# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Sung-Nak Choi' _publ_contact_author_email SUNACHOI@PUSAN.AC.KR _publ_section_title ; Selective Complexation of 3d Metal(II) Ions with Multidentate and Chiral Isomers Derived from Condensation of 2-Pyridinecarboxaldehyde with Triethylenetetramine ; loop_ _publ_author_name 'Sung-Nak Choi.' 'Hee Jung Choi.' 'Hee-Jin Iim.' 'Sung Kwon Kang.' ; Eun-Sook Kim ; 'Young-Inn Kim.' 'Yong-Min Lee.' # Attachment 'CCDC641979.cif' # data_Mn(edibPy)Cl2 _database_code_depnum_ccdc_archive 'CCDC 641979' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H24 Cl2 Mn N6' _chemical_formula_sum 'C18 H24 Cl2 Mn N6' _chemical_formula_weight 450.27 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' 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' N N 0.0061 0.0033 '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_space_group_name_Hall '-P 2yn' 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 10.8310(2) _cell_length_b 15.3580(2) _cell_length_c 12.2391(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.9500(10) _cell_angle_gamma 90.00 _cell_volume 2035.60(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 7007 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 0.927 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.692 _exptl_absorpt_correction_T_max 0.793 _exptl_absorpt_process_details 'SADABS 2.03, (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 18880 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4667 _reflns_number_gt 3655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.5926P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4667 _refine_ls_number_parameters 252 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0453 _refine_ls_R_factor_gt 0.0309 _refine_ls_wR_factor_ref 0.0777 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn 0.41610(2) 0.238550(17) 0.65612(2) 0.03322(9) Uani 1 1 d . . . Cl1 Cl 0.31622(4) 0.14991(4) 0.79511(4) 0.05017(13) Uani 1 1 d . . . Cl2 Cl 0.48138(5) 0.36330(3) 0.76973(5) 0.05384(14) Uani 1 1 d . . . N1 N 0.60151(13) 0.16586(10) 0.68101(13) 0.0402(4) Uani 1 1 d . . . C2 C 0.62015(18) 0.10299(13) 0.75455(17) 0.0491(5) Uani 1 1 d . . . H2 H 0.5546 0.0869 0.7983 0.059 Uiso 1 1 calc R . . C3 C 0.73142(19) 0.06054(14) 0.76929(19) 0.0553(5) Uani 1 1 d . . . H3 H 0.7401 0.0164 0.8208 0.066 Uiso 1 1 calc R . . C4 C 0.82870(18) 0.08504(14) 0.70627(19) 0.0539(5) Uani 1 1 d . . . H4 H 0.9049 0.0577 0.7143 0.065 Uiso 1 1 calc R . . C5 C 0.81219(16) 0.15044(13) 0.63106(18) 0.0481(5) Uani 1 1 d . . . H5 H 0.8775 0.1681 0.5879 0.058 Uiso 1 1 calc R . . C6 C 0.69771(15) 0.19003(11) 0.61977(15) 0.0376(4) Uani 1 1 d . . . C7 C 0.67506(15) 0.26290(12) 0.53990(17) 0.0408(4) Uani 1 1 d . . . H7 H 0.7280 0.2550 0.4765 0.049 Uiso 1 1 calc R . . N8 N 0.69836(15) 0.34762(11) 0.58779(18) 0.0485(4) Uani 1 1 d . . . H8 H 0.6648(18) 0.3492(12) 0.6482(17) 0.035(6) Uiso 1 1 d . . . C9 C 0.62440(19) 0.40867(13) 0.52052(19) 0.0537(5) Uani 1 1 d . . . H9A H 0.6767 0.4390 0.4694 0.064 Uiso 1 1 calc R . . H9B H 0.5848 0.4514 0.5666 0.064 Uiso 1 1 calc R . . C10 C 0.52757(18) 0.35468(13) 0.45906(18) 0.0499(5) Uani 1 1 d . . . H10A H 0.4452 0.3764 0.4727 0.060 Uiso 1 1 calc R . . H10B H 0.5418 0.3560 0.3810 0.060 Uiso 1 1 calc R . . N11 N 0.54285(12) 0.26520(9) 0.50259(13) 0.0368(3) Uani 1 1 d . . . C12 C 0.51530(17) 0.19745(14) 0.42070(16) 0.0465(5) Uani 1 1 d . . . H12A H 0.5521 0.1428 0.4439 0.056 Uiso 1 1 calc R . . H12B H 0.5510 0.2137 0.3515 0.056 Uiso 1 1 calc R . . C13 C 0.37717(17) 0.18591(14) 0.40604(15) 0.0456(4) Uani 1 1 d . . . H13A H 0.3402 0.2408 0.3840 0.055 Uiso 1 1 calc R . . H13B H 0.3607 0.1437 0.3487 0.055 Uiso 1 1 calc R . . N14 N 0.32113(13) 0.15603(9) 0.50863(12) 0.0369(3) Uani 1 1 d . . . C15 C 0.32944(19) 0.06007(12) 0.52599(19) 0.0522(5) Uani 1 1 d . . . H15A H 0.3895 0.0464 0.5831 0.063 Uiso 1 1 calc R . . H15B H 0.3532 0.0308 0.4593 0.063 Uiso 1 1 calc R . . C16 C 0.1994(2) 0.03226(14) 0.5597(2) 0.0676(7) Uani 1 1 d . . . H16A H 0.1588 0.0001 0.5011 0.081 Uiso 1 1 calc R . . H16B H 0.2035 -0.0044 0.6241 0.081 Uiso 1 1 calc R . . N17 N 0.13193(15) 0.11226(11) 0.58260(18) 0.0488(4) Uani 1 1 d . . . H17 H 0.1494(17) 0.1288(12) 0.6424(17) 0.033(6) Uiso 1 1 d . . . C18 C 0.18574(15) 0.17419(12) 0.50829(16) 0.0408(4) Uani 1 1 d . . . H18 H 0.1521 0.1636 0.4347 0.049 Uiso 1 1 calc R . . C19 C 0.15705(15) 0.26614(12) 0.54058(15) 0.0374(4) Uani 1 1 d . . . C20 C 0.04351(16) 0.30211(14) 0.51203(18) 0.0501(5) Uani 1 1 d . . . H20 H -0.0118 0.2714 0.4677 0.060 Uiso 1 1 calc R . . C21 C 0.01379(19) 0.38307(15) 0.5498(2) 0.0624(6) Uani 1 1 d . . . H21 H -0.0629 0.4075 0.5335 0.075 Uiso 1 1 calc R . . C22 C 0.0994(2) 0.42773(14) 0.6124(2) 0.0621(6) Uani 1 1 d . . . H22 H 0.0816 0.4830 0.6388 0.074 Uiso 1 1 calc R . . C23 C 0.21154(18) 0.38947(13) 0.63529(19) 0.0512(5) Uani 1 1 d . . . H23 H 0.2696 0.4206 0.6763 0.061 Uiso 1 1 calc R . . N24 N 0.24105(13) 0.30938(10) 0.60132(13) 0.0397(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 Mn 0.02907(13) 0.03764(15) 0.03282(16) -0.00184(11) -0.00363(10) 0.00478(10) Cl1 0.0433(2) 0.0668(3) 0.0405(3) 0.0071(2) 0.00423(19) -0.0006(2) Cl2 0.0513(3) 0.0555(3) 0.0541(3) -0.0178(2) -0.0169(2) 0.0053(2) N1 0.0339(7) 0.0417(8) 0.0450(10) 0.0065(7) 0.0019(6) 0.0058(6) C2 0.0449(10) 0.0512(11) 0.0511(13) 0.0146(10) 0.0013(9) 0.0061(9) C3 0.0534(12) 0.0534(12) 0.0587(14) 0.0140(10) -0.0101(10) 0.0135(10) C4 0.0387(10) 0.0556(12) 0.0671(15) -0.0025(11) -0.0112(9) 0.0146(9) C5 0.0301(8) 0.0507(11) 0.0633(14) -0.0010(10) -0.0004(8) 0.0041(8) C6 0.0316(8) 0.0367(9) 0.0444(11) -0.0004(8) -0.0006(7) 0.0013(7) C7 0.0291(8) 0.0430(10) 0.0506(12) 0.0054(9) 0.0034(7) -0.0002(7) N8 0.0404(8) 0.0423(9) 0.0626(13) 0.0049(9) -0.0037(8) -0.0060(7) C9 0.0572(12) 0.0382(10) 0.0657(15) 0.0097(10) -0.0008(10) -0.0007(9) C10 0.0466(10) 0.0474(11) 0.0555(13) 0.0152(10) -0.0033(9) 0.0010(9) N11 0.0332(7) 0.0378(8) 0.0391(9) 0.0026(7) -0.0016(6) 0.0013(6) C12 0.0458(10) 0.0556(12) 0.0383(11) -0.0053(9) 0.0063(8) 0.0005(9) C13 0.0495(10) 0.0549(12) 0.0324(11) -0.0064(9) -0.0026(8) -0.0023(9) N14 0.0372(7) 0.0376(8) 0.0359(9) -0.0040(7) -0.0015(6) 0.0000(6) C15 0.0586(12) 0.0382(10) 0.0599(14) -0.0085(10) -0.0009(10) 0.0027(9) C16 0.0731(15) 0.0406(11) 0.0894(19) -0.0061(12) 0.0149(13) -0.0101(11) N17 0.0461(9) 0.0437(10) 0.0565(13) -0.0040(9) 0.0006(8) -0.0100(7) C18 0.0349(8) 0.0478(10) 0.0395(11) -0.0043(8) -0.0081(7) -0.0054(8) C19 0.0307(8) 0.0428(10) 0.0385(10) 0.0075(8) -0.0060(7) -0.0017(7) C20 0.0335(9) 0.0544(12) 0.0619(14) 0.0181(10) -0.0131(8) -0.0029(8) C21 0.0373(10) 0.0578(14) 0.0918(19) 0.0194(13) -0.0076(11) 0.0126(9) C22 0.0537(12) 0.0450(12) 0.0874(18) 0.0000(12) -0.0057(11) 0.0179(10) C23 0.0461(10) 0.0416(11) 0.0655(15) -0.0073(10) -0.0113(9) 0.0089(9) N24 0.0338(7) 0.0384(8) 0.0465(10) -0.0037(7) -0.0096(6) 0.0053(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 Mn N24 2.2773(14) . ? Mn N1 2.3134(14) . ? Mn N11 2.3809(15) . ? Mn N14 2.4210(15) . ? Mn Cl1 2.4451(5) . ? Mn Cl2 2.4640(5) . ? N1 C2 1.333(2) . ? N1 C6 1.346(2) . ? C2 C3 1.379(3) . ? C2 H2 0.9300 . ? C3 C4 1.369(3) . ? C3 H3 0.9300 . ? C4 C5 1.372(3) . ? C4 H4 0.9300 . ? C5 C6 1.386(2) . ? C5 H5 0.9300 . ? C6 C7 1.503(3) . ? C7 N8 1.447(3) . ? C7 N11 1.496(2) . ? C7 H7 0.9800 . ? N8 C9 1.475(3) . ? N8 H8 0.83(2) . ? C9 C10 1.525(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N11 1.482(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N11 C12 1.472(2) . ? C12 C13 1.514(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N14 1.477(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N14 C15 1.492(2) . ? N14 C18 1.493(2) . ? C15 