# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Subrata Mukhopadhyay' _publ_contact_author_email 'JU SUBRATA@YAHOO.CO.IN' _publ_section_title ; Robust recognition of malonate and picoline in (C6H8N2H)2[M(C3H2O4)2(H2O)2]*4H2O (M = Ni/Co/Mn) compounds: Role of this highly stable hydrogen-bonded motif in driving the supramolecular self-assembly ; loop_ _publ_author_name 'Subrata Mukhopadhyay' 'Chih-Yuen Chen' 'Somnath Ray Choudhury' 'Suranjana Das' 'Biswajit Dey' 'Patrick Gamez' ; A.D.Jana ; 'Hon Man Lee' 'Arturo Robertazzi' # Attachment '1.cif' data_h2 _database_code_depnum_ccdc_archive 'CCDC 676210' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 Ni O10, 2(C6 H9 N2), 4(H2 O)' _chemical_formula_sum 'C18 H34 N4 Ni O14' _chemical_formula_weight 589.20 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' Ni Ni 0.3393 1.1124 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4284(2) _cell_length_b 8.9640(2) _cell_length_c 10.5124(2) _cell_angle_alpha 94.6690(10) _cell_angle_beta 92.1650(10) _cell_angle_gamma 111.4180(10) _cell_volume 647.78(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description green _exptl_crystal_colour parallelepipe _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6837 _exptl_absorpt_correction_T_max 0.7903 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9820 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0167 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.63 _reflns_number_total 3285 _reflns_number_gt 3133 _reflns_threshold_expression I>2\s _computing_data_collection 'APEX2 v1.0-22 (Bruker, 2004)' _computing_cell_refinement 'SAINT v6.280a (Bruker, 2004)' _computing_data_reduction 'SAINT v6.280a (Bruker, 2004)' _computing_structure_solution 'SHELXTL 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL 5.1' _computing_molecular_graphics 'SHELXTL 5.1' _computing_publication_material 'SHELXTL 5.1' _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^)+(0.0282P)^2^+0.2662P] 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 SHELXL _refine_ls_extinction_coef 0.053(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3285 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0237 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0610 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.003 _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 0.65775(15) 0.34408(13) -0.03591(11) 0.0148(2) Uani 1 1 d . . . C2 C 0.59254(16) 0.37020(13) 0.09681(11) 0.0163(2) Uani 1 1 d . . . H2A H 0.4497 0.3370 0.0904 0.020 Uiso 1 1 calc R . . H2B H 0.6484 0.4868 0.1259 0.020 Uiso 1 1 calc R . . C3 C 0.64902(16) 0.27950(13) 0.19781(11) 0.0161(2) Uani 1 1 d . . . C4 C 0.2044(2) 0.30005(18) 0.33215(14) 0.0308(3) Uani 1 1 d . . . H4A H 0.0957 0.3321 0.3541 0.046 Uiso 1 1 calc R . . H4B H 0.1703 0.2308 0.2510 0.046 Uiso 1 1 calc R . . H4C H 0.3191 0.3963 0.3236 0.046 Uiso 1 1 calc R . . C7 C 0.24731(18) 0.20956(15) 0.43592(12) 0.0219(2) Uani 1 1 d . . . C8 C 0.3113(2) 0.28799(16) 0.56105(13) 0.0258(3) Uani 1 1 d . . . H8 H 0.3278 0.3979 0.5796 0.031 Uiso 1 1 calc R . . C9 C 0.3489(2) 0.20475(16) 0.65418(13) 0.0255(3) Uani 1 1 d . . . H9 H 0.3942 0.2576 0.7377 0.031 Uiso 1 1 calc R . . C5 C 0.26110(17) -0.03441(14) 0.51152(11) 0.0187(2) Uani 1 1 d . . . C6 C 0.22446(18) 0.05109(15) 0.41239(12) 0.0209(2) Uani 1 1 d . . . H2 H 0.347(3) -0.003(2) 0.6874(17) 0.032(4) Uiso 1 1 d . . . H6 H 0.189(2) -0.002(2) 0.3316(17) 0.028(4) Uiso 1 1 d . . . H6A H -0.049(3) 0.558(2) 0.2810(18) 0.039(5) Uiso 1 1 d . . . H7A H 0.949(3) 0.731(2) 0.122(2) 0.047(6) Uiso 1 1 d . . . H5B H 0.141(3) -0.062(3) 0.0223(19) 0.045(5) Uiso 1 1 d . . . H6B H 0.111(3) 0.604(2) 0.2171(19) 0.039(5) Uiso 1 1 d . . . H7B H 0.872(3) 0.674(3) 0.007(2) 0.043(5) Uiso 1 1 d . . . N1 N 0.23903(16) -0.18845(13) 0.49314(10) 0.0241(2) Uani 1 1 d . . . H1A H 0.2641 -0.2371 0.5571 0.029 Uiso 1 1 calc R . . H1B H 0.1993 -0.2420 0.4170 0.029 Uiso 1 1 calc R . . N2 N 0.32224(15) 0.04609(13) 0.62912(10) 0.0200(2) Uani 1 1 d . . . Ni1 Ni 0.5000 0.0000 0.0000 0.01289(7) Uani 1 2 d S . . O1 O 0.60680(12) 0.20202(9) -0.08954(8) 0.01755(17) Uani 1 1 d . . . O2 O 0.75585(13) 0.46626(10) -0.08850(8) 0.02058(18) Uani 1 1 d . . . O3 O 0.60954(13) 0.12927(10) 0.17431(8) 0.02035(18) Uani 1 1 d . . . O4 O 0.73055(13) 0.35866(10) 0.30153(8) 0.02269(19) Uani 1 1 d . . . O5 O 0.23710(13) 0.02515(11) 0.02449(10) 0.0246(2) Uani 1 1 d . . . H5A H 0.2179 0.0820 -0.0302 0.037 Uiso 1 1 calc R . . O6 O 0.03944(14) 0.63631(11) 0.26085(9) 0.02184(18) Uani 1 1 d . . . O7 O 0.91408(13) 0.75762(11) 0.05607(10) 0.02256(19) 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 0.0145(5) 0.0138(5) 0.0167(5) 0.0028(4) -0.0013(4) 0.0060(4) C2 0.0188(5) 0.0121(5) 0.0185(5) 0.0022(4) 0.0016(4) 0.0061(4) C3 0.0172(5) 0.0133(5) 0.0163(5) 0.0024(4) 0.0021(4) 0.0036(4) C4 0.0338(7) 0.0352(7) 0.0297(7) 0.0158(6) 0.0053(5) 0.0174(6) C7 0.0196(5) 0.0258(6) 0.0227(6) 0.0085(5) 0.0046(4) 0.0099(5) C8 0.0322(7) 0.0225(6) 0.0262(6) 0.0029(5) 0.0035(5) 0.0142(5) C9 0.0326(7) 0.0247(6) 0.0207(6) -0.0014(5) 0.0003(5) 0.0135(5) C5 0.0168(5) 0.0209(5) 0.0180(5) 0.0040(4) 0.0024(4) 0.0060(4) C6 0.0217(6) 0.0243(6) 0.0159(5) 0.0039(5) 0.0001(4) 0.0075(5) N1 0.0318(6) 0.0199(5) 0.0193(5) 0.0029(4) -0.0022(4) 0.0085(4) N2 0.0246(5) 0.0221(5) 0.0152(5) 0.0041(4) 0.0005(4) 0.0106(4) Ni1 0.01323(11) 0.00933(10) 0.01509(11) 0.00144(7) -0.00097(7) 0.00313(7) O1 0.0221(4) 0.0120(4) 0.0173(4) 0.0020(3) 0.0009(3) 0.0047(3) O2 0.0269(4) 0.0128(4) 0.0213(4) 0.0055(3) 0.0052(3) 0.0053(3) O3 0.0292(4) 0.0119(4) 0.0177(4) 0.0016(3) -0.0035(3) 0.0054(3) O4 0.0323(5) 0.0149(4) 0.0165(4) -0.0001(3) -0.0018(3) 0.0043(3) O5 0.0157(4) 0.0162(4) 0.0429(6) 0.0090(4) 0.0031(4) 0.0057(3) O6 0.0230(4) 0.0184(4) 0.0212(4) 0.0013(3) 0.0032(3) 0.0043(4) O7 0.0226(4) 0.0132(4) 0.0305(5) 0.0047(4) -0.0029(4) 0.0050(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 