# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ydkr _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[[Mn(dpaqOMe)(NO)]ClO4' _chemical_formula_moiety 'C24 H22 Mn N6 O3' _chemical_formula_sum 'C24 H22 Cl Mn N6 O7' _chemical_melting_point ? _exptl_crystal_description platelet _exptl_crystal_colour brown _diffrn_ambient_temperature 113(2) _chemical_formula_weight 596.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn -0.5299 2.8052 '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_int_tables_number 2 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6256(5) _cell_length_b 11.7224(9) _cell_length_c 13.1577(10) _cell_angle_alpha 71.050(4) _cell_angle_beta 87.566(4) _cell_angle_gamma 80.591(3) _cell_volume 1241.30(15) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8216 _cell_measurement_theta_min 3.55 _cell_measurement_theta_max 67.715 _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.597 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 5.829 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2827 _exptl_absorpt_correction_T_max 0.5933 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector IP _diffrn_measurement_device_type 'Rigaku R-AXISIP' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16650 _diffrn_reflns_av_R_equivalents 0.1127 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 49.99 _reflns_number_total 2542 _reflns_number_gt 1715 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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. The disordered perchlorate ion was modeled with SADI restraints in order to yield similar O...O distances. The Cl-O distances were restrained to 1.42 (2) A with DFIX restraints. The perchlorae ion were treated as disordered over two sites (50:50). Additonally, the vibration of the oxygen atoms was made somewhat isotropic by an ISOR restraint. ; _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^)+(0.1290P)^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 SHELXL _refine_ls_extinction_coef 0.0002(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2542 _refine_ls_number_parameters 391 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.0969 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.2268 _refine_ls_wR_factor_gt 0.1902 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.133 _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 -0.04154(13) 0.29558(11) 0.21794(10) 0.0585(7) Uani 1 1 d . . . N1 N 0.0111(7) 0.2350(6) 0.0931(6) 0.0582(19) Uani 1 1 d . . . C1 C -0.0275(9) 0.2920(7) -0.0097(8) 0.061(2) Uani 1 1 d . . . H1 H -0.0929 0.3695 -0.0282 0.073 Uiso 1 1 calc R . . C2 C 0.0228(10) 0.2441(8) -0.0926(8) 0.068(3) Uani 1 1 d . . . H2 H -0.0118 0.2875 -0.1644 0.081 Uiso 1 1 calc R . . C3 C 0.1222(10) 0.1345(9) -0.0698(8) 0.072(3) Uani 1 1 d . . . H3 H 0.1609 0.1029 -0.1255 0.086 Uiso 1 1 calc R . . C4 C 0.2683(10) -0.0448(8) 0.0766(8) 0.065(2) Uani 1 1 d . . . C5 C 0.3020(10) -0.0990(8) 0.1821(8) 0.064(2) Uani 1 1 d . . . H5 H 0.3681 -0.1762 0.2047 0.077 Uiso 1 1 calc R . . C6 C 0.2427(10) -0.0454(8) 0.2591(7) 0.066(2) Uani 1 1 d . . . H6 H 0.2686 -0.0863 0.3328 0.079 Uiso 1 1 calc R . . C7 C 0.1461(9) 0.0673(8) 0.2285(7) 0.059(2) Uani 1 1 d . . . C8 C 0.1655(9) 0.0697(7) 0.0390(8) 0.060(2) Uani 1 1 d . . . C9 C 0.1101(9) 0.1237(8) 0.1174(8) 0.061(2) Uani 1 1 d . . . N2 N -0.2327(7) 0.2142(6) 0.2724(6) 0.0582(19) Uani 1 1 d . . . C10 C -0.3013(9) 0.2397(7) 0.3585(7) 0.056(2) Uani 1 1 d . . . C11 C -0.4319(10) 0.1896(8) 0.4057(7) 0.064(2) Uani 1 1 d . . . H11 H -0.4814 0.2101 0.4646 0.076 Uiso 1 1 calc R . . C12 C -0.4884(10) 0.1095(8) 0.3654(8) 0.071(3) Uani 1 1 d . . . H12 H -0.5772 0.0738 0.3974 0.085 Uiso 1 1 calc R . . C13 C -0.4181(11) 0.0806(8) 0.2795(9) 0.074(3) Uani 1 1 d . . . H13 H -0.4565 0.0253 0.2514 0.089 Uiso 1 1 calc R . . C14 C -0.2902(10) 0.1344(8) 0.2355(7) 0.066(2) Uani 1 1 d . . . H14 H -0.2398 0.1146 0.1765 0.079 Uiso 1 1 calc R . . N3 N 0.1591(7) 0.3713(5) 0.2150(5) 0.0553(18) Uani 1 1 d . . . C15 C 0.1567(9) 0.4275(7) 0.2913(7) 0.056(2) Uani 1 1 d . . . C16 C 0.2820(10) 0.4846(7) 0.3007(6) 0.059(2) Uani 1 1 d . . . H16 H 0.2815 0.5215 0.3553 0.070 Uiso 1 1 calc R . . C17 C 0.4075(10) 0.4880(7) 0.2311(8) 0.063(2) Uani 1 1 d . . . H17 H 0.4910 0.5298 0.2358 0.076 Uiso 1 1 calc R . . C18 C 0.4099(9) 0.4306(7) 0.1553(7) 0.065(3) Uani 1 1 d . . . H18 H 0.4961 0.4305 0.1079 0.078 Uiso 1 1 calc R . . C19 C 0.2851(10) 0.3729(7) 0.1490(6) 0.059(2) Uani 1 1 d . . . H19 H 0.2874 0.3327 0.0966 0.071 Uiso 1 1 calc R . . N4 N 0.0823(7) 0.1408(7) 0.2928(5) 0.0568(19) Uani 1 1 d . . . C20 C 0.1061(9) 0.1060(8) 0.3977(8) 0.057(2) Uani 1 1 d . . . O1 O 0.1765(6) 0.0085(5) 0.4600(4) 0.0628(16) Uani 1 1 d . . . N5 N -0.0559(7) 0.3156(5) 0.3646(5) 0.0502(17) Uani 1 1 d . . . C21 C -0.2257(9) 0.3271(7) 0.3932(7) 0.066(2) Uani 1 1 d . . . H21 H -0.2786 0.4117 0.3572 0.079 Uiso 1 1 calc R . . H21A H -0.2366 0.3093 0.4718 0.079 Uiso 1 1 calc R . . C22 C 0.0142(9) 0.4250(7) 0.3599(7) 0.061(2) Uani 1 1 d . . . H22 H 0.0434 0.4209 0.4332 0.073 Uiso 1 1 calc R . . H22A H -0.0627 0.5001 0.3290 0.073 Uiso 1 1 calc R . . C23 C 0.0340(10) 0.2031(7) 0.4456(7) 0.063(2) Uani 1 1 d . . . H23 H 0.1185 0.2279 0.4784 0.075 Uiso 1 1 calc R . . H23A H -0.0382 0.1678 0.5036 0.021(16) Uiso 1 1 calc R . . N6 N -0.1558(8) 0.4327(7) 0.1450(6) 0.056(2) Uani 1 1 d . . . O2 O -0.2245(8) 0.5100(6) 0.0998(5) 0.0698(19) Uani 1 1 d . . . O3 O 0.3274(7) -0.0876(5) -0.0061(5) 0.0811(19) Uani 1 1 d . . . C24 C 0.4434(12) -0.1993(8) 0.0263(8) 0.099(3) Uani 1 1 d . . . H24 H 0.5298 -0.1870 0.0656 0.148 Uiso 1 1 calc R . . H24A H 0.4845 -0.2187 -0.0377 0.148 Uiso 1 1 calc R . . H24B H 0.3935 -0.2668 0.0727 0.148 Uiso 1 1 calc R . . Cl1 Cl 0.3469(3) 0.3156(2) 0.6392(2) 0.0825(9) Uani 1 1 d D . . O5 O 0.3338(12) 0.1955(6) 0.6517(8) 0.123(4) Uani 0.80 1 d PDU A 1 O6 O 0.3168(11) 0.3449(8) 0.7367(6) 0.065(3) Uani 0.80 1 d PDU A 1 O7 O 0.2480(9) 0.4012(7) 0.5549(6) 0.079(3) Uani 0.80 1 d PDU A 1 O8 O 0.5123(8) 0.3346(8) 0.6078(6) 0.106(3) Uani 0.80 1 d PDU A 1 O9 O 0.188(3) 0.275(3) 0.658(2) 0.120(12) Uani 0.20 1 d PDU A 2 O10 O 0.452(3) 0.220(2) 0.629(2) 0.082(10) Uani 0.20 1 d PDU A 2 O11 O 0.328(4) 0.419(2) 0.546(2) 0.13(2) Uani 0.20 1 d PDU A 2 O12 O 0.375(3) 0.349(3) 0.730(2) 0.09(2) Uani 0.20 1 d PDU A 2 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 0.0416(10) 0.0543(11) 0.0754(11) -0.0154(8) -0.0092(7) -0.0048(7) N1 0.044(4) 0.047(5) 0.072(5) -0.003(4) -0.015(4) -0.006(4) C1 0.049(6) 0.038(5) 0.092(7) -0.014(6) -0.009(5) -0.009(4) C2 0.062(6) 0.055(6) 0.078(6) -0.011(5) -0.019(5) -0.004(5) C3 0.071(7) 0.069(7) 0.081(7) -0.036(6) -0.012(5) -0.003(5) C4 0.067(7) 0.062(6) 0.077(7) -0.035(6) -0.005(5) -0.014(5) C5 0.051(6) 0.053(6) 0.083(7) -0.012(5) -0.012(5) -0.008(4) C6 0.061(6) 0.057(6) 0.083(6) -0.029(5) -0.018(5) 0.001(5) C7 0.035(5) 0.058(6) 0.077(6) -0.009(5) -0.015(5) -0.011(5) C8 0.044(5) 0.042(6) 0.093(7) -0.025(6) -0.012(5) 0.002(4) C9 0.040(5) 0.044(6) 0.094(7) -0.016(6) -0.014(5) -0.002(4) N2 0.049(4) 0.046(5) 0.075(5) -0.013(4) -0.014(4) -0.003(4) C10 0.042(6) 0.062(6) 0.060(5) -0.015(5) -0.005(5) -0.002(5) C11 0.047(6) 0.056(6) 0.071(6) -0.002(5) 0.000(5) -0.001(5) C12 0.053(6) 0.052(6) 0.091(7) 0.002(6) -0.025(6) -0.007(5) C13 0.054(7) 0.058(6) 0.099(8) -0.014(6) -0.017(6) -0.002(5) C14 0.058(6) 0.052(6) 0.082(6) -0.013(5) -0.013(5) -0.007(5) N3 0.050(5) 0.039(4) 0.067(4) -0.006(4) -0.019(4) 0.001(3) C15 0.044(6) 0.049(5) 0.074(6) -0.020(5) -0.011(5) -0.002(4) C16 0.039(5) 0.062(6) 0.069(6) -0.017(5) -0.012(5) 0.002(5) C17 0.046(6) 0.056(6) 0.091(7) -0.025(6) -0.029(5) -0.004(4) C18 0.032(5) 0.059(6) 0.086(7) 0.004(5) -0.017(5) -0.008(4) C19 0.043(6) 0.061(6) 0.058(5) -0.008(5) -0.014(5) 0.017(5) N4 0.039(4) 0.074(5) 0.056(4) -0.012(4) -0.009(3) -0.022(4) C20 0.037(5) 0.046(6) 0.082(7) -0.011(5) -0.016(5) -0.007(4) O1 0.047(4) 0.062(4) 0.067(4) -0.005(3) -0.005(3) -0.004(3) N5 0.028(4) 0.045(4) 0.076(5) -0.019(4) -0.007(3) 0.000(3) C21 0.057(6) 0.066(6) 0.074(6) -0.023(5) -0.008(5) -0.002(5) C22 0.043(5) 0.063(6) 0.076(6) -0.021(5) 0.001(4) -0.013(4) C23 0.054(6) 0.057(6) 0.070(6) -0.008(5) -0.005(5) -0.013(5) N6 0.038(5) 0.054(5) 0.085(6) -0.034(5) -0.005(4) -0.006(4) O2 0.067(5) 0.076(5) 0.064(4) -0.014(4) -0.008(3) -0.019(4) O3 0.076(5) 0.072(5) 0.092(5) -0.029(4) -0.018(4) 0.008(4) C24 0.111(9) 0.079(8) 0.109(8) -0.041(7) -0.017(7) 0.008(7) Cl1 0.088(2) 0.0713(19) 0.0872(19) -0.0319(16) -0.0235(16) 0.0102(16) O5 0.129(8) 0.059(6) 0.192(10) -0.048(6) -0.022(7) -0.026(6) O6 0.047(5) 0.087(7) 0.070(6) -0.034(5) -0.005(4) -0.014(4) O7 0.060(6) 0.094(6) 0.065(5) -0.009(4) -0.021(4) 0.012(5) O8 0.058(5) 0.158(8) 0.106(6) -0.048(6) 0.006(5) -0.018(5) O9 0.16(2) 0.116(19) 0.113(19) -0.085(17) 0.003(16) -0.011(17) O10 0.110(19) 0.053(16) 0.091(17) -0.041(14) 0.045(15) -0.006(15) O11 0.15(3) 0.14(3) 0.12(3) -0.059(19) 0.001(18) 0.003(19) O12 0.10(3) 0.09(2) 0.10(2) -0.049(18) -0.002(16) -0.010(17) _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 N6 1.742(8) . ? Mn1 N4 1.923(7) . ? Mn1 N1 2.000(7) . ? Mn1 N5 2.015(6) . ? Mn1 N2 2.028(7) . ? Mn1 N3 2.063(6) . ? N1 C1 1.329(10) . ? N1 C9 1.387(10) . ? C1 C2 1.404(11) . ? C1 H1 0.9500 . ? C2 C3 1.374(11) . ? C2 H2 0.9500 . ? C3 C8 1.418(11) . ? C3 H3 0.9500 . ? C4 C5 1.347(11) . ? C4 O3 1.386(10) . ? C4 C8 1.432(11) . ? C5 C6 1.396(11) . ? C5 H5 0.9500 . ? C6 C7 1.387(11) . ? C6 H6 0.9500 . ? C7 C9 1.419(12) . ? C7 N4 1.429(11) . ? C8 C9 1.406(11) . ? N2 C14 1.349(10) . ? N2 C10 1.352(9) . ? C10 C11 1.385(10) . ? C10 C21 1.493(11) . ? C11 C12 1.377(11) . ? C11 H11 0.9500 . ? C12 C13 1.372(12) . ? C12 H12 0.9500 . ? C13 C14 1.374(11) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N3 C19 1.361(9) . ? N3 C15 1.366(9) . ? C15 C16 1.390(10) . ? C15 C22 1.492(10) . ? C16 C17 1.386(10) . ? C16 H16 0.9500 . ? C17 C18 1.370(11) . ? C17 H17 0.9500 . ? C18 C19 1.380(10) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? N4 C20 1.320(10) . ? C20 O1 1.247(9) . ? C20 C23 1.510(11) . ? N5 C22 1.488(9) . ? N5 C21 1.493(9) . ? N5 C23 1.516(9) . ? C21 H21 0.9900 . ? C21 H21A 0.9900 . ? C22 H22 0.9900 . ? C22 H22A 0.9900 . ? C23 H23 0.9900 . ? C23 H23A 0.9900 . ? N6 O2 1.015(7) . ? O3 C24 1.463(9) . ? C24 H24 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? Cl1 O10 1.359(16) . ? Cl1 O5 1.386(7) . ? Cl1 O11 1.406(18) . ? Cl1 O12 1.412(18) . ? Cl1 O7 1.429(6) . ? Cl1 O6 1.436(7) . ? Cl1 O8 1.500(7) . ? Cl1 O9 1.507(18) . ? 