# Electronic Supplementary Material (ESI) for RSC Advances # 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_Co-3 #TrackingRef 'Co-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 Co3 N2 O20 P4' _chemical_formula_sum 'C16 H20 Co3 N2 O20 P4' _chemical_formula_weight 861.01 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' Co Co 0.3494 0.9721 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8776(18) _cell_length_b 8.9196(18) _cell_length_c 9.984(2) _cell_angle_alpha 98.89(3) _cell_angle_beta 108.72(3) _cell_angle_gamma 110.34(3) _cell_volume 669.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.134 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 431 _exptl_absorpt_coefficient_mu 2.173 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6126 _exptl_absorpt_correction_T_max 0.8120 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5637 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0786 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2346 _reflns_number_gt 1797 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0322P)^2^+1.2965P] 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 2346 _refine_ls_number_parameters 209 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.097 _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 O10 O 0.5164(5) -0.0720(5) 0.6545(4) 0.0264(10) Uani 1 1 d . . . O6 O 1.2305(5) 0.7177(5) 0.7003(4) 0.0187(9) Uani 1 1 d . . . O2 O 0.7614(5) 0.4742(5) 0.8358(4) 0.0210(10) Uani 1 1 d . . . Co1 Co 1.0000 0.5000 1.0000 0.0155(3) Uani 1 2 d S . . Co2 Co 0.74823(10) 0.26425(10) 0.48424(9) 0.0178(2) Uani 1 1 d . . . P1 P 0.71355(19) 0.52994(19) 0.69900(16) 0.0151(4) Uani 1 1 d . . . P2 P 1.08333(18) 0.60419(19) 0.73368(16) 0.0144(4) Uani 1 1 d . . . O5 O 0.9956(5) 0.4248(4) 0.6310(4) 0.0171(9) Uani 1 1 d . . . O4 O 1.1487(5) 0.6158(5) 0.8970(4) 0.0184(9) Uani 1 1 d . . . O9 O 0.7280(5) 0.1017(5) 0.6044(4) 0.0229(10) Uani 1 1 d . . . O7 O 0.8667(6) 0.7090(6) 0.5489(5) 0.0294(11) Uani 1 1 d . . . H7 H 0.8935 0.6511 0.4972 0.044 Uiso 1 1 calc R . . O3 O 0.6227(5) 0.3906(5) 0.5521(4) 0.0178(9) Uani 1 1 d . . . O1 O 0.5913(5) 0.6169(6) 0.7090(4) 0.0220(11) Uani 1 1 d . . . O8 O 1.0192(5) 0.7343(5) 1.1168(4) 0.0265(10) Uani 1 1 d D . . H8A H 1.1120 0.7797 1.1964 0.040 Uiso 1 1 d RD . . H8B H 0.9301 0.7168 1.1375 0.040 Uiso 1 1 d RD . . C7 C 0.9135(7) 0.6855(7) 0.6957(6) 0.0174(13) Uani 1 1 d . . . C4 C 1.2827(8) 1.0460(8) 0.9657(7) 0.0315(16) Uani 1 1 d . . . H4 H 1.2669 1.0007 1.0407 0.038 Uiso 1 1 calc R . . C6 C 0.9686(7) 0.8554(7) 0.8018(7) 0.0231(14) Uani 1 1 d . . . H6A H 0.8793 0.8950 0.7635 0.028 Uiso 1 1 calc R . . H6B H 0.9705 0.8399 0.8963 0.028 Uiso 1 1 calc R . . C3 C 1.1445(8) 0.9909(7) 0.8294(7) 0.0208(14) Uani 1 1 d . . . N1 N 1.4703(7) 1.2365(7) 0.8841(7) 0.0373(15) Uani 1 1 d . . . C1 C 1.3361(10) 1.1880(9) 0.7520(8) 0.0392(18) Uani 1 1 d . . . H1 H 1.3528 1.2375 0.6794 0.047 Uiso 1 1 calc R . . C2 C 1.1750(8) 1.0661(8) 0.7236(7) 0.0303(16) Uani 1 1 d . . . H2 H 1.0840 1.0330 0.6311 0.036 Uiso 1 1 calc R . . C5 C 1.4457(9) 1.1692(9) 0.9915(8) 0.043(2) Uani 1 1 d . . . H5 H 1.5385 1.2054 1.0836 0.051 Uiso 1 1 calc R . . C8 C 0.5691(8) 0.0067(7) 0.5752(6) 0.0216(14) Uani 1 1 d . . . H1A H 0.536(9) 0.616(9) 0.644(7) 0.032 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 O10 0.024(2) 0.028(3) 0.018(2) 0.011(2) 0.007(2) 0.001(2) O6 0.014(2) 0.024(2) 0.014(2) 0.0084(18) 0.0059(18) 0.0027(18) O2 0.014(2) 0.032(3) 0.017(2) 0.0130(19) 0.0050(19) 0.0083(19) Co1 0.0138(6) 0.0191(7) 0.0124(6) 0.0070(5) 0.0049(5) 0.0051(5) Co2 0.0173(4) 0.0192(5) 0.0145(5) 0.0062(3) 0.0072(4) 0.0038(4) P1 0.0113(8) 0.0191(9) 0.0131(8) 0.0067(6) 0.0029(7) 0.0054(6) P2 0.0118(8) 0.0184(8) 0.0115(8) 0.0058(6) 0.0046(7) 0.0043(7) O5 0.014(2) 0.016(2) 0.014(2) 0.0017(17) 0.0033(18) -0.0002(17) O4 0.014(2) 0.023(2) 0.013(2) 0.0081(18) 0.0042(18) 0.0022(18) O9 0.014(2) 0.020(2) 0.024(2) 0.0113(19) 0.0016(19) -0.0003(18) O7 0.034(3) 0.034(3) 0.025(3) 0.014(2) 0.010(2) 0.019(2) O3 0.012(2) 0.020(2) 0.016(2) 0.0019(17) 0.0026(18) 0.0041(17) O1 0.019(3) 0.033(3) 0.014(2) 0.006(2) 0.005(2) 0.014(2) O8 0.030(3) 0.029(3) 0.019(2) 0.0059(19) 0.005(2) 0.016(2) C7 0.014(3) 0.019(3) 0.018(3) 0.008(3) 0.007(3) 0.005(3) C4 0.027(4) 0.031(4) 0.030(4) 0.008(3) 0.006(3) 0.010(3) C6 0.018(3) 0.021(4) 0.031(4) 0.007(3) 0.011(3) 0.008(3) C3 0.024(3) 0.012(3) 0.025(4) 0.002(3) 0.008(3) 0.008(3) N1 0.026(3) 0.033(4) 0.046(4) 0.003(3) 0.015(3) 0.007(3) C1 0.045(5) 0.034(4) 0.044(5) 0.013(4) 0.026(4) 0.014(4) C2 0.025(4) 0.029(4) 0.029(4) 0.007(3) 0.010(3) 0.006(3) C5 0.023(4) 0.039(5) 0.040(5) -0.011(4) -0.007(4) 0.012(3) C8 0.028(4) 0.013(3) 0.023(4) 0.004(3) 0.009(3) 0.009(3) _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 O10 C8 1.233(7) . ? O10 Co2 2.181(4) 2_656 ? O6 P2 1.519(4) . ? O6 Co2 1.936(4) 2_766 ? O2 P1 1.509(4) . ? O2 Co1 2.131(4) . ? Co1 O4 2.030(4) 2_767 ? Co1 O4 2.030(4) . ? Co1 O2 2.131(4) 2_767 ? Co1 O8 2.152(4) . ? Co1 O8 2.152(4) 2_767 ? Co2 O6 1.936(4) 2_766 ? Co2 O9 2.016(4) . ? Co2 O3 2.024(4) . ? Co2 O5 2.030(4) . ? Co2 O10 2.181(4) 2_656 ? P1 O3 1.525(4) . ? P1 O1 1.556(4) . ? P1 C7 1.848(6) . ? P2 O4 1.518(4) . ? P2 O5 1.527(4) . ? P2 C7 1.849(6) . ? O9 C8 1.274(7) . ? O7 C7 1.460(7) . ? O7 H7 0.8200 . ? O1 H1A 0.67(6) . ? O8 H8A 0.8500 . ? O8 H8B 0.8499 . ? C7 C6 1.522(8) . ? C4 C3 1.379(8) . ? C4 C5 1.392(9) . ? C4 H4 0.9300 . ? C6 C3 1.511(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C3 C2 1.384(8) . ? N1 C1 1.342(9) . ? N1 C5 1.347(9) . ? C1 C2 1.368(9) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C5 H5 0.9300 . ? C8 C8 1.559(12) 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 C8 O10 Co2 107.4(4) . 2_656 ? P2 O6 Co2 132.1(2) . 2_766 ? P1 O2 Co1 135.2(2) . . ? O4 Co1 O4 180.000(1) 2_767 . ? O4 Co1 O2 93.46(14) 2_767 2_767 ? O4 Co1 O2 86.54(14) . 2_767 ? O4 Co1 O2 86.54(14) 2_767 . ? O4 Co1 O2 93.46(14) . . ? O2 Co1 O2 180.000(1) 2_767 . ? O4 Co1 O8 88.32(16) 2_767 . ? O4 Co1 O8 91.68(16) . . ? O2 Co1 O8 93.15(16) 2_767 . ? O2 Co1 O8 86.85(16) . . ? O4 Co1 O8 91.68(16) 2_767 2_767 ? O4 Co1 O8 88.32(15) . 2_767 ? O2 Co1 O8 86.85(16) 2_767 2_767 ? O2 Co1 O8 93.15(16) . 2_767 ? O8 Co1 O8 180.000(1) . 2_767 ? O6 Co2 O9 140.02(17) 2_766 . ? O6 Co2 O3 115.48(16) 2_766 . ? O9 Co2 O3 99.91(16) . . ? O6 Co2 O5 100.12(15) 2_766 . ? O9 Co2 O5 93.01(15) . . ? O3 Co2 O5 97.06(16) . . ? O6 Co2 O10 85.70(16) 2_766 2_656 ? O9 Co2 O10 79.68(15) . 2_656 ? O3 Co2 O10 84.27(16) . 2_656 ? O5 Co2 O10 172.69(15) . 2_656 ? O2 P1 O3 115.2(2) . . ? O2 P1 O1 107.5(2) . . ? O3 P1 O1 109.1(2) . . ? O2 P1 C7 109.9(2) . . ? O3 P1 C7 106.8(2) . . ? O1 P1 C7 108.1(3) . . ? O4 P2 O6 110.4(2) . . ? O4 P2 O5 113.4(2) . . ? O6 P2 O5 112.1(2) . . ? O4 P2 C7 107.1(2) . . ? O6 P2 C7 106.8(2) . . ? O5 P2 C7 106.7(2) . . ? P2 O5 Co2 135.7(2) . . ? P2 O4 Co1 125.8(2) . . ? C8 O9 Co2 112.6(4) . . ? C7 O7 H7 109.5 . . ? P1 O3 Co2 121.7(2) . . ? P1 O1 H1A 116(6) . . ? Co1 O8 H8A 109.5 . . ? Co1 O8 H8B 109.5 . . ? H8A O8 H8B 109.5 . . ? O7 C7 C6 105.0(5) . . ? O7 C7 P1 107.7(4) . . ? C6 C7 P1 109.7(4) . . ? O7 C7 P2 111.0(4) . . ? C6 C7 P2 114.6(4) . . ? P1 C7 P2 108.7(3) . . ? C3 C4 C5 120.3(7) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C3 C6 C7 116.4(5) . . ? C3 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? C3 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.3 . . ? C4 C3 C2 117.1(6) . . ? C4 C3 C6 119.9(6) . . ? C2 C3 C6 123.0(6) . . ? C1 N1 C5 120.1(6) . . ? N1 C1 C2 120.4(7) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 121.5(6) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? N1 C5 C4 120.5(6) . . ? N1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? O10 C8 O9 126.3(5) . . ? O10 C8 C8 118.3(7) . 