C16 1.535(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N17 1.459(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N17 C18 1.445(3) . ? N17 H17 0.80(2) . ? C18 C19 1.500(3) . ? C18 H18 0.9800 . ? C19 N24 1.341(2) . ? C19 C20 1.387(2) . ? C20 C21 1.367(3) . ? C20 H20 0.9300 . ? C21 C22 1.376(3) . ? C21 H21 0.9300 . ? C22 C23 1.374(3) . ? C22 H22 0.9300 . ? C23 N24 1.339(2) . ? C23 H23 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N24 Mn N1 170.40(6) . . ? N24 Mn N11 100.00(5) . . ? N1 Mn N11 71.11(5) . . ? N24 Mn N14 71.88(5) . . ? N1 Mn N14 101.70(5) . . ? N11 Mn N14 75.22(5) . . ? N24 Mn Cl1 95.45(4) . . ? N1 Mn Cl1 91.88(4) . . ? N11 Mn Cl1 155.83(4) . . ? N14 Mn Cl1 92.28(4) . . ? N24 Mn Cl2 91.40(4) . . ? N1 Mn Cl2 93.48(4) . . ? N11 Mn Cl2 98.51(4) . . ? N14 Mn Cl2 160.42(4) . . ? Cl1 Mn Cl2 99.58(2) . . ? C2 N1 C6 117.77(15) . . ? C2 N1 Mn 124.04(12) . . ? C6 N1 Mn 118.16(11) . . ? N1 C2 C3 123.55(19) . . ? N1 C2 H2 118.2 . . ? C3 C2 H2 118.2 . . ? C4 C3 C2 118.39(19) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C3 C4 C5 119.10(18) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 119.63(18) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? N1 C6 C5 121.55(17) . . ? N1 C6 C7 116.62(14) . . ? C5 C6 C7 121.83(16) . . ? N8 C7 N11 105.19(14) . . ? N8 C7 C6 112.36(17) . . ? N11 C7 C6 111.16(14) . . ? N8 C7 H7 109.3 . . ? N11 C7 H7 109.3 . . ? C6 C7 H7 109.3 . . ? C7 N8 C9 104.82(16) . . ? C7 N8 H8 108.1(13) . . ? C9 N8 H8 103.7(14) . . ? N8 C9 C10 106.99(16) . . ? N8 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? N8 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.6 . . ? N11 C10 C9 104.77(15) . . ? N11 C10 H10A 110.8 . . ? C9 C10 H10A 110.8 . . ? N11 C10 H10B 110.8 . . ? C9 C10 H10B 110.8 . . ? H10A C10 H10B 108.9 . . ? C12 N11 C10 112.98(15) . . ? C12 N11 C7 111.93(14) . . ? C10 N11 C7 103.42(13) . . ? C12 N11 Mn 107.63(11) . . ? C10 N11 Mn 112.38(11) . . ? C7 N11 Mn 108.45(11) . . ? N11 C12 C13 110.62(15) . . ? N11 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N11 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? N14 C13 C12 110.79(15) . . ? N14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? N14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 N14 C15 113.79(15) . . ? C13 N14 C18 110.93(14) . . ? C15 N14 C18 104.00(14) . . ? C13 N14 Mn 107.20(10) . . ? C15 N14 Mn 112.78(12) . . ? C18 N14 Mn 108.04(10) . . ? N14 C15 C16 105.05(16) . . ? N14 C15 H15A 110.7 . . ? C16 C15 H15A 110.7 . . ? N14 C15 H15B 110.7 . . ? C16 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? N17 C16 C15 106.37(16) . . ? N17 C16 H16A 110.5 . . ? C15 C16 H16A 110.5 . . ? N17 C16 H16B 110.5 . . ? C15 C16 H16B 110.5 . . ? H16A C16 H16B 108.6 . . ? C18 N17 C16 102.99(17) . . ? C18 N17 H17 106.0(14) . . ? C16 N17 H17 109.5(14) . . ? N17 C18 N14 106.36(15) . . ? N17 C18 C19 111.48(16) . . ? N14 C18 C19 112.51(14) . . ? N17 C18 H18 108.8 . . ? N14 C18 H18 108.8 . . ? C19 C18 H18 108.8 . . ? N24 C19 C20 122.18(18) . . ? N24 C19 C18 118.06(14) . . ? C20 C19 C18 119.67(16) . . ? C21 C20 C19 119.33(19) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C20 C21 C22 118.78(18) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C23 C22 C21 119.1(2) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? N24 C23 C22 122.98(19) . . ? N24 C23 H23 118.5 . . ? C22 C23 H23 118.5 . . ? C23 N24 C19 117.63(15) . . ? C23 N24 Mn 123.32(12) . . ? C19 N24 Mn 118.72(11) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 Cl2 0.83(2) 2.51(2) 3.273(2) 153.2(18) . N17 H17 Cl1 0.80(2) 2.60(2) 3.303(2) 148.7(17) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.284 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.045 # Attachment 'CCDC641980.cif' # data_Mn(edibPy)(NCS)2 _database_code_depnum_ccdc_archive 'CCDC 641980' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C20 H24 Mn N8 S2' _chemical_formula_sum 'C20 H24 Mn N8 S2' _chemical_formula_weight 495.53 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' S S 0.1246 0.1234 '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 monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 15.4649(8) _cell_length_b 17.7127(10) _cell_length_c 16.6848(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.3730(10) _cell_angle_gamma 90.00 _cell_volume 4570.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 1791 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 18.77 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2056 _exptl_absorpt_coefficient_mu 0.785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 0.886 _exptl_absorpt_process_details 'SADABS 2.03, (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 SMART CCD area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39391 _diffrn_reflns_av_R_equivalents 0.1375 _diffrn_reflns_av_sigmaI/netI 0.1081 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8514 _reflns_number_gt 3977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SMART' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0482P)^2^+2.3467P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8514 _refine_ls_number_parameters 574 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1545 _refine_ls_R_factor_gt 0.0590 _refine_ls_wR_factor_ref 0.1506 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.72113(5) 0.75525(5) 0.18471(5) 0.0424(2) Uani 1 1 d . . . N1 N 0.6328(3) 0.8177(2) 0.0925(3) 0.0472(12) Uani 1 1 d . . . C2 C 0.6525(4) 0.8831(3) 0.0577(4) 0.0600(17) Uani 1 1 d . . . H2 H 0.7044 0.9062 0.0720 0.072 Uiso 1 1 calc R . . C3 C 0.6013(4) 0.9183(4) 0.0023(4) 0.0645(18) Uani 1 1 d . . . H3 H 0.6179 0.9638 -0.0208 0.077 Uiso 1 1 calc R . . C4 C 0.5248(4) 0.8847(4) -0.0181(4) 0.0656(18) Uani 1 1 d . . . H4 H 0.4882 0.9068 -0.0557 0.079 Uiso 1 1 calc R . . C5 C 0.5027(4) 0.8173(4) 0.0179(4) 0.0580(16) Uani 1 1 d . . . H5 H 0.4507 0.7936 0.0051 0.070 Uiso 1 1 calc R . . C6 C 0.5588(3) 0.7854(3) 0.0735(3) 0.0424(13) Uani 1 1 d . . . C7 C 0.5399(3) 0.7112(3) 0.1131(3) 0.0526(16) Uani 1 1 d . . . H7 H 0.4773 0.7076 0.1208 0.063 Uiso 1 1 calc R . . N8 N 0.5672(4) 0.6465(3) 0.0666(3) 0.0673(16) Uani 1 1 d . . . H8 H 0.623(3) 0.654(3) 0.052(3) 0.037(16) Uiso 1 1 d . . . C9 C 0.5708(5) 0.5851(4) 0.1259(5) 0.087(2) Uani 1 1 d . . . H9A H 0.6182 0.5510 0.1139 0.105 Uiso 1 1 calc R . . H9B H 0.5173 0.5565 0.1251 0.105 Uiso 1 1 calc R . . C10 C 0.5843(4) 0.6209(3) 0.2065(4) 0.0653(18) Uani 1 1 d . . . H10A H 0.5389 0.6062 0.2431 0.078 Uiso 1 1 calc R . . H10B H 0.6397 0.6062 0.2292 0.078 Uiso 1 1 calc R . . N11 N 0.5818(3) 0.7044(2) 0.1913(3) 0.0438(11) Uani 1 1 d . . . C12 C 0.5344(3) 0.7458(3) 0.2540(3) 0.0508(14) Uani 1 1 d . . . H12A H 0.4827 0.7179 0.2683 0.061 Uiso 1 1 calc R . . H12B H 0.5168 0.7948 0.2337 0.061 Uiso 1 1 calc R . . C13 C 0.5903(3) 0.7561(3) 0.3271(3) 0.0559(15) Uani 1 1 d . . . H13A H 0.5574 0.7811 0.3687 0.067 Uiso 1 1 calc R . . H13B H 0.6082 0.7071 0.3472 0.067 Uiso 1 1 calc R . . N14 N 0.6679(3) 0.8020(2) 0.3077(3) 0.0471(12) Uani 1 1 d . . . C15 C 0.6509(4) 0.8842(3) 0.3066(4) 0.0681(18) Uani 1 1 d . . . H15A H 0.6086 0.8978 0.3466 0.082 Uiso 1 1 calc R . . H15B H 0.6300 0.9002 0.2543 0.082 Uiso 1 1 calc R . . C16 C 0.7378(4) 0.9196(4) 0.3254(4) 0.077(2) Uani 1 1 d . . . H16A H 0.7621 0.9427 0.2779 0.092 Uiso 1 1 calc R . . H16B H 0.7322 0.9578 0.3667 0.092 Uiso 1 1 calc R . . N17 N 0.7932(4) 0.8562(3) 0.3538(3) 0.0658(15) Uani 1 1 d D . . H17 H 0.801(4) 0.880(3) 0.399(2) 0.079 Uiso 1 1 d D . . C18 C 0.7351(4) 0.7938(4) 0.3702(3) 0.0554(16) Uani 1 1 d . . . H18 H 0.7098 0.7991 0.4236 0.066 Uiso 1 1 calc R . . C19 C 0.7827(3) 0.7192(3) 0.3632(3) 0.0495(15) Uani 1 1 d . . . C20 C 0.8208(4) 