Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _publ_contact_author_email miguel.julve@uv.es _publ_contact_author_name 'Prof. M. Julve' _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_address ; Prof. M. Julve Departament de Quimica Inorganica/Instituto de Ciencia Molecular, Facultat de Quimica de la Universitat de Valencia, Dr. Moliner 50, 46100-Burjassot (Valencia) Spain ; _publ_contact_author_phone '34 963864856' _publ_contact_author_fax '34 963864322' _publ_section_title ; 2,2'-Bipyrimidine-and 2,3-bis(2-pyridyl)pyrazine-containing manganese(II) compounds: structural and magnetic properties ; loop_ _publ_author_name _publ_author_address 'Donatella Armentano' ; Dipartimento di Chimica Universita degli Studi della Calabria I-87030 Arcavacata di Rende, Cosenza Italy 'Giovanni De Munno' ; Dipartimento di Chimica Universita degli Studi della Calabria I-87030 Arcavacata di Rende, ; Cosenza ; Italy 'Francesca Guerra' ; Dipartimento di Chimica Universita degli Studi della Calabria I-87030 Arcavacata di Rende, Cosenza Italy ; 'Juan Faus' ; Departament de Quimica Inorganica/Instituto de Ciencia Molecular Facultat de Quimica, Dr. Moliner 50 46100 Burjassot, Valencia Spain ; 'Francesc Lloret' ; Departament de Quimica Inorganica/Instituto de Ciencia Molecular Facultat de Quimica, Dr. Moliner 50 46100 Burjassot, Valencia Spain ; 'Miguel Julve' ; Departament de Quimica Inorganica/Instituto de Ciencia Molecular Facultat de Quimica, Dr. Moliner 50 46100 Burjassot, Valencia Spain ; data_(1) _database_code_CSD 216214 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Cl2 Mn N4 O2' _chemical_formula_weight 320.04 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 monoclinic _symmetry_space_group_name_H-M C2/c 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 17.779(4) _cell_length_b 8.1350(16) _cell_length_c 10.181(2) _cell_angle_alpha 90.00 _cell_angle_beta 123.87(3) _cell_angle_gamma 90.00 _cell_volume 1222.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.739 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 1.511 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7322 _exptl_absorpt_correction_T_max 0.7727 _exptl_absorpt_process_details psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'R3m/V automatic four-circle diffractometer' _diffrn_measurement_method omega/2-theta-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.25 _diffrn_reflns_number 1465 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0130 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 27.06 _reflns_number_total 1352 _reflns_number_gt 1255 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0795P)^2^+1.9315P] 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 1352 _refine_ls_number_parameters 84 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0311 _refine_ls_R_factor_gt 0.0289 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 0.809 _refine_ls_restrained_S_all 0.809 _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 1.0000 0.21368(5) 1.2500 0.03125(16) Uani 1 2 d S . . Cl1 Cl 0.88422(4) 0.40858(7) 1.21269(7) 0.04778(19) Uani 1 1 d . . . N1 N 0.92027(10) 0.1483(2) 0.98474(18) 0.0317(3) Uani 1 1 d . . . N2 N 0.92050(10) -0.01254(19) 0.78948(17) 0.0309(3) Uani 1 1 d . . . C1 C 0.84074(15) 0.2139(3) 0.8713(3) 0.0399(5) Uani 1 1 d . . . H1A H 0.8138 0.2924 0.8989 0.048 Uiso 1 1 calc R . . C2 C 0.79759(14) 0.1680(3) 0.7141(2) 0.0428(5) Uani 1 1 d . . . H2A H 0.7422 0.2133 0.6361 0.051 Uiso 1 1 calc R . . C3 C 0.83993(13) 0.0529(3) 0.6784(2) 0.0375(4) Uani 1 1 d . . . H3A H 0.8120 0.0191 0.5739 0.045 Uiso 1 1 calc R . . C4 C 0.95634(11) 0.0374(2) 0.9380(2) 0.0273(3) Uani 1 1 d . . . O1 O 0.92145(14) 0.7185(2) 1.0486(2) 0.0582(5) Uani 1 