1.2579(14) . ? C1 O1 1.2639(13) . ? C1 C2 1.5222(16) . ? C2 C3 1.5232(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O4 1.2528(14) . ? C3 O3 1.2699(13) . ? C4 C7 1.5021(17) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C7 C6 1.3680(18) . ? C7 C8 1.4173(19) . ? C8 C9 1.3578(18) . ? C8 H8 0.9500 . ? C9 N2 1.3641(16) . ? C9 H9 0.9500 . ? C5 N1 1.3265(16) . ? C5 N2 1.3522(16) . ? C5 C6 1.4172(16) . ? C6 H6 0.919(17) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2 0.834(18) . ? Ni1 O1 2.0198(8) 2_655 ? Ni1 O1 2.0198(8) . ? Ni1 O3 2.0532(8) . ? Ni1 O3 2.0532(8) 2_655 ? Ni1 O5 2.0691(9) . ? Ni1 O5 2.0691(9) 2_655 ? O5 H5B 0.84(2) . ? O5 H5A 0.8400 . ? O6 H6A 0.81(2) . ? O6 H6B 0.83(2) . ? O7 H7A 0.82(2) . ? O7 H7B 0.83(2) . ? 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 123.09(10) . . ? O2 C1 C2 118.00(10) . . ? O1 C1 C2 118.88(9) . . ? C1 C2 C3 114.94(9) . . ? C1 C2 H2A 108.5 . . ? C3 C2 H2A 108.5 . . ? C1 C2 H2B 108.5 . . ? C3 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? O4 C3 O3 123.47(10) . . ? O4 C3 C2 117.30(10) . . ? O3 C3 C2 119.23(10) . . ? C7 C4 H4A 109.5 . . ? C7 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C7 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C7 C8 118.85(11) . . ? C6 C7 C4 121.16(12) . . ? C8 C7 C4 119.99(12) . . ? C9 C8 C7 119.45(12) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 N2 120.74(12) . . ? C8 C9 H9 119.6 . . ? N2 C9 H9 119.6 . . ? N1 C5 N2 119.24(11) . . ? N1 C5 C6 122.75(11) . . ? N2 C5 C6 118.00(11) . . ? C7 C6 C5 120.80(11) . . ? C7 C6 H6 121.2(10) . . ? C5 C6 H6 117.9(10) . . ? C5 N1 H1A 120.0 . . ? C5 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C5 N2 C9 122.15(11) . . ? C5 N2 H2 118.6(12) . . ? C9 N2 H2 119.2(12) . . ? O1 Ni1 O1 180.0 2_655 . ? O1 Ni1 O3 89.15(3) 2_655 . ? O1 Ni1 O3 90.86(3) . . ? O1 Ni1 O3 90.86(3) 2_655 2_655 ? O1 Ni1 O3 89.14(3) . 2_655 ? O3 Ni1 O3 180.0 . 2_655 ? O1 Ni1 O5 86.50(3) 2_655 . ? O1 Ni1 O5 93.50(3) . . ? O3 Ni1 O5 90.37(4) . . ? O3 Ni1 O5 89.63(4) 2_655 . ? O1 Ni1 O5 93.50(3) 2_655 2_655 ? O1 Ni1 O5 86.50(3) . 2_655 ? O3 Ni1 O5 89.63(4) . 2_655 ? O3 Ni1 O5 90.37(4) 2_655 2_655 ? O5 Ni1 O5 180.0 . 2_655 ? C1 O1 Ni1 125.09(7) . . ? C3 O3 Ni1 124.47(7) . . ? Ni1 O5 H5B 114.9(14) . . ? Ni1 O5 H5A 109.5 . . ? H5B O5 H5A 110.1 . . ? H6A O6 H6B 108.2(18) . . ? H7A O7 H7B 104.5(19) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.63 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.478 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.046 # Attachment '2.cif' data_h3 _database_code_depnum_ccdc_archive 'CCDC 676211' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C6 H8 Co O10, 2(C6 H9 N2), 4(H2 O)' _chemical_formula_sum 'C18 H34 Co N4 O14' _chemical_formula_weight 589.42 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' Co Co 0.3494 0.9721 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5389(2) _cell_length_b 9.0543(2) _cell_length_c 