# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1 #TrackingRef '1-H2O.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N O4 P, H2 O' _chemical_formula_sum 'C10 H12 N O5 P' _chemical_formula_weight 257.18 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2340(12) _cell_length_b 7.9678(13) _cell_length_c 18.530(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.247(3) _cell_angle_gamma 90.00 _cell_volume 1063.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 656 _cell_measurement_theta_min 2.7835 _cell_measurement_theta_max 20.1575 _exptl_crystal_description needlelike _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.978 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5290 _diffrn_reflns_av_R_equivalents 0.0447 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2063 _reflns_number_gt 1603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0989P)^2^+0.9058P] 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 2063 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.1861 _refine_ls_wR_factor_gt 0.1705 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 P1 P 0.84038(14) 0.30066(13) 0.20863(5) 0.0304(3) Uani 1 1 d . . . O1 O 0.9953(4) 0.4159(4) 0.19191(14) 0.0383(7) Uani 1 1 d . . . O2 O 0.8818(4) 0.1185(4) 0.20033(16) 0.0446(8) Uani 1 1 d . . . O3 O 0.7870(4) 0.3342(4) 0.28725(15) 0.0420(8) Uani 1 1 d . . . H3A H 0.7342 0.4250 0.2885 0.050 Uiso 1 1 calc R . . O4 O 0.7611(4) 0.3105(3) -0.14739(14) 0.0423(8) Uani 1 1 d . . . H4C H 0.8747 0.3330 -0.1512 0.051 Uiso 1 1 d R . . N1 N 0.8328(4) 0.6006(4) -0.07568(16) 0.0297(8) Uani 1 1 d . . . H1A H 0.8565 0.5869 -0.1199 0.036 Uiso 1 1 calc R . . C1 C 0.8663(5) 0.7477(5) -0.0451(2) 0.0344(9) Uani 1 1 d . . . H1C H 0.9123 0.8347 -0.0718 0.041 Uiso 1 1 calc R . . C2 C 0.8335(6) 0.7739(5) 0.0268(2) 0.0364(10) Uani 1 1 d . . . H2B H 0.8551 0.8786 0.0480 0.044 Uiso 1 1 calc R . . C3 C 0.7692(5) 0.6445(5) 0.0660(2) 0.0336(9) Uani 1 1 d . . . H3B H 0.7519 0.6606 0.1147 0.040 Uiso 1 1 calc R . . C4 C 0.7290(5) 0.4872(5) 0.03363(19) 0.0268(8) Uani 1 1 d . . . C5 C 0.6644(5) 0.3470(5) 0.0712(2) 0.0295(9) Uani 1 1 d . . . C6 C 0.6384(5) 0.1995(5) 0.0338(2) 0.0351(9) Uani 1 1 d . . . H6A H 0.5985 0.1060 0.0581 0.042 Uiso 1 1 calc R . . C7 C 0.6689(6) 0.1828(5) -0.0392(2) 0.0375(10) Uani 1 1 d . . . H7A H 0.6479 0.0799 -0.0622 0.045 Uiso 1 1 calc R . . C8 C 0.7295(5) 0.3163(5) -0.0774(2) 0.0321(9) Uani 1 1 d . . . C9 C 0.7623(5) 0.4694(5) -0.04030(19) 0.0272(8) Uani 1 1 d . . . C10 C 0.6347(5) 0.3555(5) 0.1505(2) 0.0339(9) Uani 1 1 d . . . H10A H 0.5348 0.2798 0.1602 0.041 Uiso 1 1 calc R . . H10B H 0.5968 0.4684 0.1621 0.041 Uiso 1 1 calc R . . O1W O 0.2561(4) 0.4986(4) 0.30656(16) 0.0513(9) Uani 1 1 d . . . H1WD H 0.1763 0.4731 0.2717 0.062 Uiso 1 1 d R . . H1WA H 0.3369 0.5638 0.2913 0.077 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0334(6) 0.0329(6) 0.0256(5) 0.0063(4) 0.0069(4) 0.0017(4) O1 0.0396(17) 0.0472(17) 0.0285(15) 0.0028(12) 0.0048(12) -0.0071(14) O2 0.0416(17) 0.0418(19) 0.0514(19) 0.0078(14) 0.0091(14) 0.0055(14) O3 0.0502(18) 0.0426(17) 0.0346(16) 0.0118(12) 0.0111(13) 0.0092(14) O4 0.0504(18) 0.0477(19) 0.0298(15) -0.0064(12) 0.0094(13) -0.0084(14) N1 0.0280(17) 0.0341(19) 0.0270(17) 0.0029(13) 0.0032(13) -0.0006(14) C1 0.032(2) 0.030(2) 0.041(2) 0.0032(17) 0.0013(17) 0.0021(17) C2 0.042(2) 0.026(2) 0.041(2) -0.0049(17) 0.0025(19) 0.0016(18) C3 0.032(2) 0.040(2) 0.029(2) -0.0040(17) 0.0052(16) 0.0092(18) C4 0.0215(19) 0.031(2) 0.028(2) 0.0022(15) 0.0021(15) 0.0043(15) C5 0.0218(19) 0.036(2) 0.031(2) 0.0028(16) 0.0034(15) 0.0005(16) C6 0.032(2) 0.033(2) 0.041(2) 0.0086(17) 0.0059(17) -0.0040(17) C7 0.038(2) 0.033(2) 0.042(2) -0.0061(17) 0.0013(18) -0.0043(18) C8 0.031(2) 0.035(2) 0.030(2) -0.0023(16) 0.0030(16) -0.0018(17) C9 0.0243(19) 0.030(2) 0.0274(19) 0.0001(15) 0.0022(15) 0.0033(15) C10 0.033(2) 0.040(2) 0.031(2) 0.0058(17) 0.0097(16) 0.0033(18) O1W 0.058(2) 0.055(2) 0.0395(17) 0.0116(14) -0.0043(15) -0.0186(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 P1 O2 1.493(3) . ? P1 O1 1.503(3) . ? P1 O3 1.564(3) . ? P1 C10 1.809(4) . ? O3 H3A 0.8200 . ? O4 C8 1.339(5) . ? O4 H4C 0.8501 . ? N1 C1 1.314(5) . ? N1 C9 1.358(5) . ? N1 H1A 0.8600 . ? C1 C2 1.391(5) . ? C1 H1C 0.9300 . ? C2 C3 1.367(6) . ? C2 H2B 0.9300 . ? C3 C4 1.409(5) . ? C3 H3B 0.9300 . ? C4 C5 1.419(5) . ? C4 C9 1.420(5) . ? C5 C6 1.369(5) . ? C5 C10 1.506(5) . ? C6 C7 1.397(6) . ? C6 H6A 0.9300 . ? C7 C8 1.371(6) . ? C7 H7A 0.9300 . ? C8 C9 1.410(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? O1W H1WD 0.8500 . ? O1W H1WA 0.8499 . ? 