2_656 ? O9 C8 C8 115.4(6) . 2_656 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.619 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.114 _database_code_depnum_ccdc_archive 'CCDC 860650' ####################################################################### # # 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_co-1 #TrackingRef 'co-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 Co N O7 P2, H2 O' _chemical_formula_sum 'C7 H11 Co N O8 P2' _chemical_formula_weight 358.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.4294(11) _cell_length_b 15.982(3) _cell_length_c 12.892(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.23(3) _cell_angle_gamma 90.00 _cell_volume 1107.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.148 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 724 _exptl_absorpt_coefficient_mu 1.878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_T_max 0.685 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11240 _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2520 _reflns_number_gt 1972 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0236P)^2^+3.3928P] 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 2520 _refine_ls_number_parameters 187 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0854 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Co1 Co 0.15431(10) 0.57705(3) 0.95298(4) 0.01317(15) Uani 1 1 d . . . P1 P 0.68772(18) 0.62093(6) 1.07895(8) 0.0092(2) Uani 1 1 d . . . P2 P 0.65078(18) 0.65739(6) 0.85064(8) 0.0100(2) Uani 1 1 d . . . N1 N 0.5356(8) 0.9852(2) 0.7989(3) 0.0265(9) Uani 1 1 d D . . H1A H 0.536(10) 1.025(2) 0.755(3) 0.040 Uiso 1 1 d D . . O1 O 0.4175(5) 0.59793(17) 1.0750(2) 0.0134(6) Uani 1 1 d . . . O2 O 0.7992(5) 0.65628(17) 1.1875(2) 0.0144(6) Uani 1 1 d D . . H2A H 0.727(7) 0.693(2) 1.214(3) 0.022 Uiso 1 1 d D . . O3 O 0.8637(5) 0.55145(16) 1.0545(2) 0.0124(6) Uani 1 1 d . . . O4 O 0.4302(5) 0.59859(16) 0.8538(2) 0.0130(6) Uani 1 1 d . . . O5 O 0.8884(5) 0.61024(18) 0.8356(2) 0.0160(6) Uani 1 1 d . . . O6 O 0.5863(5) 0.72423(17) 0.7684(2) 0.0159(6) Uani 1 1 d . . . O7 O 0.9765(5) 0.72831(19) 0.9938(2) 0.0168(6) Uani 1 1 d . . . H7A H 1.001(9) 0.754(3) 1.053(4) 0.025 Uiso 1 1 d . . . O8 O 0.1155(6) 0.8272(2) 0.1623(3) 0.0261(8) Uani 1 1 d . . . H8A H 0.238(10) 0.813(4) 0.193(4) 0.039 Uiso 1 1 d . . . H8B H 0.027(10) 0.839(3) 0.209(4) 0.039 Uiso 1 1 d . . . C1 C 0.5431(8) 0.8522(3) 0.9322(3) 0.0154(9) Uani 1 1 d . . . C2 C 0.7414(9) 0.9079(3) 0.9404(4) 0.0240(10) Uani 1 1 d . . . H2 H 0.8783 0.9005 0.9918 0.029 Uiso 1 1 calc R . . C3 C 0.7334(9) 0.9742(3) 0.8715(4) 0.0275(11) Uani 1 1 d . . . H3 H 0.8664 1.0113 0.8758 0.033 Uiso 1 1 calc R . . C4 C 0.3377(9) 0.9345(3) 0.7910(3) 0.0249(10) Uani 1 1 d . . . H4 H 0.2007 0.9448 0.7405 0.030 Uiso 1 1 calc R . . C5 C 0.3366(8) 0.8677(3) 0.8569(3) 0.0207(10) Uani 1 1 d . . . H5 H 0.1987 0.8326 0.8516 0.025 Uiso 1 1 calc R . . C6 C 0.5456(8) 0.7775(2) 1.0040(3) 0.0153(9) Uani 1 1 d . . . H6A H 0.3771 0.7562 0.9991 0.018 Uiso 1 1 calc R . . H6B H 0.5946 0.7964 1.0755 0.018 Uiso 1 1 calc R . . C7 C 0.7188(7) 0.7043(2) 0.9827(3) 0.0105(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.0119(3) 0.0128(3) 0.0144(3) 0.0018(2) 0.0002(2) -0.0016(2) P1 0.0100(5) 0.0082(5) 0.0094(5) 0.0006(4) 0.0013(4) 0.0012(4) P2 0.0106(5) 0.0097(5) 0.0098(5) 0.0007(4) 0.0018(4) -0.0004(4) N1 0.047(3) 0.0122(19) 0.023(2) 0.0054(16) 0.0120(19) 0.0082(19) O1 0.0130(14) 0.0150(15) 0.0122(14) 0.0009(11) 0.0019(11) -0.0005(11) O2 0.0162(15) 0.0135(15) 0.0132(14) -0.0047(12) 0.0008(11) 0.0013(13) O3 0.0120(14) 0.0079(13) 0.0177(14) 0.0002(11) 0.0035(11) 0.0017(11) O4 0.0140(14) 0.0129(14) 0.0123(14) -0.0009(11) 0.0024(11) -0.0026(11) O5 0.0133(14) 0.0216(16) 0.0138(14) -0.0011(12) 0.0039(11) 0.0057(12) O6 0.0207(15) 0.0153(15) 0.0117(14) 0.0044(11) 0.0017(11) -0.0020(12) O7 0.0104(14) 0.0257(17) 0.0139(14) -0.0039(13) 0.0001(11) -0.0065(13) O8 0.0220(18) 0.037(2) 0.0185(18) -0.0061(15) 0.0007(13) -0.0039(16) C1 0.022(2) 0.012(2) 0.014(2) -0.0007(16) 0.0067(16) 0.0042(18) C2 0.026(2) 0.019(2) 0.026(2) 0.0013(19) -0.0019(19) -0.0008(19) C3 0.034(3) 0.017(2) 0.033(3) 0.002(2) 0.009(2) -0.007(2) C4 0.031(3) 0.023(2) 0.021(2) -0.0003(19) 0.0030(19) 0.015(2) C5 0.017(2) 0.022(2) 0.024(2) -0.0008(18) 0.0054(18) 0.0067(19) C6 0.019(2) 0.011(2) 0.017(2) 0.0009(16) 0.0067(17) 0.0002(17) C7 0.0114(19) 0.0092(19) 0.0115(19) 0.0006(15) 0.0042(15) -0.0015(16) _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 Co1 O1 1.996(3) . ? Co1 O5 2.008(3) 1_455 ? Co1 O3 2.058(3) 3_667 ? Co1 O4 2.131(3) . ? Co1 O3 2.228(3) 1_455 ? P1 O1 1.506(3) . ? P1 O3 1.527(3) . ? P1 O2 1.550(3) . ? P1 C7 1.844(4) . ? P2 O5 1.530(3) . ? P2 O4 1.528(3) . ? P2 O6 1.511(3) . ? P2 C7 1.848(4) . ? N1 C4 1.338(6) . ? N1 C3 1.331(6) . ? N1 H1A 0.85(4) . ? O2 H2A 0.81(4) . ? O3 Co1 2.058(3) 3_667 ? O3 Co1 2.228(3) 1_655 ? O5 Co1 2.008(3) 1_655 ? O7 C7 1.438(4) . ? O7 H7A 0.86(5) . ? O8 H8A 0.76(5) . ? O8 H8B 0.85(5) . ? C1 C2 1.390(6) . ? C1 C5 1.397(6) . ? C1 C6 1.509(5) . ? C2 C3 1.379(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.365(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.550(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O5 155.01(12) . 1_455 ? O1 Co1 O3 103.15(11) . 3_667 ? O5 Co1 O3 101.79(11) 1_455 3_667 ? O1 Co1 O4 87.73(11) . . ? O5 Co1 O4 89.81(11) 1_455 . ? O3 Co1 O4 99.54(10) 3_667 . ? O1 Co1 O3 93.15(10) . 1_455 ? O5 Co1 O3 89.87(10) 1_455 1_455 ? O3 Co1 O3 79.13(11) 3_667 1_455 ? O4 Co1 O3 178.54(10) . 1_455 ? O1 P1 O3 116.79(16) . . ? O1 P1 O2 111.84(16) . . ? O3 P1 O2 106.05(15) . . ? O1 P1 C7 109.63(17) . . ? O3 P1 C7 105.44(16) . . ? O2 P1 C7 106.42(17) . . ? O5 P2 O4 112.27(16) . . ? O5 P2 O6 111.98(16) . . ? O4 P2 O6 110.51(16) . . ? O5 P2 C7 104.80(17) . . ? O4 P2 C7 106.16(16) . . ? O6 P2 C7 110.84(17) . . ? C4 N1 C3 122.1(4) . . ? C4 N1 H1A 119(4) . . ? C3 N1 H1A 119(4) . . ? P1 O1 Co1 130.63(16) . . ? P1 O2 H2A 120(3) . . ? P1 O3 Co1 135.13(16) . 3_667 ? P1 O3 Co1 120.30(15) . 1_655 ? Co1 O3 Co1 100.87(11) 3_667 1_655 ? P2 O4 Co1 137.44(16) . . ? P2 O5 Co1 124.27(16) . 1_655 ? C7 O7 H7A 104(3) . . ? H8A O8 H8B 104(5) . . ? C2 C1 C5 118.4(4) . . ? C2 C1 C6 121.4(4) . . ? C5 C1 C6 120.2(4) . . ? C3 C2 C1 119.4(4) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? N1 C3 C2 120.2(4) . . ? N1 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? N1 C4 C5 120.1(4) . . ? N1 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C1 119.8(4) . . ? C4 C5 H5 120.1 . . ? C1 C5 H5 120.1 . . ? C1 C6 C7 116.2(3) . . ? C1 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? C1 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.4 . . ? O7 C7 C6 112.7(3) . . ? O7 C7 P1 107.9(2) . . ? C6 C7 P1 108.1(3) . . ? O7 C7 P2 105.2(2) . . ? C6 C7 P2 115.0(3) . . ? P1 C7 P2 107.55(19) . . ? 