data_global data_690guillotICMMO _database_code_CSD 792850 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H28 Cl Mn N8 O4, Cl O4' _chemical_formula_sum 'C18 H28 Cl2 Mn N8 O8' _chemical_melting_point ? _exptl_crystal_description cube _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(1) _chemical_formula_weight 610.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1495 0.1591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3385 0.7311 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration . _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 8.5130(4) _cell_length_b 21.2953(9) _cell_length_c 13.6687(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.3070(10) _cell_angle_gamma 90.00 _cell_volume 2457.83(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 9841 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 38.35 _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.330 _exptl_crystal_size_min 0.280 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.759 _exptl_absorpt_correction_T_max 0.795 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _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_% ? _diffrn_reflns_number 45770 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 39.01 _reflns_number_total 13247 _reflns_number_gt 10855 _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 ? _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^)+(0.0447P)^2^+0.6797P] 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 13247 _refine_ls_number_parameters 338 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.20831(10) 0.21057(4) 0.85800(7) 0.01417(14) Uani 1 1 d . . . H1A H -0.2612 0.1965 0.9129 0.017 Uiso 1 1 calc R . . H1B H -0.2881 0.2161 0.8013 0.017 Uiso 1 1 calc R . . C2 C -0.12767(11) 0.27287(4) 0.88394(7) 0.01443(14) Uani 1 1 d . . . H2A H -0.0822 0.2886 0.8272 0.017 Uiso 1 1 calc R . . H2B H -0.2058 0.3030 0.9001 0.017 Uiso 1 1 calc R . . C3 C -0.06466(10) 0.16390(4) 0.73128(6) 0.01317(13) Uani 1 1 d . . . H3A H -0.0621 0.2071 0.7089 0.016 Uiso 1 1 calc R . . H3B H -0.1490 0.1422 0.6903 0.016 Uiso 1 1 calc R . . C4 C 0.09073(10) 0.13268(4) 0.72321(6) 0.01150(13) Uani 1 1 d . . . C5 C 0.32811(11) 0.09649(4) 0.76128(7) 0.01444(14) Uani 1 1 d . . . H5 H 0.4238 0.0852 0.7976 0.017 Uiso 1 1 calc R . . C6 C 0.28997(11) 0.08803(4) 0.66214(7) 0.01492(14) Uani 1 1 d . . . H6 H 0.3533 0.0703 0.6189 0.018 Uiso 1 1 calc R . . C7 C 0.04562(12) 0.11263(5) 0.54142(7) 0.01861(16) Uani 1 1 d . . . H7A H 0.1043 0.0927 0.4945 0.028 Uiso 1 1 calc R . . H7B H 0.0240 0.1554 0.5221 0.028 Uiso 1 1 calc R . . H7C H -0.0524 0.0907 0.5435 0.028 Uiso 1 1 calc R . . C8 C -0.14918(10) 0.09939(4) 0.86102(6) 0.01282(13) Uani 1 1 d . . . H8A H -0.1092 0.0679 0.8192 0.015 Uiso 1 1 calc R . . H8B H -0.2640 0.0980 0.8505 0.015 Uiso 1 1 calc R . . C9 C -0.09115(10) 0.08589(4) 0.96683(6) 0.01116(12) Uani 1 1 d . . . C10 C 0.06336(10) 0.08228(4) 1.10575(6) 0.01257(13) Uani 1 1 d . . . H10 H 0.1481 0.0896 1.1544 0.015 Uiso 1 1 calc R . . C11 C -0.06164(11) 0.04374(4) 1.11469(6) 0.01369(14) Uani 1 1 d . . . H11 H -0.0782 0.0202 1.1698 0.016 Uiso 1 1 calc R . . C12 C -0.31053(11) 0.01415(4) 1.00333(8) 0.01709(15) Uani 1 1 d . . . H12A H -0.3282 0.0045 0.9342 0.026 Uiso 1 1 calc R . . H12B H -0.3942 0.0408 1.0201 0.026 Uiso 1 1 calc R . . H12C H -0.3089 -0.0240 1.0408 0.026 Uiso 1 1 calc R . . C13 C -0.06632(12) 0.25952(5) 1.06262(7) 0.01718(15) Uani 1 1 d . . . H13A H 0.0189 0.2548 1.1153 0.026 Uiso 1 1 calc R . . H13B H -0.1328 0.2230 1.0595 0.026 Uiso 1 1 calc R . . H13C H -0.1276 0.2960 1.0744 0.026 Uiso 1 1 calc R . . C14 C 0.09854(11) 0.32377(4) 0.97284(7) 0.01434(14) Uani 1 1 d . . . H14A H 0.1571 0.3283 1.0381 0.017 Uiso 1 1 calc R . . H14B H 0.0328 0.3607 0.9589 0.017 Uiso 1 1 calc R . . C15 C 0.21037(10) 0.31717(4) 0.89785(6) 0.01154(13) Uani 1 1 d . . . C16 C 0.36834(12) 0.27271(5) 0.80724(7) 0.01703(15) Uani 1 1 d . . . H16 H 0.4236 0.2421 0.7770 0.020 Uiso 1 1 calc R . . C17 C 0.37900(12) 0.33571(5) 0.79300(8) 0.01890(17) Uani 1 1 d . . . H17 H 0.4423 0.3560 0.7522 0.023 Uiso 1 1 calc R . . C18 C 0.24112(12) 0.43065(4) 0.85286(8) 0.01826(16) Uani 1 1 d . . . H18A H 0.1999 0.4406 0.9132 0.027 Uiso 1 1 calc R . . H18B H 0.1637 0.4409 0.7978 0.027 Uiso 1 1 calc R . . H18C H 0.3358 0.4545 0.8488 0.027 Uiso 1 1 calc R . . N1 N -0.09382(9) 0.16217(3) 0.83528(5) 0.01067(11) Uani 1 1 d . . . N2 N -0.00122(9) 