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 N6 Mn1 N4 177.0(3) . . ? N6 Mn1 N1 96.0(3) . . ? N4 Mn1 N1 81.3(3) . . ? N6 Mn1 N5 99.3(3) . . ? N4 Mn1 N5 83.4(3) . . ? N1 Mn1 N5 164.7(3) . . ? N6 Mn1 N2 92.7(3) . . ? N4 Mn1 N2 86.6(2) . . ? N1 Mn1 N2 99.3(3) . . ? N5 Mn1 N2 81.0(3) . . ? N6 Mn1 N3 94.7(3) . . ? N4 Mn1 N3 86.8(2) . . ? N1 Mn1 N3 97.0(3) . . ? N5 Mn1 N3 80.8(3) . . ? N2 Mn1 N3 161.3(3) . . ? C1 N1 C9 117.0(8) . . ? C1 N1 Mn1 128.0(6) . . ? C9 N1 Mn1 114.8(6) . . ? N1 C1 C2 123.6(8) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 119.9(8) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C8 118.4(8) . . ? C2 C3 H3 120.8 . . ? C8 C3 H3 120.8 . . ? C5 C4 O3 126.3(8) . . ? C5 C4 C8 121.0(9) . . ? O3 C4 C8 112.7(8) . . ? C4 C5 C6 122.0(8) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C7 C6 C5 120.3(8) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C9 117.4(9) . . ? C6 C7 N4 129.1(8) . . ? C9 C7 N4 113.4(8) . . ? C9 C8 C3 118.2(7) . . ? C9 C8 C4 116.1(8) . . ? C3 C8 C4 125.7(9) . . ? N1 C9 C8 122.8(8) . . ? N1 C9 C7 114.2(9) . . ? C8 C9 C7 123.1(8) . . ? C14 N2 C10 118.6(8) . . ? C14 N2 Mn1 126.9(7) . . ? C10 N2 Mn1 114.4(6) . . ? N2 C10 C11 121.2(8) . . ? N2 C10 C21 113.7(7) . . ? C11 C10 C21 125.1(8) . . ? C12 C11 C10 118.7(9) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C13 C12 C11 120.8(9) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 117.6(9) . . ? C12 C13 H13 121.2 . . ? C14 C13 H13 121.2 . . ? N2 C14 C13 123.1(9) . . ? N2 C14 H14 118.5 . . ? C13 C14 H14 118.5 . . ? C19 N3 C15 118.9(7) . . ? C19 N3 Mn1 129.3(6) . . ? C15 N3 Mn1 111.8(6) . . ? N3 C15 C16 119.9(8) . . ? N3 C15 C22 116.6(7) . . ? C16 C15 C22 123.5(8) . . ? C17 C16 C15 120.4(8) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 119.3(8) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 119.0(9) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? N3 C19 C18 122.4(8) . . ? N3 C19 H19 118.8 . . ? C18 C19 H19 118.8 . . ? C20 N4 C7 122.7(7) . . ? C20 N4 Mn1 121.2(7) . . ? C7 N4 Mn1 116.1(5) . . ? O1 C20 N4 130.3(9) . . ? O1 C20 C23 117.5(8) . . ? N4 C20 C23 112.2(8) . . ? C22 N5 C21 112.8(6) . . ? C22 N5 C23 109.7(6) . . ? C21 N5 C23 109.3(6) . . ? C22 N5 Mn1 108.6(5) . . ? C21 N5 Mn1 106.8(4) . . ? C23 N5 Mn1 109.5(5) . . ? N5 C21 C10 109.6(6) . . ? N5 C21 H21 109.7 . . ? C10 C21 H21 109.7 . . ? N5 C21 H21A 109.7 . . ? C10 C21 H21A 109.7 . . ? H21 C21 H21A 108.2 . . ? N5 C22 C15 108.2(6) . . ? N5 C22 H22 110.1 . . ? C15 C22 H22 110.1 . . ? N5 C22 H22A 110.1 . . ? C15 C22 H22A 110.1 . . ? H22 C22 H22A 108.4 . . ? C20 C23 N5 113.6(7) . . ? C20 C23 H23 108.9 . . ? N5 C23 H23 108.9 . . ? C20 C23 H23A 108.9 . . ? N5 C23 H23A 108.9 . . ? H23 C23 H23A 107.7 . . ? O2 N6 Mn1 176.7(8) . . ? C4 O3 C24 115.3(7) . . ? O3 C24 H24 109.5 . . ? O3 C24 H24A 109.5 . . ? H24 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? H24 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O10 Cl1 O5 47.6(11) . . ? O10 Cl1 O11 114.1(11) . . ? O5 Cl1 O11 129.7(17) . . ? O10 Cl1 O12 113.7(11) . . ? O5 Cl1 O12 119.6(17) . . ? O11 Cl1 O12 110.6(11) . . ? O10 Cl1 O7 125.1(13) . . ? O5 Cl1 O7 112.6(4) . . ? O11 Cl1 O7 30.6(14) . . ? O12 Cl1 O7 118.5(17) . . ? O10 Cl1 O6 125.3(14) . . ? O5 Cl1 O6 112.6(5) . . ? O11 Cl1 O6 113.3(17) . . ? O12 Cl1 O6 20.6(13) . . ? O7 Cl1 O6 109.6(4) . . ? O10 Cl1 O8 60.9(12) . . ? O5 Cl1 O8 108.6(5) . . ? O11 Cl1 O8 76.4(14) . . ? O12 Cl1 O8 86.3(13) . . ? O7 Cl1 O8 106.3(4) . . ? O6 Cl1 O8 106.8(4) . . ? O10 Cl1 O9 107.5(10) . . ? O5 Cl1 O9 60.2(10) . . ? O11 Cl1 O9 105.3(10) . . ? O12 Cl1 O9 104.8(10) . . ? O7 Cl1 O9 74.7(13) . . ? O6 Cl1 O9 84.6(11) . . ? O8 Cl1 O9 167.0(10) . . ? 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 N6 Mn1 N1 C1 3.3(7) . . . . ? N4 Mn1 N1 C1 -177.9(6) . . . . ? N5 Mn1 N1 C1 -172.9(8) . . . . ? N2 Mn1 N1 C1 97.0(6) . . . . ? N3 Mn1 N1 C1 -92.2(6) . . . . ? N6 Mn1 N1 C9 178.0(5) . . . . ? N4 Mn1 N1 C9 -3.2(5) . . . . ? N5 Mn1 N1 C9 1.8(12) . . . . ? N2 Mn1 N1 C9 -88.3(5) . . . . ? N3 Mn1 N1 C9 82.5(5) . . . . ? C9 N1 C1 C2 1.7(11) . . . . ? Mn1 N1 C1 C2 176.3(6) . . . . ? N1 C1 C2 C3 -2.4(12) . . . . ? C1 C2 C3 C8 2.9(12) . . . . ? O3 C4 C5 C6 176.6(7) . . . . ? C8 C4 C5 C6 -1.8(13) . . . . ? C4 C5 C6 C7 -0.2(13) . . . . ? C5 C6 C7 C9 0.5(12) . . . . ? C5 C6 C7 N4 -175.5(8) . . . . ? C2 C3 C8 C9 -2.8(12) . . . . ? C2 C3 C8 C4 -179.6(8) . . . . ? C5 C4 C8 C9 3.2(12) . . . . ? O3 C4 C8 C9 -175.4(7) . . . . ? C5 C4 C8 C3 -179.9(8) . . . . ? O3 C4 C8 C3 1.5(12) . . . . ? C1 N1 C9 C8 -1.7(11) . . . . ? Mn1 N1 C9 C8 -177.0(6) . . . . ? C1 N1 C9 C7 -179.6(6) . . . . ? Mn1 N1 C9 C7 5.0(8) . . . . ? C3 C8 C9 N1 2.2(12) . . . . ? C4 C8 C9 N1 179.3(7) . . . . ? C3 C8 C9 C7 -180.0(7) . . . . ? C4 C8 C9 C7 -2.9(12) . . . . ? C6 C7 C9 N1 179.0(7) . . . . ? N4 C7 C9 N1 -4.3(10) . . . . ? C6 C7 C9 C8 1.1(12) . . . . ? N4 C7 C9 C8 177.7(7) . . . . ? N6 Mn1 N2 C14 101.8(6) . . . . ? N4 Mn1 N2 C14 -75.4(6) . . . . ? N1 Mn1 N2 C14 5.2(6) . . . . ? N5 Mn1 N2 C14 -159.3(6) . . . . ? N3 Mn1 N2 C14 -144.9(8) . . . . ? N6 Mn1 N2 C10 -82.1(5) . . . . ? N4 Mn1 N2 C10 100.7(5) . . . . ? N1 Mn1 N2 C10 -178.7(5) . . . . ? N5 Mn1 N2 C10 16.8(5) . . . . ? N3 Mn1 N2 C10 31.2(10) . . . . ? C14 N2 C10 C11 -2.7(11) . . . . ? Mn1 N2 C10 C11 -179.2(6) . . . . ? C14 N2 C10 C21 178.9(6) . . . . ? Mn1 N2 C10 C21 2.4(8) . . . . ? N2 C10 C11 C12 2.1(11) . . . . ? C21 C10 C11 C12 -179.7(7) . . . . ? C10 C11 C12 C13 -0.7(12) . . . . ? C11 C12 C13 C14 -0.1(12) . . . . ? C10 N2 C14 C13 2.0(11) . . . . ? Mn1 N2 C14 C13 177.9(6) . . . . ? C12 C13 C14 N2 -0.6(12) . . . . ? N6 Mn1 N3 C19 -98.5(6) . . . . ? N4 Mn1 N3 C19 79.0(6) . . . . ? N1 Mn1 N3 C19 -1.8(6) . . . . ? N5 Mn1 N3 C19 162.9(6) . . . . ? N2 Mn1 N3 C19 148.5(8) . . . . ? N6 Mn1 N3 C15 80.8(5) . . . . ? N4 Mn1 N3 C15 -101.8(5) . . . . ? N1 Mn1 N3 C15 177.4(5) . . . . ? N5 Mn1 N3 C15 -17.9(5) . . . . ? N2 Mn1 N3 C15 -32.3(10) . . . . ? C19 N3 C15 C16 -0.2(10) . . . . ? Mn1 N3 C15 C16 -179.5(5) . . . . ? C19 N3 C15 C22 178.8(6) . . . . ? Mn1 N3 C15 C22 -0.5(8) . . . . ? N3 C15 C16 C17 1.9(11) . . . . ? C22 C15 C16 C17 -177.1(7) . . . . ? C15 C16 C17 C18 -2.5(11) . . . . ? C16 C17 C18 C19 1.4(11) . . . . ? C15 N3 C19 C18 -0.9(10) . . . . ? Mn1 N3 C19 C18 178.3(5) . . . . ? C17 C18 C19 N3 0.3(11) . . . . ? C6 C7 N4 C20 -2.0(13) . . . . ? C9 C7 N4 C20 -178.1(6) . . . . ? C6 C7 N4 Mn1 177.8(7) . . . . ? C9 C7 N4 Mn1 1.7(9) . . . . ? N6 Mn1 N4 C20 -155(6) . . . . ? N1 Mn1 N4 C20 -179.4(6) . . . . ? N5 Mn1 N4 C20 2.0(6) . . . . ? N2 Mn1 N4 C20 -79.4(6) . . . . ? N3 Mn1 N4 C20 83.1(6) . . . . ? N6 Mn1 N4 C7 25(6) . . . . ? N1 Mn1 N4 C7 0.8(5) . . . . ? N5 Mn1 N4 C7 -177.9(5) . . . . ? N2 Mn1 N4 C7 100.8(6) . . . . ? N3 Mn1 N4 C7 -96.8(5) . . . . ? C7 N4 C20 O1 -3.4(13) . . . . ? Mn1 N4 C20 O1 176.7(6) . . . . ? C7 N4 C20 C23 176.7(6) . . . . ? Mn1 N4 C20 C23 -3.2(9) . . . . ? N6 Mn1 N5 C22 -61.5(5) . . . . ? N4 Mn1 N5 C22 119.6(5) . . . . ? N1 Mn1 N5 C22 114.6(9) . . . . ? N2 Mn1 N5 C22 -152.8(5) . . . . ? N3 Mn1 N5 C22 31.8(4) . . . . ? N6 Mn1 N5 C21 60.4(5) . . . . ? N4 Mn1 N5 C21 -118.4(5) . . . . ? N1 Mn1 N5 C21 -123.4(9) . . . . ? N2 Mn1 N5 C21 -30.9(4) . . . . ? N3 Mn1 N5 C21 153.7(5) . . . . ? N6 Mn1 N5 C23 178.7(5) . . . . ? N4 Mn1 N5 C23 -0.1(4) . . . . ? N1 Mn1 N5 C23 -5.1(12) . . . . ? N2 Mn1 N5 C23 87.4(5) . . . . ? N3 Mn1 N5 C23 -88.0(5) . . . . ? C22 N5 C21 C10 159.6(6) . . . . ? C23 N5 C21 C10 -78.0(7) . . . . ? Mn1 N5 C21 C10 40.4(7) . . . . ? N2 C10 C21 N5 -28.7(9) . . . . ? C11 C10 C21 N5 153.0(7) . . . . ? C21 N5 C22 C15 -157.9(6) . . . . ? C23 N5 C22 C15 80.0(8) . . . . ? Mn1 N5 C22 C15 -39.7(7) . . . . ? N3 C15 C22 N5 26.5(9) . . . . ? C16 C15 C22 N5 -154.5(7) . . . . ? O1 C20 C23 N5 -177.1(6) . . . . ? N4 C20 C23 N5 2.8(10) . . . . ? C22 N5 C23 C20 -120.4(7) . . . . ? C21 N5 C23 C20 115.4(7) . . . . ? Mn1 N5 C23 C20 -1.4(8) . . . . ? N4 Mn1 N6 O2 10(19) . . . . ? N1 Mn1 N6 O2 34(15) . . . . ? N5 Mn1 N6 O2 -147(15) . . . . ? N2 Mn1 N6 O2 -66(15) . . . . ? N3 Mn1 N6 O2 132(15) . . . . ? C5 C4 O3 C24 -3.4(12) . . . . ? C8 C4 O3 C24 175.