# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Bu, Xian-He' _publ_contact_author_email buxh@nankai.edu.cn _publ_section_title ; Chiral Magnetic MnII Metal-Organic Frameworks with Achiral Tetrazolate-Based Ligand by Spontaneous Resolution ; _publ_author_name 'Xian-He Bu' # Attachment '- Complexes 1A-1B.cif' data_1A _database_code_depnum_ccdc_archive 'CCDC 782699' #TrackingRef '- Complexes 1A-1B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Mn N10 O2' _chemical_formula_weight 431.30 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 Tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.5842(15) _cell_length_b 10.5842(15) _cell_length_c 15.826(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1772.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17205 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.4 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.783 _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 18544 _diffrn_reflns_av_R_equivalents 0.0649 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.40 _reflns_number_total 2022 _reflns_number_gt 1882 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0269P)^2^+0.4406P] 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 0.02(2) _refine_ls_number_reflns 2022 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.220 _refine_ls_restrained_S_all 1.220 _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 N2 N 0.77409(19) 0.36575(19) 1.17148(12) 0.0219(5) Uani 1 1 d . . . Mn1 Mn 0.68706(3) 0.68706(3) 1.0000 0.01597(13) Uani 1 2 d S . . N1 N 0.7011(2) 0.34224(18) 1.02912(12) 0.0226(5) Uani 1 1 d . . . N3 N 0.8021(2) 0.46754(19) 1.22088(13) 0.0307(5) Uani 1 1 d . . . N5 N 0.74852(19) 0.54202(19) 1.09725(12) 0.0198(5) Uani 1 1 d . . . C8 C 0.7413(2) 0.4162(2) 1.09674(15) 0.0192(5) Uani 1 1 d . . . N4 N 0.7870(2) 0.5706(2) 1.17740(12) 0.0268(5) Uani 1 1 d . . . C7 C 0.6623(2) 0.3880(2) 0.95304(16) 0.0243(6) Uani 1 1 d . . . C1 C 0.6784(3) 0.1778(3) 0.87981(16) 0.0380(7) Uani 1 1 d . . . H1A H 0.7404 0.1522 0.9178 0.046 Uiso 1 1 calc R . . C3 C 0.5506(3) 0.1353(3) 0.7574(2) 0.0524(9) Uani 1 1 d . . . H3A H 0.5273 0.0813 0.7138 0.063 Uiso 1 1 calc R . . C6 C 0.6216(3) 0.2954(2) 0.88808(16) 0.0254(6) Uani 1 1 d . . . C5 C 0.5290(3) 0.3329(3) 0.83044(18) 0.0395(7) Uani 1 1 d . . . H5A H 0.4909 0.4117 0.8357 0.047 Uiso 1 1 calc R . . C4 C 0.4936(3) 0.2517(3) 0.76480(19) 0.0459(9) Uani 1 1 d . . . H4A H 0.4318 0.2762 0.7264 0.055 Uiso 1 1 