# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global data_1 #TrackingRef '1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H10 Mn N2 O6 P' _chemical_formula_weight 352.12 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9992(6) _cell_length_b 9.3303(5) _cell_length_c 9.5016(4) _cell_angle_alpha 95.094(4) _cell_angle_beta 97.795(5) _cell_angle_gamma 108.464(6) _cell_volume 659.85(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2654 _cell_measurement_theta_min 2.9288 _cell_measurement_theta_max 29.1146 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.772 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 1.151 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97819 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4936 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2319 _reflns_number_gt 2004 _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^)+(0.0296P)^2^+0.2223P] 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 2319 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0394 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.50403(5) 0.25876(4) 0.35304(3) 0.01797(13) Uani 1 1 d . . . P1 P 0.20827(9) 0.41290(7) 0.46445(6) 0.01950(17) Uani 1 1 d . . . O1 O 0.3406(2) 0.39205(19) 0.37525(17) 0.0239(4) Uani 1 1 d . . . O2 O 0.2490(2) 0.57179(19) 0.54249(17) 0.0257(4) Uani 1 1 d . . . O3 O 0.0230(2) 0.3643(2) 0.36315(18) 0.0347(5) Uani 1 1 d . . . H1 H -0.0482 0.3904 0.4049 0.052 Uiso 1 1 calc R . . O4 O 0.1857(3) 0.3025(2) 0.58246(19) 0.0386(5) Uani 1 1 d . . . H2 H 0.2461 0.2471 0.5722 0.058 Uiso 1 1 calc R . . O5 O 0.3943(3) 0.13519(19) 0.52602(16) 0.0254(4) Uani 1 1 d . . . O6 O 0.3687(2) -0.07762(19) 0.62486(17) 0.0250(4) Uani 1 1 d . . . N1 N 0.5569(3) 0.2981(2) 0.1318(2) 0.0243(5) Uani 1 1 d . . . N2 N 0.2857(3) 0.0672(2) 0.1909(2) 0.0236(5) Uani 1 1 d . . . C1 C 0.6817(4) 0.4204(3) 0.1048(3) 0.0378(8) Uani 1 1 d . . . H3 H 0.7581 0.4887 0.1819 0.045 Uiso 1 1 calc R . . C2 C 0.7032(5) 0.4509(4) -0.0321(3) 0.0527(10) Uani 1 1 d . . . H4 H 0.7919 0.5381 -0.0464 0.063 Uiso 1 1 calc R . . C3 C 0.5924(5) 0.3514(4) -0.1466(3) 0.0472(9) Uani 1 1 d . . . H5 H 0.6044 0.3697 -0.2399 0.057 Uiso 1 1 calc R . . C4 C 0.4630(4) 0.2238(3) -0.1209(3) 0.0335(7) Uani 1 1 d . . . H6 H 0.3858 0.1545 -0.1970 0.040 Uiso 1 1 calc R . . C5 C 0.4484(4) 0.1991(3) 0.0193(2) 0.0215(6) Uani 1 1 d . . . C6 C 0.3089(4) 0.0643(3) 0.0526(2) 0.0224(6) Uani 1 1 d . . . C7 C 0.2066(4) -0.0562(3) -0.0513(3) 0.0319(7) Uani 1 1 d . . . H7 H 0.2271 -0.0571 -0.1454 0.038 Uiso 1 1 calc R . . C8 C 0.0747(4) -0.1747(3) -0.0148(3) 0.0429(8) Uani 1 1 d . . . H8 H 0.0038 -0.2560 -0.0838 0.052 Uiso 1 1 