Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name _publ_author_address N.Reddig ; Institut fur Anorganische und Analytische Chemie Universitat Munster Wilhelm-Klemm-Strasse 8 48149 Munster Bundesrepublik Deutschland ; D.Pursche ; Institut fur Anorganische und Analytische Chemie Universitat Munster Wilhelm-Klemm-Strasse 8 48149 Munster Bundesrepublik Deutschland ; A.Rompel ; Institut fur Anorganische und Analytische Chemie Universitat Munster Wilhelm-Klemm-Strasse 8 48149 Munster Bundesrepublik Deutschland ; _publ_contact_author_name 'Dr Annette Rompel' _publ_contact_author_address ; Institut fur Anorganische und Analytische Chemie Westfalische Wilhelms-Universitat Wilhelm-Klemm-Str. 8 Munster 48149 GERMANY ; _publ_contact_author_email ROMPELA@UNI-MUENSTER.DE _publ_section_title ; Unique Example of Flexible Phenol Coordination in Mononuclear Manganese Compounds ; #_END OF FILE data_p-1 _database_code_depnum_ccdc_archive 'CCDC 226271' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Manganese(II)-di-chloro-2-((bis(pyridin-2-ylmethyl)amino)methyl)-4-nitrophenol ; _chemical_name_common ;Manganese(ii)-di-chloro-2-((bis(pyridin-2- ylmethyl)amino)methyl)-4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cl2 Mn N4 O4' _chemical_formula_weight 508.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4619(3) _cell_length_b 9.4354(3) _cell_length_c 16.1153(5) _cell_angle_alpha 97.941(2) _cell_angle_beta 92.761(2) _cell_angle_gamma 98.723(2) _cell_volume 1107.96(7) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 0.872 _exptl_absorpt_correction_type 'SADABS software package, Bruker AXS' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS SMART APEX CCD' _diffrn_measurement_method 'combined omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6537 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0615 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.28 _diffrn_reflns_theta_max 25.92 _reflns_number_total 3706 _reflns_number_gt 2905 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART software package, Bruker Nonius' _computing_cell_refinement 'SMART/SAINT software package, Bruker Nonius' _computing_data_reduction 'G. M. Sheldrick, Shelxltl Plus, Siemens Analytical X-ray Instruments 1990' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0977P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3706 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1480 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.001 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 0.39571(8) 0.13191(6) 0.77313(4) 0.0263(2) Uani 1 1 d . . . Cl1 Cl 0.39468(15) -0.02252(11) 0.87691(7) 0.0330(3) Uani 1 1 d . . . Cl2 Cl 0.12232(14) 0.10689(11) 0.68974(7) 0.0306(3) Uani 1 1 d . . . O1 O 0.7920(4) 0.6486(3) 0.84170(19) 0.0319(7) Uani 1 1 d . . . H1A H 0.7999 0.7381 0.8574 0.048 Uiso 1 1 calc R . . O2 O 1.1713(5) 0.4110(3) 0.5296(2) 0.0426(8) Uani 1 1 d . . . O3 O 1.2956(5) 0.6346(4) 0.5442(2) 0.0499(10) Uani 1 1 d . . . N1 N 0.5680(4) 0.3196(3) 0.72167(19) 0.0202(7) Uani 1 1 d . . . N2 N 0.5657(5) 0.0311(4) 0.6782(2) 0.0257(7) Uani 1 1 d . . . N3 N 0.3657(4) 0.3347(4) 0.8575(2) 0.0246(7) Uani 1 1 d . . . N4 N 1.1910(5) 0.5357(4) 0.5660(2) 0.0279(8) Uani 1 1 d . . . C1 C 0.5727(5) 0.2637(4) 0.6319(2) 0.0240(8) Uani 1 1 d . . . H1B H 0.6625 0.3297 0.6062 0.029 Uiso 1 1 calc R . . H1C H 0.4519 0.2609 0.6029 0.029 Uiso 1 1 calc R . . C2 C 0.6225(5) 0.1147(4) 0.6203(2) 0.0225(8) Uani 1 1 d . . . C3 C 0.5993(6) -0.1060(5) 0.6683(3) 0.0329(10) Uani 1 1 d . . . H3A H 0.5587 -0.1653 0.7089 0.039 Uiso 1 1 calc R . . C4 C 0.6887(6) -0.1655(5) 0.6031(3) 0.0349(10) Uani 1 1 d . . . H4A H 0.7086 -0.2633 0.5983 0.042 Uiso 1 1 calc R . . C5 C 0.7489(6) -0.0777(5) 0.5446(3) 0.0344(10) Uani 1 1 d . . . H5A H 0.8116 -0.1146 0.4985 0.041 Uiso 1 1 calc R . . C6 C 0.7169(6) 0.0639(5) 0.5538(3) 0.0294(9) Uani 1 1 d . . . H6A H 0.7595 0.1258 0.5148 0.035 Uiso 1 1 calc R . . C7 C 0.4612(5) 0.4389(4) 0.7348(2) 0.0217(8) Uani 1 1 d . . . H7A H 0.3564 0.4200 0.6925 0.026 Uiso 1 1 calc R . . H7B H 0.5377 0.5306 0.7268 0.026 Uiso 1 1 calc R . . C8 C 0.3931(5) 0.4550(4) 0.8214(2) 0.0232(8) Uani 1 1 d . . . C9 C 0.2967(6) 0.3420(5) 0.9331(3) 0.0312(9) Uani 1 1 d . . . H9A H 0.2807 0.2575 0.9596 0.037 Uiso 1 1 calc R . . C10 C 0.2482(7) 0.4679(5) 0.9740(3) 0.0379(11) Uani 1 1 d . . . H10A H 0.1976 0.4697 1.0271 0.045 Uiso 1 1 calc R . . C11 C 0.2753(7) 0.5910(5) 0.9356(3) 0.0405(11) Uani 1 1 d . . . H11A H 0.2417 0.6787 0.9619 0.049 Uiso 1 1 calc R . . C12 C 0.3510(6) 0.5864(5) 0.8594(3) 0.0315(10) Uani 1 1 d . . . H12A H 0.3741 0.6710 0.8332 0.038 Uiso 1 1 calc R . . C13 C 0.7549(5) 0.3585(4) 0.7653(2) 0.0202(8) Uani 1 1 d . . . H13A H 0.8152 0.2715 0.7583 0.024 Uiso 1 1 calc R . . H13B H 0.7431 0.3857 0.8261 0.024 Uiso 1 1 calc R . . C14 C 0.8752(5) 0.4804(4) 0.7343(2) 0.0197(8) Uani 1 1 d . . . C15 C 0.8896(5) 0.6256(4) 0.7741(2) 0.0224(8) Uani 1 1 d . . . C16 C 0.9989(6) 0.7382(4) 0.7435(2) 0.0253(8) Uani 1 1 d . . . H16A H 1.0056 0.8351 0.7705 0.030 Uiso 1 1 calc R . . C17 C 1.0954(5) 0.7099(4) 0.6754(3) 0.0261(9) Uani 1 1 d . . . H17A H 1.1681 0.7865 0.6540 0.031 Uiso 1 1 calc R . . C18 C 1.0863(5) 0.5676(4) 0.6375(2) 0.0219(8) Uani 1 1 d . . . C19 C 0.9787(5) 0.4536(4) 0.6668(2) 0.0215(8) Uani 1 1 d . . . H19A H 0.9766 0.3569 0.6403 0.026 Uiso 1 1 calc R . . O4 O 0.7840(4) 0.9137(3) 0.9098(2) 0.0421(8) Uani 1 1 d . . . H4 H 0.6749 0.9261 0.9083 0.063 Uiso 1 1 calc R . . C20 C 0.8973(8) 1.0470(6) 0.9068(4) 0.0548(14) Uani 1 1 d . . . H20A H 0.8821 1.1165 0.9561 0.082 Uiso 1 1 calc R . . H20B H 0.8640 1.0850 0.8556 0.082 Uiso 1 1 calc R . . H20C H 1.0244 1.0319 0.9067 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0271(4) 0.0234(4) 0.0284(4) 0.0044(2) 0.0031(3) 0.0032(3) Cl1 0.0353(6) 0.0308(6) 0.0373(6) 0.0144(4) 0.0053(5) 0.0103(5) Cl2 0.0262(5) 0.0274(5) 0.0368(6) 0.0067(4) -0.0066(4) 0.0011(4) O1 0.0387(17) 0.0229(15) 0.0324(16) -0.0020(12) 0.0157(14) 0.0011(13) O2 0.056(2) 0.0359(19) 0.0377(19) 0.0014(14) 0.0196(17) 0.0115(17) O3 0.056(2) 0.052(2) 0.039(2) 0.0102(16) 0.0277(18) -0.0080(18) N1 0.0210(16) 0.0201(16) 0.0189(15) 0.0018(12) -0.0002(13) 0.0029(13) N2 0.0262(18) 0.0232(17) 0.0270(18) -0.0004(13) 0.0037(15) 0.0045(14) N3 0.0229(17) 0.0242(17) 0.0251(17) 0.0008(13) 0.0027(14) 0.0012(14) N4 0.0274(18) 0.035(2) 0.0233(17) 0.0078(15) 0.0049(15) 0.0070(16) C1 0.025(2) 0.026(2) 0.0210(19) 0.0038(15) 0.0025(16) 0.0049(17) C2 0.0196(18) 0.025(2) 0.0212(19) -0.0014(15) 0.0008(15) 0.0011(16) C3 0.031(2) 0.029(2) 0.038(2) 0.0027(18) 0.001(2) 0.0055(19) C4 0.034(2) 0.027(2) 0.040(3) -0.0098(19) -0.004(2) 0.0092(19) C5 0.025(2) 0.044(3) 0.029(2) -0.0111(19) -0.0016(18) 0.008(2) C6 0.026(2) 0.037(2) 0.023(2) -0.0018(17) -0.0003(17) 0.0051(19) C7 0.0222(19) 0.0172(19) 0.027(2) 0.0069(15) 0.0013(16) 0.0048(16) C8 0.0208(19) 0.021(2) 0.028(2) 0.0038(15) -0.0009(16) 0.0035(16) C9 0.034(2) 0.033(2) 0.026(2) 0.0061(17) 0.0092(18) 0.0030(19) C10 0.041(3) 0.042(3) 0.028(2) -0.0048(19) 0.008(2) 0.007(2) C11 0.052(3) 0.031(2) 0.040(3) -0.003(2) 0.012(2) 0.013(2) C12 0.035(2) 0.023(2) 0.039(2) 0.0050(17) 0.009(2) 0.0101(19) C13 0.0210(19) 0.0207(19) 0.0199(19) 0.0047(14) 0.0022(16) 0.0046(16) C14 0.0199(18) 0.0177(18) 0.0219(19) 0.0054(14) 0.0007(15) 0.0024(15) C15 0.0197(19) 0.024(2) 0.0226(19) 0.0006(15) 0.0004(16) 0.0031(16) C16 0.029(2) 0.0184(19) 0.027(2) 0.0016(15) 0.0031(17) 0.0004(17) C17 0.024(2) 0.023(2) 0.031(2) 0.0097(16) -0.0003(17) -0.0017(17) C18 0.0214(19) 0.028(2) 0.0176(18) 0.0057(15) 0.0024(15) 0.0041(16) C19 0.0229(19) 0.0206(19) 0.0209(19) 0.0018(14) -0.0003(16) 0.0048(16) O4 0.0304(17) 0.0300(17) 0.062(2) -0.0073(15) 0.0055(17) 0.0054(14) C20 0.048(3) 0.040(3) 0.072(4) 0.000(3) 0.007(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N3 2.236(3) . ? Mn1 N2 2.237(3) . ? Mn1 N1 2.301(3) . ? Mn1 Cl2 2.3505(12) . ? Mn1 Cl1 2.3648(11) . ? O1 C15 1.351(5) . ? O2 N4 1.225(5) . ? O3 N4 1.225(5) . ? N1 C7 1.474(5) . ? N1 C1 1.474(5) . ? N1 C13 1.501(5) . ? N2 C3 1.344(5) . ? N2 C2 1.346(5) . ? N3 C8 1.339(5) . ? N3 C9 1.342(5) . ? N4 C18 1.446(5) . ? C1 C2 1.497(5) . ? C2 C6 1.381(6) . ? C3 C4 1.371(6) . ? C4 C5 1.387(7) . ? C5 C6 1.382(6) . ? C7 C8 1.504(5) . ? C8 C12 1.392(5) . ? C9 C10 1.383(6) . ? C10 C11 1.383(7) . ? C11 C12 1.375(7) . ? C13 C14 1.505(5) . ? C14 C19 1.381(5) . ? C14 C15 1.416(5) . ? C15 C16 1.399(5) . ? C16 C17 1.360(6) . ? C17 C18 1.386(5) . ? C18 C19 1.393(5) . ? O4 C20 1.413(6) . ? 