0.6870(4) 0.4284(4) 0.0659(18) Uani 1 1 d . . . H20 H 0.8163 0.7094 0.4786 0.079 Uiso 1 1 calc R . . C21 C 0.8664(4) 0.6200(4) 0.4189(4) 0.075(2) Uani 1 1 d . . . H21 H 0.8928 0.5969 0.4628 0.090 Uiso 1 1 calc R . . C22 C 0.8721(4) 0.5890(4) 0.3454(4) 0.0676(18) Uani 1 1 d . . . H22 H 0.9029 0.5445 0.3376 0.081 Uiso 1 1 calc R . . C23 C 0.8311(3) 0.6243(3) 0.2820(4) 0.0564(16) Uani 1 1 d . . . H23 H 0.8342 0.6021 0.2315 0.068 Uiso 1 1 calc R . . N24 N 0.7873(3) 0.6892(3) 0.2896(3) 0.0483(12) Uani 1 1 d . . . N25 N 0.7682(3) 0.6701(3) 0.1012(3) 0.0624(14) Uani 1 1 d . . . C26 C 0.8018(4) 0.6199(4) 0.0709(3) 0.0556(16) Uani 1 1 d . . . S27 S 0.85096(15) 0.54982(11) 0.02710(11) 0.0918(7) Uani 1 1 d . . . N28 N 0.8226(3) 0.8332(3) 0.1605(3) 0.0578(14) Uani 1 1 d . . . C29 C 0.8683(4) 0.8828(3) 0.1483(3) 0.0463(14) Uani 1 1 d . . . S30 S 0.93339(11) 0.95222(10) 0.13098(11) 0.0716(5) Uani 1 1 d . . . Mn2 Mn 0.21731(5) 0.75361(4) 0.12826(5) 0.0409(2) Uani 1 1 d . . . N31 N 0.2844(3) 0.6976(3) 0.0224(3) 0.0476(12) Uani 1 1 d . . . C32 C 0.3315(4) 0.6345(4) 0.0263(3) 0.0561(16) Uani 1 1 d . . . H32 H 0.3345 0.6094 0.0752 0.067 Uiso 1 1 calc R . . C33 C 0.3759(4) 0.6043(4) -0.0371(5) 0.074(2) Uani 1 1 d . . . H33 H 0.4083 0.5604 -0.0311 0.089 Uiso 1 1 calc R . . C34 C 0.3710(5) 0.6407(5) -0.1091(5) 0.081(2) Uani 1 1 d . . . H34 H 0.4009 0.6221 -0.1531 0.097 Uiso 1 1 calc R . . C35 C 0.3221(4) 0.7043(4) -0.1162(4) 0.0694(19) Uani 1 1 d . . . H35 H 0.3171 0.7290 -0.1652 0.083 Uiso 1 1 calc R . . C36 C 0.2799(4) 0.7318(3) -0.0487(3) 0.0532(16) Uani 1 1 d . . . C37 C 0.2293(4) 0.8052(4) -0.0525(3) 0.0579(16) Uani 1 1 d . . . H37 H 0.2043 0.8122 -0.1061 0.069 Uiso 1 1 calc R . . N38 N 0.2831(4) 0.8696(3) -0.0310(4) 0.0685(16) Uani 1 1 d . . . H38 H 0.322(4) 0.878(3) -0.073(4) 0.07(2) Uiso 1 1 d . . . C39 C 0.2272(4) 0.9276(4) 0.0024(5) 0.080(2) Uani 1 1 d . . . H39A H 0.2218 0.9699 -0.0342 0.096 Uiso 1 1 calc R . . H39B H 0.2502 0.9458 0.0531 0.096 Uiso 1 1 calc R . . C40 C 0.1401(4) 0.8894(3) 0.0144(4) 0.0712(19) Uani 1 1 d . . . H40A H 0.1163 0.9017 0.0664 0.085 Uiso 1 1 calc R . . H40B H 0.0992 0.9044 -0.0270 0.085 Uiso 1 1 calc R . . N41 N 0.1608(3) 0.8068(3) 0.0085(3) 0.0486(12) Uani 1 1 d . . . C42 C 0.0860(3) 0.7597(4) -0.0157(3) 0.0592(16) Uani 1 1 d . . . H42A H 0.1063 0.7122 -0.0374 0.071 Uiso 1 1 calc R . . H42B H 0.0530 0.7855 -0.0571 0.071 Uiso 1 1 calc R . . C43 C 0.0294(3) 0.7450(3) 0.0551(3) 0.0546(15) Uani 1 1 d . . . H43A H 0.0105 0.7926 0.0777 0.065 Uiso 1 1 calc R . . H43B H -0.0215 0.7172 0.0379 0.065 Uiso 1 1 calc R . . N44 N 0.0768(3) 0.7009(2) 0.1170(3) 0.0428(11) Uani 1 1 d . . . C45 C 0.0814(4) 0.6181(3) 0.1012(4) 0.0640(18) Uani 1 1 d . . . H45A H 0.1387 0.6038 0.0832 0.077 Uiso 1 1 calc R . . H45B H 0.0394 0.6033 0.0607 0.077 Uiso 1 1 calc R . . C46 C 0.0610(5) 0.5815(3) 0.1818(4) 0.082(2) Uani 1 1 d . . . H46A H 0.0053 0.5564 0.1793 0.098 Uiso 1 1 calc R . . H46B H 0.1048 0.5443 0.1954 0.098 Uiso 1 1 calc R . . N47 N 0.0596(4) 0.6412(3) 0.2421(4) 0.0653(15) Uani 1 1 d D . . H47 H 0.109(2) 0.641(4) 0.264(4) 0.09(3) Uiso 1 1 d D . . C48 C 0.0329(4) 0.7072(3) 0.1958(3) 0.0504(15) Uani 1 1 d . . . H48 H -0.0298 0.7052 0.1872 0.061 Uiso 1 1 calc R . . C49 C 0.0556(4) 0.7798(3) 0.2384(3) 0.0457(14) Uani 1 1 d . . . C50 C 0.0008(4) 0.8111(4) 0.2940(4) 0.0588(17) Uani 1 1 d . . . H50 H -0.0523 0.7887 0.3044 0.071 Uiso 1 1 calc R . . C51 C 0.0253(5) 0.8764(4) 0.3345(4) 0.0696(19) Uani 1 1 d . . . H51 H -0.0106 0.8975 0.3730 0.083 Uiso 1 1 calc R . . C52 C 0.1031(5) 0.9090(4) 0.3167(4) 0.0653(18) Uani 1 1 d . . . H52 H 0.1211 0.9529 0.3426 0.078 Uiso 1 1 calc R . . C53 C 0.1534(4) 0.8758(3) 0.2604(4) 0.0598(17) Uani 1 1 d . . . H53 H 0.2060 0.8984 0.2483 0.072 Uiso 1 1 calc R . . N54 N 0.1320(3) 0.8121(3) 0.2212(3) 0.0483(12) Uani 1 1 d . . . N55 N 0.3196(3) 0.8292(3) 0.1565(3) 0.0614(14) Uani 1 1 d . . . C56 C 0.3664(4) 0.8794(3) 0.1693(3) 0.0485(15) Uani 1 1 d . . . S57 S 0.43311(12) 0.94782(9) 0.18685(10) 0.0703(5) Uani 1 1 d . . . N58 N 0.2619(3) 0.6655(3) 0.2069(3) 0.0611(14) Uani 1 1 d . . . C59 C 0.3054(4) 0.6232(3) 0.2410(3) 0.0462(14) Uani 1 1 d . . . S60 S 0.36705(11) 0.56393(9) 0.28993(11) 0.0689(5) 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 0.0433(5) 0.0446(5) 0.0391(5) 0.0054(4) 0.0006(4) 0.0002(4) N1 0.047(3) 0.043(3) 0.052(3) 0.010(2) -0.007(2) -0.004(2) C2 0.050(4) 0.064(4) 0.065(4) 0.022(4) -0.004(3) 0.002(3) C3 0.067(4) 0.059(4) 0.068(5) 0.024(3) 0.003(4) 0.003(4) C4 0.067(4) 0.078(5) 0.052(4) 0.016(4) -0.009(3) 0.020(4) C5 0.051(4) 0.070(5) 0.053(4) -0.010(3) -0.006(3) -0.002(3) C6 0.040(3) 0.045(3) 0.042(3) -0.004(3) -0.003(3) 0.006(3) C7 0.040(3) 0.055(4) 0.063(4) -0.001(3) -0.004(3) -0.012(3) N8 0.066(4) 0.057(4) 0.078(4) -0.020(3) -0.009(3) -0.003(3) C9 0.102(6) 0.044(4) 0.116(7) -0.008(4) -0.021(5) -0.004(4) C10 0.065(4) 0.035(4) 0.096(5) 0.009(4) 0.004(4) -0.004(3) N11 0.046(3) 0.039(3) 0.047(3) 0.004(2) 0.000(2) -0.002(2) C12 0.041(3) 0.052(4) 0.059(4) 0.013(3) 0.005(3) -0.007(3) C13 0.053(3) 0.063(4) 0.052(4) 0.009(3) 0.012(3) 0.007(3) N14 0.049(3) 0.046(3) 0.047(3) -0.001(2) 0.003(2) 0.004(2) C15 0.073(4) 0.049(4) 0.082(5) -0.004(3) -0.002(4) 0.003(4) C16 0.077(5) 0.060(4) 0.093(6) -0.017(4) -0.023(4) 0.003(4) N17 0.068(3) 0.056(4) 0.074(4) -0.020(3) -0.019(3) -0.004(3) C18 0.058(4) 0.071(4) 0.038(4) -0.007(3) -0.001(3) 0.012(4) C19 0.044(3) 0.069(4) 0.035(4) 0.006(3) 0.000(3) 0.004(3) C20 0.066(4) 0.091(5) 0.040(4) 0.018(4) -0.005(3) 0.007(4) C21 0.065(4) 0.093(6) 0.068(5) 0.041(4) -0.014(4) 0.003(4) C22 0.061(4) 0.065(4) 0.077(5) 0.007(4) -0.003(4) 0.014(4) C23 0.048(3) 0.060(4) 0.062(4) 0.011(3) -0.002(3) 0.013(3) N24 0.049(3) 0.052(3) 0.043(3) 0.007(2) 0.003(2) 0.012(2) N25 0.077(4) 0.061(4) 0.049(3) -0.009(3) 0.008(3) 0.002(3) C26 0.073(4) 0.057(4) 0.037(4) 0.009(3) -0.010(3) 0.002(4) S27 0.1462(19) 0.0692(12) 0.0600(12) -0.0065(10) -0.0100(12) 0.0422(13) N28 0.049(3) 0.067(4) 0.057(3) 0.009(3) -0.007(3) -0.009(3) C29 0.048(3) 0.050(4) 0.041(4) 0.004(3) -0.015(3) 0.002(3) S30 0.0712(11) 0.0635(11) 0.0800(13) 0.0118(9) -0.0118(9) -0.0222(9) Mn2 0.0402(4) 0.0429(5) 0.0397(5) -0.0036(4) -0.0021(3) -0.0002(4) N31 0.053(3) 0.052(3) 0.038(3) -0.005(2) -0.002(2) 0.000(3) C32 0.061(4) 0.065(4) 0.042(4) -0.010(3) 0.005(3) 0.008(3) C33 0.074(5) 0.072(5) 0.076(5) -0.025(4) -0.003(4) 0.014(4) C34 0.074(5) 0.105(6) 0.063(5) -0.029(5) 0.019(4) -0.004(5) C35 0.067(4) 0.101(6) 0.040(4) -0.010(4) 0.007(3) -0.008(4) C36 0.049(3) 0.071(4) 0.039(4) -0.007(3) -0.002(3) -0.008(3) C37 0.061(4) 0.073(5) 0.040(4) 0.010(3) -0.003(3) 0.000(4) N38 0.056(3) 0.072(4) 0.078(4) 0.021(3) 0.009(3) -0.011(3) C39 0.071(5) 0.051(4) 0.117(6) 0.023(4) -0.011(4) -0.007(4) C40 0.077(5) 0.054(4) 0.083(5) 0.012(4) 0.004(4) 0.011(4) N41 0.043(3) 0.049(3) 0.053(3) 0.011(2) -0.004(2) -0.005(2) C42 0.048(3) 0.082(5) 0.048(4) 0.004(3) -0.014(3) 0.000(3) C43 0.047(3) 0.067(4) 0.050(4) 0.000(3) -0.010(3) -0.007(3) N44 0.046(3) 0.040(3) 0.043(3) -0.005(2) 0.003(2) -0.008(2) C45 0.066(4) 0.045(4) 0.081(5) -0.016(3) 0.009(4) -0.012(3) C46 0.095(5) 0.037(4) 0.113(7) -0.004(4) 0.018(5) -0.010(4) N47 0.077(4) 0.050(4) 0.069(4) 0.015(3) 0.020(4) -0.007(3) C48 0.047(3) 0.046(4) 0.059(4) 0.002(3) 0.011(3) 0.001(3) C49 0.048(3) 0.052(4) 0.037(3) 0.006(3) 0.001(3) 0.014(3) C50 0.055(4) 0.069(4) 0.052(4) 0.007(3) 0.008(3) 0.014(3) C51 0.085(5) 0.074(5) 0.049(4) -0.013(4) 0.006(4) 0.033(4) C52 0.079(5) 0.057(4) 0.059(4) -0.016(3) -0.008(4) 0.016(4) C53 0.058(4) 0.053(4) 0.068(5) -0.021(3) -0.004(3) -0.002(3) N54 0.042(3) 0.050(3) 0.054(3) -0.008(2) 0.000(2) 0.000(2) N55 0.058(3) 0.065(4) 0.062(4) -0.009(3) -0.001(3) -0.011(3) C56 