1 d D . . H1W H 0.929(2) 0.630(2) 1.116(3) 0.060 Uiso 1 1 d D . . H2W H 0.925(2) 0.659(3) 0.971(3) 0.060 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 Mn1 0.0336(2) 0.0329(2) 0.0297(2) 0.000 0.01920(18) 0.000 Cl1 0.0552(4) 0.0439(3) 0.0565(3) 0.0074(2) 0.0387(3) 0.0134(2) N1 0.0314(7) 0.0356(8) 0.0298(7) 0.0026(6) 0.0180(6) 0.0047(6) N2 0.0294(8) 0.0348(8) 0.0273(7) 0.0004(6) 0.0152(6) -0.0001(6) C1 0.0374(10) 0.0461(12) 0.0378(10) 0.0066(8) 0.0220(9) 0.0130(8) C2 0.0312(9) 0.0572(12) 0.0330(9) 0.0091(9) 0.0136(8) 0.0124(9) C3 0.0318(9) 0.0485(11) 0.0282(8) 0.0022(8) 0.0143(8) 0.0026(8) C4 0.0260(8) 0.0290(8) 0.0284(8) 0.0022(7) 0.0160(7) -0.0006(7) O1 0.0649(12) 0.0575(11) 0.0613(12) -0.0011(8) 0.0408(10) -0.0082(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 Mn1 N1 2.3062(17) . ? Mn1 N1 2.3062(17) 2_757 ? Mn1 N2 2.3388(16) 6_556 ? Mn1 N2 2.3388(16) 5_757 ? Mn1 Cl1 2.4544(7) 2_757 ? Mn1 Cl1 2.4544(7) . ? N1 C4 1.338(2) . ? N1 C1 1.341(3) . ? N2 C4 1.336(2) . ? N2 C3 1.345(2) . ? N2 Mn1 2.3388(16) 5_757 ? C1 C2 1.386(3) . ? C2 C3 1.372(3) . ? C4 C4 1.480(3) 5_757 ? 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 Mn1 N1 153.33(8) . 2_757 ? N1 Mn1 N2 90.23(6) . 6_556 ? N1 Mn1 N2 70.93(6) 2_757 6_556 ? N1 Mn1 N2 70.93(6) . 5_757 ? N1 Mn1 N2 90.23(6) 2_757 5_757 ? N2 Mn1 N2 91.21(8) 6_556 5_757 ? N1 Mn1 Cl1 104.20(5) . 2_757 ? N1 Mn1 Cl1 93.01(5) 2_757 2_757 ? N2 Mn1 Cl1 163.83(4) 6_556 2_757 ? N2 Mn1 Cl1 86.76(4) 5_757 2_757 ? N1 Mn1 Cl1 93.01(5) . . ? N1 Mn1 Cl1 104.20(5) 2_757 . ? N2 Mn1 Cl1 86.76(4) 6_556 . ? N2 Mn1 Cl1 163.83(4) 5_757 . ? Cl1 Mn1 Cl1 99.52(4) 2_757 . ? C4 N1 C1 116.53(16) . . ? C4 N1 Mn1 117.91(12) . . ? C1 N1 Mn1 125.56(14) . . ? C4 N2 C3 116.38(16) . . ? C4 N2 Mn1 117.05(12) . 5_757 ? C3 N2 Mn1 126.50(13) . 5_757 ? N1 C1 C2 121.76(19) . . ? C3 C2 C1 117.27(18) . . ? N2 C3 C2 122.12(18) . . ? N2 C4 N1 125.92(16) . . ? N2 C4 C4 116.9(2) . 5_757 ? N1 C4 C4 117.19(19) . 5_757 ? 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 O1 H1W Cl1 0.953(10) 2.390(15) 3.289(2) 157(3) . O1 H2W Cl1 0.954(10) 2.375(14) 3.268(2) 156(2) 6_565 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.225 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.071 #===END data_2 _database_code_CSD 216215 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Cl4 Mn2 N8 O4' _chemical_formula_weight 792.26 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 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 9.891(2) _cell_length_b 11.031(2) _cell_length_c 15.067(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.61(3) _cell_angle_gamma 90.00 _cell_volume 1640.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description laminar _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.143 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6705 _exptl_absorpt_correction_T_max 0.9141 _exptl_absorpt_process_details psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'R3m/V automatic four-circle diffractometer' _diffrn_measurement_method omega/2-theta-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.2 _diffrn_reflns_number 3083 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.1332 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.05 _reflns_number_total 2905 _reflns_number_gt 1361 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2905 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1277 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1495 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 0.50017(11) 0.50511(11) 0.37378(7) 0.0309(3) Uani 1 1 d . . . Cl1 Cl 0.34650(19) 0.42607(17) 0.48807(12) 0.0376(5) Uani 1 1 d . . . Cl2 Cl 0.3374(3) 0.4549(3) 0.25341(19) 0.0914(10) Uani 1 1 d . . . O1 O 0.4332(5) 