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 N3 Mn1 N2 145.07(13) . . ? N3 Mn1 N1 73.61(12) . . ? N2 Mn1 N1 73.39(12) . . ? N3 Mn1 Cl2 97.87(9) . . ? N2 Mn1 Cl2 99.32(9) . . ? N1 Mn1 Cl2 100.97(8) . . ? N3 Mn1 Cl1 97.69(9) . . ? N2 Mn1 Cl1 101.94(9) . . ? N1 Mn1 Cl1 143.45(9) . . ? Cl2 Mn1 Cl1 115.48(4) . . ? C7 N1 C1 112.0(3) . . ? C7 N1 C13 112.6(3) . . ? C1 N1 C13 112.1(3) . . ? C7 N1 Mn1 104.0(2) . . ? C1 N1 Mn1 103.4(2) . . ? C13 N1 Mn1 112.1(2) . . ? C3 N2 C2 117.9(4) . . ? C3 N2 Mn1 127.1(3) . . ? C2 N2 Mn1 114.7(3) . . ? C8 N3 C9 118.6(4) . . ? C8 N3 Mn1 114.3(3) . . ? C9 N3 Mn1 126.1(3) . . ? O2 N4 O3 122.6(4) . . ? O2 N4 C18 118.7(3) . . ? O3 N4 C18 118.6(4) . . ? N1 C1 C2 111.1(3) . . ? N2 C2 C6 121.7(4) . . ? N2 C2 C1 115.6(3) . . ? C6 C2 C1 122.7(4) . . ? N2 C3 C4 124.0(4) . . ? C3 C4 C5 117.5(4) . . ? C6 C5 C4 119.4(4) . . ? C2 C6 C5 119.4(4) . . ? N1 C7 C8 111.5(3) . . ? N3 C8 C12 122.2(4) . . ? N3 C8 C7 116.4(3) . . ? C12 C8 C7 121.3(4) . . ? N3 C9 C10 122.6(4) . . ? C11 C10 C9 118.2(4) . . ? C12 C11 C10 119.9(4) . . ? C11 C12 C8 118.4(4) . . ? N1 C13 C14 114.8(3) . . ? C19 C14 C15 117.6(3) . . ? C19 C14 C13 120.8(3) . . ? C15 C14 C13 121.5(3) . . ? O1 C15 C16 122.5(3) . . ? O1 C15 C14 116.6(3) . . ? C16 C15 C14 120.9(3) . . ? C17 C16 C15 120.5(4) . . ? C16 C17 C18 119.0(4) . . ? C17 C18 C19 121.6(4) . . ? C17 C18 N4 119.6(3) . . ? C19 C18 N4 118.8(4) . . ? C14 C19 C18 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.857 _diffrn_reflns_theta_full 25.92 _diffrn_measured_fraction_theta_full 0.857 _refine_diff_density_max 0.640 _refine_diff_density_min -0.637 _refine_diff_density_rms 0.111 #_END OF FILE #_END OF FILE data_p21c_b _database_code_depnum_ccdc_archive 'CCDC 226272' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Manganese(III)-di-chloro-2-((bis(pyridin-2-ylmethyl)amino)methyl)-4-nitrophenol ; _chemical_name_common ;Manganese(iii)-di-chloro-2-((bis(pyridin-2- ylmethyl)amino)methyl)-4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 Cl2 Mn N4 O3' _chemical_formula_weight 475.21 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 P2(1)/c 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 20.623(4) _cell_length_b 7.902(2) _cell_length_c 12.378(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.70(3) _cell_angle_gamma 90.00 _cell_volume 1993.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rod shaped' _exptl_crystal_colour brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 8.105 _exptl_absorpt_correction_type 'SADABS software package, Bruker AXS' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Goebel mirrow' _diffrn_measurement_device_type 'Bruker AXS SMART 6000 CCD' _diffrn_measurement_method 'combined omega theta-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11214 _diffrn_reflns_av_R_equivalents 0.0945 _diffrn_reflns_av_sigmaI/netI 0.0690 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 71.65 _reflns_number_total 3758 _reflns_number_gt 3061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART software package, Bruker Nonius' _computing_cell_refinement 'SMART/SAINT software package, Bruker Nonius' _computing_data_reduction 'G. M. Sheldrick, Shelxltl Plus, Siemens Analytical X-ray Instruments 1990' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1051P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3758 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1546 _refine_ls_wR_factor_gt 0.1498 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.19568(2) 0.47858(7) 0.94724(4) 0.01950(19) Uani 1 1 d . . . Cl1 Cl 0.09898(4) 0.30870(11) 0.97667(7) 0.0297(2) Uani 1 1 d . . . Cl2 Cl 0.20383(4) 0.63631(11) 1.10349(7) 0.0269(2) Uani 1 1 d . . . O1 O 0.25416(11) 0.3100(3) 1.00903(19) 0.0243(5) Uani 1 1 d . . . O2 O 0.49677(13) -0.0052(4) 0.8396(2) 0.0435(8) Uani 1 1 d . . . O3 O 0.42463(14) -0.0318(4) 0.6951(2) 0.0417(8) Uani 1 1 d . . . N1 N 0.19581(14) 0.3839(4) 0.7877(2) 0.0214(6) Uani 1 1 d . . . N2 N 0.13397(13) 0.6444(4) 0.8547(2) 0.0236(6) Uani 1 1 d . . . N3 N 0.28705(14) 0.6026(4) 0.8994(2) 0.0233(6) Uani 1 1 d . . . N4 N 0.44027(15) 0.0110(4) 0.7904(3) 0.0316(8) Uani 1 1 d . . . C1 C 0.12709(16) 0.4099(5) 0.7300(3) 0.0238(7) Uani 1 1 d . . . H1A H 0.1255 0.3953 0.6502 0.029 Uiso 1 1 calc R . . H1B H 0.0972 0.3262 0.7559 0.029 Uiso 1 1 calc R . . C2 C 0.10669(16) 0.5857(5) 0.7548(3) 0.0221(7) Uani 1 1 d . . . C3 C 0.11822(16) 0.8020(5) 0.8841(3) 0.0271(8) Uani 1 1 d . . . H3 H 0.1372 0.8438 0.9537 0.033 Uiso 1 1 calc R . . C4 C 0.07547(17) 0.9047(5) 0.8168(3) 0.0298(8) Uani 1 1 d . . . H4 H 0.0652 1.0149 0.8398 0.036 Uiso 1 1 calc R . . C5 C 0.04785(17) 0.8443(5) 0.7152(3) 0.0309(9) Uani 1 1 d . . . H5 H 0.0183 0.9125 0.6674 0.037 Uiso 1 1 calc R . . C6 C 0.06390(16) 0.6827(5) 0.6843(3) 0.0268(8) Uani 1 1 d . . . H6 H 0.0455 0.6393 0.6148 0.032 Uiso 1 1 calc R . . C7 C 0.24270(17) 0.4753(5) 0.7277(3) 0.0245(8) Uani 1 1 d . . . H7A H 0.2196 0.5701 0.6860 0.029 Uiso 1 1 calc R . . H7B H 0.2584 0.3971 0.6748 0.029 Uiso 1 1 calc R . . C8 C 0.30061(17) 0.5435(4) 0.8035(3) 0.0223(7) Uani 1 1 d . . . C9 C 0.33571(18) 0.6694(5) 0.9699(3) 0.0292(8) Uani 1 1 d . . . H9 H 0.3259 0.7116 1.0375 0.035 Uiso 1 1 calc R . . C10 C 0.39963(18) 0.6801(5) 0.9492(3) 0.0333(9) Uani 1 1 d . . . H10 H 0.4330 0.7285 1.0015 0.040 Uiso 1 1 calc R . . C11 C 0.41382(19) 0.6191(5) 0.8513(4) 0.0359(9) Uani 1 1 d . . . H11 H 0.4574 0.6242 0.8350 0.043 Uiso 1 1 calc R . . C12 C 0.36380(19) 0.5501(5) 0.7764(3) 0.0308(8) Uani 1 1 d . . . H12 H 0.3725 0.5082 0.7080 0.037 Uiso 1 1 calc R . . C13 C 0.21069(16) 0.1982(4) 0.7942(3) 0.0221(7) Uani 1 1 d . . . H13A H 0.2051 0.1491 0.7198 0.027 Uiso 1 1 calc R . . H13B H 0.1800 0.1401 0.8362 0.027 Uiso 1 1 calc R . . C14 C 0.28046(17) 0.1729(4) 0.8498(3) 0.0225(7) Uani 1 1 d . . . C15 C 0.29806(17) 0.2343(4) 0.9565(3) 0.0218(7) Uani 1 1 d . . . C16 C 0.36303(17) 0.2172(5) 1.0083(3) 0.0268(8) Uani 1 1 d . . . H16 H 0.3751 0.2568 1.0810 0.032 Uiso 1 1 calc R . . C17 C 0.40962(18) 0.1432(5) 0.9546(3) 0.0280(8) Uani 1 1 d . . . H17 H 0.4537 0.1315 0.9897 0.034 Uiso 1 1 calc R . . C18 C 0.39109(17) 0.0861(5) 0.8485(3) 0.0244(8) Uani 1 1 d . . . C19 C 0.32682(17) 0.0987(4) 0.7958(3) 0.0227(7) Uani 1 1 d . . . H19 H 0.3150 0.0567 0.7236 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0205(3) 0.0212(3) 0.0164(3) -0.0008(2) 0.0017(2) 0.0018(2) Cl1 0.0279(4) 0.0352(5) 0.0254(4) 0.0039(4) 0.0020(4) -0.0054(4) Cl2 0.0315(4) 0.0271(4) 0.0223(4) -0.0051(4) 0.0048(4) 0.0007(3) O1 0.0272(12) 0.0274(13) 0.0187(12) 0.0028(11) 0.0048(10) 0.0058(10) O2 0.0247(14) 0.073(2) 0.0336(16) 0.0104(15) 0.0058(13) 0.0152(13) O3 0.0358(15) 0.065(2) 0.0248(15) -0.0037(14) 0.0059(13) 0.0150(14) N1 0.0214(13) 0.0218(15) 0.0215(14) 0.0020(12) 0.0042(12) 0.0028(11) N2 0.0187(13) 0.0265(15) 0.0255(15) 0.0009(13) 0.0030(13) 0.0014(11) N3 0.0235(14) 0.0213(15) 0.0245(15) -0.0008(13) 0.0023(13) 0.0022(12) N4 0.0265(16) 0.041(2) 0.0286(18) 0.0097(15) 0.0089(14) 0.0081(14) C1 0.0225(16) 0.0284(18) 0.0191(16) -0.0025(15) -0.0008(14) 0.0015(14) C2 0.0181(15) 0.0264(17) 0.0221(17) 0.0033(15) 0.0038(14) -0.0005(14) C3 0.0233(17) 0.0287(19) 0.0296(19) -0.0030(17) 0.0048(16) 0.0035(15) C4 0.0227(17) 0.0243(18) 0.043(2) 0.0029(18) 0.0064(17) 0.0008(15) C5 0.0192(16) 0.0299(19) 0.043(2) 0.0099(18) 0.0026(17) 0.0022(14) C6 0.0172(15) 0.0318(19) 0.0312(19) 0.0060(17) 0.0035(15) -0.0029(14) C7 0.0268(18) 0.0277(18) 0.0193(17) 0.0041(15) 0.0047(15) 0.0019(14) C8 0.0257(17) 0.0196(17) 0.0227(17) 0.0028(15) 0.0070(15) 0.0025(14) C9 0.0327(19) 0.029(2) 0.0259(18) -0.0011(17) 0.0048(17) -0.0052(16) C10 0.0236(18) 0.040(2) 0.036(2) -0.0037(19) 0.0045(17) -0.0083(16) C11 0.0258(18) 0.038(2) 0.045(2) 0.002(2) 0.0109(19) -0.0038(16) C12 0.0323(19) 0.030(2) 0.032(2) 0.0009(18) 0.0125(17) -0.0005(16) C13 0.0222(16) 0.0213(17) 0.0225(17) -0.0047(15) 0.0024(14) 0.0044(13) C14 0.0256(17) 0.0193(17) 0.0222(17) 0.0043(15) 0.0022(15) 0.0016(13) C15 0.0283(17) 0.0164(16) 0.0213(17) 0.0024(14) 0.0058(15) 0.0007(14) C16 0.0304(18) 0.031(2) 0.0188(16) 0.0007(16) 0.0029(15) -0.0005(16) C17 0.0244(17) 