calc R . . C9 C 0.0491(4) -0.1710(4) 0.1259(3) 0.0448(9) Uani 1 1 d . . . H9 H -0.0396 -0.2495 0.1535 0.054 Uiso 1 1 calc R . . C10 C 0.1564(4) -0.0499(3) 0.2240(3) 0.0335(7) Uani 1 1 d . . . H10 H 0.1389 -0.0486 0.3188 0.040 Uiso 1 1 calc R . . C11 C 0.4314(3) 0.0158(3) 0.5442(2) 0.0197(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0206(2) 0.0175(2) 0.0169(2) 0.00207(15) 0.00411(15) 0.00761(17) P1 0.0184(4) 0.0199(4) 0.0214(3) 0.0004(3) 0.0041(3) 0.0084(3) O1 0.0253(11) 0.0249(10) 0.0279(9) 0.0062(7) 0.0103(8) 0.0143(8) O2 0.0196(10) 0.0237(10) 0.0331(10) -0.0053(8) 0.0018(8) 0.0097(8) O3 0.0226(11) 0.0450(13) 0.0333(10) -0.0151(9) -0.0017(8) 0.0149(10) O4 0.0533(15) 0.0410(13) 0.0400(11) 0.0185(9) 0.0273(10) 0.0299(11) O5 0.0395(12) 0.0232(10) 0.0227(9) 0.0071(7) 0.0117(8) 0.0196(9) O6 0.0308(11) 0.0247(10) 0.0259(9) 0.0103(8) 0.0123(8) 0.0132(9) N1 0.0309(14) 0.0210(12) 0.0188(10) 0.0017(9) 0.0056(9) 0.0053(10) N2 0.0230(13) 0.0266(13) 0.0193(11) 0.0033(9) 0.0039(9) 0.0055(10) C1 0.047(2) 0.0268(16) 0.0273(14) 0.0004(12) 0.0070(13) -0.0038(14) C2 0.073(3) 0.0317(18) 0.0359(17) 0.0088(14) 0.0186(16) -0.0123(17) C3 0.072(3) 0.0392(19) 0.0219(14) 0.0078(13) 0.0115(15) 0.0043(17) C4 0.048(2) 0.0285(16) 0.0187(13) 0.0009(11) 0.0038(12) 0.0075(14) C5 0.0254(15) 0.0211(14) 0.0203(12) 0.0014(10) 0.0042(11) 0.0114(12) C6 0.0235(15) 0.0237(14) 0.0212(13) 0.0009(10) 0.0026(11) 0.0106(12) C7 0.0341(18) 0.0329(17) 0.0235(14) -0.0027(12) 0.0060(12) 0.0052(14) C8 0.044(2) 0.0341(18) 0.0345(16) -0.0078(13) 0.0027(14) -0.0041(15) C9 0.039(2) 0.0383(19) 0.0413(17) 0.0032(14) 0.0109(14) -0.0107(15) C10 0.0312(18) 0.0373(18) 0.0258(14) 0.0052(12) 0.0071(12) 0.0016(14) C11 0.0249(16) 0.0190(14) 0.0154(11) -0.0008(10) 0.0008(10) 0.0094(12) _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 2.0880(17) . ? Mn1 O2 2.1445(18) 2_666 ? Mn1 O5 2.2108(16) . ? Mn1 N1 2.2391(19) . ? Mn1 O6 2.2431(17) 2_656 ? Mn1 N2 2.328(2) . ? P1 O1 1.4901(18) . ? P1 O2 1.5123(18) . ? P1 O3 1.5616(18) . ? P1 O4 1.5787(18) . ? O2 Mn1 2.1445(17) 2_666 ? O3 H1 0.8200 . ? O4 H2 0.8200 . ? O5 C11 1.261(3) . ? O6 C11 1.243(3) . ? O6 Mn1 2.2431(17) 2_656 ? N1 C1 1.328(3) . ? N1 C5 1.347(3) . ? N2 C10 1.340(3) . ? N2 C6 1.351(3) . ? C1 C2 1.377(4) . ? C1 H3 0.9300 . ? C2 C3 1.367(4) . ? C2 H4 0.9300 . ? C3 C4 1.374(4) . ? C3 H5 0.9300 . ? C4 C5 1.386(3) . ? C4 H6 0.9300 . ? C5 C6 1.485(4) . ? C6 C7 1.382(4) . ? C7 C8 1.373(4) . ? C7 H7 0.9300 . ? C8 C9 1.379(4) . ? C8 H8 0.9300 . ? C9 C10 1.365(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C11 1.552(5) 2_656 ? 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 97.06(7) . 