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 49.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.683 _refine_diff_density_min -0.715 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 947309' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ydkr _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[[Mn(dpaqCl)(NO)]ClO4' _chemical_formula_moiety 'C23 H19 Cl Mn N6 O2' _chemical_formula_sum 'C23 H20 Cl Mn N6 O6' _chemical_melting_point ? _exptl_crystal_description platelet _exptl_crystal_colour brown _diffrn_ambient_temperature 123(2) _chemical_formula_weight 566.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? 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 12.3007(5) _cell_length_b 13.3626(6) _cell_length_c 14.1948(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.070(2) _cell_angle_gamma 90.00 _cell_volume 2230.41(17) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 10765 _cell_measurement_theta_min 4.19 _cell_measurement_theta_max 67.96 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 6.417 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4461 _exptl_absorpt_correction_T_max 0.7397 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector IP _diffrn_measurement_device_type 'Rigaku R-AXISIP' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28188 _diffrn_reflns_av_R_equivalents 0.1213 _diffrn_reflns_av_sigmaI/netI 0.0800 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.19 _diffrn_reflns_theta_max 50.00 _reflns_number_total 2237 _reflns_number_gt 1266 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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. The disordered perchlorate ion was modeled with SADI restraints in order to yield similar O...O distances. The Cl-O distances were restrained to 1.42 (2) A with DFIX restraints. The O atoms of the perchlorae ion were treated as disordered over two sites (50:50). Additonally, the vibration of the oxygen atoms was made somewhat isotropic by an ISOR restraint. ; _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 SHELXL _refine_ls_extinction_coef 0.0021(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2237 _refine_ls_number_parameters 380 _refine_ls_number_restraints 95 _refine_ls_R_factor_all 0.1479 _refine_ls_R_factor_gt 0.1080 _refine_ls_wR_factor_ref 0.3130 _refine_ls_wR_factor_gt 0.2588 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.073 _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 0.34394(15) 0.21889(15) 0.38482(13) 0.0720(11) Uani 1 1 d . . . N1 N 0.4572(9) 0.1301(8) 0.3444(9) 0.080(3) Uani 1 1 d . . . C1 C 0.5420(13) 0.0748(11) 0.4025(10) 0.085(4) Uani 1 1 d . . . H1 H 0.5499 0.0719 0.4711 0.102 Uiso 1 1 calc R . . C2 C 0.6194(12) 0.0213(10) 0.3664(11) 0.084(4) Uani 1 1 d . . . H2 H 0.6795 -0.0158 0.4097 0.100 Uiso 1 1 calc R . . C3 C 0.6062(11) 0.0238(9) 0.2674(10) 0.077(4) Uani 1 1 d . . . H3 H 0.6584 -0.0112 0.2417 0.093 Uiso 1 1 calc R . . C4 C 0.4988(10) 0.0811(9) 0.0992(9) 0.067(3) Uani 1 1 d . . . H4 H 0.5480 0.0459 0.0701 0.081 Uiso 1 1 calc R . . C5 C 0.4118(11) 0.1352(8) 0.0438(9) 0.070(3) Uani 1 1 d . . . H5 H 0.4011 0.1400 -0.0251 0.084 Uiso 1 1 calc R . . C6 C 0.3349(9) 0.1859(9) 0.0851(9) 0.067(3) Uani 1 1 d . . . H6 H 0.2721 0.2213 0.0433 0.080 Uiso 1 1 calc R . . C7 C 0.3506(10) 0.1840(9) 0.1864(9) 0.064(3) Uani 1 1 d . . . C8 C 0.5158(11) 0.0776(9) 0.2030(10) 0.073(4) Uani 1 1 d . . . C9 C 0.4412(11) 0.1286(10) 0.2441(10) 0.069(3) Uani 1 1 d . . . N2 N 0.4296(9) 0.3563(7) 0.3829(6) 0.066(3) Uani 1 1 d . . . C10 C 0.3671(11) 0.4381(11) 0.3933(7) 0.070(4) Uani 1 1 d . . . C11 C 0.4072(11) 0.5339(10) 0.3845(8) 0.073(3) Uani 1 1 d . . . H11 H 0.3651 0.5908 0.3935 0.087 Uiso 1 1 calc R . . C12 C 0.5084(10) 0.5459(10) 0.3626(7) 0.067(3) Uani 1 1 d . . . H12 H 0.5354 0.6112 0.3553 0.080 Uiso 1 1 calc R . . C13 C 0.5711(11) 0.4625(11) 0.3511(8) 0.073(4) Uani 1 1 d . . . H13 H 0.6410 0.4693 0.3360 0.088 Uiso 1 1 calc R . . C14 C 0.5282(11) 0.3702(10) 0.3624(8) 0.072(4) Uani 1 1 d . . . H14 H 0.5706 0.3128 0.3553 0.086 Uiso 1 1 calc R . . N3 N 0.2092(8) 0.1209(8) 0.3871(6) 0.068(3) Uani 1 1 d . . . C15 C 0.1178(11) 0.1640(11) 0.4071(8) 0.071(4) Uani 1 1 d . . . C16 C 0.0263(11) 0.1077(11) 0.4051(8) 0.075(4) Uani 1 1 d . . . H16 H -0.0387 0.1398 0.4144 0.090 Uiso 1 1 calc R . . C17 C 0.0225(14) 0.0061(10) 0.3902(8) 0.080(4) Uani 1 1 d . . . H17 H -0.0425 -0.0319 0.3910 0.096 Uiso 1 1 calc R . . C18 C 0.1146(15) -0.0382(13) 0.3744(9) 0.094(4) Uani 1 1 d . . . H18 H 0.1154 -0.1085 0.3647 0.113 Uiso 1 1 calc R . . C19 C 0.2067(12) 0.0186(12) 0.3724(8) 0.078(4) Uani 1 1 d . . . H19 H 0.2705 -0.0132 0.3607 0.093 Uiso 1 1 calc R . . N4 N 0.2864(8) 0.2288(7) 0.2381(7) 0.057(3) Uani 1 1 d . . . C20 C 0.1972(13) 0.2907(9) 0.1954(13) 0.070(4) Uani 1 1 d . . . O1 O 0.1543(7) 0.3072(6) 0.1074(6) 0.080(3) Uani 1 1 d . . . N5 N 0.2086(7) 0.3211(7) 0.3762(6) 0.059(2) Uani 1 1 d . . . C21 C 0.2619(10) 0.4144(9) 0.4249(8) 0.073(3) Uani 1 1 d . . . H21 H 0.2834 0.4062 0.4973 0.088 Uiso 1 1 calc R . . H21A H 0.2070 0.4704 0.4064 0.088 Uiso 1 1 calc R . . C22 C 0.1342(10) 0.2738(9) 0.4306(8) 0.069(4) Uani 1 1 d . . . H22 H 0.0593 0.3076 0.4122 0.083 Uiso 1 1 calc R . . H22A H 0.1693 0.2825 0.5024 0.083 Uiso 1 1 calc R . . C23 C 0.1428(10) 0.3359(9) 0.2690(8) 0.075(4) Uani 1 1 d . . . H23 H 0.1327 0.4086 0.2560 0.090 Uiso 1 1 calc R . . H23A H 0.0662 0.3063 0.2574 0.090 Uiso 1 1 calc R . . N6 N 0.3973(13) 0.2081(13) 0.5042(9) 0.096(5) Uani 1 1 d . . . O2 O 0.4199(13) 0.2086(10) 0.5795(14) 0.162(6) Uani 1 1 d . . . Cl1 Cl 0.7622(18) 0.2552(13) 0.2310(14) 0.077(7) Uani 0.50 1 d PDU A 1 O3 O 0.882(2) 0.290(2) 0.264(2) 0.115(15) Uani 0.50 1 d PDU A 1 O4 O 0.726(2) 0.2417(19) 0.3163(17) 0.071(9) Uani 0.50 1 d PDU A 1 O5 O 0.697(2) 0.3290(18) 0.1668(17) 0.085(10) Uani 0.50 1 d PDU A 1 O6 O 0.761(3) 0.1625(16) 0.180(2) 0.080(11) Uani 0.50 1 d PDU A 1 Cl2 Cl 0.7753(16) 0.2533(12) 0.2527(15) 0.061(4) Uani 0.50 1 d PDU B 2 O7 O 0.785(2) 0.1632(14) 0.195(2) 0.065(9) Uani 0.50 1 d PDU B 2 O8 O 0.690(2) 0.3189(18) 0.1904(17) 0.074(8) Uani 0.50 1 d PDU B 2 O9 O 0.735(2) 0.2199(18) 0.3356(17) 0.072(9) Uani 0.50 1 d PDU B 2 O10 O 0.8822(15) 0.3007(17) 0.2883(17) 0.051(6) Uani 0.50 1 d PDU B 2 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 0.0703(17) 0.081(2) 0.0665(16) -0.0041(10) 0.0234(12) -0.0074(11) N1 0.090(9) 0.066(8) 0.086(8) 0.007(6) 0.029(7) -0.001(7) C1 0.091(11) 0.078(10) 0.083(10) 0.012(9) 0.023(9) -0.022(9) C2 0.073(10) 0.073(10) 0.102(12) 0.006(9) 0.021(9) -0.018(8) C3 0.093(11) 0.050(8) 0.096(11) -0.016(8) 0.039(9) -0.020(8) C4 0.079(9) 0.051(8) 0.077(9) -0.007(7) 0.031(7) -0.003(7) C5 0.083(10) 0.049(8) 0.077(8) 0.002(7) 0.020(8) 0.007(7) C6 0.050(8) 0.069(9) 0.075(10) -0.007(7) 0.008(7) 0.003(7) C7 0.052(8) 0.075(9) 0.062(9) 0.000(7) 0.012(7) -0.009(7) C8 0.063(9) 0.059(9) 0.088(10) 0.024(8) 0.008(8) 0.002(7) C9 0.057(9) 0.066(9) 0.085(10) -0.009(8) 0.022(8) -0.018(7) N2 0.066(7) 0.063(7) 0.076(7) -0.008(5) 0.031(5) -0.017(6) C10 0.074(9) 0.081(11) 0.052(7) 0.002(7) 0.013(6) 0.010(9) C11 0.078(10) 0.065(10) 0.073(8) -0.012(7) 0.019(7) -0.010(8) C12 0.062(8) 0.079(10) 0.058(7) 0.014(7) 0.015(6) -0.005(8) C13 0.082(9) 0.063(10) 0.071(8) -0.003(7) 0.016(7) 0.006(9) C14 0.065(9) 0.068(11) 0.083(9) 0.007(7) 0.024(7) 0.010(8) N3 0.062(7) 0.075(8) 0.065(6) 0.006(6) 0.016(5) 0.002(6) C15 0.061(9) 0.087(11) 0.066(8) -0.004(7) 0.021(7) -0.004(9) C16 0.062(9) 0.096(13) 0.066(8) -0.001(7) 0.019(6) -0.011(8) C17 0.113(13) 0.042(10) 0.079(9) 0.002(7) 0.018(8) -0.010(8) C18 0.109(13) 0.096(13) 0.070(9) 0.005(8) 0.014(9) 0.016(12) C19 0.076(10) 0.074(11) 0.078(9) -0.007(8) 0.014(7) 0.029(9) N4 0.057(6) 0.047(6) 0.077(7) -0.005(5) 0.032(6) -0.002(5) C20 0.083(10) 0.051(9) 0.096(11) -0.028(8) 0.057(9) -0.017(8) O1 0.084(7) 0.094(7) 0.062(6) 0.004(5) 0.019(5) 0.011(5) N5 0.052(6) 0.058(6) 0.067(6) -0.003(5) 0.021(5) 0.000(5) C21 0.081(9) 0.068(9) 0.075(8) -0.022(7) 0.029(7) -0.015(7) C22 0.059(8) 0.093(11) 0.059(8) -0.006(7) 0.024(6) -0.005(7) C23 0.081(9) 0.069(9) 0.067(8) 0.007(7) 0.012(7) -0.007(7) N6 0.093(9) 0.140(13) 0.064(8) -0.015(8) 0.036(8) -0.023(8) O2 0.155(13) 0.102(10) 0.249(19) 0.012(13) 0.089(15) -0.006(9) Cl1 0.063(8) 0.085(9) 0.075(9) 0.006(6) 0.008(6) -0.012(6) O3 0.109(16) 0.116(16) 0.118(17) -0.011(9) 0.032(10) -0.002(9) O4 0.085(12) 0.063(11) 0.070(11) 0.008(8) 0.028(8) 0.001(8) O5 0.085(13) 0.077(12) 0.086(12) 0.025(8) 0.012(8) 0.008(8) O6 0.081(14) 0.074(13) 0.085(14) -0.006(8) 0.023(9) 0.010(8) Cl2 0.059(7) 0.062(7) 0.065(7) 0.003(4) 0.021(6) 0.011(5) O7 0.061(12) 0.060(12) 0.074(12) 0.005(8) 0.020(8) -0.004(8) O8 0.074(12) 0.075(12) 0.077(11) 0.002(8) 0.027(9) 0.006(8) O9 0.079(12) 0.072(12) 0.069(11) 0.004(8) 0.032(8) -0.002(8) O10 0.038(9) 0.065(10) 0.055(8) 0.003(7) 0.022(7) -0.009(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 N6 1.635(12) . ? Mn1 N4 1.998(9) . ? Mn1 N1 2.036(11) . ? Mn1 N3 2.120(10) . ? Mn1 N2 2.121(9) . ? Mn1 N5 2.129(9) . ? N1 C1 1.345(15) . ? N1 C9 1.380(14) . ? C1 C2 1.402(16) . ? C1 H1 0.9500 . ? C2 C3 1.367(15) . ? C2 H2 0.9500 . ? C3 C8 1.412(16) . ? C3 H3 0.9500 . ? C4 C5 1.340(14) . ? C4 C8 1.426(15) . ? C4 H4 0.9500 . ? C5 C6 1.422(14) . ? C5 H5 0.9500 . ? C6 C7 