0.033(2) 0.0252(18) 0.0056(16) -0.0022(16) 0.0003(15) C18 0.0258(17) 0.0255(17) 0.0226(17) 0.0084(16) 0.0055(15) 0.0061(15) C19 0.0274(17) 0.0235(17) 0.0171(16) 0.0014(15) 0.0031(15) 0.0003(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 1.880(2) . ? Mn1 N2 2.051(3) . ? Mn1 N1 2.112(3) . ? Mn1 N3 2.280(3) . ? Mn1 Cl2 2.2856(10) . ? Mn1 Cl1 2.4762(11) . ? O1 C15 1.333(4) . ? O2 N4 1.237(4) . ? O3 N4 1.223(4) . ? N1 C7 1.492(4) . ? N1 C13 1.499(4) . ? N1 C1 1.501(4) . ? N2 C3 1.351(4) . ? N2 C2 1.360(5) . ? N3 C9 1.335(5) . ? N3 C8 1.344(4) . ? N4 C18 1.455(5) . ? C1 C2 1.497(5) . ? C2 C6 1.377(5) . ? C3 C4 1.381(5) . ? C4 C5 1.384(6) . ? C5 C6 1.387(5) . ? C7 C8 1.503(5) . ? C8 C12 1.395(5) . ? C9 C10 1.383(5) . ? C10 C11 1.377(6) . ? C11 C12 1.390(6) . ? C13 C14 1.511(4) . ? C14 C19 1.377(5) . ? C14 C15 1.403(5) . ? C15 C16 1.402(5) . ? C16 C17 1.378(5) . ? C17 C18 1.387(5) . ? C18 C19 1.389(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 N2 170.20(11) . . ? O1 Mn1 N1 92.17(11) . . ? N2 Mn1 N1 78.05(11) . . ? O1 Mn1 N3 84.58(11) . . ? N2 Mn1 N3 92.75(11) . . ? N1 Mn1 N3 77.96(11) . . ? O1 Mn1 Cl2 94.68(8) . . ? N2 Mn1 Cl2 94.82(9) . . ? N1 Mn1 Cl2 166.91(9) . . ? N3 Mn1 Cl2 91.58(8) . . ? O1 Mn1 Cl1 92.14(8) . . ? N2 Mn1 Cl1 89.02(8) . . ? N1 Mn1 Cl1 93.46(8) . . ? N3 Mn1 Cl1 170.66(8) . . ? Cl2 Mn1 Cl1 97.41(4) . . ? C15 O1 Mn1 124.1(2) . . ? C7 N1 C13 111.0(3) . . ? C7 N1 C1 109.5(3) . . ? C13 N1 C1 109.3(3) . . ? C7 N1 Mn1 112.7(2) . . ? C13 N1 Mn1 109.0(2) . . ? C1 N1 Mn1 105.2(2) . . ? C3 N2 C2 118.4(3) . . ? C3 N2 Mn1 126.4(2) . . ? C2 N2 Mn1 115.2(2) . . ? C9 N3 C8 118.6(3) . . ? C9 N3 Mn1 124.7(2) . . ? C8 N3 Mn1 111.8(2) . . ? O3 N4 O2 122.5(3) . . ? O3 N4 C18 119.1(3) . . ? O2 N4 C18 118.3(3) . . ? C2 C1 N1 107.7(3) . . ? N2 C2 C6 121.6(3) . . ? N2 C2 C1 114.4(3) . . ? C6 C2 C1 124.0(3) . . ? N2 C3 C4 122.4(4) . . ? C3 C4 C5 118.9(4) . . ? C4 C5 C6 119.1(3) . . ? C2 C6 C5 119.6(4) . . ? N1 C7 C8 112.1(3) . . ? N3 C8 C12 121.8(3) . . ? N3 C8 C7 115.1(3) . . ? C12 C8 C7 123.1(3) . . ? N3 C9 C10 123.1(4) . . ? C11 C10 C9 118.5(4) . . ? C10 C11 C12 119.3(4) . . ? C11 C12 C8 118.7(4) . . ? N1 C13 C14 109.1(3) . . ? C19 C14 C15 120.3(3) . . ? C19 C14 C13 121.2(3) . . ? C15 C14 C13 118.4(3) . . ? O1 C15 C16 119.6(3) . . ? O1 C15 C14 121.1(3) . . ? C16 C15 C14 119.4(3) . . ? C17 C16 C15 120.6(3) . . ? C16 C17 C18 118.8(3) . . ? C17 C18 C19 121.8(3) . . ? C17 C18 N4 119.2(3) . . ? C19 C18 N4 119.0(3) . . ? C14 C19 C18 119.1(3) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 71.65 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.748 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.122 data_p212121 _database_code_depnum_ccdc_archive 'CCDC 226273' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Manganese(III)-tetrachlorocatechol-2-((bis(pyridin-2-ylmethyl)amino)methyl) -4-nitrophenol ; _chemical_name_common ; Manganese(iii)-tetrachlorocatechol-2-((bis(pyridin-2- ylmethyl)amino)methyl) -4-nitrophenol ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 Cl4 Mn N4 O5' _chemical_formula_weight 650.17 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.4866(3) _cell_length_b 13.9788(4) _cell_length_c 14.9053(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2601.69(12) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour 'reddish brown' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 8.307 _exptl_absorpt_correction_type 'SADABS software package, Bruker AXS' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Goebel mirrow' _diffrn_measurement_device_type 'Bruker AXS SMART 6000 CCD' _diffrn_measurement_method 'combined omega theta-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15421 _diffrn_reflns_av_R_equivalents 0.1055 _diffrn_reflns_av_sigmaI/netI 0.0759 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.34 _diffrn_reflns_theta_max 71.85 _reflns_number_total 4854 _reflns_number_gt 4175 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART software package, Bruker Nonius' _computing_cell_refinement 'SMART/SAINT software package, Bruker Nonius' _computing_data_reduction 'G. M. Sheldrick, Shelxltl Plus, Siemens Analytical X-ray Instruments 1990' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0920P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(7) _refine_ls_number_reflns 4854 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1468 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _refine_ls_shift/su_max 0.004 _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 0.13179(6) 0.58357(5) 0.20956(5) 0.02449(18) Uani 1 1 d . . . Cl1 Cl 0.31303(15) 0.79075(12) 0.42369(11) 0.0631(5) Uani 1 1 d . . . Cl2 Cl 0.56372(16) 0.76115(13) 0.41582(16) 0.0792(7) Uani 1 1 d . . . Cl3 Cl 0.66056(12) 0.62795(15) 0.26688(16) 0.0766(6) Uani 1 1 d . . . Cl4 Cl 0.50712(12) 0.50179(12) 0.15011(12) 0.0596(4) Uani 1 1 d . . . O1 O -0.0036(3) 0.6238(2) 0.2468(2) 0.0296(7) Uani 1 1 d . . . O2 O 0.1966(3) 0.6800(2) 0.2831(2) 0.0311(7) Uani 1 1 d . . . O3 O 0.2733(3) 0.5519(2) 0.1763(2) 0.0313(7) Uani 1 1 d . . . O4 O -0.3211(4) 0.3972(3) 0.4892(3) 0.0518(11) Uani 1 1 d . . . O5 O -0.3172(3) 0.3045(3) 0.3739(3) 0.0485(10) Uani 1 1 d . . . N1 N 0.0646(3) 0.4529(3) 0.1475(3) 0.0301(9) Uani 1 1 d . . . N2 N 0.0977(3) 0.6248(3) 0.0682(3) 0.0312(9) Uani 1 1 d . . . N3 N 0.1399(3) 0.4751(3) 0.3173(3) 0.0304(9) Uani 1 1 d . . . N4 N -0.2871(4) 0.3757(3) 0.4144(3) 0.0374(10) Uani 1 1 d . . . C1 C 0.0967(4) 0.4527(4) 0.0514(3) 0.0367(12) Uani 1 1 d . . . H1A H 0.0510 0.4073 0.0178 0.044 Uiso 1 1 calc R . . H1B H 0.1719 0.4309 0.0461 0.044 Uiso 1 1 calc R . . C2 C 0.0861(4) 0.5503(4) 0.0116(3) 0.0343(11) Uani 1 1 d . . . C3 C 0.0947(4) 0.7119(4) 0.0345(4) 0.0373(12) Uani 1 1 d . . . H3A H 0.1015 0.7645 0.0745 0.045 Uiso 1 1 calc R . . C4 C 0.0819(5) 0.7310(5) -0.0571(4) 0.0475(15) Uani 1 1 d . . . H4A H 0.0814 0.7949 -0.0789 0.057 Uiso 1 1 calc R . . C5 C 0.0702(5) 0.6555(5) -0.1142(4) 0.0509(16) Uani 1 1 d . . . H5A H 0.0624 0.6661 -0.1768 0.061 Uiso 1 1 calc R . . C6 C 0.0699(5) 0.5634(5) -0.0806(4) 0.0457(14) Uani 1 1 d . . . H6A H 0.0589 0.5101 -0.1191 0.055 Uiso 1 1 calc R . . C7 C 0.1097(4) 0.3673(3) 0.1932(3) 0.0358(11) Uani 1 1 d . . . H7A H 0.1802 0.3515 0.1666 0.043 Uiso 1 1 calc R . . H7B H 0.0615 0.3120 0.1836 0.043 Uiso 1 1 calc R . . C8 C 0.1229(4) 0.3842(3) 0.2921(3) 0.0313(10) Uani 1 1 d . . . C9 C 0.1551(4) 0.4949(4) 0.4046(3) 0.0366(11) Uani 1 1 d . . . H9A H 0.1650 0.5594 0.4226 0.044 Uiso 1 1 calc R . . C10 C 0.1566(4) 0.4239(5) 0.4687(4) 0.0445(14) Uani 1 1 d . . . H10A H 0.1683 0.4394 0.5299 0.053 Uiso 1 1 calc R . . C11 C 0.1411(5) 0.3313(5) 0.4434(4) 0.0484(15) Uani 1 1 d . . . H11A H 0.1419 0.2818 0.4871 0.058 Uiso 1 1 calc R . . C12 C 0.1242(4) 0.3096(4) 0.3542(4) 0.0418(12) Uani 1 1 d . . . H12A H 0.1137 0.2453 0.3355 0.050 Uiso 1 1 calc R . . C13 C -0.0561(4) 0.4561(4) 0.1522(3) 0.0314(10) Uani 1 1 d . . . H13A H -0.0851 0.3942 0.1311 0.038 Uiso 1 1 calc R . . H13B H -0.0824 0.5065 0.1110 0.038 Uiso 1 1 calc R . . C14 C -0.0987(4) 0.4759(3) 0.2454(3) 0.0283(10) Uani 1 1 d . . . C15 C -0.0686(3) 0.5611(3) 0.2883(3) 0.0267(9) Uani 1 1 d . . . C16 C -0.1080(4) 0.5823(4) 0.3747(3) 0.0330(10) Uani 1 1 d . . . H16A H -0.0865 0.6395 0.4039 0.040 Uiso 1 1 calc R . . C17 C -0.1774(4) 0.5203(3) 0.4170(3) 0.0327(11) Uani 1 1 d . . . H17A H -0.2032 0.5338 0.4756 0.039 Uiso 1 1 calc R . . C18 C -0.2088(4) 0.4383(3) 0.3725(3) 0.0272(10) Uani 1 1 d . . . C19 C -0.1691(4) 0.4143(3) 0.2878(3) 0.0294(9) Uani 1 1 d . . . H19A H -0.1903 0.3563 0.2596 0.035 Uiso 1 1 calc R . . C20 C 0.3033(4) 0.6686(3) 0.2856(3) 0.0300(10) Uani 1 1 d . . . C21 C 0.3703(5) 0.7163(4) 0.3448(4) 0.0407(12) Uani 1 1 d . . . C22 C 0.4814(5) 0.7028(4) 0.3408(5) 0.0509(16) Uani 1 1 d . . . C23 C 0.5237(4) 0.6424(4) 0.2775(5) 0.0473(15) Uani 1 1 d . . . C24 C 0.4564(4) 0.5877(4) 0.2204(4) 0.0391(11) Uani 1 1 d . . . C25 C 0.3460(4) 0.6003(3) 0.2259(3) 0.0302(10) 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 0.0296(4) 0.0205(3) 0.0234(3) -0.0023(3) 0.0010(3) -0.0014(3) Cl1 0.0791(11) 0.0471(9) 0.0630(10) -0.0255(8) -0.0282(9) 0.0017(7) Cl2 0.0717(12) 0.0590(11) 0.1070(16) 0.0022(10) -0.0537(12) -0.0171(8) Cl3 0.0313(8) 0.0817(12) 0.1168(16) 0.0359(12) -0.0158(9) 0.0026(7) Cl4 0.0447(8) 0.0649(10) 