2_666 ? O1 Mn1 O5 88.94(6) . . ? O2 Mn1 O5 104.86(7) 2_666 . ? O1 Mn1 N1 98.78(7) . . ? O2 Mn1 N1 94.10(7) 2_666 . ? O5 Mn1 N1 158.53(7) . . ? O1 Mn1 O6 162.76(6) . 2_656 ? O2 Mn1 O6 89.75(7) 2_666 2_656 ? O5 Mn1 O6 73.98(6) . 2_656 ? N1 Mn1 O6 96.49(7) . 2_656 ? O1 Mn1 N2 93.97(7) . . ? O2 Mn1 N2 163.61(7) 2_666 . ? O5 Mn1 N2 87.38(7) . . ? N1 Mn1 N2 72.20(7) . . ? O6 Mn1 N2 83.12(7) 2_656 . ? O1 P1 O2 116.15(10) . . ? O1 P1 O3 107.17(10) . . ? O2 P1 O3 109.23(10) . . ? O1 P1 O4 111.10(10) . . ? O2 P1 O4 106.40(10) . . ? O3 P1 O4 106.39(12) . . ? P1 O1 Mn1 140.05(10) . . ? P1 O2 Mn1 131.66(11) . 2_666 ? P1 O3 H1 109.5 . . ? P1 O4 H2 109.5 . . ? C11 O5 Mn1 116.45(15) . . ? C11 O6 Mn1 114.95(15) . 2_656 ? C1 N1 C5 118.0(2) . . ? C1 N1 Mn1 123.29(17) . . ? C5 N1 Mn1 118.55(16) . . ? C10 N2 C6 117.6(2) . . ? C10 N2 Mn1 126.22(16) . . ? C6 N2 Mn1 115.50(16) . . ? N1 C1 C2 123.1(3) . . ? N1 C1 H3 118.5 . . ? C2 C1 H3 118.5 . . ? C3 C2 C1 119.2(3) . . ? C3 C2 H4 120.4 . . ? C1 C2 H4 120.4 . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H5 120.7 . . ? C4 C3 H5 120.7 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H6 120.3 . . ? C5 C4 H6 120.3 . . ? N1 C5 C4 121.7(2) . . ? N1 C5 C6 116.8(2) . . ? C4 C5 C6 121.5(2) . . ? N2 C6 C7 121.7(2) . . ? N2 C6 C5 115.9(2) . . ? C7 C6 C5 122.4(2) . . ? C8 C7 C6 119.6(2) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 118.8(3) . . ? C7 C8 H8 120.6 . . ? C9 C8 H8 120.6 . . ? C10 C9 C8 118.8(3) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? N2 C10 C9 123.5(2) . . ? N2 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? O6 C11 O5 126.4(2) . . ? O6 C11 C11 117.7(3) . 2_656 ? O5 C11 C11 115.9(3) . 2_656 ? 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 O3 H1 O2 0.82 1.87 2.674(3) 165.9 2_566 O4 H2 O5 0.82 1.88 2.693(3) 171.6 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.264 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 929005' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '2.CIF' data_2 #TrackingRef '2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 Mn N O8 P' _chemical_formula_weight 319.05 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1008(8) _cell_length_b 6.7115(7) _cell_length_c 12.9864(8) _cell_angle_alpha 92.040(7) _cell_angle_beta 95.790(8) _cell_angle_gamma 107.914(8) _cell_volume 502.13(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1902 _cell_measurement_theta_min 3.1549 _cell_measurement_theta_max 28.9115 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 1.511 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92749 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3793 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0429 