0.051(4) 0.054(4) 0.041(4) 0.000(3) 0.005(3) 0.000(3) S57 0.0912(13) 0.0533(10) 0.0664(12) -0.0039(9) -0.0022(9) -0.0228(10) N58 0.066(3) 0.061(3) 0.056(4) 0.007(3) -0.003(3) 0.012(3) C59 0.054(4) 0.043(4) 0.042(4) -0.011(3) 0.007(3) -0.008(3) S60 0.0706(11) 0.0606(11) 0.0753(13) 0.0040(9) -0.0096(9) 0.0147(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 N28 2.131(5) . ? Mn1 N25 2.181(5) . ? Mn1 N1 2.330(4) . ? Mn1 N24 2.335(4) . ? Mn1 N11 2.339(4) . ? Mn1 N14 2.365(4) . ? N1 C6 1.316(6) . ? N1 C2 1.333(7) . ? C2 C3 1.363(7) . ? C2 H2 0.9300 . ? C3 C4 1.366(8) . ? C3 H3 0.9300 . ? C4 C5 1.380(8) . ? C4 H4 0.9300 . ? C5 C6 1.387(7) . ? C5 H5 0.9300 . ? C6 C7 1.500(8) . ? C7 N8 1.448(7) . ? C7 N11 1.458(6) . ? C7 H7 0.9800 . ? N8 C9 1.472(8) . ? N8 H8 0.91(5) . ? C9 C10 1.501(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N11 1.501(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N11 C12 1.477(6) . ? C12 C13 1.501(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N14 1.487(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N14 C18 1.475(6) . ? N14 C15 1.480(7) . ? C15 C16 1.513(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N17 1.487(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N17 C18 1.452(7) . ? N17 H17 0.86(2) . ? C18 C19 1.518(8) . ? C18 H18 0.9800 . ? C19 N24 1.341(6) . ? C19 C20 1.359(7) . ? C20 C21 1.390(9) . ? C20 H20 0.9300 . ? C21 C22 1.348(9) . ? C21 H21 0.9300 . ? C22 C23 1.380(8) . ? C22 H22 0.9300 . ? C23 N24 1.340(6) . ? C23 H23 0.9300 . ? N25 C26 1.149(7) . ? C26 S27 1.632(7) . ? N28 C29 1.147(6) . ? C29 S30 1.616(6) . ? Mn2 N55 2.124(5) . ? Mn2 N58 2.149(5) . ? Mn2 N31 2.281(4) . ? Mn2 N54 2.290(4) . ? Mn2 N41 2.372(4) . ? Mn2 N44 2.372(4) . ? N31 C36 1.334(7) . ? N31 C32 1.336(7) . ? C32 C33 1.373(8) . ? C32 H32 0.9300 . ? C33 C34 1.365(9) . ? C33 H33 0.9300 . ? C34 C35 1.362(9) . ? C34 H34 0.9300 . ? C35 C36 1.392(8) . ? C35 H35 0.9300 . ? C36 C37 1.520(8) . ? C37 N38 1.455(7) . ? C37 N41 1.473(7) . ? C37 H37 0.9800 . ? N38 C39 1.456(8) . ? N38 H38 0.94(6) . ? C39 C40 1.521(8) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 N41 1.501(7) . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? N41 C42 1.481(6) . ? C42 C43 1.497(7) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 N44 1.485(6) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? N44 C48 1.488(6) . ? N44 C45 1.492(6) . ? C45 C46 1.529(8) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 N47 1.459(8) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? N47 C48 1.459(7) . ? N47 H47 0.84(2) . ? C48 C49 1.509(7) . ? C48 H48 0.9800 . ? C49 N54 1.346(6) . ? C49 C50 1.377(7) . ? C50 C51 1.390(8) . ? C50 H50 0.9300 . ? C51 C52 1.370(8) . ? C51 H51 0.9300 . ? C52 C53 1.358(8) . ? C52 H52 0.9300 . ? C53 N54 1.344(6) . ? C53 H53 0.9300 . ? N55 C56 1.164(6) . ? C56 S57 1.617(6) . ? N58 C59 1.155(6) . ? C59 S60 1.633(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 N28 Mn1 N25 94.46(19) . . ? N28 Mn1 N1 89.80(17) . . ? N25 Mn1 N1 95.88(18) . . ? N28 Mn1 N24 98.48(17) . . ? N25 Mn1 N24 89.20(18) . . ? N1 Mn1 N24 169.94(16) . . ? N28 Mn1 N11 159.76(17) . . ? N25 Mn1 N11 94.31(17) . . ? N1 Mn1 N11 71.17(15) . . ? N24 Mn1 N11 99.85(15) . . ? N28 Mn1 N14 101.47(17) . . ? N25 Mn1 N14 156.27(17) . . ? N1 Mn1 N14 101.60(15) . . ? N24 Mn1 N14 71.26(16) . . ? N11 Mn1 N14 76.57(15) . . ? C6 N1 C2 118.3(5) . . ? C6 N1 Mn1 117.2(4) . . ? C2 N1 Mn1 124.5(4) . . ? N1 C2 C3 124.0(6) . . ? N1 C2 H2 118.0 . . ? C3 C2 H2 118.0 . . ? C2 C3 C4 117.9(6) . . ? C2 C3 H3 121.1 . . ? C4 C3 H3 121.1 . . ? C3 C4 C5 119.1(6) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 119.2(6) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? N1 C6 C5 121.5(5) . . ? N1 C6 C7 116.5(5) . . ? C5 C6 C7 121.9(5) . . ? N8 C7 N11 106.6(5) . . ? N8 C7 C6 113.5(5) . . ? N11 C7 C6 112.3(4) . . ? N8 C7 H7 108.1 . . ? N11 C7 H7 108.1 . . ? C6 C7 H7 108.1 . . ? C7 N8 C9 103.6(5) . . ? C7 N8 H8 107(3) . . ? C9 N8 H8 105(3) . . ? N8 C9 C10 107.1(5) . . ? N8 C9 H9A 110.3 . . ? C10 C9 H9A 110.3 . . ? N8 C9 H9B 110.3 . . ? C10 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? N11 C10 C9 105.2(5) . . ? N11 C10 H10A 110.7 . . ? C9 C10 H10A 110.7 . . ? N11 C10 H10B 110.7 . . ? C9 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? C7 N11 C12 111.9(4) . . ? C7 N11 C10 104.1(4) . . ? C12 N11 C10 112.4(4) . . ? C7 N11 Mn1 109.3(3) . . ? C12 N11 Mn1 107.7(3) . . ? C10 N11 Mn1 111.3(3) . . ? N11 C12 C13 110.5(4) . . ? N11 C12 H12A 109.6 . . ? C13 C12 H12A 109.6 . . ? N11 C12 H12B 109.6 . . ? C13 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N14 C13 C12 110.6(4) . . ? N14 C13 H13A 109.5 . . ? C12 C13 H13A 109.5 . . ? N14 C13 H13B 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C18 N14 C15 103.3(4) . . ? C18 N14 C13 111.0(4) . . ? C15 N14 C13 113.4(4) . . ? C18 N14 Mn1 109.3(3) . . ? C15 N14 Mn1 113.3(4) . . ? C13 N14 Mn1 106.5(3) . . ? N14 C15 C16 104.4(5) . . ? N14 C15 H15A 110.9 . . ? C16 C15 H15A 110.9 . . ? N14 C15 H15B 110.9 . . ? C16 C15 H15B 110.9 . . ? H15A C15 H15B 108.9 . . ? N17 C16 C15 105.2(5) . . ? N17 C16 H16A 110.7 . . ? C15 C16 H16A 110.7 . . ? N17 C16 H16B 110.7 . . ? C15 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? C18 N17 C16 106.2(5) . . ? C18 N17 H17 107(4) . . ? C16 N17 H17 89(4) . . ? N17 C18 N14 103.1(5) . . ? N17 C18 C19 110.4(5) . . ? N14 C18 C19 111.8(5) . . ? N17 C18 H18 110.5 . . ? N14 C18 H18 110.5 . . ? C19 C18 H18 110.5 . . ? N24 C19 C20 122.8(6) . . ? N24 C19 C18 116.3(5) . . ? C20 C19 C18 120.8(6) . . ? C19 C20 C21 119.0(6) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C22 C21 C20 119.2(6) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C21 C22 C23 118.7(6) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? N24 C23 C22 123.1(6) . . ? N24 C23 H23 118.4 . . ? C22 C23 H23 118.4 . . ? C23 N24 C19 117.1(5) . . ? C23 N24 Mn1 125.3(4) . . ? C19 N24 Mn1 117.6(4) . . ? C26 N25 Mn1 165.8(5) . . ? N25 C26 S27 178.8(6) . . ? C29 N28 Mn1 170.3(5) . . ? N28 C29 S30 179.5(6) . . ? N55 Mn2 N58 94.98(19) . . ? N55 Mn2 N31 96.00(17) . . ? N58 Mn2 N31 90.65(18) . . ? N55 Mn2 N54 89.76(17) . . ? N58 Mn2 N54 95.67(18) . . ? N31 Mn2 N54 171.06(16) . . ? N55 Mn2 N41 101.91(17) . . ? N58 Mn2 N41 156.64(18) . . ? N31 Mn2 N41 71.77(16) . . ? N54 Mn2 N41 100.38(16) . . ? N55 Mn2 N44 161.25(17) . . ? N58 Mn2 N44 93.01(17) . . ? N31 Mn2 N44 100.85(15) . . ? N54 Mn2 N44 72.56(15) . . ? N41 Mn2 N44 75.96(15) . . ? C36 N31 C32 116.6(5) . . ? C36 N31 Mn2 118.1(4) . . ? C32 N31 Mn2 125.3(4) . . ? N31 C32 C33 124.3(6) . . ? N31 C32 H32 117.8 . . ? C33 C32 H32 117.8 . . ? C34 C33 C32 118.0(7) . . ? C34 C33 H33 121.0 . . ? C32 C33 H33 121.0 . . ? C35 C34 C33 119.6(6) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C34 C35 C36 118.8(7) . . ? C34 C35 H35 120.6 . . ? C36 C35 H35 120.6 . . ? N31 C36 C35 122.7(6) . . ? N31 C36 C37 116.6(5) . . ? C35 C36 C37 120.6(6) . . ? N38 C37 N41 103.2(5) . . ? N38 C37 C36 111.6(5) . . ? N41 C37 C36 111.2(5) . . ? N38 C37 H37 110.3 . . ? N41 C37 H37 110.3 . . ? C36 C37 H37 110.3 . . ? C37 N38 C39 107.9(5) . . ? C37 N38 H38 108(4) . . ? C39 N38 H38 124(4) . . ? N38 C39 C40 105.4(5) . . ? N38 C39 H39A 110.7 . . ? C40 C39 H39A 110.7 . . ? N38 C39 H39B 110.7 . . ? C40 C39 H39B 110.7 . . ? H39A C39 H39B 108.8 . . ? N41 C40 C39 103.6(5) . . ? N41 C40 H40A 111.0 . . ? C39 C40 H40A 111.0 . . ? N41 C40 H40B 111.0 . . ? C39 C40 H40B 111.0 . . ? H40A C40 H40B 109.0 . . ? C37 N41 C42 111.4(4) . . ? C37 N41 C40 102.7(4) . . ? C42 N41 C40 113.6(4) . . ? C37 N41 Mn2 108.1(3) . . ? C42 N41 Mn2 106.8(3) . . ? C40 N41 Mn2 114.2(4) . . ? N41 C42 C43 110.1(5) . . ? N41 C42 H42A 109.6 . . ? C43 C42 H42A 