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 H1A O4 0.85(4) 1.86(2) 2.702(5) 170(5) 2_656 O2 H2A O6 0.81(4) 1.72(2) 2.533(4) 176(5) 4_576 O7 H7A O8 0.86(5) 1.87(5) 2.705(4) 164(4) 1_656 O8 H8A O6 0.76(5) 2.09(5) 2.843(4) 176(6) 4_575 O8 H8A O4 0.76(5) 2.60(5) 3.036(4) 119(5) 4_575 O8 H8B O5 0.85(5) 2.06(6) 2.882(4) 165(5) 4_475 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.483 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.117 _database_code_depnum_ccdc_archive 'CCDC 860651' ####################################################################### # # 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_co_2 #TrackingRef 'co-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 Co N O10 P2, H2 O' _chemical_formula_sum 'C8 H14 Co N O11 P2' _chemical_formula_weight 421.07 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' Co Co 0.3494 0.9721 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2146(14) _cell_length_b 9.3580(19) _cell_length_c 11.945(2) _cell_angle_alpha 93.03(3) _cell_angle_beta 107.48(3) _cell_angle_gamma 110.72(3) _cell_volume 707.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.975 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 1.499 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.639 _exptl_absorpt_correction_T_max 0.738 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6120 _diffrn_reflns_av_R_equivalents 0.0711 _diffrn_reflns_av_sigmaI/netI 0.0897 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2495 _reflns_number_gt 1784 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0696P)^2^+1.5500P] 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 2495 _refine_ls_number_parameters 230 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1566 _refine_ls_wR_factor_gt 0.1287 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.073 _refine_ls_shift/su_mean 0.003 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 Co1 Co 0.10495(14) 0.27295(10) -0.04085(8) 0.0173(3) Uani 1 1 d . . . P1 P 0.2224(3) 0.0763(2) 0.17913(15) 0.0165(4) Uani 1 1 d . . . P2 P -0.1344(3) 0.1928(2) 0.15694(15) 0.0180(4) Uani 1 1 d . . . O1 O 0.2358(7) 0.1331(5) 0.0641(4) 0.0187(10) Uani 1 1 d . . . O2 O 0.0932(7) -0.0912(5) 0.1711(4) 0.0229(11) Uani 1 1 d . . . O3 O 0.4480(7) 0.1121(6) 0.2692(4) 0.0235(11) Uani 1 1 d . . . H3A H 0.556(11) 0.161(8) 0.252(6) 0.028 Uiso 1 1 d . . . O4 O -0.0865(7) 0.2736(5) 0.0562(4) 0.0200(10) Uani 1 1 d . . . O5 O -0.2912(7) 0.0192(5) 0.1126(4) 0.0227(11) Uani 1 1 d D . . H5A H -0.277(11) -0.023(8) 0.057(4) 0.027 Uiso 1 1 d D . . O6 O -0.2200(7) 0.2705(5) 0.2304(4) 0.0216(11) Uani 1 1 d . . . O7 O 0.2676(8) 0.3530(5) 0.2909(4) 0.0275(12) Uani 1 1 d . . . H7 H 0.2915 0.3864 0.2324 0.041 Uiso 1 1 calc R . . O8 O 0.3366(7) 0.4713(5) 0.0851(4) 0.0227(11) Uani 1 1 d . . . O9 O 0.6532(7) 0.6567(5) 0.1172(4) 0.0242(11) Uani 1 1 d . . . O10 O -0.0323(8) 0.4154(6) -0.1452(4) 0.0257(11) Uani 1 1 d D . . H1OB H 0.023(12) 0.513(9) -0.110(7) 0.039 Uiso 1 1 d . . . H10A H -0.157(5) 0.370(9) -0.163(7) 0.039 Uiso 1 1 d D . . O1W O 0.4718(11) -0.2108(7) 0.2671(6) 0.0506(16) Uani 1 1 d D . . H1WA H 0.511(16) -0.252(10) 0.221(7) 0.076 Uiso 1 1 d D . . H1WB H 0.437(15) -0.132(8) 0.260(8) 0.076 Uiso 1 1 d D . . N1 N 0.0423(14) 0.4035(11) 0.6383(7) 0.058(2) Uani 1 1 d D . . H1A H 0.034(15) 0.454(10) 0.696(6) 0.069 Uiso 1 1 d D . . C1 C 0.0750(11) 0.2302(8) 0.4619(6) 0.0256(16) Uani 1 1 d . . . C2 C -0.1119(13) 0.1883(10) 0.4853(7) 0.037(2) Uani 1 1 d . . . H2 H -0.2286 0.1007 0.4400 0.044 Uiso 1 1 calc R . . C3 C -0.1233(14) 0.2769(12) 0.5760(8) 0.049(3) Uani 1 1 d . . . H3 H -0.2471 0.2484 0.5938 0.059 Uiso 1 1 calc R . . C4 C 0.2200(15) 0.4479(11) 0.6184(7) 0.048(2) Uani 1 1 d . . . H4 H 0.3315 0.5386 0.6634 0.058 Uiso 1 1 calc R . . C5 C 0.2440(13) 0.3614(9) 0.5308(7) 0.036(2) Uani 1 1 d . . . H5 H 0.3725 0.3911 0.5182 0.044 Uiso 1 1 calc R . . C6 C 0.1007(12) 0.1274(8) 0.3679(6) 0.0285(17) Uani 1 1 d . . . H6A H 0.2262 0.1072 0.4050 0.034 Uiso 1 1 calc R . . H6B H -0.0188 0.0286 0.3446 0.034 Uiso 1 1 calc R . . C7 C 0.1178(10) 0.1927(8) 0.2549(6) 0.0194(15) Uani 1 1 d . . . C8 C 0.4989(11) 0.5380(8) 0.0588(6) 0.0206(15) 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 Co1 0.0187(5) 0.0153(5) 0.0201(5) 0.0037(4) 0.0107(4) 0.0056(4) P1 0.0175(9) 0.0170(9) 0.0162(9) 0.0018(7) 0.0070(7) 0.0071(7) P2 0.0192(9) 0.0176(9) 0.0205(10) 0.0025(7) 0.0110(8) 0.0075(8) O1 0.022(2) 0.022(2) 0.017(2) 0.005(2) 0.011(2) 0.011(2) O2 0.027(3) 0.017(2) 0.023(3) 0.003(2) 0.010(2) 0.006(2) O3 0.017(3) 0.030(3) 0.025(3) 0.009(2) 0.010(2) 0.009(2) O4 0.020(2) 0.022(2) 0.022(3) 0.006(2) 0.011(2) 0.010(2) O5 0.025(3) 0.016(3) 0.030(3) 0.002(2) 0.017(2) 0.006(2) O6 0.022(2) 0.023(3) 0.026(3) 0.003(2) 0.014(2) 0.011(2) O7 0.031(3) 0.019(3) 0.024(3) -0.001(2) 0.008(2) 0.002(2) O8 0.023(3) 0.020(2) 0.025(3) 0.003(2) 0.016(2) 0.002(2) O9 0.020(3) 0.022(3) 0.025(3) -0.003(2) 0.012(2) 0.000(2) O10 0.034(3) 0.020(3) 0.027(3) 0.006(2) 0.014(3) 0.011(2) O1W 0.058(4) 0.047(4) 0.068(5) 0.021(3) 0.034(4) 0.034(3) N1 0.070(6) 0.097(7) 0.029(4) -0.002(5) 0.016(4) 0.061(6) C1 0.033(4) 0.031(4) 0.020(4) 0.012(3) 0.013(3) 0.016(4) C2 0.035(5) 0.052(5) 0.027(4) 0.005(4) 0.008(4) 0.022(4) C3 0.036(5) 0.090(8) 0.035(5) 0.009(5) 0.020(4) 0.032(5) C4 0.051(6) 0.055(6) 0.031(5) -0.014(4) 0.003(4) 0.024(5) C5 0.043(5) 0.038(5) 0.032(5) 0.003(4) 0.015(4) 0.019(4) C6 0.034(4) 0.024(4) 0.033(4) 0.008(3) 0.013(4) 0.015(3) C7 0.021(4) 0.021(4) 0.019(4) 0.002(3) 0.008(3) 0.010(3) C8 0.029(4) 0.017(4) 0.019(4) 0.005(3) 0.010(3) 0.012(3) _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 Co1 O2 2.005(5) 2 ? Co1 O4 2.054(4) . ? Co1 O8 2.122(5) . ? Co1 O1 2.124(4) . ? Co1 O9 2.125(5) 2_665 ? Co1 O10 2.163(5) . ? P1 O2 1.494(5) . ? P1 O1 1.517(4) . ? P1 O3 1.563(5) . ? P1 C7 1.861(7) . ? P2 O6 1.503(5) . ? P2 O4 1.517(5) . ? P2 O5 1.565(5) . ? P2 C7 1.844(7) . ? O2 Co1 2.005(5) 2 ? O3 H3A 0.84(7) . ? O5 H5A 0.81(6) . ? O7 C7 1.452(8) . ? O7 H7 0.8200 . ? O8 C8 1.259(8) . ? O9 C8 1.240(8) . ? O9 Co1 2.125(5) 2_665 ? O10 H1OB 0.88(8) . ? O10 H10A 0.80(3) . ? O1W H1WA 0.83(11) . ? O1W H1WB 0.86(8) . ? N1 C4 1.300(12) . ? N1 C3 1.325(12) . ? N1 H1A 0.84(8) . ? C1 C5 1.379(10) . ? C1 C2 1.384(10) . ? C1 C6 1.535(10) . ? C2 C3 1.369(12) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.378(11) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.532(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C8 C8 1.547(13) 2_665 ? 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 O2 Co1 O4 99.94(18) 2 . ? O2 Co1 O8 173.59(18) 2 . ? O4 Co1 O8 86.32(17) . . ? O2 Co1 O1 92.48(18) 2 . ? O4 Co1 O1 93.01(17) . . ? O8 Co1 O1 88.55(18) . . ? O2 Co1 O9 95.60(18) 2 2_665 ? O4 Co1 O9 162.86(18) . 2_665 ? O8 Co1 O9 78.01(17) . 2_665 ? O1 Co1 O9 93.49(18) . 2_665 ? O2 Co1 O10 87.79(19) 2 . ? O4 Co1 O10 85.73(18) . . ? O8 Co1 O10 91.32(19) . . ? O1 Co1 O10 178.74(18) . . ? O9 Co1 O10 87.70(19) 2_665 . ? O2 P1 O1 117.8(3) . . ? O2 P1 O3 107.3(3) . . ? O1 P1 O3 110.4(3) . . ? O2 P1 C7 107.6(3) . . ? O1 P1 C7 109.0(3) . . ? O3 P1 C7 104.0(3) . . ? O6 P2 O4 114.5(3) . . ? O6 P2 O5 107.7(3) . . ? O4 P2 O5 112.7(3) . . ? O6 P2 C7 108.4(3) . . ? O4 P2 C7 106.1(3) . . ? O5 P2 C7 107.0(3) . . ? P1 O1 Co1 134.0(3) . . ? P1 O2 Co1 136.7(3) . 2 ? P1 O3 H3A 121(5) . . ? P2 O4 Co1 134.0(3) . . ? P2 O5 H5A 113(5) . . ? C7 O7 H7 109.5 . . ? C8 O8 Co1 114.6(4) . . ? C8 O9 Co1 113.7(4) . 