1 N1 Mn 121.44(15) . . ? C5 N1 Mn 121.70(14) . . ? N4 C13 N5 171.4(2) . . ? N1 C1 C2 123.6(2) . . ? C2 C3 C4 117.4(2) . . ? C2 C3 C6 122.7(2) . . ? C4 C3 C6 119.9(2) . . ? C1 C2 C3 119.3(2) . . ? N3 C6 N2 113.6(2) . . ? N3 C6 C3 123.3(2) . . ? N2 C6 C3 123.1(2) . . ? C5 C4 C3 119.3(2) . . ? O1A N2 C6 128.4(3) . . ? O1A N2 C7 122.3(2) . . ? C6 N2 C7 109.2(2) . . ? C13 N5 C14 123.8(2) . . ? N6 C14 N5 173.0(3) . . ? O1B N3 C6 128.2(5) . . ? O1B N3 C8 118.7(4) . . ? C6 N3 C8 108.7(2) . . ? N1 C5 C4 123.6(2) . . ? N2 C7 C10 109.0(3) . . ? N2 C7 C9 105.2(3) . . ? C10 C7 C9 109.4(3) . . ? N2 C7 C8 100.8(2) . . ? C10 C7 C8 116.8(3) . . ? C9 C7 C8 114.4(3) . . ? N3 C8 C12 105.4(3) . . ? N3 C8 C11 108.4(3) . . ? C12 C8 C11 109.5(3) . . ? N3 C8 C7 103.6(2) . . ? C12 C8 C7 113.8(3) . . ? C11 C8 C7 115.4(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.486 _refine_diff_density_min -0.434 _refine_diff_density_rms 0.057