0.0693(10) 0.0014(8) 0.0095(7) 0.0205(7) O1 0.0337(17) 0.0193(16) 0.0359(18) 0.0005(13) 0.0072(14) 0.0011(12) O2 0.0368(18) 0.0236(17) 0.0329(17) -0.0042(14) -0.0033(15) -0.0054(13) O3 0.0305(18) 0.0341(19) 0.0292(16) -0.0047(14) 0.0026(14) 0.0043(13) O4 0.062(3) 0.048(3) 0.045(2) -0.0028(19) 0.023(2) -0.0101(19) O5 0.057(3) 0.038(2) 0.051(2) -0.0034(18) 0.020(2) -0.0160(18) N1 0.034(2) 0.035(2) 0.0218(18) 0.0033(16) 0.0049(17) 0.0006(16) N2 0.031(2) 0.028(2) 0.035(2) 0.0018(17) -0.0002(17) -0.0037(15) N3 0.031(2) 0.031(2) 0.0295(19) -0.0025(16) 0.0003(17) 0.0011(16) N4 0.042(2) 0.031(2) 0.039(2) 0.0078(19) 0.009(2) -0.0015(18) C1 0.045(3) 0.044(3) 0.021(2) -0.009(2) 0.006(2) -0.004(2) C2 0.033(3) 0.043(3) 0.027(2) 0.003(2) 0.005(2) -0.003(2) C3 0.036(3) 0.035(3) 0.041(3) 0.001(2) 0.001(2) -0.001(2) C4 0.044(3) 0.056(4) 0.043(3) 0.021(3) 0.006(3) 0.001(3) C5 0.049(4) 0.073(5) 0.031(3) 0.013(3) 0.002(3) -0.005(3) C6 0.043(3) 0.068(4) 0.026(3) -0.006(3) -0.003(2) -0.004(3) C7 0.050(3) 0.018(2) 0.039(3) -0.0030(19) -0.002(2) 0.0003(19) C8 0.031(2) 0.025(2) 0.038(2) 0.003(2) -0.005(2) 0.0013(18) C9 0.037(3) 0.047(3) 0.026(2) -0.002(2) -0.001(2) -0.001(2) C10 0.033(3) 0.069(4) 0.031(3) 0.013(3) -0.009(2) -0.004(2) C11 0.039(3) 0.061(4) 0.046(3) 0.025(3) -0.008(3) -0.005(3) C12 0.040(3) 0.034(3) 0.052(3) 0.014(2) -0.002(3) -0.001(2) C13 0.033(2) 0.036(3) 0.025(2) -0.003(2) 0.002(2) -0.005(2) C14 0.032(2) 0.027(3) 0.025(2) 0.0019(18) -0.0006(19) 0.0036(17) C15 0.026(2) 0.024(2) 0.030(2) 0.0045(19) -0.0008(19) 0.0013(15) C16 0.037(3) 0.023(2) 0.039(3) -0.007(2) 0.002(2) -0.0027(19) C17 0.039(3) 0.030(3) 0.028(2) -0.003(2) 0.003(2) 0.0011(19) C18 0.026(2) 0.023(3) 0.032(2) 0.0057(18) 0.0010(19) -0.0012(16) C19 0.031(2) 0.023(2) 0.034(2) -0.001(2) -0.001(2) 0.0006(16) C20 0.034(3) 0.026(2) 0.030(2) 0.004(2) -0.008(2) -0.0053(17) C21 0.045(3) 0.028(3) 0.049(3) 0.003(2) -0.016(3) -0.002(2) C22 0.048(3) 0.041(4) 0.064(4) 0.016(3) -0.030(3) -0.010(3) C23 0.024(3) 0.052(4) 0.065(4) 0.026(3) -0.013(3) -0.004(2) C24 0.043(3) 0.037(3) 0.037(3) 0.010(2) 0.004(2) 0.007(2) C25 0.031(2) 0.028(3) 0.031(2) 0.0054(19) -0.0049(19) -0.0014(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 O1 1.866(3) . ? Mn1 O3 1.887(3) . ? Mn1 O2 1.917(3) . ? Mn1 N3 2.210(4) . ? Mn1 N1 2.212(4) . ? Mn1 N2 2.225(4) . ? Cl1 C21 1.726(6) . ? Cl2 C22 1.724(6) . ? Cl3 C23 1.728(5) . ? Cl4 C24 1.715(6) . ? O1 C15 1.346(5) . ? O2 C20 1.342(6) . ? O3 C25 1.352(6) . ? O4 N4 1.231(6) . ? O5 N4 1.223(6) . ? N1 C1 1.487(6) . ? N1 C7 1.488(6) . ? N1 C13 1.510(6) . ? N2 C3 1.318(7) . ? N2 C2 1.349(7) . ? N3 C8 1.342(6) . ? N3 C9 1.344(6) . ? N4 C18 1.452(6) . ? C1 C2 1.493(8) . ? C2 C6 1.401(7) . ? C3 C4 1.401(8) . ? C4 C5 1.364(9) . ? C5 C6 1.381(9) . ? C7 C8 1.502(7) . ? C8 C12 1.394(7) . ? C9 C10 1.377(7) . ? C10 C11 1.362(9) . ? C11 C12 1.380(8) . ? C13 C14 1.514(6) . ? C14 C19 1.384(6) . ? C14 C15 1.403(7) . ? C15 C16 1.409(7) . ? C16 C17 1.378(7) . ? C17 C18 1.381(7) . ? C18 C19 1.398(7) . ? C20 C21 1.387(7) . ? C20 C25 1.410(7) . ? C21 C22 1.401(9) . ? C22 C23 1.371(10) . ? C23 C24 1.420(8) . ? C24 C25 1.393(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O3 175.34(15) . . ? O1 Mn1 O2 90.03(15) . . ? O3 Mn1 O2 85.39(15) . . ? O1 Mn1 N3 91.85(15) . . ? O3 Mn1 N3 89.26(15) . . ? O2 Mn1 N3 92.76(14) . . ? O1 Mn1 N1 91.72(15) . . ? O3 Mn1 N1 92.94(15) . . ? O2 Mn1 N1 168.48(15) . . ? N3 Mn1 N1 75.81(14) . . ? O1 Mn1 N2 91.73(15) . . ? O3 Mn1 N2 89.49(15) . . ? O2 Mn1 N2 116.08(15) . . ? N3 Mn1 N2 150.93(15) . . ? N1 Mn1 N2 75.26(15) . . ? C15 O1 Mn1 119.1(3) . . ? C20 O2 Mn1 110.6(3) . . ? C25 O3 Mn1 111.6(3) . . ? C1 N1 C7 109.7(4) . . ? C1 N1 C13 108.3(4) . . ? C7 N1 C13 112.4(4) . . ? C1 N1 Mn1 107.6(3) . . ? C7 N1 Mn1 109.2(3) . . ? C13 N1 Mn1 109.5(3) . . ? C3 N2 C2 118.2(4) . . ? C3 N2 Mn1 127.3(4) . . ? C2 N2 Mn1 114.4(3) . . ? C8 N3 C9 119.2(4) . . ? C8 N3 Mn1 116.1(3) . . ? C9 N3 Mn1 124.7(4) . . ? O5 N4 O4 122.6(4) . . ? O5 N4 C18 119.0(4) . . ? O4 N4 C18 118.4(4) . . ? N1 C1 C2 110.9(4) . . ? N2 C2 C6 121.9(5) . . ? N2 C2 C1 116.6(4) . . ? C6 C2 C1 121.5(5) . . ? N2 C3 C4 123.4(5) . . ? C5 C4 C3 118.2(6) . . ? C4 C5 C6 119.7(5) . . ? C5 C6 C2 118.5(6) . . ? N1 C7 C8 111.4(4) . . ? N3 C8 C12 121.4(5) . . ? N3 C8 C7 116.1(4) . . ? C12 C8 C7 122.3(5) . . ? N3 C9 C10 121.7(5) . . ? C11 C10 C9 119.4(5) . . ? C10 C11 C12 119.8(5) . . ? C11 C12 C8 118.5(5) . . ? N1 C13 C14 113.5(4) . . ? C19 C14 C15 119.4(4) . . ? C19 C14 C13 121.9(4) . . ? C15 C14 C13 118.7(4) . . ? O1 C15 C14 120.3(4) . . ? O1 C15 C16 119.6(4) . . ? C14 C15 C16 120.1(4) . . ? C17 C16 C15 120.4(4) . . ? C16 C17 C18 118.7(4) . . ? C17 C18 C19 122.2(4) . . ? C17 C18 N4 119.0(4) . . ? C19 C18 N4 118.8(4) . . ? C14 C19 C18 119.2(4) . . ? O2 C20 C21 124.0(5) . . ? O2 C20 C25 116.0(4) . . ? C21 C20 C25 120.0(5) . . ? C20 C21 C22 120.4(6) . . ? C20 C21 Cl1 118.3(4) . . ? C22 C21 Cl1 121.4(5) . . ? C23 C22 C21 119.6(5) . . ? C23 C22 Cl2 120.5(5) . . ? C21 C22 Cl2 119.9(6) . . ? C22 C23 C24 121.1(5) . . ? C22 C23 Cl3 121.1(5) . . ? C24 C23 Cl3 117.8(5) . . ? C25 C24 C23 118.9(5) . . ? C25 C24 Cl4 119.3(4) . . ? C23 C24 Cl4 121.7(4) . . ? O3 C25 C24 124.7(5) . . ? O3 C25 C20 115.5(4) . . ? C24 C25 C20 119.8(5) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 71.85 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.568 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.098 #_END OF FILE data_p21c_c _database_code_depnum_ccdc_archive 'CCDC 226274' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Manganese(II)-di-chloro-2-(2-pyridylmethyl)(6-methyl-2-pyridylmethyl) aminomethyl)-4-nitrophenolat) ; _chemical_name_common ; Manganese(ii)-di-chloro-2-(2-pyridylmethyl)(6-methyl-2- pyridylmethyl) aminomethyl)-4-nitrophenolat) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H26 Cl2 Mn N4 O4' _chemical_formula_weight 536.31 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 P2(1)/c 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 15.7150(7) _cell_length_b 9.1986(4) _cell_length_c 17.2720(7) _cell_angle_alpha 90.00 _cell_angle_beta 99.040(3) _cell_angle_gamma 90.00 _cell_volume 2465.76(18) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1108 _exptl_absorpt_coefficient_mu 6.648 _exptl_absorpt_correction_type 'SADABS software package, Bruker AXS' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Goebel mirrow' _diffrn_measurement_device_type 'Bruker AXS SMART 6000 CCD' _diffrn_measurement_method 'combined omega theta-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13587 _diffrn_reflns_av_R_equivalents 0.1070 _diffrn_reflns_av_sigmaI/netI 0.0907 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 71.46 _reflns_number_total 4530 _reflns_number_gt 3109 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART software package, Bruker Nonius' _computing_cell_refinement 'SMART/SAINT software package, Bruker Nonius' _computing_data_reduction 'G. M. Sheldrick, Shelxltl Plus, Siemens Analytical X-ray Instruments 1990' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1264P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00003(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4530 _refine_ls_number_parameters 303 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0968 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.2005 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _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 0.69847(5) 1.02820(8) 0.03314(4) 0.0297(3) Uani 1 1 d . . . Cl1 Cl 0.81349(8) 1.16334(12) 0.12569(7) 0.0347(3) Uani 1 1 d . . . Cl2 Cl 0.58181(8) 0.93061(16) -0.06749(8) 0.0468(4) Uani 1 1 d . . . O1 O 0.7926(2) 0.4668(4) 0.0563(2) 0.0425(9) Uani 1 1 d . . . H1 H 0.8063 0.3885 0.0801 0.064 Uiso 1 1 calc R . . O2 O 0.9556(2) 0.6413(4) -0.2362(2) 0.0512(10) Uani 1 1 d . . . O3 O 1.0286(3) 0.4466(5) -0.2018(3) 0.0624(13) Uani 1 1 d . . . O4 O 0.6010(2) 1.1793(4) 0.0624(2) 0.0439(9) Uani 1 1 d . . . H4 H 0.539(5) 1.140(9) 0.051(4) 0.09(3) Uiso 1 1 d . . . N1 N 0.8011(2) 0.8455(4) 0.0220(2) 0.0272(8) Uani 1 1 d . . . N2 N 0.6861(3) 0.8643(4) 0.1268(3) 0.0376(10) Uani 1 1 d . . . N3 N 0.7651(2) 1.1001(4) -0.0673(2) 0.0314(9) Uani 1 1 d . . . N4 N 0.9743(3) 0.5374(5) -0.1923(3) 0.0392(10) Uani 1 1 d . . . C1 C 0.8289(3) 0.7941(5) 0.1026(3) 