2_665 ? Co1 O10 H1OB 113(5) . . ? Co1 O10 H10A 105(6) . . ? H1OB O10 H10A 118(8) . . ? H1WA O1W H1WB 127(6) . . ? C4 N1 C3 122.7(8) . . ? C4 N1 H1A 119(7) . . ? C3 N1 H1A 118(7) . . ? C5 C1 C2 118.5(7) . . ? C5 C1 C6 120.2(7) . . ? C2 C1 C6 121.1(7) . . ? C3 C2 C1 119.3(8) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? N1 C3 C2 119.9(8) . . ? N1 C3 H3 120.1 . . ? C2 C3 H3 120.0 . . ? N1 C4 C5 120.3(9) . . ? N1 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C1 C5 C4 119.2(8) . . ? C1 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C7 C6 C1 116.2(6) . . ? C7 C6 H6A 108.2 . . ? C1 C6 H6A 108.2 . . ? C7 C6 H6B 108.2 . . ? C1 C6 H6B 108.2 . . ? H6A C6 H6B 107.4 . . ? O7 C7 C6 108.0(5) . . ? O7 C7 P2 107.3(4) . . ? C6 C7 P2 112.7(5) . . ? O7 C7 P1 109.4(4) . . ? C6 C7 P1 106.8(4) . . ? P2 C7 P1 112.5(3) . . ? O9 C8 O8 126.4(6) . . ? O9 C8 C8 118.1(8) . 2_665 ? O8 C8 C8 115.5(7) . 2_665 ? 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 H3A O6 0.84(7) 1.68(8) 2.525(6) 175(7) 1_655 O5 H5A O1 0.81(6) 1.89(6) 2.690(6) 175(7) 2 O7 H7 O8 0.82 2.04 2.854(7) 177.0 . O10 H10A O8 0.80(3) 2.59(8) 2.995(7) 113(7) 2_565 O10 H1OB O4 0.88(8) 1.91(8) 2.774(7) 168(7) 2_565 N1 H1A O10 0.84(8) 2.11(7) 2.799(9) 139(9) 1_556 N1 H1A O6 0.84(8) 2.42(8) 2.988(10) 126(8) 2_566 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.538 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.147 _database_code_depnum_ccdc_archive 'CCDC 860652' ####################################################################### # # 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_cu-1 #TrackingRef 'cu-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H20 Cu N2 O14 P4' _chemical_formula_sum 'C14 H20 Cu N2 O14 P4' _chemical_formula_weight 627.74 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' Cu Cu 0.3201 1.2651 '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/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.7416(15) _cell_length_b 9.2139(18) _cell_length_c 15.336(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.96(3) _cell_angle_gamma 90.00 _cell_volume 1088.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.916 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 1.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7703 _exptl_absorpt_correction_T_max 0.8522 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9815 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2139 _reflns_number_gt 1772 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0444P)^2^+1.5426P] 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 2139 _refine_ls_number_parameters 172 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.0990 _refine_ls_wR_factor_gt 0.0936 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 Cu1 Cu 0.5000 0.5000 0.0000 0.02101(19) Uani 1 2 d S . . P1 P 0.34767(11) 0.79420(10) 0.07787(6) 0.0175(2) Uani 1 1 d . . . P2 P 0.73015(11) 0.74809(10) 0.07185(6) 0.0175(2) Uani 1 1 d . . . O1 O 0.3402(3) 0.6463(3) 0.03415(18) 0.0313(7) Uani 1 1 d . . . O2 O 0.3041(3) 0.9139(3) 0.01307(17) 0.0291(6) Uani 1 1 d . . . O3 O 0.2274(3) 0.7951(3) 0.15333(17) 0.0268(6) Uani 1 1 d D . . H3A H 0.122(3) 0.799(5) 0.140(3) 0.040 Uiso 1 1 d D . . O4 O 0.6968(3) 0.5857(3) 0.06742(17) 0.0262(6) Uani 1 1 d . . . O5 O 0.6839(4) 0.8080(3) -0.02332(17) 0.0292(6) Uani 1 1 d D . . H5A H 0.697(6) 0.897(2) -0.026(3) 0.044 Uiso 1 1 d D . . O6 O 0.9055(3) 0.7919(3) 0.11102(18) 0.0298(7) Uani 1 1 d . . . O7 O 0.5892(3) 0.9810(3) 0.14827(16) 0.0224(6) Uani 1 1 d D . . H7 H 0.591(6) 1.022(4) 0.1010(17) 0.034 Uiso 1 1 d D . . N1 N 1.0545(5) 0.7984(6) 0.3879(2) 0.0496(12) Uani 1 1 d D . . H1A H 1.155(4) 0.800(6) 0.417(3) 0.074 Uiso 1 1 d D . . C1 C 0.7509(5) 0.7737(4) 0.2824(2) 0.0193(8) Uani 1 1 d . . . C2 C 0.8079(5) 0.9061(5) 0.3174(2) 0.0316(9) Uani 1 1 d . . . H2 H 0.7416 0.9890 0.3047 0.038 Uiso 1 1 calc R . . C3 C 0.9594(6) 0.9160(6) 0.3700(3) 0.0451(12) Uani 1 1 d . . . H3 H 0.9963 1.0052 0.3934 0.054 Uiso 1 1 calc R . . C4 C 1.0091(6) 0.6685(6) 0.3555(3) 0.0486(13) Uani 1 1 d . . . H4 H 1.0800 0.5884 0.3690 0.058 Uiso 1 1 calc R . . C5 C 0.8559(5) 0.6535(5) 0.3017(2) 0.0314(9) Uani 1 1 d . . . H5 H 0.8231 0.5631 0.2786 0.038 Uiso 1 1 calc R . . C6 C 0.5774(5) 0.7593(4) 0.2292(2) 0.0221(8) Uani 1 1 d . . . H6A H 0.4902 0.8043 0.2614 0.027 Uiso 1 1 calc R . . H6B H 0.5491 0.6570 0.2234 0.027 Uiso 1 1 calc R . . C7 C 0.5651(4) 0.8270(4) 0.1366(2) 0.0157(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 Cu1 0.0170(3) 0.0181(3) 0.0267(4) -0.0027(3) -0.0033(2) 0.0014(2) P1 0.0101(4) 0.0225(5) 0.0189(5) -0.0024(4) -0.0028(3) 0.0007(3) P2 0.0112(4) 0.0207(5) 0.0203(5) -0.0030(4) -0.0009(3) 0.0012(3) O1 0.0184(14) 0.0283(16) 0.0451(17) -0.0150(13) -0.0058(12) 0.0006(11) O2 0.0227(14) 0.0345(17) 0.0284(14) 0.0070(12) -0.0061(11) 0.0009(12) O3 0.0089(12) 0.0443(18) 0.0269(14) -0.0012(13) 0.0008(10) 0.0009(11) O4 0.0196(14) 0.0211(15) 0.0361(15) -0.0054(12) -0.0055(11) 0.0043(10) O5 0.0334(16) 0.0342(16) 0.0205(14) 0.0015(13) 0.0056(11) 0.0034(13) O6 0.0130(13) 0.0406(17) 0.0353(15) -0.0063(13) 0.0000(11) -0.0039(11) O7 0.0253(14) 0.0185(14) 0.0224(13) -0.0010(11) -0.0026(11) -0.0009(11) N1 0.023(2) 0.093(4) 0.030(2) 0.008(2) -0.0099(16) -0.010(2) C1 0.0177(18) 0.028(2) 0.0119(16) 0.0040(15) -0.0010(13) 0.0025(15) C2 0.037(2) 0.034(2) 0.022(2) 0.0020(18) -0.0045(17) -0.0044(19) C3 0.044(3) 0.056(3) 0.032(2) 0.001(2) -0.010(2) -0.022(2) C4 0.033(3) 0.077(4) 0.035(3) 0.019(3) 0.002(2) 0.026(3) C5 0.034(2) 0.034(2) 0.025(2) 0.0043(18) -0.0020(17) 0.0089(18) C6 0.0172(19) 0.028(2) 0.0206(18) 0.0017(16) -0.0025(14) -0.0027(15) C7 0.0157(17) 0.0162(18) 0.0143(16) -0.0017(14) -0.0031(13) -0.0003(13) _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 Cu1 O4 1.920(2) . ? Cu1 O4 1.920(2) 3_665 ? Cu1 O1 1.938(3) 3_665 ? Cu1 O1 1.938(3) . ? P1 O2 1.500(3) . ? P1 O1 1.517(3) . ? P1 O3 1.559(3) . ? P1 C7 1.850(3) . ? P2 O6 1.482(3) . ? P2 O4 1.519(3) . ? P2 O5 1.567(3) . ? P2 C7 1.847(3) . ? O3 H3A 0.822(19) . ? O5 H5A 0.831(19) . ? O7 C7 1.440(4) . ? O7 H7 0.821(19) . ? N1 C3 1.322(7) . ? N1 C4 1.329(7) . ? N1 H1A 0.85(2) . ? C1 C2 1.386(5) . ? C1 C5 1.388(5) . ? C1 C6 1.503(5) . ? C2 C3 1.356(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.379(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.545(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O4 180.00(14) . 3_665 ? O4 Cu1 O1 86.47(10) . 3_665 ? O4 Cu1 O1 93.53(10) 3_665 3_665 ? O4 Cu1 O1 93.53(10) . . ? O4 Cu1 O1 86.47(10) 3_665 . ? O1 Cu1 O1 180.00(19) 3_665 . ? O2 P1 O1 111.86(16) . . ? O2 P1 O3 112.20(15) . . ? O1 P1 O3 109.54(16) . . ? O2 P1 C7 109.45(15) . . ? O1 P1 C7 110.67(15) . . ? O3 P1 C7 102.77(15) . . ? O6 P2 O4 115.53(15) . . ? O6 P2 O5 113.12(16) . . ? O4 P2 O5 106.50(15) . . ? O6 P2 C7 109.27(15) . . ? O4 P2 C7 106.74(15) . . ? O5 P2 C7 104.97(15) . . ? P1 O1 Cu1 138.41(16) . . ? P1 O3 H3A 118(3) . . ? P2 O4 Cu1 123.44(15) . . ? P2 O5 H5A 112(3) . . ? C7 O7 H7 111(3) . . ? C3 N1 C4 122.7(4) . . ? C3 N1 H1A 124(4) . . ? C4 N1 H1A 113(4) . . ? C2 C1 C5 117.6(4) . . ? C2 C1 C6 121.3(3) . . ? C5 C1 C6 121.1(3) . . ? C3 C2 C1 120.7(4) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? N1 C3 C2 119.8(4) . . ? N1 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? N1 C4 C5 119.4(4) . . ? N1 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C1 119.7(4) . . ? C4 C5 H5 120.1 . . ? C1 C5 H5 120.1 . . ? C1 C6 C7 115.4(3) . . ? C1 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? C1 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? O7 C7 C6 106.8(3) . . ? O7 C7 P2 111.5(2) . . ? C6 C7 P2 110.8(2) . . ? O7 C7 P1 108.7(2) . . ? C6 C7 P1 110.3(2) . . ? P2 C7 P1 108.61(17) . . ? 