109.6 . . ? N41 C42 H42B 109.6 . . ? C43 C42 H42B 109.6 . . ? H42A C42 H42B 108.1 . . ? N44 C43 C42 110.6(4) . . ? N44 C43 H43A 109.5 . . ? C42 C43 H43A 109.5 . . ? N44 C43 H43B 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 108.1 . . ? C43 N44 C48 110.5(4) . . ? C43 N44 C45 114.7(4) . . ? C48 N44 C45 104.7(4) . . ? C43 N44 Mn2 107.2(3) . . ? C48 N44 Mn2 108.9(3) . . ? C45 N44 Mn2 110.8(3) . . ? N44 C45 C46 104.5(5) . . ? N44 C45 H45A 110.9 . . ? C46 C45 H45A 110.9 . . ? N44 C45 H45B 110.9 . . ? C46 C45 H45B 110.9 . . ? H45A C45 H45B 108.9 . . ? N47 C46 C45 107.6(5) . . ? N47 C46 H46A 110.2 . . ? C45 C46 H46A 110.2 . . ? N47 C46 H46B 110.2 . . ? C45 C46 H46B 110.2 . . ? H46A C46 H46B 108.5 . . ? C48 N47 C46 102.8(5) . . ? C48 N47 H47 119(5) . . ? C46 N47 H47 106(5) . . ? N47 C48 N44 106.2(4) . . ? N47 C48 C49 111.7(5) . . ? N44 C48 C49 112.0(4) . . ? N47 C48 H48 109.0 . . ? N44 C48 H48 109.0 . . ? C49 C48 H48 109.0 . . ? N54 C49 C50 121.1(5) . . ? N54 C49 C48 117.7(5) . . ? C50 C49 C48 121.2(5) . . ? C49 C50 C51 119.7(6) . . ? C49 C50 H50 120.1 . . ? C51 C50 H50 120.1 . . ? C52 C51 C50 118.9(6) . . ? C52 C51 H51 120.6 . . ? C50 C51 H51 120.6 . . ? C53 C52 C51 118.3(6) . . ? C53 C52 H52 120.8 . . ? C51 C52 H52 120.8 . . ? N54 C53 C52 124.1(6) . . ? N54 C53 H53 118.0 . . ? C52 C53 H53 118.0 . . ? C53 N54 C49 117.8(5) . . ? C53 N54 Mn2 124.6(4) . . ? C49 N54 Mn2 117.5(4) . . ? C56 N55 Mn2 169.4(5) . . ? N55 C56 S57 178.8(5) . . ? C59 N58 Mn2 162.8(5) . . ? N58 C59 S60 179.5(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8 N25 0.91(5) 2.39(5) 3.185(8) 145(4) . N17 H17 S27 0.86(2) 2.59(2) 3.449(5) 171(5) 4_576 N38 H38 S60 0.94(6) 2.61(6) 3.470(6) 153(5) 4_575 N47 H47 N58 0.84(2) 2.60(6) 3.215(8) 131(6) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.566 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.068 # Attachment 'CCDC641982_revised.cif' data_Cu(edibPy)Br2 _database_code_depnum_ccdc_archive 'CCDC 641982' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dibromo(2,2'-[1,2-ethanediylbis(1,3-diazolidine-2-yl)]bis-pyridine)copper(II) monohydrate ; _chemical_name_common ; dibromo(2,2'-(1,2-ethanediylbis(1,3-diazolidine-2-yl))bis- pyridine)copper(ii) monohydrate ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 Br Cu N6, H2 O, Br' _chemical_formula_sum 'C18 H26 Br2 Cu N6 O' _chemical_formula_weight 565.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab' 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 8.0217(6) _cell_length_b 8.9627(7) _cell_length_c 29.924(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2151.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6368 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.20 _exptl_crystal_description block _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.747 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 4.751 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.268 _exptl_absorpt_correction_T_max 0.310 _exptl_absorpt_process_details 'SADABS 2.03, (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13157 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4852 _reflns_number_gt 4274 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack (1983), 2027 Friedel pairs' _chemical_absolute_configuration ad _refine_ls_abs_structure_Flack 0.008(8) _refine_ls_number_reflns 4852 _refine_ls_number_parameters 265 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu 0.53163(4) 0.67318(3) 0.607982(10) 0.02944(8) Uani 1 1 d . . . Br1 Br 0.65176(4) 0.82338(3) 0.543456(9) 0.04448(8) Uani 1 1 d . . . N1 N 0.3198(3) 0.7906(2) 0.60825(8) 0.0363(5) Uani 1 1 d . . . C2 C 0.2280(4) 0.8233(3) 0.57205(11) 0.0462(7) Uani 1 1 d . . . H2 H 0.2594 0.7849 0.5444 0.055 Uiso 1 1 calc R . . C3 C 0.0884(4) 0.9124(4) 0.57483(14) 0.0586(10) Uani 1 1 d . . . H3 H 0.0237 0.9313 0.5497 0.070 Uiso 1 1 calc R . . C4 C 0.0471(4) 0.9721(4) 0.61525(16) 0.0674(12) Uani 1 1 d . . . H4 H -0.0457 1.0338 0.6177 0.081 Uiso 1 1 calc R . . C5 C 0.1408(4) 0.9419(4) 0.65186(13) 0.0563(9) Uani 1 1 d . . . H5 H 0.1130 0.9834 0.6793 0.068 Uiso 1 1 calc R . . C6 C 0.2782(4) 0.8490(3) 0.64821(10) 0.0399(7) Uani 1 1 d . . . C7 C 0.3896(4) 0.8082(3) 0.68672(9) 0.0424(7) Uani 1 1 d . . . H7 H 0.3449 0.7211 0.7025 0.051 Uiso 1 1 calc R . . N8 N 0.4081(4) 0.9318(3) 0.71723(9) 0.0543(7) Uani 1 1 d D . . H8N H 0.453(4) 0.900(4) 0.7427(9) 0.065 Uiso 1 1 d D . . C9 C 0.5302(4) 1.0276(3) 0.69494(11) 0.0505(8) Uani 1 1 d . . . H9A H 0.5939 1.0838 0.7168 0.061 Uiso 1 1 calc R . . H9B H 0.4748 1.0972 0.6751 0.061 Uiso 1 1 calc R . . C10 C 0.6446(4) 0.9232(3) 0.66846(10) 0.0430(7) Uani 1 1 d . . . H10A H 0.6595 0.9595 0.6382 0.052 Uiso 1 1 calc R . . H10B H 0.7530 0.9159 0.6827 0.052 Uiso 1 1 calc R . . N11 N 0.5584(3) 0.7741(2) 0.66836(7) 0.0326(5) Uani 1 1 d . . . C12 C 0.6483(4) 0.6617(3) 0.69621(9) 0.0445(7) Uani 1 1 d . . . H12A H 0.5733 0.5813 0.7043 0.053 Uiso 1 1 calc R . . H12B H 0.6886 0.7080 0.7234 0.053 Uiso 1 1 calc R . . C13 C 0.7922(4) 0.6011(3) 0.66981(11) 0.0489(8) Uani 1 1 d . . . H13A H 0.8733 0.6794 0.6645 0.059 Uiso 1 1 calc R . . H13B H 0.8463 0.5217 0.6864 0.059 Uiso 1 1 calc R . . N14 N 0.7283(3) 0.5425(2) 0.62624(8) 0.0342(5) Uani 1 1 d . . . C15 C 0.8659(4) 0.5170(4) 0.59346(11) 0.0490(8) Uani 1 1 d . . . H15A H 0.9550 0.5887 0.5979 0.059 Uiso 1 1 calc R . . H15B H 0.8251 0.5263 0.5631 0.059 Uiso 1 1 calc R . . C16 C 0.9279(4) 0.3585(4) 0.60232(12) 0.0570(9) Uani 1 1 d . . . H16A H 0.9404 0.3045 0.5744 0.068 Uiso 1 1 calc R . . H16B H 1.0350 0.3609 0.6174 0.068 Uiso 1 1 calc R . . N17 N 0.8025(3) 0.2862(3) 0.63070(9) 0.0487(7) Uani 1 1 d D . . H17N H 0.836(4) 0.270(4) 0.6593(7) 0.058 Uiso 1 1 d D . . C18 C 0.6623(4) 0.3861(3) 0.63173(9) 0.0356(6) Uani 1 1 d . . . H18 H 0.6034 0.3769 0.6603 0.043 Uiso 1 1 calc R . . C19 C 0.5430(3) 0.3572(3) 0.59320(9) 0.0325(6) Uani 1 1 d . . . C20 C 0.5192(4) 0.2178(3) 0.57487(10) 0.0427(7) Uani 1 1 d . . . H20 H 0.5793 0.1364 0.5854 0.051 Uiso 1 1 calc R . . C21 C 0.4062(4) 0.2002(3) 0.54092(11) 0.0506(8) Uani 1 1 d . . . H21 H 0.3888 0.1066 0.5283 0.061 Uiso 1 1 calc R . . C22 C 0.3194(4) 0.3209(4) 0.52576(11) 0.0551(8) Uani 1 1 d . . . H22 H 0.2422 0.3114 0.5028 0.066 Uiso 1 1 calc R . . C23 C 0.3491(4) 0.4569(3) 0.54531(11) 0.0482(8) Uani 1 1 d . . . H23 H 0.2906 0.5394 0.5348 0.058 Uiso 1 1 calc R . . N24 N 0.4575(3) 0.4768(2) 0.57859(8) 0.0332(5) Uani 1 1 d . . . Br2 Br 0.23826(5) 0.41458(4) 0.700874(14) 0.06428(12) Uani 1 1 d . . . OW O -0.0964(5) 0.1980(4) 0.72637(13) 0.0986(11) Uani 1 1 d D . . H1W H -0.082(7) 0.124(4) 0.7402(17) 0.118 Uiso 1 1 d D . . H2W H -0.028(5) 0.262(5) 0.730(2) 0.118 Uiso 1 1 d 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 Cu 0.03300(16) 0.02646(15) 0.02887(15) -0.00074(14) -0.00116(12) 0.00646(14) Br1 0.05134(17) 0.04301(16) 0.03909(15) 0.00956(15) 0.00927(13) 0.00077(15) N1 0.0316(12) 0.0292(12) 0.0481(14) -0.0025(10) 0.0026(10) 0.0035(9) C2 0.0403(16) 0.0365(15) 0.0618(19) -0.0013(16) -0.0128(14) 0.0017(15) C3 0.0342(17) 0.0412(18) 0.101(3) 0.007(2) -0.0114(18) 0.0065(15) C4 0.0350(18) 0.0421(19) 0.125(4) 0.001(2) 0.015(2) 0.0108(16) C5 0.0417(19) 0.0446(19) 0.083(3) -0.0119(17) 0.0228(19) 0.0067(16) C6 0.0382(15) 0.0272(14) 0.0543(18) -0.0042(13) 0.0170(13) -0.0034(12) C7 0.0572(18) 0.0297(14) 0.0401(15) -0.0034(12) 0.0188(13) -0.0053(14) N8 0.077(2) 0.0446(15) 0.0413(15) -0.0125(13) 0.0139(14) 0.0012(15) C9 0.065(2) 0.0347(15) 0.052(2) -0.0136(14) -0.0053(17) -0.0017(16) C10 0.0525(18) 0.0334(15) 0.0432(16) -0.0002(13) 0.0020(15) -0.0084(15) N11 0.0450(14) 0.0242(10) 0.0284(11) -0.0008(9) 0.0012(10) 0.0002(10) C12 0.0700(19) 0.0325(14) 0.0309(14) 0.0014(12) -0.0117(14) 0.0028(16) C13 