0.6885(4) 0.3553(3) 0.0401(13) Uani 1 1 d . . . H1W H 0.3437 0.7132 0.3424 0.060 Uiso 1 1 d . . . H2W H 0.4813 0.7552 0.3801 0.060 Uiso 1 1 d . . . N1 N 0.6363(6) 0.3378(5) 0.3689(4) 0.0314(14) Uani 1 1 d . . . C1 C 0.6310(9) 0.2481(7) 0.4272(5) 0.042(2) Uani 1 1 d . . . H1 H 0.5505 0.2352 0.4545 0.050 Uiso 1 1 calc R . . C2 C 0.7385(9) 0.1738(7) 0.4489(5) 0.045(2) Uani 1 1 d . . . H2 H 0.7295 0.1105 0.4888 0.054 Uiso 1 1 calc R . . C3 C 0.8560(10) 0.1920(8) 0.4130(6) 0.055(3) Uani 1 1 d . . . H3 H 0.9304 0.1432 0.4287 0.066 Uiso 1 1 calc R . . C4 C 0.8662(8) 0.2858(8) 0.3510(5) 0.047(2) Uani 1 1 d . . . H4 H 0.9479 0.3026 0.3263 0.057 Uiso 1 1 calc R . . C5 C 0.7519(7) 0.3523(6) 0.3278(4) 0.0295(17) Uani 1 1 d . . . C6 C 0.7498(7) 0.4504(6) 0.2594(4) 0.0279(17) Uani 1 1 d . . . N2 N 0.6631(6) 0.5412(5) 0.2745(4) 0.0299(15) Uani 1 1 d . . . C7 C 0.6632(8) 0.6369(7) 0.2206(5) 0.043(2) Uani 1 1 d . . . H7 H 0.6044 0.7011 0.2291 0.052 Uiso 1 1 calc R . . C8 C 0.7510(8) 0.6419(8) 0.1514(5) 0.050(2) Uani 1 1 d . . . H8 H 0.7525 0.7116 0.1167 0.060 Uiso 1 1 calc R . . N3 N 0.8320(7) 0.5506(6) 0.1336(4) 0.0450(18) Uani 1 1 d . . . C9 C 0.8277(7) 0.4528(6) 0.1846(5) 0.0323(18) Uani 1 1 d . . . C10 C 0.9083(8) 0.3462(7) 0.1571(5) 0.0365(19) Uani 1 1 d . . . N4 N 0.8453(6) 0.2383(6) 0.1527(4) 0.0381(17) Uani 1 1 d . . . C11 C 0.9130(8) 0.1436(8) 0.1230(5) 0.046(2) Uani 1 1 d . . . H11 H 0.8692 0.0691 0.1187 0.055 Uiso 1 1 calc R . . C12 C 1.0461(8) 0.1506(8) 0.0979(5) 0.047(2) Uani 1 1 d . . . H12 H 1.0890 0.0825 0.0767 0.056 Uiso 1 1 calc R . . C13 C 1.1126(8) 0.2597(8) 0.1050(6) 0.053(3) Uani 1 1 d . . . H13 H 1.2026 0.2671 0.0913 0.064 Uiso 1 1 calc R . . C14 C 1.0393(8) 0.3593(8) 0.1339(5) 0.051(2) Uani 1 1 d . . . H14 H 1.0801 0.4353 0.1374 0.062 Uiso 1 1 calc R . . O2 O 0.4524(5) 0.4183(4) 0.0772(3) 0.0291(12) Uani 1 1 d . . . H4W H 0.5439 0.4325 0.0827 0.060 Uiso 1 1 d . . . H3W H 0.4155 0.4295 0.1309 0.060 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0341(6) 0.0305(6) 0.0287(5) -0.0016(6) 0.0073(4) 0.0034(6) Cl1 0.0333(11) 0.0429(12) 0.0369(10) -0.0008(10) 0.0051(8) -0.0072(10) Cl2 0.105(2) 0.092(2) 0.0757(18) -0.0062(16) -0.0010(16) -0.0074(18) O1 0.034(3) 0.032(3) 0.055(3) 0.002(3) 0.005(3) 0.007(3) N1 0.035(4) 0.027(3) 0.033(3) 0.000(3) 0.006(3) 0.003(3) C1 0.057(6) 0.034(5) 0.036(5) 0.002(4) 0.015(4) 0.003(4) C2 0.064(6) 0.041(5) 0.030(4) 0.006(4) 0.001(4) 0.006(5) C3 0.066(7) 0.050(6) 0.049(6) -0.001(5) 0.001(5) 0.020(5) C4 0.043(5) 0.056(6) 0.042(5) 0.005(4) 0.004(4) 0.014(5) C5 0.031(4) 0.028(4) 0.030(4) -0.002(3) 0.002(3) 0.008(4) C6 0.026(4) 0.025(4) 0.033(4) -0.006(3) 0.004(3) -0.004(3) N2 0.031(4) 0.024(3) 0.035(3) -0.001(3) 0.006(3) 0.001(3) C7 0.060(6) 0.024(4) 0.046(5) 0.008(4) 0.008(4) 0.008(4) C8 0.053(6) 0.043(5) 0.056(5) 0.021(5) 0.019(5) -0.003(5) N3 0.051(4) 0.040(4) 0.046(4) 0.009(4) 0.025(3) 0.003(4) C9 0.037(5) 0.027(4) 0.035(4) -0.004(4) 0.018(4) -0.001(4) C10 0.036(5) 0.040(5) 0.035(4) -0.002(4) 0.011(4) 0.002(4) N4 0.036(4) 0.035(4) 0.045(4) -0.004(3) 0.012(3) -0.001(3) C11 0.041(5) 0.047(5) 0.049(5) -0.008(4) 0.001(4) -0.004(5) C12 0.042(5) 0.047(6) 0.052(5) -0.004(4) 0.002(4) 0.011(5) C13 0.028(5) 0.069(7) 0.063(6) -0.020(5) 0.011(4) 0.003(5) C14 0.043(6) 0.051(6) 0.061(6) -0.009(5) 0.007(5) -0.013(5) O2 0.050(3) 0.023(3) 0.016(2) 0.005(2) 0.016(2) 0.012(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 Mn1 O1 2.141(5) . ? Mn1 N1 2.289(6) . ? Mn1 N2 2.302(6) . ? Mn1 Cl2 2.412(3) . ? Mn1 Cl1 2.523(2) . ? Mn1 Cl1 2.610(2) 3_666 ? Cl1 Mn1 2.610(2) 3_666 ? N1 C1 1.327(9) . ? N1 C5 1.344(8) . ? C1 C2 1.366(10) . ? C2 C3 1.328(10) . ? C3 C4 1.402(11) . ? C4 C5 1.374(9) . ? C5 C6 1.493(9) . ? C6 N2 1.347(8) . ? C6 