1.393(14) . ? C6 H6 0.9500 . ? C7 N4 1.364(14) . ? C7 C9 1.387(15) . ? C8 C9 1.401(16) . ? N2 C14 1.340(13) . ? N2 C10 1.370(14) . ? C10 C11 1.391(15) . ? C10 C21 1.522(15) . ? C11 C12 1.378(14) . ? C11 H11 0.9500 . ? C12 C13 1.392(15) . ? C12 H12 0.9500 . ? C13 C14 1.369(16) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N3 C15 1.365(14) . ? N3 C19 1.381(15) . ? C15 C16 1.347(16) . ? C15 C22 1.505(17) . ? C16 C17 1.373(15) . ? C16 H16 0.9500 . ? C17 C18 1.353(16) . ? C17 H17 0.9500 . ? C18 C19 1.371(17) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? N4 C20 1.366(16) . ? C20 O1 1.225(15) . ? C20 C23 1.522(16) . ? N5 C21 1.482(12) . ? N5 C22 1.500(13) . ? N5 C23 1.512(13) . ? C21 H21 0.9900 . ? C21 H21A 0.9900 . ? C22 H22 0.9900 . ? C22 H22A 0.9900 . ? C23 H23 0.9900 . ? C23 H23A 0.9900 . ? N6 O2 1.022(16) . ? Cl1 O4 1.418(19) . ? Cl1 O5 1.422(19) . ? Cl1 O6 1.431(19) . ? Cl1 O3 1.49(3) . ? Cl2 O10 1.413(18) . ? Cl2 O8 1.45(2) . ? Cl2 O9 1.47(2) . ? Cl2 O7 1.48(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 N6 Mn1 N4 176.9(6) . . ? N6 Mn1 N1 98.1(7) . . ? N4 Mn1 N1 78.9(5) . . ? N6 Mn1 N3 90.4(6) . . ? N4 Mn1 N3 91.0(3) . . ? N1 Mn1 N3 104.3(4) . . ? N6 Mn1 N2 92.3(6) . . ? N4 Mn1 N2 87.4(3) . . ? N1 Mn1 N2 96.7(4) . . ? N3 Mn1 N2 158.2(5) . . ? N6 Mn1 N5 100.7(6) . . ? N4 Mn1 N5 82.3(4) . . ? N1 Mn1 N5 161.0(4) . . ? N3 Mn1 N5 78.2(4) . . ? N2 Mn1 N5 80.1(4) . . ? C1 N1 C9 118.4(12) . . ? C1 N1 Mn1 128.3(11) . . ? C9 N1 Mn1 113.4(9) . . ? N1 C1 C2 122.9(13) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 118.4(13) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C8 120.8(13) . . ? C2 C3 H3 119.6 . . ? C8 C3 H3 119.6 . . ? C5 C4 C8 118.2(11) . . ? C5 C4 H4 120.9 . . ? C8 C4 H4 120.9 . . ? C4 C5 C6 121.9(12) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C7 C6 C5 120.6(11) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? N4 C7 C9 114.1(12) . . ? N4 C7 C6 128.3(12) . . ? C9 C7 C6 117.6(12) . . ? C9 C8 C3 117.7(13) . . ? C9 C8 C4 120.0(12) . . ? C3 C8 C4 122.3(14) . . ? N1 C9 C7 116.7(13) . . ? N1 C9 C8 121.6(12) . . ? C7 C9 C8 121.6(13) . . ? C14 N2 C10 119.0(11) . . ? C14 N2 Mn1 127.4(9) . . ? C10 N2 Mn1 113.1(9) . . ? N2 C10 C11 120.0(11) . . ? N2 C10 C21 114.7(12) . . ? C11 C10 C21 125.0(12) . . ? C12 C11 C10 119.7(12) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 120.1(12) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C14 C13 C12 117.5(12) . . ? C14 C13 H13 121.3 . . ? C12 C13 H13 121.3 . . ? N2 C14 C13 123.7(12) . . ? N2 C14 H14 118.1 . . ? C13 C14 H14 118.1 . . ? C15 N3 C19 117.7(11) . . ? C15 N3 Mn1 116.0(9) . . ? C19 N3 Mn1 126.3(10) . . ? C16 C15 N3 119.6(13) . . ? C16 C15 C22 127.3(13) . . ? N3 C15 C22 113.1(11) . . ? C15 C16 C17 123.1(14) . . ? C15 C16 H16 118.5 . . ? C17 C16 H16 118.5 . . ? C18 C17 C16 117.8(14) . . ? C18 C17 H17 121.1 . . ? C16 C17 H17 121.1 . . ? C17 C18 C19 119.9(15) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C18 C19 N3 121.8(13) . . ? C18 C19 H19 119.1 . . ? N3 C19 H19 119.1 . . ? C7 N4 C20 122.9(10) . . ? C7 N4 Mn1 116.6(8) . . ? C20 N4 Mn1 119.7(8) . . ? O1 C20 N4 127.6(11) . . ? O1 C20 C23 119.0(14) . . ? N4 C20 C23 113.2(13) . . ? C21 N5 C22 111.5(9) . . ? C21 N5 C23 113.1(8) . . ? C22 N5 C23 110.2(8) . . ? C21 N5 Mn1 106.3(6) . . ? C22 N5 Mn1 106.6(6) . . ? C23 N5 Mn1 108.7(6) . . ? N5 C21 C10 109.6(9) . . ? N5 C21 H21 109.7 . . ? C10 C21 H21 109.7 . . ? N5 C21 H21A 109.7 . . ? C10 C21 H21A 109.7 . . ? H21 C21 H21A 108.2 . . ? N5 C22 C15 111.0(9) . . ? N5 C22 H22 109.4 . . ? C15 C22 H22 109.4 . . ? N5 C22 H22A 109.4 . . ? C15 C22 H22A 109.4 . . ? H22 C22 H22A 108.0 . . ? N5 C23 C20 115.2(11) . . ? N5 C23 H23 108.5 . . ? C20 C23 H23 108.5 . . ? N5 C23 H23A 108.5 . . ? C20 C23 H23A 108.5 . . ? H23 C23 H23A 107.5 . . ? O2 N6 Mn1 171(2) . . ? O4 Cl1 O5 112.0(13) . . ? O4 Cl1 O6 111.1(13) . . ? O5 Cl1 O6 110.7(12) . . ? O4 Cl1 O3 107.8(12) . . ? O5 Cl1 O3 107.8(12) . . ? O6 Cl1 O3 107.2(13) . . ? O10 Cl2 O8 112.1(13) . . ? O10 Cl2 O9 110.3(14) . . ? O8 Cl2 O9 108.5(12) . . ? O10 Cl2 O7 110.4(12) . . ? O8 Cl2 O7 108.4(13) . . ? O9 Cl2 O7 107.0(12) . . ? 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 N6 Mn1 N1 C1 5.0(12) . . . . ? N4 Mn1 N1 C1 -175.7(11) . . . . ? N3 Mn1 N1 C1 -87.5(10) . . . . ? N2 Mn1 N1 C1 98.3(10) . . . . ? N5 Mn1 N1 C1 177.2(10) . . . . ? N6 Mn1 N1 C9 -175.4(9) . . . . ? N4 Mn1 N1 C9 3.9(7) . . . . ? N3 Mn1 N1 C9 92.1(8) . . . . ? N2 Mn1 N1 C9 -82.1(8) . . . . ? N5 Mn1 N1 C9 -3.2(16) . . . . ? C9 N1 C1 C2 4.5(17) . . . . ? Mn1 N1 C1 C2 -175.9(9) . . . . ? N1 C1 C2 C3 -1.5(18) . . . . ? C1 C2 C3 C8 -1.0(18) . . . . ? C8 C4 C5 C6 -2.1(17) . . . . ? C4 C5 C6 C7 2.7(17) . . . . ? C5 C6 C7 N4 179.3(11) . . . . ? C5 C6 C7 C9 -2.1(16) . . . . ? C2 C3 C8 C9 0.4(17) . . . . ? C2 C3 C8 C4 -179.4(10) . . . . ? C5 C4 C8 C9 1.2(16) . . . . ? C5 C4 C8 C3 -179.0(11) . . . . ? C1 N1 C9 C7 178.0(10) . . . . ? Mn1 N1 C9 C7 -1.7(13) . . . . ? C1 N1 C9 C8 -5.1(16) . . . . ? Mn1 N1 C9 C8 175.3(9) . . . . ? N4 C7 C9 N1 -3.1(15) . . . . ? C6 C7 C9 N1 178.2(10) . . . . ? N4 C7 C9 C8 180.0(10) . . . . ? C6 C7 C9 C8 1.2(16) . . . . ? C3 C8 C9 N1 2.7(17) . . . . ? C4 C8 C9 N1 -177.5(10) . . . . ? C3 C8 C9 C7 179.5(10) . . . . ? C4 C8 C9 C7 -0.7(17) . . . . ? N6 Mn1 N2 C14 97.3(11) . . . . ? N4 Mn1 N2 C14 -79.7(9) . . . . ? N1 Mn1 N2 C14 -1.2(10) . . . . ? N3 Mn1 N2 C14 -165.9(9) . . . . ? N5 Mn1 N2 C14 -162.3(10) . . . . ? N6 Mn1 N2 C10 -90.6(9) . . . . ? N4 Mn1 N2 C10 92.4(8) . . . . ? N1 Mn1 N2 C10 170.9(8) . . . . ? N3 Mn1 N2 C10 6.2(14) . . . . ? N5 Mn1 N2 C10 9.8(7) . . . . ? C14 N2 C10 C11 -1.3(15) . . . . ? Mn1 N2 C10 C11 -174.1(8) . . . . ? C14 N2 C10 C21 -175.2(9) . . . . ? Mn1 N2 C10 C21 12.0(11) . . . . ? N2 C10 C11 C12 1.8(16) . . . . ? C21 C10 C11 C12 175.0(9) . . . . ? C10 C11 C12 C13 -1.2(16) . . . . ? C11 C12 C13 C14 0.0(16) . . . . ? C10 N2 C14 C13 0.1(17) . . . . ? Mn1 N2 C14 C13 171.8(9) . . . . ? C12 C13 C14 N2 0.5(18) . . . . ? N6 Mn1 N3 C15 85.1(9) . . . . ? N4 Mn1 N3 C15 -97.6(8) . . . . ? N1 Mn1 N3 C15 -176.4(8) . . . . ? N2 Mn1 N3 C15 -12.1(14) . . . . ? N5 Mn1 N3 C15 -15.7(7) . . . . ? N6 Mn1 N3 C19 -93.5(11) . . . . ? N4 Mn1 N3 C19 83.7(10) . . . . ? N1 Mn1 N3 C19 4.9(10) . . . . ? N2 Mn1 N3 C19 169.3(9) . . . . ? N5 Mn1 N3 C19 165.6(10) . . . . ? C19 N3 C15 C16 -4.5(15) . . . . ? Mn1 N3 C15 C16 176.7(8) . . . . ? C19 N3 C15 C22 174.9(10) . . . . ? Mn1 N3 C15 C22 -3.9(11) . . . . ? N3 C15 C16 C17 4.5(17) . . . . ? C22 C15 C16 C17 -174.8(11) . . . . ? C15 C16 C17 C18 -1.7(18) . . . . ? C16 C17 C18 C19 -0.8(18) . . . . ? C17 C18 C19 N3 0.6(19) . . . . ? C15 N3 C19 C18 2.1(17) . . . . ? Mn1 N3 C19 C18 -179.3(8) . . . . ? C9 C7 N4 C20 176.5(10) . . . . ? C6 C7 N4 C20 -5.0(18) . . . . ? C9 C7 N4 Mn1 6.6(12) . . . . ? C6 C7 N4 Mn1 -174.8(9) . . . . ? N6 Mn1 N4 C7 7(12) . . . . ? N1 Mn1 N4 C7 -5.8(7) . . . . ? N3 Mn1 N4 C7 -110.2(8) . . . . ? N2 Mn1 N4 C7 91.6(8) . . . . ? N5 Mn1 N4 C7 171.9(8) . . . . ? N6 Mn1 N4 C20 -163(12) . . . . ? N1 Mn1 N4 C20 -176.0(9) . . . . ? N3 Mn1 N4 C20 79.6(8) . . . . ? N2 Mn1 N4 C20 -78.7(8) . . . . ? N5 Mn1 N4 C20 1.6(8) . . . . ? C7 N4 C20 O1 8.2(18) . . . . ? Mn1 N4 C20 O1 177.8(9) . . . . ? C7 N4 C20 C23 -176.9(9) . . . . ? Mn1 N4 C20 C23 -7.3(12) . . . . ? N6 Mn1 N5 C21 61.5(9) . . . . ? N4 Mn1 N5 C21 -117.7(7) . . . . ? N1 Mn1 N5 C21 -110.6(12) . . . . ? N3 Mn1 N5 C21 149.7(7) . . . . ? N2 Mn1 N5 C21 -29.0(6) . . . . ? N6 Mn1 N5 C22 -57.6(9) . . . . ? N4 Mn1 N5 C22 123.2(7) . . . . ? N1 Mn1 N5 C22 130.3(11) . . . . ? N3 Mn1 N5 C22 30.6(7) . . . . ? N2 Mn1 N5 C22 -148.1(7) . . . . ? N6 Mn1 N5 C23 -176.4(8) . . . . ? N4 Mn1 N5 C23 4.4(7) . . . . ? N1 Mn1 N5 C23 11.4(15) . . . . ? N3 Mn1 N5 C23 -88.3(7) . . . . ? N2 Mn1 N5 C23 93.1(7) . . . . ? C22 N5 C21 C10 158.7(9) . . . . ? C23 N5 C21 C10 -76.3(11) . . . . ? Mn1 N5 C21 C10 42.9(10) . . . . ? N2 C10 C21 N5 -37.7(13) . . . . ? C11 C10 C21 N5 148.8(10) . . . . ? C21 N5 C22 C15 -157.8(9) . . . . ? C23 N5 C22 C15 75.7(11) . . . . ? Mn1 N5 C22 C15 -42.2(10) . . . . ? C16 C15 C22 N5 -149.4(11) . . . . ? N3 C15 C22 N5 31.2(13) . . . . ? C21 N5 C23 C20 108.5(11) . . . . ? C22 N5 C23 C20 -125.9(10) . . . . ? Mn1 N5 C23 C20 -9.4(11) . . . . ? O1 C20 C23 N5 -173.6(10) . . . . ? N4 C20 C23 N5 11.1(14) . . . . ? N4 Mn1 N6 O2 169(7) . . . . ? N1 Mn1 N6 O2 -178(13) . . . . ? N3 Mn1 N6 O2 -74(13) . . . . ? N2 Mn1 N6 O2 85(13) . . . . ? N5 Mn1 N6 O2 4(13) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 50.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.217 _refine_diff_density_min -0.663 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 947310' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ydkr _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[[Mn(dpaqCl)(NO)]ClO4' _chemical_formula_moiety 'C23 H19 Cl Mn N6 O2' _chemical_formula_sum 'C23 H19 Cl2 Mn N6 O6' _chemical_melting_point ? _exptl_crystal_description platelet _exptl_crystal_colour brown _diffrn_ambient_temperature 123(2) _chemical_formula_weight 601.