0.055(2) 0.0363(16) 0.056(2) -0.0028(15) -0.0199(15) 0.0040(15) N14 0.0361(12) 0.0266(11) 0.0399(13) 0.0014(10) -0.0043(10) 0.0059(10) C15 0.0388(17) 0.0470(17) 0.061(2) 0.0006(15) 0.0052(15) 0.0070(15) C16 0.052(2) 0.055(2) 0.064(2) -0.0069(17) -0.0035(17) 0.0272(16) N17 0.0601(18) 0.0368(14) 0.0492(16) 0.0023(12) -0.0135(13) 0.0185(12) C18 0.0486(16) 0.0241(13) 0.0342(14) 0.0031(11) -0.0032(13) 0.0067(13) C19 0.0396(14) 0.0277(13) 0.0303(13) 0.0028(10) 0.0039(11) 0.0056(12) C20 0.0561(19) 0.0299(14) 0.0423(17) 0.0019(11) 0.0017(14) 0.0027(14) C21 0.058(2) 0.0365(17) 0.057(2) -0.0093(15) -0.0005(16) -0.0030(15) C22 0.057(2) 0.055(2) 0.0540(18) -0.0137(17) -0.0151(15) -0.0032(18) C23 0.0527(19) 0.0403(16) 0.0517(18) -0.0012(14) -0.0159(17) 0.0092(15) N24 0.0371(12) 0.0264(11) 0.0361(13) -0.0004(9) -0.0012(10) 0.0026(10) Br2 0.0650(2) 0.0553(2) 0.0726(3) 0.00979(18) -0.01675(19) -0.00799(18) OW 0.084(2) 0.122(3) 0.090(2) 0.031(2) -0.0179(18) -0.025(2) _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 Cu N1 1.999(2) . ? Cu N11 2.032(2) . ? Cu N14 2.039(2) . ? Cu N24 2.055(2) . ? Cu Br1 2.5434(4) . ? N1 C2 1.342(4) . ? N1 C6 1.347(4) . ? C2 C3 1.378(4) . ? C2 H2 0.9300 . ? C3 C4 1.364(6) . ? C3 H3 0.9300 . ? C4 C5 1.356(5) . ? C4 H4 0.9300 . ? C5 C6 1.386(4) . ? C5 H5 0.9300 . ? C6 C7 1.503(4) . ? C7 N8 1.443(4) . ? C7 N11 1.493(4) . ? C7 H7 0.9800 . ? N8 C9 1.464(4) . ? N8 H8N 0.892(18) . ? C9 C10 1.531(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N11 1.505(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N11 C12 1.493(3) . ? C12 C13 1.500(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N14 1.496(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N14 C15 1.494(4) . ? N14 C18 1.507(3) . ? C15 C16 1.528(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N17 1.467(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N17 C18 1.438(4) . ? N17 H17N 0.908(17) . ? C18 C19 1.521(4) . ? C18 H18 0.9800 . ? C19 N24 1.346(3) . ? C19 C20 1.377(4) . ? C20 C21 1.371(4) . ? C20 H20 0.9300 . ? C21 C22 1.365(5) . ? C21 H21 0.9300 . ? C22 C23 1.373(4) . ? C22 H22 0.9300 . ? C23 N24 1.334(4) . ? C23 H23 0.9300 . ? OW H1W 0.787(19) . ? OW H2W 0.80(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 N1 Cu N11 81.48(10) . . ? N1 Cu N14 163.54(10) . . ? N11 Cu N14 86.31(9) . . ? N1 Cu N24 101.92(9) . . ? N11 Cu N24 142.38(9) . . ? N14 Cu N24 81.19(9) . . ? N1 Cu Br1 92.66(7) . . ? N11 Cu Br1 113.55(6) . . ? N14 Cu Br1 102.37(7) . . ? N24 Cu Br1 103.77(7) . . ? C2 N1 C6 119.7(2) . . ? C2 N1 Cu 125.3(2) . . ? C6 N1 Cu 114.74(19) . . ? N1 C2 C3 121.6(3) . . ? N1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 118.6(3) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? N1 C6 C5 120.0(3) . . ? N1 C6 C7 116.0(2) . . ? C5 C6 C7 124.0(3) . . ? N8 C7 N11 107.3(2) . . ? N8 C7 C6 111.1(3) . . ? N11 C7 C6 107.9(2) . . ? N8 C7 H7 110.2 . . ? N11 C7 H7 110.2 . . ? C6 C7 H7 110.2 . . ? C7 N8 C9 103.3(2) . . ? C7 N8 H8N 110(3) . . ? C9 N8 H8N 108(3) . . ? N8 C9 C10 106.2(2) . . ? N8 C9 H9A 110.5 . . ? C10 C9 H9A 110.5 . . ? N8 C9 H9B 110.5 . . ? C10 C9 H9B 110.5 . . ? H9A C9 H9B 108.7 . . ? N11 C10 C9 105.6(2) . . ? N11 C10 H10A 110.6 . . ? C9 C10 H10A 110.6 . . ? N11 C10 H10B 110.6 . . ? C9 C10 H10B 110.6 . . ? H10A C10 H10B 108.8 . . ? C7 N11 C12 111.8(2) . . ? C7 N11 C10 103.5(2) . . ? C12 N11 C10 112.1(2) . . ? C7 N11 Cu 108.83(16) . . ? C12 N11 Cu 104.31(16) . . ? C10 N11 Cu 116.46(18) . . ? N11 C12 C13 108.8(2) . . ? N11 C12 H12A 109.9 . . ? C13 C12 H12A 109.9 . . ? N11 C12 H12B 109.9 . . ? C13 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? N14 C13 C12 108.8(2) . . ? N14 C13 H13A 109.9 . . ? C12 C13 H13A 109.9 . . ? N14 C13 H13B 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C15 N14 C13 111.9(2) . . ? C15 N14 C18 100.9(2) . . ? C13 N14 C18 110.6(2) . . ? C15 N14 Cu 118.93(19) . . ? C13 N14 Cu 107.26(17) . . ? C18 N14 Cu 106.95(17) . . ? N14 C15 C16 105.6(3) . . ? N14 C15 H15A 110.6 . . ? C16 C15 H15A 110.6 . . ? N14 C15 H15B 110.6 . . ? C16 C15 H15B 110.6 . . ? H15A C15 H15B 108.8 . . ? N17 C16 C15 106.7(2) . . ? N17 C16 H16A 110.4 . . ? C15 C16 H16A 110.4 . . ? N17 C16 H16B 110.4 . . ? C15 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? C18 N17 C16 105.9(2) . . ? C18 N17 H17N 108(2) . . ? C16 N17 H17N 114(2) . . ? N17 C18 N14 107.6(2) . . ? N17 C18 C19 111.7(2) . . ? N14 C18 C19 107.3(2) . . ? N17 C18 H18 110.1 . . ? N14 C18 H18 110.1 . . ? C19 C18 H18 110.1 . . ? N24 C19 C20 121.5(3) . . ? N24 C19 C18 115.5(2) . . ? C20 C19 C18 123.0(2) . . ? C21 C20 C19 119.4(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C22 C21 C20 119.5(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 118.3(3) . . ? C21 C22 H22 120.8 . . ? C23 C22 H22 120.8 . . ? N24 C23 C22 123.4(3) . . ? N24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C23 N24 C19 117.9(2) . . ? C23 N24 Cu 128.50(19) . . ? C19 N24 Cu 113.31(18) . . ? H1W OW H2W 116(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N8 H8N Br2 0.892(18) 3.00(3) 3.752(3) 143(3) 3_656 N17 H17N OW 0.908(17) 2.178(19) 3.079(4) 172(3) 1_655 OW H1W Br2 0.787(19) 2.87(4) 3.534(3) 144(5) 3_546 OW H2W Br2 0.80(2) 2.68(3) 3.399(4) 151(6) . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.604 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.062 # Attachment 'CCDC641983.cif' # data_Zn(bptad)ZnBr4 _database_code_depnum_ccdc_archive 'CCDC 641983' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H24 N6 Zn, Br4 Zn' _chemical_formula_sum 'C18 H24 Br4 N6 Zn2' _chemical_formula_weight 774.81 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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 17.2880(3) _cell_length_b 14.8886(2) _cell_length_c 19.7071(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5072.49(14) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9746 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 28.24 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.029 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2992 _exptl_absorpt_coefficient_mu 8.210 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.148 _exptl_absorpt_correction_T_max 0.306 _exptl_absorpt_process_details 'SADABS 2.03, (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 45593 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 28.29 _reflns_number_total 6288 _reflns_number_gt 5196 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0155P)^2^+3.2262P] 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 6288 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0437 _refine_ls_wR_factor_gt 0.0413 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _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 Zn1 Zn 0.671048(15) 0.349874(16) 0.153418(13) 0.01544(6) Uani 1 1 d . . . N1 N 0.60550(11) 0.45670(12) 0.10066(9) 0.0177(4) Uani 1 1 d . . . C2 C 0.62780(16) 0.50949(16) 0.04968(12) 0.0271(6) Uani 1 1 d . . . H2 H 0.6753 0.4984 0.0292 0.033 Uiso 1 1 calc R . . C3 C 0.58316(18) 0.58020(17) 0.02594(14) 0.0368(7) Uani 1 1 d . . . H3 H 0.6009 0.6162 -0.0093 0.044 Uiso 1 1 calc R . . C4 C 0.51255(18) 0.59637(16) 0.05513(14) 0.0374(8) Uani 1 1 d . . . H4 H 0.4818 0.6436 0.0400 0.045 Uiso 1 1 calc R . . C5 C 0.48745(16) 0.54132(15) 0.10762(13) 0.0283(6) Uani 1 1 d . . . H5 H 0.4394 0.5501 0.1277 0.034 Uiso 1 1 calc R . . C6 C 0.53582(13) 0.47313(14) 0.12914(11) 0.0176(5) Uani 1 1 d . . . C7 C 0.51508(13) 0.41342(14) 0.18547(11) 0.0168(5) Uani 1 1 d . . . H7 H 0.4684 0.4203 0.2084 0.020 Uiso 1 1 calc R . . N8 N 0.56221(10) 0.35248(11) 0.20202(9) 0.0143(4) Uani 1 1 d . . . C9 C 0.54849(14) 0.29163(15) 0.25888(12) 0.0199(5) Uani 1 1 d . . . H9A H 0.4989 0.2620 