Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Iwona Bryndal' _publ_contact_author_address ; Faculty of Chemistry University of Wroclaw Joliot-Curie 14 50-383 Wroclaw Poland ; _publ_contact_author_email isia@wcheto.chem.uni.wroc.pl _publ_contact_author_phone '48 71 3757338' loop_ _publ_author_name _publ_author_address 'Marian Kuczek' ;Department of Experimental and Molecular Biology, University of Opole, Kominka 4, 45-035 Opole, Poland ; 'Iwona Bryndal' ; Faculty of Chemistry, University of Wroclaw Joliot-Curie 14 50-383 Wroclaw Poland ; 'Tadeusz Lis' ; Faculty of Chemistry, University of Wroclaw Joliot-Curie 14 50-383 Wroclaw Poland ; _publ_section_title ; The 4-nitrophenyl phosphoric acid and its four different potassium salts: a solid state and kinetic study ; data_1 _database_code_depnum_ccdc_archive 'CCDC 279860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-NITROPHENYL PHOSPHORIC ACID ; _chemical_name_common '4-NITROPHENYL PHOSPHORIC ACID' _chemical_formula_moiety 'C6 H6 N O6 P' _chemical_formula_sum 'C6 H6 N O6 P' _chemical_formula_weight 219.09 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.370(3) _cell_length_b 6.213(3) _cell_length_c 12.481(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.31(3) _cell_angle_gamma 90.00 _cell_volume 406.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11729 _cell_measurement_theta_min 3.68 _cell_measurement_theta_max 34.97 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.788 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'KUMA KM4CCD \k-geometry diffractometr' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6544 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 34.97 _reflns_number_total 3040 _reflns_number_gt 2938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0511P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(6) _refine_ls_number_reflns 3040 _refine_ls_number_parameters 151 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 P P 0.57971(4) 0.68363(5) 0.401296(19) 0.00947(6) Uani 1 1 d . . . O1 O 0.47597(16) 0.62639(13) 0.27669(6) 0.01280(14) Uani 1 1 d . . . O2 O 0.70417(16) 0.90393(14) 0.39183(7) 0.01374(14) Uani 1 1 d . . . H2O H 0.692(4) 0.985(5) 0.437(2) 0.037(6) Uiso 1 1 d . . . O4 O 0.79505(15) 0.52123(14) 0.44756(7) 0.01451(15) Uani 1 1 d . . . H4O H 0.741(5) 0.406(5) 0.486(2) 0.048(7) Uiso 1 1 d . . . O3 O 0.37526(13) 0.68651(16) 0.46628(6) 0.01197(12) Uani 1 1 d . . . C1 C 0.38810(19) 0.42100(17) 0.24055(8) 0.01107(16) Uani 1 1 d . . . C2 C 0.4964(2) 0.32778(18) 0.16026(8) 0.01226(17) Uani 1 1 d . . . H2 H 0.628(3) 0.401(4) 0.1348(15) 0.024(5) Uiso 1 1 d . . . C3 C 0.4037(2) 0.13081(17) 0.11614(9) 0.01206(17) Uani 1 1 d . . . H3 H 0.460(4) 0.055(4) 0.0595(16) 0.030(5) Uiso 1 1 d . . . C4 C 0.20623(19) 0.03464(17) 0.15450(8) 