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.88120(10) _cell_length_b 10.14710(10) _cell_length_c 26.2914(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.9655(8) _cell_angle_gamma 90.00 _cell_volume 2366.17(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 28543 _cell_measurement_theta_min 3.365 _cell_measurement_theta_max 68.25 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 7.104 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6003 _exptl_absorpt_correction_T_max 0.8151 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector IP _diffrn_measurement_device_type 'RIGAKU R-AXISIP' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31658 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 52.49 _reflns_number_total 2634 _reflns_number_gt 2303 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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. The disordered perchlorate ion was modeled with SADI restraints in order to yield similar O...O distances. The Cl-O distances were restrained to 1.42 (2) A with DFIX restraints. The O atoms of the perchlorae ion were treated as disordered over three sites (30:30:40). Additonally, the vibration ofthe oxygen atoms was made somewhat isotropic by an ISOR restraint. ; _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^)+(0.0316P)^2^+2.8288P] 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 0.00001(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2634 _refine_ls_number_parameters 416 _refine_ls_number_restraints 129 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0809 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.075 _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 O1 O 0.5828(3) 0.2512(2) 0.23784(9) 0.0360(7) Uani 1 1 d . . . O2 O 0.9016(3) -0.1000(3) 0.05202(11) 0.0467(8) Uani 1 1 d . . . O3 O 1.2017(15) 0.602(2) 0.1578(9) 0.102(8) Uani 0.30 1 d PDU A 1 O4 O 1.1612(19) 0.505(2) 0.1086(7) 0.087(9) Uani 0.30 1 d PDU A 2 O5 O 0.979(2) 0.6771(14) 0.1186(8) 0.078(8) Uani 0.30 1 d PDU A 1 O6 O 0.975(2) 0.507(2) 0.1769(8) 0.056(8) Uani 0.30 1 d PDU A 1 O7 O 1.072(3) 0.4717(19) 0.0985(6) 0.050(7) Uani 0.30 1 d PDU A 1 O8 O 1.1342(17) 0.6529(14) 0.1749(5) 0.056(5) Uani 0.30 1 d PDU A 2 O9 O 0.9500(17) 0.6419(17) 0.1100(6) 0.030(5) Uani 0.30 1 d PDU A 2 O10 O 0.979(2) 0.4690(17) 0.1672(7) 0.060(8) Uani 0.30 1 d PDU A 2 O11 O 1.010(2) 0.4813(17) 0.1797(7) 0.046(5) Uani 0.40 1 d PDU A 3 O12 O 0.9245(18) 0.6375(18) 0.1202(7) 0.104(8) Uani 0.40 1 d PDU A 3 O13 O 1.111(3) 0.4852(19) 0.0997(7) 0.060(7) Uani 0.40 1 d PDU A 3 O14 O 1.166(2) 0.6559(18) 0.1576(8) 0.100(8) Uani 0.40 1 d PDU A 3 Cl1 Cl 0.58682(12) 0.68715(9) 0.03488(4) 0.0471(3) Uani 1 1 d . . . Cl2 Cl 1.05552(12) 0.56542(10) 0.13933(4) 0.0423(3) Uani 1 1 d D . . Mn1 Mn 0.79213(6) 0.07147(6) 0.12218(2) 0.0279(2) Uani 1 1 d . . . N1 N 0.8030(3) 0.2236(3) 0.07363(11) 0.0311(8) Uani 1 1 d . . . C1 C 0.8724(4) 0.2279(4) 0.03022(14) 0.0355(10) Uani 1 1 d . . . H1 H 0.9288 0.1531 0.0206 0.043 Uiso 1 1 calc R . . C2 C 0.8664(4) 0.3372(4) -0.00197(14) 0.0375(10) Uani 1 1 d . . . H2 H 0.9204 0.3369 -0.0322 0.045 Uiso 1 1 calc R . . C3 C 0.7834(4) 0.4438(4) 0.01002(14) 0.0367(10) Uani 1 1 d . . . H3 H 0.7766 0.5175 -0.0123 0.044 Uiso 1 1 calc R . . C4 C 0.6135(4) 0.5463(4) 0.07296(15) 0.0352(10) Uani 1 1 d . . . C5 C 0.5449(4) 0.5378(4) 0.11774(15) 0.0371(10) Uani 1 1 d . . . H5 H 0.4795 0.6065 0.1274 0.045 Uiso 1 1 calc R . . C6 C 0.5692(4) 0.4286(3) 0.15006(14) 0.0331(10) Uani 1 1 d . . . H6 H 0.5229 0.4256 0.1818 0.040 Uiso 1 1 calc R . . C7 C 0.6596(4) 0.3260(4) 0.13597(13) 0.0285(9) Uani 1 1 d . . . C8 C 0.7069(4) 0.4448(4) 0.05580(14) 0.0308(9) Uani 1 1 d . . . C9 C 0.7239(4) 0.3333(4) 0.08765(13) 0.0280(9) Uani 1 1 d . . . N2 N 0.9944(3) 0.0999(3) 0.16134(11) 0.0305(8) Uani 1 1 d . . . C10 C 1.0260(4) 0.0065(4) 0.19748(13) 0.0302(9) Uani 1 1 d . . . C11 C 1.1597(4) 0.0073(4) 0.22676(14) 0.0343(10) Uani 1 1 d . . . H11 H 1.1806 -0.0591 0.2516 0.041 Uiso 1 1 calc R . . C12 C 1.2624(5) 0.1066(4) 0.21918(15) 0.0414(11) Uani 1 1 d . . . H12 H 1.3552 0.1089 0.2388 0.050 Uiso 1 1 calc R . . C13 C 1.2305(5) 0.2014(4) 0.18343(15) 0.0400(10) Uani 1 1 d . . . H13 H 1.3000 0.2708 0.1783 0.048 Uiso 1 1 calc R . . C14 C 1.0966(5) 0.1953(4) 0.15495(14) 0.0376(10) Uani 1 1 d . . . H14 H 1.0755 0.2609 0.1298 0.045 Uiso 1 1 calc R . . N3 N 0.5736(3) 0.0122(3) 0.10322(11) 0.0312(8) Uani 1 1 d . . . C15 C 0.5256(4) -0.0840(4) 0.13405(13) 0.0296(9) Uani 1 1 d . . . C16 C 0.3782(4) -0.1278(4) 0.13162(15) 0.0344(10) Uani 1 1 d . . . H16 H 0.3454 -0.1920 0.1549 0.041 Uiso 1 1 calc R . . C17 C 0.2800(5) -0.0762(4) 0.09464(16) 0.0416(11) Uani 1 1 d . . . H17 H 0.1790 -0.1069 0.0913 0.050 Uiso 1 1 calc R . . C18 C 0.3287(5) 0.0199(4) 0.06256(15) 0.0442(11) Uani 1 1 d . . . H18 H 0.2620 0.0561 0.0368 0.053 Uiso 1 1 calc R . . C19 C 0.4754(5) 0.0630(4) 0.06834(14) 0.0375(10) Uani 1 1 d . . . H19 H 0.5080 0.1313 0.0468 0.045 Uiso 1 1 calc R . . N4 N 0.6970(3) 0.2066(3) 0.16181(10) 0.0276(7) Uani 1 1 d . . . C20 C 0.6531(4) 0.1799(4) 0.20899(14) 0.0280(9) Uani 1 1 d . . . N5 N 0.7589(3) -0.0409(3) 0.18485(11) 0.0275(7) Uani 1 1 d . . . C21 C 0.9085(4) -0.0977(4) 0.20111(14) 0.0319(10) Uani 1 1 d . . . H21 H 0.9318 -0.1731 0.1789 0.038 Uiso 1 1 calc R . . H21A H 0.9066 -0.1301 0.2366 0.038 Uiso 1 1 calc R . . C22 C 0.6469(4) -0.1438(4) 0.16877(13) 0.0327(10) Uani 1 1 d . . . H22 H 0.6015 -0.1818 0.1991 0.039 Uiso 1 1 calc R . . H22A H 0.6977 -0.2157 0.1508 0.039 Uiso 1 1 calc R . . C23 C 0.7020(4) 0.0443(4) 0.22632(14) 0.0351(10) Uani 1 1 d . . . H23 H 0.7826 0.0533 0.2536 0.042 Uiso 1 1 calc R . . H23A H 0.6155 -0.0004 0.2412 0.042 Uiso 1 1 calc R . . N6 N 0.8634(4) -0.0412(3) 0.08129(13) 0.0310(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 O1 0.0330(16) 0.0412(16) 0.0342(15) -0.0065(13) 0.0050(13) -0.0035(13) O2 0.0338(19) 0.063(2) 0.0435(19) 0.0126(17) 0.0000(15) 0.0006(16) O3 0.087(13) 0.143(17) 0.073(11) 0.017(12) -0.015(10) -0.064(11) O4 0.056(12) 0.091(15) 0.117(16) 0.049(11) 0.051(10) 0.050(11) O5 0.152(18) 0.047(9) 0.035(9) -0.004(8) 0.009(10) 0.044(11) O6 0.053(12) 0.067(15) 0.049(13) 0.007(9) 0.021(9) 0.006(10) O7 0.098(15) 0.035(9) 0.020(8) -0.016(7) 0.028(8) -0.018(9) O8 0.047(9) 0.047(9) 0.068(9) 0.032(7) -0.049(8) -0.020(7) O9 0.032(9) 0.038(9) 0.019(7) 0.006(7) 0.000(7) 0.003(7) O10 0.079(14) 0.068(13) 0.035(10) -0.024(8) 0.031(9) -0.050(10) O11 0.095(12) 0.013(6) 0.032(8) -0.013(5) 0.022(7) 0.002(7) O12 0.072(10) 0.094(13) 0.138(15) -0.062(10) -0.060(10) 0.043(9) O13 0.063(11) 0.058(11) 0.065(11) 0.024(8) 0.054(8) 0.013(9) O14 0.095(12) 0.086(11) 0.118(14) 0.008(9) 0.006(11) -0.067(9) Cl1 0.0557(7) 0.0344(6) 0.0504(6) 0.0057(5) -0.0033(5) 0.0027(5) Cl2 0.0468(8) 0.0436(7) 0.0364(6) 0.0091(5) 0.0007(6) -0.0028(6) Mn1 0.0272(4) 0.0300(4) 0.0266(4) -0.0036(3) 0.0032(3) -0.0001(3) N1 0.0283(19) 0.037(2) 0.0278(18) -0.0073(15) 0.0031(15) -0.0012(16) C1 0.035(3) 0.039(2) 0.033(2) -0.008(2) 0.003(2) 0.000(2) C2 0.039(3) 0.047(3) 0.027(2) -0.005(2) 0.0078(19) -0.005(2) C3 0.038(3) 0.038(3) 0.033(2) 0.0010(19) -0.002(2) -0.008(2) C4 0.033(2) 0.028(2) 0.043(3) 0.0007(19) -0.006(2) -0.004(2) C5 0.032(3) 0.028(2) 0.051(3) -0.010(2) 0.004(2) 0.0011(19) C6 0.032(2) 0.028(2) 0.039(2) -0.0070(19) 0.0087(19) -0.007(2) C7 0.025(2) 0.030(2) 0.030(2) -0.0068(18) -0.0031(18) -0.0067(19) C8 0.029(2) 0.030(2) 0.033(2) -0.0034(19) -0.0053(19) -0.0046(19) C9 0.022(2) 0.029(2) 0.032(2) -0.0057(19) -0.0028(18) -0.0026(18) N2 0.034(2) 0.0284(18) 0.0294(18) -0.0031(15) 0.0053(15) -0.0015(16) C10 0.035(3) 0.030(2) 0.026(2) -0.0051(18) 0.0067(19) -0.002(2) C11 0.029(3) 0.043(3) 0.031(2) -0.0063(19) 0.000(2) 0.002(2) C12 0.029(3) 0.055(3) 0.040(3) -0.021(2) 0.001(2) -0.002(2) C13 0.035(3) 0.040(3) 0.046(3) -0.010(2) 0.006(2) -0.008(2) C14 0.042(3) 0.033(2) 0.038(2) -0.0023(19) 0.008(2) 0.000(2) N3 0.034(2) 0.0315(19) 0.0282(17) -0.0014(15) 0.0026(16) 0.0040(16) C15 0.032(3) 0.031(2) 0.026(2) -0.0068(18) 0.0056(18) -0.0030(19) C16 0.029(3) 0.036(2) 0.040(2) -0.0155(19) 0.006(2) -0.003(2) C17 0.027(3) 0.048(3) 0.050(3) -0.024(2) 0.000(2) -0.002(2) C18 0.038(3) 0.056(3) 0.038(3) -0.013(2) -0.009(2) 0.008(2) C19 0.042(3) 0.042(3) 0.028(2) -0.0017(19) 0.001(2) 0.007(2) N4 0.0196(18) 0.041(2) 0.0224(17) -0.0003(15) 0.0034(13) -0.0050(15) C20 0.023(2) 0.030(2) 0.032(2) -0.0089(19) 0.0013(18) -0.0050(18) N5 0.0229(18) 0.0291(18) 0.0308(17) -0.0008(14) 0.0043(14) -0.0011(15) C21 0.034(3) 0.035(2) 0.027(2) 0.0039(18) 0.0019(18) 0.001(2) C22 0.036(3) 0.032(2) 0.031(2) 0.0054(18) 0.0028(19) -0.0082(19) C23 0.036(2) 0.041(2) 0.029(2) -0.0034(19) 0.0046(18) -0.003(2) N6 0.025(2) 0.029(2) 0.038(2) 0.0072(17) -0.0084(17) -0.0042(16) _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 O1 C20 1.240(4) . ? O2 N6 1.044(4) . ? O3 Cl2 1.413(10) . ? O4 Cl2 1.409(10) . ? O5 Cl2 1.415(9) . ? O6 Cl2 1.382(16) . ? O7 Cl2 1.449(9) . ? O8 Cl2 1.443(9) . ? O9 Cl2 1.414(9) . ? O10 Cl2 1.416(10) . ? O11 Cl2 1.436(13) . ? O12 Cl2 1.443(12) . ? O13 Cl2 1.432(12) . ? O14 Cl2 1.412(12) . ? Cl1 C4 1.754(4) . ? Mn1 N6 1.713(4) . ? Mn1 N4 1.941(3) . ? Mn1 N1 2.008(3) . ? Mn1 N5 2.038(3) . ? Mn1 N2 2.044(3) . ? Mn1 N3 2.068(3) . ? N1 C1 1.326(4) . ? N1 C9 1.377(4) . ? C1 C2 1.395(5) . ? C1 H1 0.9500 . ? C2 C3 1.356(5) . ? C2 H2 0.9500 . ? C3 C8 1.412(5) . ? C3 H3 0.9500 . ? C4 C5 1.357(5) . ? C4 C8 1.411(5) . ? C5 C6 1.406(5) . ? C5 H5 0.9500 . ? C6 C7 1.377(5) . ? C6 H6 0.9500 . ? C7 N4 1.420(4) . ? C7 C9 1.421(5) . ? C8 C9 1.411(5) . ? N2 C14 1.344(5) . ? N2 C10 1.361(4) . ? C10 C11 1.381(5) . ? C10 C21 1.493(5) . ? C11 C12 1.380(5) . ? C11 H11 0.9500 . ? C12 C13 1.365(5) . ? C12 H12 0.9500 . ? C13 C14 1.373(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N3 C19 1.336(5) . ? N3 C15 1.352(4) . ? C15 C16 1.380(5) . ? C15 C22 1.503(5) . ? C16 C17 1.376(5) . ? C16 H16 0.9500 . ? C17 C18 1.374(6) . ? C17 H17 0.9500 . ? C18 C19 1.376(5) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? N4 C20 1.347(4) . ? C20 C23 1.506(5) . ? N5 C22 1.489(4) . ? N5 C21 1.490(4) . ? N5 C23 1.500(4) . ? C21 H21 0.9900 . ? C21 H21A 0.9900 . ? C22 H22 0.9900 . ? C22 H22A 0.9900 . ? C23 H23 0.9900 . ? C23 H23A 0.9900 . ? 