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1764 _reflns_number_gt 1504 _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^)+(0.0296P)^2^+0.1664P] 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 1764 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0676 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 0.27981(7) 0.09690(6) 0.46331(3) 0.01415(15) Uani 1 1 d . . . P1 P 0.75057(12) 0.41651(11) 0.58924(6) 0.01344(19) Uani 1 1 d . . . O1 O 0.6346(3) 0.2032(3) 0.53136(15) 0.0155(4) Uani 1 1 d . . . O2 O 0.7606(3) 0.5958(3) 0.52152(15) 0.0161(4) Uani 1 1 d . . . O3 O 0.6306(3) 0.4399(3) 0.68686(15) 0.0234(5) Uani 1 1 d . . . H1 H 0.5336 0.3277 0.6950 0.035 Uiso 1 1 calc R . . O4 O 1.0020(3) 0.4307(3) 0.63671(15) 0.0194(5) Uani 1 1 d . . . H2 H 1.0801 0.4230 0.5898 0.029 Uiso 1 1 calc R . . O5 O -0.0948(3) -0.0290(3) 0.39857(15) 0.0175(5) Uani 1 1 d . . . O6 O 0.2807(3) 0.0840(3) 0.29869(15) 0.0204(5) Uani 1 1 d . . . O7 O -0.3167(3) -0.1484(3) 0.24841(16) 0.0292(6) Uani 1 1 d . . . O8 O 0.0618(4) 0.0247(4) 0.14692(16) 0.0333(6) Uani 1 1 d . . . N1 N -0.5287(4) 0.2309(4) 0.08681(19) 0.0229(6) Uani 1 1 d . . . H3 H -0.6586 0.1645 0.1082 0.027 Uiso 1 1 calc R . . C1 C -0.1306(5) -0.0582(4) 0.3003(2) 0.0169(7) Uani 1 1 d . . . C2 C 0.0890(5) 0.0244(4) 0.2431(2) 0.0183(7) Uani 1 1 d . . . C3 C -0.3477(5) 0.3272(5) 0.1560(2) 0.0267(8) Uani 1 1 d . . . H4 H -0.3622 0.3218 0.2265 0.032 Uiso 1 1 calc R . . C4 C -0.1389(5) 0.4352(5) 0.1233(2) 0.0264(8) Uani 1 1 d . . . H5 H -0.0133 0.5043 0.1720 0.032 Uiso 1 1 calc R . . C5 C -0.1134(5) 0.4421(4) 0.0186(2) 0.0188(7) Uani 1 1 d . . . C6 C -0.3074(5) 0.3379(5) -0.0508(2) 0.0243(7) Uani 1 1 d . . . H6 H -0.2974 0.3381 -0.1218 0.029 Uiso 1 1 calc R . . C7 C -0.5141(5) 0.2343(5) -0.0149(2) 0.0248(7) Uani 1 1 d . . . H7 H -0.6440 0.1666 -0.0616 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0125(2) 0.0142(2) 0.0153(3) 0.00052(18) 0.00202(18) 0.00361(18) P1 0.0135(4) 0.0117(4) 0.0145(4) 0.0002(3) 0.0030(3) 0.0026(3) O1 0.0145(10) 0.0119(10) 0.0195(11) -0.0009(8) 0.0011(8) 0.0035(8) O2 0.0163(10) 0.0123(10) 0.0208(11) 0.0028(8) 0.0051(9) 0.0048(8) O3 0.0257(12) 0.0192(11) 0.0231(12) -0.0010(9) 0.0123(10) 0.0010(9) O4 0.0163(11) 0.0242(11) 0.0170(11) -0.0006(9) 0.0014(9) 0.0057(9) O5 0.0155(10) 0.0217(11) 0.0148(11) 0.0030(9) 0.0055(8) 0.0039(8) O6 0.0152(11) 0.0263(11) 0.0165(11) 0.0016(9) 0.0040(9) 0.0015(9) O7 0.0161(11) 0.0440(14) 0.0180(12) 0.0019(10) 0.0002(9) -0.0040(10) O8 0.0225(12) 0.0550(16) 0.0143(13) 0.0051(11) 0.0036(10) -0.0003(11) N1 0.0190(14) 0.0249(14) 0.0236(15) 0.0048(11) 0.0088(11) 0.0029(11) C1 0.0186(16) 