0.01064(16) Uani 1 1 d . . . C5 C 0.1003(2) 0.12516(18) 0.23623(9) 0.01253(17) Uani 1 1 d . . . H5 H -0.030(4) 0.056(4) 0.2554(15) 0.026(5) Uiso 1 1 d . . . C6 C 0.1919(2) 0.32306(18) 0.27965(9) 0.01274(17) Uani 1 1 d . . . H6 H 0.129(4) 0.397(4) 0.3340(17) 0.027(5) Uiso 1 1 d . . . N N 0.10036(17) -0.16952(16) 0.10506(8) 0.01284(15) Uani 1 1 d . . . O5 O 0.19843(17) -0.25239(15) 0.03484(7) 0.01749(16) Uani 1 1 d . . . O6 O -0.08104(18) -0.24863(16) 0.13699(8) 0.02041(17) 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 P 0.01060(9) 0.00824(10) 0.01014(10) -0.00041(9) 0.00350(7) -0.00098(8) O1 0.0188(3) 0.0093(3) 0.0100(3) -0.0010(2) 0.0024(3) -0.0028(2) O2 0.0178(3) 0.0101(3) 0.0151(3) -0.0028(3) 0.0075(3) -0.0042(3) O4 0.0117(3) 0.0142(4) 0.0186(3) 0.0045(3) 0.0053(3) 0.0019(3) O3 0.0123(3) 0.0106(3) 0.0147(3) -0.0003(3) 0.0066(2) -0.0006(3) C1 0.0128(4) 0.0096(4) 0.0106(4) -0.0001(3) 0.0020(3) -0.0008(3) C2 0.0142(4) 0.0119(4) 0.0113(4) -0.0005(3) 0.0039(3) -0.0018(3) C3 0.0127(4) 0.0118(4) 0.0124(4) -0.0019(3) 0.0043(3) -0.0012(3) C4 0.0116(4) 0.0092(4) 0.0106(4) -0.0008(3) 0.0013(3) -0.0009(3) C5 0.0126(4) 0.0124(4) 0.0134(4) -0.0006(3) 0.0045(3) -0.0016(3) C6 0.0140(4) 0.0124(4) 0.0131(4) -0.0013(3) 0.0057(3) -0.0012(3) N 0.0134(4) 0.0108(4) 0.0136(4) -0.0010(3) 0.0011(3) -0.0012(3) O5 0.0210(4) 0.0163(4) 0.0156(3) -0.0050(3) 0.0049(3) -0.0011(3) O6 0.0190(4) 0.0172(4) 0.0263(4) -0.0038(3) 0.0078(3) -0.0083(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 P O3 1.4977(9) . ? P O2 1.5387(11) . ? P O4 1.5505(10) . ? P O1 1.5768(10) . ? O1 C1 1.4014(14) . ? O2 H2O 0.77(3) . ? O4 H4O 0.94(3) . ? C1 C2 1.3878(15) . ? C1 C6 1.3919(15) . ? C2 C3 1.3899(16) . ? C2 H2 0.95(2) . ? C3 C4 1.3880(15) . ? C3 H3 0.95(2) . ? C4 C5 1.3885(15) . ? C4 N 1.4708(15) . ? C5 C6 1.3906(17) . ? C5 H5 0.90(2) . ? C6 H6 0.94(2) . ? N O5 1.2278(13) . ? N O6 1.2308(13) . ? 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 O3 P O2 114.30(5) . . ? O3 P O4 112.38(5) . . ? O2 P O4 107.81(6) . . ? O3 P O1 113.03(5) . . ? O2 P O1 101.12(5) . . ? O4 P O1 107.41(5) . . ? C1 O1 P 123.15(7) . . ? P O2 H2O 115(2) . . ? P O4 H4O 113.5(17) . . ? C2 C1 C6 122.38(10) . . ? C2 C1 O1 116.63(9) . . ? C6 C1 O1 120.89(9) . . ? C1 C2 C3 118.93(10) . . ? C1 C2 H2 119.8(13) . . ? C3 C2 H2 121.2(13) . . ? C4 C3 C2 118.54(10) . . ? C4 C3 H3 115.6(14) . . ? C2 C3 H3 125.8(14) . . ? C3 C4 C5 122.80(10) . . ? C3 C4 N 118.81(9) . . ? C5 C4 N 118.38(9) . . ? C4 C5 C6 118.56(10) . . ? C4 C5 H5 118.0(14) . . ? C6 C5 H5 123.3(14) . . ? C5 C6 C1 118.77(10) . . ? C5 C6 H6 124.2(13) . . ? C1 C6 H6 117.1(13) . . ? O5 N O6 123.58(11) . . ? O5 N C4 118.35(9) . . ? O6 N C4 118.06(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P O1 C1 167.42(8) . . . . ? O3 P O1 C1 -69.95(9) . . . . ? O4 