0.26686(3) 0.96860(5) 0.01136(11) Uani 1 1 d . . . N3 N 0.20219(9) 0.12448(4) 0.79933(5) 0.01227(12) Uani 1 1 d . . . N4 N 0.04401(9) 0.10881(3) 1.01260(5) 0.01108(11) Uani 1 1 d . . . N5 N 0.26263(9) 0.26143(3) 0.87352(6) 0.01237(12) Uani 1 1 d . . . N6 N 0.13847(9) 0.11117(4) 0.63908(5) 0.01310(12) Uani 1 1 d . . . N7 N -0.15886(9) 0.04650(3) 1.02596(5) 0.01231(12) Uani 1 1 d . . . N8 N 0.27763(9) 0.36359(3) 0.85095(6) 0.01369(12) Uani 1 1 d . . . O1 O 0.43283(11) 0.14302(4) 0.98706(6) 0.02427(16) Uani 1 1 d . . . O2 O 0.30583(9) 0.20408(4) 1.09424(6) 0.02212(14) Uani 1 1 d . . . O3 O 0.50745(13) 0.13360(5) 1.15843(7) 0.0377(2) Uani 1 1 d . . . O4 O 0.57193(10) 0.22523(4) 1.07593(8) 0.03026(19) Uani 1 1 d . . . O5 O 0.38275(9) 0.50831(4) 0.17193(6) 0.02366(15) Uani 1 1 d . . . O6 O 0.17286(11) 0.44290(4) 0.10843(7) 0.03096(19) Uani 1 1 d . . . O7 O 0.13913(10) 0.51266(4) 0.23628(6) 0.02543(16) Uani 1 1 d . . . O8 O 0.15810(11) 0.55130(5) 0.07683(7) 0.0319(2) Uani 1 1 d . . . Cl1 Cl 0.45857(3) 0.176336(10) 1.080477(16) 0.01543(4) Uani 1 1 d . . . Cl2 Cl 0.21260(2) 0.504395(10) 0.148381(15) 0.01300(4) Uani 1 1 d . . . Mn Mn 0.159672(15) 0.178890(6) 0.931970(9) 0.00941(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0104(3) 0.0135(3) 0.0186(4) -0.0018(3) 0.0016(3) 0.0016(3) C2 0.0132(3) 0.0114(3) 0.0187(4) -0.0003(3) 0.0021(3) 0.0022(3) C3 0.0135(3) 0.0139(3) 0.0118(3) 0.0017(3) 0.0006(3) 0.0021(3) C4 0.0135(3) 0.0101(3) 0.0110(3) -0.0002(2) 0.0020(2) 0.0001(2) C5 0.0141(3) 0.0133(3) 0.0161(3) -0.0013(3) 0.0026(3) 0.0019(3) C6 0.0166(4) 0.0122(3) 0.0170(3) -0.0018(3) 0.0061(3) 0.0003(3) C7 0.0217(4) 0.0231(4) 0.0108(3) -0.0011(3) 0.0014(3) -0.0017(3) C8 0.0134(3) 0.0115(3) 0.0130(3) 0.0001(2) -0.0008(3) -0.0035(3) C9 0.0114(3) 0.0093(3) 0.0129(3) -0.0002(2) 0.0022(2) -0.0015(2) C10 0.0151(3) 0.0117(3) 0.0109(3) -0.0001(2) 0.0014(3) 0.0007(3) C11 0.0172(3) 0.0116(3) 0.0129(3) 0.0014(2) 0.0046(3) 0.0009(3) C12 0.0133(3) 0.0130(3) 0.0257(4) 0.0007(3) 0.0053(3) -0.0037(3) C13 0.0174(4) 0.0183(4) 0.0176(4) -0.0020(3) 0.0090(3) -0.0002(3) C14 0.0164(4) 0.0098(3) 0.0180(4) -0.0032(3) 0.0066(3) -0.0019(3) C15 0.0120(3) 0.0090(3) 0.0140(3) 0.0006(2) 0.0030(3) -0.0013(2) C16 0.0179(4) 0.0161(4) 0.0191(4) 0.0043(3) 0.0103(3) 0.0031(3) C17 0.0189(4) 0.0171(4) 0.0227(4) 0.0076(3) 0.0102(3) 0.0005(3) C18 0.0206(4) 0.0101(3) 0.0238(4) 0.0044(3) 0.0018(3) -0.0012(3) N1 0.0115(3) 0.0088(3) 0.0118(3) 0.0001(2) 0.0017(2) 0.0003(2) N2 0.0113(3) 0.0101(3) 0.0134(3) -0.0014(2) 0.0043(2) -0.0011(2) N3 0.0124(3) 0.0117(3) 0.0125(3) -0.0012(2) 0.0012(2) 0.0017(2) N4 0.0117(3) 0.0104(3) 0.0110(3) 0.0001(2) 0.0011(2) -0.0011(2) N5 0.0129(3) 0.0100(3) 0.0152(3) 0.0007(2) 0.0056(2) 0.0005(2) N6 0.0161(3) 0.0122(3) 0.0114(3) -0.0011(2) 0.0030(2) -0.0005(2) N7 0.0124(3) 0.0102(3) 0.0150(3) 0.0007(2) 0.0039(2) -0.0014(2) N8 0.0140(3) 0.0104(3) 0.0169(3) 0.0038(2) 0.0026(2) -0.0010(2) O1 0.0328(4) 0.0178(3) 0.0203(3) -0.0061(3) -0.0040(3) 0.0052(3) O2 0.0143(3) 0.0250(4) 0.0274(4) -0.0024(3) 0.0042(3) -0.0009(3) O3 0.0439(6) 0.0410(5) 0.0252(4) 0.0131(4) -0.0082(4) 0.0084(4) O4 0.0180(3) 0.0280(4) 0.0459(5) -0.0097(4) 0.0084(3) -0.0115(3) O5 0.0130(3) 0.0327(4) 0.0246(4) 0.0015(3) -0.0001(3) -0.0016(3) O6 0.0306(4) 0.0215(4) 0.0395(5) -0.0137(3) -0.0003(4) -0.0025(3) O7 0.0240(4) 0.0356(4) 0.0179(3) 0.0003(3) 0.0075(3) 0.0076(3) O8 0.0300(4) 0.0342(5) 0.0314(4) 0.0207(4) 0.0040(3) 0.0106(4) Cl1 0.01440(8) 0.01471(8) 0.01630(9) -0.00092(6) -0.00145(7) -0.00108(7) Cl2 0.01320(8) 0.01284(8) 0.01263(8) 0.00089(6) 0.00044(6) 0.00156(6) Mn 0.00969(5) 0.00782(5) 0.01085(5) -0.00022(4) 0.00173(4) -0.00064(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.4783(11) . ? C1 C2 1.5150(13) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.4824(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.4743(11) . ? C3 C4 1.4971(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.3275(11) . ? C4 N6 1.3478(11) . ? C5 C6 1.3647(13) . ? C5 N3 1.3844(11) . ? C5 H5 0.9300 . ? C6 N6 1.3791(12) . ? C6 H6 0.9300 . ? C7 N6 1.4626(12) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N1 1.4749(11) . ? C8 C9 1.4955(12) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N4 1.3306(11) . ? C9 N7 1.3444(11) . ? C10 C11 1.3615(12) . ? C10 N4 1.3835(11) . ? C10 H10 0.9300 . ? C11 N7 1.3798(12) . ? C11 H11 0.9300 . ? C12 N7 