# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Javier Ruiz' 'M Rosario Diaz' 'Santiago Garcia-granda' 'Roberto Quesada' 'Victor Riera' _publ_contact_author_name 'Dr Javier Ruiz' _publ_contact_author_address ; Quimica Organica e Inorganica Universidad de Oviedo Julian Claveria s/n Oviedo Spain 33071 SPAIN ; _publ_contact_author_email JRUIZ@SAURON.QUIMICA.UNIOVI.ES _publ_requested_journal 'Chemical Communications' _publ_section_title ; P-C versus C-H bond cleavage in coordinated bis(dimethylphosphino)methane: Controlled access to either phosphinite or functionalized diphosphine complexes ; data_2a _database_code_CSD 210714 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H24 Mn N O4 P2, H2 O' _chemical_formula_sum 'C13 H26 Mn N O5 P2' _chemical_formula_weight 393.23 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' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.526(2) _cell_length_b 14.563(10) _cell_length_c 14.59(3) _cell_angle_alpha 108.43(8) _cell_angle_beta 98.34(10) _cell_angle_gamma 98.58(7) _cell_volume 2054(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _exptl_crystal_description Prismatic _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.816 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; XABS2(Parkin, Moezzi and Hope, 1995) ; _exptl_absorpt_correction_T_min 0.675 _exptl_absorpt_correction_T_max 0.847 _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 'Enraf-Nonius CAD4' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 28.02 _diffrn_reflns_number 8009 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 25.97 _reflns_number_total 8009 _reflns_number_gt 4710 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; Nonius CAD-4 Diffractometer Control Software. Data collection with profile analysis over all refelctions (Lehmen and Larsen, 1974; Grant and Gable, 1978) ; _computing_cell_refinement 'CRYSDA (Beurskens et al, 1992)' _computing_data_reduction 'THE REFLEX (local program)' _computing_structure_solution ; Direct Methods using SHELXS97 (Sheldrick,1997) ; _computing_structure_refinement ; Anisotropic least-square carried out with SHELXS-97 (Sheldrick, 1997) Geometric calculations made with PARST (Nardelli, 1983) ; _computing_molecular_graphics ; EUCLID (Speck, 1982) ; _computing_publication_material ; All calculations are made at the University of Oviedo on the Scientific Computer Centre and X-Ray group compututers. ; _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^)+(0.0612P)^2^+1.0546P] 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 8009 _refine_ls_number_parameters 411 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1052 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1344 _refine_ls_wR_factor_gt 0.1103 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Mn1 Mn 0.25368(5) -0.01001(4) 0.73467(4) 0.04378(16) Uani 1 1 d . . . P1 P 0.31050(10) -0.09155(7) 0.58652(7) 0.0498(2) Uani 1 1 d . . . P2 P 0.29165(10) 0.13873(7) 0.70182(7) 0.0499(2) Uani 1 1 d . . . O1 O 0.3891(3) 0.14873(19) 0.6363(2) 0.0657(7) Uani 1 1 d . . . O2 O 0.2275(4) -0.1921(3) 0.7855(3) 0.1092(13) Uani 1 1 d . . . O3 O 0.1595(4) 0.0927(2) 0.9126(2) 0.0861(10) Uani 1 1 d . . . O4 O -0.0199(3) -0.0620(3) 0.6233(3) 0.0959(11) Uani 1 1 d . . . N1 N 0.5454(3) 0.0591(2) 0.8373(2) 0.0593(8) Uani 1 1 d . . . C1 C 0.2376(4) -0.0666(3) 0.4788(3) 0.0666(12) Uani 1 1 d . . . H1A H 0.1442 -0.0759 0.4733 0.100 Uiso 1 1 calc R . . H1B H 0.2571 -0.1111 0.4208 0.100 Uiso 1 1 calc R . . H1C H 0.2728 0.0003 0.4854 0.100 Uiso 1 1 calc R . . C2 C 0.4835(4) -0.0718(4) 0.5846(3) 0.0709(12) Uani 1 1 d . . . H2A H 0.5310 -0.0836 0.6397 0.106 Uiso 1 1 calc R . . H2B H 0.5143 -0.0049 0.5887 0.106 Uiso 1 1 calc R . . H2C H 0.4971 -0.1166 0.5242 0.106 Uiso 1 1 calc R . . C3 C 0.2618(6) -0.2256(3) 0.5465(4) 0.0969(18) Uani 1 1 d . . . H3A H 0.2955 -0.2479 0.5987 0.145 Uiso 1 1 calc R . . H3B H 0.2965 -0.2549 0.4894 0.145 Uiso 1 1 calc R . . H3C H 0.1678 -0.2448 0.5304 0.145 Uiso 1 1 calc R . . C4 C 0.3465(5) 0.2447(3) 0.8162(3) 0.0690(12) Uani 1 1 d . . . H4A H 0.4279 0.2394 0.8515 0.104 Uiso 1 1 calc R . . H4B H 0.2815 0.2459 0.8562 0.104 Uiso 1 1 calc R . . H4C H 0.3591 0.3046 0.8012 0.104 Uiso 1 1 calc R . . C5 C 0.1401(5) 0.1662(4) 0.6495(5) 0.0988(18) Uani 1 1 d . . . H5A H 0.1007 0.1150 0.5873 0.148 Uiso 1 1 calc R . . H5B H 0.1591 0.2286 0.6398 0.148 Uiso 1 1 calc R . . H5C H 0.0806 0.1694 0.6939 0.148 Uiso 1 1 calc R . . C6 C 0.4364(4) 0.0325(3) 0.7982(3) 0.0481(9) Uani 1 1 d . . . C7 C 0.2378(4) -0.1221(3) 0.7642(3) 0.0637(11) Uani 1 1 d . . . C8 C 0.1999(4) 0.0549(3) 0.8451(3) 0.0569(10) Uani 1 1 d . . . C9 C 0.0873(4) -0.0420(3) 0.6665(3) 0.0603(10) Uani 1 1 d . . . C10 C 0.6819(4) 0.0924(3) 0.8902(3) 0.0672(12) Uani 1 1 d . . . C11 C 0.7004(5) 0.1986(4) 0.9547(5) 0.111(2) Uani 1 1 d . . . H11A H 0.6444 0.2036 1.0017 0.167 Uiso 1 1 calc R . . H11B H 0.6784 0.2373 0.9146 0.167 Uiso 1 1 calc R . . H11C H 0.7903 0.2229 0.9891 0.167 Uiso 1 1 calc R . . C12 C 0.7682(5) 0.0840(6) 0.8163(5) 0.131(3) Uani 1 1 d . . . H12A H 0.7560 0.0159 0.7753 0.197 Uiso 1 1 calc R . . H12B H 0.8583 0.1082 0.8501 0.197 Uiso 1 1 calc R . . H12C H 0.7458 0.1224 0.7760 0.197 Uiso 1 1 calc R . . C13 C 0.7047(6) 0.0250(5) 0.9495(5) 0.148(3) Uani 1 1 d . . . H13A H 0.6931 -0.0418 0.9053 0.222 Uiso 1 1 calc R . . H13B H 0.6430 0.0279 0.9922 0.222 Uiso 1 1 calc R . . H13C H 0.7924 0.0463 0.9884 0.222 Uiso 1 1 calc R . . Mn1' Mn 0.18646(5) 0.32471(4) 0.15534(4) 0.04879(17) Uani 1 1 d . . . P1' P 0.28062(12) 0.34663(9) 0.31733(9) 0.0664(3) Uani 1 1 d . . . P2' P 0.30004(14) 0.48160(9) 0.17081(9) 0.0763(4) Uani 1 1 d . . . O1' O 0.3615(4) 0.5517(3) 0.2726(3) 0.1148(14) Uani 1 1 d . . . O2' O 0.0669(3) 0.3031(3) -0.0484(2) 0.0907(11) Uani 1 1 d . . . O3' O 0.4116(3) 0.2412(3) 0.0936(3) 0.1120(14) Uani 1 1 d . . . O4' O 0.0311(3) 0.1275(2) 0.1271(3) 0.0939(11) Uani 1 1 d . . . N1' N -0.0225(4) 0.4345(3) 0.2357(3) 0.0687(10) Uani 1 1 d . . . C1' C 0.4576(6) 0.3702(6) 0.3498(5) 0.134(3) Uani 1 1 d . . . H1D H 0.4893 0.3208 0.3031 0.201 Uiso 1 1 calc R . . H1E H 0.4840 0.3679 0.4147 0.201 Uiso 1 1 calc R . . H1F H 0.4934 0.4345 0.3489 0.201 Uiso 1 1 calc R . . C2' C 0.2495(7) 0.4464(5) 0.4152(4) 0.137(3) Uani 1 1 d . . . H2D H 0.2725 0.5074 0.4033 0.205 Uiso 1 1 calc R . . H2E H 0.3013 0.4510 0.4769 0.205 Uiso 1 1 calc R . . H2F H 0.1581 0.4343 0.4177 0.205 Uiso 1 1 calc R . . C3' C 0.2330(10) 0.2417(6) 0.3540(5) 0.227(6) Uani 1 1 d . . . H3D H 0.2465 0.1831 0.3063 0.340 Uiso 1 1 calc R . . H3E H 0.1419 0.2342 0.3577 0.340 Uiso 1 1 calc R . . H3F H 0.2851 0.2519 0.4174 0.340 Uiso 1 1 calc R . . C4' C 0.4189(8) 0.4750(5) 0.0937(6) 0.175(4) Uani 1 1 d . . . H4D H 0.4850 0.4428 0.1144 0.263 Uiso 1 1 calc R . . H4E H 0.4591 0.5407 0.0992 0.263 Uiso 1 1 calc R . . H4F H 0.3764 0.4382 0.0264 0.263 Uiso 1 1 calc R . . C5' C 0.1906(7) 0.5454(4) 0.1129(5) 0.143(3) Uani 1 1 d . . . H5D H 0.1196 0.5557 0.1470 0.215 Uiso 1 1 calc R . . H5E H 0.1559 0.5055 0.0449 0.215 Uiso 1 1 calc R . . H5F H 0.2395 0.6082 0.1168 0.215 Uiso 1 1 calc R . . C6' C 0.0559(4) 0.3931(3) 0.2064(3) 0.0572(10) Uani 1 1 d . . . C7' C 0.1132(4) 0.3118(3) 0.0293(3) 0.0613(10) Uani 1 1 d . . . C8' C 0.3242(4) 0.2734(3) 0.1173(3) 0.0696(12) Uani 1 1 d . . . C9' C 0.0913(4) 0.2044(3) 0.1398(3) 0.0595(10) Uani 1 1 d . . . C10' C -0.1174(6) 0.4935(4) 0.2729(4) 0.0878(16) Uani 1 1 d . . . C11' C -0.0407(9) 0.5848(6) 0.3565(7) 0.193(4) Uani 1 1 d . . . H11D H 0.0050 0.5656 0.4072 0.290 Uiso 1 1 calc R . . H11E H -0.0998 0.6252 0.3833 0.290 Uiso 1 1 calc R . . H11F H 0.0216 0.6215 0.3324 0.290 Uiso 1 1 calc R . . C12' C -0.1857(10) 0.5174(9) 0.1937(6) 0.239(6) Uani 1 1 d . . . H12D H -0.1236 0.5526 0.1681 0.359 Uiso 1 1 calc R . . H12E H -0.2461 0.5580 0.2178 0.359 Uiso 1 1 calc R . . H12F H -0.2332 0.4575 0.1422 0.359 Uiso 1 1 calc R . . C13' C -0.2031(9) 0.4379(6) 0.3183(8) 0.209(5) Uani 1 1 d . . . H13D H -0.1502 0.4248 0.3702 0.314 Uiso 1 1 calc R . . H13E H -0.2505 0.3764 0.2690 0.314 Uiso 1 1 calc R . . H13F H -0.2642 0.4764 0.3449 0.314 Uiso 1 1 calc R . . O5 O 0.6078(5) 0.6577(4) 0.3928(4) 0.1203(17) Uani 1 1 d . . . H51 