P O1 C1 54.57(9) . . . . ? P O1 C1 C2 -126.67(9) . . . . ? P O1 C1 C6 56.82(12) . . . . ? O1 C1 C2 C3 -175.60(9) . . . . ? O1 C1 C6 C5 175.96(10) . . . . ? N C4 C3 C2 177.58(9) . . . . ? N C4 C5 C6 -177.08(9) . . . . ? C3 C4 N O5 3.19(14) . . . . ? C5 C4 N O5 -178.11(10) . . . . ? C3 C4 N O6 -177.26(10) . . . . ? C5 C4 N O6 1.44(14) . . . . ? C6 C1 C2 C3 0.86(16) . . . . ? C1 C2 C3 C4 -0.16(15) . . . . ? C2 C3 C4 C5 -1.06(16) . . . . ? C3 C4 C5 C6 1.56(16) . . . . ? H2O O2 P O1 144.0(19) . . . . ? H4O O4 P O1 -98.5(18) . . . . ? 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 O2 H2O O3 0.77(3) 1.83(3) 2.5928(14) 173(2) 2_656 O4 H4O O3 0.94(3) 1.66(3) 2.5956(15) 171(3) 2_646 C3 H3 O5 0.95(2) 2.35(2) 2.7269(18) 102.8(15) . C5 H5 O6 0.90(2) 2.38(2) 2.7132(18) 101.9(15) . _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 34.97 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.551 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.074 # Attachment 'CCDC279861.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 279861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; SEMIPOTASSIUM SALT OF 4-NITROPHENYL PHOSPHORIC ACID ; _chemical_name_common 'SEMIPOTASSIUM SALT OF 4-NITROPHENYL PHOSPHORIC ACID' _chemical_formula_moiety 'C12 H11 K N2 O12 P2' _chemical_formula_sum 'C12 H11 K N2 O12 P2' _chemical_formula_weight 476.27 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M 'P 21/n' _symmetry_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 7.669(2) _cell_length_b 19.817(4) _cell_length_c 11.707(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.90(3) _cell_angle_gamma 90.00 _cell_volume 1734.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26796 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 35 _exptl_crystal_description PLATE _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 0.564 _exptl_absorpt_correction_type ANALYTICAL _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details ; XPREP-Brucker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'KUMA KM4CCD \k-geometry diffractometr' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33149 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 35.00 _reflns_number_total 7401 _reflns_number_gt 6697 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0370P)^2^+0.9380P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7401 _refine_ls_number_parameters 304 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 K K 0.78882(3) 0.590258(12) 0.59144(2) 0.01463(5) Uani 1 1 d . . . P1 P 0.75474(3) 0.494804(13) 0.29763(2) 0.01006(5) Uani 1 1 d . . . O11 O 0.74963(11) 0.51816(4) 0.16507(7) 0.01278(13) Uani 1 1 d . . . O21 O 0.83073(11) 0.42542(4) 0.30901(7) 0.01312(14) Uani 1 1 d . . . O31 O 0.86146(10) 0.54812(4) 0.38000(7) 0.01257(13) Uani 