0.2536 0.024 Uiso 1 1 calc R . . H9B H 0.5480 0.3249 0.3012 0.024 Uiso 1 1 calc R . . C10 C 0.61348(14) 0.22218(15) 0.25965(12) 0.0222(5) Uani 1 1 d . . . H10A H 0.6173 0.1956 0.3045 0.027 Uiso 1 1 calc R . . H10B H 0.6019 0.1747 0.2275 0.027 Uiso 1 1 calc R . . N11 N 0.68756(11) 0.26471(12) 0.24161(10) 0.0188(4) Uani 1 1 d . . . H11 H 0.7230 0.2214 0.2318 0.023 Uiso 1 1 calc R . . C12 C 0.71880(14) 0.32484(15) 0.29488(12) 0.0225(5) Uani 1 1 d . . . H12A H 0.7397 0.2893 0.3318 0.027 Uiso 1 1 calc R . . H12B H 0.6777 0.3623 0.3128 0.027 Uiso 1 1 calc R . . C13 C 0.78154(14) 0.38306(15) 0.26494(12) 0.0239(6) Uani 1 1 d . . . H13A H 0.8041 0.4206 0.3000 0.029 Uiso 1 1 calc R . . H13B H 0.8221 0.3457 0.2460 0.029 Uiso 1 1 calc R . . N14 N 0.74725(11) 0.43980(12) 0.21122(9) 0.0189(4) Uani 1 1 d . . . H14 H 0.7185 0.4841 0.2306 0.023 Uiso 1 1 calc R . . C15 C 0.80461(14) 0.48014(15) 0.16441(13) 0.0250(6) Uani 1 1 d . . . H15A H 0.8464 0.5066 0.1905 0.030 Uiso 1 1 calc R . . H15B H 0.7802 0.5275 0.1383 0.030 Uiso 1 1 calc R . . C16 C 0.83724(14) 0.40957(16) 0.11645(13) 0.0268(6) Uani 1 1 d . . . H16A H 0.8605 0.4384 0.0773 0.032 Uiso 1 1 calc R . . H16B H 0.8767 0.3745 0.1394 0.032 Uiso 1 1 calc R . . N17 N 0.77403(11) 0.35134(12) 0.09493(10) 0.0205(4) Uani 1 1 d . . . C18 C 0.77937(14) 0.29644(15) 0.04619(12) 0.0223(5) Uani 1 1 d . . . H18 H 0.8235 0.2943 0.0193 0.027 Uiso 1 1 calc R . . C19 C 0.71368(14) 0.23601(15) 0.03335(11) 0.0193(5) Uani 1 1 d . . . C20 C 0.71441(15) 0.17351(16) -0.01848(12) 0.0240(6) Uani 1 1 d . . . H20 H 0.7568 0.1689 -0.0473 0.029 Uiso 1 1 calc R . . C21 C 0.65092(14) 0.11789(16) -0.02682(12) 0.0247(6) Uani 1 1 d . . . H21 H 0.6499 0.0753 -0.0613 0.030 Uiso 1 1 calc R . . C22 C 0.58941(14) 0.12682(15) 0.01701(12) 0.0236(5) Uani 1 1 d . . . H22 H 0.5458 0.0907 0.0123 0.028 Uiso 1 1 calc R . . C23 C 0.59331(14) 0.19068(15) 0.06854(12) 0.0216(5) Uani 1 1 d . . . H23 H 0.5520 0.1957 0.0985 0.026 Uiso 1 1 calc R . . N24 N 0.65370(11) 0.24471(12) 0.07663(10) 0.0166(4) Uani 1 1 d . . . Zn2 Zn 0.132938(15) 0.621058(16) 0.166049(13) 0.01479(6) Uani 1 1 d . . . Br1 Br 0.100020(13) 0.761054(14) 0.112164(11) 0.01730(5) Uani 1 1 d . . . Br2 Br 0.145149(14) 0.645964(14) 0.287442(11) 0.01782(6) Uani 1 1 d . . . Br3 Br 0.030782(14) 0.513856(15) 0.149391(12) 0.02066(6) Uani 1 1 d . . . Br4 Br 0.255280(14) 0.574192(15) 0.118380(12) 0.02190(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 Zn1 0.01287(14) 0.01649(12) 0.01695(14) -0.00363(10) 0.00076(11) -0.00049(11) N1 0.0209(11) 0.0164(9) 0.0158(10) -0.0003(8) -0.0044(8) -0.0052(8) C2 0.0346(16) 0.0282(13) 0.0185(13) 0.0018(11) -0.0044(12) -0.0139(12) C3 0.053(2) 0.0279(14) 0.0292(16) 0.0111(12) -0.0192(15) -0.0166(14) C4 0.054(2) 0.0179(13) 0.0403(18) 0.0037(12) -0.0283(16) 0.0022(13) C5 0.0307(16) 0.0201(12) 0.0340(16) -0.0064(11) -0.0164(12) 0.0068(11) C6 0.0180(13) 0.0162(11) 0.0187(12) -0.0043(9) -0.0071(10) 0.0008(9) C7 0.0114(12) 0.0194(11) 0.0195(13) -0.0061(9) -0.0013(10) -0.0016(9) N8 0.0144(10) 0.0150(9) 0.0135(10) -0.0020(8) -0.0009(8) -0.0011(8) C9 0.0219(13) 0.0207(11) 0.0172(12) 0.0013(10) 0.0040(10) -0.0046(10) C10 0.0291(15) 0.0160(11) 0.0215(13) 0.0038(10) -0.0043(11) -0.0017(10) N11 0.0168(11) 0.0171(9) 0.0227(11) -0.0030(8) -0.0025(9) 0.0042(8) C12 0.0240(14) 0.0248(12) 0.0187(13) -0.0047(10) -0.0066(11) 0.0025(11) C13 0.0199(13) 0.0225(12) 0.0291(14) -0.0084(11) -0.0090(11) 0.0054(10) N14 0.0190(11) 0.0149(9) 0.0228(11) -0.0057(8) -0.0006(9) 0.0036(8) C15 0.0204(14) 0.0196(12) 0.0349(15) -0.0064(11) 0.0001(12) -0.0059(10) C16 0.0165(13) 0.0278(13) 0.0361(16) -0.0079(12) 0.0048(11) -0.0069(11) N17 0.0149(11) 0.0207(10) 0.0258(11) -0.0036(9) 0.0040(9) -0.0048(8) C18 0.0178(13) 0.0255(12) 0.0236(13) -0.0024(11) 0.0061(10) -0.0019(10) C19 0.0191(13) 0.0216(11) 0.0171(13) -0.0010(10) 0.0043(10) -0.0010(10) C20 0.0237(14) 0.0288(13) 0.0196(13) -0.0053(10) 0.0067(11) -0.0006(11) C21 0.0289(15) 0.0258(12) 0.0195(13) -0.0072(10) 0.0021(11) -0.0036(11) C22 0.0200(14) 0.0245(12) 0.0262(14) -0.0036(10) 0.0005(11) -0.0072(10) C23 0.0204(13) 0.0223(12) 0.0222(13) -0.0038(10) 0.0041(11) -0.0019(10) N24 0.0143(10) 0.0183(9) 0.0174(10) -0.0031(8) 0.0029(8) 0.0009(8) Zn2 0.01438(14) 0.01378(12) 0.01622(14) 0.00169(10) -0.00004(11) 0.00039(10) Br1 0.01747(12) 0.01608(10) 0.01834(12) 0.00473(9) 0.00212(10) 0.00198(9) Br2 0.02081(13) 0.01721(11) 0.01542(12) 0.00292(9) 0.00098(10) -0.00150(9) Br3 0.01832(13) 0.01781(11) 0.02585(14) 0.00151(9) -0.00159(10) -0.00371(9) Br4 0.01579(12) 0.02335(12) 0.02656(13) -0.00259(10) 0.00195(10) 0.00396(10) _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 Zn1 N8 2.1118(18) . ? Zn1 N17 2.1211(19) . ? Zn1 N11 2.1703(19) . ? Zn1 N14 2.1967(18) . ? Zn1 N24 2.1980(18) . ? Zn1 N1 2.2124(19) . ? N1 C2 1.333(3) . ? N1 C6 1.351(3) . ? C2 C3 1.387(4) . ? C2 H2 0.9300 . ? C3 C4 1.371(4) . ? C3 H3 0.9300 . ? C4 C5 1.389(4) . ? C4 H4 0.9300 . ? C5 C6 1.382(3) . ? C5 H5 0.9300 . ? C6 C7 1.467(3) . ? C7 N8 1.262(3) . ? C7 H7 0.9300 . ? N8 C9 1.460(3) . ? C9 C10 1.527(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N11 1.472(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N11 C12 1.482(3) . ? N11 H11 0.9100 . ? C12 C13 1.509(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N14 1.479(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N14 C15 1.482(3) . ? N14 H14 0.9100 . ? C15 C16 1.522(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 N17 1.458(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? N17 C18 1.265(3) . ? C18 C19 1.471(3) . ? C18 H18 0.9300 . ? C19 N24 1.349(3) . ? C19 C20 1.382(3) . ? C20 C21 1.385(3) . ? C20 H20 0.9300 . ? C21 C22 1.376(3) . ? C21 H21 0.9300 . ? C22 C23 1.393(3) . ? C22 H22 0.9300 . ? C23 N24 1.328(3) . ? C23 H23 0.9300 . ? Zn2 Br3 2.4030(3) . ? Zn2 Br1 2.4075(3) . ? Zn2 Br4 2.4172(3) . ? Zn2 Br2 2.4301(3) . ? 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 N8 Zn1 N17 173.83(7) . . ? N8 Zn1 N11 76.39(7) . . ? N17 Zn1 N11 109.32(7) . . ? N8 Zn1 N14 106.74(7) . . ? N17 Zn1 N14 76.83(7) . . ? N11 Zn1 N14 82.07(7) . . ? N8 Zn1 N24 101.76(7) . . ? N17 Zn1 N24 75.39(7) . . ? N11 Zn1 N24 98.81(7) . . ? N14 Zn1 N24 150.80(7) . . ? N8 Zn1 N1 75.14(7) . . ? N17 Zn1 N1 99.62(7) . . ? N11 Zn1 N1 149.74(7) . . ? N14 Zn1 N1 96.47(7) . . ? N24 Zn1 N1 96.81(7) . . ? C2 N1 C6 117.7(2) . . ? C2 N1 Zn1 129.06(18) . . ? C6 N1 Zn1 113.05(14) . . ? N1 C2 C3 122.8(3) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 119.2(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.1(2) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 118.2(3) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? N1 C6 C5 123.0(2) . . ? N1 C6 C7 115.00(19) . . ? C5 C6 C7 122.0(2) . . ? N8 C7 C6 118.3(2) . . ? N8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C7 N8 C9 122.64(19) . . ? C7 N8 Zn1 118.11(15) . . ? C9 N8 Zn1 118.77(14) . . ? N8 C9 C10 107.95(18) . . ? N8 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? N8 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? N11 C10 C9 110.27(17) . . ? N11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? N11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 N11 C12 113.94(18) . . ? C10 N11 Zn1 109.29(13) . . ? C12 N11 Zn1 105.21(13) . . ? C10 N11 H11 109.4 . . ? C12 N11 H11 109.4 . . ? Zn1 N11 H11 109.4 . . ? N11 C12 C13 109.40(19) . . ? N11 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? N11 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? N14 C13 C12 108.67(19) . . ? N14 C13 H13A 110.0 . . ? C12 C13 H13A 110.0 . . ? N14 C13 H13B 110.0 . . ? C12 C13 H13B 110.0 . . ? H13A C13 H13B 108.3 . . ? C13 N14 C15 114.15(19) . . ? C13 N14 Zn1 