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 H3A O6 0.822(19) 1.69(2) 2.510(3) 175(5) 1_455 O5 H5A O2 0.831(19) 1.75(2) 2.568(4) 168(5) 3_675 O7 H7 O2 0.821(19) 2.09(2) 2.857(4) 156(4) 3_675 N1 H1A O1 0.85(2) 2.24(3) 3.025(5) 153(5) 4_676 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.588 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 860653' ####################################################################### # # 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_cu-2 #TrackingRef 'cu-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 Cu3 N2 O18 P4' _chemical_formula_sum 'C16 H18 Cu3 N2 O18 P4' _chemical_formula_weight 840.82 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' Cu Cu 0.3201 1.2651 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6015(17) _cell_length_b 8.9334(18) _cell_length_c 9.6326(19) _cell_angle_alpha 109.44(3) _cell_angle_beta 99.01(3) _cell_angle_gamma 110.06(3) _cell_volume 624.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 419 _exptl_absorpt_coefficient_mu 2.883 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.489 _exptl_absorpt_correction_T_max 0.56 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6538 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _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 3.50 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2854 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0453P)^2^+1.1085P] 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 2854 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 H2A H 0.124(7) -0.475(7) 0.640(7) 0.049(19) Uiso 1 1 d . . . C8 C 0.5521(6) 0.2918(6) 0.9735(5) 0.0251(10) Uani 1 1 d . . . H8 H 0.4994 0.2802 1.0488 0.030 Uiso 1 1 calc R . . C7 C 0.6767(6) 0.4524(6) 0.9990(5) 0.0294(11) Uani 1 1 d . . . H7 H 0.7084 0.5491 1.0916 0.035 Uiso 1 1 calc R . . C6 C 0.7131(6) 0.3337(6) 0.7586(6) 0.0339(12) Uani 1 1 d . . . H6 H 0.7680 0.3489 0.6853 0.041 Uiso 1 1 calc R . . C5 C 0.5922(6) 0.1718(6) 0.7308(5) 0.0307(11) Uani 1 1 d . . . H5 H 0.5683 0.0764 0.6396 0.037 Uiso 1 1 calc R . . O9 O 0.5584(4) 0.5129(4) 0.3381(3) 0.0222(7) Uani 1 1 d . . . O4 O -0.0913(4) -0.0162(4) 0.6271(3) 0.0186(6) Uani 1 1 d . . . O1 O -0.1180(4) -0.3854(4) 0.5557(3) 0.0207(6) Uani 1 1 d . . . Cu1 Cu 0.0000 0.0000 1.0000 0.01593(18) Uani 1 2 d S . . Cu2 Cu 0.26198(6) 0.24830(6) 0.51962(6) 0.01796(15) Uani 1 1 d . . . P1 P 0.03431(14) -0.28624(13) 0.70282(12) 0.0162(2) Uani 1 1 d . . . P2 P 0.09728(13) 0.07171(13) 0.72973(12) 0.0150(2) Uani 1 1 d . . . O5 O 0.2073(4) 0.2212(3) 0.6971(3) 0.0198(6) Uani 1 1 d . . . O6 O 0.1140(4) 0.1377(4) 0.9007(3) 0.0201(6) Uani 1 1 d . . . O3 O -0.0094(4) -0.2238(4) 0.8523(3) 0.0223(7) Uani 1 1 d . . . O2 O 0.1304(4) -0.4032(4) 0.7174(4) 0.0235(7) Uani 1 1 d . . . O8 O 0.3936(4) 0.2798(4) 0.3702(3) 0.0235(7) Uani 1 1 d . . . O7 O 0.2123(4) -0.1414(4) 0.5403(3) 0.0228(7) Uani 1 1 d . . . H7A H 0.1564 -0.1103 0.4878 0.034 Uiso 1 1 calc R . . C2 C 0.1895(5) -0.0922(5) 0.6908(4) 0.0161(8) Uani 1 1 d . . . C1 C 0.4853(5) 0.4396(5) 0.4151(5) 0.0189(9) Uani 1 1 d . . . N1 N 0.7517(5) 0.4690(5) 0.8908(5) 0.0293(9) Uani 1 1 d D . . C4 C 0.5051(5) 0.1476(6) 0.8359(5) 0.0206(9) Uani 1 1 d . . . C3 C 0.3685(5) -0.0278(5) 0.8092(5) 0.0217(9) Uani 1 1 d . . . H3A H 0.3504 -0.0218 0.9075 0.026 Uiso 1 1 calc R . . H3B H 0.4134 -0.1150 0.7745 0.026 Uiso 1 1 calc R . . H1A H 0.810(5) 0.572(3) 0.906(5) 0.023(13) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C8 0.028(2) 0.023(2) 0.020(2) 0.0057(19) 0.0055(19) 0.009(2) C7 0.033(3) 0.021(2) 0.024(2) 0.0036(19) 0.003(2) 0.008(2) C6 0.034(3) 0.030(3) 0.030(3) 0.010(2) 0.017(2) 0.004(2) C5 0.031(3) 0.022(2) 0.025(2) 0.0007(19) 0.012(2) 0.002(2) O9 0.0228(16) 0.0217(16) 0.0196(15) 0.0107(13) 0.0094(13) 0.0033(13) O4 0.0178(15) 0.0144(14) 0.0202(15) 0.0051(12) 0.0065(12) 0.0048(12) O1 0.0221(16) 0.0161(15) 0.0189(15) 0.0041(12) 0.0056(13) 0.0060(12) Cu1 0.0220(4) 0.0131(3) 0.0128(4) 0.0057(3) 0.0091(3) 0.0057(3) Cu2 0.0198(3) 0.0145(3) 0.0165(3) 0.0072(2) 0.0079(2) 0.0021(2) P1 0.0200(5) 0.0123(5) 0.0157(5) 0.0053(4) 0.0085(4) 0.0054(4) P2 0.0197(5) 0.0108(5) 0.0133(5) 0.0050(4) 0.0080(4) 0.0039(4) O5 0.0262(16) 0.0114(14) 0.0155(15) 0.0035(12) 0.0093(13) 0.0016(12) O6 0.0280(16) 0.0146(14) 0.0160(15) 0.0059(12) 0.0117(13) 0.0056(12) O3 0.0337(18) 0.0156(15) 0.0202(16) 0.0081(12) 0.0171(14) 0.0089(13) O2 0.0291(18) 0.0198(16) 0.0220(17) 0.0074(14) 0.0070(14) 0.0126(14) O8 0.0246(16) 0.0170(15) 0.0231(16) 0.0062(13) 0.0134(13) 0.0020(13) O7 0.0291(17) 0.0271(17) 0.0177(15) 0.0101(13) 0.0135(14) 0.0144(14) C2 0.021(2) 0.0127(19) 0.0126(19) 0.0043(16) 0.0080(17) 0.0048(16) C1 0.016(2) 0.020(2) 0.022(2) 0.0098(18) 0.0072(18) 0.0076(17) N1 0.030(2) 0.018(2) 0.031(2) 0.0084(18) 0.0068(18) 0.0034(18) C4 0.016(2) 0.019(2) 0.022(2) 0.0071(18) 0.0044(18) 0.0043(17) C3 0.018(2) 0.019(2) 0.024(2) 0.0075(18) 0.0081(18) 0.0043(18) _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 C8 C7 1.377(6) . ? C8 C4 1.384(6) . ? C8 H8 0.9300 . ? C7 N1 1.330(6) . ? C7 H7 0.9300 . ? C6 N1 1.327(6) . ? C6 C5 1.367(6) . ? C6 H6 0.9300 . ? C5 C4 1.381(6) . ? C5 H5 0.9300 . ? O9 C1 1.250(5) . ? O9 Cu2 1.987(3) 2_666 ? O4 P2 1.527(3) . ? O4 Cu2 1.940(3) 2_556 ? O1 P1 1.515(3) . ? O1 Cu2 2.217(3) 2_556 ? Cu1 O6 1.907(3) 2_557 ? Cu1 O6 1.907(3) . ? Cu1 O3 1.997(3) 2_557 ? Cu1 O3 1.997(3) . ? Cu2 O5 1.911(3) . ? Cu2 O4 1.940(3) 2_556 ? Cu2 O9 1.987(3) 2_666 ? Cu2 O8 1.998(3) . ? Cu2 O1 2.217(3) 2_556 ? P1 O3 1.518(3) . ? P1 O2 1.565(3) . ? P1 C2 1.843(4) . ? P2 O5 1.511(3) . ? P2 O6 1.517(3) . ? P2 C2 1.854(4) . ? O2 H2A 0.79(6) . ? O8 C1 1.248(5) . ? O7 C2 1.434(5) . ? O7 H7A 0.8200 . ? C2 C3 1.551(6) . ? C1 C1 1.553(8) 2_666 ? N1 H1A 0.830(19) . ? C4 C3 1.509(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 C8 C4 120.2(4) . . ? C7 C8 H8 119.9 . . ? C4 C8 H8 119.9 . . ? N1 C7 C8 119.8(4) . . ? N1 C7 H7 120.1 . . ? C8 C7 H7 120.1 . . ? N1 C6 C5 119.6(4) . . ? N1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C5 C4 121.0(4) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C1 O9 Cu2 109.2(3) . 2_666 ? P2 O4 Cu2 138.55(18) . 2_556 ? P1 O1 Cu2 120.00(16) . 2_556 ? O6 Cu1 O6 180.000(1) 2_557 . ? O6 Cu1 O3 94.78(12) 2_557 2_557 ? O6 Cu1 O3 85.22(12) . 2_557 ? O6 Cu1 O3 85.22(12) 2_557 . ? O6 Cu1 O3 94.78(12) . . ? O3 Cu1 O3 180.000(1) 2_557 . ? O5 Cu2 O4 95.03(12) . 2_556 ? O5 Cu2 O9 87.64(12) . 2_666 ? O4 Cu2 O9 177.28(11) 2_556 2_666 ? O5 Cu2 O8 160.80(13) . . ? O4 Cu2 O8 93.05(12) 2_556 . ? O9 Cu2 O8 84.24(12) 2_666 . ? O5 Cu2 O1 108.42(12) . 2_556 ? O4 Cu2 O1 94.34(11) 2_556 2_556 ? O9 Cu2 O1 85.32(12) 2_666 2_556 ? O8 Cu2 O1 88.26(12) . 2_556 ? O1 P1 O3 115.95(17) . . ? O1 P1 O2 110.07(17) . . ? O3 P1 O2 106.81(18) . . ? O1 P1 C2 108.40(18) . . ? O3 P1 C2 107.69(17) . . ? O2 P1 C2 107.62(18) . . ? O5 P2 O6 109.34(17) . . ? O5 P2 O4 111.66(17) . . ? O6 P2 O4 112.66(17) . . ? O5 P2 C2 108.00(17) . . ? O6 P2 C2 105.98(18) . . ? O4 P2 C2 108.94(18) . . ? P2 O5 Cu2 135.91(17) . . ? P2 O6 Cu1 125.64(17) . . ? P1 O3 Cu1 137.07(18) . . ? P1 O2 H2A 117(4) . . ? C1 O8 Cu2 108.4(3) . . ? C2 O7 H7A 109.5 . . ? O7 C2 C3 107.1(3) . . ? O7 C2 P1 109.4(3) . . ? C3 C2 P1 108.2(3) . . ? O7 C2 P2 111.9(3) . . ? C3 C2 P2 113.4(3) . . ? P1 C2 P2 106.7(2) . . ? O9 C1 O8 126.7(4) . . ? O9 C1 C1 116.3(4) . 2_666 ? O8 C1 C1 117.0(4) . 