H 0.538(6) 0.693(5) 0.421(5) 0.119(17) Uiso 1 1 d . . . H52 H 0.536(6) 0.617(5) 0.356(5) 0.119(17) Uiso 1 1 d . . . O6 O 0.3517(4) 0.7559(3) 0.3057(4) 0.1151(15) Uani 1 1 d . . . H61 H 0.466(8) 0.787(6) 0.339(6) 0.20(2) Uiso 1 1 d . . . H62 H 0.360(8) 0.694(6) 0.322(6) 0.20(2) 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 0.0472(3) 0.0388(3) 0.0430(3) 0.0145(2) 0.0050(2) 0.0054(2) P1 0.0555(6) 0.0431(5) 0.0451(5) 0.0112(4) 0.0063(4) 0.0054(4) P2 0.0526(6) 0.0392(5) 0.0546(6) 0.0178(4) -0.0008(5) 0.0076(4) O1 0.0794(19) 0.0494(16) 0.0642(17) 0.0215(13) 0.0153(15) -0.0035(14) O2 0.181(4) 0.063(2) 0.108(3) 0.051(2) 0.054(3) 0.030(2) O3 0.118(3) 0.075(2) 0.070(2) 0.0161(17) 0.042(2) 0.029(2) O4 0.0508(19) 0.118(3) 0.103(3) 0.040(2) -0.0080(18) -0.0108(18) N1 0.054(2) 0.058(2) 0.061(2) 0.0220(17) -0.0056(17) 0.0091(16) C1 0.059(3) 0.088(3) 0.045(2) 0.018(2) 0.0010(19) 0.015(2) C2 0.059(3) 0.095(3) 0.060(3) 0.022(2) 0.013(2) 0.027(2) C3 0.154(5) 0.040(2) 0.085(3) 0.006(2) 0.040(3) 0.003(3) C4 0.086(3) 0.039(2) 0.071(3) 0.009(2) 0.010(2) 0.007(2) C5 0.079(3) 0.073(3) 0.146(5) 0.052(3) -0.015(3) 0.023(3) C6 0.059(2) 0.043(2) 0.042(2) 0.0165(16) 0.0033(18) 0.0136(18) C7 0.088(3) 0.050(2) 0.061(3) 0.023(2) 0.025(2) 0.019(2) C8 0.063(3) 0.051(2) 0.057(2) 0.019(2) 0.014(2) 0.0113(19) C9 0.060(3) 0.057(2) 0.058(2) 0.020(2) 0.008(2) 0.000(2) C10 0.053(2) 0.074(3) 0.065(3) 0.024(2) -0.015(2) 0.009(2) C11 0.082(4) 0.085(4) 0.127(5) 0.006(4) -0.015(3) -0.004(3) C12 0.063(3) 0.186(7) 0.113(5) 0.022(5) 0.007(3) 0.007(4) C13 0.113(5) 0.141(6) 0.179(7) 0.100(6) -0.068(5) -0.010(4) Mn1' 0.0449(3) 0.0430(3) 0.0535(3) 0.0113(3) 0.0131(3) 0.0029(2) P1' 0.0682(7) 0.0647(7) 0.0631(7) 0.0269(6) 0.0048(6) 0.0021(6) P2' 0.0956(9) 0.0564(7) 0.0633(7) 0.0188(6) 0.0140(7) -0.0183(6) O1' 0.165(4) 0.062(2) 0.079(2) 0.0186(18) -0.018(2) -0.035(2) O2' 0.096(3) 0.107(3) 0.054(2) 0.0180(18) -0.0018(18) 0.014(2) O3' 0.064(2) 0.135(3) 0.132(3) 0.024(3) 0.041(2) 0.034(2) O4' 0.076(2) 0.059(2) 0.134(3) 0.026(2) 0.024(2) -0.0110(17) N1' 0.086(3) 0.060(2) 0.068(2) 0.0206(18) 0.027(2) 0.034(2) C1' 0.087(4) 0.192(8) 0.109(5) 0.044(5) -0.008(4) 0.033(5) C2' 0.170(7) 0.183(7) 0.054(3) 0.019(4) 0.021(4) 0.078(6) C3' 0.321(13) 0.171(8) 0.135(6) 0.119(6) -0.092(7) -0.121(8) C4' 0.186(8) 0.129(6) 0.183(7) 0.020(5) 0.123(7) -0.058(5) C5' 0.193(7) 0.083(4) 0.145(6) 0.077(4) -0.028(5) -0.019(4) C6' 0.073(3) 0.042(2) 0.057(2) 0.0160(18) 0.017(2) 0.012(2) C7' 0.056(2) 0.059(3) 0.060(3) 0.010(2) 0.011(2) 0.0074(19) C8' 0.055(3) 0.078(3) 0.069(3) 0.017(2) 0.019(2) 0.007(2) C9' 0.045(2) 0.053(2) 0.075(3) 0.017(2) 0.015(2) 0.0069(19) C10' 0.112(4) 0.073(3) 0.095(4) 0.026(3) 0.042(3) 0.058(3) C11' 0.215(10) 0.114(6) 