C9 1.406(9) . ? N2 C7 1.332(8) . ? C7 C8 1.400(10) . ? C8 N3 1.325(9) . ? N3 C9 1.326(8) . ? C9 C10 1.494(10) . ? C10 N4 1.343(9) . ? C10 C14 1.371(10) . ? N4 C11 1.333(9) . ? C11 C12 1.394(10) . ? C12 C13 1.372(11) . ? C13 C14 1.401(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 O1 Mn1 N1 159.3(2) . . ? O1 Mn1 N2 88.60(19) . . ? N1 Mn1 N2 71.4(2) . . ? O1 Mn1 Cl2 86.16(15) . . ? N1 Mn1 Cl2 99.02(16) . . ? N2 Mn1 Cl2 90.73(16) . . ? O1 Mn1 Cl1 102.74(14) . . ? N1 Mn1 Cl1 97.14(16) . . ? N2 Mn1 Cl1 168.52(16) . . ? Cl2 Mn1 Cl1 91.81(9) . . ? O1 Mn1 Cl1 89.32(15) . 3_666 ? N1 Mn1 Cl1 86.95(15) . 3_666 ? N2 Mn1 Cl1 94.14(15) . 3_666 ? Cl2 Mn1 Cl1 173.27(10) . 3_666 ? Cl1 Mn1 Cl1 84.32(7) . 3_666 ? Mn1 Cl1 Mn1 95.68(7) . 3_666 ? C1 N1 C5 117.7(6) . . ? C1 N1 Mn1 122.1(5) . . ? C5 N1 Mn1 116.0(5) . . ? N1 C1 C2 122.8(7) . . ? C3 C2 C1 120.1(8) . . ? C2 C3 C4 118.9(8) . . ? C5 C4 C3 118.1(8) . . ? N1 C5 C4 122.0(7) . . ? N1 C5 C6 115.4(6) . . ? C4 C5 C6 122.5(7) . . ? N2 C6 C9 120.5(6) . . ? N2 C6 C5 113.8(6) . . ? C9 C6 C5 125.6(6) . . ? C7 N2 C6 117.5(6) . . ? C7 N2 Mn1 124.1(5) . . ? C6 N2 Mn1 117.4(4) . . ? N2 C7 C8 120.6(7) . . ? N3 C8 C7 122.2(7) . . ? C8 N3 C9 117.3(6) . . ? N3 C9 C6 121.3(6) . . ? N3 C9 C10 116.2(6) . . ? C6 C9 C10 122.4(7) . . ? N4 C10 C14 121.6(7) . . ? N4 C10 C9 117.2(6) . . ? C14 C10 C9 121.1(8) . . ? C11 N4 C10 118.0(7) . . ? N4 C11 C12 123.4(8) . . ? C13 C12 C11 118.9(8) . . ? C12 C13 C14 117.2(8) . . ? C10 C14 C13 120.8(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C5 C6 N2 27.8(9) . . . . ? N3 C9 C10 N4 -130.8(8) . . . . ? C5 C6 C9 C10 9.6(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 O1 H1W N4 0.93 1.90 2.805(8) 163.2 2_655 O2 H3W Cl2 0.92 2.07 2.981(5) 178.5 . O1 H2W O2 0.94 2.01 2.932(6) 167.3 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.693 _refine_diff_density_min -0.766 _refine_diff_density_rms 0.106 #===END data_3 _database_code_CSD 216216 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 Cl2 Mn N4 O11.50' _chemical_formula_weight 551.16 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 orthorombic _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 20.257(4) _cell_length_b 10.050(2) _cell_length_c 21.792(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4436.6(15) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 0.902 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6871 _exptl_absorpt_correction_T_max 0.9153 _exptl_absorpt_process_details psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'R3m/V automatic four-circle diffractometer' _diffrn_measurement_method omega/2-theta-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2.5 _diffrn_reflns_number 3922 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1736 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.05 _reflns_number_total 3922 _reflns_number_gt 1377 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0350P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3922 _refine_ls_number_parameters 200 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1958 _refine_ls_R_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 0.09502(6) 0.09759(13) 0.33292(6) 0.0450(4) Uani 1 1 d . . . O1 O 0.1293(4) -0.0429(6) 0.3989(3) 0.074(2) Uani 1 1 d D . . H1W H 0.162(3) -0.028(6) 0.430(3) 0.060 Uiso 1 1 d D . . H2W H 0.130(4) -0.1384(12) 0.398(3) 0.060 Uiso 1 1 d D . . O2 O 0.1720(3) 0.2314(7) 0.3599(3) 0.076(2) Uani 1 1 d D . . H3W H 0.206(3) 0.204(6) 0.387(3) 0.060 Uiso 1 1 d D . . H4W H 0.165(3) 0.322(3) 0.373(3) 0.060 Uiso 1 1 d D . . N1 N 0.1511(3) 0.0145(6) 0.2543(3) 0.0473(19) Uiso 1 1 d . . . N2 N 0.0316(3) -0.0691(6) 0.2903(3) 0.0405(19) Uiso 1 1 d . . . N3 N -0.0467(3) -0.2378(7) 0.2229(3) 