2_666 ? C7 N1 C6 122.0(4) . . ? C7 N1 H1A 115(3) . . ? C6 N1 H1A 122(3) . . ? C8 C4 C5 117.2(4) . . ? C8 C4 C3 119.8(4) . . ? C5 C4 C3 123.0(4) . . ? C4 C3 C2 116.1(4) . . ? C4 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3B 108.3 . . ? C2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.041 _refine_diff_density_min -0.557 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 860654' ####################################################################### # # 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_cu-4 #TrackingRef 'cu-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 Cu N O7 P2' _chemical_formula_sum 'C7 H9 Cu N O7 P2' _chemical_formula_weight 344.63 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5056(11) _cell_length_b 9.820(2) _cell_length_c 9.839(2) _cell_angle_alpha 94.13(3) _cell_angle_beta 103.16(3) _cell_angle_gamma 102.49(3) _cell_volume 501.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 346 _exptl_absorpt_coefficient_mu 2.525 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6381 _exptl_absorpt_correction_T_max 0.7723 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4500 _diffrn_reflns_av_R_equivalents 0.0731 _diffrn_reflns_av_sigmaI/netI 0.0955 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1945 _reflns_number_gt 1453 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0527P)^2^+1.5465P] 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 1945 _refine_ls_number_parameters 167 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1027 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.1455 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.121 _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 Cu1 Cu -0.27038(18) 0.43948(10) -0.00896(9) 0.0173(3) Uani 1 1 d . . . P1 P 0.0805(4) 0.5607(2) 0.27673(19) 0.0144(5) Uani 1 1 d . . . P2 P -0.0664(4) 0.7566(2) 0.07254(19) 0.0147(4) Uani 1 1 d . . . O1 O -0.1680(9) 0.4561(5) 0.1976(5) 0.0168(11) Uani 1 1 d . . . O2 O 0.3052(9) 0.5550(5) 0.2118(5) 0.0157(11) Uani 1 1 d . . . O3 O 0.1540(10) 0.5434(5) 0.4321(5) 0.0195(12) Uani 1 1 d . . . O4 O -0.3110(9) 0.6382(5) 0.0109(5) 0.0166(12) Uani 1 1 d . . . O5 O 0.1620(9) 0.7356(5) 0.0179(5) 0.0173(12) Uani 1 1 d . . . O6 O -0.1185(10) 0.9011(5) 0.0545(5) 0.0201(12) Uani 1 1 d D . . H6C H -0.1562 0.9101 -0.0326 0.030 Uiso 1 1 d RD . . O7 O -0.1965(10) 0.7477(6) 0.3206(5) 0.0210(12) Uani 1 1 d . . . H7 H -0.3264 0.6901 0.2757 0.032 Uiso 1 1 calc R . . N1 N 0.4568(15) 1.2614(7) 0.2747(7) 0.0277(17) Uani 1 1 d D . . C1 C 0.3127(14) 0.9897(8) 0.3204(7) 0.0170(16) Uani 1 1 d . . . C2 C 0.2094(15) 1.0943(8) 0.3740(8) 0.0222(18) Uani 1 1 d . . . H2 H 0.0877 1.0710 0.4257 0.027 Uiso 1 1 calc R . . C3 C 0.2862(17) 1.2279(8) 0.3508(8) 0.0265(19) Uani 1 1 d . . . H3 H 0.2199 1.2974 0.3880 0.032 Uiso 1 1 calc R . . C4 C 0.5583(17) 1.1670(9) 0.2191(9) 0.030(2) Uani 1 1 d . . . H4 H 0.6756 1.1944 0.1658 0.036 Uiso 1 1 calc R . . C5 C 0.4905(16) 1.0309(9) 0.2404(8) 0.0252(19) Uani 1 1 d . . . H5 H 0.5619 0.9646 0.2020 0.030 Uiso 1 1 calc R . . C6 C 0.2539(14) 0.8423(7) 0.3544(7) 0.0166(17) Uani 1 1 d . . . H6A H 0.2360 0.8461 0.4504 0.020 Uiso 1 1 calc R . . H6B H 0.4023 0.8046 0.3527 0.020 Uiso 1 1 calc R . . C7 C 0.0156(13) 0.7364(7) 0.2612(7) 0.0130(16) Uani 1 1 d . . . H1A H 0.502(14) 1.346(3) 0.260(8) 0.020 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0183(5) 0.0194(5) 0.0149(5) 0.0011(4) 0.0053(4) 0.0053(4) P1 0.0169(11) 0.0145(10) 0.0131(9) 0.0024(8) 0.0061(8) 0.0039(9) P2 0.0168(11) 0.0162(10) 0.0121(9) 0.0018(8) 0.0047(8) 0.0048(9) O1 0.017(3) 0.018(3) 0.014(3) 0.003(2) 0.005(2) -0.001(2) O2 0.016(3) 0.020(3) 0.014(3) 0.003(2) 0.008(2) 0.008(2) O3 0.019(3) 0.027(3) 0.015(3) 0.004(2) 0.007(2) 0.007(2) O4 0.014(3) 0.022(3) 0.013(3) 0.001(2) 0.003(2) 0.002(2) O5 0.016(3) 0.019(3) 0.021(3) 0.004(2) 0.010(2) 0.004(2) O6 0.022(3) 0.024(3) 0.019(3) 0.004(2) 0.006(2) 0.012(3) O7 0.018(3) 0.025(3) 0.022(3) -0.003(2) 0.011(2) 0.007(3) N1 0.046(5) 0.011(4) 0.023(4) 0.008(3) 0.007(3) 0.000(4) C1 0.011(4) 0.019(4) 0.015(4) -0.002(3) -0.001(3) -0.002(3) C2 0.026(5) 0.019(4) 0.021(4) 0.001(3) 0.006(4) 0.005(4) C3 0.038(5) 0.021(5) 0.026(4) 0.008(4) 0.015(4) 0.013(4) C4 0.031(5) 0.032(5) 0.026(4) 0.007(4) 0.013(4) -0.003(4) C5 0.029(5) 0.029(5) 0.020(4) 0.008(4) 0.009(4) 0.007(4) C6 0.017(4) 0.012(4) 0.015(4) -0.004(3) 0.000(3) -0.002(3) C7 0.012(4) 0.016(4) 0.013(4) 0.008(3) 0.007(3) 0.003(3) _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 Cu1 O5 1.941(5) 2_565 ? Cu1 O1 1.966(5) . ? Cu1 O2 1.967(5) 2_565 ? Cu1 O4 2.013(5) . ? Cu1 O4 2.261(5) 2_465 ? Cu1 Cu1 2.917(2) 2_565 ? Cu1 Cu1 3.051(2) 2_465 ? P1 O3 1.521(5) . ? P1 O1 1.525(5) . ? P1 O2 1.526(5) . ? P1 C7 1.846(7) . ? P2 O6 1.522(5) . ? P2 O5 1.522(5) . ? P2 O4 1.543(5) . ? P2 C7 1.844(7) . ? O2 Cu1 1.967(5) 2_565 ? O4 Cu1 2.261(5) 2_465 ? O5 Cu1 1.941(5) 2_565 ? O6 H6C 0.8500 . ? O7 C7 1.440(8) . ? O7 H7 0.8200 . ? N1 C4 1.327(11) . ? N1 C3 1.331(10) . ? N1 H1A 0.85(2) . ? C1 C5 1.403(10) . ? C1 C2 1.403(10) . ? C1 C6 1.493(10) . ? C2 C3 1.342(11) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.353(11) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.539(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O1 89.2(2) 2_565 . ? O5 Cu1 O2 91.4(2) 2_565 2_565 ? O1 Cu1 O2 168.9(2) . 2_565 ? O5 Cu1 O4 169.1(2) 2_565 . ? O1 Cu1 O4 87.8(2) . . ? O2 Cu1 O4 89.6(2) 2_565 . ? O5 Cu1 O4 101.45(19) 2_565 2_465 ? O1 Cu1 O4 91.39(19) . 2_465 ? O2 Cu1 O4 99.36(19) 2_565 2_465 ? O4 Cu1 O4 89.08(19) . 2_465 ? O5 Cu1 Cu1 82.52(15) 2_565 2_565 ? O1 Cu1 Cu1 85.95(15) . 2_565 ? O2 Cu1 Cu1 83.13(15) 2_565 2_565 ? O4 Cu1 Cu1 86.83(15) . 2_565 ? O4 Cu1 Cu1 175.21(14) 2_465 2_565 ? O5 Cu1 Cu1 142.65(15) 2_565 2_465 ? O1 Cu1 Cu1 89.59(15) . 2_465 ? O2 Cu1 Cu1 96.64(15) 2_565 2_465 ? O4 Cu1 Cu1 47.81(14) . 2_465 ? O4 Cu1 Cu1 41.27(13) 2_465 2_465 ? Cu1 Cu1 Cu1 134.59(7) 2_565 2_465 ? O3 P1 O1 112.3(3) . . ? O3 P1 O2 109.9(3) . . ? O1 P1 O2 113.0(3) . . ? O3 P1 C7 108.4(3) . . ? O1 P1 C7 105.6(3) . . ? O2 P1 C7 107.3(3) . . ? O6 P2 O5 112.6(3) . . ? O6 P2 O4 111.5(3) . . ? O5 P2 O4 113.0(3) . . ? O6 P2 C7 109.7(3) . . ? O5 P2 C7 106.0(3) . . ? O4 P2 C7 103.6(3) . . ? P1 O1 Cu1 119.1(3) . . ? P1 O2 Cu1 121.0(3) . 2_565 ? P2 O4 Cu1 117.7(3) . . ? P2 O4 Cu1 144.5(3) . 2_465 ? Cu1 O4 Cu1 90.92(19) . 2_465 ? P2 O5 Cu1 124.6(3) . 2_565 ? P2 O6 H6C 109.5 . . ? C7 O7 H7 109.5 . . ? C4 N1 C3 122.7(7) . . ? C4 N1 H1A 118(5) . . ? C3 N1 H1A 119(5) . . ? C5 C1 C2 117.2(7) . . ? C5 C1 C6 120.3(7) . . ? C2 C1 C6 122.3(7) . . ? C3 C2 C1 120.0(7) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? N1 C3 C2 120.2(8) . . ? N1 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? N1 C4 C5 119.7(8) . . ? N1 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C1 120.1(8) . . ? C4 C5 H5 119.9 . . ? C1 C5 H5 119.9 . . ? C1 C6 C7 118.6(6) . . ? C1 C6 H6A 107.7 . . ? C7 C6 H6A 107.7 . . ? C1 C6 H6B 107.7 . . ? C7 C6 H6B 107.7 . . ? H6A C6 H6B 107.1 . . ? O7 C7 C6 106.6(6) . . ? O7 C7 P2 109.8(5) . . ? C6 C7 P2 116.6(5) . . ? O7 C7 P1 109.8(4) . . ? C6 C7 P1 106.2(5) . . ? P2 C7 P1 107.7(4) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.539 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.162 _database_code_depnum_ccdc_archive 'CCDC 860656' ####################################################################### # # 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_cu-5 #TrackingRef 'cu-5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H15 Cu4 N2 O14 P4' _chemical_formula_sum 'C14 H15 Cu4 N2 O14 P4' _chemical_formula_weight 813.