105.28(13) . . ? C15 N14 Zn1 109.01(13) . . ? C13 N14 H14 109.4 . . ? C15 N14 H14 109.4 . . ? Zn1 N14 H14 109.4 . . ? N14 C15 C16 110.78(18) . . ? N14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? N14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N17 C16 C15 108.27(19) . . ? N17 C16 H16A 110.0 . . ? C15 C16 H16A 110.0 . . ? N17 C16 H16B 110.0 . . ? C15 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? C18 N17 C16 123.4(2) . . ? C18 N17 Zn1 117.86(16) . . ? C16 N17 Zn1 118.50(15) . . ? N17 C18 C19 118.0(2) . . ? N17 C18 H18 121.0 . . ? C19 C18 H18 121.0 . . ? N24 C19 C20 122.6(2) . . ? N24 C19 C18 115.2(2) . . ? C20 C19 C18 122.2(2) . . ? C19 C20 C21 118.9(2) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C22 C21 C20 118.7(2) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C21 C22 C23 119.1(2) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? N24 C23 C22 122.6(2) . . ? N24 C23 H23 118.7 . . ? C22 C23 H23 118.7 . . ? C23 N24 C19 118.06(19) . . ? C23 N24 Zn1 128.43(15) . . ? C19 N24 Zn1 113.51(14) . . ? Br3 Zn2 Br1 109.943(13) . . ? Br3 Zn2 Br4 113.469(13) . . ? Br1 Zn2 Br4 106.579(12) . . ? Br3 Zn2 Br2 107.439(12) . . ? Br1 Zn2 Br2 108.824(12) . . ? Br4 Zn2 Br2 110.526(13) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.927 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.093 # Attachment 'CCDC670334.cif' # data_Mn(bptad)I2 _database_code_depnum_ccdc_archive 'CCDC 670334' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H24 Mn N6, I2' _chemical_formula_sum 'C18 H24 I2 Mn N6' _chemical_formula_weight 633.17 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.2830(8) _cell_length_b 10.7407(7) _cell_length_c 14.2469(8) _cell_angle_alpha 90.00 _cell_angle_beta 98.891(5) _cell_angle_gamma 90.00 _cell_volume 2310.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4335 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.32 _exptl_crystal_description Block _exptl_crystal_colour bronze _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_max 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 3.258 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.635 _exptl_absorpt_correction_T_max 0.670 _exptl_absorpt_process_details 'SADABS 2.03, (Sheldrick, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 SMART CCD area-detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12001 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0222 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2877 _reflns_number_gt 2383 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0293P)^2^+1.5930P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2877 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0634 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn Mn 0.0000 0.34773(5) 0.2500 0.03904(13) Uani 1 2 d S . . N1 N -0.02299(15) 0.5137(2) 0.14481(16) 0.0425(5) Uani 1 1 d . . . C2 C -0.09138(18) 0.5912(3) 0.1311(2) 0.0498(7) Uani 1 1 d . . . H2 H -0.1439 0.5672 0.1514 0.060 Uiso 1 1 calc R . . C3 C -0.0880(2) 0.7069(3) 0.0877(2) 0.0615(8) Uani 1 1 d . . . H3 H -0.1373 0.7587 0.0793 0.074 Uiso 1 1 calc R . . C4 C -0.0116(2) 0.7431(3) 0.0577(2) 0.0644(8) Uani 1 1 d . . . H4 H -0.0075 0.8209 0.0301 0.077 Uiso 1 1 calc R . . C5 C 0.0600(2) 0.6627(3) 0.0688(2) 0.0561(7) Uani 1 1 d . . . H5 H 0.1122 0.6846 0.0471 0.067 Uiso 1 1 calc R . . C6 C 0.05251(18) 0.5495(3) 0.11244(19) 0.0433(6) Uani 1 1 d . . . C7 C 0.12603(19) 0.4606(3) 0.1295(2) 0.0483(7) Uani 1 1 d . . . H7 H 0.1767 0.4721 0.1019 0.058 Uiso 1 1 calc R . . N8 N 0.11905(15) 0.3683(2) 0.18243(17) 0.0477(5) Uani 1 1 d . . . C9 C 0.1870(2) 0.2720(3) 0.2000(3) 0.0632(9) Uani 1 1 d . . . H9A H 0.2452 0.3090 0.2018 0.076 Uiso 1 1 calc R . . H9B H 0.1785 0.2111 0.1492 0.076 Uiso 1 1 calc R . . C10 C 0.1810(2) 0.2103(3) 0.2925(3) 0.0641(8) Uani 1 1 d . . . H10A H 0.2136 0.1326 0.2961 0.077 Uiso 1 1 calc R . . H10B H 0.2083 0.2633 0.3439 0.077 Uiso 1 1 calc R . . N11 N 0.08836(16) 0.1847(2) 0.30499(19) 0.0483(6) Uani 1 1 d . . . H11 H 0.087(2) 0.173(3) 0.364(2) 0.057(10) Uiso 1 1 d . . . C12 C 0.0498(2) 0.0740(3) 0.2520(2) 0.0572(8) Uani 1 1 d . . . H12A H 0.0747 -0.0011 0.2831 0.069 Uiso 1 1 calc R . . H12B H 0.0642 0.0754 0.1880 0.069 Uiso 1 1 calc R . . I I 0.179726(12) 0.025778(18) 0.525001(14) 0.05150(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 Mn 0.0397(3) 0.0335(3) 0.0466(3) 0.000 0.0154(2) 0.000 N1 0.0394(12) 0.0467(11) 0.0423(12) 0.0032(9) 0.0087(9) -0.0082(10) C2 0.0396(14) 0.0572(17) 0.0528(16) 0.0098(13) 0.0080(12) -0.0027(13) C3 0.0540(18) 0.0604(18) 0.069(2) 0.0181(16) 0.0073(15) 0.0068(15) C4 0.072(2) 0.0524(17) 0.068(2) 0.0217(16) 0.0087(17) -0.0068(16) C5 0.0542(18) 0.0544(17) 0.0613(19) 0.0086(14) 0.0143(14) -0.0140(14) C6 0.0410(14) 0.0484(14) 0.0415(14) -0.0014(11) 0.0096(11) -0.0111(11) C7 0.0427(15) 0.0524(16) 0.0538(17) -0.0087(13) 0.0200(13) -0.0098(12) N8 0.0428(12) 0.0422(12) 0.0619(15) -0.0054(11) 0.0204(11) 0.0011(10) C9 0.0474(17) 0.0517(17) 0.096(2) -0.0044(17) 0.0273(17) 0.0086(14) C10 0.0486(17) 0.0574(18) 0.084(2) -0.0017(17) 0.0041(16) 0.0109(15) N11 0.0528(14) 0.0470(13) 0.0447(14) -0.0003(10) 0.0061(11) 0.0068(11) C12 0.0676(19) 0.0396(14) 0.0658(19) -0.0043(13) 0.0142(16) 0.0056(13) I 0.05061(13) 0.04749(12) 0.05724(14) 0.00357(8) 0.01099(9) 0.00506(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn N8 2.197(2) . ? Mn N8 2.197(2) 2 ? Mn N11 2.276(2) 2 ? Mn N11 2.276(2) . ? Mn N1 2.320(2) 2 ? Mn N1 2.320(2) . ? N1 C2 1.327(4) . ? N1 C6 1.363(3) . ? C2 C3 1.393(4) . ? C2 H2 0.9300 . ? C3 C4 1.361(4) . ? C3 H3 0.9300 . ? C4 C5 1.383(5) . ? C4 H4 0.9300 . ? C5 C6 1.378(4) . ? C5 H5 0.9300 . ? C6 C7 1.466(4) . ? C7 N8 1.260(4) . ? C7 H7 0.9300 . ? N8 C9 1.460(4) . ? C9 C10 1.491(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N11 1.479(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N11 C12 1.480(4) . ? N11 H11 0.85(3) . ? C12 C12 1.515(6) 2 ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? 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 N8 Mn N8 168.46(12) . 2 ? N8 Mn N11 114.47(9) . 2 ? N8 Mn N11 74.97(9) 2 2 ? N8 Mn N11 74.97(9) . . ? N8 Mn N11 114.47(9) 2 . ? N11 Mn N11 79.35(13) 2 . ? N8 Mn N1 98.79(8) . 2 ? N8 Mn N1 72.10(8) 2 2 ? N11 Mn N1 146.74(9) 2 2 ? N11 Mn N1 110.26(8) . 2 ? N8 Mn N1 72.10(8) . . ? N8 Mn N1 98.79(8) 2 . ? N11 Mn N1 110.26(8) 2 . ? N11 Mn N1 146.74(9) . . ? N1 Mn N1 79.62(11) 2 . ? C2 N1 C6 117.5(2) . . ? C2 N1 Mn 127.89(18) . . ? C6 N1 Mn 112.58(18) . . ? N1 C2 C3 122.9(3) . . ? N1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 119.2(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 118.9(3) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? N1 C6 C5 122.4(3) . . ? N1 C6 C7 115.3(2) . . ? C5 C6 C7 122.3(3) . . ? N8 C7 C6 118.6(2) . . ? N8 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C7 N8 C9 122.4(2) . . ? C7 N8 Mn 119.59(19) . . ? C9 N8 Mn 118.00(18) . . ? N8 C9 C10 109.0(2) . . ? N8 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? N8 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N11 C10 C9 112.4(3) . . ? N11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? N11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? C10 N11 C12 113.6(2) . . ? C10 N11 Mn 110.07(18) . . ? C12 N11 Mn 105.90(18) . . ? C10 N11 H11 108(2) . . ? C12 N11 H11 109(2) . . ? Mn N11 H11 110(2) . . ? N11 C12 C12 109.7(2) . 2 ? N11 C12 H12A 109.7 . . ? C12 C12 H12A 109.7 2 . ? N11 C12 H12B 109.7 . . ? C12 C12 H12B 109.7 2 . ? H12A C12 H12B 108.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 I 0.85(3) 2.96(3) 3.652(3) 140(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.089 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.075