calc R . . C2 C 0.6413(4) 0.0986(3) 0.8139(2) 0.0524(10) Uani 1 1 d . . . H2A H 0.6788 0.0195 0.8083 0.063 Uiso 1 1 calc R . . O1 O 0.6579(2) 0.50262(17) 0.93782(11) 0.0359(5) Uani 1 1 d . . . H1 H 0.700(3) 0.264(3) 1.0443(17) 0.032(8) Uiso 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 N2 0.0309(13) 0.0149(11) 0.0199(11) -0.0015(8) -0.0043(9) -0.0008(8) Mn1 0.01598(16) 0.01598(16) 0.0160(2) 0.00092(16) -0.00092(16) 0.0000(2) N1 0.0349(13) 0.0120(11) 0.0208(10) -0.0009(8) -0.0044(9) -0.0007(9) N3 0.0467(15) 0.0200(11) 0.0253(11) 0.0028(9) -0.0102(11) -0.0010(11) N5 0.0224(11) 0.0160(12) 0.0209(11) -0.0009(8) -0.0038(9) -0.0022(8) C8 0.0178(13) 0.0185(13) 0.0214(13) 0.0005(10) 0.0021(10) 0.0019(10) N4 0.0349(14) 0.0228(12) 0.0228(11) 0.0001(9) -0.0084(10) 0.0012(9) C7 0.0276(16) 0.0211(13) 0.0242(14) -0.0010(10) -0.0024(11) 0.0021(11) C1 0.0574(19) 0.0279(15) 0.0286(15) -0.0035(13) -0.0076(14) 0.0052(17) C3 0.074(3) 0.048(2) 0.0351(18) -0.0175(16) -0.0067(18) -0.0194(18) C6 0.0361(15) 0.0204(14) 0.0196(13) 0.0006(11) -0.0011(11) -0.0021(11) C5 0.0418(18) 0.0349(18) 0.0417(18) -0.0015(14) -0.0094(14) 0.0019(14) C4 0.047(2) 0.054(2) 0.0366(19) -0.0046(16) -0.0130(16) -0.0129(16) C2 0.084(3) 0.0281(17) 0.0452(19) -0.0117(15) -0.0051(19) 0.0038(17) O1 0.0665(15) 0.0182(10) 0.0230(10) -0.0021(8) -0.0135(10) 0.0027(9) _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 N2 C8 1.344(3) . ? N2 N3 1.364(3) . ? N2 Mn1 2.300(2) 3_645 ? Mn1 O1 2.2079(18) . ? Mn1 O1 2.2079(18) 7_557 ? Mn1 N5 2.269(2) 7_557 ? Mn1 N5 2.269(2) . ? Mn1 N2 2.300(2) 5_657 ? Mn1 N2 2.300(2) 4_564 ? N1 C7 1.361(3) . ? N1 C8 1.393(3) . ? N1 H1 0.86(3) . ? N3 N4 1.299(3) . ? N5 C8 1.333(3) . ? N5 N4 1.366(3) . ? C7 O1 1.238(3) . ? C7 C6 1.484(3) . ? C1 C6 1.388(4) . ? C1 C2 1.394(4) . ? C1 H1A 0.9300 . ? C3 C2 1.368(5) . ? C3 C4 1.377(5) . ? C3 H3A 0.9300 . ? C6 C5 1.397(4) . ? C5 C4 1.399(4) . ? C5 H5A 0.9300 . ? C4 H4A 0.9300 . ? C2 H2A 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 C8 N2 N3 104.28(19) . . ? C8 N2 Mn1 148.09(16) . 3_645 ? N3 N2 Mn1 107.52(14) . 3_645 ? O1 Mn1 O1 87.19(11) . 7_557 ? O1 Mn1 N5 81.74(7) . 7_557 ? O1 Mn1 N5 75.18(7) 7_557 7_557 ? O1 Mn1 N5 75.18(7) . . ? O1 Mn1 N5 81.74(7) 7_557 . ? N5 Mn1 N5 147.99(10) 7_557 . ? O1 Mn1 N2 173.15(7) . 5_657 ? O1 Mn1 N2 91.85(7) 7_557 5_657 ? N5 Mn1 N2 104.58(7) 7_557 5_657 ? N5 Mn1 N2 97.97(7) . 5_657 ? O1 Mn1 N2 91.85(7) . 4_564 ? O1 Mn1 N2 173.15(7) 7_557 4_564 ? N5 Mn1 N2 97.97(7) 7_557 4_564 ? N5 Mn1 N2 104.58(7) . 