0.0188(15) 0.0134(17) 0.0034(12) 0.0041(13) 0.0049(12) C2 0.0173(16) 0.0184(15) 0.0196(18) 0.0009(13) 0.0067(13) 0.0050(12) C3 0.0249(17) 0.0352(19) 0.0150(17) 0.0014(14) 0.0041(14) 0.0015(14) C4 0.0202(16) 0.0365(19) 0.0165(17) -0.0008(14) 0.0008(13) 0.0008(14) C5 0.0175(16) 0.0209(16) 0.0182(17) 0.0026(13) 0.0054(13) 0.0054(12) C6 0.0222(16) 0.0319(18) 0.0158(17) 0.0018(14) 0.0053(13) 0.0035(14) C7 0.0224(17) 0.0284(18) 0.0193(18) -0.0011(14) 0.0008(14) 0.0025(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O6 2.137(2) . ? Mn1 O1 2.1433(19) . ? Mn1 O2 2.1558(19) 2_666 ? Mn1 O5 2.2023(18) 2_556 ? Mn1 O1 2.2324(19) 2_656 ? Mn1 O5 2.240(2) . ? P1 O2 1.5053(19) . ? P1 O1 1.5193(19) . ? P1 O3 1.553(2) . ? P1 O4 1.568(2) . ? O1 Mn1 2.2324(18) 2_656 ? O2 Mn1 2.1558(18) 2_666 ? O3 H1 0.8200 . ? O4 H2 0.8200 . ? O5 C1 1.270(3) . ? O5 Mn1 2.2023(18) 2_556 ? O6 C2 1.253(3) . ? O7 C1 1.226(3) . ? O8 C2 1.244(3) . ? N1 C3 1.328(4) . ? N1 C7 1.333(4) . ? N1 H3 0.8600 . ? C1 C2 1.558(4) . ? C3 C4 1.375(4) . ? C3 H4 0.9300 . ? C4 C5 1.385(4) . ? C4 H5 0.9300 . ? C5 C6 1.390(4) . ? C5 C5 1.501(5) 2_565 ? C6 C7 1.376(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Mn1 O1 107.27(7) . . ? O6 Mn1 O2 96.32(8) . 2_666 ? O1 Mn1 O2 93.70(7) . 2_666 ? O6 Mn1 O5 150.69(7) . 2_556 ? O1 Mn1 O5 101.66(7) . 2_556 ? O2 Mn1 O5 86.24(7) 2_666 2_556 ? O6 Mn1 O1 89.93(8) . 2_656 ? O1 Mn1 O1 78.17(7) . 2_656 ? O2 Mn1 O1 170.96(7) 2_666 2_656 ? O5 Mn1 O1 91.52(7) 2_556 2_656 ? O6 Mn1 O5 74.99(7) . . ? O1 Mn1 O5 176.68(7) . . ? O2 Mn1 O5 88.42(7) 2_666 . ? O5 Mn1 O5 75.91(8) 2_556 . ? O1 Mn1 O5 99.54(7) 2_656 . ? O2 P1 O1 112.82(11) . . ? O2 P1 O3 110.68(11) . . ? O1 P1 O3 110.97(11) . . ? O2 P1 O4 109.68(11) . . ? O1 P1 O4 109.48(11) . . ? O3 P1 O4 102.74(12) . . ? P1 O1 Mn1 123.92(11) . . ? P1 O1 Mn1 131.51(11) . 2_656 ? Mn1 O1 Mn1 101.83(7) . 2_656 ? P1 O2 Mn1 137.14(12) . 2_666 ? P1 O3 H1 109.5 . . ? P1 O4 H2 109.5 . . ? C1 O5 Mn1 140.71(17) . 2_556 ? C1 O5 Mn1 114.64(17) . . ? Mn1 O5 Mn1 104.09(8) 2_556 . ? C2 O6 Mn1 118.00(18) . . ? C3 N1 C7 121.7(3) . . ? C3 N1 H3 119.1 . . ? C7 N1 H3 119.1 . . ? O7 C1 O5 126.4(3) . . ? O7 C1 C2 118.4(2) . . ? O5 C1 C2 115.1(2) . . ? O8 C2 O6 125.2(3) . . ? O8 C2 C1 118.2(3) . . ? O6 C2 C1 116.6(2) . . ? N1 C3 C4 120.0(3) . . ? N1 C3 H4 120.0 . . ? C4 C3 H4 120.0 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H5 119.6 . . ? C5 C4 H5 119.6 . . ? C4 C5 C6 117.2(3) . . ? C4 C5 C5 121.5(3) . 2_565 ? C6 C5 C5 121.3(3) . 2_565 ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? N1 C7 C6 120.2(3) . . ? N1 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? 