1.4615(12) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.4711(11) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N2 1.4768(11) . ? C14 C15 1.4917(12) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N5 1.3247(11) . ? C15 N8 1.3451(11) . ? C16 C17 1.3603(13) . ? C16 N5 1.3768(11) . ? C16 H16 0.9300 . ? C17 N8 1.3779(12) . ? C17 H17 0.9300 . ? C18 N8 1.4624(12) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 Mn 2.4094(7) . ? N2 Mn 2.4104(7) . ? N3 Mn 2.2198(7) . ? N4 Mn 2.1651(7) . ? N5 Mn 2.1621(7) . ? O1 Cl1 1.4527(8) . ? O1 Mn 2.4723(9) . ? O2 Cl1 1.4620(8) . ? O2 Mn 2.4604(8) . ? O3 Cl1 1.4226(9) . ? O4 Cl1 1.4264(8) . ? O5 Cl2 1.4457(8) . ? O6 Cl2 1.4424(9) . ? O7 Cl2 1.4342(8) . ? O8 Cl2 1.4332(8) . ? 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 C1 C2 111.63(7) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? N2 C2 C1 111.68(7) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N1 C3 C4 108.58(7) . . ? N1 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? N1 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? N3 C4 N6 111.16(8) . . ? N3 C4 C3 123.43(7) . . ? N6 C4 C3 125.38(8) . . ? C6 C5 N3 109.40(8) . . ? C6 C5 H5 125.3 . . ? N3 C5 H5 125.3 . . ? C5 C6 N6 106.10(8) . . ? C5 C6 H6 127.0 . . ? N6 C6 H6 127.0 . . ? N6 C7 H7A 109.5 . . ? N6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 109.18(7) . . ? N1 C8 H8A 109.8 . . ? C9 C8 H8A 109.8 . . ? N1 C8 H8B 109.8 . . ? C9 C8 H8B 109.8 . . ? H8A C8 H8B 108.3 . . ? N4 C9 N7 110.94(7) . . ? N4 C9 C8 122.94(7) . . ? N7 C9 C8 125.96(7) . . ? C11 C10 N4 109.01(7) . . ? C11 C10 H10 125.5 . . ? N4 C10 H10 125.5 . . ? C10 C11 N7 106.48(7) . . ? C10 C11 H11 126.8 . . ? N7 C11 H11 126.8 . . ? N7 C12 H12A 109.5 . . ? N7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 C15 108.04(7) . . ? N2 C14 H14A 110.1 . . ? C15 C14 H14A 110.1 . . ? N2 C14 H14B 110.1 . . ? C15 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? N5 C15 N8 111.22(7) . . ? N5 C15 C14 121.40(7) . . ? N8 C15 C14 127.29(8) . . ? C17 C16 N5 109.11(8) . . ? C17 C16 H16 125.4 . . ? N5 C16 H16 125.4 . . ? C16 C17 N8 106.53(8) . . ? C16 C17 H17 126.7 . . ? N8 C17 H17 126.7 . . ? N8 C18 H18A 109.5 . . ? N8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C3 N1 C8 110.53(7) . . ? C3 N1 C1 112.42(7) . . ? C8 N1 C1 110.04(7) . . ? C3 N1 Mn 106.04(5) . . ? C8 N1 Mn 107.11(5) . . ? C1 N1 Mn 110.50(5) . . ? C13 N2 C14 109.36(7) . . ? C13 N2 C2 111.98(7) . . ? C14 N2 C2 108.46(7) . . ? C13 N2 Mn 112.71(5) . . ? C14 N2 Mn 107.87(5) . . ? C2 N2 Mn 106.29(5) . . ? C4 N3 C5 105.82(7) . . ? C4 N3 Mn 113.39(6) . . ? C5 N3 Mn 138.25(6) . . ? C9 N4 C10 106.12(7) . . ? C9 N4 Mn 115.82(6) . . ? C10 N4 Mn 137.85(6) . . ? C15 N5 C16 106.10(7) . . ? C15 N5 Mn 118.08(6) . . ? C16 N5 Mn 135.61(6) . . ? C4 N6 C6 107.53(7) . . ? C4 N6 C7 125.79(8) . . ? C6 N6 C7 126.68(8) . . ? C9 N7 C11 107.45(7) . . ? C9 N7 C12 126.99(8) . . ? C11 N7 C12 125.52(7) . . ? C15 N8 C17 107.04(7) . . ? C15 N8 C18 127.21(8) . . ? C17 N8 C18 125.53(8) . . ? Cl1 O1 Mn 98.50(4) . . ? Cl1 O2 Mn 98.74(4) . . ? O3 Cl1 O4 111.37(7) . . ? O3 Cl1 O1 110.06(6) . . ? O4 Cl1 O1 110.21(6) . . ? O3 Cl1 O2 110.02(6) . . ? O4 Cl1 O2 109.17(5) . . ? O1 Cl1 O2 105.86(5) . . ? O8 Cl2 O7 110.38(5) . . ? O8 Cl2 O6 109.53(6) . . ? O7 Cl2 O6 108.80(6) . . ? O8 Cl2 O5 109.88(5) . . ? O7 Cl2 O5 109.74(5) . . ? O6 Cl2 O5 108.47(5) . . ? N5 Mn N4 168.67(3) . . ? N5 Mn N3 90.38(3) . . ? N4 Mn N3 100.83(3) . . ? N5 Mn N1 107.12(3) . . ? N4 Mn N1 75.15(3) . . ? N3 Mn N1 72.70(3) . . ? N5 Mn N2 73.30(3) . . ? N4 Mn N2 97.05(3) . . ? N3 Mn N2 136.99(3) . . ? N1 Mn N2 74.68(2) . . ? N5 Mn O2 88.48(3) . . ? N4 Mn O2 84.38(3) . . ? N3 Mn O2 137.21(3) . . ? N1 Mn O2 147.32(2) . . ? N2 Mn O2 83.04(3) . . ? N5 Mn O1 87.36(3) . . ? N4 Mn O1 95.91(3) . . ? N3 Mn O1 80.95(3) . . ? N1 Mn O1 149.72(2) . . ? N2 Mn O1 135.57(3) . . ? O2 Mn O1 56.26(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -57.42(10) . . . . ? N1 C3 C4 N3 -20.01(11) . . . . ? N1 C3 C4 N6 162.18(8) . . . . ? N3 C5 C6 N6 -0.01(10) . . . . ? N1 C8 C9 N4 -30.57(11) . . . . ? N1 C8 C9 N7 154.55(8) . . . . ? N4 C10 C11 N7 0.11(10) . . . . ? N2 C14 C15 N5 -30.85(12) . . . . ? N2 C14 C15 N8 153.04(8) . . . . ? N5 C16 C17 N8 -0.35(12) . . . . ? C4 C3 N1 C8 -77.99(8) . . . . ? C4 C3 N1 C1 158.61(7) . . . . ? C4 C3 N1 Mn 37.76(7) . . . . ? C9 C8 N1 C3 147.58(7) . . . . ? C9 C8 N1 C1 -87.66(8) . . . . ? C9 C8 N1 Mn 32.49(8) . . . . ? C2 C1 N1 C3 -85.75(9) . . . . ? C2 