4_564 ? N2 Mn1 N2 89.88(10) 5_657 4_564 ? C7 N1 C8 124.9(2) . . ? C7 N1 H1 125.8(18) . . ? C8 N1 H1 109.2(18) . . ? N4 N3 N2 109.43(19) . . ? C8 N5 N4 104.1(2) . . ? C8 N5 Mn1 130.91(16) . . ? N4 N5 Mn1 124.44(15) . . ? N5 C8 N2 112.1(2) . . ? N5 C8 N1 125.7(2) . . ? N2 C8 N1 122.1(2) . . ? N3 N4 N5 110.05(19) . . ? O1 C7 N1 122.2(2) . . ? O1 C7 C6 120.1(2) . . ? N1 C7 C6 117.7(2) . . ? C6 C1 C2 119.2(3) . . ? C6 C1 H1A 120.4 . . ? C2 C1 H1A 120.4 . . ? C2 C3 C4 120.4(3) . . ? C2 C3 H3A 119.8 . . ? C4 C3 H3A 119.8 . . ? C1 C6 C5 119.8(2) . . ? C1 C6 C7 122.2(2) . . ? C5 C6 C7 117.9(2) . . ? C6 C5 C4 119.9(3) . . ? C6 C5 H5A 120.1 . . ? C4 C5 H5A 120.1 . . ? C3 C4 C5 119.7(3) . . ? C3 C4 H4A 120.2 . . ? C5 C4 H4A 120.2 . . ? C3 C2 C1 121.0(3) . . ? C3 C2 H2A 119.5 . . ? C1 C2 H2A 119.5 . . ? C7 O1 Mn1 140.77(17) . . ? 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 C8 N2 N3 N4 -0.3(3) . . . . ? Mn1 N2 N3 N4 177.03(18) 3_645 . . . ? O1 Mn1 N5 C8 -6.5(2) . . . . ? O1 Mn1 N5 C8 82.8(2) 7_557 . . . ? N5 Mn1 N5 C8 38.8(2) 7_557 . . . ? N2 Mn1 N5 C8 173.5(2) 5_657 . . . ? N2 Mn1 N5 C8 -94.5(2) 4_564 . . . ? O1 Mn1 N5 N4 -176.6(2) . . . . ? O1 Mn1 N5 N4 -87.32(19) 7_557 . . . ? N5 Mn1 N5 N4 -131.29(19) 7_557 . . . ? N2 Mn1 N5 N4 3.41(19) 5_657 . . . ? N2 Mn1 N5 N4 95.38(19) 4_564 . . . ? N4 N5 C8 N2 -0.6(3) . . . . ? Mn1 N5 C8 N2 -172.19(15) . . . . ? N4 N5 C8 N1 177.5(2) . . . . ? Mn1 N5 C8 N1 5.9(4) . . . . ? N3 N2 C8 N5 0.6(3) . . . . ? Mn1 N2 C8 N5 -174.6(2) 3_645 . . . ? N3 N2 C8 N1 -177.6(2) . . . . ? Mn1 N2 C8 N1 7.3(5) 3_645 . . . ? C7 N1 C8 N5 -0.4(4) . . . . ? C7 N1 C8 N2 177.5(2) . . . . ? N2 N3 N4 N5 -0.1(3) . . . . ? C8 N5 N4 N3 0.4(3) . . . . ? Mn1 N5 N4 N3 172.69(18) . . . . ? C8 N1 C7 O1 -1.0(4) . . . . ? C8 N1 C7 C6 -179.6(2) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? C2 C1 C6 C7 -175.8(3) . . . . ? O1 C7 C6 C1 146.4(3) . . . . ? N1 C7 C6 C1 -35.0(4) . . . . ? O1 C7 C6 C5 -29.3(4) . . . . ? N1 C7 C6 C5 149.3(3) . . . . ? C1 C6 C5 C4 0.2(4) . . . . ? C7 C6 C5 C4 175.9(3) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C6 C5 C4 C3 -0.1(5) . . . . ? C4 C3 C2 C1 -0.3(5) . . . . ? C6 C1 C2 C3 0.3(5) . . . . ? N1 C7 O1 Mn1 -3.9(5) . . . . ? C6 C7 O1 Mn1 174.6(2) . . . . ? O1 Mn1 O1 C7 -76.0(3) 7_557 . . . ? N5 Mn1 O1 C7 -151.4(3) 7_557 . . . ? N5 Mn1 O1 C7 6.2(3) . . . . ? N2 Mn1 O1 C7 6.2(9) 5_657 . . . ? N2 Mn1 O1 C7 110.8(3) 4_564 