0.204(9) -0.025(6) 0.031(7) 0.082(6) C12' 0.286(12) 0.375(16) 0.141(7) 0.102(9) 0.063(8) 0.276(13) C13' 0.246(10) 0.144(7) 0.338(14) 0.113(8) 0.236(11) 0.107(7) O5 0.114(4) 0.103(3) 0.134(4) 0.064(3) -0.026(3) -0.007(2) O6 0.097(3) 0.081(3) 0.146(4) 0.009(3) 0.023(3) 0.023(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 C9 1.797(5) . ? Mn1 C7 1.807(4) . ? Mn1 C8 1.808(5) . ? Mn1 C6 1.925(4) . ? Mn1 P1 2.325(4) . ? Mn1 P2 2.353(5) . ? P1 C2 1.806(4) . ? P1 C1 1.812(5) . ? P1 C3 1.819(5) . ? P2 O1 1.522(3) . ? P2 C5 1.821(5) . ? P2 C4 1.823(5) . ? O2 C7 1.151(5) . ? O3 C8 1.141(5) . ? O4 C9 1.156(5) . ? N1 C6 1.154(5) . ? N1 C10 1.458(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C10 C12 1.496(8) . ? C10 C11 1.501(7) . ? C10 C13 1.521(7) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? Mn1' C8' 1.807(5) . ? Mn1' C9' 1.812(4) . ? Mn1' C7' 1.827(6) . ? Mn1' C6' 1.916(5) . ? Mn1' P1' 2.328(5) . ? Mn1' P2' 2.341(5) . ? P1' C2' 1.795(6) . ? P1' C3' 1.799(6) . ? P1' C1' 1.806(6) . ? P2' O1' 1.494(4) . ? P2' C4' 1.793(6) . ? P2' C5' 1.855(6) . ? O2' C7' 1.127(5) . ? O3' C8' 1.142(5) . ? O4' C9' 1.147(5) . ? N1' C6' 1.147(5) . ? N1' C10' 1.466(6) . ? C1' H1D 0.9600 . ? C1' H1E 0.9600 . ? C1' H1F 0.9600 . ? C2' H2D 0.9600 . ? C2' H2E 0.9600 . ? C2' H2F 0.9600 . ? C3' H3D 0.9600 . ? C3' H3E 0.9600 . ? C3' H3F 0.9600 . ? C4' H4D 0.9600 . ? C4' H4E 0.9600 . ? C4' H4F 0.9600 . ? C5' H5D 0.9600 . ? C5' H5E 0.9600 . ? C5' H5F 0.9600 . ? C10' C12' 1.436(9) . ? C10' C13' 1.484(9) . ? C10' C11' 1.508(9) . ? C11' H11D 0.9600 . ? C11' H11E 0.9600 . ? C11' H11F 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? O5 H51 1.03(6) . ? O5 H52 0.87(6) . ? O6 H61 1.19(8) . ? O6 H62 1.01(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 C9 Mn1 C7 93.1(2) . . ? C9 Mn1 C8 89.7(2) . . ? C7 Mn1 C8 91.6(2) . . ? C9 Mn1 C6 173.59(17) . . ? C7 Mn1 C6 92.5(2) . . ? C8 Mn1 C6 93.2(2) . . ? C9 Mn1 P1 86.80(18) . . ? C7 Mn1 P1 90.29(17) . . ? C8 Mn1 P1 176.11(13) . . ? C6 Mn1 P1 90.12(16) . . ? C9 Mn1 P2 91.26(16) . . ? C7 Mn1 P2 175.58(15) . . ? C8 Mn1 P2 88.87(16) . . ? C6 Mn1 P2 83.09(14) . . ? P1 Mn1 P2 89.51(11) . . ? C2 P1 C1 103.4(2) . . ? C2 P1 C3 103.0(3) . . ? C1 P1 C3 101.9(3) . . ? C2 P1 Mn1 116.38(18) . . ? C1 P1 Mn1 116.68(18) . . ? C3 P1 Mn1 113.60(19) . . ? O1 P2 C5 107.4(3) . . ? O1 P2 C4 106.9(2) . . ? C5 P2 C4 101.0(3) . . ? O1 P2 Mn1 117.39(13) . . ? C5 P2 Mn1 111.96(19) . . ? C4 P2 Mn1 110.88(19) . . ? C6 N1 C10 177.8(4) . . ? P1 C1 H1A 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? P1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? P1 C2 H2A 109.5 . . ? P1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? P1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? P1 