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 P1 O1 114.35(18) . . ? O2 P1 O3 109.32(16) . . ? O1 P1 O3 109.88(16) . . ? O2 P1 C10 109.62(18) . . ? O1 P1 C10 108.56(17) . . ? O3 P1 C10 104.67(17) . . ? P1 O3 H3A 109.5 . . ? C8 O4 H4C 108.9 . . ? C1 N1 C9 122.8(3) . . ? C1 N1 H1A 118.6 . . ? C9 N1 H1A 118.6 . . ? N1 C1 C2 120.4(4) . . ? N1 C1 H1C 119.8 . . ? C2 C1 H1C 119.8 . . ? C3 C2 C1 119.5(4) . . ? C3 C2 H2B 120.2 . . ? C1 C2 H2B 120.2 . . ? C2 C3 C4 120.7(4) . . ? C2 C3 H3B 119.6 . . ? C4 C3 H3B 119.6 . . ? C3 C4 C5 123.8(3) . . ? C3 C4 C9 117.0(3) . . ? C5 C4 C9 119.2(3) . . ? C6 C5 C4 117.6(4) . . ? C6 C5 C10 120.5(3) . . ? C4 C5 C10 121.8(3) . . ? C5 C6 C7 123.1(4) . . ? C5 C6 H6A 118.5 . . ? C7 C6 H6A 118.5 . . ? C8 C7 C6 120.8(4) . . ? C8 C7 H7A 119.6 . . ? C6 C7 H7A 119.6 . . ? O4 C8 C7 124.4(4) . . ? O4 C8 C9 117.8(3) . . ? C7 C8 C9 117.9(4) . . ? N1 C9 C8 119.0(3) . . ? N1 C9 C4 119.6(3) . . ? C8 C9 C4 121.4(3) . . ? C5 C10 P1 112.7(3) . . ? C5 C10 H10A 109.0 . . ? P1 C10 H10A 109.0 . . ? C5 C10 H10B 109.0 . . ? P1 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? H1WD O1W H1WA 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.516 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 935059' ####################################################################### # # 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_l #TrackingRef '1-HCl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H11 N O4 P, H2 O, Cl' _chemical_formula_sum 'C10 H13 Cl N O5 P' _chemical_formula_weight 293.63 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3523(17) _cell_length_b 9.164(2) _cell_length_c 18.612(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.622(4) _cell_angle_gamma 90.00 _cell_volume 1248.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 1950 _cell_measurement_theta_min 2.479 _cell_measurement_theta_max 26.475 _exptl_crystal_description needlelike _exptl_crystal_colour yellow _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.447 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.953 _exptl_absorpt_correction_T_max 0.976 _exptl_absorpt_process_details 'SADABS, Bruker(2000)' _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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6543 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2442 _reflns_number_gt 2099 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.1280P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2442 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1789 _refine_ls_wR_factor_gt 0.1706 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 P1 P 0.23124(9) 0.92643(7) 0.20797(4) 0.0335(3) Uani 1 1 d . . . O1 O 0.1875(3) 1.07927(18) 0.22393(12) 0.0492(6) Uani 1 1 d . . . O1W O 0.3674(3) 0.1724(3) 0.99951(12) 0.0632(7) Uani 1 1 d . . . H1WA H 0.3556 0.0812 0.9922 0.076 Uiso 1 1 d R . . H1WB H 0.4667 0.1888 1.0256 0.076 Uiso 1 1 d R . . O2 O 0.1631(2) 0.82202(19) 0.26389(10) 0.0401(5) Uani 1 1 d . . . H2A H 0.2203 0.7452 0.2639 0.060 Uiso 1 1 calc R . . O3 O 0.4394(3) 0.8929(2) 0.20905(12) 0.0456(5) Uani 1 1 d . . . O4 O 0.0943(3) 0.2659(2) 0.06586(10) 0.0495(5) Uani 1 1 d . . . H4A H 0.1803 0.2355 0.0453 0.074 Uiso 1 1 calc R . . N1 N -0.1649(3) 0.3911(2) 0.13219(12) 0.0373(5) Uani 1 1 d . . . H1B H -0.1631 0.2996 0.1221 0.045 Uiso 1 1 calc R . . C1 C -0.3023(4) 0.4415(3) 0.16543(16) 0.0445(7) Uani 1 1 d . . . H1C H -0.3927 0.3783 0.1782 0.053 Uiso 1 1 calc R . . C2 C -0.3114(4) 0.5884(3) 0.18129(16) 0.0445(7) Uani 1 1 d . . . H2B H -0.4081 0.6247 0.2046 0.053 Uiso 1 1 calc R . . C3 C -0.1768(3) 0.6804(3) 0.16247(14) 0.0387(6) Uani 1 1 d . . . H3B H -0.1836 0.7794 0.1729 0.046 Uiso 1 1 calc R . . C4 C -0.0280(3) 0.6275(3) 0.12753(13) 0.0332(6) Uani 1 1 d . . . C5 C 0.1171(3) 0.7150(3) 0.10637(13) 0.0346(6) Uani 1 1 d . . . C6 C 0.2510(4) 0.6462(3) 0.07265(14) 0.0401(6) Uani 1 1 d . . . H6A H 0.3471 0.7022 0.0588 0.048 Uiso 1 1 calc R . . C7 C 0.2512(4) 0.4964(3) 0.05786(15) 0.0421(7) Uani 1 1 d . . . H7A H 0.3453 0.4558 0.0345 0.050 Uiso 1 1 calc R . . C8 C 0.1141(4) 0.4105(3) 0.07753(14) 0.0365(6) Uani 1 1 d . . . C9 C -0.0251(3) 0.4764(3) 0.11289(12) 0.0329(5) Uani 1 1 d . . . C10 C 0.1245(4) 0.8769(3) 0.12088(14) 0.0408(6) Uani 1 1 d . . . H10A H 0.0008 0.9149 0.1159 0.049 Uiso 1 1 calc R . . H10B H 0.1901 0.9234 0.0844 0.049 Uiso 1 1 calc R . . Cl1 Cl 0.67014(11) 1.07242(7) 0.11850(4) 0.0516(3) Uani 1 1 d . . . H3A H 0.498(6) 0.942(4) 0.185(2) 0.073(13) 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 P1 0.0313(4) 0.0216(4) 0.0481(5) -0.0019(2) 0.0068(3) -0.0012(2) O1 0.0520(13) 0.0230(10) 0.0729(15) -0.0062(9) 0.0071(11) 0.0005(8) O1W 0.0633(15) 0.0548(14) 0.0726(15) -0.0146(11) 0.0117(12) 0.0114(11) O2 0.0426(11) 0.0300(10) 0.0492(11) 0.0027(8) 0.0126(8) 0.0042(7) O3 0.0307(11) 0.0396(11) 0.0669(14) 0.0048(9) 0.0065(9) -0.0018(8) O4 0.0553(13) 0.0357(11) 0.0591(13) -0.0108(9) 0.0132(10) 0.0028(9) N1 0.0386(12) 0.0293(11) 0.0440(12) -0.0040(9) 0.0044(9) -0.0073(9) C1 0.0386(16) 0.0470(17) 0.0491(16) -0.0022(12) 0.0097(12) -0.0096(11) C2 0.0312(15) 0.0485(17) 0.0553(17) -0.0023(13) 0.0117(12) 0.0040(11) C3 0.0358(14) 0.0344(14) 0.0459(14) -0.0042(11) 0.0049(11) 0.0020(10) C4 0.0312(13) 0.0332(13) 0.0346(12) -0.0014(10) -0.0002(10) 0.0000(10) C5 0.0357(14) 0.0315(13) 0.0354(12) 0.0041(10) -0.0027(10) -0.0056(10) C6 0.0372(15) 0.0405(15) 0.0435(14) 0.0008(12) 0.0084(11) -0.0060(11) C7 0.0355(15) 0.0489(18) 0.0434(14) -0.0068(12) 0.0116(11) 0.0030(12) C8 0.0395(15) 0.0334(13) 0.0359(13) -0.0040(10) 0.0002(11) 0.0038(11) C9 0.0313(13) 0.0363(13) 0.0309(12) -0.0017(10) 0.0022(9) -0.0041(10) C10 0.0398(15) 0.0355(15) 0.0463(15) 0.0064(11) 0.0007(11) -0.0031(11) Cl1 0.0480(5) 0.0393(5) 0.0687(6) -0.0029(3) 0.0117(4) -0.0066(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 P1 O1 1.4739(18) . ? P1 O2 1.5336(18) . ? P1 O3 1.559(2) . ? P1 C10 1.789(3) . ? O1W H1WA 0.8500 . ? O1W H1WB 0.8501 . ? O2 H2A 0.8200 . ? O3 H3A 0.79(4) . ? O4 C8 1.348(3) . ? O4 H4A 0.8200 . ? N1 C1 1.318(4) . ? N1 C9 1.367(3) . ? N1 H1B 0.8600 . ? C1 C2 1.381(4) . ? C1 H1C 0.9300 . ? C2 C3 1.372(4) . ? C2 H2B 0.9300 . ? C3 C4 1.412(4) . ? C3 H3B 0.9300 . ? C4 C9 1.411(3) . ? C4 C5 1.420(3) . ? C5 C6 1.371(4) . ? C5 C10 1.508(3) . ? C6 C7 1.400(4) . ? C6 H6A 0.9300 . ? C7 C8 1.357(4) . ? C7 H7A 0.9300 . ? C8 C9 1.407(4) . ? C10 H10A 0.9700 . ? C10 H10B 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 P1 O2 111.33(12) . . ? O1 P1 O3 114.70(12) . . ? O2 P1 O3 104.72(11) . . ? O1 P1 C10 109.80(13) . . ? O2 P1 C10 108.24(12) . . ? O3 P1 C10 107.74(12) . . ? H1WA O1W H1WB 109.5 . . ? P1 O2 H2A 109.5 . . ? P1 O3 H3A 118(3) . . ? C8 O4 H4A 109.5 . . ? C1 N1 C9 123.6(2) . . ? C1 N1 H1B 118.2 . . ? C9 N1 H1B 118.2 . . ? N1 C1 C2 119.8(2) . . ? N1 C1 H1C 120.1 . . ? C2 C1 H1C 120.1 . . ? C3 C2 C1 119.6(2) . . ? C3 C2 H2B 120.2 . . ? C1 C2 H2B 120.2 . . ? C2 C3 C4 121.2(2) . . ? C2 C3 H3B 119.4 . . ? C4 C3 H3B 119.4 . . ? C9 C4 C3 116.9(2) . . ? C9 C4 C5 118.3(2) . . ? C3 C4 C5 124.8(2) . . ? C6 C5 C4 117.4(2) . . ? C6 C5 C10 121.3(2) . . ? C4 C5 C10 121.4(2) . . ? C5 C6 C7 123.7(2) . . ? C5 C6 H6A 118.1 . . ? C7 C6 H6A 118.1 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? O4 C8 C7 126.7(2) . . ? O4 C8 C9 115.2(2) . . ? C7 C8 C9 118.1(2) . . ? N1 C9 C8 118.5(2) . . ? N1 C9 C4 119.0(2) . . ? C8 C9 C4 122.5(2) . . ? C5 C10 P1 114.64(18) . . ? C5 C10 H10A 108.6 . . ? P1 C10 H10A 108.6 . . ? C5 C10 H10B 108.6 . . ? P1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.433 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 935060' ####################################################################### # # 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_8hqmp-zn #TrackingRef '2-Zn.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N O5 P Zn, H2 O' _chemical_formula_sum 'C10 H12 N O6 P Zn' _chemical_formula_weight 338.55 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.4847(16) _cell_length_b 7.8115(8) _cell_length_c 19.2932(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2333.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 3530 _cell_measurement_theta_min 2.4875 _cell_measurement_theta_max 27.9245 _exptl_crystal_description needlelike _exptl_crystal_colour yellow _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.927 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 2.