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 N1 H3 O8 0.86 1.81 2.666(3) 177.3 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.336 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 929006' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '3.CIF' data_3 #TrackingRef '3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Mn N2 O6 P' _chemical_formula_weight 376.14 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7715(9) _cell_length_b 9.4619(8) _cell_length_c 10.7591(8) _cell_angle_alpha 114.628(7) _cell_angle_beta 90.843(6) _cell_angle_gamma 102.125(8) _cell_volume 698.47(11) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2470 _cell_measurement_theta_min 3.1717 _cell_measurement_theta_max 29.0562 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_absorpt_coefficient_mu 1.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97061 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _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 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5252 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2445 _reflns_number_gt 2048 _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^)+(0.0320P)^2^+0.0869P] 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 2445 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0770 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 0.69162(5) 0.11900(4) 0.59242(4) 0.02186(14) Uani 1 1 d . . . P1 P 0.44984(9) 0.26045(8) 0.43807(7) 0.02248(18) Uani 1 1 d . . . O1 O 0.4747(2) 0.12286(19) 0.46989(17) 0.0241(4) Uani 1 1 d . . . O2 O 0.6180(2) 0.3572(2) 0.42044(18) 0.0297(4) Uani 1 1 d . . . O3 O 0.3482(3) 0.3597(2) 0.55174(18) 0.0346(5) Uani 1 1 d . . . H1 H 0.3641 0.4501 0.5559 0.052 Uiso 1 1 calc R . . O4 O 0.3276(3) 0.1884(2) 0.29783(18) 0.0348(5) Uani 1 1 d . . . H2 H 0.2451 0.1171 0.2959 0.052 Uiso 1 1 calc R . . O5 O 0.9078(2) 0.0288(2) 0.65310(16) 0.0256(4) Uani 1 1 d . . . O6 O 1.1391(2) -0.0740(2) 0.57372(17) 0.0309(5) Uani 1 1 d . . . N1 N 0.6009(3) 0.2007(2) 0.8058(2) 0.0255(5) Uani 1 1 d . . . N2 N 0.8274(3) 0.3794(2) 0.7077(2) 0.0254(5) Uani 1 1 d . . . C1 C 0.4883(4) 0.1135(3) 0.8539(3) 0.0346(7) Uani 1 1 d . . . H3 H 0.4285 0.0104 0.7930 0.042 Uiso 1 1 calc R . . C2 C 0.4564(4) 0.1698(4) 0.9914(3) 0.0380(8) Uani 1 1 d . . . H4 H 0.3781 0.1045 1.0210 0.046 Uiso 1 1 calc R . . C3 C 0.5404(4) 0.3208(4) 1.0818(3) 0.0363(7) Uani 1 1 d . . . H5 H 0.5218 0.3587 1.1741 0.044 Uiso 1 1 calc R . . C4 C 0.6560(4) 0.4198(3) 1.0351(3) 0.0286(7) Uani 1 1 d . . . C5 C 0.6822(3) 0.3527(3) 0.8951(2) 0.0235(6) Uani 1 1 d . . . C6 C 0.8010(3) 0.4486(3) 0.8419(2) 0.0234(6) Uani 1 1 d . . . C7 C 0.8842(4) 0.6080(3) 0.9304(3) 0.0290(6) Uani 