C1 N1 C8 150.58(7) . . . . ? C2 C1 N1 Mn 32.50(8) . . . . ? C15 C14 N2 C13 158.02(8) . . . . ? C15 C14 N2 C2 -79.60(9) . . . . ? C15 C14 N2 Mn 35.12(8) . . . . ? C1 C2 N2 C13 -74.06(9) . . . . ? C1 C2 N2 C14 165.17(7) . . . . ? C1 C2 N2 Mn 49.41(8) . . . . ? N6 C4 N3 C5 0.33(10) . . . . ? C3 C4 N3 C5 -177.75(8) . . . . ? N6 C4 N3 Mn 165.65(6) . . . . ? C3 C4 N3 Mn -12.43(10) . . . . ? C6 C5 N3 C4 -0.19(10) . . . . ? C6 C5 N3 Mn -159.75(7) . . . . ? N7 C9 N4 C10 0.26(9) . . . . ? C8 C9 N4 C10 -175.30(8) . . . . ? N7 C9 N4 Mn -175.33(5) . . . . ? C8 C9 N4 Mn 9.11(10) . . . . ? C11 C10 N4 C9 -0.23(10) . . . . ? C11 C10 N4 Mn 173.85(7) . . . . ? N8 C15 N5 C16 -0.28(10) . . . . ? C14 C15 N5 C16 -176.96(9) . . . . ? N8 C15 N5 Mn -175.92(6) . . . . ? C14 C15 N5 Mn 7.40(11) . . . . ? C17 C16 N5 C15 0.39(11) . . . . ? C17 C16 N5 Mn 174.88(7) . . . . ? N3 C4 N6 C6 -0.34(10) . . . . ? C3 C4 N6 C6 177.70(8) . . . . ? N3 C4 N6 C7 179.92(8) . . . . ? C3 C4 N6 C7 -2.05(14) . . . . ? C5 C6 N6 C4 0.20(10) . . . . ? C5 C6 N6 C7 179.94(9) . . . . ? N4 C9 N7 C11 -0.19(10) . . . . ? C8 C9 N7 C11 175.20(8) . . . . ? N4 C9 N7 C12 177.48(8) . . . . ? C8 C9 N7 C12 -7.12(14) . . . . ? C10 C11 N7 C9 0.04(9) . . . . ? C10 C11 N7 C12 -177.68(8) . . . . ? N5 C15 N8 C17 0.07(11) . . . . ? C14 C15 N8 C17 176.51(9) . . . . ? N5 C15 N8 C18 174.88(8) . . . . ? C14 C15 N8 C18 -8.68(15) . . . . ? C16 C17 N8 C15 0.17(11) . . . . ? C16 C17 N8 C18 -174.75(9) . . . . ? Mn O1 Cl1 O3 126.25(6) . . . . ? Mn O1 Cl1 O4 -110.53(5) . . . . ? Mn O1 Cl1 O2 7.39(5) . . . . ? Mn O2 Cl1 O3 -126.31(5) . . . . ? Mn O2 Cl1 O4 111.19(5) . . . . ? Mn O2 Cl1 O1 -7.43(5) . . . . ? C15 N5 Mn N4 -21.88(19) . . . . ? C16 N5 Mn N4 164.11(13) . . . . ? C15 N5 Mn N3 150.05(7) . . . . ? C16 N5 Mn N3 -23.96(9) . . . . ? C15 N5 Mn N1 78.06(7) . . . . ? C16 N5 Mn N1 -95.95(9) . . . . ? C15 N5 Mn N2 10.45(6) . . . . ? C16 N5 Mn N2 -163.55(10) . . . . ? C15 N5 Mn O2 -72.74(7) . . . . ? C16 N5 Mn O2 113.26(9) . . . . ? C15 N5 Mn O1 -129.03(7) . . . . ? C16 N5 Mn O1 56.97(9) . . . . ? C9 N4 Mn N5 111.35(15) . . . . ? C10 N4 Mn N5 -62.32(19) . . . . ? C9 N4 Mn N3 -60.43(6) . . . . ? C10 N4 Mn N3 125.89(9) . . . . ? C9 N4 Mn N1 8.22(6) . . . . ? C10 N4 Mn N1 -165.46(9) . . . . ? C9 N4 Mn N2 80.27(6) . . . . ? C10 N4 Mn N2 -93.40(9) . . . . ? C9 N4 Mn O2 162.52(6) . . . . ? C10 N4 Mn O2 -11.15(9) . . . . ? C9 N4 Mn O1 -142.32(6) . . . . ? C10 N4 Mn O1 44.00(9) . . . . ? C4 N3 Mn N5 -82.73(6) . . . . ? C5 N3 Mn N5 75.80(9) . . . . ? C4 N3 Mn N4 95.66(6) . . . . ? C5 N3 Mn N4 -105.81(9) . . . . ? C4 N3 Mn N1 25.11(6) . . . . ? C5 N3 Mn N1 -176.37(10) . . . . ? C4 N3 Mn N2 -17.19(8) . . . . ? C5 N3 Mn N2 141.34(8) . . . . ? C4 N3 Mn O2 -170.91(5) . . . . ? C5 N3 Mn O2 -12.38(11) . . . . ? C4 N3 Mn O1 -169.99(6) . . . . ? C5 N3 Mn O1 -11.47(9) . . . . ? C3 N1 Mn N5 50.53(6) . . . . ? C8 N1 Mn N5 168.58(5) . . . . ? C1 N1 Mn N5 -71.56(6) . . . . ? C3 N1 Mn N4 -141.02(5) . . . . ? C8 N1 Mn N4 -22.96(5) . . . . ? C1 N1 Mn N4 96.90(6) . . . . ? C3 N1 Mn N3 -34.39(5) . . . . ? C8 N1 Mn N3 83.67(5) . . . . ? C1 N1 Mn N3 -156.47(6) . . . . ? C3 N1 Mn N2 117.19(5) . . . . ? C8 N1 Mn N2 -124.75(5) . . . . ? C1 N1 Mn N2 -4.89(5) . . . . ? C3 N1 Mn O2 165.92(5) . . . . ? C8 N1 Mn O2 -76.02(7) . . . . ? C1 N1 Mn O2 43.84(8) . . . . ? C3 N1 Mn O1 -65.06(8) . . . . ? C8 N1 Mn O1 53.00(8) . . . . ? C1 N1 Mn O1 172.86(6) . . . . ? C13 N2 Mn N5 -146.35(6) . . . . ? C14 N2 Mn N5 -25.52(5) . . . . ? C2 N2 Mn N5 90.63(5) . . . . ? C13 N2 Mn N4 27.57(6) . . . . ? C14 N2 Mn N4 148.40(5) . . . . ? C2 N2 Mn N4 -95.44(5) . . . . ? C13 N2 Mn N3 141.79(6) . . . . ? C14 N2 Mn N3 -97.38(6) . . . . ? C2 N2 Mn N3 18.78(7) . . . . ? C13 N2 Mn N1 100.02(6) . . . . ? C14 N2 Mn N1 -139.15(6) . . . . ? C2 N2 Mn N1 -23.00(5) . . . . ? C13 N2 Mn O2 -55.85(6) . . . . ? C14 N2 Mn O2 64.98(5) . . . . ? C2 N2 Mn O2 -178.87(5) . . . . ? C13 N2 Mn O1 -78.36(7) . . . . ? C14 N2 Mn O1 42.47(7) . . . . ? C2 N2 Mn O1 158.63(5) . . . . ? Cl1 O2 Mn N5 -82.80(4) . . . . ? Cl1 O2 Mn N4 106.01(4) . . . . ? Cl1 O2 Mn N3 6.13(7) . . . . ? Cl1 O2 Mn N1 156.93(4) . . . . ? Cl1 O2 Mn N2 -156.16(4) . . . . ? Cl1 O2 Mn O1 5.04(4) . . . . ? Cl1 O1 Mn N5 84.87(4) . . . . ? Cl1 O1 Mn N4 -84.25(4) . . . . ? Cl1 O1 Mn N3 175.68(5) . . . . ? Cl1 O1 Mn N1 -154.77(4) . . . . ? Cl1 O1 Mn N2 22.12(6) . . . . ? Cl1 O1 Mn O2 -5.07(4) . . . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.769 _refine_diff_density_min -0.751 _refine_diff_density_rms 0.075 data_global # Attachment '769GuillotICMMO.cif' data_769GuillotICMMO _database_code_CSD 792851 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C18 H28 Cl Mn N8), (F6 P), 0.5(C H4 O) ' _chemical_formula_sum 'C18.50 H30 Cl F6 Mn N8 O0.50 P' _chemical_formula_weight 607.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0031 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' F F 0.0176 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1026 0.0946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1495 0.1591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3385 0.7311 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5092(12) _cell_length_b 10.8499(13) _cell_length_c 14.270(3) _cell_angle_alpha 97.998(3) _cell_angle_beta 98.664(3) _cell_angle_gamma 115.391(2) _cell_volume 1280.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 7418 _cell_measurement_theta_min 4.26 _cell_measurement_theta_max 26.12 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.060 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.753 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(1) _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_% ? _diffrn_reflns_number 24974 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 38.82 _reflns_number_total 11793 _reflns_number_gt 9887 _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 ? _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^)+(0.0890P)^2^+0.7313P] 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 11793 _refine_ls_number_parameters 342 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1414 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 C100 C 0.1310(4) 0.1110(4) 0.1334(3) 0.0293(7) Uani 0.50 1 d PD . . H10A H 0.2371 0.1716 0.1283 0.044 Uiso 0.50 1 calc PR . . H10B H 0.1363 0.0512 0.1760 0.044 Uiso 0.50 1 calc PR . . H10C H 0.0837 0.1665 0.1593 0.044 Uiso 0.50 1 calc PR . . O1 O 0.0467(3) 0.0370(3) 0.05009(19) 0.0285(6) Uani 0.50 1 d PD . . H1 H 0.012(6) -0.0508(17) 0.048(3) 0.043 Uiso 0.50 1 d PD . . C1 C 0.53140(15) 0.29354(13) 0.30594(10) 0.0138(2) Uani 1 1 d . . . H1A H 0.4263 0.2477 0.2617 0.017 Uiso 1 1 calc R . . H1B H 0.5192 0.3241 0.3700 0.017 Uiso 1 1 calc R . . C2 C 0.59790(15) 0.18914(13) 0.31022(9) 0.0137(2) Uani 1 1 d . . . H2A H 0.6985 0.2322 0.3588 0.016 Uiso 1 1 calc R . . H2B H 0.5236 0.1086 0.3299 0.016 Uiso 1 1 calc R . . C3 C 0.77153(14) 0.52263(13) 0.35151(9) 0.0134(2) Uani 1 1 d . . . H3A H 0.8108 0.4767 0.3946 0.016 Uiso 1 1 calc R . . H3B H 0.7371 0.5813 0.3894 0.016 Uiso 1 1 calc R . . C4 C 0.90168(14) 0.61020(13) 0.30635(9) 0.01281(19) Uani 1 1 d . . . C5 C 1.04778(16) 0.67962(14) 0.20335(10) 0.0160(2) Uani 1 1 d . . . H5 H 1.0832 0.6836 0.1460 0.019 Uiso 1 1 calc R . . C6 C 1.12709(16) 0.77491(14) 0.28976(11) 0.0171(2) Uani 1 1 d . . . H6 H 1.2253 0.8545 0.3025 0.021 Uiso 1 1 calc R . . C7 C 1.06958(17) 0.79526(16) 0.45742(11) 0.0200(2) Uani 1 1 d . . . H7A H 0.9927 0.8274 0.4689 0.030 Uiso 1 1 calc R . . H7B H 1.1749 0.8734 0.4756 0.030 Uiso 1 1 calc R . . H7C H 1.0654 0.7281 0.4956 0.030 Uiso 1 1 calc R . . C8 C 0.54209(15) 0.48027(13) 0.22667(9) 0.0137(2) Uani 1 1 d . . . H8A H 0.6105 0.5786 0.2308 0.016 Uiso 1 1 calc R . . H8B H 0.4581 0.4732 0.2599 0.016 Uiso 1 1 calc R . . C9 C 0.47034(14) 0.40384(13) 0.12256(9) 0.01301(19) Uani 1 1 d . . . C10 C 0.43924(16) 0.28379(14) -0.01998(10) 0.0168(2) Uani 1 1 d . . . H10 H 0.4542 0.2305 -0.0708 0.020 Uiso 1 1 calc R . . C11 C 0.32113(16) 0.32436(15) -0.02641(10) 0.0178(2) Uani 1 1 d . . . H11 H 0.2421 0.3044 -0.0815 0.021 Uiso 1 1 calc R . . C12 C 0.24402(16) 0.46656(17) 0.09186(12) 0.0203(3) Uani 1 1 d . . . H12A H 0.2996 0.5346 0.1524 0.031 Uiso 1 1 calc R . . H12B H 0.1441 0.3964 0.0989 0.031 Uiso 1 1 calc R . . H12C H 0.2239 0.5120 0.0421 0.031 Uiso 1 1 calc R . . C13 C 0.47254(16) 0.03479(14) 0.14878(11) 0.0180(2) Uani 1 1 d . . . H13A H 0.4909 0.0110 0.0860 0.027 Uiso 1 1 calc R . . H13B H 0.3963 0.0709 0.1425 0.027 Uiso 1 1 calc R . . H13C H 0.4315 -0.0473 0.1748 0.027 Uiso 1 1 calc R . . C14 C 0.73664(15) 0.08150(13) 0.22762(10) 0.0149(2) Uani 1 1 d . . . H14A H 0.7356 0.0327 0.1650 0.018 Uiso 1 1 calc R . . H14B H 0.7048 0.0149 0.2687 0.018 Uiso 1 1 calc R . . C15 C 0.90100(14) 0.19768(13) 0.27376(9) 0.01313(19) Uani 1 1 d . . . C16 C 1.10035(15) 0.40549(15) 0.32085(10) 