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 O6 Cl2 O4 127.6(14) . . ? O6 Cl2 O14 114.4(17) . . ? O4 Cl2 O14 90.2(15) . . ? O6 Cl2 O3 111.7(8) . . ? O4 Cl2 O3 71.6(13) . . ? O14 Cl2 O3 25.6(14) . . ? O6 Cl2 O9 105.8(15) . . ? O4 Cl2 O9 111.5(7) . . ? O14 Cl2 O9 105.0(13) . . ? O3 Cl2 O9 127.8(12) . . ? O6 Cl2 O5 111.3(8) . . ? O4 Cl2 O5 116.4(14) . . ? O14 Cl2 O5 85.5(13) . . ? O3 Cl2 O5 109.4(7) . . ? O9 Cl2 O5 20.0(10) . . ? O6 Cl2 O10 19.2(14) . . ? O4 Cl2 O10 110.4(7) . . ? O14 Cl2 O10 128.2(12) . . ? O3 Cl2 O10 117.5(13) . . ? O9 Cl2 O10 109.9(7) . . ? O5 Cl2 O10 121.5(15) . . ? O6 Cl2 O13 119.3(16) . . ? O4 Cl2 O13 21.5(15) . . ? O14 Cl2 O13 110.8(8) . . ? O3 Cl2 O13 93.1(17) . . ? O9 Cl2 O13 99.1(13) . . ? O5 Cl2 O13 110.5(14) . . ? O10 Cl2 O13 100.2(14) . . ? O6 Cl2 O11 16.8(14) . . ? O4 Cl2 O11 112.7(14) . . ? O14 Cl2 O11 110.6(8) . . ? O3 Cl2 O11 101.0(15) . . ? O9 Cl2 O11 121.8(11) . . ? O5 Cl2 O11 128.0(13) . . ? O10 Cl2 O11 17.6(13) . . ? O13 Cl2 O11 108.7(7) . . ? O6 Cl2 O12 91.6(14) . . ? O4 Cl2 O12 124.7(13) . . ? O14 Cl2 O12 108.9(7) . . ? O3 Cl2 O12 134.0(13) . . ? O9 Cl2 O12 14.6(11) . . ? O5 Cl2 O12 25.7(13) . . ? O10 Cl2 O12 97.6(13) . . ? O13 Cl2 O12 109.7(7) . . ? O11 Cl2 O12 108.0(7) . . ? O6 Cl2 O8 92.9(13) . . ? O4 Cl2 O8 108.9(7) . . ? O14 Cl2 O8 22.3(13) . . ? O3 Cl2 O8 37.7(11) . . ? O9 Cl2 O8 107.5(6) . . ? O5 Cl2 O8 87.9(9) . . ? O10 Cl2 O8 108.5(6) . . ? O13 Cl2 O8 130.4(14) . . ? O11 Cl2 O8 91.7(12) . . ? O12 Cl2 O8 105.6(12) . . ? O6 Cl2 O7 109.1(7) . . ? O4 Cl2 O7 36.1(13) . . ? O14 Cl2 O7 125.6(16) . . ? O3 Cl2 O7 107.5(8) . . ? O9 Cl2 O7 92.7(11) . . ? O5 Cl2 O7 107.8(7) . . ? O10 Cl2 O7 90.0(14) . . ? O13 Cl2 O7 14.8(18) . . ? O11 Cl2 O7 101.6(16) . . ? O12 Cl2 O7 100.8(14) . . ? O8 Cl2 O7 145.0(12) . . ? N6 Mn1 N4 173.37(13) . . ? N6 Mn1 N1 94.74(13) . . ? N4 Mn1 N1 80.50(12) . . ? N6 Mn1 N5 101.98(13) . . ? N4 Mn1 N5 82.87(11) . . ? N1 Mn1 N5 163.26(12) . . ? N6 Mn1 N2 93.81(13) . . ? N4 Mn1 N2 91.45(11) . . ? N1 Mn1 N2 98.15(12) . . ? N5 Mn1 N2 80.32(12) . . ? N6 Mn1 N3 91.57(13) . . ? N4 Mn1 N3 84.60(11) . . ? N1 Mn1 N3 98.37(12) . . ? N5 Mn1 N3 81.89(12) . . ? N2 Mn1 N3 162.12(12) . . ? C1 N1 C9 118.0(3) . . ? C1 N1 Mn1 127.7(3) . . ? C9 N1 Mn1 114.2(2) . . ? N1 C1 C2 122.9(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.9(4) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C8 119.7(4) . . ? C2 C3 H3 120.2 . . ? C8 C3 H3 120.2 . . ? C5 C4 C8 121.9(3) . . ? C5 C4 Cl1 119.6(3) . . ? C8 C4 Cl1 118.5(3) . . ? C4 C5 C6 120.9(4) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 120.4(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 N4 129.9(3) . . ? C6 C7 C9 117.9(3) . . ? N4 C7 C9 112.2(3) . . ? C9 C8 C4 116.2(3) . . ? C9 C8 C3 117.3(3) . . ? C4 C8 C3 126.4(4) . . ? N1 C9 C8 122.0(3) . . ? N1 C9 C7 115.5(3) . . ? C8 C9 C7 122.5(3) . . ? C14 N2 C10 118.2(3) . . ? C14 N2 Mn1 128.4(3) . . ? C10 N2 Mn1 113.4(2) . . ? N2 C10 C11 121.7(3) . . ? N2 C10 C21 114.7(3) . . ? C11 C10 C21 123.5(3) . . ? C12 C11 C10 118.6(4) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.1(4) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? N2 C14 C13 122.4(4) . . ? N2 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? C19 N3 C15 118.4(3) . . ? C19 N3 Mn1 128.6(3) . . ? C15 N3 Mn1 112.7(2) . . ? N3 C15 C16 122.2(4) . . ? N3 C15 C22 114.7(3) . . ? C16 C15 C22 123.1(3) . . ? C17 C16 C15 118.4(4) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C18 C17 C16 119.8(4) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 119.0(4) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? N3 C19 C18 122.3(4) . . ? N3 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? C20 N4 C7 122.7(3) . . ? C20 N4 Mn1 120.5(2) . . ? C7 N4 Mn1 116.3(2) . . ? O1 C20 N4 128.7(3) . . ? O1 C20 C23 119.6(3) . . ? N4 C20 C23 111.7(3) . . ? C22 N5 C21 112.5(3) . . ? C22 N5 C23 111.4(3) . . ? C21 N5 C23 110.1(3) . . ? C22 N5 Mn1 106.6(2) . . ? C21 N5 Mn1 106.5(2) . . ? C23 N5 Mn1 109.5(2) . . ? N5 C21 C10 108.9(3) . . ? N5 C21 H21 109.9 . . ? C10 C21 H21 109.9 . . ? N5 C21 H21A 109.9 . . ? C10 C21 H21A 109.9 . . ? H21 C21 H21A 108.3 . . ? N5 C22 C15 109.7(3) . . ? N5 C22 H22 109.7 . . ? C15 C22 H22 109.7 . . ? N5 C22 H22A 109.7 . . ? C15 C22 H22A 109.7 . . ? H22 C22 H22A 108.2 . . ? N5 C23 C20 114.2(3) . . ? N5 C23 H23 108.7 . . ? C20 C23 H23 108.7 . . ? N5 C23 H23A 108.7 . . ? C20 C23 H23A 108.7 . . ? H23 C23 H23A 107.6 . . ? O2 N6 Mn1 171.3(3) . . ? 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 N6 Mn1 N1 C1 -11.4(3) . . . . ? N4 Mn1 N1 C1 173.2(3) . . . . ? N5 Mn1 N1 C1 166.6(4) . . . . ? N2 Mn1 N1 C1 83.1(3) . . . . ? N3 Mn1 N1 C1 -103.7(3) . . . . ? N6 Mn1 N1 C9 166.5(2) . . . . ? N4 Mn1 N1 C9 -8.8(2) . . . . ? N5 Mn1 N1 C9 -15.5(5) . . . . ? N2 Mn1 N1 C9 -98.9(2) . . . . ? N3 Mn1 N1 C9 74.2(2) . . . . ? C9 N1 C1 C2 -1.2(5) . . . . ? Mn1 N1 C1 C2 176.7(3) . . . . ? N1 C1 C2 C3 -1.9(6) . . . . ? C1 C2 C3 C8 1.8(6) . . . . ? C8 C4 C5 C6 2.6(6) . . . . ? Cl1 C4 C5 C6 -177.3(3) . . . . ? C4 C5 C6 C7 -2.2(6) . . . . ? C5 C6 C7 N4 -178.7(3) . . . . ? C5 C6 C7 C9 -1.3(5) . . . . ? C5 C4 C8 C9 0.5(5) . . . . ? Cl1 C4 C8 C9 -179.6(3) . . . . ? C5 C4 C8 C3 -180.0(4) . . . . ? Cl1 C4 C8 C3 -0.1(5) . . . . ? C2 C3 C8 C9 1.2(5) . . . . ? C2 C3 C8 C4 -178.3(4) . . . . ? C1 N1 C9 C8 4.3(5) . . . . ? Mn1 N1 C9 C8 -173.8(3) . . . . ? C1 N1 C9 C7 -176.3(3) . . . . ? Mn1 N1 C9 C7 5.6(4) . . . . ? C4 C8 C9 N1 175.2(3) . . . . ? C3 C8 C9 N1 -4.3(5) . . . . ? C4 C8 C9 C7 -4.1(5) . . . . ? C3 C8 C9 C7 176.3(3) . . . . ? C6 C7 C9 N1 -174.8(3) . . . . ? N4 C7 C9 N1 3.0(4) . . . . ? C6 C7 C9 C8 4.5(5) . . . . ? N4 C7 C9 C8 -177.7(3) . . . . ? N6 Mn1 N2 C14 96.4(3) . . . . ? N4 Mn1 N2 C14 -79.6(3) . . . . ? N1 Mn1 N2 C14 1.0(3) . . . . ? N5 Mn1 N2 C14 -162.1(3) . . . . ? N3 Mn1 N2 C14 -156.4(3) . . . . ? N6 Mn1 N2 C10 -82.3(2) . . . . ? N4 Mn1 N2 C10 101.7(2) . . . . ? N1 Mn1 N2 C10 -177.6(2) . . . . ? N5 Mn1 N2 C10 19.2(2) . . . . ? N3 Mn1 N2 C10 24.9(5) . . . . ? C14 N2 C10 C11 -0.7(5) . . . . ? Mn1 N2 C10 C11 178.1(3) . . . . ? C14 N2 C10 C21 -178.4(3) . . . . ? Mn1 N2 C10 C21 0.4(4) . . . . ? N2 C10 C11 C12 0.6(5) . . . . ? C21 C10 C11 C12 178.1(3) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C11 C12 C13 C14 -0.9(6) . . . . ? C10 N2 C14 C13 0.0(5) . . . . ? Mn1 N2 C14 C13 -178.6(3) . . . . ? C12 C13 C14 N2 0.8(6) . . . . ? N6 Mn1 N3 C19 -94.3(3) . . . . ? N4 Mn1 N3 C19 80.2(3) . . . . ? N1 Mn1 N3 C19 0.7(3) . . . . ? N5 Mn1 N3 C19 163.8(3) . . . . ? N2 Mn1 N3 C19 158.1(3) . . . . ? N6 Mn1 N3 C15 91.4(2) . . . . ? N4 Mn1 N3 C15 -94.1(2) . . . . ? N1 Mn1 N3 C15 -173.6(2) . . . . ? N5 Mn1 N3 C15 -10.5(2) . . . . ? N2 Mn1 N3 C15 -16.2(5) . . . . ? C19 N3 C15 C16 -2.1(5) . . . . ? Mn1 N3 C15 C16 172.8(3) . . . . ? C19 N3 C15 C22 174.6(3) . . . . ? Mn1 N3 C15 C22 -10.4(4) . . . . ? N3 C15 C16 C17 3.6(5) . . . . ? C22 C15 C16 C17 -172.9(3) . . . . ? C15 C16 C17 C18 -2.3(5) . . . . ? C16 C17 C18 C19 -0.2(6) . . . . ? C15 N3 C19 C18 -0.6(5) . . . . ? Mn1 N3 C19 C18 -174.7(3) . . . . ? C17 C18 C19 N3 1.8(6) . . . . ? C6 C7 N4 C20 -4.9(6) . . . . ? C9 C7 N4 C20 177.6(3) . . . . ? C6 C7 N4 Mn1 166.9(3) . . . . ? C9 C7 N4 Mn1 -10.6(4) . . . . ? N6 Mn1 N4 C20 138.1(11) . . . . ? N1 Mn1 N4 C20 -177.4(3) . . . . ? N5 Mn1 N4 C20 0.7(3) . . . . ? N2 Mn1 N4 C20 -79.3(3) . . . . ? N3 Mn1 N4 C20 83.2(3) . . . . ? N6 Mn1 N4 C7 -33.9(13) . . . . ? N1 Mn1 N4 C7 10.7(2) . . . . ? N5 Mn1 N4 C7 -171.3(2) . . . . ? N2 Mn1 N4 C7 108.7(2) . . . . ? N3 Mn1 N4 C7 -88.8(2) . . . . ? C7 N4 C20 O1 -3.4(6) . . . . ? Mn1 N4 C20 O1 -174.9(3) . . . . ? C7 N4 C20 C23 177.4(3) . . . . ? Mn1 N4 C20 C23 6.0(4) . . . . ? N6 Mn1 N5 C22 -61.8(2) . . . . ? N4 Mn1 N5 C22 113.6(2) . . . . ? N1 Mn1 N5 C22 120.2(4) . . . . ? N2 Mn1 N5 C22 -153.7(2) . . . . ? N3 Mn1 N5 C22 28.0(2) . . . . ? N6 Mn1 N5 C21 58.5(2) . . . . ? N4 Mn1 N5 C21 -126.1(2) . . . . ? N1 Mn1 N5 C21 -119.5(4) . . . . ? N2 Mn1 N5 C21 -33.4(2) . . . . ? N3 Mn1 N5 C21 148.4(2) . . . . ? N6 Mn1 N5 C23 177.5(2) . . . . ? N4 Mn1 N5 C23 -7.1(2) . . . . ? N1 Mn1 N5 C23 -0.5(5) . . . . ? N2 Mn1 N5 C23 85.6(2) . . . . ? N3 Mn1 N5 C23 -92.6(2) . . . . ? C22 N5 C21 C10 158.7(3) . . . . ? C23 N5 C21 C10 -76.3(3) . . . . ? Mn1 N5 C21 C10 42.3(3) . . . . ? N2 C10 C21 N5 -28.7(4) . . . . ? C11 C10 C21 N5 153.6(3) . . . . ? C21 N5 C22 C15 -157.1(3) . . . . ? C23 N5 C22 C15 78.6(3) . . . . ? Mn1 N5 C22 C15 -40.7(3) . . . . ? N3 C15 C22 N5 34.7(4) . . . . ? C16 C15 C22 N5 -148.6(3) . . . . ? C22 N5 C23 C20 -105.5(3) . . . . ? C21 N5 C23 C20 128.9(3) . . . . ? Mn1 N5 C23 C20 12.1(4) . . . . ? O1 C20 C23 N5 168.9(3) . . . . ? N4 C20 C23 N5 -11.9(4) . . . . ? N4 Mn1 N6 O2 22(3) . . . . ? N1 Mn1 N6 O2 -22(2) . . . . ? N5 Mn1 N6 O2 159(2) . . . . ? N2 Mn1 N6 O2 -120(2) . . . . ? N3 Mn1 N6 O2 77(2) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 52.49 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.317 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 947311' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ydkr _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common '[[Mn(dpaqNO2)(NO)]ClO4' _chemical_formula_moiety 'C25 H22 Cl Mn N8 O8' _chemical_formula_sum 'C25 H22 Cl Mn N8 O8' _chemical_melting_point ? _exptl_crystal_description chip _exptl_crystal_colour brown _diffrn_ambient_temperature 123(2) _chemical_formula_weight 652.