1 1 d . . . C8 C 0.9955(4) 0.6963(3) 0.8733(3) 0.0386(7) Uani 1 1 d . . . H6 H 1.0517 0.8028 0.9279 0.046 Uiso 1 1 calc R . . C9 C 1.0218(4) 0.6271(3) 0.7384(3) 0.0376(7) Uani 1 1 d . . . H7 H 1.0949 0.6855 0.6999 0.045 Uiso 1 1 calc R . . C10 C 0.9374(4) 0.4677(3) 0.6594(3) 0.0317(7) Uani 1 1 d . . . H8 H 0.9587 0.4202 0.5679 0.038 Uiso 1 1 calc R . . C11 C 0.7466(4) 0.5812(4) 1.1227(3) 0.0372(7) Uani 1 1 d . . . H9 H 0.7308 0.6248 1.2156 0.045 Uiso 1 1 calc R . . C12 C 0.8543(4) 0.6705(4) 1.0724(3) 0.0380(8) Uani 1 1 d . . . H10 H 0.9108 0.7755 1.1312 0.046 Uiso 1 1 calc R . . C13 C 1.0147(4) -0.0137(3) 0.5657(2) 0.0229(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0230(3) 0.0205(2) 0.0213(2) 0.00746(17) 0.00504(17) 0.00652(18) P1 0.0276(4) 0.0190(4) 0.0254(4) 0.0123(3) 0.0069(3) 0.0087(3) O1 0.0259(10) 0.0183(9) 0.0304(10) 0.0130(8) 0.0001(8) 0.0050(8) O2 0.0293(11) 0.0224(10) 0.0423(11) 0.0178(9) 0.0121(9) 0.0072(9) O3 0.0481(13) 0.0249(11) 0.0406(11) 0.0189(9) 0.0248(10) 0.0166(10) O4 0.0381(12) 0.0400(12) 0.0328(11) 0.0231(9) 0.0004(9) 0.0072(10) O5 0.0235(10) 0.0311(11) 0.0215(9) 0.0092(8) 0.0081(8) 0.0091(9) O6 0.0288(11) 0.0440(12) 0.0285(10) 0.0184(9) 0.0093(8) 0.0197(10) N1 0.0283(13) 0.0243(12) 0.0276(12) 0.0122(10) 0.0109(10) 0.0109(11) N2 0.0276(13) 0.0262(12) 0.0212(12) 0.0086(10) 0.0043(9) 0.0074(11) C1 0.0407(19) 0.0308(16) 0.0394(17) 0.0187(14) 0.0176(14) 0.0144(15) C2 0.045(2) 0.048(2) 0.0412(18) 0.0305(16) 0.0232(15) 0.0250(17) C3 0.0425(19) 0.053(2) 0.0298(16) 0.0256(15) 0.0156(14) 0.0275(17) C4 0.0303(16) 0.0370(17) 0.0221(14) 0.0117(12) 0.0052(12) 0.0174(14) C5 0.0244(15) 0.0275(15) 0.0212(14) 0.0097(12) 0.0052(11) 0.0130(13) C6 0.0226(15) 0.0252(15) 0.0215(14) 0.0080(11) -0.0009(11) 0.0083(12) C7 0.0263(16) 0.0288(16) 0.0280(15) 0.0076(12) -0.0014(12) 0.0087(13) C8 0.0339(18) 0.0268(16) 0.0447(18) 0.0070(14) -0.0025(14) 0.0043(14) C9 0.0321(18) 0.0347(18) 0.0457(19) 0.0205(15) 0.0063(14) 0.0002(15) C10 0.0332(17) 0.0346(17) 0.0271(15) 0.0145(13) 0.0051(13) 0.0052(14) C11 0.0426(19) 0.0455(19) 0.0197(15) 0.0064(14) 0.0024(13) 0.0189(16) C12 0.0377(19) 0.0342(17) 0.0278(16) -0.0020(13) -0.0088(13) 0.0129(15) C13 0.0234(15) 0.0197(14) 0.0199(14) 0.0053(11) 0.0006(11) 0.0002(12) _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 2.1407(17) . ? Mn1 O6 2.1859(17) 2_756 ? Mn1 O1 2.1931(17) 2_656 ? Mn1 O5 2.2390(17) . ? Mn1 N2 2.246(2) . ? Mn1 N1 2.272(2) . ? P1 O2 1.4933(19) . ? P1 O1 1.5245(16) . ? P1 O3 1.5443(18) . ? P1 O4 1.5725(19) . ? O1 Mn1 2.1931(17) 2_656 ? O3 H1 0.8200 . ? O4 H2 0.8200 . ? O5 C13 1.259(3) . ? O6 C13 1.240(3) . ? O6 Mn1 2.1859(17) 2_756 ? N1 C1 