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.196 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.058 #===END data_1B _database_code_depnum_ccdc_archive 'CCDC 782700' #TrackingRef '- Complexes 1A-1B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H12 Mn N10 O2' _chemical_formula_weight 431.30 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 Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 10.5430(15) _cell_length_b 10.5430(15) _cell_length_c 15.766(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1752.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 17902 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.5 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 0.793 _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 SCX-MINI _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean none _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 18722 _diffrn_reflns_av_R_equivalents 0.0523 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2016 _reflns_number_gt 1921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0319P)^2^+0.2132P] 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 0.02(2) _refine_ls_number_reflns 2016 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0696 _refine_ls_wR_factor_gt 0.0685 _refine_ls_goodness_of_fit_ref 1.200 _refine_ls_restrained_S_all 1.200 _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 Mn1 Mn -0.18708(3) 0.81292(3) 1.0000 0.01578(11) Uani 1 2 d S . . N1 N 0.15783(14) 0.79927(17) 1.02935(10) 0.0227(4) Uani 1 1 d . . . H1 H 0.2388 0.7999 1.0362 0.047(8) Uiso 1 1 calc R . . N4 N 0.03271(15) 0.6981(2) 1.22082(11) 0.0293(4) Uani 1 1 d . . . N2 N -0.04216(15) 0.75142(15) 1.09712(10) 0.0190(4) Uani 1 1 d . . . C8 C 0.08390(19) 0.75892(18) 1.09681(12) 0.0190(4) Uani 1 1 d . . . N3 N -0.07052(17) 0.71286(18) 1.17742(10) 0.0261(4) Uani 1 1 d . . . C7 C 0.11154(19) 0.8380(2) 0.95304(13) 0.0237(5) Uani 1 1 d . . . C5 C 0.3221(2) 0.8219(3) 0.87969(14) 0.0366(5) Uani 1 1 d . . . H5A H 0.3478 0.7595 0.9177 0.031(6) Uiso 1 1 calc R . . C3 C 0.3649(3) 0.9500(3) 0.75711(17) 0.0514(7) Uani 1 1 d . . . H3A H 0.4191 0.9736 0.7134 0.075(10) Uiso 1 1 calc R . . C6 C 0.2044(2) 0.8783(2) 0.88820(13) 0.0254(5) Uani 1 1 d . . . C1 C 0.1669(2) 0.9711(2) 0.83039(15) 0.0384(6) Uani 1 1 d . . . H1A H 0.0879 1.0094 0.8356 0.045(8) Uiso 1 1 calc R . . C2 C 0.2482(3) 1.0062(3) 0.76466(16) 0.0456(7) Uani 1 1 d . . . H2A H 0.2233 1.0679 0.7259 0.036(7) Uiso 1 1 calc R . . C4 