1 1 d . . . H3O H 0.984(2) 0.5491(9) 0.3900(15) 0.015 Uiso 1 1 d . . . O41 O 0.56012(10) 0.49808(4) 0.31307(7) 0.01423(14) Uani 1 1 d . . . H4O H 0.530(2) 0.5380(9) 0.3551(16) 0.017 Uiso 1 1 d . . . C11 C 0.66584(13) 0.57648(5) 0.11507(9) 0.01083(16) Uani 1 1 d . . . C21 C 0.59883(14) 0.57407(5) -0.00593(9) 0.01241(17) Uani 1 1 d . . . H21 H 0.617(2) 0.5360(8) -0.0479(15) 0.014(4) Uiso 1 1 d . . . C31 C 0.50968(15) 0.62961(5) -0.06346(9) 0.01338(17) Uani 1 1 d . . . H31 H 0.459(3) 0.6286(9) -0.1429(17) 0.022(4) Uiso 1 1 d . . . C41 C 0.49214(14) 0.68667(5) 0.00222(9) 0.01249(16) Uani 1 1 d . . . C51 C 0.56155(15) 0.69034(5) 0.12213(10) 0.01371(17) Uani 1 1 d . . . H51 H 0.548(2) 0.7285(9) 0.1633(16) 0.018(4) Uiso 1 1 d . . . C61 C 0.64972(15) 0.63453(5) 0.17940(9) 0.01316(17) Uani 1 1 d . . . H61 H 0.697(3) 0.6375(10) 0.2592(17) 0.024(5) Uiso 1 1 d . . . N1 N 0.39348(14) 0.74460(5) -0.05735(9) 0.01651(17) Uani 1 1 d . . . O51 O 0.32404(16) 0.73935(5) -0.16204(9) 0.0278(2) Uani 1 1 d . . . O61 O 0.38361(15) 0.79573(5) 0.00005(9) 0.0252(2) Uani 1 1 d . . . P2 P 0.69756(3) 0.389520(13) 0.56681(2) 0.00987(5) Uani 1 1 d . . . O12 O 0.78909(11) 0.33295(4) 0.66022(7) 0.01392(14) Uani 1 1 d . . . O22 O 0.69732(12) 0.35131(4) 0.45106(7) 0.01498(14) Uani 1 1 d . . . H2O H 0.737(3) 0.3731(13) 0.401(2) 0.050(7) Uiso 1 1 d . . . O32 O 0.50973(11) 0.40173(4) 0.57978(8) 0.01479(14) Uani 1 1 d . . . O42 O 0.81185(10) 0.45209(4) 0.58202(7) 0.01256(13) Uani 1 1 d . . . C12 C 0.84479(14) 0.34375(5) 0.77919(9) 0.01147(16) Uani 1 1 d . . . C22 C 0.93099(15) 0.28959(5) 0.84433(9) 0.01369(17) Uani 1 1 d . . . H22 H 0.953(2) 0.2462(9) 0.8075(16) 0.022(4) Uiso 1 1 d . . . C32 C 1.00261(15) 0.29734(5) 0.96349(10) 0.01434(18) Uani 1 1 d . . . H32 H 1.066(2) 0.2649(9) 1.0071(15) 0.019(4) Uiso 1 1 d . . . C42 C 0.98599(14) 0.35981(5) 1.01411(9) 0.01186(16) Uani 1 1 d . . . C52 C 0.89539(14) 0.41337(5) 0.95149(9) 0.01295(17) Uani 1 1 d . . . H52 H 0.881(2) 0.4557(9) 0.9880(16) 0.020(4) Uiso 1 1 d . . . C62 C 0.82168(15) 0.40516(5) 0.83286(9) 0.01290(17) Uani 1 1 d . . . H62 H 0.758(2) 0.4403(9) 0.7897(16) 0.020(4) Uiso 1 1 d . . . N2 N 1.07791(13) 0.37126(5) 1.13569(8) 0.01382(16) Uani 1 1 d . . . O52 O 1.12076(15) 0.32234(5) 1.20071(8) 0.02318(19) Uani 1 1 d . . . O62 O 1.11312(12) 0.42999(4) 1.16723(7) 0.01684(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 K 0.01832(10) 0.01316(9) 0.01072(9) -0.00065(7) -0.00035(7) 0.00216(7) P1 0.01014(10) 0.00976(10) 0.00993(11) 0.00028(8) 0.00149(8) 0.00026(8) O11 0.0162(3) 0.0112(3) 0.0106(3) 0.0013(2) 0.0023(3) 0.0031(3) O21 0.0157(3) 0.0103(3) 0.0135(3) 0.0014(2) 0.0036(3) 0.0021(3) O31 0.0108(3) 0.0132(3) 0.0128(3) -0.0017(2) 0.0008(2) -0.0008(2) O41 0.0101(3) 0.0152(3) 0.0175(4) -0.0014(3) 0.0033(3) -0.0005(3) C11 