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.850 _exptl_absorpt_correction_T_max 0.893 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11805 _diffrn_reflns_av_R_equivalents 0.0765 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2289 _reflns_number_gt 1681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0558P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2289 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 Zn1 Zn 0.51991(4) 0.19585(7) 0.65625(2) 0.02371(18) Uani 1 1 d . . . P1 P 0.60740(8) 0.04337(15) 0.26060(6) 0.0208(3) Uani 1 1 d . . . O1 O 0.5157(2) -0.0083(4) 0.28313(16) 0.0254(7) Uani 1 1 d . . . O1W O 0.4136(2) 0.3578(5) 0.68255(19) 0.0296(8) Uani 1 1 d . . . H11 H 0.375(3) 0.300(7) 0.704(3) 0.036 Uiso 1 1 d . . . H12 H 0.432(4) 0.439(7) 0.708(3) 0.036 Uiso 1 1 d . . . O2 O 0.60394(19) 0.1394(4) 0.19166(15) 0.0233(7) Uani 1 1 d . . . O2W O 0.7228(3) 0.8040(6) 0.6514(2) 0.0407(10) Uani 1 1 d . . . H21 H 0.709(4) 0.699(9) 0.646(3) 0.049 Uiso 1 1 d . . . H22 H 0.774(4) 0.820(8) 0.637(3) 0.049 Uiso 1 1 d . . . O3 O 0.6682(2) -0.1087(5) 0.25811(17) 0.0309(8) Uani 1 1 d . . . O4 O 0.6245(2) 0.0378(4) 0.60942(16) 0.0275(8) Uani 1 1 d . . . H4A H 0.672(4) 0.061(7) 0.630(3) 0.033 Uiso 1 1 d . . . N1 N 0.5021(2) 0.2255(5) 0.55226(18) 0.0207(8) Uani 1 1 d . . . C1 C 0.4384(3) 0.3105(7) 0.5249(3) 0.0307(11) Uani 1 1 d . . . H1B H 0.3938 0.3477 0.5535 0.037 Uiso 1 1 calc R . . C2 C 0.4341(3) 0.3487(7) 0.4533(2) 0.0314(12) Uani 1 1 d . . . H2B H 0.3872 0.4084 0.4354 0.038 Uiso 1 1 calc R . . C3 C 0.4990(3) 0.2975(6) 0.4108(2) 0.0273(10) Uani 1 1 d . . . H3B H 0.4964 0.3217 0.3636 0.033 Uiso 1 1 calc R . . C4 C 0.5711(3) 0.2068(6) 0.4384(2) 0.0240(10) Uani 1 1 d . . . C5 C 0.6411(3) 0.1479(6) 0.3983(2) 0.0259(10) Uani 1 1 d . . . C6 C 0.7031(3) 0.0504(7) 0.4296(2) 0.0310(11) Uani 1 1 d . . . H6A H 0.7487 0.0093 0.4030 0.037 Uiso 1 1 calc R . . C7 C 0.7004(3) 0.0100(7) 0.5009(3) 0.0305(11) Uani 1 1 d . . . H7A H 0.7436 -0.0574 0.5204 0.037 Uiso 1 1 calc R . . C8 C 0.6350(3) 0.0692(6) 0.5411(2) 0.0207(9) Uani 1 1 d . . . C9 C 0.5696(3) 0.1678(6) 0.5103(2) 0.0215(10) Uani 1 1 d . . . C10 C 0.6499(3) 0.1956(7) 0.3224(2) 0.0313(11) Uani 1 1 d . . . H10A H 0.7107 0.2126 0.3124 0.038 Uiso 1 1 calc R . . H10B H 0.6210 0.3043 0.3151 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0262(3) 0.0278(3) 0.0171(3) 0.0005(2) 0.0016(2) -0.0029(2) P1 0.0193(6) 0.0261(6) 0.0170(5) 0.0020(5) 0.0026(4) -0.0001(5) O1 0.0213(17) 0.0281(17) 0.0269(16) 0.0066(14) 0.0055(14) -0.0011(13) O1W 0.029(2) 0.025(2) 0.0356(19) -0.0009(15) 0.0066(17) -0.0008(15) O2 0.0208(17) 0.0341(18) 0.0151(15) 0.0074(13) 0.0022(12) -0.0006(14) O2W 0.030(2) 0.048(2) 0.044(2) 0.012(2) -0.0064(18) 0.0045(19) O3 0.0267(19) 0.033(2) 0.0333(18) 0.0054(15) 0.0037(15) 0.0038(14) O4 0.031(2) 0.037(2) 0.0148(16) -0.0022(14) -0.0049(14) 0.0000(15) N1 0.0150(19) 0.026(2) 0.0210(18) -0.0009(15) 0.0007(14) -0.0056(15) C1 0.028(3) 0.032(3) 0.032(3) -0.005(2) 0.005(2) 0.003(2) C2 0.035(3) 0.035(3) 0.024(2) -0.005(2) -0.008(2) 0.004(2) C3 0.036(3) 0.024(2) 0.022(2) 0.0033(19) -0.0050(19) -0.0013(19) C4 0.026(3) 0.025(3) 0.021(2) -0.0023(19) -0.0044(18) -0.0121(19) C5 0.027(3) 0.033(3) 0.019(2) -0.0008(19) 0.0043(19) -0.008(2) C6 0.025(3) 0.046(3) 0.022(2) -0.008(2) 0.011(2) -0.004(2) C7 0.022(3) 0.035(3) 0.034(3) 0.001(2) -0.006(2) 0.000(2) C8 0.022(2) 0.024(2) 0.016(2) -0.0025(18) 0.0013(18) -0.0048(19) C9 0.029(3) 0.020(2) 0.0155(19) -0.0029(17) -0.0003(18) -0.0085(19) C10 0.038(3) 0.037(3) 0.019(2) -0.005(2) 0.002(2) -0.013(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 Zn1 O2 1.953(3) 7_566 ? Zn1 O1 1.954(3) 5_656 ? Zn1 N1 2.038(4) . ? Zn1 O1W 2.137(4) . ? Zn1 O4 2.228(3) . ? P1 O3 1.516(4) . ? P1 O2 1.528(3) . ? P1 O1 1.539(3) . ? P1 C10 1.808(5) . ? O1 Zn1 1.954(3) 5_656 ? O1W H11 0.85(6) . ? O1W H12 0.85(6) . ? O2 Zn1 1.953(3) 7_565 ? O2W H21 0.85(7) . ? O2W H22 0.85(6) . ? O4 C8 1.351(5) . ? O4 H4A 0.85(6) . ? N1 C1 1.302(6) . ? N1 C9 1.396(6) . ? C1 C2 1.414(7) . ? C1 H1B 0.9300 . ? C2 C3 1.356(7) . ? C2 H2B 0.9300 . ? C3 C4 1.426(7) . ? C3 H3B 0.9300 . ? C4 C5 1.408(6) . ? C4 C9 1.421(6) . ? C5 C6 1.366(7) . ? C5 C10 1.518(6) . ? C6 C7 1.412(7) . ? C6 H6A 0.9300 . ? C7 C8 1.357(7) . ? C7 H7A 0.9300 . ? C8 C9 1.404(6) . ? C10 H10A 0.9700 . ? C10 H10B 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 O2 Zn1 O1 118.19(13) 7_566 5_656 ? O2 Zn1 N1 111.08(14) 7_566 . ? O1 Zn1 N1 129.50(14) 5_656 . ? O2 Zn1 O1W 92.30(14) 7_566 . ? O1 Zn1 O1W 94.84(14) 5_656 . ? N1 Zn1 O1W 93.58(15) . . ? O2 Zn1 O4 91.29(13) 7_566 . ? O1 Zn1 O4 91.85(13) 5_656 . ? N1 Zn1 O4 76.23(14) . . ? O1W Zn1 O4 169.81(13) . . ? O3 P1 O2 112.27(19) . . ? O3 P1 O1 112.1(2) . . ? O2 P1 O1 110.02(18) . . ? O3 P1 C10 108.1(2) . . ? O2 P1 C10 105.3(2) . . ? O1 P1 C10 108.8(2) . . ? P1 O1 Zn1 128.8(2) . 