0.0309(10) Uani 1 1 d . . . H1A H 0.8688 0.8659 0.1314 0.037 Uiso 1 1 calc R . . H1B H 0.8603 0.7010 0.1014 0.037 Uiso 1 1 calc R . . C2 C 0.7523(3) 0.7726(5) 0.1447(3) 0.0332(11) Uani 1 1 d . . . C3 C 0.6187(4) 0.8545(6) 0.1669(4) 0.0511(15) Uani 1 1 d . . . H3A H 0.5706 0.9172 0.1533 0.061 Uiso 1 1 calc R . . C4 C 0.6184(4) 0.7546(6) 0.2273(3) 0.0528(15) Uani 1 1 d . . . H4A H 0.5714 0.7511 0.2559 0.063 Uiso 1 1 calc R . . C5 C 0.6859(4) 0.6624(6) 0.2449(3) 0.0484(14) Uani 1 1 d . . . H5A H 0.6863 0.5931 0.2857 0.058 Uiso 1 1 calc R . . C6 C 0.7544(4) 0.6694(6) 0.2033(3) 0.0426(13) Uani 1 1 d . . . H6A H 0.8018 0.6046 0.2148 0.051 Uiso 1 1 calc R . . C7 C 0.8715(3) 0.9243(5) -0.0082(3) 0.0303(10) Uani 1 1 d . . . H8A H 0.9113 0.8531 -0.0262 0.036 Uiso 1 1 calc R . . H8B H 0.9044 0.9820 0.0347 0.036 Uiso 1 1 calc R . . C8 C 0.8372(3) 1.0241(5) -0.0751(3) 0.0303(10) Uani 1 1 d . . . C9 C 0.7357(3) 1.1993(5) -0.1226(3) 0.0351(11) Uani 1 1 d . . . C10 C 0.7773(3) 1.2250(6) -0.1867(3) 0.0389(12) Uani 1 1 d . . . H10A H 0.7563 1.2968 -0.2244 0.047 Uiso 1 1 calc R . . C11 C 0.8493(3) 1.1448(6) -0.1946(3) 0.0379(12) Uani 1 1 d . . . H11A H 0.8776 1.1596 -0.2387 0.046 Uiso 1 1 calc R . . C12 C 0.8806(3) 1.0427(5) -0.1387(3) 0.0344(11) Uani 1 1 d . . . H12A H 0.9303 0.9868 -0.1435 0.041 Uiso 1 1 calc R . . C13 C 0.6579(4) 1.2878(7) -0.1128(4) 0.0542(16) Uani 1 1 d . . . H13A H 0.6366 1.2574 -0.0650 0.081 Uiso 1 1 calc R . . H13B H 0.6128 1.2727 -0.1582 0.081 Uiso 1 1 calc R . . H14C H 0.6735 1.3910 -0.1089 0.081 Uiso 1 1 calc R . . C14 C 0.7636(3) 0.7268(5) -0.0317(3) 0.0309(10) Uani 1 1 d . . . H14A H 0.7378 0.7709 -0.0823 0.037 Uiso 1 1 calc R . . H14B H 0.7164 0.6805 -0.0089 0.037 Uiso 1 1 calc R . . C15 C 0.8262(3) 0.6094(5) -0.0479(3) 0.0307(10) Uani 1 1 d . . . C16 C 0.8407(3) 0.4839(5) -0.0020(3) 0.0334(11) Uani 1 1 d . . . C17 C 0.9009(3) 0.3807(5) -0.0168(3) 0.0345(11) Uani 1 1 d . . . H17A H 0.9113 0.2979 0.0162 0.041 Uiso 1 1 calc R . . C18 C 0.9453(3) 0.3973(5) -0.0785(3) 0.0336(11) Uani 1 1 d . . . H18A H 0.9864 0.3271 -0.0887 0.040 Uiso 1 1 calc R . . C19 C 0.9286(3) 0.5193(5) -0.1255(3) 0.0309(11) Uani 1 1 d . . . C20 C 0.8702(3) 0.6246(5) -0.1116(3) 0.0314(10) Uani 1 1 d . . . H20A H 0.8602 0.7067 -0.1452 0.038 Uiso 1 1 calc R . . C21 C 0.5994(4) 1.2827(8) 0.1253(4) 0.072(2) Uani 1 1 d . . . H21A H 0.6593 1.3111 0.1468 0.087 Uiso 1 1 calc R . . H21B H 0.5740 1.2358 0.1679 0.087 Uiso 1 1 calc R . . C22 C 0.5499(6) 1.4129(10) 0.0994(8) 0.141(5) Uani 1 1 d . . . H22A H 0.5495 1.4785 0.1440 0.211 Uiso 1 1 calc R . . H22B H 0.4907 1.3854 0.0779 0.211 Uiso 1 1 calc R . . H22C H 0.5764 1.4622 0.0588 0.211 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0392(5) 0.0219(4) 0.0303(4) -0.0016(3) 0.0123(3) 0.0004(3) Cl1 0.0522(7) 0.0238(6) 0.0295(6) -0.0036(5) 0.0107(5) -0.0035(5) Cl2 0.0389(7) 0.0505(8) 0.0521(8) -0.0162(6) 0.0102(6) -0.0011(5) O1 0.061(2) 0.0257(19) 0.047(2) 0.0041(16) 0.0270(19) -0.0012(16) O2 0.064(3) 0.050(3) 0.045(2) 0.017(2) 0.026(2) 0.0127(19) O3 0.078(3) 0.050(3) 0.071(3) 0.012(2) 0.048(3) 0.024(2) O4 0.046(2) 0.036(2) 0.050(2) -0.0095(17) 0.0083(19) 0.0026(16) N1 0.037(2) 0.018(2) 0.027(2) -0.0001(16) 0.0063(17) -0.0043(15) N2 0.044(2) 0.029(2) 0.044(2) 0.0018(19) 0.021(2) 0.0001(18) N3 0.035(2) 0.028(2) 0.032(2) -0.0045(18) 0.0075(18) 0.0003(16) N4 0.049(3) 0.032(2) 0.040(2) -0.002(2) 0.017(2) 0.0012(19) C1 0.043(3) 0.024(3) 0.028(2) 0.001(2) 0.012(2) 0.0019(19) C2 0.043(3) 0.026(3) 0.032(3) -0.002(2) 0.012(2) -0.003(2) C3 0.064(4) 0.039(3) 0.057(4) 0.006(3) 0.030(3) 0.002(3) C4 0.073(4) 0.043(4) 0.051(3) 0.002(3) 0.037(3) -0.005(3) C5 0.072(4) 0.043(3) 0.033(3) 0.008(3) 0.017(3) -0.008(3) C6 0.060(3) 0.036(3) 0.033(3) 0.005(2) 0.012(3) -0.001(2) C7 0.033(2) 0.030(3) 0.028(2) -0.002(2) 0.005(2) -0.0027(19) C8 0.040(3) 0.021(2) 0.030(2) -0.0047(19) 0.007(2) -0.0019(18) C9 0.041(3) 0.032(3) 0.031(3) -0.007(2) 0.003(2) 0.001(2) C10 0.055(3) 0.031(3) 0.032(3) 0.001(2) 0.012(2) -0.004(2) C11 0.058(3) 0.030(3) 0.029(3) -0.002(2) 0.017(2) -0.008(2) C12 0.046(3) 0.027(3) 0.033(3) -0.007(2) 0.016(2) -0.007(2) C13 0.060(4) 0.048(4) 0.057(4) 0.015(3) 0.017(3) 0.010(3) C14 0.037(2) 0.026(3) 0.032(3) 0.000(2) 0.012(2) 0.0022(19) C15 0.038(3) 0.022(2) 0.033(3) -0.002(2) 0.008(2) -0.0020(19) C16 0.043(3) 0.026(3) 0.033(3) -0.003(2) 0.011(2) -0.006(2) C17 0.044(3) 0.019(2) 0.041(3) 0.001(2) 0.009(2) -0.0019(19) C18 0.037(3) 0.023(3) 0.043(3) -0.005(2) 0.012(2) -0.0005(19) C19 0.038(3) 0.026(3) 0.031(3) -0.007(2) 0.010(2) -0.0023(19) C20 0.042(3) 0.022(2) 0.031(2) 0.000(2) 0.008(2) -0.0020(19) C21 0.056(4) 0.074(5) 0.086(5) -0.047(4) 0.008(4) 0.008(3) C22 0.100(7) 0.064(6) 0.241(14) -0.078(8) -0.028(8) 0.023(5) _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 O4 2.186(4) . ? Mn1 N2 2.242(4) . ? Mn1 N3 2.262(4) . ? Mn1 N1 2.358(4) . ? Mn1 Cl2 2.4873(15) . ? Mn1 Cl1 2.5416(14) . ? O1 C16 1.360(6) . ? O2 N4 1.225(5) . ? O3 N4 1.224(6) . ? O4 C21 1.447(7) . ? N1 C1 1.470(6) . ? N1 C7 1.483(5) . ? N1 C14 1.492(6) . ? N2 C2 1.337(6) . ? N2 C3 1.357(6) . ? N3 C9 1.349(6) . ? N3 C8 1.355(6) . ? N4 C19 1.462(6) . ? C1 C2 1.514(6) . ? C2 C6 1.385(7) . ? C3 C4 1.391(8) . ? C4 C5 1.355(8) . ? C5 C6 1.386(7) . ? C7 C8 1.507(7) . ? C8 C12 1.392(7) . ? C9 C10 1.392(7) . ? C9 C13 1.500(7) . ? C10 C11 1.375(7) . ? C11 C12 1.382(7) . ? C14 C15 1.517(6) . ? C15 C20 1.396(6) . ? C15 C16 1.399(7) . ? C16 C17 1.391(7) . ? C17 C18 1.371(7) . ? C18 C19 1.386(7) . ? C19 C20 1.380(6) . ? C21 C22 1.460(11) . ? 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 O4 Mn1 N2 96.75(15) . . ? O4 Mn1 N3 114.66(15) . . ? N2 Mn1 N3 148.56(15) . . ? O4 Mn1 N1 170.19(14) . . ? N2 Mn1 N1 73.61(14) . . ? N3 Mn1 N1 74.95(14) . . ? O4 Mn1 Cl2 85.69(11) . . ? N2 Mn1 Cl2 97.10(12) . . ? N3 Mn1 Cl2 87.07(11) . . ? N1 Mn1 Cl2 97.13(10) . . ? O4 Mn1 Cl1 89.91(11) . . ? N2 Mn1 Cl1 90.50(12) . . ? N3 Mn1 Cl1 88.29(10) . . ? N1 Mn1 Cl1 88.40(9) . . ? Cl2 Mn1 Cl1 171.61(5) . . ? C21 O4 Mn1 133.4(3) . . ? C1 N1 C7 111.3(3) . . ? C1 N1 C14 112.5(3) . . ? C7 N1 C14 112.5(3) . . ? C1 N1 Mn1 104.9(3) . . ? C7 N1 Mn1 103.7(3) . . ? C14 N1 Mn1 111.3(3) . . ? C2 N2 C3 118.9(4) . . ? C2 N2 Mn1 116.0(3) . . ? C3 N2 Mn1 125.2(4) . . ? C9 N3 C8 118.5(4) . . ? C9 N3 Mn1 126.3(3) . . ? C8 N3 Mn1 114.8(3) . . ? O3 N4 O2 123.7(4) . . ? O3 N4 C19 117.9(4) . . ? O2 N4 C19 118.5(4) . . ? N1 C1 C2 110.9(4) . . ? N2 C2 C6 121.9(5) . . ? N2 C2 C1 117.1(4) . . ? C6 C2 C1 120.8(5) . . ? N2 C3 C4 121.4(6) . . ? C5 C4 C3 119.1(5) . . ? C4 C5 C6 120.0(5) . . ? C2 C6 C5 118.7(5) . . ? N1 C7 C8 111.8(4) . . ? N3 C8 C12 122.4(5) . . ? N3 C8 C7 116.2(4) . . ? C12 C8 C7 121.3(4) . . ? N3 C9 C10 121.8(5) . . ? N3 C9 C13 118.8(4) . . ? C10 C9 C13 119.4(5) . . ? C11 C10 C9 119.0(5) . . ? C10 C11 C12 120.2(5) . . ? C11 C12 C8 118.1(5) . . ? N1 C14 C15 115.5(4) . . ? C20 C15 C16 118.2(4) . . ? C20 C15 C14 119.4(4) . . ? C16 C15 C14 122.4(4) . . ? O1 C16 C17 122.0(5) . . ? O1 C16 C15 117.1(4) . . ? C17 C16 C15 120.9(5) . . ? C18 C17 C16 120.6(5) . . ? C17 C18 C19 118.3(4) . . ? C20 C19 C18 122.4(4) . . ? C20 C19 N4 118.6(4) . . ? C18 C19 N4 119.0(4) . . ? C19 C20 C15 119.5(5) . . ? O4 C21 C22 112.3(7) . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 71.46 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.977 _refine_diff_density_min -0.853 _refine_diff_density_rms 0.124 data_p21c _database_code_depnum_ccdc_archive 'CCDC 226512' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Manganese(II)-di-chloro-2-(2-pyridylmethyl)(6-methyl-2-pyridylmethyl) aminomethyl)-phenolat) ; _chemical_name_common ; Manganese(ii)-di-chloro-2-(2-pyridylmethyl)(6-methyl-2- pyridylmethyl) aminomethyl)-phenolat) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H24.50 Cl2 Mn N3 O2' _chemical_formula_weight 476.78 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 P2(1)/c 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 19.3575(3) _cell_length_b 13.1371(2) _cell_length_c 17.3527(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.1340(10) _cell_angle_gamma 90.00 _cell_volume 4387.55(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'rod shaped' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1972 _exptl_absorpt_coefficient_mu 7.314 _exptl_absorpt_correction_type 'SADABS software package, Bruker AXS' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'Goebel mirrow' _diffrn_measurement_device_type 'Bruker AXS SMART 6000 CCD' _diffrn_measurement_method 'combined omega theta-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24727 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 71.40 _reflns_number_total 7973 _reflns_number_gt 6996 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART software package, Bruker Nonius' _computing_cell_refinement 'SMART/SAINT software package, Bruker Nonius' _computing_data_reduction 'G. M. Sheldrick, Shelxltl Plus, Siemens Analytical X-ray Instruments 1990' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+2.5716P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7973 _refine_ls_number_parameters 534 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 0.15071(2) 0.26895(3) 0.41219(2) 0.01263(11) Uani 1 1 d . . . Mn2 Mn 0.34770(2) 0.71695(3) 0.64194(2) 0.01474(11) Uani 1 1 d . . . Cl1 Cl 0.15956(4) 0.39667(5) 0.30579(4) 0.01961(15) Uani 1 1 d . . . Cl2 Cl 0.05260(3) 0.34137(5) 0.46371(4) 0.02162(15) Uani 1 1 d . . . Cl3 Cl 0.33417(4) 0.57749(5) 0.73392(4) 0.02207(16) Uani 1 1 d . . . Cl4 Cl 0.42887(4) 0.64235(5) 0.55957(4) 0.02408(16) Uani 1 1 d . . . O1 O 0.15721(11) 0.14662(14) 0.51088(12) 0.0180(4) Uani 1 1 d . . . H1 H 0.143(3) 0.160(4) 0.549(3) 0.076(18) Uiso 1 1 d . . . O2 O 0.35430(13) 0.86297(16) 0.56364(14) 0.0281(5) Uani 1 1 d . . . H2 H 0.351(4) 0.846(6) 0.527(4) 0.14(3) Uiso 1 1 d . . . N1 N 0.23224(12) 0.16256(16) 0.36459(12) 0.0148(5) Uani 1 1 d . . . N2 N 0.08957(12) 0.15158(17) 0.33467(13) 0.0169(5) Uani 1 1 d . . . N3 N 0.25786(12) 0.31502(16) 0.47017(12) 0.0151(5) Uani 1 1 d . . . N4 N 0.25672(11) 0.81040(17) 0.68461(12) 0.0152(5) Uani 1 1 d . . . N5 N 0.24947(13) 0.67136(17) 0.56803(13) 0.0201(5) Uani 1 1 d . . . N6 N 0.39776(12) 0.82761(18) 0.73437(13) 0.0187(5) Uani 1 1 d . . . C1 C 0.20199(15) 0.1242(2) 0.28813(15) 0.0211(6) Uani 1 1 d . . . H1A H 0.2275 0.0625 0.2749 0.025 Uiso 1 1 calc R . . H1B H 0.2080 0.1764 0.2482 0.025 Uiso 1 1 calc R . . C2 C 0.12594(16) 0.0991(2) 0.28659(16) 0.0200(6) Uani 1 1 d . . . C3 C 0.02076(16) 0.1340(2) 0.33317(17) 0.0227(6) Uani 1 1 d . . . H3A H -0.0048 0.1702 0.3681 0.027 Uiso 1 1 calc R . . C4 C -0.01402(17) 0.0650(2) 0.28267(17) 0.0279(7) Uani 1 1 d . . . H4A H -0.0626 0.0544 0.2828 0.033 Uiso 1 1 calc R . . C5 C 0.02294(17) 0.0122(2) 0.23233(18) 0.0289(7) Uani 1 1 d . . . H5A H 0.0001 -0.0349 0.1966 0.035 Uiso 1 1 calc R . . C6 C 0.09409(18) 0.0286(2) 0.23427(17) 0.0276(7) Uani 1 1 d . . . H6A H 0.1206 -0.0078 0.2004 0.033 Uiso 1 1 calc R . . C7 C 0.29225(14) 0.2293(2) 0.35672(16) 0.0186(6) Uani 1 1 d . . . H7A H 0.2810 0.2763 0.3126 0.022 Uiso 1 1 calc R . . H7B H 0.3325 0.1874 0.3457 0.022 Uiso 1 1 calc R . . C8 C 0.31103(15) 0.2900(2) 0.42951(16) 0.0174(6) Uani 1 1 d . . . C9 C 0.27301(15) 0.3682(2) 0.53661(15) 0.0175(6) Uani 1 1 d . . . C10 C 0.34029(16) 0.4028(2) 0.55986(16) 0.0213(6) Uani 1 1 d . . . H10A H 0.3493 0.4428 0.6054 0.026 Uiso 1 1 calc R . . C11 C 0.39328(16) 0.3785(2) 0.51643(18) 0.0242(6) Uani 1 1 d . . . H11A H 0.4391 0.4024 0.5312 0.029 Uiso 1 1 calc R . . C12 C 0.37913(15) 0.3188(2) 0.45099(17) 0.0212(6) Uani 1 1 d . . . H12A H 0.4153 0.2981 0.4215 0.025 Uiso 1 1 calc R . . C13 C 0.21573(16) 0.3853(2) 0.58543(16) 0.0228(6) Uani 1 1 d . . . H13A H 0.1727 0.3560 0.5598 0.034 Uiso 0.50 1 calc PR . . H13B H 0.2095 0.4585 0.5928 0.034 Uiso 0.50 1 calc PR . . H13C H 0.2272 0.3526 0.6359 0.034 Uiso 0.50 1 calc PR . . H13D H 0.2335 0.4221 0.6325 0.034 Uiso 0.50 1 calc PR . . H13E H 0.1968 0.3195 0.5996 0.034 Uiso 0.50 1 calc PR . . H13F H 0.1790 0.4255 0.5564 0.034 Uiso 0.50 1 calc PR . . C14 C 0.25540(14) 0.0772(2) 0.41828(15) 0.0170(6) Uani 1 1 d . . . H14A H 0.2795 0.1061 0.4665 0.020 Uiso 1 1 calc R . . H14B H 0.2894 0.0350 0.3938 0.020 Uiso 1 1 calc R . . C15 C 0.19748(15) 0.0101(2) 0.43887(15) 0.0182(6) Uani 1 1 d . . . C16 C 0.14972(14) 0.0466(2) 0.48752(15) 0.0171(6) Uani 1 1 d . . . C17 C 0.09650(15) -0.0144(2) 0.50951(16) 0.0209(6) Uani 1 1 d . . . H17A H 0.0650 0.0111 0.5432 0.025 Uiso 1 1 calc R . . C18 C 0.09027(16) -0.1134(2) 0.48142(17) 0.0260(7) Uani 1 1 d . . . H18A H 0.0541 -0.1559 0.4959 0.031 Uiso 1 1 calc R . . C19 C 0.13619(17) -0.1503(2) 0.43266(18) 0.0265(7) Uani 1 1 d . . . H19A H 0.1313 -0.2180 0.4134 0.032 Uiso 1 1 calc R . . C20 C 0.18919(16) -0.0895(2) 0.41176(17) 0.0230(6) Uani 1 1 d . . . H20A H 0.2206 -0.1159 0.3783 0.028 Uiso 1 1 calc R . . C21 C 0.19794(14) 0.7378(2) 0.67895(17) 0.0202(6) Uani 1 1 d . . . H21A H 0.1544 0.7747 0.6856 0.024 Uiso 1 1 calc R . . H21B H 0.2057 0.6867 0.7209 0.024 Uiso 1 1 calc R . . C22 C 0.19076(15) 0.6845(2) 0.60141(16) 0.0200(6) Uani 1 1 d . . . C23 C 0.24598(17) 0.6227(2) 0.49880(17) 0.0256(7) Uani 1 1 d . . . H23A H 0.2874 0.6153 0.4744 0.031 Uiso 1 1 calc R . . C24 C 0.18558(18) 0.5839(2) 0.46258(19) 0.0299(7) Uani 1 1 d . . . H24A H 0.1852 0.5492 0.4145 0.036 Uiso 1 1 calc R . . C25 C 0.12518(18) 0.5961(2) 0.49690(19) 0.0316(8) Uani 1 1 d . . . H25A H 0.0826 0.5692 0.4731 0.038 Uiso 1 1 calc R . . C26 C 0.12748(16) 0.6485(2) 0.56718(19) 0.0259(7) Uani 1 1 d . . . H26A H 0.0862 0.6594 0.5912 0.031 Uiso 1 1 calc R . . C27 C 0.27846(14) 0.8381(2) 0.76587(15) 0.0194(6) Uani 1 1 d . . . H27A H 0.2737 0.7781 0.7994 0.023 Uiso 1 1 calc R . . H27B H 0.2476 0.8923 0.7821 0.023 Uiso 1 1 calc R . . C28 C 0.35276(15) 0.8750(2) 0.77637(16) 0.0186(6) Uani 1 1 d . . . C29 C 0.46501(16) 0.8578(2) 0.74493(18) 0.0261(7) Uani 1 1 d . . . C30 C 0.48737(17) 0.9351(3) 0.7976(2) 0.0333(8) Uani 1 1 d . . . H30 H 0.5346 0.9560 0.8032 0.040 Uiso 1 1 calc R . . C31 C 0.44100(19) 0.9799(3) 0.8409(2) 0.0380(8) Uani 1 1 d . . . H31A H 0.4559 1.0308 0.8779 0.046 Uiso 1 1 calc R . . C32 C 0.37198(17) 0.9507(2) 0.83035(19) 0.0303(7) Uani 1 1 d . . . H32A H 0.3386 0.9815 0.8593 0.036 Uiso 1 1 calc R . . C33 C 0.51496(18) 0.8068(3) 0.6999(2) 0.0474(10) Uani 1 1 d . . . H33A H 0.4908 0.7552 0.6663 0.071 Uiso 0.50 1 calc PR . . H33B H 0.5511 0.7740 0.7354 0.071 Uiso 0.50 1 calc PR . . H33C H 0.5363 0.8571 0.6681 0.071 Uiso 0.50 1 calc PR . . H33D H 0.5613 0.8356 0.7136 0.071 Uiso 0.50 1 calc PR . . H33E H 0.5011 0.8169 0.6445 0.071 Uiso 0.50 1 calc PR . . H33F H 0.5158 0.7338 0.7117 0.071 Uiso 0.50 1 calc PR . . C34 C 0.23482(14) 0.9016(2) 0.63686(16) 0.0172(6) Uani 1 1 d . . . H34A H 0.1953 0.9342 0.6591 0.021 Uiso 1 1 calc R . . H34B H 0.2178 0.8785 0.5839 0.021 Uiso 1 1 calc R . . C35 C 0.29035(14) 0.9806(2) 0.63075(15) 0.0173(6) Uani 1 1 d . . . C36 C 0.34811(15) 0.9602(2) 0.59124(16) 0.0213(6) Uani 1 1 d . . . C37 C 0.39730(16) 1.0345(2) 0.58075(19) 0.0286(7) Uani 1 1 d . . . H37A H 0.4362 1.0193 0.5537 0.034 Uiso 1 1 calc R . . C38 C 0.38893(17) 1.1308(2) 0.61018(19) 0.0289(7) Uani 1 1 d . . . H38A H 0.4220 1.1823 0.6026 0.035 Uiso 1 1 calc R . . C39 C 0.33329(17) 1.1529(2) 0.65028(17) 0.0256(7) Uani 1 1 d . . . H39A H 0.3283 1.2191 0.6709 0.031 Uiso 1 1 calc R . . C40 C 0.28460(15) 1.0783(2) 0.66046(16) 0.0202(6) Uani 1 1 d . . . H40A H 0.2464 1.0942 0.6884 0.024 Uiso 1 1 calc R . . C41 C 0.03829(16) 0.2173(2) 0.65156(18) 0.0274(7) Uani 1 1 d . . . H41A H 0.0393 0.2546 0.7006 0.041 Uiso 1 1 calc R . . H41B H 0.0059 0.1600 0.6518 0.041 Uiso 1 1 calc R . . H41C H 0.0231 0.2629 0.6084 0.041 Uiso 1 1 calc R . . O3 O 0.10521(12) 0.1803(2) 0.64276(13) 0.0367(6) Uani 1 1 d . . . H3 H 0.1226 0.1547 0.6848 0.055 Uiso 1 1 calc R . . C42 C 0.4236(2) 0.8472(3) 0.3997(2) 0.0512(11) Uani 1 1 d . . . H42A H 0.3736 0.8360 0.4003 0.077 Uiso 1 1 calc R . . H42B H 0.4424 0.7961 0.3665 0.077 Uiso 1 1 calc R . . H42C H 0.4315 0.9153 0.3795 0.077 Uiso 1 1 calc R . . O4 O 0.45697(13) 0.83865(19) 0.47574(13) 0.0367(6) 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 0.0168(2) 0.0107(2) 0.0101(2) -0.00027(15) 0.00029(16) 0.00108(16) Mn2 0.0174(2) 0.0126(2) 0.0141(2) 0.00037(15) 0.00125(16) 0.00125(17) Cl1 0.0286(3) 0.0175(3) 0.0125(3) 0.0032(2) 0.0011(2) 0.0007(3) Cl2 0.0225(3) 0.0201(3) 0.0228(3) -0.0024(2) 0.0049(3) 0.0040(3) Cl3 0.0287(4) 0.0173(3) 0.0200(3) 0.0037(2) 0.0016(3) -0.0015(3) Cl4 0.0231(3) 0.0181(3) 0.0324(4) 0.0025(3) 0.0090(3) 0.0049(3) O1 0.0282(11) 0.0122(9) 0.0140(10) 0.0005(7) 0.0037(8) 0.0013(8) O2 0.0443(14) 