0.0112(4) 0.0099(4) 0.0114(4) 0.0010(3) 0.0023(3) 0.0002(3) C21 0.0147(4) 0.0116(4) 0.0107(4) 0.0001(3) 0.0024(3) -0.0001(3) C31 0.0148(4) 0.0137(4) 0.0108(4) 0.0012(3) 0.0012(3) -0.0004(3) C41 0.0130(4) 0.0107(4) 0.0133(4) 0.0024(3) 0.0017(3) 0.0006(3) C51 0.0159(4) 0.0110(4) 0.0136(4) -0.0005(3) 0.0019(3) 0.0009(3) C61 0.0163(4) 0.0114(4) 0.0110(4) -0.0004(3) 0.0014(3) 0.0007(3) N1 0.0168(4) 0.0147(4) 0.0175(4) 0.0046(3) 0.0027(3) 0.0023(3) O51 0.0362(5) 0.0241(5) 0.0177(4) 0.0059(3) -0.0055(4) 0.0077(4) O61 0.0333(5) 0.0145(4) 0.0270(5) 0.0013(3) 0.0051(4) 0.0088(4) P2 0.00952(10) 0.00948(10) 0.01016(11) 0.00008(8) 0.00124(8) -0.00065(8) O12 0.0184(4) 0.0107(3) 0.0109(3) 0.0000(2) -0.0005(3) 0.0011(3) O22 0.0216(4) 0.0125(3) 0.0116(3) -0.0015(3) 0.0051(3) -0.0035(3) O32 0.0097(3) 0.0170(3) 0.0176(4) -0.0015(3) 0.0029(3) -0.0005(3) O42 0.0116(3) 0.0103(3) 0.0155(3) -0.0005(2) 0.0023(3) -0.0017(2) C12 0.0118(4) 0.0108(4) 0.0111(4) 0.0002(3) 0.0013(3) -0.0006(3) C22 0.0171(4) 0.0101(4) 0.0131(4) 0.0000(3) 0.0016(3) 0.0015(3) C32 0.0175(4) 0.0114(4) 0.0133(4) 0.0015(3) 0.0016(3) 0.0029(3) C42 0.0125(4) 0.0127(4) 0.0098(4) 0.0005(3) 0.0013(3) 0.0012(3) C52 0.0140(4) 0.0113(4) 0.0130(4) -0.0002(3) 0.0018(3) 0.0016(3) C62 0.0146(4) 0.0110(4) 0.0122(4) 0.0007(3) 0.0010(3) 0.0027(3) N2 0.0150(4) 0.0155(4) 0.0108(4) 0.0006(3) 0.0025(3) 0.0025(3) O52 0.0350(5) 0.0180(4) 0.0134(4) 0.0039(3) -0.0014(3) 0.0069(4) O62 0.0204(4) 0.0160(4) 0.0138(3) -0.0023(3) 0.0031(3) -0.0018(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 K O61 2.6693(11) 4_676 ? K O32 2.6900(13) 3_666 ? K O42 2.7476(10) . ? K O31 2.7841(10) . ? K O62 2.7856(11) 3_767 ? K O21 2.9067(12) 3_766 ? K O52 2.9408(11) 3_767 ? K N2 3.2207(12) 3_767 ? P1 O21 1.4877(9) . ? P1 O31 1.5373(9) . ? P1 O41 1.5444(9) . ? P1 O11 1.6115(9) . ? O11 C11 1.3869(12) . ? O31 H3O 0.918(17) . ? O41 H4O 0.987(18) . ? C11 C61 1.3954(15) . ? C11 C21 1.3956(15) . ? C21 C31 1.3881(15) . ? C21 H21 0.928(17) . ? C31 C41 1.3908(15) . ? C31 H31 0.925(19) . ? C41 C51 1.3877(15) . ? C41 N1 1.4632(14) . ? C51 C61 1.3884(15) . ? C51 H51 0.914(18) . ? C61 H61 0.926(19) . ? N1 O51 1.2268(14) . ? N1 O61 1.2274(14) . ? P2 O32 1.5013(9) . ? P2 O42 1.5059(8) . ? P2 O22 1.5520(9) . ? P2 O12 1.6132(9) . ? O12 C12 1.3793(13) . ? O22 H2O 0.84(3) . ? C12 C22 1.3948(14) . ? C12 C62 1.3989(15) . ? C22 C32 1.3889(16) . ? C22 H22 0.992(18) . ? C32 C42 1.3905(15) . ? C32 H32 0.895(18) . ? C42 C52 1.3854(14) . ? C42 N2 1.4582(14) . ? C52 C62 1.3871(15) . ? C52 H52 0.959(19) . ? C62 H62 0.931(18) . ? N2 O52 1.2311(13) . ? N2 O62 1.2327(13) . ? 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 O61 K O32 85.07(3) 4_676 3_666 ? O61 K O42 143.29(3) 4_676 . ? O32 K O42 94.62(3) 3_666 . ? O61 K O31 76.76(3) 4_676 . ? O32 K O31 70.19(3) 3_666 . ? O42 K O31 68.77(2) . . ? O61 K O62 119.50(3) 4_676 3_767 ? O32 K O62 139.15(3) 3_666 3_767 ? O42 K O62 83.80(3) . 