5_656 ? Zn1 O1W H11 110(4) . . ? Zn1 O1W H12 109(4) . . ? H11 O1W H12 110(5) . . ? P1 O2 Zn1 130.64(18) . 7_565 ? H21 O2W H22 109(6) . . ? C8 O4 Zn1 112.5(3) . . ? C8 O4 H4A 108(4) . . ? Zn1 O4 H4A 109(4) . . ? C1 N1 C9 119.8(4) . . ? C1 N1 Zn1 124.1(3) . . ? C9 N1 Zn1 115.6(3) . . ? N1 C1 C2 122.6(4) . . ? N1 C1 H1B 118.7 . . ? C2 C1 H1B 118.7 . . ? C3 C2 C1 119.6(5) . . ? C3 C2 H2B 120.2 . . ? C1 C2 H2B 120.2 . . ? C2 C3 C4 120.1(4) . . ? C2 C3 H3B 120.0 . . ? C4 C3 H3B 120.0 . . ? C5 C4 C9 118.6(4) . . ? C5 C4 C3 124.1(4) . . ? C9 C4 C3 117.2(4) . . ? C6 C5 C4 118.7(4) . . ? C6 C5 C10 120.0(4) . . ? C4 C5 C10 121.3(4) . . ? C5 C6 C7 122.3(4) . . ? C5 C6 H6A 118.9 . . ? C7 C6 H6A 118.9 . . ? C8 C7 C6 120.1(5) . . ? C8 C7 H7A 119.9 . . ? C6 C7 H7A 119.9 . . ? O4 C8 C7 125.8(4) . . ? O4 C8 C9 115.2(4) . . ? C7 C8 C9 119.0(4) . . ? N1 C9 C8 118.2(4) . . ? N1 C9 C4 120.6(4) . . ? C8 C9 C4 121.2(4) . . ? C5 C10 P1 116.2(3) . . ? C5 C10 H10A 108.2 . . ? P1 C10 H10A 108.2 . . ? C5 C10 H10B 108.2 . . ? P1 C10 H10B 108.2 . . ? H10A C10 H10B 107.4 . . ? 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 O2W H22 O2 0.85(6) 2.18(7) 2.828(5) 133(5) 2_665 O1W H12 O1 0.85(6) 2.02(6) 2.765(5) 146(5) 7_566 O1W H11 O3 0.85(6) 1.80(6) 2.589(5) 154(5) 5_656 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.461 _refine_diff_density_min -0.751 _refine_diff_density_rms 0.114 _database_code_depnum_ccdc_archive 'CCDC 935061' ####################################################################### # # 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_1a #TrackingRef '3-Cu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H14 Cu N O8 P' _chemical_formula_weight 394.75 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 'P2(1)/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 10.8573(10) _cell_length_b 11.5904(11) _cell_length_c 10.9689(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.0800(10) _cell_angle_gamma 90.00 _cell_volume 1372.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4763 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.42 _exptl_crystal_description blocky _exptl_crystal_colour blue _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.753 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.869 _exptl_absorpt_correction_T_max 0.916 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11731 _diffrn_reflns_av_R_equivalents 0.0899 _diffrn_reflns_av_sigmaI/netI 0.0755 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.44 _reflns_number_total 3117 _reflns_number_gt 2698 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0910P)^2^+1.7971P] 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 3117 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.1496 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.31450(3) 0.41276(3) 0.61306(3) 0.01226(17) Uani 1 1 d . . . P1 P 0.39554(7) 0.36620(7) 0.54637(8) 0.0125(2) Uani 1 1 d . . . O1 O 0.5238(2) 0.3439(2) 0.6080(2) 0.0189(5) Uani 1 1 d . . . O1W O 0.4129(3) 0.5962(2) 0.7740(3) 0.0332(7) Uani 1 1 d . . . H1WA H 0.3974 0.5658 0.7036 0.040 Uiso 1 1 d R . . H1WB H 0.3940 0.6674 0.7701 0.040 Uiso 1 1 d R . . O2 O 0.3591(2) 0.4915(2) 0.5297(2) 0.0156(5) Uani 1 1 d . . . O2W O 0.4011(3) 0.0852(2) 0.4389(3) 0.0325(7) Uani 1 1 d . . . H2WA H 0.3894 0.0541 0.3685 0.049 Uiso 1 1 d R . . H2WB H 0.3485 0.0591 0.4840 0.049 Uiso 1 1 d R . . O3 O 0.3742(2) 0.3079(2) 0.4167(2) 0.0212(5) Uani 1 1 d . . . H3A H 0.3826 0.2378 0.4241 0.032 Uiso 1 1 calc R . . O4 O -0.2257(2) 0.27457(19) 0.4964(2) 0.0148(5) Uani 1 1 d . . . O5 O -0.2715(2) 0.1782(2) 0.2656(2) 0.0199(5) Uani 1 1 d . . . O6 O -0.3197(3) 0.0090(2) 0.3443(3) 0.0267(6) Uani 1 1 d . . . N1 N -0.1349(2) 0.4558(2) 0.6250(2) 0.0129(5) Uani 1 1 d . . . C1 C -0.0920(3) 0.5505(3) 0.6820(3) 0.0154(6) Uani 1 1 d . . . H1B H -0.1481 0.6061 0.7022 0.018 Uiso 1 1 calc R . . C2 C 0.0349(3) 0.5702(3) 0.7133(3) 0.0181(7) Uani 1 1 d . . . H2B H 0.0622 0.6390 0.7505 0.022 Uiso 1 1 calc R . . C3 C 0.1181(3) 0.4871(3) 0.6886(3) 0.0163(7) Uani 1 1 d . . . H3B H 0.2021 0.4977 0.7127 0.020 Uiso 1 1 calc R . . C4 C 0.0765(3) 0.3847(3) 0.6264(3) 0.0136(6) Uani 1 1 d . . . C5 C 0.1578(3) 0.2938(3) 0.5972(3) 0.0142(6) Uani 1 1 d . . . C6 C 0.1075(3) 0.2020(3) 0.5292(3) 0.0173(7) Uani 1 1 d . . . H6A H 0.1599 0.1436 0.5078 0.021 Uiso 1 1 calc R . . C7 C -0.0203(3) 0.1930(3) 0.4909(3) 0.0167(7) Uani 1 1 d . . . H7A H -0.0505 0.1308 0.4432 0.020 Uiso 1 1 calc R . . C8 C -0.1000(3) 0.2766(3) 0.5244(3) 0.0136(6) Uani 1 1 d . . . C9 C -0.0525(3) 0.3741(3) 0.5931(3) 0.0122(6) Uani 1 1 d . . . C10 C 0.2937(3) 0.2953(3) 0.6432(3) 0.0153(6) Uani 1 1 d . . . H10A H 0.3212 0.2161 0.6553 0.018 Uiso 1 1 calc R . . H10B H 0.3030 0.3327 0.7227 0.018 Uiso 1 1 calc R . . C11 C -0.2830(3) 0.1632(3) 0.4818(3) 0.0173(7) Uani 1 1 d . . . H11A H -0.3662 0.1689 0.5058 0.021 Uiso 1 1 calc R . . H11B H -0.2373 0.1101 0.5380 0.021 Uiso 1 1 calc R . . C12 C -0.2909(3) 0.1122(3) 0.3546(3) 0.0178(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 0.0087(2) 0.0140(3) 0.0136(3) 0.00123(13) -0.00097(16) -0.00020(13) P1 0.0092(4) 0.0130(4) 0.0149(4) 0.0016(3) -0.0008(3) -0.0001(3) O1 0.0104(11) 0.0205(13) 0.0253(13) 0.0071(10) -0.0010(9) -0.0008(9) O1W 0.0483(19) 0.0231(15) 0.0282(16) -0.0054(12) 0.0042(14) 0.0015(13) O2 0.0136(11) 0.0128(12) 0.0197(12) 0.0024(9) -0.0012(8) 0.0014(9) O2W 0.0461(19) 0.0220(15) 0.0298(17) -0.0003(11) 0.0057(14) 0.0000(12) O3 0.0295(13) 0.0195(13) 0.0141(12) -0.0019(9) 0.0002(10) -0.0005(10) O4 0.0093(10) 0.0150(12) 0.0192(12) -0.0041(9) -0.0022(8) -0.0016(8) O5 0.0163(11) 0.0216(13) 0.0211(13) -0.0044(10) -0.0003(9) 0.0005(9) O6 0.0297(14) 0.0214(14) 0.0290(15) -0.0038(11) 0.0034(11) -0.0028(11) N1 0.0120(12) 0.0146(14) 0.0118(13) 0.0003(10) 0.0002(9) -0.0003(10) C1 0.0180(16) 0.0148(16) 0.0133(15) -0.0024(12) 0.0014(12) 0.0017(12) C2 0.0192(17) 0.0195(17) 0.0152(16) -0.0055(12) 0.0003(13) -0.0045(13) C3 0.0127(14) 0.0217(17) 0.0134(15) -0.0003(13) -0.0027(11) -0.0047(12) C4 0.0109(14) 0.0171(16) 0.0123(15) 0.0019(12) -0.0015(11) -0.0015(12) C5 0.0106(14) 0.0136(16) 0.0182(16) 0.0045(12) 0.0009(11) -0.0011(12) C6 0.0146(15) 0.0132(16) 0.0240(17) 0.0027(13) 0.0023(13) 0.0028(12) C7 0.0141(15) 0.0133(16) 0.0225(17) -0.0007(12) 0.0014(12) -0.0018(12) C8 0.0119(14) 0.0133(16) 0.0151(15) 0.0014(12) 0.0000(11) -0.0012(11) C9 0.0125(14) 0.0129(15) 0.0112(15) 0.0022(11) 0.0015(11) 0.0005(11) C10 0.0117(14) 0.0180(16) 0.0155(15) 0.0043(12) -0.0022(11) 0.0007(12) C11 0.0122(14) 0.0185(17) 0.0207(17) -0.0020(13) -0.0002(12) -0.0052(12) C12 0.0123(15) 0.0210(18) 0.0199(17) -0.0008(13) 0.0003(12) 0.0019(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 O1 1.924(2) 1_455 ? Cu1 O2 1.938(2) 3_566 ? Cu1 O5 1.991(2) 4_566 ? Cu1 N1 2.003(3) . ? Cu1 O4 2.322(2) . ? P1 O1 1.505(2) . ? P1 O2 1.512(2) . ? P1 O3 1.569(3) . ? P1 C10 1.810(3) . ? O1 Cu1 1.924(2) 1_655 ? O1W H1WA 0.8500 . ? O1W H1WB 0.8500 . ? O2 Cu1 1.938(2) 3_566 ? O2W H2WA 0.8501 . ? O2W H2WB 0.8500 . ? O3 H3A 0.8200 . ? O4 C8 1.368(4) . ? O4 C11 1.434(4) . ? O5 C12 1.275(4) . ? O5 Cu1 1.991(2) 4_565 ? O6 C12 1.238(5) . ? N1 C1 1.324(4) . ? N1 C9 1.373(4) . ? C1 C2 1.403(5) . ? C1 H1B 0.9300 . ? C2 C3 1.367(5) . ? C2 H2B 0.9300 . ? C3 C4 1.419(5) . ? C3 H3B 0.9300 . ? C4 C9 1.415(4) . ? C4 C5 1.433(5) . ? C5 C6 1.378(5) . ? C5 C10 1.508(4) . ? C6 C7 1.410(4) . ? C6 H6A 0.9300 . ? C7 C8 1.375(5) . ? C7 H7A 0.9300 . ? C8 C9 1.425(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.509(5) . ? C11 H11A 0.9700 . ? C11 H11B 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 Cu1 O2 93.75(10) 1_455 3_566 ? O1 Cu1 O5 86.35(10) 1_455 4_566 ? O2 Cu1 O5 176.75(10) 3_566 4_566 ? O1 Cu1 N1 169.70(11) 1_455 . ? O2 Cu1 N1 93.92(10) 3_566 . ? O5 Cu1 N1 86.38(10) 4_566 . ? O1 Cu1 O4 97.38(9) 1_455 . ? O2 Cu1 O4 91.84(9) 3_566 . ? O5 Cu1 O4 91.36(9) 4_566 . ? N1 Cu1 O4 75.51(10) . . ? O1 P1 O2 115.96(14) . . ? O1 P1 O3 111.94(14) . . ? O2 P1 O3 107.04(14) . . ? O1 P1 C10 104.61(14) . . ? O2 P1 C10 109.81(14) . . ? O3 P1 C10 107.16(15) . . ? P1 O1 Cu1 137.69(15) . 1_655 ? H1WA O1W H1WB 109.5 . . ? P1 O2 Cu1 133.43(15) . 