0.0166(2) Uani 1 1 d . . . H16 H 1.1617 0.5019 0.3309 0.020 Uiso 1 1 calc R . . C17 C 1.15264(15) 0.31661(16) 0.35368(11) 0.0192(2) Uani 1 1 d . . . H17 H 1.2545 0.3404 0.3894 0.023 Uiso 1 1 calc R . . C18 C 1.02410(19) 0.05260(18) 0.33465(14) 0.0254(3) Uani 1 1 d . . . H18A H 0.9226 -0.0100 0.3448 0.038 Uiso 1 1 calc R . . H18B H 1.1077 0.0708 0.3897 0.038 Uiso 1 1 calc R . . H18C H 1.0423 0.0105 0.2770 0.038 Uiso 1 1 calc R . . N1 N 0.63667(12) 0.41745(11) 0.27289(8) 0.01189(17) Uani 1 1 d . . . N2 N 0.62435(12) 0.14189(11) 0.21484(8) 0.01274(17) Uani 1 1 d . . . N3 N 0.90565(13) 0.57555(12) 0.21431(8) 0.01371(18) Uani 1 1 d . . . N4 N 0.53275(13) 0.33444(12) 0.07379(8) 0.01417(18) Uani 1 1 d . . . N5 N 0.94185(13) 0.32968(12) 0.27030(9) 0.01504(19) Uani 1 1 d . . . N6 N 1.03274(13) 0.72994(12) 0.35463(9) 0.01454(18) Uani 1 1 d . . . N7 N 0.34222(13) 0.40049(12) 0.06464(9) 0.01483(19) Uani 1 1 d . . . N8 N 1.02361(13) 0.18406(13) 0.32315(9) 0.01603(19) Uani 1 1 d . . . Cl Cl 0.81753(4) 0.24081(4) 0.01950(2) 0.01834(7) Uani 1 1 d . . . Mn Mn 0.75597(2) 0.343915(19) 0.156166(14) 0.01127(5) Uani 1 1 d . . . F1 F 0.44158(14) 0.70597(12) 0.31322(8) 0.0273(2) Uani 1 1 d . . . F2 F 0.52359(13) 0.63507(11) 0.44371(9) 0.0269(2) Uani 1 1 d . . . F3 F 0.70332(13) 0.81323(13) 0.39327(10) 0.0321(2) Uani 1 1 d . . . F4 F 0.55173(16) 0.92683(11) 0.40424(9) 0.0324(2) Uani 1 1 d . . . F5 F 0.63284(12) 0.85675(12) 0.53477(8) 0.0272(2) Uani 1 1 d . . . F6 F 0.37151(11) 0.74692(11) 0.45513(8) 0.02366(19) Uani 1 1 d . . . P P 0.53632(4) 0.78120(4) 0.42379(3) 0.01471(7) 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 C100 0.0194(14) 0.0401(19) 0.0232(14) 0.0088(13) 0.0045(11) 0.0088(13) O1 0.0190(10) 0.0605(18) 0.0243(11) 0.0288(12) 0.0143(8) 0.0261(12) C1 0.0078(4) 0.0146(5) 0.0164(5) 0.0070(4) 0.0040(4) 0.0015(4) C2 0.0100(5) 0.0137(5) 0.0140(5) 0.0059(4) 0.0025(4) 0.0019(4) C3 0.0085(5) 0.0139(5) 0.0122(5) 0.0028(4) 0.0010(3) 0.0005(4) C4 0.0070(4) 0.0116(5) 0.0144(5) 0.0030(4) 0.0006(3) 0.0000(4) C5 0.0098(5) 0.0146(5) 0.0191(6) 0.0064(4) 0.0038(4) 0.0006(4) C6 0.0087(5) 0.0139(5) 0.0220(6) 0.0047(4) 0.0027(4) -0.0009(4) C7 0.0139(5) 0.0177(6) 0.0177(6) -0.0019(4) -0.0022(4) 0.0014(5) C8 0.0089(5) 0.0140(5) 0.0154(5) 0.0043(4) 0.0009(4) 0.0030(4) C9 0.0059(4) 0.0118(5) 0.0157(5) 0.0052(4) 0.0000(3) -0.0008(4) C10 0.0108(5) 0.0160(5) 0.0144(5) 0.0036(4) -0.0017(4) -0.0005(4) C11 0.0093(5) 0.0182(5) 0.0169(5) 0.0057(4) -0.0027(4) -0.0005(4) C12 0.0085(5) 0.0251(6) 0.0267(7) 0.0101(5) 0.0030(4) 0.0062(5) C13 0.0085(5) 0.0148(5) 0.0195(6) 0.0017(4) -0.0022(4) -0.0022(4) C14 0.0095(5) 0.0118(5) 0.0180(5) 0.0032(4) -0.0001(4) 0.0012(4) C15 0.0075(4) 0.0142(5) 0.0142(5) 0.0044(4) 0.0007(3) 0.0020(4) C16 0.0068(5) 0.0173(5) 0.0174(5) 0.0036(4) 0.0000(4) -0.0008(4) C17 0.0059(5) 0.0250(6) 0.0210(6) 0.0085(5) 0.0007(4) 0.0019(4) C18 0.0170(6) 0.0266(7) 0.0370(9) 0.0177(6) 0.0060(6) 0.0111(6) N1 0.0065(4) 0.0117(4) 0.0133(4) 0.0043(3) 0.0010(3) 0.0004(3) N2 0.0061(4) 0.0117(4) 0.0139(4) 0.0026(3) -0.0005(3) -0.0009(3) N3 0.0084(4) 0.0121(4) 0.0151(4) 0.0035(3) 0.0019(3) -0.0001(3) N4 0.0093(4) 0.0141(4) 0.0137(4) 0.0036(3) -0.0006(3) 0.0014(4) N5 0.0074(4) 0.0123(4) 0.0181(5) 0.0021(4) -0.0017(3) -0.0002(3) N6 0.0079(4) 0.0119(4) 0.0164(5) 0.0016(3) -0.0003(3) -0.0006(3) N7 0.0057(4) 0.0148(4) 0.0183(5) 0.0067(4) -0.0005(3) -0.0002(3) N8 0.0079(4) 0.0200(5) 0.0197(5) 0.0097(4) 0.0031(3) 0.0044(4) Cl 0.01113(13) 0.01759(14) 0.01794(14) -0.00038(10) 0.00442(10) 0.00007(11) Mn 0.00625(8) 0.01107(9) 0.01128(8) 0.00276(6) 0.00011(5) -0.00015(6) F1 0.0275(5) 0.0303(5) 0.0191(4) -0.0004(4) 0.0002(4) 0.0122(4) F2 0.0282(5) 0.0203(4) 0.0384(6) 0.0165(4) 0.0142(4) 0.0117(4) F3 0.0159(4) 0.0380(6) 0.0421(7) 0.0176(5) 0.0169(4) 0.0065(4) F4 0.0482(7) 0.0176(4) 0.0337(6) 0.0133(4) 0.0129(5) 0.0138(5) F5 0.0149(4) 0.0292(5) 0.0209(4) 0.0044(4) -0.0022(3) -0.0023(4) F6 0.0102(4) 0.0287(5) 0.0272(5) 0.0029(4) 0.0043(3) 0.0056(3) P 0.00899(13) 0.01285(14) 0.01839(15) 0.00614(11) 0.00308(10) 0.00080(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C100 O1 1.264(5) . ? C100 H10A 0.9600 . ? C100 H10B 0.9600 . ? C100 H10C 0.9600 . ? O1 O1 1.471(6) 2 ? O1 H1 0.859(18) . ? C1 N1 1.4820(16) . ? C1 C2 1.5194(19) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 N2 1.4827(17) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.4699(16) . ? C3 C4 