1.335(3) . ? N1 C5 1.356(3) . ? N2 C10 1.332(3) . ? N2 C6 1.354(3) . ? C1 C2 1.394(4) . ? C1 H3 0.9300 . ? C2 C3 1.358(4) . ? C2 H4 0.9300 . ? C3 C4 1.411(4) . ? C3 H5 0.9300 . ? C4 C5 1.407(3) . ? C4 C11 1.430(4) . ? C5 C6 1.449(4) . ? C6 C7 1.405(4) . ? C7 C8 1.402(4) . ? C7 C12 1.433(4) . ? C8 C9 1.360(4) . ? C8 H6 0.9300 . ? C9 C10 1.388(4) . ? C9 H7 0.9300 . ? C10 H8 0.9300 . ? C11 C12 1.344(4) . ? C11 H9 0.9300 . ? C12 H10 0.9300 . ? C13 C13 1.561(5) 2_756 ? 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 O6 93.23(7) . 2_756 ? O1 Mn1 O1 79.07(6) . 2_656 ? O6 Mn1 O1 100.28(7) 2_756 2_656 ? O1 Mn1 O5 158.85(6) . . ? O6 Mn1 O5 74.54(6) 2_756 . ? O1 Mn1 O5 86.10(6) 2_656 . ? O1 Mn1 N2 102.90(7) . . ? O6 Mn1 N2 94.72(7) 2_756 . ? O1 Mn1 N2 164.76(7) 2_656 . ? O5 Mn1 N2 95.38(7) . . ? O1 Mn1 N1 103.03(7) . . ? O6 Mn1 N1 161.77(8) 2_756 . ? O1 Mn1 N1 90.97(7) 2_656 . ? O5 Mn1 N1 92.13(7) . . ? N2 Mn1 N1 73.82(8) . . ? O2 P1 O1 113.94(10) . . ? O2 P1 O3 113.75(10) . . ? O1 P1 O3 106.80(10) . . ? O2 P1 O4 106.37(10) . . ? O1 P1 O4 108.39(10) . . ? O3 P1 O4 107.32(11) . . ? P1 O1 Mn1 127.68(10) . . ? P1 O1 Mn1 131.40(10) . 2_656 ? Mn1 O1 Mn1 100.93(6) . 2_656 ? P1 O3 H1 109.5 . . ? P1 O4 H2 109.5 . . ? C13 O5 Mn1 115.33(15) . . ? C13 O6 Mn1 116.70(15) . 2_756 ? C1 N1 C5 117.7(2) . . ? C1 N1 Mn1 127.48(18) . . ? C5 N1 Mn1 114.66(17) . . ? C10 N2 C6 117.8(2) . . ? C10 N2 Mn1 126.60(18) . . ? C6 N2 Mn1 115.49(17) . . ? N1 C1 C2 123.0(3) . . ? N1 C1 H3 118.5 . . ? C2 C1 H3 118.5 . . ? C3 C2 C1 119.5(3) . . ? C3 C2 H4 120.2 . . ? C1 C2 H4 120.2 . . ? C2 C3 C4 119.7(3) . . ? C2 C3 H5 120.2 . . ? C4 C3 H5 120.2 . . ? C5 C4 C3 117.0(3) . . ? C5 C4 C11 119.7(3) . . ? C3 C4 C11 123.3(3) . . ? N1 C5 C4 123.0(2) . . ? N1 C5 C6 117.6(2) . . ? C4 C5 C6 119.4(2) . . ? N2 C6 C7 122.7(2) . . ? N2 C6 C5 118.0(2) . . ? C7 C6 C5 119.3(2) . . ? C8 C7 C6 117.0(3) . . ? C8 C7 C12 123.7(3) . . ? C6 C7 C12 119.3(3) . . ? C9 C8 C7 120.3(3) . . ? C9 C8 H6 119.8 . . ? C7 C8 H6 119.8 . . ? C8 C9 C10 118.7(3) . . ? C8 C9 H7 120.7 . . ? C10 C9 H7 120.7 . . ? N2 C10 C9 123.4(3) . . ? N2 C10 H8 118.3 . . ? C9 C10 H8 118.3 . . ? C12 C11 C4 120.8(3) . . ? C12 C11 H9 119.6 . . ? C4 C11 H9 119.6 . . ? C11 C12 C7 121.6(3) . . ? C11 C12 H10 119.2 . . ? C7 C12 H10 119.2 . . ? O6 C13 O5 126.8(2) . . ? O6 C13 C13 117.6(3) . 2_756 ? O5 C13 C13 115.6(3) . 2_756 ? 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 O3 H1 O2 0.82 1.71 2.524(2) 173.3 2_666 O4 H2 O5 0.82 1.89 2.683(3) 161.8 2_656 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.329 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.063 _database_code_depnum_ccdc_archive 'CCDC 929007'