0.0424(19) Uiso 1 1 d . . . N4 N -0.0165(3) -0.3138(6) 0.1095(3) 0.0447(19) Uiso 1 1 d . . . C1 C 0.2164(4) 0.0408(9) 0.2471(4) 0.060(3) Uiso 1 1 d . . . H1 H 0.2349 0.1142 0.2666 0.072 Uiso 1 1 calc R . . C2 C 0.2555(6) -0.0396(9) 0.2114(4) 0.065(3) Uiso 1 1 d . . . H2 H 0.3003 -0.0213 0.2069 0.078 Uiso 1 1 calc R . . C3 C 0.2283(4) -0.1460(9) 0.1830(4) 0.064(3) Uiso 1 1 d . . . H3 H 0.2549 -0.2019 0.1596 0.077 Uiso 1 1 calc R . . C4 C 0.1616(4) -0.1728(9) 0.1879(4) 0.052(3) Uiso 1 1 d . . . H4 H 0.1429 -0.2457 0.1683 0.062 Uiso 1 1 calc R . . C5 C 0.1241(4) -0.0886(9) 0.2228(3) 0.039(2) Uiso 1 1 d . . . C6 C 0.0521(4) -0.1125(8) 0.2351(3) 0.035(2) Uiso 1 1 d . . . C7 C -0.0266(4) -0.1090(8) 0.3113(4) 0.048(2) Uiso 1 1 d . . . H7 H -0.0430 -0.0731 0.3476 0.058 Uiso 1 1 calc R . . C8 C -0.0634(4) -0.2033(8) 0.2800(4) 0.049(3) Uiso 1 1 d . . . H8 H -0.0997 -0.2426 0.2987 0.059 Uiso 1 1 calc R . . C9 C 0.0093(4) -0.1874(8) 0.1984(4) 0.036(2) Uiso 1 1 d . . . C10 C 0.0165(4) -0.2045(8) 0.1306(4) 0.043(2) Uiso 1 1 d . . . C11 C -0.0158(5) -0.3372(9) 0.0497(4) 0.063(3) Uiso 1 1 d . . . H11 H -0.0386 -0.4110 0.0350 0.075 Uiso 1 1 calc R . . C12 C 0.0177(4) -0.2558(10) 0.0069(5) 0.064(3) Uiso 1 1 d . . . H12 H 0.0189 -0.2760 -0.0347 0.077 Uiso 1 1 calc R . . C13 C 0.0484(5) -0.1448(9) 0.0306(4) 0.067(3) Uiso 1 1 d . . . H13 H 0.0702 -0.0875 0.0039 0.080 Uiso 1 1 calc R . . C14 C 0.0478(4) -0.1154(9) 0.0930(4) 0.057(3) Uiso 1 1 d . . . H14 H 0.0678 -0.0391 0.1084 0.068 Uiso 1 1 calc R . . Cl1 Cl 0.10894(14) -0.3947(3) 0.33757(13) 0.0630(8) Uani 1 1 d . . . O3 O 0.1532(4) -0.2908(7) 0.3367(5) 0.136(4) Uani 1 1 d . . . O4 O 0.0909(6) -0.4209(8) 0.2784(4) 0.153(4) Uani 1 1 d . . . O5 O 0.1343(5) -0.5047(8) 0.3661(5) 0.168(5) Uani 1 1 d . . . O6 O 0.0549(6) -0.3542(11) 0.3691(5) 0.220(7) Uani 1 1 d . . . Cl21 Cl 0.1468(6) 0.2566(13) 0.0572(6) 0.211(5) Uiso 0.50 1 d P . . Cl22 Cl 0.1739(2) 0.1752(5) 0.0509(2) 0.0401(11) Uiso 0.50 1 d P . . O7 O 0.1511(6) 0.1521(12) 0.1019(6) 0.189(5) Uiso 1 1 d . . . O8 O 0.1491(6) 0.1391(11) 0.0023(6) 0.177(4) Uiso 1 1 d . . . O9 O 0.2344(5) 0.2141(10) 0.0483(4) 0.168(4) Uiso 1 1 d . . . O101 O 0.1606(19) 0.532(4) 0.0270(17) 0.324(19) Uiso 0.50 1 d P . . O102 O 0.1963(9) 0.0652(19) 0.0548(8) 0.130(6) Uiso 0.50 1 d P . . O11 O 0.3638(8) 0.032(2) 0.0856(9) 0.165(9) Uani 0.50 1 d P . . O12 O 0.2486(5) 0.0889(9) 0.4442(4) 0.148(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0515(8) 0.0364(8) 0.0470(8) -0.0045(9) -0.0063(8) 0.0043(8) O1 0.108(6) 0.048(4) 0.067(5) -0.002(4) -0.027(4) 0.021(4) O2 0.072(5) 0.060(5) 0.097(6) -0.022(4) -0.032(4) 0.003(4) Cl1 0.088(2) 0.0381(14) 0.0634(18) -0.0023(17) -0.0067(18) 0.0088(17) O3 0.146(8) 0.057(5) 0.204(10) 0.000(7) -0.054(8) -0.021(6) O4 0.264(12) 0.115(7) 0.080(6) -0.005(6) -0.054(7) -0.041(8) O5 0.238(12) 0.043(5) 0.223(11) 0.025(6) -0.124(9) 0.012(6) O6 0.235(12) 0.200(12) 0.226(13) 0.060(9) 0.168(11) 0.107(10) O11 0.088(13) 0.25(3) 0.154(18) 0.050(18) -0.039(13) -0.078(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O1 2.131(6) . ? Mn1 O2 2.141(6) . ? Mn1 N4 2.213(7) 3 ? Mn1 N1 2.219(7) . ? Mn1 N3 2.276(7) 3 ? Mn1 N2 2.306(6) . ? N1 C5 1.357(9) . ? N1 C1 1.359(10) . ? N2 C7 1.328(9) . ? N2 C6 1.344(9) . ? N3 C8 1.335(8) . ? N3 C9 1.351(9) . ? N3 Mn1 2.276(7) 3_545 ? N4 C11 1.325(10) . ? N4 C10 1.366(9) . ? N4 Mn1 2.213(7) 3_545 ? C1 C2 1.373(11) . ? C2 C3 1.354(10) . ? C3 C4 1.381(11) . ? C4 C5 1.367(10) . ? C5 C6 1.503(10) . ? C6 C9 1.399(10) . ? C7 C8 1.385(10) . ? C9 C10 1.495(10) . ? C10 C14 1.370(11) . ? C11 C12 1.413(12) . ? C12 C13 1.377(12) . ? C13 C14 1.393(11) . ? Cl1 O6 1.356(9) . ? Cl1 O4 1.365(7) . ? Cl1 O5 1.369(8) . ? Cl1 O3 1.376(8) . ? Cl21 Cl22 0.994(12) . ? Cl21 O7 1.435(15) . ? Cl21 O8 1.681(15) . ? Cl21 O9 1.834(15) . ? Cl22 O102 1.198(18) . ? Cl22 O7 1.225(13) . ? Cl22 O8 1.226(12) . ? Cl22 O9 1.288(11) . ? O7 O102 1.63(2) . ? O8 O102 1.67(2) . ? O9 O102 1.69(2) . ? O101 O11 1.37(3) 8_665 ? O11 O101 1.37(3) 8_655 ? 