C 0.4015(2) 0.8590(3) 0.81407(17) 0.0518(8) Uani 1 1 d . . . H4A H 0.4810 0.8215 0.8087 0.053(8) Uiso 1 1 calc R . . N5 N 0.13431(15) 0.72558(16) 1.17157(10) 0.0222(4) Uani 1 1 d . . . O1 O -0.00308(14) 0.84239(17) 0.93772(9) 0.0355(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 Mn1 0.01604(13) 0.01604(13) 0.01526(18) 0.00080(12) -0.00080(12) -0.00037(17) N1 0.0142(8) 0.0341(10) 0.0198(8) 0.0048(7) 0.0019(6) -0.0014(7) N4 0.0183(8) 0.0448(11) 0.0248(9) 0.0078(9) -0.0009(7) -0.0008(9) N2 0.0166(9) 0.0223(9) 0.0182(8) 0.0028(7) 0.0007(6) -0.0007(7) C8 0.0174(10) 0.0194(10) 0.0203(10) -0.0017(8) -0.0012(8) 0.0010(8) N3 0.0221(9) 0.0347(11) 0.0214(9) 0.0090(8) -0.0001(7) 0.0012(7) C7 0.0201(10) 0.0286(12) 0.0222(10) 0.0023(8) 0.0010(8) 0.0023(9) C5 0.0278(11) 0.0535(15) 0.0287(12) 0.0070(11) 0.0031(10) 0.0044(13) C3 0.0493(16) 0.070(2) 0.0348(14) 0.0069(14) 0.0160(13) -0.0188(14) C6 0.0225(11) 0.0345(12) 0.0193(10) 0.0019(9) 0.0012(8) -0.0032(9) C1 0.0359(14) 0.0405(14) 0.0387(14) 0.0095(11) 0.0026(11) -0.0011(11) C2 0.0568(18) 0.0443(15) 0.0357(15) 0.0121(12) 0.0032(13) -0.0134(13) C4 0.0270(14) 0.084(2) 0.0448(15) 0.0021(15) 0.0121(12) 0.0024(14) N5 0.0150(8) 0.0321(10) 0.0194(8) 0.0040(7) 0.0011(7) 0.0004(7) O1 0.0177(8) 0.0658(12) 0.0231(8) 0.0127(8) 0.0008(6) 0.0032(7) _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 2.1964(15) 7_467 ? Mn1 O1 2.1964(15) . ? Mn1 N2 2.2583(16) . ? Mn1 N2 2.2583(16) 7_467 ? Mn1 N5 2.2890(17) 6_467 ? Mn1 N5 2.2890(17) 3_554 ? N1 C7 1.361(2) . ? N1 C8 1.386(2) . ? N1 H1 0.8600 . ? N4 N3 1.295(2) . ? N4 N5 1.355(2) . ? N2 C8 1.331(3) . ? N2 N3 1.363(2) . ? C8 N5 1.340(2) . ? C7 O1 1.233(2) . ? C7 C6 1.478(3) . ? C5 C6 1.383(3) . ? C5 C4 1.387(3) . ? C5 H5A 0.9300 . ? C3 C4 1.370(4) . ? C3 C2 1.370(4) . ? C3 H3A 0.9300 . ? C6 C1 1.394(3) . ? C1 C2 1.395(3) . ? C1 H1A 0.9300 . ? C2 H2A 0.9300 . ? C4 H4A 0.9300 . ? N5 Mn1 2.2890(17) 4_455 ? 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 O1 87.13(10) 7_467 . ? O1 Mn1 N2 81.64(6) 7_467 . ? O1 Mn1 N2 75.29(6) . . ? O1 Mn1 N2 75.29(6) 7_467 7_467 ? O1 Mn1 N2 81.64(6) . 7_467 ? N2 Mn1 N2 148.02(8) . 7_467 ? O1 Mn1 N5 91.80(6) 7_467 6_467 ? O1 Mn1 N5 173.31(6) . 6_467 ? N2 Mn1 N5 98.01(6) . 6_467 ? N2 Mn1 N5 104.48(6) 7_467 6_467 ? O1 Mn1 N5 173.31(6) 7_467 3_554 ? O1 Mn1 N5 91.80(6) . 3_554 ? N2 Mn1 N5 104.48(6) . 