0.0149(10) 0.0279(13) 0.0010(9) 0.0166(10) 0.0057(9) N1 0.0199(12) 0.0137(11) 0.0107(11) -0.0004(8) 0.0010(9) 0.0013(9) N2 0.0215(12) 0.0159(11) 0.0125(11) 0.0010(9) -0.0021(9) -0.0011(9) N3 0.0207(11) 0.0112(10) 0.0124(11) 0.0017(8) -0.0021(9) 0.0004(9) N4 0.0160(11) 0.0146(11) 0.0146(11) -0.0003(9) -0.0006(9) -0.0014(9) N5 0.0257(13) 0.0150(11) 0.0182(12) -0.0004(9) -0.0043(10) 0.0007(10) N6 0.0187(12) 0.0169(11) 0.0197(12) 0.0025(9) -0.0020(9) -0.0006(10) C1 0.0297(16) 0.0216(14) 0.0119(14) -0.0049(10) 0.0019(11) 0.0027(12) C2 0.0310(16) 0.0146(13) 0.0132(14) 0.0020(10) -0.0034(11) -0.0025(12) C3 0.0276(16) 0.0204(14) 0.0194(15) 0.0045(11) -0.0009(12) -0.0033(12) C4 0.0345(18) 0.0240(15) 0.0238(16) 0.0008(12) -0.0022(13) -0.0087(14) C5 0.0341(17) 0.0223(15) 0.0278(17) -0.0004(12) -0.0074(13) -0.0100(14) C6 0.0420(19) 0.0208(15) 0.0190(15) -0.0061(11) -0.0015(13) -0.0027(14) C7 0.0205(14) 0.0179(14) 0.0182(14) 0.0005(10) 0.0065(11) 0.0009(11) C8 0.0226(14) 0.0125(12) 0.0169(14) 0.0050(10) 0.0003(11) 0.0009(11) C9 0.0269(15) 0.0106(12) 0.0139(13) 0.0018(10) -0.0033(11) 0.0007(11) C10 0.0324(16) 0.0120(12) 0.0172(14) -0.0004(10) -0.0072(12) -0.0052(12) C11 0.0230(15) 0.0172(14) 0.0306(17) 0.0018(12) -0.0048(12) -0.0035(12) C12 0.0195(14) 0.0165(14) 0.0274(16) 0.0030(11) 0.0015(11) -0.0024(11) C13 0.0303(16) 0.0210(15) 0.0162(14) -0.0018(11) -0.0011(11) 0.0009(13) C14 0.0220(14) 0.0134(13) 0.0153(14) 0.0010(10) 0.0006(11) 0.0044(11) C15 0.0226(14) 0.0141(13) 0.0162(14) 0.0018(10) -0.0052(11) 0.0025(11) C16 0.0219(14) 0.0140(13) 0.0142(13) 0.0030(10) -0.0042(10) 0.0007(11) C17 0.0232(14) 0.0220(15) 0.0163(14) 0.0046(11) -0.0028(11) -0.0008(12) C18 0.0285(16) 0.0212(15) 0.0253(16) 0.0064(12) -0.0113(13) -0.0063(13) C19 0.0365(18) 0.0138(14) 0.0263(16) 0.0021(11) -0.0104(13) -0.0019(13) C20 0.0330(17) 0.0145(13) 0.0199(15) -0.0026(11) -0.0048(12) 0.0053(12) C21 0.0157(14) 0.0192(14) 0.0256(16) 0.0003(11) 0.0014(11) -0.0020(11) C22 0.0244(15) 0.0104(12) 0.0232(15) 0.0025(10) -0.0069(11) -0.0004(11) C23 0.0396(18) 0.0146(14) 0.0211(15) -0.0002(11) -0.0047(13) 0.0030(13) C24 0.045(2) 0.0135(14) 0.0282(17) -0.0044(12) -0.0115(14) 0.0010(14) C25 0.0401(19) 0.0101(13) 0.0387(19) 0.0044(12) -0.0228(15) -0.0057(13) C26 0.0242(15) 0.0133(14) 0.0381(18) 0.0060(12) -0.0069(13) 0.0001(12) C27 0.0228(14) 0.0212(14) 0.0139(14) -0.0019(10) 0.0012(11) 0.0019(12) C28 0.0229(14) 0.0165(13) 0.0152(14) 0.0015(10) -0.0040(11) 0.0012(11) C29 0.0201(15) 0.0269(16) 0.0306(17) 0.0031(13) -0.0010(12) -0.0020(12) C30 0.0240(16) 0.0316(17) 0.041(2) 0.0038(14) -0.0119(14) -0.0097(14) C31 0.039(2) 0.0278(17) 0.044(2) -0.0108(15) -0.0128(16) -0.0030(16) C32 0.0328(18) 0.0273(16) 0.0290(17) -0.0102(13) -0.0049(13) 0.0018(14) C33 0.0270(18) 0.065(3) 0.050(2) -0.021(2) 0.0031(16) -0.0092(18) C34 0.0163(13) 0.0147(13) 0.0194(14) 0.0020(10) -0.0044(10) 0.0029(11) C35 0.0200(14) 0.0162(13) 0.0149(13) 0.0016(10) -0.0013(10) 0.0026(11) C36 0.0293(16) 0.0142(14) 0.0213(15) 0.0045(11) 0.0067(12) 0.0054(12) C37 0.0263(16) 0.0256(16) 0.0353(18) 0.0105(13) 0.0093(13) 0.0035(13) C38 0.0292(17) 0.0194(15) 0.0375(19) 0.0091(13) 0.0016(13) -0.0008(13) C39 0.0341(17) 0.0143(14) 0.0268(16) 0.0013(11) -0.0046(13) 0.0006(13) C40 0.0233(15) 0.0183(14) 0.0191(14) 0.0001(11) 0.0022(11) 0.0051(12) C41 0.0284(16) 0.0321(17) 0.0210(16) -0.0022(12) -0.0001(12) -0.0014(13) O3 0.0433(14) 0.0492(15) 0.0188(11) 0.0103(10) 0.0093(10) 0.0185(12) C42 0.074(3) 0.060(3) 0.0184(18) -0.0050(16) -0.0006(17) -0.018(2) O4 0.0399(14) 0.0381(14) 0.0322(13) -0.0016(10) 0.0046(10) 0.0004(11) _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 N3 2.288(2) . ? Mn1 N2 2.291(2) . ? Mn1 N1 2.325(2) . ? Mn1 O1 2.3420(19) . ? Mn1 Cl2 2.3820(7) . ? Mn1 Cl1 2.5142(7) . ? Mn2 N5 2.258(2) . ? Mn2 N6 2.301(2) . ? Mn2 N4 2.331(2) . ? Mn2 O2 2.362(2) . ? Mn2 Cl4 2.4397(8) . ? Mn2 Cl3 2.4621(7) . ? O1 C16 1.378(3) . ? O2 C36 1.374(4) . ? N1 C7 1.473(3) . ? N1 C1 1.480(3) . ? N1 C14 1.496(3) . ? N2 C2 1.339(4) . ? N2 C3 1.349(4) . ? N3 C8 1.349(4) . ? N3 C9 1.353(3) . ? N4 C27 1.473(3) . ? N4 C21 1.480(3) . ? N4 C34 1.492(3) . ? N5 C22 1.341(4) . ? N5 C23 1.356(4) . ? N6 C28 1.347(4) . ? N6 C29 1.355(4) . ? C1 C2 1.506(4) . ? C2 C6 1.394(4) . ? C3 C4 1.384(4) . ? C4 C5 1.375(5) . ? C5 C6 1.391(5) . ? C7 C8 1.505(4) . ? C8 C12 1.384(4) . ? C9 C10 1.397(4) . ? C9 C13 1.483(4) . ? C10 C11 1.374(4) . ? C11 C12 1.383(4) . ? C14 C15 1.499(4) . ? C15 C20 1.394(4) . ? C15 C16 1.402(4) . ? C16 C17 1.391(4) . ? C17 C18 1.389(4) . ? C18 C19 1.379(5) . ? C19 C20 1.379(4) . ? C21 C22 1.510(4) . ? C22 C26 1.386(4) . ? C23 C24 1.366(4) . ? C24 C25 1.377(5) . ? C25 C26 1.397(5) . ? C27 C28 1.510(4) . ? C28 C32 1.389(4) . ? C29 C30 1.403(4) . ? C29 C33 1.468(5) . ? C30 C31 1.364(5) . ? C31 C32 1.383(5) . ? C34 C35 1.506(4) . ? C35 C40 1.392(4) . ? C35 C36 1.398(4) . ? C36 C37 1.389(4) . ? C37 C38 1.380(5) . ? C38 C39 1.374(4) . ? C39 C40 1.384(4) . ? C41 O3 1.407(4) . ? C42 O4 1.410(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Mn1 N2 145.43(8) . . ? N3 Mn1 N1 72.38(8) . . ? N2 Mn1 N1 73.41(8) . . ? N3 Mn1 O1 83.37(7) . . ? N2 Mn1 O1 87.22(7) . . ? N1 Mn1 O1 82.05(7) . . ? N3 Mn1 Cl2 116.81(6) . . ? N2 Mn1 Cl2 96.12(6) . . ? N1 Mn1 Cl2 166.45(6) . . ? O1 Mn1 Cl2 88.99(5) . . ? N3 Mn1 Cl1 90.96(6) . . ? N2 Mn1 Cl1 95.13(6) . . ? N1 Mn1 Cl1 92.19(6) . . ? O1 Mn1 Cl1 172.91(6) . . ? Cl2 Mn1 Cl1 97.39(3) . . ? N5 Mn2 N6 146.10(9) . . ? N5 Mn2 N4 72.62(8) . . ? N6 Mn2 N4 73.86(8) . . ? N5 Mn2 O2 89.01(9) . . ? N6 Mn2 O2 80.98(9) . . ? N4 Mn2 O2 81.04(8) . . ? N5 Mn2 Cl4 96.70(7) . . ? N6 Mn2 Cl4 114.37(6) . . ? N4 Mn2 Cl4 162.41(6) . . ? O2 Mn2 Cl4 84.92(6) . . ? N5 Mn2 Cl3 91.68(6) . . ? N6 Mn2 Cl3 94.84(6) . . ? N4 Mn2 Cl3 92.84(6) . . ? O2 Mn2 Cl3 173.34(6) . . ? Cl4 Mn2 Cl3 101.58(3) . . ? C16 O1 Mn1 116.32(16) . . ? C36 O2 Mn2 122.85(18) . . ? C7 N1 C1 111.1(2) . . ? C7 N1 C14 108.5(2) . . ? C1 N1 C14 111.5(2) . . ? C7 N1 Mn1 104.30(15) . . ? C1 N1 Mn1 107.72(16) . . ? C14 N1 Mn1 113.53(15) . . ? C2 N2 C3 118.9(2) . . ? C2 N2 Mn1 116.08(18) . . ? C3 N2 Mn1 125.01(19) . . ? C8 N3 C9 117.6(2) . . ? C8 N3 Mn1 114.34(17) . . ? C9 N3 Mn1 127.94(19) . . ? C27 N4 C21 111.2(2) . . ? C27 N4 C34 111.6(2) . . ? C21 N4 C34 108.1(2) . . ? C27 N4 Mn2 106.61(16) . . ? C21 N4 Mn2 103.94(16) . . ? C34 N4 Mn2 115.20(16) . . ? C22 N5 C23 118.6(3) . . ? C22 N5 Mn2 114.94(18) . . ? C23 N5 Mn2 126.0(2) . . ? C28 N6 C29 117.3(2) . . ? C28 N6 Mn2 114.89(18) . . ? C29 N6 Mn2 127.3(2) . . ? N1 C1 C2 112.5(2) . . ? N2 C2 C6 121.5(3) . . ? N2 C2 C1 117.0(2) . . ? C6 C2 C1 121.4(3) . . ? N2 C3 C4 122.5(3) . . ? C5 C4 C3 118.8(3) . . ? C4 C5 C6 119.2(3) . . ? C5 C6 C2 119.1(3) . . ? N1 C7 C8 111.1(2) . . ? N3 C8 C12 123.4(3) . . ? N3 C8 C7 116.0(2) . . ? C12 C8 C7 120.6(3) . . ? N3 C9 C10 121.6(3) . . ? N3 C9 C13 117.2(2) . . ? C10 C9 C13 121.1(2) . . ? C11 C10 C9 119.6(3) . . ? C10 C11 C12 119.2(3) . . ? C11 C12 C8 118.4(3) . . ? N1 C14 C15 114.0(2) . . ? C20 C15 C16 117.7(3) . . ? C20 C15 C14 122.2(3) . . ? C16 C15 C14 120.1(2) . . ? O1 C16 C17 121.8(3) . . ? O1 C16 C15 116.6(2) . . ? C17 C16 C15 121.6(3) . . ? C18 C17 C16 118.8(3) . . ? C19 C18 C17 120.5(3) . . ? C20 C19 C18 120.2(3) . . ? C19 C20 C15 121.2(3) . . ? N4 C21 C22 110.8(2) . . ? N5 C22 C26 121.5(3) . . ? N5 C22 C21 116.3(2) . . ? C26 C22 C21 122.2(3) . . ? N5 C23 C24 122.9(3) . . ? C23 C24 C25 118.8(3) . . ? C24 C25 C26 119.0(3) . . ? C22 C26 C25 119.1(3) . . ? N4 C27 C28 111.5(2) . . ? N6 C28 C32 123.6(3) . . ? N6 C28 C27 116.7(2) . . ? C32 C28 C27 119.6(3) . . ? N6 C29 C30 121.7(3) . . ? N6 C29 C33 118.2(3) . . ? C30 C29 C33 120.1(3) . . ? C31 C30 C29 119.7(3) . . ? C30 C31 C32 119.3(3) . . ? C31 C32 C28 118.3(3) . . ? N4 C34 C35 115.4(2) . . ? C40 C35 C36 117.2(3) . . ? C40 C35 C34 121.6(3) . . ? C36 C35 C34 121.1(2) . . ? O2 C36 C37 121.4(3) . . ? O2 C36 C35 116.9(3) . . ? C37 C36 C35 121.7(3) . . ? C38 C37 C36 119.1(3) . . ? C39 C38 C37 120.7(3) . . ? C38 C39 C40 119.8(3) . . ? C39 C40 C35 121.5(3) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 71.40 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 1.633 _refine_diff_density_min -0.639 _refine_diff_density_rms 0.079 #_END OF FILE data_pbca _database_code_depnum_ccdc_archive 'CCDC 226513' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Manganese(II)-di-chloro-2-(2-pyridylmethyl)(6-methyl-2-pyridylmethyl) aminomethyl)-4-bromophenolat) ; _chemical_name_common ; Manganese(ii)-di-chloro-2-(2-pyridylmethyl)(6-methyl-2- pyridylmethyl) aminomethyl)-4-bromophenolat) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 Br3 Mn N3 O' _chemical_formula_weight 599.