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 O2 89.7(3) . . ? O1 Mn1 N4 96.8(3) . 3 ? O2 Mn1 N4 96.6(3) . 3 ? O1 Mn1 N1 96.0(3) . . ? O2 Mn1 N1 94.3(3) . . ? N4 Mn1 N1 163.2(3) 3 . ? O1 Mn1 N3 169.3(3) . 3 ? O2 Mn1 N3 90.2(3) . 3 ? N4 Mn1 N3 72.6(2) 3 3 ? N1 Mn1 N3 94.7(2) . 3 ? O1 Mn1 N2 88.4(2) . . ? O2 Mn1 N2 166.4(3) . . ? N4 Mn1 N2 96.9(2) 3 . ? N1 Mn1 N2 72.6(2) . . ? N3 Mn1 N2 94.2(2) 3 . ? C5 N1 C1 118.9(8) . . ? C5 N1 Mn1 118.1(6) . . ? C1 N1 Mn1 120.9(6) . . ? C7 N2 C6 119.0(7) . . ? C7 N2 Mn1 125.1(6) . . ? C6 N2 Mn1 115.1(5) . . ? C8 N3 C9 118.9(8) . . ? C8 N3 Mn1 125.3(6) . 3_545 ? C9 N3 Mn1 115.0(5) . 3_545 ? C11 N4 C10 118.0(8) . . ? C11 N4 Mn1 119.6(6) . 3_545 ? C10 N4 Mn1 118.9(5) . 3_545 ? N1 C1 C2 120.8(9) . . ? C3 C2 C1 119.3(10) . . ? C2 C3 C4 121.1(10) . . ? C5 C4 C3 117.7(9) . . ? N1 C5 C4 122.0(8) . . ? N1 C5 C6 115.0(7) . . ? C4 C5 C6 122.6(8) . . ? N2 C6 C9 119.6(7) . . ? N2 C6 C5 114.1(7) . . ? C9 C6 C5 125.8(8) . . ? N2 C7 C8 120.9(8) . . ? N3 C8 C7 120.0(8) . . ? N3 C9 C6 119.7(7) . . ? N3 C9 C10 115.4(8) . . ? C6 C9 C10 124.5(8) . . ? N4 C10 C14 123.4(8) . . ? N4 C10 C9 112.3(8) . . ? C14 C10 C9 124.1(8) . . ? N4 C11 C12 123.4(10) . . ? C13 C12 C11 116.0(10) . . ? C12 C13 C14 122.3(10) . . ? C10 C14 C13 116.7(9) . . ? O6 Cl1 O4 108.7(8) . . ? O6 Cl1 O5 108.4(7) . . ? O4 Cl1 O5 112.0(6) . . ? O6 Cl1 O3 107.7(7) . . ? O4 Cl1 O3 107.9(6) . . ? O5 Cl1 O3 112.0(6) . . ? Cl22 Cl21 O7 57.2(8) . . ? Cl22 Cl21 O8 46.3(7) . . ? O7 Cl21 O8 88.1(9) . . ? Cl22 Cl21 O9 42.4(7) . . ? O7 Cl21 O9 80.9(9) . . ? O8 Cl21 O9 74.7(8) . . ? Cl21 Cl22 O102 163.4(13) . . ? Cl21 Cl22 O7 79.9(8) . . ? O102 Cl22 O7 84.4(10) . . ? Cl21 Cl22 O8 97.9(9) . . ? O102 Cl22 O8 86.8(10) . . ? O7 Cl22 O8 124.9(8) . . ? Cl21 Cl22 O9 106.3(9) . . ? O102 Cl22 O9 85.6(10) . . ? O7 Cl22 O9 117.1(8) . . ? O8 Cl22 O9 116.3(8) . . ? Cl22 O7 Cl21 43.0(6) . . ? Cl22 O7 O102 47.1(8) . . ? Cl21 O7 O102 89.9(11) . . ? Cl22 O8 O102 45.9(7) . . ? Cl22 O8 Cl21 35.9(5) . . ? O102 O8 Cl21 80.8(10) . . ? Cl22 O9 O102 45.0(7) . . ? Cl22 O9 Cl21 31.3(5) . . ? O102 O9 Cl21 75.9(9) . . ? Cl22 O102 O7 48.5(8) . . ? Cl22 O102 O8 47.3(8) . . ? O7 O102 O8 82.6(11) . . ? Cl22 O102 O9 49.4(8) . . ? O7 O102 O9 80.5(10) . . ? O8 O102 O9 79.0(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C5 C6 N2 -25.5(10) . . . . ? N3 C9 C10 N4 -27.6(11) . . . . ? C5 C6 C9 C10 -29.0(13) . . . . ? C4 C5 C6 C9 -24.3(13) . . . . ? C6 C9 C10 C11 161.4(8) . . . . ? 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 O1 H1W O12 0.960(10) 2.14(5) 2.928(12) 139(6) . O1 H2W O3 0.961(10) 2.09(5) 2.877(11) 139(6) . O2 H3W O12 0.957(10) 1.90(3) 2.799(11) 156(6) . O2 H4W O5 0.959(10) 1.86(3) 2.764(11) 156(6) 1_565 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.147 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.103 #===END data_4 _database_code_CSD 216217 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H10 Mn N10' _chemical_formula_weight 421.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorombic _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 8.1753(16) _cell_length_b 9.5485(19) _cell_length_c 24.017(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1874.