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P c' _symmetry_int_tables_number 7 _chemical_absolute_configuration ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 8.50240(10) _cell_length_b 7.29870(10) _cell_length_c 21.7032(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.8707(11) _cell_angle_gamma 90.00 _cell_volume 1330.71(4) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 10584 _cell_measurement_theta_min 4.125 _cell_measurement_theta_max 68.255 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 5.549 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2868 _exptl_absorpt_correction_T_max 0.6069 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector IP _diffrn_measurement_device_type 'RIGAKU R-AXISIP' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10774 _diffrn_reflns_av_R_equivalents 0.0777 _diffrn_reflns_av_sigmaI/netI 0.1051 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 54.99 _reflns_number_total 2990 _reflns_number_gt 2648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RIGAKU CrystalClear' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material ;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009) ; _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. The perchlorate ion was modeled with SADI restraints in order to yield similar O...O distances. The Cl-O distances were restrained to 1.42 (2) A with DFIX restraints. Additonally, the vibration of the oxygen atoms was made somewhat isotropic by an ISOR restraint. ; _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^)+(0.0525P)^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 SHELXL _refine_ls_extinction_coef 0.0009(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.010(7) _refine_ls_number_reflns 2990 _refine_ls_number_parameters 390 _refine_ls_number_restraints 45 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1230 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.026 _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 0.41306(10) 0.84685(11) 0.87261(5) 0.0281(3) Uani 1 1 d . . . N1 N 0.4474(7) 0.8163(7) 0.9664(2) 0.0293(14) Uani 1 1 d . . . C1 C 0.4055(8) 0.9346(10) 1.0075(3) 0.0392(18) Uani 1 1 d . . . H1 H 0.3614 1.0494 0.9933 0.047 Uiso 1 1 calc R . . C2 C 0.4252(10) 0.8931(9) 1.0718(3) 0.0425(19) Uani 1 1 d . . . H2 H 0.3876 0.9758 1.1000 0.051 Uiso 1 1 calc R . . C3 C 0.4981(8) 0.7347(9) 1.0932(3) 0.0374(17) Uani 1 1 d . . . H3 H 0.5135 0.7084 1.1366 0.045 Uiso 1 1 calc R . . C4 C 0.6273(8) 0.4396(9) 1.0651(3) 0.0330(17) Uani 1 1 d . . . C5 C 0.6619(9) 0.3214(9) 1.0191(3) 0.0355(18) Uani 1 1 d . . . H5 H 0.7119 0.2076 1.0310 0.043 Uiso 1 1 calc R . . C6 C 0.6258(9) 0.3643(8) 0.9564(3) 0.0355(18) Uani 1 1 d . . . H6 H 0.6507 0.2811 0.9257 0.043 Uiso 1 1 calc R . . C7 C 0.5522(7) 0.5317(8) 0.9389(3) 0.0309(17) Uani 1 1 d . . . C8 C 0.5512(9) 0.6090(9) 1.0513(3) 0.0359(18) Uani 1 1 d . . . C9 C 0.5182(9) 0.6535(8) 0.9869(3) 0.0333(18) Uani 1 1 d . . . N2 N 0.6356(7) 0.9374(7) 0.8578(3) 0.0329(14) Uani 1 1 d . . . C10 C 0.6456(9) 0.9719(8) 0.7971(3) 0.0356(18) Uani 1 1 d . . . C11 C 0.7850(9) 1.0341(9) 0.7780(4) 0.0395(19) Uani 1 1 d . . . H11 H 0.7909 1.0528 0.7351 0.047 Uiso 1 1 calc R . . C12 C 0.9111(10) 1.0669(10) 0.8221(4) 0.053(2) Uani 1 1 d . . . H12 H 1.0057 1.1150 0.8101 0.064 Uiso 1 1 calc R . . C13 C 0.9067(9) 1.0323(9) 0.8847(4) 0.042(2) Uani 1 1 d . . . H13 H 0.9966 1.0534 0.9157 0.050 Uiso 1 1 calc R . . C14 C 0.7665(9) 0.9663(9) 0.8996(3) 0.0382(18) Uani 1 1 d . . . H14 H 0.7618 0.9394 0.9421 0.046 Uiso 1 1 calc R . . N3 N 0.1957(6) 0.7161(7) 0.8573(3) 0.0296(13) Uani 1 1 d . . . C15 C 0.1326(8) 0.7068(8) 0.7969(4) 0.0330(18) Uani 1 1 d . . . C16 C -0.0059(9) 0.6120(9) 0.7752(4) 0.044(2) Uani 1 1 d . . . H16 H -0.0466 0.6070 0.7319 0.053 Uiso 1 1 calc R . . C17 C -0.0833(10) 0.5247(10) 0.8187(4) 0.053(2) Uani 1 1 d . . . H17 H -0.1798 0.4605 0.8055 0.064 Uiso 1 1 calc R . . C18 C -0.0204(9) 0.5311(10) 0.8808(4) 0.049(2) Uani 1 1 d . . . H18 H -0.0710 0.4692 0.9108 0.059 Uiso 1 1 calc R . . C19 C 0.1184(9) 0.6297(9) 0.8988(4) 0.040(2) Uani 1 1 d . . . H19 H 0.1607 0.6366 0.9419 0.048 Uiso 1 1 calc R . . N4 N 0.5048(6) 0.6004(7) 0.8795(2) 0.0242(13) Uani 1 1 d . . . C20 C 0.5143(8) 0.5022(9) 0.8266(3) 0.0320(17) Uani 1 1 d . . . O1 O 0.5603(6) 0.3455(6) 0.8223(2) 0.0401(13) Uani 1 1 d . . . N5 N 0.3958(6) 0.8008(7) 0.7785(2) 0.0245(12) Uani 1 1 d . . . C21 C 0.4908(8) 0.9460(9) 0.7531(3) 0.0320(17) Uani 1 1 d . . . H21 H 0.4302 1.0623 0.7488 0.038 Uiso 1 1 calc R . . H21A H 0.5131 0.9097 0.7113 0.038 Uiso 1 1 calc R . . C22 C 0.2241(8) 0.8104(9) 0.7531(3) 0.0336(18) Uani 1 1 d . . . H22 H 0.2042 0.7548 0.7110 0.040 Uiso 1 1 calc R . . H22A H 0.1888 0.9397 0.7497 0.040 Uiso 1 1 calc R . . C23 C 0.4610(9) 0.6142(8) 0.7677(3) 0.0381(19) Uani 1 1 d . . . H23 H 0.5528 0.6289 0.7452 0.046 Uiso 1 1 calc R . . H23A H 0.3783 0.5441 0.7404 0.046 Uiso 1 1 calc R . . N6 N 0.3324(6) 1.0542(7) 0.8712(3) 0.0274(13) Uani 1 1 d . . . O2 O 0.2804(8) 1.1967(9) 0.8741(3) 0.0792(19) Uani 1 1 d . . . N7 N 0.6757(7) 0.3804(10) 1.1298(3) 0.0418(16) Uani 1 1 d . . . O3 O 0.6920(6) 0.2154(7) 1.1406(2) 0.0520(14) Uani 1 1 d . . . O4 O 0.7041(6) 0.4998(8) 1.1702(2) 0.0479(14) Uani 1 1 d . . . Cl1 Cl 0.1377(2) 0.3352(2) 1.07024(8) 0.0413(5) Uani 1 1 d D . . O5 O 0.1023(6) 0.1950(6) 1.0245(2) 0.0720(18) Uani 1 1 d DU . . O6 O 0.0191(5) 0.3341(6) 1.1112(2) 0.0488(14) Uani 1 1 d DU . . O7 O 0.2915(5) 0.3019(6) 1.1066(2) 0.0507(14) Uani 1 1 d DU . . O8 O 0.1379(7) 0.5099(6) 1.0411(2) 0.0668(17) Uani 1 1 d DU . . C24 C -0.0421(11) 0.1754(10) 0.6041(5) 0.059(2) Uani 1 1 d . . . H24 H -0.1425 0.1422 0.6181 0.089 Uiso 1 1 calc R . . H24A H -0.0043 0.0718 0.5816 0.089 Uiso 1 1 calc R . . H24B H -0.0593 0.2817 0.5763 0.089 Uiso 1 1 calc R . . C25 C 0.0756(13) 0.2202(10) 0.6576(4) 0.054(2) Uani 1 1 d . . . N8 N 0.1697(10) 0.2549(9) 0.6986(4) 0.068(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 Mn1 0.0325(7) 0.0190(6) 0.0330(6) -0.0004(5) 0.0060(5) 0.0024(5) N1 0.025(4) 0.027(3) 0.035(4) -0.006(3) 0.003(3) 0.000(3) C1 0.037(5) 0.032(4) 0.046(5) -0.001(4) -0.002(4) -0.003(4) C2 0.048(5) 0.032(4) 0.046(5) -0.011(4) 0.004(4) 0.009(4) C3 0.034(4) 0.046(5) 0.031(4) -0.001(4) 0.003(3) -0.002(4) C4 0.029(4) 0.031(4) 0.037(4) 0.012(4) 0.000(3) -0.007(3) C5 0.037(5) 0.024(4) 0.044(5) 0.012(3) 0.003(4) 0.002(3) C6 0.048(5) 0.024(4) 0.032(4) 0.004(3) -0.005(4) 0.003(3) C7 0.020(4) 0.026(4) 0.050(5) -0.001(3) 0.014(3) -0.005(3) C8 0.035(5) 0.028(4) 0.043(5) -0.001(3) 0.002(4) -0.001(3) C9 0.038(5) 0.014(4) 0.044(5) 0.009(3) -0.003(4) -0.001(3) N2 0.033(4) 0.017(3) 0.048(4) -0.005(3) 0.006(3) 0.006(3) C10 0.050(5) 0.015(3) 0.037(5) -0.002(3) -0.008(4) 0.003(3) C11 0.039(5) 0.020(4) 0.065(5) -0.010(3) 0.025(4) -0.007(3) C12 0.056(6) 0.024(4) 0.083(7) -0.020(4) 0.019(6) -0.012(4) C13 0.021(4) 0.034(4) 0.071(6) -0.018(4) 0.010(4) 0.003(4) C14 0.039(5) 0.029(4) 0.044(4) -0.008(3) -0.002(4) 0.009(4) N3 0.026(3) 0.026(3) 0.036(3) 0.002(3) 0.003(3) 0.003(3) C15 0.012(4) 0.022(4) 0.065(6) 0.004(3) 0.003(4) 0.004(3) C16 0.044(5) 0.026(4) 0.059(5) 0.004(4) -0.003(4) -0.001(4) C17 0.033(5) 0.027(5) 0.097(7) -0.003(4) 0.004(5) -0.001(3) C18 0.047(6) 0.034(5) 0.066(6) 0.008(4) 0.013(4) 0.002(4) C19 0.045(6) 0.033(4) 0.046(5) -0.001(3) 0.018(4) -0.004(4) N4 0.025(3) 0.020(3) 0.028(3) 0.005(3) 0.005(3) 0.001(2) C20 0.034(5) 0.026(4) 0.034(4) -0.003(3) -0.001(3) -0.009(3) O1 0.057(4) 0.020(3) 0.047(3) -0.003(2) 0.016(3) 0.003(2) N5 0.012(3) 0.028(3) 0.033(3) -0.005(2) 0.005(2) -0.003(2) C21 0.036(5) 0.027(4) 0.034(4) 0.003(3) 0.009(3) 0.003(3) C22 0.025(4) 0.033(4) 0.047(4) -0.005(3) 0.015(4) 0.005(3) C23 0.056(6) 0.019(3) 0.038(4) -0.002(3) 0.001(4) -0.001(3) N6 0.029(3) 0.011(3) 0.045(3) 0.000(2) 0.014(3) -0.001(2) O2 0.085(5) 0.077(5) 0.076(5) 0.007(4) 0.013(4) -0.012(4) N7 0.025(4) 0.059(5) 0.042(4) 0.013(4) 0.009(3) 0.003(3) O3 0.041(3) 0.055(4) 0.060(4) 0.032(3) 0.008(3) 0.004(3) O4 0.039(3) 0.067(4) 0.038(3) 0.005(3) 0.005(2) 0.005(3) Cl1 0.0486(13) 0.0353(11) 0.0413(11) 0.0014(8) 0.0114(10) 0.0037(9) O5 0.087(5) 0.064(4) 0.062(4) -0.029(3) 0.001(4) 0.000(3) O6 0.034(3) 0.068(4) 0.045(3) 0.004(2) 0.012(3) 0.004(2) O7 0.035(3) 0.055(3) 0.061(4) 0.000(3) 0.003(3) 0.007(3) O8 0.095(5) 0.053(3) 0.054(4) 0.013(3) 0.018(3) 0.012(3) C24 0.052(6) 0.047(5) 0.083(7) 0.001(4) 0.023(5) -0.002(4) C25 0.085(8) 0.028(5) 0.051(6) 0.002(4) 0.013(5) 0.012(5) N8 0.084(6) 0.045(4) 0.070(6) 0.009(4) -0.004(5) 0.007(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 