10.4107(3) _cell_angle_alpha 93.349(2) _cell_angle_beta 93.305(2) _cell_angle_gamma 112.0980(10) _cell_volume 654.86(3) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rhombus _exptl_crystal_colour pink _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 309 _exptl_absorpt_coefficient_mu 0.729 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7121 _exptl_absorpt_correction_T_max 0.9373 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9535 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.74 _reflns_number_total 3376 _reflns_number_gt 3045 _reflns_threshold_expression I>2\s _computing_data_collection 'APEX2 v1.0-22 (Bruker, 2004)' _computing_cell_refinement 'SAINT v6.280a (Bruker, 2004)' _computing_data_reduction 'SAINT v6.280a (Bruker, 2004)' _computing_structure_solution 'SHELXTL 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL 5.1' _computing_molecular_graphics 'SHELXTL 5.1' _computing_publication_material 'SHELXTL 5.1' _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^+0.2375P] 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_number_reflns 3376 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0673 _refine_ls_wR_factor_gt 0.0662 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.016 _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 0.33481(17) 0.15128(14) 0.53840(11) 0.0158(2) Uani 1 1 d . . . C2 C 0.41216(18) 0.12581(14) 0.41023(12) 0.0175(2) Uani 1 1 d . . . H2B H 0.5533 0.1592 0.4244 0.021 Uiso 1 1 calc R . . H2A H 0.3576 0.0101 0.3819 0.021 Uiso 1 1 calc R . . C3 C 0.36738(18) 0.21637(15) 0.30210(12) 0.0187(2) Uani 1 1 d . . . C4 C 0.8037(2) 0.2057(2) 0.16993(15) 0.0347(3) Uani 1 1 d . . . H4A H 0.8433 0.2744 0.2512 0.052 Uiso 1 1 calc R . . H4B H 0.9080 0.1726 0.1463 0.052 Uiso 1 1 calc R . . H4C H 0.6891 0.1109 0.1807 0.052 Uiso 1 1 calc R . . C5 C 0.74009(19) 0.53912(16) -0.01047(12) 0.0211(2) Uani 1 1 d . . . C6 C 0.78120(19) 0.45321(17) 0.08914(12) 0.0233(3) Uani 1 1 d . . . H6 H 0.8239 0.5102 0.1780 0.028 Uiso 1 1 d R . . C7 C 0.7586(2) 0.29679(17) 0.06502(13) 0.0247(3) Uani 1 1 d . . . C8 C 0.6920(2) 0.22095(18) -0.06088(14) 0.0287(3) Uani 1 1 d . . . H8 H 0.6760 0.1126 -0.0798 0.034 Uiso 1 1 calc R . . C9 C 0.6510(2) 0.30445(18) -0.15438(13) 0.0286(3) Uani 1 1 d . . . Co2 Co 0.5000 0.5000 0.5000 0.01434(7) Uani 1 2 d S . . H5A H 0.8013 0.4180 0.5313 0.036 Uiso 1 1 d . . . H5B H 0.8541 0.5645 0.5042 0.045 Uiso 1 1 d . . . H7B H 0.1314 0.8345 0.5043 0.062 Uiso 1 1 d . . . H6A H -0.0623 0.0556 0.7767 0.040 Uiso 1 1 d . . . H9 H 0.6044 0.2639 -0.2395 0.040 Uiso 1 1 d . . . N2 N 0.67588(17) 0.46084(14) -0.12873(10) 0.0227(2) Uani 1 1 d . . . H2 H 0.6492 0.5124 -0.1913 0.027 Uiso 1 1 calc R . . N1 N 0.76044(18) 0.69109(14) 0.00825(11) 0.0266(2) Uani 1 1 d . . . H1a H 0.7450 0.7509 -0.0601 0.032 Uiso 1 1 d R . . H1b H 0.8170 0.7452 0.0856 0.032 Uiso 1 1 d R . . O1 O 0.37938(13) 0.29211(10) 0.58811(8) 0.01958(18) Uani 1 1 d . . . O2 O 0.23375(14) 