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 0.732 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.548 _exptl_absorpt_correction_T_max 0.515 _exptl_absorpt_process_details psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'R3m/V automatic four-circle diffractometer' _diffrn_measurement_method omega/2-theta-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.9 _diffrn_reflns_number 3140 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.06 _reflns_number_total 2897 _reflns_number_gt 2127 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0410P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 2897 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0791 _refine_ls_wR_factor_gt 0.0716 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 0.79175(7) 0.11674(6) 0.17394(2) 0.04284(17) Uani 1 1 d . . . N1 N 0.7149(4) 0.1458(3) 0.08444(10) 0.0390(7) Uani 1 1 d . . . C1 C 0.6413(5) 0.2630(4) 0.06740(17) 0.0547(11) Uani 1 1 d . . . H1 H 0.6469 0.3416 0.0902 0.066 Uiso 1 1 calc R . . C2 C 0.5576(5) 0.2733(5) 0.01801(17) 0.0581(12) Uani 1 1 d . . . H2 H 0.5093 0.3572 0.0073 0.070 Uiso 1 1 calc R . . C3 C 0.5472(5) 0.1576(5) -0.01480(17) 0.0576(12) Uani 1 1 d . . . H3 H 0.4905 0.1613 -0.0483 0.069 Uiso 1 1 calc R . . C4 C 0.6212(4) 0.0344(4) 0.00178(15) 0.0451(10) Uani 1 1 d . . . H4 H 0.6134 -0.0457 -0.0201 0.054 Uiso 1 1 calc R . . C5 C 0.7070(4) 0.0319(3) 0.05141(13) 0.0347(7) Uani 1 1 d . . . C6 C 0.7860(4) -0.0975(3) 0.07411(12) 0.0353(7) Uani 1 1 d . . . N2 N 0.8108(4) -0.0950(3) 0.12975(10) 0.0397(7) Uani 1 1 d . . . C7 C 0.8642(5) -0.2115(4) 0.15418(15) 0.0516(11) Uani 1 1 d . . . H7 H 0.8856 -0.2112 0.1922 0.062 Uiso 1 1 calc R . . C8 C 0.8880(5) -0.3314(4) 0.12432(17) 0.0553(11) Uani 1 1 d . . . H8 H 0.9165 -0.4130 0.1431 0.066 Uiso 1 1 calc R . . N3 N 0.8718(4) -0.3352(3) 0.06910(12) 0.0482(8) Uani 1 1 d . . . C9 C 0.8277(4) -0.2166(3) 0.04366(14) 0.0362(8) Uani 1 1 d . . . C10 C 0.8368(4) -0.2273(4) -0.01865(14) 0.0384(9) Uani 1 1 d . . . N4 N 0.9162(3) -0.1231(3) -0.04450(12) 0.0449(7) Uani 1 1 d . . . C11 C 0.9304(5) -0.1348(5) -0.09968(16) 0.0565(10) Uani 1 1 d . . . H11 H 0.9851 -0.0637 -0.1185 0.068 Uiso 1 1 calc R . . C12 C 0.8698(5) -0.2449(5) -0.13082(17) 0.0613(12) Uani 1 1 d . . . H12 H 0.8838 -0.2478 -0.1692 0.074 Uiso 1 1 calc R . . C13 C 0.7882(6) -0.3498(4) -0.10339(16) 0.0640(11) Uani 1 1 d . . . H13 H 0.7446 -0.4251 -0.1229 0.077 Uiso 1 1 calc R . . C14 C 0.7721(5) -0.3413(4) -0.04613(16) 0.0499(10) Uani 1 1 d . . . H14 H 0.7184 -0.4115 -0.0265 0.060 Uiso 1 1 calc R . . N5 N 0.8412(5) 0.0268(4) 0.25471(14) 0.0704(11) Uani 1 1 d . . . C15 C 0.8257(5) -0.0487(5) 0.29143(18) 0.0560(11) Uani 1 1 d . . . N6 N 0.8003(5) -0.1259(4) 0.33555(13) 0.0777(10) Uani 1 1 d . . . C16 C 0.8783(5) -0.2436(5) 0.34097(15) 0.0513(11) Uani 1 1 d . . . N7 N 0.9450(4) -0.3470(4) 0.34981(14) 0.0620(10) Uani 1 1 d . . . N8 N 0.7737(5) 0.3358(3) 0.19853(14) 0.0666(10) Uani 1 1 d . . . C17 C 0.7275(5) 0.4345(4) 0.21956(15) 0.0505(10) Uani 1 1 d . . . N9 N 0.6880(5) 0.5554(4) 0.23944(16) 0.0852(13) Uani 1 1 d . . . C18 C 0.5703(5) 0.5685(4) 0.27516(16) 0.0493(10) Uani 1 1 d . . . N10 N 0.4707(4) 0.5919(4) 0.30660(14) 0.0701(11) 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 0.0539(3) 0.0352(3) 0.0394(3) -0.0014(3) 0.0067(3) 0.0018(3) N1 0.0448(17) 0.0296(15) 0.0426(16) 0.0009(12) 0.0041(15) 0.0057(15) C1 0.071(3) 0.034(2) 0.059(3) -0.0024(19) -0.005(2) 0.012(2) C2 0.059(3) 0.050(3) 0.066(3) 0.012(2) -0.001(2) 0.021(2) C3 0.054(3) 0.066(3) 0.053(3) 0.004(2) -0.015(2) 0.015(2) C4 0.041(2) 0.045(2) 0.049(2) -0.0066(18) -0.0072(18) 0.0054(19) C5 0.0332(19) 0.0299(17) 0.0408(19) 0.0038(15) 0.0056(18) -0.0041(18) C6 0.0344(18) 0.0325(19) 0.0389(19) 0.0039(15) 0.0037(17) -0.0016(19) N2 0.0482(19) 0.0289(16) 0.0419(16) 0.0039(12) 0.0089(14) 0.0005(16) C7 0.074(3) 0.037(2) 0.044(2) 0.0087(18) 0.006(2) 0.008(2) C8 0.076(3) 0.039(2) 0.051(3) 0.0136(19) 0.012(2) 0.014(2) N3 