3_566 ? H2WA O2W H2WB 109.5 . . ? P1 O3 H3A 109.5 . . ? C8 O4 C11 116.8(2) . . ? C8 O4 Cu1 109.09(18) . . ? C11 O4 Cu1 118.83(18) . . ? C12 O5 Cu1 106.4(2) . 4_565 ? C1 N1 C9 119.0(3) . . ? C1 N1 Cu1 121.9(2) . . ? C9 N1 Cu1 117.9(2) . . ? N1 C1 C2 122.6(3) . . ? N1 C1 H1B 118.7 . . ? C2 C1 H1B 118.7 . . ? C3 C2 C1 119.3(3) . . ? C3 C2 H2B 120.3 . . ? C1 C2 H2B 120.3 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3B 120.0 . . ? C4 C3 H3B 120.0 . . ? C9 C4 C3 116.9(3) . . ? C9 C4 C5 119.6(3) . . ? C3 C4 C5 123.4(3) . . ? C6 C5 C4 118.1(3) . . ? C6 C5 C10 120.5(3) . . ? C4 C5 C10 121.4(3) . . ? C5 C6 C7 122.6(3) . . ? C5 C6 H6A 118.7 . . ? C7 C6 H6A 118.7 . . ? C8 C7 C6 119.7(3) . . ? C8 C7 H7A 120.2 . . ? C6 C7 H7A 120.2 . . ? O4 C8 C7 124.7(3) . . ? O4 C8 C9 115.4(3) . . ? C7 C8 C9 119.9(3) . . ? N1 C9 C4 121.9(3) . . ? N1 C9 C8 118.2(3) . . ? C4 C9 C8 119.9(3) . . ? C5 C10 P1 116.5(2) . . ? C5 C10 H10A 108.2 . . ? P1 C10 H10A 108.2 . . ? C5 C10 H10B 108.2 . . ? P1 C10 H10B 108.2 . . ? H10A C10 H10B 107.3 . . ? O4 C11 C12 116.0(3) . . ? O4 C11 H11A 108.3 . . ? C12 C11 H11A 108.3 . . ? O4 C11 H11B 108.3 . . ? C12 C11 H11B 108.3 . . ? H11A C11 H11B 107.4 . . ? O6 C12 O5 124.8(3) . . ? O6 C12 C11 116.9(3) . . ? O5 C12 C11 118.3(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.983 _refine_diff_density_min -1.022 _refine_diff_density_rms 0.256 _database_code_depnum_ccdc_archive 'CCDC 935062' ####################################################################### # # 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_2 #TrackingRef '4-Fe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Fe N O6 P' _chemical_formula_weight 351.03 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' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _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 7.7487(15) _cell_length_b 19.408(4) _cell_length_c 8.3361(17) _cell_angle_alpha 90.00 _cell_angle_beta 99.81(3) _cell_angle_gamma 90.00 _cell_volume 1235.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1160 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 23.06 _exptl_crystal_description needlelike _exptl_crystal_colour brown _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.887 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 1.379 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.876 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Bruker Smart Aepex CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9077 _diffrn_reflns_av_R_equivalents 0.0874 _diffrn_reflns_av_sigmaI/netI 0.0660 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2165 _reflns_number_gt 1541 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2165 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 Fe1 Fe 1.05476(8) 0.67548(3) 0.60917(8) 0.0307(2) Uani 1 1 d . . . P1 P 0.74786(15) 0.30964(6) 0.71614(14) 0.0263(3) Uani 1 1 d . . . O1 O 0.8195(5) 0.33723(18) 0.5752(4) 0.0466(9) Uani 1 1 d . . . O2 O 0.7762(4) 0.23433(15) 0.7523(4) 0.0347(8) Uani 1 1 d . . . O3 O 0.5481(4) 0.32612(16) 0.6821(4) 0.0401(9) Uani 1 1 d . . . H3A H 0.5044 0.3151 0.7613 0.060 Uiso 1 1 calc R . . O4 O 0.8297(4) 0.64235(15) 0.7216(4) 0.0330(8) Uani 1 1 d . . . O5 O 0.8529(4) 0.74203(19) 0.5322(5) 0.0491(11) Uani 1 1 d . . . O6 O 0.6237(4) 0.79759(17) 0.5919(4) 0.0415(9) Uani 1 1 d . . . N1 N 1.0885(4) 0.56753(18) 0.6704(4) 0.0272(9) Uani 1 1 d . . . C1 C 1.2231(6) 0.5311(2) 0.6394(6) 0.0337(11) Uani 1 1 d . . . H1B H 1.3057 0.5525 0.5872 0.040 Uiso 1 1 calc R . . C2 C 1.2459(6) 0.4617(2) 0.6823(6) 0.0361(12) Uani 1 1 d . . . H2B H 1.3435 0.4378 0.6607 0.043 Uiso 1 1 calc R . . C3 C 1.1244(5) 0.4293(2) 0.7558(6) 0.0303(11) Uani 1 1 d . . . H3B H 1.1390 0.3831 0.7848 0.036 Uiso 1 1 calc R . . C4 C 0.9767(5) 0.4656(2) 0.7880(5) 0.0243(10) Uani 1 1 d . . . C5 C 0.8379(6) 0.4355(2) 0.8569(5) 0.0264(10) Uani 1 1 d . . . C6 C 0.6998(6) 0.4767(2) 0.8800(5) 0.0290(11) Uani 1 1 d . . . H6A H 0.6087 0.4573 0.9246 0.035 Uiso 1 1 calc R . . C7 C 0.6915(6) 0.5471(2) 0.8386(6) 0.0342(11) Uani 1 1 d . . . H7A H 0.5973 0.5737 0.8576 0.041 Uiso 1 1 calc R . . C8 C 0.8212(5) 0.5759(2) 0.7708(5) 0.0255(10) Uani 1 1 d . . . C9 C 0.9655(5) 0.5357(2) 0.7431(5) 0.0210(9) Uani 1 1 d . . . C10 C 0.8365(6) 0.3595(2) 0.8953(5) 0.0288(10) Uani 1 1 d . . . H10A H 0.7664 0.3517 0.9795 0.035 Uiso 1 1 calc R . . H10B H 