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cu Cu 0.3201 1.2651 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5564(11) _cell_length_b 9.887(2) _cell_length_c 10.489(2) _cell_angle_alpha 71.93(3) _cell_angle_beta 88.77(3) _cell_angle_gamma 78.80(3) _cell_volume 536.92(19) _cell_formula_units_Z 1 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.515 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 401 _exptl_absorpt_coefficient_mu 4.288 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.600 _exptl_absorpt_correction_T_max 0.647 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5447 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0966 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2431 _reflns_number_gt 1707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0439P)^2^+1.9688P] 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 2431 _refine_ls_number_parameters 176 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1042 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1189 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.046 _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 Cu1 Cu 0.37547(17) 0.36653(9) 0.71686(10) 0.0265(3) Uani 1 1 d . . . Cu2 Cu 1.0000 0.5000 0.5000 0.0216(3) Uani 1 2 d S . . Cu3 Cu 0.5000 1.0000 0.5000 0.0255(3) Uani 1 2 d S . . P1 P 0.5122(3) 0.67885(18) 0.58415(17) 0.0141(4) Uani 1 1 d . . . P2 P 0.8282(3) 0.45158(18) 0.80562(17) 0.0134(4) Uani 1 1 d . . . O1 O 0.3737(9) 0.8325(5) 0.5302(5) 0.0202(11) Uani 1 1 d . . . O2 O 0.3297(8) 0.5766(5) 0.6187(5) 0.0197(11) Uani 1 1 d . . . O3 O 0.7030(9) 0.6428(5) 0.4850(4) 0.0192(11) Uani 1 1 d . . . O4 O 0.6238(8) 0.3664(5) 0.8405(4) 0.0157(10) Uani 1 1 d . . . O5 O 0.9827(8) 0.4120(5) 0.6938(4) 0.0161(10) Uani 1 1 d . . . O6 O 1.0017(9) 0.4258(5) 0.9255(5) 0.0227(11) Uani 1 1 d D . . H6C H 1.0005 0.4773 0.9772 0.034 Uiso 0.50 1 d PRD . . O7 O 0.8834(10) 0.7291(6) 0.7130(6) 0.0338(14) Uani 1 1 d . . . H7 H 0.9793 0.7005 0.6621 0.051 Uiso 1 1 calc R . . C1 C 0.4806(12) 0.8520(7) 0.8280(7) 0.0155(14) Uani 1 1 d . . . C2 C 0.2639(13) 0.9442(7) 0.7696(7) 0.0195(15) Uani 1 1 d . . . H2 H 0.1377 0.9071 0.7443 0.023 Uiso 1 1 calc R . . C3 C 0.2355(13) 1.0905(7) 0.7492(7) 0.0201(15) Uani 1 1 d . . . H3 H 0.0885 1.1500 0.7090 0.024 Uiso 1 1 calc R . . C4 C 0.6140(13) 1.0613(8) 0.8476(7) 0.0237(16) Uani 1 1 d . . . H4 H 0.7338 1.1002 0.8768 0.028 Uiso 1 1 calc R . . C5 C 0.6532(13) 0.9151(8) 0.8707(7) 0.0230(16) Uani 1 1 d . . . H5 H 0.7974 0.8567 0.9156 0.028 Uiso 1 1 calc R . . C6 C 0.5279(13) 0.6915(7) 0.8480(7) 0.0184(15) Uani 1 1 d . . . H6A H 0.3719 0.6618 0.8464 0.022 Uiso 1 1 calc R . . H6B H 0.6068 0.6403 0.9360 0.022 Uiso 1 1 calc R . . C7 C 0.6907(12) 0.6462(7) 0.7410(7) 0.0149(14) Uani 1 1 d . . . N1 N 0.4058(11) 1.1526(6) 0.7835(6) 0.0188(13) 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 Cu1 0.0286(5) 0.0135(5) 0.0341(6) -0.0013(4) -0.0106(4) -0.0051(4) Cu2 0.0239(7) 0.0184(7) 0.0179(7) -0.0041(5) 0.0048(6) 0.0031(5) Cu3 0.0370(8) 0.0127(6) 0.0260(7) -0.0052(5) 0.0037(6) -0.0051(6) P1 0.0175(9) 0.0103(8) 0.0161(9) -0.0062(7) 0.0044(7) -0.0038(7) P2 0.0170(9) 0.0102(8) 0.0144(9) -0.0063(7) 0.0024(7) -0.0018(7) O1 0.024(3) 0.010(2) 0.022(3) -0.002(2) 0.003(2) 0.000(2) O2 0.019(2) 0.017(3) 0.024(3) -0.007(2) 0.000(2) -0.004(2) O3 0.025(3) 0.019(3) 0.012(2) -0.005(2) 0.003(2) 0.000(2) O4 0.019(2) 0.012(2) 0.015(2) -0.0026(19) 0.003(2) -0.004(2) O5 0.017(2) 0.011(2) 0.017(2) -0.0045(19) 0.003(2) 0.0020(19) O6 0.030(3) 0.016(3) 0.023(3) -0.012(2) -0.011(2) 0.005(2) O7 0.031(3) 0.035(3) 0.042(4) -0.023(3) 0.007(3) -0.006(3) C1 0.019(3) 0.013(3) 0.017(3) -0.010(3) 0.007(3) 0.000(3) C2 0.024(4) 0.017(4) 0.024(4) -0.013(3) 0.008(3) -0.009(3) C3 0.021(4) 0.013(3) 0.027(4) -0.009(3) 0.007(3) -0.001(3) C4 0.022(4) 0.020(4) 0.032(4) -0.013(3) -0.001(3) -0.003(3) C5 0.023(4) 0.016(4) 0.025(4) -0.005(3) 0.000(3) 0.005(3) C6 0.024(4) 0.013(3) 0.017(4) -0.007(3) 0.007(3) 0.001(3) C7 0.017(3) 0.011(3) 0.020(4) -0.008(3) 0.009(3) -0.006(3) N1 0.024(3) 0.010(3) 0.022(3) -0.006(2) 0.002(3) -0.001(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 Cu1 O4 1.913(5) . ? Cu1 O2 1.980(5) . ? Cu1 N1 1.985(6) 1_545 ? Cu1 O5 2.144(5) 1_455 ? Cu1 O3 2.204(5) 2_666 ? Cu1 Cu2 2.9225(15) 1_455 ? Cu2 O3 1.926(5) 2_766 ? Cu2 O3 1.926(5) . ? Cu2 O5 1.956(4) 2_766 ? Cu2 O5 1.956(4) . ? Cu2 Cu1 2.9225(15) 2_666 ? Cu2 Cu1 2.9225(15) 1_655 ? Cu3 O1 1.858(5) . ? Cu3 O1 1.858(5) 2_676 ? P1 O1 1.500(5) . ? P1 O2 1.528(5) . ? P1 O3 1.539(5) . ? P1 C7 1.847(7) . ? P2 O4 1.515(5) . ? P2 O6 1.528(5) . ? P2 O5 1.541(5) . ? P2 C7 1.840(7) . ? O3 Cu1 2.204(5) 2_666 ? O5 Cu1 2.144(5) 1_655 ? O6 H6C 0.8500 . ? O7 C7 1.444(8) . ? O7 H7 0.8200 . ? C1 C2 1.384(10) . ? C1 C5 1.391(10) . ? C1 C6 1.505(9) . ? C2 C3 1.373(9) . ? C2 H2 0.9300 . ? C3 N1 1.334(9) . ? C3 H3 0.9300 . ? C4 N1 1.363(9) . ? C4 C5 1.364(10) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.546(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N1 Cu1 1.985(6) 1_565 ? 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 O4 Cu1 O2 95.05(19) . . ? O4 Cu1 N1 93.8(2) . 1_545 ? O2 Cu1 N1 169.6(2) . 1_545 ? O4 Cu1 O5 138.90(19) . 1_455 ? O2 Cu1 O5 82.06(18) . 1_455 ? N1 Cu1 O5 94.8(2) 1_545 1_455 ? O4 Cu1 O3 145.68(19) . 2_666 ? O2 Cu1 O3 81.91(19) . 2_666 ? N1 Cu1 O3 87.7(2) 1_545 2_666 ? O5 Cu1 O3 74.84(17) 1_455 2_666 ? O4 Cu1 Cu2 155.05(14) . 1_455 ? O2 Cu1 Cu2 60.16(14) . 1_455 ? N1 Cu1 Cu2 111.16(17) 1_545 1_455 ? O5 Cu1 Cu2 42.01(12) 1_455 1_455 ? O3 Cu1 Cu2 41.22(12) 2_666 1_455 ? O3 Cu2 O3 180.000(1) 2_766 . ? O3 Cu2 O5 94.20(19) 2_766 2_766 ? O3 Cu2 O5 85.80(19) . 2_766 ? O3 Cu2 O5 85.80(19) 2_766 . ? O3 Cu2 O5 94.20(19) . . ? O5 Cu2 O5 180.000(1) 2_766 . ? O3 Cu2 Cu1 131.05(14) 2_766 2_666 ? O3 Cu2 Cu1 48.95(14) . 2_666 ? O5 Cu2 Cu1 47.20(13) 2_766 2_666 ? O5 Cu2 Cu1 132.80(13) . 2_666 ? O3 Cu2 Cu1 48.95(14) 2_766 1_655 ? O3 Cu2 Cu1 131.05(14) . 1_655 ? O5 Cu2 Cu1 132.80(13) 2_766 1_655 ? O5 Cu2 Cu1 47.20(13) . 1_655 ? Cu1 Cu2 Cu1 180.0 2_666 1_655 ? O1 Cu3 O1 180.0(3) . 2_676 ? O1 P1 O2 109.2(3) . . ? O1 P1 O3 111.0(3) . . ? O2 P1 O3 112.8(3) . . ? O1 P1 C7 112.3(3) . . ? O2 P1 C7 106.3(3) . . ? O3 P1 C7 105.1(3) . . ? O4 P2 O6 113.0(3) . . ? O4 P2 O5 110.8(3) . . ? O6 P2 O5 107.9(3) . . ? O4 P2 C7 108.7(3) . . ? O6 P2 C7 108.9(3) . . ? O5 P2 C7 107.3(3) . . ? P1 O1 Cu3 126.9(3) . . ? P1 O2 Cu1 131.3(3) . . ? P1 O3 Cu2 134.8(3) . . ? P1 O3 Cu1 126.3(3) . 2_666 ? Cu2 O3 Cu1 89.83(18) . 2_666 ? P2 O4 Cu1 125.4(3) . . ? P2 O5 Cu2 135.6(3) . . ? P2 O5 Cu1 119.1(3) . 1_655 ? Cu2 O5 Cu1 90.79(18) . 1_655 ? P2 O6 H6C 128.5 . . ? C7 O7 H7 109.5 . . ? C2 C1 C5 116.3(6) . . ? C2 C1 C6 122.6(6) . . ? C5 C1 C6 121.1(6) . . ? C3 C2 C1 119.9(6) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? N1 C3 C2 124.0(7) . . ? N1 C3 H3 118.0 . . ? C2 C3 H3 118.0 . . ? N1 C4 C5 122.4(7) . . ? N1 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C1 120.9(7) . . ? C4 C5 H5 119.5 . . ? C1 C5 H5 119.5 . . ? C1 C6 C7 113.6(5) . . ? C1 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C1 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? O7 C7 C6 108.4(5) . . ? O7 C7 P2 109.3(5) . . ? C6 C7 P2 109.7(4) . . ? O7 C7 P1 109.4(4) . . ? C6 C7 P1 111.7(5) . . ? P2 C7 P1 108.3(3) . . ? C3 N1 C4 116.3(6) . . ? C3 N1 Cu1 120.5(5) . 1_565 ? C4 N1 Cu1 122.5(5) . 1_565 ? 