1.5007(17) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N3 1.3258(17) . ? C4 N6 1.3488(16) . ? C5 C6 1.362(2) . ? C5 N3 1.3893(16) . ? C5 H5 0.9300 . ? C6 N6 1.3785(18) . ? C6 H6 0.9300 . ? C7 N6 1.4559(19) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N1 1.4767(17) . ? C8 C9 1.4922(18) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N4 1.3287(18) . ? C9 N7 1.3487(17) . ? C10 C11 1.367(2) . ? C10 N4 1.3788(17) . ? C10 H10 0.9300 . ? C11 N7 1.3754(19) . ? C11 H11 0.9300 . ? C12 N7 1.4638(19) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.4729(16) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N2 1.4756(17) . ? C14 C15 1.4949(17) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 N5 1.3240(17) . ? C15 N8 1.3444(17) . ? C16 C17 1.365(2) . ? C16 N5 1.3830(17) . ? C16 H16 0.9300 . ? C17 N8 1.3838(18) . ? C17 H17 0.9300 . ? C18 N8 1.460(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? N1 Mn 2.3820(11) . ? N2 Mn 2.3550(11) . ? N3 Mn 2.2421(11) . ? N4 Mn 2.2194(11) . ? N5 Mn 2.2885(12) . ? Cl Mn 2.3866(5) . ? F1 P 1.5970(11) . ? F2 P 1.6063(10) . ? F3 P 1.6155(11) . ? F4 P 1.5913(11) . ? F5 P 1.6056(11) . ? F6 P 1.5975(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C100 H10A 109.5 . . ? O1 C100 H10B 109.5 . . ? H10A C100 H10B 109.5 . . ? O1 C100 H10C 109.5 . . ? H10A C100 H10C 109.5 . . ? H10B C100 H10C 109.5 . . ? C100 O1 O1 174.7(4) . 2 ? C100 O1 H1 111(2) . . ? O1 O1 H1 74(2) 2 . ? N1 C1 C2 112.10(10) . . ? N1 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? N2 C2 C1 111.76(10) . . ? N2 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? N2 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N1 C3 C4 108.22(10) . . ? N1 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? N1 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? N3 C4 N6 111.32(11) . . ? N3 C4 C3 123.86(11) . . ? N6 C4 C3 124.75(12) . . ? C6 C5 N3 109.29(12) . . ? C6 C5 H5 125.4 . . ? N3 C5 H5 125.4 . . ? C5 C6 N6 106.33(11) . . ? C5 C6 H6 126.8 . . ? N6 C6 H6 126.8 . . ? N6 C7 H7A 109.5 . . ? N6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? N6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 108.63(10) . . ? N1 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? N1 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.3 . . ? N4 C9 N7 111.22(12) . . ? N4 C9 C8 122.64(11) . . ? N7 C9 C8 126.07(12) . . ? C11 C10 N4 109.18(13) . . ? C11 C10 H10 125.4 . . ? N4 C10 H10 125.4 . . ? C10 C11 N7 106.46(12) . . ? C10 C11 H11 126.8 . . ? N7 C11 H11 126.8 . . ? N7 C12 H12A 109.5 . . ? N7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 C15 108.61(10) . . ? N2 C14 H14A 110.0 . . ? C15 C14 H14A 110.0 . . ? N2 C14 H14B 110.0 . . ? C15 C14 H14B 110.0 . . ? H14A C14 H14B 108.3 . . ? N5 C15 N8 111.73(11) . . ? N5 C15 C14 122.41(11) . . ? N8 C15 C14 125.86(12) . . ? C17 C16 N5 109.33(12) . . ? C17 C16 H16 125.3 . . ? N5 C16 H16 125.3 . . ? C16 C17 N8 106.19(11) . . ? C16 C17 H17 126.9 . . ? N8 C17 H17 126.9 . . ? N8 C18 H18A 109.5 . . ? N8 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N8 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C3 N1 C8 110.85(10) . . ? C3 N1 C1 112.87(10) . . ? C8 N1 C1 110.23(10) . . ? C3 N1 Mn 105.26(7) . . ? C8 N1 Mn 108.79(8) . . ? C1 N1 Mn 108.63(8) . . ? C13 N2 C14 108.53(10) . . ? C13 N2 C2 110.81(10) . . ? C14 N2 C2 110.40(10) . . ? C13 N2 Mn 114.46(8) . . ? C14 N2 Mn 105.63(7) . . ? C2 N2 Mn 106.87(7) . . ? C4 N3 C5 105.68(11) . . ? C4 N3 Mn 109.91(8) . . ? C5 N3 Mn 136.92(9) . . ? C9 N4 C10 105.94(11) . . ? C9 N4 Mn 115.60(8) . . ? C10 N4 Mn 138.26(10) . . ? C15 N5 C16 105.72(11) . . ? C15 N5 Mn 110.93(8) . . ? C16 N5 Mn 140.88(10) . . ? C4 N6 C6 107.37(11) . . ? C4 N6 C7 125.82(12) . . ? C6 N6 C7 126.77(11) . . ? C9 N7 C11 107.21(12) . . ? C9 N7 C12 127.07(12) . . ? C11 N7 C12 125.72(12) . . ? C15 N8 C17 107.03(11) . . ? C15 N8 C18 126.20(12) . . ? C17 N8 C18 126.56(12) . . ? N4 Mn N3 101.17(4) . . ? N4 Mn N5 163.96(4) . . ? N3 Mn N5 83.88(4) . . ? N4 Mn N2 94.97(4) . . ? N3 Mn N2 138.79(4) . . ? N5 Mn N2 71.98(4) . . ? N4 Mn N1 73.17(4) . . ? N3 Mn N1 72.36(4) . . ? N5 Mn N1 94.27(4) . . ? N2 Mn N1 76.60(4) . . ? N4 Mn Cl 96.05(3) . . ? N3 Mn Cl 116.51(3) . . ? N5 Mn Cl 95.20(3) . . ? N2 Mn Cl 98.90(3) . . ? N1 Mn Cl 167.68(3) . . ? F4 P F1 90.17(7) . . ? F4 P F6 91.02(7) . . ? F1 P F6 90.56(6) . . ? F4 P F5 89.95(7) . . ? F1 P F5 179.53(6) . . ? F6 P F5 89.88(6) . . ? F4 P F2 179.15(7) . . ? F1 P F2 90.14(6) . . ? F6 P F2 89.77(6) . . ? F5 P F2 89.73(6) . . ? F4 P F3 90.20(7) . . ? F1 P F3 89.82(7) . . ? F6 P F3 178.72(6) . . ? F5 P F3 89.73(6) . . ? F2 P F3 89.01(6) . . ? 