3_554 ? N2 Mn1 N5 98.01(6) 7_467 3_554 ? N5 Mn1 N5 90.01(9) 6_467 3_554 ? C7 N1 C8 124.68(16) . . ? C7 N1 H1 117.7 . . ? C8 N1 H1 117.7 . . ? N3 N4 N5 109.63(15) . . ? C8 N2 N3 103.89(16) . . ? C8 N2 Mn1 130.99(13) . . ? N3 N2 Mn1 124.55(12) . . ? N2 C8 N5 112.16(17) . . ? N2 C8 N1 125.63(17) . . ? N5 C8 N1 122.19(18) . . ? N4 N3 N2 110.03(16) . . ? O1 C7 N1 122.40(18) . . ? O1 C7 C6 120.18(18) . . ? N1 C7 C6 117.40(17) . . ? C6 C5 C4 119.5(2) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C4 C3 C2 120.0(2) . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C5 C6 C1 119.5(2) . . ? C5 C6 C7 122.53(19) . . ? C1 C6 C7 117.8(2) . . ? C6 C1 C2 119.9(2) . . ? C6 C1 H1A 120.1 . . ? C2 C1 H1A 120.1 . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C8 N5 N4 104.29(16) . . ? C8 N5 Mn1 148.00(13) . 4_455 ? N4 N5 Mn1 107.63(11) . 4_455 ? C7 O1 Mn1 140.58(14) . . ? 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 O1 Mn1 N2 C8 -82.56(17) 7_467 . . . ? O1 Mn1 N2 C8 6.65(17) . . . . ? N2 Mn1 N2 C8 -38.59(16) 7_467 . . . ? N5 Mn1 N2 C8 -173.21(17) 6_467 . . . ? N5 Mn1 N2 C8 94.69(17) 3_554 . . . ? O1 Mn1 N2 N3 87.30(16) 7_467 . . . ? O1 Mn1 N2 N3 176.51(16) . . . . ? N2 Mn1 N2 N3 131.27(15) 7_467 . . . ? N5 Mn1 N2 N3 -3.35(15) 6_467 . . . ? N5 Mn1 N2 N3 -95.45(16) 3_554 . . . ? N3 N2 C8 N5 0.9(2) . . . . ? Mn1 N2 C8 N5 172.30(12) . . . . ? N3 N2 C8 N1 -177.43(18) . . . . ? Mn1 N2 C8 N1 -6.0(3) . . . . ? C7 N1 C8 N2 0.3(3) . . . . ? C7 N1 C8 N5 -177.9(2) . . . . ? N5 N4 N3 N2 -0.2(2) . . . . ? C8 N2 N3 N4 -0.4(2) . . . . ? Mn1 N2 N3 N4 -172.55(15) . . . . ? C8 N1 C7 O1 1.3(3) . . . . ? C8 N1 C7 C6 179.81(19) . . . . ? C4 C5 C6 C1 0.4(4) . . . . ? C4 C5 C6 C7 175.9(2) . . . . ? O1 C7 C6 C5 -146.3(2) . . . . ? N1 C7 C6 C5 35.1(3) . . . . ? O1 C7 C6 C1 29.3(3) . . . . ? N1 C7 C6 C1 -149.3(2) . . . . ? C5 C6 C1 C2 -0.1(4) . . . . ? C7 C6 C1 C2 -175.8(2) . . . . ? C4 C3 C2 C1 0.1(4) . . . . ? C6 C1 C2 C3 -0.2(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C6 C5 C4 C3 -0.5(4) . . . . ? N2 C8 N5 N4 -1.0(2) . . . . ? N1 C8 N5 N4 177.38(18) . . . . ? N2 C8 N5 Mn1 174.87(18) . . . 4_455 ? N1 C8 N5 Mn1 -6.7(4) . . . 4_455 ? N3 N4 N5 C8 0.7(2) . . . . ? N3 N4 N5 Mn1 -177.00(15) . . . 4_455 ? N1 C7 O1 Mn1 3.7(4) . . . . ? C6 C7 O1 Mn1 -174.80(17) . . . . ? O1 Mn1 O1 C7 75.9(2) 7_467 . . . ? N2 Mn1 O1 C7 -6.2(2) . . . . ? N2 Mn1 O1 C7 151.5(2) 7_467 . . . ? N5 Mn1 O1 C7 -5.0(7) 6_467 . . . ? N5 Mn1 O1 C7 -110.7(2) 3_554 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.209 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.067