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.523(3) _cell_length_b 17.092(3) _cell_length_c 18.230(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4213.6(15) _cell_formula_units_Z 8 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.889 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2328 _exptl_absorpt_coefficient_mu 6.330 _exptl_absorpt_correction_type 'DECAY, STOE IPDS software package' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS System' _diffrn_measurement_method phi-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28464 _diffrn_reflns_av_R_equivalents 0.1594 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4079 _reflns_number_gt 2451 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS software package' _computing_cell_refinement 'STOE IPDS software package' _computing_data_reduction 'STOE IPDS software package' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+23.5579P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4079 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1201 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1669 _refine_ls_wR_factor_gt 0.1340 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 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 0.27906(10) 0.27326(7) 0.54100(6) 0.0366(3) Uani 1 1 d . . . Br1 Br 0.11575(7) 0.22290(6) 0.60271(4) 0.0483(3) Uani 1 1 d . . . Br2 Br 0.36384(9) 0.14723(6) 0.50049(6) 0.0615(3) Uani 1 1 d . . . N1 N 0.2386(5) 0.4045(4) 0.5606(3) 0.0361(16) Uani 1 1 d . . . N2 N 0.2079(5) 0.3152(4) 0.4390(3) 0.0397(17) Uani 1 1 d . . . N3 N 0.3355(5) 0.3033(4) 0.6518(3) 0.0380(16) Uani 1 1 d . . . O1 O 0.4253(5) 0.3356(3) 0.4953(3) 0.0455(15) Uani 1 1 d . . . H1C H 0.4642 0.2996 0.4855 0.068 Uiso 1 1 calc R . . C1 C 0.1457(8) 0.4149(5) 0.5199(5) 0.051(2) Uani 1 1 d . . . H1A H 0.1300 0.4707 0.5163 0.061 Uiso 1 1 calc R . . H1B H 0.0917 0.3889 0.5461 0.061 Uiso 1 1 calc R . . C2 C 0.1550(7) 0.3810(6) 0.4446(5) 0.047(2) Uani 1 1 d . . . C3 C 0.1103(9) 0.4149(8) 0.3828(7) 0.074(4) Uani 1 1 d . . . H3A H 0.0751 0.4622 0.3867 0.088 Uiso 1 1 calc R . . C4 C 0.1195(10) 0.3772(10) 0.3157(6) 0.081(4) Uani 1 1 d . . . H4A H 0.0873 0.3971 0.2740 0.098 Uiso 1 1 calc R . . C5 C 0.1748(10) 0.3119(9) 0.3108(6) 0.079(4) Uani 1 1 d . . . H5A H 0.1838 0.2870 0.2653 0.095 Uiso 1 1 calc R . . C6 C 0.2178(8) 0.2821(7) 0.3730(5) 0.057(3) Uani 1 1 d . . . H6A H 0.2559 0.2363 0.3691 0.068 Uiso 1 1 calc R . . C7 C 0.2245(7) 0.4133(5) 0.6405(4) 0.042(2) Uani 1 1 d . . . H7A H 0.1587 0.3940 0.6540 0.051 Uiso 1 1 calc R . . H7B H 0.2280 0.4688 0.6535 0.051 Uiso 1 1 calc R . . C8 C 0.3020(7) 0.3687(5) 0.6829(4) 0.041(2) Uani 1 1 d . . . C9 C 0.3355(8) 0.3944(6) 0.7514(5) 0.054(3) Uani 1 1 d . . . H9A H 0.3122 0.4412 0.7723 0.065 Uiso 1 1 calc R . . C10 C 0.4038(9) 0.3485(8) 0.7866(5) 0.066(3) Uani 1 1 d . . . H10A H 0.4273 0.3638 0.8330 0.080 Uiso 1 1 calc R . . C11 C 0.4384(9) 0.2811(7) 0.7558(5) 0.067(3) Uani 1 1 d . . . H11A H 0.4856 0.2499 0.7798 0.080 Uiso 1 1 calc R . . C12 C 0.4018(8) 0.2608(6) 0.6888(5) 0.056(3) Uani 1 1 d . . . H12A H 0.4246 0.2142 0.6673 0.067 Uiso 1 1 calc R . . C13 C 0.3122(6) 0.4629(5) 0.5329(5) 0.0388(19) Uani 1 1 d . . . H13A H 0.3153 0.4591 0.4793 0.047 Uiso 1 1 calc R . . H13B H 0.2890 0.5155 0.5453 0.047 Uiso 1 1 calc R . . C14 C 0.4134(6) 0.4523(4) 0.5631(4) 0.0341(19) Uani 1 1 d . . . C15 C 0.4555(7) 0.5060(5) 0.6107(5) 0.042(2) Uani 1 1 d . . . H15A H 0.4201 0.5508 0.6251 0.050 Uiso 1 1 calc R . . C16 C 0.5507(7) 0.4929(5) 0.6368(4) 0.040(2) Uani 1 1 d . . . C17 C 0.6044(7) 0.4299(5) 0.6151(4) 0.044(2) Uani 1 1 d . . . H17A H 0.6691 0.4228 0.6327 0.053 Uiso 1 1 calc R . . C18 C 0.5644(7) 0.3768(5) 0.5675(5) 0.042(2) Uani 1 1 d . . . H18A H 0.6012 0.3329 0.5526 0.050 Uiso 1 1 calc R . . C19 C 0.4703(7) 0.3880(4) 0.5417(4) 0.0343(19) Uani 1 1 d . . . Br3 Br 0.60762(9) 0.56709(7) 0.70154(7) 0.0711(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0488(8) 0.0344(6) 0.0266(6) 0.0008(5) -0.0012(5) -0.0027(6) Br1 0.0560(6) 0.0540(5) 0.0348(4) -0.0022(4) 0.0063(4) -0.0137(5) Br2 0.0726(8) 0.0394(5) 0.0726(7) -0.0036(5) 0.0143(6) 0.0038(5) N1 0.042(4) 0.040(4) 0.026(3) 0.008(3) -0.004(3) 0.001(3) N2 0.036(4) 0.051(4) 0.032(4) 0.001(3) -0.006(3) -0.008(4) N3 0.045(4) 0.042(4) 0.027(3) 0.006(3) -0.001(3) -0.005(3) O1 0.057(4) 0.041(3) 0.039(3) -0.008(3) 0.006(3) -0.003(3) C1 0.064(7) 0.033(5) 0.055(6) 0.010(4) -0.003(5) 0.002(4) C2 0.037(5) 0.053(6) 0.050(5) 0.015(4) -0.002(4) -0.011(4) C3 0.057(7) 0.086(8) 0.078(8) 0.039(7) -0.021(6) -0.008(6) C4 0.070(9) 0.129(12) 0.045(7) 0.029(7) -0.026(6) -0.025(8) C5 0.071(9) 0.133(12) 0.033(5) 0.003(6) -0.012(5) -0.037(9) C6 0.052(6) 0.081(7) 0.038(5) -0.007(5) -0.005(4) -0.015(6) C7 0.043(6) 0.046(5) 0.038(4) -0.006(4) 0.012(4) -0.004(4) C8 0.047(6) 0.050(5) 0.027(4) -0.004(4) 0.010(4) -0.011(4) C9 0.069(7) 0.064(6) 0.029(4) -0.004(4) 0.004(4) -0.017(5) C10 0.065(8) 0.102(9) 0.031(5) 0.004(5) -0.009(5) -0.036(7) C11 0.070(8) 0.090(8) 0.040(5) 0.020(6) -0.014(5) -0.009(7) C12 0.059(7) 0.062(6) 0.046(5) 0.016(5) -0.002(5) -0.005(5) C13 0.039(5) 0.036(4) 0.041(5) 0.009(4) -0.005(4) -0.003(4) C14 0.044(5) 0.022(4) 0.036(4) 0.007(3) 0.010(3) -0.003(3) C15 0.058(6) 0.027(4) 0.041(5) -0.001(4) 0.003(4) -0.003(4) C16 0.054(6) 0.037(5) 0.028(4) -0.005(3) 0.003(4) -0.012(4) C17 0.048(6) 0.046(5) 0.039(5) 0.001(4) 0.000(4) 0.001(4) C18 0.042(6) 0.041(5) 0.042(5) 0.003(4) -0.001(4) 0.007(4) C19 0.046(5) 0.031(4) 0.026(4) 0.002(3) 0.002(3) -0.012(4) Br3 0.0619(7) 0.0724(7) 0.0791(8) -0.0332(6) -0.0081(6) -0.0089(6) _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 N2 2.213(7) . ? Mn1 N3 2.219(6) . ? Mn1 N1 2.337(7) . ? Mn1 O1 2.396(6) . ? Mn1 Br2 2.5495(17) . ? Mn1 Br1 2.6236(16) . ? N1 C1 1.469(12) . ? N1 C7 1.476(10) . ? N1 C13 1.497(10) . ? N2 C6 1.335(11) . ? N2 C2 1.337(12) . ? N3 C8 1.333(11) . ? N3 C12 1.336(12) . ? O1 C19 1.374(9) . ? C1 C2 1.494(13) . ? C2 C3 1.405(13) . ? C3 C4 1.388(18) . ? C4 C5 1.346(19) . ? C5 C6 1.374(15) . ? C7 C8 1.510(13) . ? C8 C9 1.399(12) . ? C9 C10 1.373(16) . ? C10 C11 1.364(17) . ? C11 C12 1.363(14) . ? C13 C14 1.487(12) . ? C14 C15 1.385(11) . ? C14 C19 1.398(11) . ? C15 C16 1.391(13) . ? C16 C17 1.359(12) . ? C16 Br3 1.895(8) . ? C17 C18 1.366(12) . ? C18 C19 1.370(12) . ? 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 N2 Mn1 N3 147.1(3) . . ? N2 Mn1 N1 73.5(2) . . ? N3 Mn1 N1 73.7(2) . . ? N2 Mn1 O1 85.5(2) . . ? N3 Mn1 O1 86.0(2) . . ? N1 Mn1 O1 79.6(2) . . ? N2 Mn1 Br2 103.0(2) . . ? N3 Mn1 Br2 107.72(19) . . ? N1 Mn1 Br2 163.91(18) . . ? O1 Mn1 Br2 84.48(15) . . ? N2 Mn1 Br1 95.78(19) . . ? N3 Mn1 Br1 88.57(18) . . ? N1 Mn1 Br1 92.99(18) . . ? O1 Mn1 Br1 171.81(15) . . ? Br2 Mn1 Br1 103.04(6) . . ? C1 N1 C7 112.1(7) . . ? C1 N1 C13 108.5(6) . . ? C7 N1 C13 110.5(6) . . ? C1 N1 Mn1 103.8(5) . . ? C7 N1 Mn1 106.2(5) . . ? C13 N1 Mn1 115.6(5) . . ? C6 N2 C2 118.7(8) . . ? C6 N2 Mn1 125.1(7) . . ? C2 N2 Mn1 116.1(6) . . ? C8 N3 C12 118.0(8) . . ? C8 N3 Mn1 117.7(6) . . ? C12 N3 Mn1 124.4(6) . . ? C19 O1 Mn1 116.2(5) . . ? N1 C1 C2 110.2(8) . . ? N2 C2 C3 121.0(10) . . ? N2 C2 C1 116.2(8) . . ? C3 C2 C1 122.7(10) . . ? C4 C3 C2 118.5(12) . . ? C5 C4 C3 119.6(11) . . ? C4 C5 C6 119.2(11) . . ? N2 C6 C5 123.0(12) . . ? N1 C7 C8 111.3(7) . . ? N3 C8 C9 122.2(9) . . ? N3 C8 C7 116.2(7) . . ? C9 C8 C7 121.5(8) . . ? C10 C9 C8 117.1(10) . . ? C11 C10 C9 121.4(9) . . ? C12 C11 C10 117.4(11) . . ? N3 C12 C11 123.9(11) . . ? C14 C13 N1 114.0(6) . . ? C15 C14 C19 118.0(8) . . ? C15 C14 C13 122.0(7) . . ? C19 C14 C13 120.0(7) . . ? C14 C15 C16 119.2(8) . . ? C17 C16 C15 121.5(8) . . ? C17 C16 Br3 119.7(7) . . ? C15 C16 Br3 118.8(7) . . ? C16 C17 C18 120.0(9) . . ? C17 C18 C19 119.6(8) . . ? C18 C19 O1 122.2(8) . . ? C18 C19 C14 121.7(8) . . ? O1 C19 C14 116.1(8) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.160 _refine_diff_density_min -0.983 _refine_diff_density_rms 0.144