0.02964(10) 0.59094(9) 0.02192(19) Uani 1 1 d . . . O3 O 0.42228(16) 0.36718(11) 0.32041(9) 0.0270(2) Uani 1 1 d . . . O4 O 0.28130(15) 0.13716(11) 0.19927(9) 0.0249(2) Uani 1 1 d . . . O5 O 0.77061(15) 0.48908(13) 0.51892(16) 0.0475(4) Uani 1 1 d . . . O7 O 0.08316(14) 0.74141(11) 0.45288(10) 0.0238(2) Uani 1 1 d . . . H7A H 0.0411 0.7696 0.3758 0.050 Uiso 1 1 d . . . O6 O 0.03284(14) 0.13517(11) 0.75885(9) 0.0238(2) Uani 1 1 d . . . H6B H 0.1002 0.1095 0.7213 0.036 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 C1 0.0147(5) 0.0146(5) 0.0182(5) 0.0028(4) -0.0013(4) 0.0060(4) C2 0.0197(6) 0.0132(5) 0.0207(6) 0.0025(4) 0.0027(4) 0.0072(5) C3 0.0216(6) 0.0146(5) 0.0191(6) 0.0028(4) 0.0046(5) 0.0056(5) C4 0.0397(9) 0.0377(9) 0.0330(8) 0.0166(7) 0.0058(6) 0.0196(7) C5 0.0191(6) 0.0228(6) 0.0204(6) 0.0041(5) 0.0033(5) 0.0065(5) C6 0.0242(6) 0.0264(7) 0.0184(6) 0.0048(5) 0.0015(5) 0.0085(5) C7 0.0224(6) 0.0285(7) 0.0260(6) 0.0104(5) 0.0056(5) 0.0112(5) C8 0.0360(8) 0.0237(7) 0.0303(7) 0.0034(6) 0.0047(6) 0.0153(6) C9 0.0370(8) 0.0271(7) 0.0227(6) -0.0010(5) 0.0003(6) 0.0141(6) Co2 0.01381(12) 0.01058(11) 0.01809(12) 0.00195(8) 0.00052(8) 0.00407(8) N2 0.0284(6) 0.0233(6) 0.0174(5) 0.0042(4) 0.0009(4) 0.0108(5) N1 0.0351(7) 0.0215(6) 0.0216(5) 0.0023(4) -0.0015(5) 0.0095(5) O1 0.0246(5) 0.0127(4) 0.0201(4) 0.0018(3) 0.0033(3) 0.0054(4) O2 0.0274(5) 0.0134(4) 0.0240(4) 0.0052(3) 0.0063(4) 0.0057(4) O3 0.0455(6) 0.0131(4) 0.0191(4) 0.0023(3) -0.0014(4) 0.0078(4) O4 0.0346(5) 0.0171(4) 0.0187(4) 0.0005(3) -0.0006(4) 0.0055(4) O5 0.0161(5) 0.0183(5) 0.1123(11) 0.0234(6) 0.0111(6) 0.0079(4) O7 0.0216(5) 0.0141(4) 0.0347(5) 0.0034(4) -0.0019(4) 0.0061(4) O6 0.0244(5) 0.0210(5) 0.0235(4) 0.0005(4) 0.0049(4) 0.0057(4) _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 1.2568(15) . ? C1 O1 1.2598(14) . ? C1 C2 1.5259(17) . ? C2 C3 1.5251(16) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 O4 1.2496(16) . ? C3 O3 1.2679(15) . ? C4 C7 1.5039(18) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N1 1.3272(17) . ? C5 N2 1.3504(17) . ? C5 C6 1.4195(17) . ? C6 C7 1.367(2) . ? C6 H6 1.0049 . ? C7 C8 1.415(2) . ? C8 C9 1.357(2) . ? C8 H8 0.9500 . ? C9 N2 1.3644(18) . ? C9 H9 0.9344 . ? Co2 O1 2.0546(8) . ? Co2 O1 2.0547(8) 2_666 ? Co2 O5 2.0780(10) 2_666 ? Co2 O5 2.0780(10) . ? Co2 O3 2.0895(9) 2_666 ? Co2 O3 2.0895(9) . ? N2 H2 0.8800 . ? N1 H1a 0.9471 . ? N1 H1b 0.9097 . ? O5 H5A 0.7764 . ? O5 H5B 0.7656 . ? O7 H7B 0.9077 . ? O7 H7A 0.9302 . ? O6 H6A 0.8430 . ? O6 H6B 0.7520 . ? 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 123.24(11) . . ? O2 C1 C2 117.99(11) . . ? O1 C1 C2 118.74(10) . . ? C3 C2 C1 114.57(10) . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? H2B C2 H2A 107.6 . . ? O4 C3 O3 123.78(11) . . ? O4 C3 C2 117.72(11) . . ? O3 C3 C2 118.49(11) . . ? C7 C4 H4A 109.5 . . ? C7 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C7 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 N2 119.21(11) . . ? N1 C5 C6 122.90(12) . . ? N2 C5 C6 117.89(12) . . ? C7 C6 C5 120.75(13) . . ? C7 C6 H6 121.4 . . ? C5 C6 H6 117.8 . . ? C6 C7 C8 118.97(12) . . ? C6 C7 C4 120.95(13) . . ? C8 C7 C4 120.07(13) . . ? C9 C8 C7 119.39(13) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 N2 120.79(13) . . ? C8 C9 H9 125.3 . . ? N2 C9 H9 113.9 . . ? O1 Co2 O1 180.00(5) . 2_666 ? O1 Co2 O5 88.01(4) . 2_666 ? O1 Co2 O5 91.99(4) 2_666 2_666 ? O1 Co2 O5 91.99(4) . . ? O1 Co2 O5 88.01(4) 2_666 . ? O5 Co2 O5 180.00(6) 2_666 . ? O1 Co2 O3 90.63(4) . 2_666 ? O1 Co2 O3 89.37(4) 2_666 2_666 ? O5 Co2 O3 94.15(5) 2_666 2_666 ? O5 Co2 O3 85.85(5) . 2_666 ? O1 Co2 O3 89.37(4) . . ? O1 Co2 O3 90.63(4) 2_666 . ? O5 Co2 O3 85.85(5) 2_666 . ? O5 Co2 O3 94.15(5) . . ? O3 Co2 O3 180.0 2_666 . ? C5 N2 C9 122.19(11) . . ? C5 N2 H2 118.9 . . ? C9 N2 H2 118.9 . . ? C5 N1 H1a 122.6 . . ? C5 N1 H1b 117.9 . . ? H1a N1 H1b 118.0 . . ? C1 O1 Co2 127.03(8) . . ? C3 O3 Co2 125.52(8) . . ? Co2 O5 H5A 130.8 . . ? Co2 O5 H5B 115.6 . . ? H5A O5 H5B 113.2 . . ? H7B O7 H7A 104.1 . . ? H6A O6 H6B 111.3 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.74 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.386 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.048 # Attachment '3.cif' data_h4 _database_code_depnum_ccdc_archive 'CCDC 676212' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H8 Mn O10, 2(C6 H9 N2), 4(H2 O)' _chemical_formula_sum 'C18 H34 Mn N4 O14' _chemical_formula_weight 585.43 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' Mn Mn 0.3368 0.7283 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6690(6) _cell_length_b 9.1074(7) _cell_length_c 10.3380(8) _cell_angle_alpha 92.7760(10) _cell_angle_beta 92.5580(10) _cell_angle_gamma 111.7340(10) _cell_volume 668.41(9) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelepipe _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 307 _exptl_absorpt_coefficient_mu 0.566 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7651 _exptl_absorpt_correction_T_max 0.8486 _exptl_absorpt_process_details 'SADABS 2.10 (Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 7406 _diffrn_reflns_av_R_equivalents 0.0138 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.64 _reflns_number_total 3390 _reflns_number_gt 3070 _reflns_threshold_expression I>2\s _computing_data_collection 'APEX2 v1.0-22 (Bruker, 2004)' _computing_cell_refinement 'SAINT v6.280a (Bruker, 2004)' _computing_data_reduction 'SAINT v6.280a (Bruker, 2004)' _computing_structure_solution 'SHELXTL 5.1 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL 5.1' _computing_molecular_graphics 'SHELXTL 5.1' _computing_publication_material 'SHELXTL 5.1' _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^)+(0.0328P)^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_number_reflns 3390 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.643 _refine_ls_restrained_S_all 1.643 _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 0.66872(16) 0.85668(13) -0.03590(11) 0.0169(2) Uani 1 1 d . . . C2 C 0.58790(17) 0.88045(14) 0.09232(11) 0.0194(2) Uani 1 1 d . . . H2A H 0.6400 0.9948 0.1203 0.023 Uiso 1 1 calc R . . H2B H 0.4499 0.8478 0.0774 0.023 Uiso 1 1 calc R . . C3 C 0.62844(17) 0.78892(14) 0.20182(11) 0.0192(2) Uani 1 1 d . . . C4 C 0.1942(2) 0.7937(2) 0.33337(15) 0.0392(4) Uani 1 1 d . . . H4A H 0.1547 0.7285 0.2513 0.059 Uiso 1 1 calc R . . H4B H 0.3062 0.8878 0.3218 0.059 Uiso 1 1 calc R . . H4C H 0.0923 0.8265 0.3601 0.059 Uiso 1 1 calc R . . C5 C 0.25738(17) 0.45640(15) 0.50764(11) 0.0221(2) Uani 1 1 d . . . C6 C 0.21574(19) 0.54451(16) 0.41028(12) 0.0258(3) Uani 1 1 d . . . C7 C 0.23903(19) 0.69932(16) 0.43585(13) 0.0270(3) Uani 1 1 d . . . C8 C 0.3071(2) 0.77105(17) 0.56221(13) 0.0309(3) Uani 1 1 d . . . H8 H 0.3231 0.8783 0.5826 0.037 Uiso 1 1 calc R . . C9 C 0.3491(2) 0.68564(16) 0.65335(13) 0.0306(3) Uani 1 1 d . . . H9 H 0.3968 0.7341 0.7376 0.037 Uiso 1 1 calc R . . H6 H 0.1785 0.4996 0.3304 0.037 Uiso 1 1 d . . . H5A H 0.8107 0.4147 0.0402 0.046 Uiso 1 1 d . . . H6A H -0.0527 0.0530 0.2764 0.037 Uiso 1 1 d . . . H7A H 0.9550 0.2337 0.1132 0.054 Uiso 1 1 d . . . H5B H 0.8757 0.5739 0.0126 0.055 Uiso 1 1 d . . . H6B H 0.0952 0.0947 0.2209 0.041 Uiso 1 1 d . . . H7B H 0.8741 0.1763 -0.0022 0.046 Uiso 1 1 d . . . Mn1 Mn 0.5000 0.5000 0.0000 0.01622(8) Uani 1 2 d S . . N1 N 0.23651(17) 0.30543(13) 0.48772(10) 0.0287(2) Uani 1 1 d . . . H1A H 0.2710 0.2591 0.5490 0.034 Uiso 1 1 d R . . H1B H 0.1852 0.2584 0.4172 0.034 Uiso 1 1 d R . . N2 N 0.32381(16) 0.53083(12) 0.62595(10) 0.0239(2) Uani 1 1 d . . . H2 H 0.3517 0.4778 0.6873 0.029 Uiso 1 1 calc R . . O1 O 0.62383(12) 0.71762(9) -0.08647(8) 0.02147(18) Uani 1 1 d . . . O2 O 0.77297(13) 0.97715(10) -0.08775(8) 0.02307(19) Uani 1 1 d . . . O3 O 0.56678(14) 0.63885(10) 0.18640(8) 0.0252(2) Uani 1 1 d . . . O4 O 0.71805(14) 0.86649(10) 0.30251(8) 0.0265(2) Uani 1 1 d . . . O5 O 0.77966(13) 0.49344(11) 0.03370(13) 0.0415(3) Uani 1 1 d . . . O6 O 0.03134(13) 0.13157(10) 0.25832(8) 0.0252(2) Uani 1 1 d . . . O7 O 0.92013(13) 0.26065(10) 0.04802(9) 0.0257(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 0.0165(5) 0.0156(5) 0.0196(5) 0.0032(4) -0.0009(4) 0.0070(4) C2 0.0222(6) 0.0156(5) 0.0222(5) 0.0029(4) 0.0029(4) 0.0087(5) C3 0.0213(6) 0.0168(5) 0.0199(5) 0.0024(4) 0.0043(4) 0.0070(5) C4 0.0455(9) 0.0437(9) 0.0369(8) 0.0207(7) 0.0074(6) 0.0237(7) C5 0.0204(6) 0.0245(6) 0.0210(5) 0.0039(5) 0.0035(4) 0.0074(5) C6 0.0277(7) 0.0307(7) 0.0188(5) 0.0061(5) 0.0019(5) 0.0101(5) C7 0.0253(6) 0.0326(7) 0.0271(6) 0.0124(5) 0.0075(5) 0.0136(6) C8 0.0399(8) 0.0262(7) 0.0316(7) 0.0047(5) 0.0068(6) 0.0172(6) C9 0.0407(8) 0.0269(7) 0.0246(6) -0.0006(5) 0.0006(5) 0.0136(6) Mn1 0.01582(13) 0.01150(13) 0.02070(13) 0.00159(9) 0.00053(9) 0.00436(9) N1 0.0400(7) 0.0234(5) 0.0218(5) 0.0016(4) -0.0027(4) 0.0113(5) N2 0.0312(6) 