0.065(2) 0.0301(17) 0.050(2) 0.0036(14) 0.0073(16) 0.0099(15) C9 0.034(2) 0.0293(18) 0.045(2) 0.0016(16) 0.0042(16) -0.0032(16) C10 0.037(2) 0.035(2) 0.043(2) -0.0031(17) 0.0026(16) 0.0093(17) N4 0.0512(19) 0.0427(18) 0.0408(17) 0.0020(16) 0.0038(14) -0.0042(18) C11 0.063(3) 0.057(3) 0.049(2) 0.004(2) 0.0056(19) -0.005(2) C12 0.075(3) 0.065(3) 0.044(2) -0.009(2) 0.001(2) 0.003(3) C13 0.075(3) 0.058(3) 0.059(3) -0.024(2) -0.009(2) 0.004(3) C14 0.051(2) 0.037(2) 0.061(2) -0.0054(17) -0.002(2) -0.0035(19) N5 0.097(3) 0.070(2) 0.044(2) 0.012(2) -0.002(2) 0.014(2) C15 0.062(3) 0.058(3) 0.048(2) -0.010(2) -0.004(2) 0.016(2) N6 0.102(3) 0.068(2) 0.062(2) 0.014(2) 0.025(2) 0.026(3) C16 0.053(3) 0.061(3) 0.040(2) -0.001(2) 0.0055(18) -0.010(2) N7 0.055(2) 0.055(2) 0.077(2) 0.0141(19) 0.0067(17) -0.0008(19) N8 0.077(3) 0.0438(19) 0.079(2) -0.0125(17) 0.023(2) 0.0015(19) C17 0.054(3) 0.047(2) 0.051(2) -0.0018(19) 0.014(2) -0.005(2) N9 0.095(3) 0.048(2) 0.113(3) -0.020(2) 0.059(3) -0.007(2) C18 0.055(3) 0.040(2) 0.052(3) -0.0078(19) 0.003(2) 0.0030(19) N10 0.063(2) 0.071(3) 0.076(3) -0.010(2) 0.021(2) 0.009(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 Mn1 N5 2.160(3) . ? Mn1 N8 2.179(3) . ? Mn1 N10 2.208(4) 3_645 ? Mn1 N7 2.253(4) 3_755 ? Mn1 N1 2.256(3) . ? Mn1 N2 2.289(3) . ? N1 C1 1.335(4) . ? N1 C5 1.348(4) . ? C1 C2 1.373(5) . ? C2 C3 1.360(5) . ? C3 C4 1.381(5) . ? C4 C5 1.383(4) . ? C5 C6 1.497(4) . ? C6 N2 1.352(4) . ? C6 C9 1.395(4) . ? N2 C7 1.331(4) . ? C7 C8 1.365(5) . ? C8 N3 1.333(4) . ? N3 C9 1.336(4) . ? C9 C10 1.502(5) . ? C10 N4 1.340(4) . ? C10 C14 1.379(5) . ? N4 C11 1.335(4) . ? C11 C12 1.382(5) . ? C12 C13 1.371(5) . ? C13 C14 1.384(5) . ? N5 C15 1.146(5) . ? C15 N6 1.307(5) . ? N6 C16 1.299(6) . ? C16 N7 1.148(5) . ? N7 Mn1 2.253(4) 3_745 ? N8 C17 1.134(4) . ? C17 N9 1.290(5) . ? N9 C18 1.295(5) . ? C18 N10 1.133(5) . ? N10 Mn1 2.208(4) 3_655 ? 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 N5 Mn1 N8 98.70(14) . . ? N5 Mn1 N10 87.07(14) . 3_645 ? N8 Mn1 N10 88.85(14) . 3_645 ? N5 Mn1 N7 96.31(14) . 3_755 ? N8 Mn1 N7 89.18(14) . 3_755 ? N10 Mn1 N7 176.30(14) 3_645 3_755 ? N5 Mn1 N1 163.06(12) . . ? N8 Mn1 N1 96.96(12) . . ? N10 Mn1 N1 86.82(12) 3_645 . ? N7 Mn1 N1 90.32(12) 3_755 . ? N5 Mn1 N2 93.00(12) . . ? N8 Mn1 N2 168.09(11) . . ? N10 Mn1 N2 93.98(12) 3_645 . ? N7 Mn1 N2 87.34(12) 3_755 . ? N1 Mn1 N2 71.69(9) . . ? C1 N1 C5 118.3(3) . . ? C1 N1 Mn1 121.4(2) . . ? C5 N1 Mn1 118.4(2) . . ? N1 C1 C2 123.4(4) . . ? C3 C2 C1 118.3(4) . . ? C2 C3 C4 119.8(4) . . ? C3 C4 C5 119.0(4) . . ? N1 C5 C4 121.2(3) . . ? N1 C5 C6 115.5(3) . . ? C4 C5 C6 123.2(3) . . ? N2 C6 C9 119.7(3) . . ? N2 C6 C5 114.2(3) . . ? C9 C6 C5 126.0(3) . . ? C7 N2 C6 118.0(3) . . ? C7 N2 Mn1 123.8(2) . . ? C6 N2 Mn1 117.6(2) . . ? N2 C7 C8 121.1(3) . . ? N3 C8 C7 122.1(3) . . ? C8 N3 C9 117.3(3) . . ? N3 C9 C6 121.2(3) . . ? N3 C9 C10 112.7(3) . . ? C6 C9 C10 126.1(3) . . ? N4 C10 C14 123.4(3) . . ? N4 C10 C9 115.8(3) . . ? C14 C10 C9 120.7(3) . . ? C11 N4 C10 116.1(3) . . ? N4 C11 C12 124.7(4) . . ? C13 C12 C11 118.0(4) . . ? C12 C13 C14 118.8(4) . . ? C10 C14 C13 119.0(4) . . ? C15 N5 Mn1 157.0(4) . . ? N5 C15 N6 174.8(5) . . ? C16 N6 C15 119.4(4) . . ? N7 C16 N6 175.0(4) . . ? C16 N7 Mn1 122.6(3) . 3_745 ? C17 N8 Mn1 160.3(3) . . ? N8 C17 N9 172.6(4) . . ? C17 N9 C18 121.1(4) . . ? N10 C18 N9 174.1(4) . . ? C18 N10 Mn1 149.4(3) . 3_655 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C5 C6 N2 18.6(4) . . . . ? N3 C9 C10 N4 -130.8(3) . . . . ? C5 C6 C9 C10 14.6(5) . . . . ? C4 C5 C6 C9 20.3(5) . . . . ? C6 C9 C10 C11 49.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.227 _refine_diff_density_min -0.309 _refine_diff_density_rms 0.057 #===END