Mn1 N6 1.660(5) . ? Mn1 N4 1.957(5) . ? Mn1 N1 2.024(5) . ? Mn1 N5 2.052(5) . ? Mn1 N3 2.061(5) . ? Mn1 N2 2.075(6) . ? N1 C1 1.328(8) . ? N1 C9 1.375(8) . ? C1 C2 1.413(10) . ? C1 H1 0.9500 . ? C2 C3 1.360(9) . ? C2 H2 0.9500 . ? C3 C8 1.415(9) . ? C3 H3 0.9500 . ? C4 C5 1.385(9) . ? C4 C8 1.407(9) . ? C4 N7 1.464(8) . ? C5 C6 1.384(9) . ? C5 H5 0.9500 . ? C6 C7 1.398(8) . ? C6 H6 0.9500 . ? C7 N4 1.382(8) . ? C7 C9 1.434(9) . ? C8 C9 1.420(9) . ? N2 C14 1.339(9) . ? N2 C10 1.357(8) . ? C10 C11 1.391(9) . ? C10 C21 1.514(9) . ? C11 C12 1.343(11) . ? C11 H11 0.9500 . ? C12 C13 1.389(10) . ? C12 H12 0.9500 . ? C13 C14 1.370(10) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N3 C15 1.340(8) . ? N3 C19 1.349(8) . ? C15 C16 1.384(10) . ? C15 C22 1.519(9) . ? C16 C17 1.386(10) . ? C16 H16 0.9500 . ? C17 C18 1.372(10) . ? C17 H17 0.9500 . ? C18 C19 1.386(10) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? N4 C20 1.367(8) . ? C20 O1 1.217(7) . ? C20 C23 1.526(9) . ? N5 C22 1.481(8) . ? N5 C21 1.489(8) . ? N5 C23 1.502(7) . ? C21 H21 0.9900 . ? C21 H21A 0.9900 . ? C22 H22 0.9900 . ? C22 H22A 0.9900 . ? C23 H23 0.9900 . ? C23 H23A 0.9900 . ? N6 O2 1.136(7) . ? N7 O3 1.231(7) . ? N7 O4 1.234(7) . ? Cl1 O8 1.423(4) . ? Cl1 O5 1.424(4) . ? Cl1 O7 1.440(4) . ? Cl1 O6 1.443(4) . ? C24 C25 1.449(13) . ? C24 H24 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C25 N8 1.130(10) . ? 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 N6 Mn1 N4 176.4(2) . . ? N6 Mn1 N1 96.6(2) . . ? N4 Mn1 N1 80.1(2) . . ? N6 Mn1 N5 99.5(2) . . ? N4 Mn1 N5 83.8(2) . . ? N1 Mn1 N5 163.72(18) . . ? N6 Mn1 N3 93.5(2) . . ? N4 Mn1 N3 85.6(2) . . ? N1 Mn1 N3 95.6(2) . . ? N5 Mn1 N3 80.8(2) . . ? N6 Mn1 N2 95.2(2) . . ? N4 Mn1 N2 86.7(2) . . ? N1 Mn1 N2 101.4(2) . . ? N5 Mn1 N2 79.9(2) . . ? N3 Mn1 N2 159.9(2) . . ? C1 N1 C9 119.6(6) . . ? C1 N1 Mn1 126.2(5) . . ? C9 N1 Mn1 114.1(4) . . ? N1 C1 C2 121.3(6) . . ? N1 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C3 C2 C1 119.9(6) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C8 120.3(7) . . ? C2 C3 H3 119.8 . . ? C8 C3 H3 119.8 . . ? C5 C4 C8 122.4(6) . . ? C5 C4 N7 116.6(6) . . ? C8 C4 N7 121.1(6) . . ? C6 C5 C4 121.9(6) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 119.2(6) . . ? C5 C6 H6 120.4 . . ? C7 C6 H6 120.4 . . ? N4 C7 C6 128.7(6) . . ? N4 C7 C9 112.9(5) . . ? C6 C7 C9 118.4(6) . . ? C4 C8 C3 127.9(7) . . ? C4 C8 C9 115.2(6) . . ? C3 C8 C9 116.8(6) . . ? N1 C9 C8 121.8(6) . . ? N1 C9 C7 115.3(6) . . ? C8 C9 C7 122.9(6) . . ? C14 N2 C10 117.3(6) . . ? C14 N2 Mn1 128.9(5) . . ? C10 N2 Mn1 113.8(5) . . ? N2 C10 C11 122.2(6) . . ? N2 C10 C21 114.3(6) . . ? C11 C10 C21 123.4(6) . . ? C12 C11 C10 118.0(8) . . ? C12 C11 H11 121.0 . . ? C10 C11 H11 121.0 . . ? C11 C12 C13 121.7(8) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C12 116.8(7) . . ? C14 C13 H13 121.6 . . ? C12 C13 H13 121.6 . . ? N2 C14 C13 123.9(7) . . ? N2 C14 H14 118.0 . . ? C13 C14 H14 118.0 . . ? C15 N3 C19 117.8(6) . . ? C15 N3 Mn1 113.2(4) . . ? C19 N3 Mn1 128.7(5) . . ? N3 C15 C16 123.3(7) . . ? N3 C15 C22 114.9(6) . . ? C16 C15 C22 121.8(7) . . ? C15 C16 C17 117.9(8) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? C18 C17 C16 119.9(8) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 118.8(7) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? N3 C19 C18 122.4(7) . . ? N3 C19 H19 118.8 . . ? C18 C19 H19 118.8 . . ? C20 N4 C7 123.1(5) . . ? C20 N4 Mn1 119.5(4) . . ? C7 N4 Mn1 117.4(4) . . ? O1 C20 N4 128.2(6) . . ? O1 C20 C23 119.8(6) . . ? N4 C20 C23 112.0(6) . . ? C22 N5 C21 112.8(5) . . ? C22 N5 C23 110.5(5) . . ? C21 N5 C23 110.7(5) . . ? C22 N5 Mn1 106.2(4) . . ? C21 N5 Mn1 107.1(4) . . ? C23 N5 Mn1 109.4(4) . . ? N5 C21 C10 108.8(5) . . ? N5 C21 H21 109.9 . . ? C10 C21 H21 109.9 . . ? N5 C21 H21A 109.9 . . ? C10 C21 H21A 109.9 . . ? H21 C21 H21A 108.3 . . ? N5 C22 C15 108.3(5) . . ? N5 C22 H22 110.0 . . ? C15 C22 H22 110.0 . . ? N5 C22 H22A 110.0 . . ? C15 C22 H22A 110.0 . . ? H22 C22 H22A 108.4 . . ? N5 C23 C20 115.1(5) . . ? N5 C23 H23 108.5 . . ? C20 C23 H23 108.5 . . ? N5 C23 H23A 108.5 . . ? C20 C23 H23A 108.5 . . ? H23 C23 H23A 107.5 . . ? O2 N6 Mn1 175.8(6) . . ? O3 N7 O4 123.4(6) . . ? O3 N7 C4 118.6(6) . . ? O4 N7 C4 118.0(6) . . ? O8 Cl1 O5 110.4(3) . . ? O8 Cl1 O7 109.3(3) . . ? O5 Cl1 O7 109.7(3) . . ? O8 Cl1 O6 109.1(3) . . ? O5 Cl1 O6 109.4(3) . . ? O7 Cl1 O6 108.9(3) . . ? C25 C24 H24 109.5 . . ? C25 C24 H24A 109.5 . . ? H24 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? H24 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N8 C25 C24 178.6(10) . . ? 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 N6 Mn1 N1 C1 2.5(6) . . . . ? N4 Mn1 N1 C1 -176.3(6) . . . . ? N5 Mn1 N1 C1 -167.9(7) . . . . ? N3 Mn1 N1 C1 -91.7(6) . . . . ? N2 Mn1 N1 C1 99.1(6) . . . . ? N6 Mn1 N1 C9 -179.0(5) . . . . ? N4 Mn1 N1 C9 2.2(5) . . . . ? N5 Mn1 N1 C9 10.6(11) . . . . ? N3 Mn1 N1 C9 86.8(5) . . . . ? N2 Mn1 N1 C9 -82.4(5) . . . . ? C9 N1 C1 C2 -3.0(10) . . . . ? Mn1 N1 C1 C2 175.4(5) . . . . ? N1 C1 C2 C3 4.5(11) . . . . ? C1 C2 C3 C8 -1.5(11) . . . . ? C8 C4 C5 C6 1.1(11) . . . . ? N7 C4 C5 C6 -178.3(6) . . . . ? C4 C5 C6 C7 0.0(11) . . . . ? C5 C6 C7 N4 -179.3(6) . . . . ? C5 C6 C7 C9 0.5(10) . . . . ? C5 C4 C8 C3 174.5(7) . . . . ? N7 C4 C8 C3 -6.1(11) . . . . ? C5 C4 C8 C9 -2.5(10) . . . . ? N7 C4 C8 C9 176.9(6) . . . . ? C2 C3 C8 C4 -179.6(7) . . . . ? C2 C3 C8 C9 -2.6(10) . . . . ? C1 N1 C9 C8 -1.4(10) . . . . ? Mn1 N1 C9 C8 -180.0(5) . . . . ? C1 N1 C9 C7 177.3(6) . . . . ? Mn1 N1 C9 C7 -1.3(7) . . . . ? C4 C8 C9 N1 -178.5(6) . . . . ? C3 C8 C9 N1 4.2(10) . . . . ? C4 C8 C9 C7 3.0(10) . . . . ? C3 C8 C9 C7 -174.4(6) . . . . ? N4 C7 C9 N1 -0.9(8) . . . . ? C6 C7 C9 N1 179.3(6) . . . . ? N4 C7 C9 C8 177.7(6) . . . . ? C6 C7 C9 C8 -2.1(10) . . . . ? N6 Mn1 N2 C14 98.1(5) . . . . ? N4 Mn1 N2 C14 -78.8(5) . . . . ? N1 Mn1 N2 C14 0.4(6) . . . . ? N5 Mn1 N2 C14 -163.1(5) . . . . ? N3 Mn1 N2 C14 -146.6(6) . . . . ? N6 Mn1 N2 C10 -81.4(4) . . . . ? N4 Mn1 N2 C10 101.6(4) . . . . ? N1 Mn1 N2 C10 -179.2(4) . . . . ? N5 Mn1 N2 C10 17.3(4) . . . . ? N3 Mn1 N2 C10 33.9(8) . . . . ? C14 N2 C10 C11 0.2(9) . . . . ? Mn1 N2 C10 C11 179.8(5) . . . . ? C14 N2 C10 C21 -176.9(5) . . . . ? Mn1 N2 C10 C21 2.7(6) . . . . ? N2 C10 C11 C12 -2.5(10) . . . . ? C21 C10 C11 C12 174.3(6) . . . . ? C10 C11 C12 C13 3.0(10) . . . . ? C11 C12 C13 C14 -1.2(10) . . . . ? C10 N2 C14 C13 1.7(9) . . . . ? Mn1 N2 C14 C13 -177.8(4) . . . . ? C12 C13 C14 N2 -1.3(10) . . . . ? N6 Mn1 N3 C15 83.9(5) . . . . ? N4 Mn1 N3 C15 -99.6(4) . . . . ? N1 Mn1 N3 C15 -179.2(4) . . . . ? N5 Mn1 N3 C15 -15.2(4) . . . . ? N2 Mn1 N3 C15 -31.7(9) . . . . ? N6 Mn1 N3 C19 -101.7(6) . . . . ? N4 Mn1 N3 C19 74.8(5) . . . . ? N1 Mn1 N3 C19 -4.8(6) . . . . ? N5 Mn1 N3 C19 159.2(6) . . . . ? N2 Mn1 N3 C19 142.7(6) . . . . ? C19 N3 C15 C16 -0.6(10) . . . . ? Mn1 N3 C15 C16 174.4(5) . . . . ? C19 N3 C15 C22 178.8(5) . . . . ? Mn1 N3 C15 C22 -6.1(7) . . . . ? N3 C15 C16 C17 0.8(10) . . . . ? C22 C15 C16 C17 -178.6(6) . . . . ? C15 C16 C17 C18 -1.3(10) . . . . ? C16 C17 C18 C19 1.6(11) . . . . ? C15 N3 C19 C18 1.0(10) . . . . ? Mn1 N3 C19 C18 -173.2(5) . . . . ? C17 C18 C19 N3 -1.5(11) . . . . ? C6 C7 N4 C20 4.9(10) . . . . ? C9 C7 N4 C20 -174.9(6) . . . . ? C6 C7 N4 Mn1 -177.4(6) . . . . ? C9 C7 N4 Mn1 2.9(7) . . . . ? N6 Mn1 N4 C20 155(4) . . . . ? N1 Mn1 N4 C20 175.0(5) . . . . ? N5 Mn1 N4 C20 -2.6(4) . . . . ? N3 Mn1 N4 C20 78.5(5) . . . . ? N2 Mn1 N4 C20 -82.8(5) . . . . ? N6 Mn1 N4 C7 -23(4) . . . . ? N1 Mn1 N4 C7 -2.8(4) . . . . ? N5 Mn1 N4 C7 179.6(5) . . . . ? N3 Mn1 N4 C7 -99.3(4) . . . . ? N2 Mn1 N4 C7 99.3(4) . . . . ? C7 N4 C20 O1 1.5(10) . . . . ? Mn1 N4 C20 O1 -176.2(6) . . . . ? C7 N4 C20 C23 -177.4(5) . . . . ? Mn1 N4 C20 C23 4.9(7) . . . . ? N6 Mn1 N5 C22 -59.8(4) . . . . ? N4 Mn1 N5 C22 118.8(4) . . . . ? N1 Mn1 N5 C22 110.5(9) . . . . ? N3 Mn1 N5 C22 32.2(4) . . . . ? N2 Mn1 N5 C22 -153.5(4) . . . . ? N6 Mn1 N5 C21 61.0(4) . . . . ? N4 Mn1 N5 C21 -120.4(4) . . . . ? N1 Mn1 N5 C21 -128.8(8) . . . . ? N3 Mn1 N5 C21 153.0(4) . . . . ? N2 Mn1 N5 C21 -32.7(4) . . . . ? N6 Mn1 N5 C23 -179.1(4) . . . . ? N4 Mn1 N5 C23 -0.5(4) . . . . ? N1 Mn1 N5 C23 -8.8(11) . . . . ? N3 Mn1 N5 C23 -87.0(4) . . . . ? N2 Mn1 N5 C23 87.3(4) . . . . ? C22 N5 C21 C10 159.1(5) . . . . ? C23 N5 C21 C10 -76.4(6) . . . . ? Mn1 N5 C21 C10 42.7(6) . . . . ? N2 C10 C21 N5 -30.4(7) . . . . ? C11 C10 C21 N5 152.5(6) . . . . ? C21 N5 C22 C15 -160.3(5) . . . . ? C23 N5 C22 C15 75.2(6) . . . . ? Mn1 N5 C22 C15 -43.3(5) . . . . ? N3 C15 C22 N5 33.6(7) . . . . ? C16 C15 C22 N5 -146.9(6) . . . . ? C22 N5 C23 C20 -113.4(6) . . . . ? C21 N5 C23 C20 120.8(6) . . . . ? Mn1 N5 C23 C20 3.1(7) . . . . ? O1 C20 C23 N5 175.8(6) . . . . ? N4 C20 C23 N5 -5.1(8) . . . . ? N4 Mn1 N6 O2 33(11) . . . . ? N1 Mn1 N6 O2 13(8) . . . . ? N5 Mn1 N6 O2 -169(8) . . . . ? N3 Mn1 N6 O2 109(8) . . . . ? N2 Mn1 N6 O2 -89(8) . . . . ? C5 C4 N7 O3 -24.4(9) . . . . ? C8 C4 N7 O3 156.3(6) . . . . ? C5 C4 N7 O4 152.9(6) . . . . ? C8 C4 N7 O4 -26.5(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 54.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.513 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 947312'