0.0238(5) 0.0185(5) 0.0045(4) 0.0005(4) 0.0121(5) O1 0.0266(5) 0.0138(4) 0.0217(4) 0.0015(3) 0.0032(3) 0.0046(3) O2 0.0287(5) 0.0145(4) 0.0248(4) 0.0054(3) 0.0069(3) 0.0057(4) O3 0.0390(5) 0.0143(4) 0.0207(4) 0.0031(3) 0.0010(4) 0.0078(4) O4 0.0353(5) 0.0186(4) 0.0213(4) 0.0009(3) -0.0014(4) 0.0053(4) O5 0.0181(5) 0.0204(5) 0.0891(9) 0.0162(5) 0.0078(5) 0.0087(4) O6 0.0269(5) 0.0220(4) 0.0246(4) -0.0004(3) 0.0046(3) 0.0067(4) O7 0.0247(5) 0.0150(4) 0.0365(5) 0.0028(4) -0.0032(4) 0.0069(4) _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 1.2553(14) . ? C1 O1 1.2621(14) . ? C1 C2 1.5274(16) . ? C2 C3 1.5248(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O4 1.2491(14) . ? C3 O3 1.2691(14) . ? C4 C7 1.5016(18) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N1 1.3286(17) . ? C5 N2 1.3504(16) . ? C5 C6 1.4136(17) . ? C6 C7 1.365(2) . ? C6 H6 0.8892 . ? C7 C8 1.418(2) . ? C8 C9 1.3512(19) . ? C8 H8 0.9500 . ? C9 N2 1.3637(17) . ? C9 H9 0.9500 . ? Mn1 O1 2.1172(8) 2_665 ? Mn1 O1 2.1172(8) . ? Mn1 O5 2.1806(10) . ? Mn1 O5 2.1806(10) 2_665 ? Mn1 O3 2.1843(8) . ? Mn1 O3 2.1843(8) 2_665 ? N1 H1A 0.8625 . ? N1 H1B 0.8305 . ? N2 H2 0.8800 . ? O5 H5A 0.8398 . ? O5 H5B 0.8701 . ? O6 H6A 0.8029 . ? O6 H6B 0.7926 . ? O7 H7A 0.7969 . ? O7 H7B 0.8536 . ? 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 123.07(10) . . ? O2 C1 C2 118.26(10) . . ? O1 C1 C2 118.64(10) . . ? C3 C2 C1 114.50(9) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? O4 C3 O3 123.88(11) . . ? O4 C3 C2 117.79(10) . . ? O3 C3 C2 118.31(10) . . ? C7 C4 H4A 109.5 . . ? C7 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C7 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 N2 118.80(11) . . ? N1 C5 C6 123.23(12) . . ? N2 C5 C6 117.96(11) . . ? C7 C6 C5 120.95(12) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.4 . . ? C6 C7 C8 118.72(12) . . ? C6 C7 C4 121.39(13) . . ? C8 C7 C4 119.89(13) . . ? C9 C8 C7 119.45(13) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 N2 120.88(12) . . ? C8 C9 H9 119.6 . . ? N2 C9 H9 119.6 . . ? O1 Mn1 O1 180.0 2_665 . ? O1 Mn1 O5 91.10(3) 2_665 . ? O1 Mn1 O5 88.90(3) . . ? O1 Mn1 O5 88.90(3) 2_665 2_665 ? O1 Mn1 O5 91.10(3) . 2_665 ? O5 Mn1 O5 180.0 . 2_665 ? O1 Mn1 O3 93.20(3) 2_665 . ? O1 Mn1 O3 86.80(3) . . ? O5 Mn1 O3 84.06(4) . . ? O5 Mn1 O3 95.94(4) 2_665 . ? O1 Mn1 O3 86.80(3) 2_665 2_665 ? O1 Mn1 O3 93.20(3) . 2_665 ? O5 Mn1 O3 95.94(4) . 2_665 ? O5 Mn1 O3 84.06(4) 2_665 2_665 ? O3 Mn1 O3 180.0 . 2_665 ? C5 N1 H1A 119.4 . . ? C5 N1 H1B 117.8 . . ? H1A N1 H1B 122.7 . . ? C5 N2 C9 122.02(11) . . ? C5 N2 H2 119.0 . . ? C9 N2 H2 119.0 . . ? C1 O1 Mn1 128.62(7) . . ? C3 O3 Mn1 125.64(7) . . ? Mn1 O5 H5A 129.0 . . ? Mn1 O5 H5B 118.0 . . ? H5A O5 H5B 109.5 . . ? H6A O6 H6B 101.2 . . ? H7A O7 H7B 105.0 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.64 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.573 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.054