C3 H3A 109.5 . . ? P1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? P1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? P2 C4 H4A 109.5 . . ? P2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? P2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? P2 C5 H5A 109.5 . . ? P2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? P2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 Mn1 179.0(4) . . ? O2 C7 Mn1 178.2(4) . . ? O3 C8 Mn1 176.3(4) . . ? O4 C9 Mn1 179.4(5) . . ? N1 C10 C12 108.5(4) . . ? N1 C10 C11 107.9(4) . . ? C12 C10 C11 109.9(5) . . ? N1 C10 C13 106.4(4) . . ? C12 C10 C13 111.5(5) . . ? C11 C10 C13 112.5(5) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8' Mn1' C9' 92.5(2) . . ? C8' Mn1' C7' 92.5(2) . . ? C9' Mn1' C7' 90.6(2) . . ? C8' Mn1' C6' 172.96(19) . . ? C9' Mn1' C6' 93.28(18) . . ? C7' Mn1' C6' 91.4(2) . . ? C8' Mn1' P1' 88.28(18) . . ? C9' Mn1' P1' 90.98(18) . . ? C7' Mn1' P1' 178.17(14) . . ? C6' Mn1' P1' 87.68(16) . . ? C8' Mn1' P2' 89.42(16) . . ? C9' Mn1' P2' 177.07(14) . . ? C7' Mn1' P2' 87.11(17) . . ? C6' Mn1' P2' 84.92(14) . . ? P1' Mn1' P2' 91.25(11) . . ? C2' P1' C3' 102.2(4) . . ? C2' P1' C1' 99.9(4) . . ? C3' P1' C1' 102.3(4) . . ? C2' P1' Mn1' 118.5(2) . . ? C3' P1' Mn1' 114.1(2) . . ? C1' P1' Mn1' 117.2(2) . . ? O1' P2' C4' 109.5(3) . . ? O1' P2' C5' 106.8(3) . . ? C4' P2' C5' 98.7(4) . . ? O1' P2' Mn1' 117.47(19) . . ? C4' P2' Mn1' 112.2(2) . . ? C5' P2' Mn1' 110.4(2) . . ? C6' N1' C10' 176.1(5) . . ? P1' C1' H1D 109.5 . . ? P1' C1' H1E 109.5 . . ? H1D C1' H1E 109.5 . . ? P1' C1' H1F 109.5 . . ? H1D C1' H1F 109.5 . . ? H1E C1' H1F 109.5 . . ? P1' C2' H2D 109.5 . . ? P1' C2' H2E 109.5 . . ? H2D C2' H2E 109.5 . . ? P1' C2' H2F 109.5 . . ? H2D C2' H2F 109.5 . . ? H2E C2' H2F 109.5 . . ? P1' C3' H3D 109.5 . . ? P1' C3' H3E 109.5 . . ? H3D C3' H3E 109.5 . . ? P1' C3' H3F 109.5 . . ? H3D C3' H3F 109.5 . . ? H3E C3' H3F 109.5 . . ? P2' C4' H4D 109.5 . . ? P2' C4' H4E 109.5 . . ? H4D C4' H4E 109.5 . . ? P2' C4' H4F 109.5 . . ? H4D C4' H4F 109.5 . . ? H4E C4' H4F 109.5 . . ? P2' C5' H5D 109.5 . . ? P2' C5' H5E 109.5 . . ? H5D C5' H5E 109.5 . . ? P2' C5' H5F 109.5 . . ? H5D C5' H5F 109.5 . . ? H5E C5' H5F 109.5 . . ? N1' C6' Mn1' 178.9(4) . . ? O2' C7' Mn1' 179.2(4) . . ? O3' C8' Mn1' 179.8(6) . . ? O4' C9' Mn1' 178.0(4) . . ? C12' C10' N1' 108.8(5) . . ? C12' C10' C13' 114.6(8) . . ? N1' C10' C13' 108.4(5) . . ? C12' C10' C11' 112.1(7) . . ? N1' C10' C11' 107.0(5) . . ? C13' C10' C11' 105.7(7) . . ? C10' C11' H11D 109.5 . . ? C10' C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C10' C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C10' C12' H12D 109.5 . . ? C10' C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C10' C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C10' C13' H13D 109.5 . . ? C10' C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C10' C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? H51 O5 H52 79(5) . . ? H61 O6 H62 89(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 C9 Mn1 P1 C2 167.1(2) . . . . ? C7 Mn1 P1 C2 -99.8(2) . . . . ? C6 Mn1 P1 C2 -7.3(2) . . . . ? P2 Mn1 P1 C2 75.8(2) . . . . ? C9 Mn1 P1 C1 44.5(2) . . . . ? C7 Mn1 P1 C1 137.7(2) . . . . ? C6 Mn1 P1 C1 -129.8(2) . . . . ? P2 Mn1 P1 C1 -46.74(18) . . . . ? C9 Mn1 P1 C3 -73.6(3) . . . . ? C7 Mn1 P1 C3 19.6(3) . . . . ? C6 Mn1 P1 C3 112.1(3) . . . . ? P2 Mn1 P1 C3 -164.8(2) . . . . ? C9 Mn1 P2 O1 -113.4(2) . . . . ? C8 Mn1 P2 O1 156.88(19) . . . . ? C6 Mn1 P2 O1 63.5(2) . . . . ? P1 Mn1 P2 O1 -26.66(14) . . . . ? C9 Mn1 P2 C5 11.4(3) . . . . ? C8 Mn1 P2 C5 -78.3(3) . . . . ? C6 Mn1 P2 C5 -171.6(2) . . . . ? P1 Mn1 P2 C5 98.2(3) . . . . ? C9 Mn1 P2 C4 123.4(2) . . . . ? C8 Mn1 P2 C4 33.7(2) . . . . ? C6 Mn1 P2 C4 -59.7(2) . . . . ? P1 Mn1 P2 C4 -149.85(17) . . . . ? C8' Mn1' P1' C2' 150.7(3) . . . . ? C9' Mn1' P1' C2' -116.8(3) . . . . ? C6' Mn1' P1' C2' -23.6(3) . . . . ? P2' Mn1' P1' C2' 61.3(3) . . . . ? C8' Mn1' P1' C3' -88.9(5) . . . . ? C9' Mn1' P1' C3' 3.6(4) . . . . ? C6' Mn1' P1' C3' 96.9(5) . . . . ? P2' Mn1' P1' C3' -178.3(4) . . . . ? C8' Mn1' P1' C1' 30.7(3) . . . . ? C9' Mn1' P1' C1' 123.2(3) . . . . ? C6' Mn1' P1' C1' -143.5(3) . . . . ? P2' Mn1' P1' C1' -58.7(3) . . . . ? C8' Mn1' P2' O1' -103.1(3) . . . . ? C7' Mn1' P2' O1' 164.4(3) . . . . ? C6' Mn1' P2' O1' 72.8(3) . . . . ? P1' Mn1' P2' O1' -14.8(2) . . . . ? C8' Mn1' P2' C4' 25.2(4) . . . . ? C7' Mn1' P2' C4' -67.3(4) . . . . ? C6' Mn1' P2' C4' -158.9(4) . . . . ? P1' Mn1' P2' C4' 113.5(4) . . . . ? C8' Mn1' P2' C5' 134.2(3) . . . . ? C7' Mn1' P2' C5' 41.7(3) . . . . ? C6' Mn1' P2' C5' -50.0(3) . . . . ? P1' Mn1' P2' C5' -137.5(3) . . . . ? loop_ _geom_bond_atom_site_label_d _geom_bond_atom_site_label_h _geom_contact_atom_site_label_a _geom_bond_distance_dh _geom_contact_distance_ha _geom_contact_distance_da _geom_angle_dha _geom_contact_site_symmetry_a O5 H51 O1' 0.97(6) 2.810(7) 2.80(5) 81.(4) 1_555 O5 H51 O6 0.97(6) 3.483(8) 2.83(7) 125.(4) 1_555 O5 H52 O1' 0.97(4) 2.810(7) 1.98(5) 142.(4) 1_555 O6 H61 O5 0.98(3) 3.483(8) 2.97(7) 113.(3) 1_555 O6 H62 O1' 0.98(6) 2.875(6) 1.96(5) 154.(5) 1_555 O6 H62 O5 0.98(6) 3.483(8) 2.98(7) 113.(4) 1_555 O6 H61 O1 0.98(3) 2.746(5) 1.77(3) 170.(3) 1_555 O5 H51 O1 0.97(6) 2.975(6) 2.58(7) 104.(4) 1_555 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.501 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.059