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 O7 H7 O2 0.82 2.21 2.961(7) 152.6 1_655 O6 H6C O6 0.85 1.60 2.450(9) 180.0 2_767 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.846 _refine_diff_density_min -0.741 _refine_diff_density_rms 0.170 _database_code_depnum_ccdc_archive 'CCDC 860657' ####################################################################### # # 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_mn #TrackingRef 'mn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 Mn N O7 P2, H2 O' _chemical_formula_sum 'C7 H11 Mn N O8 P2' _chemical_formula_weight 354.05 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 monoclinic _symmetry_space_group_name_H-M ' P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.5529(11) _cell_length_b 16.196(3) _cell_length_c 12.860(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.23(3) _cell_angle_gamma 90.00 _cell_volume 1144.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.054 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 716 _exptl_absorpt_coefficient_mu 1.470 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7101 _exptl_absorpt_correction_T_max 0.742 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11663 _diffrn_reflns_av_R_equivalents 0.0862 _diffrn_reflns_av_sigmaI/netI 0.0715 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2617 _reflns_number_gt 2001 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material 'Bruker SHELXTL/PC and PLATON (Spek, 2003)' _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^)+(0.0236P)^2^+3.3928P] 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 2617 _refine_ls_number_parameters 187 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0890 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.0989 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.081 _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 0.16189(11) 0.57827(4) 0.95124(5) 0.01335(17) Uani 1 1 d . . . P1 P 0.69905(19) 0.62319(6) 1.08015(8) 0.0095(2) Uani 1 1 d . . . P2 P 0.65312(19) 0.65858(6) 0.84735(8) 0.0099(2) Uani 1 1 d . . . N1 N 0.5354(8) 0.9841(2) 0.7995(3) 0.0278(10) Uani 1 1 d D . . H1A H 0.545(10) 1.021(3) 0.754(3) 0.042 Uiso 1 1 d D . . O1 O 0.4358(5) 0.60059(17) 1.0777(2) 0.0148(6) Uani 1 1 d . . . O2 O 0.8122(5) 0.65965(18) 1.1882(2) 0.0155(7) Uani 1 1 d D . . H2A H 0.744(8) 0.695(2) 1.217(3) 0.023 Uiso 1 1 d D . . O3 O 0.8702(5) 0.55379(16) 1.0565(2) 0.0137(6) Uani 1 1 d . . . O4 O 0.4374(5) 0.60025(17) 0.8512(2) 0.0139(6) Uani 1 1 d . . . O5 O 0.8829(5) 0.61202(18) 0.8289(2) 0.0164(7) Uani 1 1 d . . . O6 O 0.5853(5) 0.72605(18) 0.7664(2) 0.0169(7) Uani 1 1 d . . . O7 O 0.9781(5) 0.72810(19) 0.9902(2) 0.0162(7) Uani 1 1 d . . . H7A H 1.014(9) 0.753(3) 1.048(4) 0.024 Uiso 1 1 d . . . O8 O 0.1218(7) 0.8271(2) 0.1578(3) 0.0265(9) Uani 1 1 d . . . H8A H 0.246(10) 0.812(4) 0.191(4) 0.040 Uiso 1 1 d . . . H8B H 0.045(10) 0.839(4) 0.198(4) 0.040 Uiso 1 1 d . . . C1 C 0.5492(8) 0.8511(3) 0.9310(3) 0.0158(9) Uani 1 1 d . . . C2 C 0.7440(9) 0.9065(3) 0.9386(4) 0.0237(11) Uani 1 1 d . . . H2 H 0.8795 0.8990 0.9893 0.028 Uiso 1 1 calc R . . C3 C 0.7331(10) 0.9721(3) 0.8705(4) 0.0292(12) Uani 1 1 d . . . H3 H 0.8638 1.0084 0.8738 0.035 Uiso 1 1 calc R . . C4 C 0.3424(9) 0.9342(3) 0.7914(4) 0.0258(11) Uani 1 1 d . . . H4 H 0.2070 0.9446 0.7417 0.031 Uiso 1 1 calc R . . C5 C 0.3458(8) 0.8673(3) 0.8572(3) 0.0209(10) Uani 1 1 d . . . H5 H 0.2112 0.8326 0.8525 0.025 Uiso 1 1 calc R . . C6 C 0.5557(8) 0.7768(2) 1.0023(3) 0.0136(9) Uani 1 1 d . . . H6A H 0.3912 0.7556 0.9981 0.016 Uiso 1 1 calc R . . H6B H 0.6046 0.7954 1.0739 0.016 Uiso 1 1 calc R . . C7 C 0.7239(7) 0.7044(2) 0.9811(3) 0.0098(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0113(3) 0.0136(3) 0.0150(3) 0.0013(3) 0.0014(3) -0.0010(3) P1 0.0112(5) 0.0088(5) 0.0087(5) 0.0012(4) 0.0024(4) 0.0015(4) P2 0.0104(5) 0.0102(5) 0.0089(5) 0.0002(4) 0.0012(4) -0.0006(4) N1 0.046(3) 0.018(2) 0.021(2) 0.0056(17) 0.010(2) 0.011(2) O1 0.0121(15) 0.0186(16) 0.0134(15) 0.0027(12) 0.0014(12) -0.0039(12) O2 0.0177(17) 0.0169(16) 0.0113(15) -0.0030(12) -0.0002(13) 0.0025(13) O3 0.0148(16) 0.0093(14) 0.0180(15) -0.0001(12) 0.0061(13) 0.0020(12) O4 0.0155(15) 0.0139(15) 0.0126(14) -0.0016(12) 0.0033(12) -0.0043(12) O5 0.0134(16) 0.0199(16) 0.0162(15) -0.0012(13) 0.0033(12) 0.0038(13) O6 0.0215(17) 0.0156(16) 0.0130(15) 0.0058(12) 0.0009(13) -0.0013(13) O7 0.0126(16) 0.0231(18) 0.0131(15) -0.0027(13) 0.0022(13) -0.0060(13) O8 0.022(2) 0.040(2) 0.0169(18) -0.0080(16) -0.0008(14) -0.0045(17) C1 0.022(2) 0.012(2) 0.013(2) -0.0002(17) 0.0009(18) 0.0052(19) C2 0.028(3) 0.019(2) 0.023(2) 0.003(2) -0.001(2) -0.003(2) C3 0.042(3) 0.015(2) 0.032(3) 0.001(2) 0.008(2) -0.008(2) C4 0.032(3) 0.026(3) 0.020(2) 0.000(2) 0.005(2) 0.014(2) C5 0.020(2) 0.019(2) 0.023(2) -0.0025(19) 0.003(2) 0.0030(19) C6 0.017(2) 0.009(2) 0.014(2) -0.0010(17) 0.0024(18) -0.0003(17) C7 0.006(2) 0.012(2) 0.0112(19) 0.0007(16) 0.0023(16) -0.0012(16) _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 2.093(3) . ? Mn1 O5 2.116(3) 1_455 ? Mn1 O3 2.147(3) 3_667 ? Mn1 O4 2.165(3) . ? Mn1 O3 2.289(3) 1_455 ? P1 O1 1.503(3) . ? P1 O3 1.530(3) . ? P1 O2 1.557(3) . ? P1 C7 1.850(4) . ? P2 O6 1.519(3) . ? P2 O5 1.529(3) . ? P2 O4 1.532(3) . ? P2 C7 1.862(4) . ? N1 C4 1.334(7) . ? N1 C3 1.338(7) . ? N1 H1A 0.84(5) . ? O2 H2A 0.81(4) . ? O3 Mn1 2.147(3) 3_667 ? O3 Mn1 2.289(3) 1_655 ? O5 Mn1 2.116(3) 1_655 ? O7 C7 1.451(5) . ? O7 H7A 0.84(5) . ? O8 H8A 0.80(6) . ? O8 H8B 0.74(6) . ? C1 C5 1.392(6) . ? C1 C2 1.398(6) . ? C1 C6 1.510(6) . ? C2 C3 1.373(6) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.374(6) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.548(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Mn1 O5 155.02(12) . 1_455 ? O1 Mn1 O3 104.72(11) . 3_667 ? O5 Mn1 O3 100.13(11) 1_455 3_667 ? O1 Mn1 O4 86.39(11) . . ? O5 Mn1 O4 91.14(11) 1_455 . ? O3 Mn1 O4 101.38(11) 3_667 . ? O1 Mn1 O3 93.86(11) . 1_455 ? O5 Mn1 O3 88.82(11) 1_455 1_455 ? O3 Mn1 O3 78.10(11) 3_667 1_455 ? O4 Mn1 O3 179.46(10) . 1_455 ? O1 P1 O3 116.53(17) . . ? O1 P1 O2 112.21(17) . . ? O3 P1 O2 105.86(16) . . ? O1 P1 C7 109.09(17) . . ? O3 P1 C7 105.99(17) . . ? O2 P1 C7 106.54(18) . . ? O6 P2 O5 112.26(17) . . ? O6 P2 O4 110.31(17) . . ? O5 P2 O4 111.98(17) . . ? O6 P2 C7 110.21(18) . . ? O5 P2 C7 105.62(17) . . ? O4 P2 C7 106.18(17) . . ? C4 N1 C3 122.5(4) . . ? C4 N1 H1A 120(4) . . ? C3 N1 H1A 117(4) . . ? P1 O1 Mn1 130.87(17) . . ? P1 O2 H2A 121(3) . . ? P1 O3 Mn1 133.72(17) . 3_667 ? P1 O3 Mn1 120.16(15) . 1_655 ? Mn1 O3 Mn1 101.90(11) 3_667 1_655 ? P2 O4 Mn1 137.97(17) . . ? P2 O5 Mn1 123.39(17) . 1_655 ? C7 O7 H7A 108(3) . . ? H8A O8 H8B 104(6) . . ? C5 C1 C2 118.1(4) . . ? C5 C1 C6 120.7(4) . . ? C2 C1 C6 121.2(4) . . ? C3 C2 C1 119.3(5) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? N1 C3 C2 120.3(5) . . ? N1 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? N1 C4 C5 119.3(4) . . ? N1 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C4 C5 C1 120.4(5) . . ? C4 C5 H5 119.8 . . ? C1 C5 H5 119.8 . . ? C1 C6 C7 117.4(3) . . ? C1 C6 H6A 108.0 . . ? C7 C6 H6A 108.0 . . ? C1 C6 H6B 108.0 . . ? C7 C6 H6B 108.0 . . ? H6A C6 H6B 107.2 . . ? O7 C7 C6 112.9(3) . . ? O7 C7 P1 107.5(3) . . ? C6 C7 P1 108.1(3) . . ? O7 C7 P2 104.7(2) . . ? C6 C7 P2 114.3(3) . . ? P1 C7 P2 109.0(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O4 0.84(5) 1.87(2) 2.720(5) 178(6) 2_656 O2 H2A O6 0.81(4) 1.72(2) 2.528(4) 175(5) 4_576 O7 H7A O8 0.84(5) 1.88(5) 2.713(5) 167(5) 1_656 O8 H8A O6 0.80(6) 2.08(6) 2.879(5) 175(6) 4_575 O8 H8A O4 0.80(6) 2.60(6) 3.065(4) 119(5) 4_575 O8 H8B O5 0.74(6) 2.17(6) 2.900(5) 169(6) 4_475 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.438 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.117 _database_code_depnum_ccdc_archive 'CCDC 860658'