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 C1 C2 N2 -57.00(14) . . . . ? N1 C3 C4 N3 -14.09(17) . . . . ? N1 C3 C4 N6 169.23(12) . . . . ? N3 C5 C6 N6 -0.39(16) . . . . ? N1 C8 C9 N4 -24.20(16) . . . . ? N1 C8 C9 N7 159.16(11) . . . . ? N4 C10 C11 N7 -0.18(15) . . . . ? N2 C14 C15 N5 -21.23(18) . . . . ? N2 C14 C15 N8 158.47(13) . . . . ? N5 C16 C17 N8 -0.32(16) . . . . ? C4 C3 N1 C8 -78.42(13) . . . . ? C4 C3 N1 C1 157.37(10) . . . . ? C4 C3 N1 Mn 39.04(11) . . . . ? C9 C8 N1 C3 149.94(10) . . . . ? C9 C8 N1 C1 -84.36(12) . . . . ? C9 C8 N1 Mn 34.66(11) . . . . ? C2 C1 N1 C3 -81.70(13) . . . . ? C2 C1 N1 C8 153.75(11) . . . . ? C2 C1 N1 Mn 34.64(12) . . . . ? C15 C14 N2 C13 166.33(11) . . . . ? C15 C14 N2 C2 -72.03(13) . . . . ? C15 C14 N2 Mn 43.15(11) . . . . ? C1 C2 N2 C13 -79.00(13) . . . . ? C1 C2 N2 C14 160.72(10) . . . . ? C1 C2 N2 Mn 46.32(11) . . . . ? N6 C4 N3 C5 -0.05(15) . . . . ? C3 C4 N3 C5 -177.12(12) . . . . ? N6 C4 N3 Mn 155.27(9) . . . . ? C3 C4 N3 Mn -21.80(15) . . . . ? C6 C5 N3 C4 0.28(16) . . . . ? C6 C5 N3 Mn -144.63(12) . . . . ? N7 C9 N4 C10 -0.23(14) . . . . ? C8 C9 N4 C10 -177.32(11) . . . . ? N7 C9 N4 Mn 175.51(8) . . . . ? C8 C9 N4 Mn -1.59(15) . . . . ? C11 C10 N4 C9 0.25(15) . . . . ? C11 C10 N4 Mn -173.97(10) . . . . ? N8 C15 N5 C16 -0.18(16) . . . . ? C14 C15 N5 C16 179.55(12) . . . . ? N8 C15 N5 Mn 165.89(9) . . . . ? C14 C15 N5 Mn -14.37(16) . . . . ? C17 C16 N5 C15 0.32(16) . . . . ? C17 C16 N5 Mn -158.82(12) . . . . ? N3 C4 N6 C6 -0.19(16) . . . . ? C3 C4 N6 C6 176.85(12) . . . . ? N3 C4 N6 C7 -177.78(13) . . . . ? C3 C4 N6 C7 -0.7(2) . . . . ? C5 C6 N6 C4 0.35(16) . . . . ? C5 C6 N6 C7 177.91(13) . . . . ? N4 C9 N7 C11 0.12(14) . . . . ? C8 C9 N7 C11 177.09(12) . . . . ? N4 C9 N7 C12 -179.05(12) . . . . ? C8 C9 N7 C12 -2.1(2) . . . . ? C10 C11 N7 C9 0.04(15) . . . . ? C10 C11 N7 C12 179.23(12) . . . . ? N5 C15 N8 C17 -0.01(16) . . . . ? C14 C15 N8 C17 -179.74(13) . . . . ? N5 C15 N8 C18 -175.03(14) . . . . ? C14 C15 N8 C18 5.2(2) . . . . ? C16 C17 N8 C15 0.21(16) . . . . ? C16 C17 N8 C18 175.20(15) . . . . ? C9 N4 Mn N3 -51.27(10) . . . . ? C10 N4 Mn N3 122.57(13) . . . . ? C9 N4 Mn N5 55.8(2) . . . . ? C10 N4 Mn N5 -130.33(17) . . . . ? C9 N4 Mn N2 90.63(9) . . . . ? C10 N4 Mn N2 -95.54(14) . . . . ? C9 N4 Mn N1 16.25(9) . . . . ? C10 N4 Mn N1 -169.91(14) . . . . ? C9 N4 Mn Cl -169.85(9) . . . . ? C10 N4 Mn Cl 3.98(14) . . . . ? C4 N3 Mn N4 100.06(9) . . . . ? C5 N3 Mn N4 -116.00(14) . . . . ? C4 N3 Mn N5 -64.54(9) . . . . ? C5 N3 Mn N5 79.40(14) . . . . ? C4 N3 Mn N2 -11.02(12) . . . . ? C5 N3 Mn N2 132.92(13) . . . . ? C4 N3 Mn N1 31.93(8) . . . . ? C5 N3 Mn N1 175.87(14) . . . . ? C4 N3 Mn Cl -157.31(8) . . . . ? C5 N3 Mn Cl -13.37(15) . . . . ? C15 N5 Mn N4 65.4(2) . . . . ? C16 N5 Mn N4 -136.12(17) . . . . ? C15 N5 Mn N3 174.86(10) . . . . ? C16 N5 Mn N3 -26.68(15) . . . . ? C15 N5 Mn N2 28.71(9) . . . . ? C16 N5 Mn N2 -172.83(16) . . . . ? C15 N5 Mn N1 103.13(9) . . . . ? C16 N5 Mn N1 -98.41(16) . . . . ? C15 N5 Mn Cl -68.98(9) . . . . ? C16 N5 Mn Cl 89.49(15) . . . . ? C13 N2 Mn N4 31.51(10) . . . . ? C14 N2 Mn N4 150.84(8) . . . . ? C2 N2 Mn N4 -91.58(8) . . . . ? C13 N2 Mn N3 144.75(9) . . . . ? C14 N2 Mn N3 -95.92(9) . . . . ? C2 N2 Mn N3 21.66(11) . . . . ? C13 N2 Mn N5 -158.04(10) . . . . ? C14 N2 Mn N5 -38.71(8) . . . . ? C2 N2 Mn N5 78.88(8) . . . . ? C13 N2 Mn N1 102.88(10) . . . . ? C14 N2 Mn N1 -137.79(8) . . . . ? C2 N2 Mn N1 -20.21(7) . . . . ? C13 N2 Mn Cl -65.43(9) . . . . ? C14 N2 Mn Cl 53.90(8) . . . . ? C2 N2 Mn Cl 171.49(7) . . . . ? C3 N1 Mn N4 -146.88(8) . . . . ? C8 N1 Mn N4 -28.03(7) . . . . ? C1 N1 Mn N4 91.98(8) . . . . ? C3 N1 Mn N3 -38.90(8) . . . . ? C8 N1 Mn N3 79.94(8) . . . . ? C1 N1 Mn N3 -160.05(8) . . . . ? C3 N1 Mn N5 43.29(8) . . . . ? C8 N1 Mn N5 162.14(8) . . . . ? C1 N1 Mn N5 -77.85(8) . . . . ? C3 N1 Mn N2 113.62(8) . . . . ? C8 N1 Mn N2 -127.54(8) . . . . ? C1 N1 Mn N2 -7.53(7) . . . . ? C3 N1 Mn Cl -176.58(10) . . . . ? C8 N1 Mn Cl -57.73(17) . . . . ? C1 N1 Mn Cl 62.28(17) . . . . ? _diffrn_measured_fraction_theta_max 0.801 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.369 _refine_diff_density_min -1.153 _refine_diff_density_rms 0.123