0.9550 0.3443 0.9366 0.035 Uiso 1 1 calc R . . C11 C 0.6744(6) 0.6843(2) 0.6962(6) 0.0289(10) Uani 1 1 d . . . H11A H 0.6437 0.6983 0.7994 0.035 Uiso 1 1 calc R . . H11B H 0.5765 0.6593 0.6346 0.035 Uiso 1 1 calc R . . C12 C 0.7207(6) 0.7467(2) 0.6009(6) 0.0326(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Fe1 0.0297(4) 0.0246(4) 0.0384(5) 0.0024(3) 0.0076(3) -0.0040(3) P1 0.0338(7) 0.0185(6) 0.0261(7) 0.0009(5) 0.0040(5) -0.0030(5) O1 0.070(3) 0.041(2) 0.033(2) -0.0028(15) 0.0209(19) -0.0133(18) O2 0.0396(19) 0.0195(17) 0.041(2) 0.0020(13) -0.0030(16) 0.0005(13) O3 0.0380(19) 0.035(2) 0.044(2) 0.0009(15) -0.0029(16) 0.0053(14) O4 0.0307(17) 0.0200(17) 0.051(2) 0.0056(14) 0.0137(16) 0.0043(13) O5 0.030(2) 0.053(2) 0.067(3) 0.0326(19) 0.014(2) 0.0063(16) O6 0.0399(19) 0.0287(19) 0.058(2) 0.0082(16) 0.0129(18) 0.0053(15) N1 0.027(2) 0.023(2) 0.031(2) 0.0010(16) 0.0026(17) -0.0015(15) C1 0.025(2) 0.037(3) 0.040(3) 0.002(2) 0.007(2) -0.003(2) C2 0.027(2) 0.031(3) 0.050(3) 0.001(2) 0.005(2) 0.008(2) C3 0.030(3) 0.022(2) 0.037(3) 0.0022(19) 0.002(2) 0.0033(18) C4 0.028(2) 0.020(2) 0.024(2) -0.0046(17) -0.001(2) -0.0025(17) C5 0.035(3) 0.019(2) 0.023(2) -0.0018(17) -0.002(2) -0.0055(18) C6 0.035(3) 0.023(2) 0.029(3) 0.0027(19) 0.005(2) -0.0049(19) C7 0.030(3) 0.031(3) 0.043(3) 0.001(2) 0.010(2) 0.005(2) C8 0.028(2) 0.018(2) 0.030(3) 0.0009(18) 0.003(2) -0.0015(17) C9 0.021(2) 0.021(2) 0.021(2) -0.0014(17) 0.0014(18) -0.0020(17) C10 0.035(3) 0.020(2) 0.029(3) 0.0030(19) 0.001(2) -0.0030(18) C11 0.030(2) 0.019(2) 0.037(3) 0.0014(19) 0.004(2) 0.0037(17) C12 0.030(3) 0.027(3) 0.038(3) 0.007(2) -0.001(2) -0.003(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 Fe1 O2 1.959(3) 2_756 ? Fe1 O1 1.971(4) 3_766 ? Fe1 O5 2.046(3) . ? Fe1 N1 2.162(4) . ? Fe1 O4 2.211(3) . ? P1 O1 1.482(4) . ? P1 O2 1.501(3) . ? P1 O3 1.559(3) . ? P1 C10 1.814(4) . ? O1 Fe1 1.971(4) 3_766 ? O2 Fe1 1.959(3) 2_746 ? O3 H3A 0.8200 . ? O4 C8 1.359(5) . ? O4 C11 1.438(5) . ? O5 C12 1.259(6) . ? O6 C12 1.235(5) . ? N1 C1 1.321(6) . ? N1 C9 1.361(5) . ? C1 C2 1.398(7) . ? C1 H1B 0.9300 . ? C2 C3 1.362(7) . ? C2 H2B 0.9300 . ? C3 C4 1.409(6) . ? C3 H3B 0.9300 . ? C4 C9 1.410(6) . ? C4 C5 1.427(6) . ? C5 C6 1.376(6) . ? C5 C10 1.510(6) . ? C6 C7 1.408(6) . ? C6 H6A 0.9300 . ? C7 C8 1.354(6) . ? C7 H7A 0.9300 . ? C8 C9 1.415(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.525(6) . ? C11 H11A 0.9700 . ? C11 H11B 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 O2 Fe1 O1 99.39(15) 2_756 3_766 ? O2 Fe1 O5 102.44(15) 2_756 . ? O1 Fe1 O5 106.71(16) 3_766 . ? O2 Fe1 N1 112.58(13) 2_756 . ? O1 Fe1 N1 90.39(15) 3_766 . ? O5 Fe1 N1 137.85(14) . . ? O2 Fe1 O4 114.59(14) 2_756 . ? O1 Fe1 O4 145.54(14) 3_766 . ? O5 Fe1 O4 72.56(12) . . ? N1 Fe1 O4 71.98(12) . . ? O1 P1 O2 116.7(2) . . ? O1 P1 O3 106.0(2) . . ? O2 P1 O3 110.08(18) . . ? O1 P1 C10 108.6(2) . . ? O2 P1 C10 109.39(19) . . ? O3 P1 C10 105.4(2) . . ? P1 O1 Fe1 151.0(2) . 3_766 ? P1 O2 Fe1 138.3(2) . 2_746 ? P1 O3 H3A 109.5 . . ? C8 O4 C11 120.0(3) . . ? C8 O4 Fe1 119.1(3) . . ? C11 O4 Fe1 118.3(2) . . ? C12 O5 Fe1 122.8(3) . . ? C1 N1 C9 118.7(4) . . ? C1 N1 Fe1 122.7(3) . . ? C9 N1 Fe1 118.6(3) . . ? N1 C1 C2 122.3(4) . . ? N1 C1 H1B 118.8 . . ? C2 C1 H1B 118.8 . . ? C3 C2 C1 119.6(4) . . ? C3 C2 H2B 120.2 . . ? C1 C2 H2B 120.2 . . ? C2 C3 C4 120.0(4) . . ? C2 C3 H3B 120.0 . . ? C4 C3 H3B 120.0 . . ? C9 C4 C3 116.6(4) . . ? C9 C4 C5 119.0(4) . . ? C3 C4 C5 124.3(4) . . ? C6 C5 C4 118.5(4) . . ? C6 C5 C10 120.2(4) . . ? C4 C5 C10 121.2(4) . . ? C5 C6 C7 122.2(4) . . ? C5 C6 H6A 118.9 . . ? C7 C6 H6A 118.9 . . ? C8 C7 C6 119.8(4) . . ? C8 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? O4 C8 C7 126.6(4) . . ? O4 C8 C9 113.2(4) . . ? C7 C8 C9 120.3(4) . . ? N1 C9 C4 122.7(4) . . ? N1 C9 C8 117.1(4) . . ? C4 C9 C8 120.2(4) . . ? C5 C10 P1 111.2(3) . . ? C5 C10 H10A 109.4 . . ? P1 C10 H10A 109.4 . . ? C5 C10 H10B 109.4 . . ? P1 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O4 C11 C12 105.1(3) . . ? O4 C11 H11A 110.7 . . ? C12 C11 H11A 110.7 . . ? O4 C11 H11B 110.7 . . ? C12 C11 H11B 110.7 . . ? H11A C11 H11B 108.8 . . ? O6 C12 O5 124.4(4) . . ? O6 C12 C11 118.1(4) . . ? O5 C12 C11 117.5(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.403 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 935063'