3_767 ? O31 K O62 142.77(3) . 3_767 ? O61 K O21 84.97(3) 4_676 3_766 ? O32 K O21 156.38(3) 3_666 3_766 ? O42 K O21 80.90(2) . 3_766 ? O31 K O21 86.69(3) . 3_766 ? O62 K O21 63.80(4) 3_767 3_766 ? O61 K O52 78.35(3) 4_676 3_767 ? O32 K O52 125.87(3) 3_666 3_767 ? O42 K O52 127.94(3) . 3_767 ? O31 K O52 148.80(3) . 3_767 ? O62 K O52 44.38(3) 3_767 3_767 ? O21 K O52 72.61(4) 3_766 3_767 ? O21 P1 O31 115.84(5) . . ? O21 P1 O41 113.44(5) . . ? O31 P1 O41 106.90(5) . . ? O21 P1 O11 106.06(5) . . ? O31 P1 O11 107.56(5) . . ? O41 P1 O11 106.52(5) . . ? C11 O11 P1 123.72(7) . . ? P1 O21 K 118.21(4) . 3_766 ? P1 O31 K 125.43(5) . . ? P1 O31 H3O 118.7(11) . . ? K O31 H3O 106.3(11) . . ? P1 O41 H4O 115.6(10) . . ? O11 C11 C61 123.21(9) . . ? O11 C11 C21 115.51(9) . . ? C61 C11 C21 121.28(9) . . ? C31 C21 C11 119.68(10) . . ? C31 C21 H21 120.2(11) . . ? C11 C21 H21 120.1(11) . . ? C21 C31 C41 118.32(10) . . ? C21 C31 H31 121.5(12) . . ? C41 C31 H31 120.2(12) . . ? C51 C41 C31 122.63(10) . . ? C51 C41 N1 118.81(10) . . ? C31 C41 N1 118.55(10) . . ? C41 C51 C61 118.83(10) . . ? C41 C51 H51 120.9(11) . . ? C61 C51 H51 120.2(11) . . ? C51 C61 C11 119.23(10) . . ? C51 C61 H61 118.4(12) . . ? C11 C61 H61 122.4(12) . . ? O51 N1 O61 123.43(10) . . ? O51 N1 C41 118.20(10) . . ? O61 N1 C41 118.38(10) . . ? N1 O61 K 166.84(9) . 4_575 ? O32 P2 O42 113.68(5) . . ? O32 P2 O22 110.66(5) . . ? O42 P2 O22 113.09(5) . . ? O32 P2 O12 109.00(5) . . ? O42 P2 O12 109.78(5) . . ? O22 P2 O12 99.69(5) . . ? C12 O12 P2 124.50(7) . . ? P2 O22 H2O 115.2(17) . . ? P2 O32 K 127.62(5) . 3_666 ? P2 O42 K 141.66(5) . . ? O12 C12 C22 115.78(9) . . ? O12 C12 C62 123.15(9) . . ? C22 C12 C62 121.06(10) . . ? C32 C22 C12 119.80(10) . . ? C32 C22 H22 117.7(11) . . ? C12 C22 H22 122.3(11) . . ? C22 C32 C42 118.24(10) . . ? C22 C32 H32 122.5(11) . . ? C42 C32 H32 119.1(11) . . ? C52 C42 C32 122.64(10) . . ? C52 C42 N2 118.25(9) . . ? C32 C42 N2 118.96(9) . . ? C42 C52 C62 118.95(10) . . ? C42 C52 H52 121.9(11) . . ? C62 C52 H52 119.2(11) . . ? C52 C62 C12 119.18(9) . . ? C52 C62 H62 120.1(11) . . ? C12 C62 H62 120.7(11) . . ? O52 N2 O62 123.23(10) . . ? O52 N2 C42 119.02(10) . . ? O62 N2 C42 117.72(9) . . ? N2 O52 K 91.65(7) . 3_767 ? N2 O62 K 99.16(6) . 3_767 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O21 P1 O11 C11 171.17(8) . . . . ? O31 P1 O11 C11 -64.30(9) . . . . ? O41 P1 O11 C11 50.03(9) . . . . ? P1 O11 C11 C21 -150.41(8) . . . . ? P1 O11 C11 C61 30.26(14) . . . . ? O11 C11 C21 C31 178.75(9) . . . . ? O11 C11 C61 C51 -179.18(10) . . . . ? N1 C41 C31 C21 -178.13(10) . . . . ? N1 C41 C51 C61 177.76(10) . . . . ? C31 C41 N1 O51 2.91(16) . . . . ? C51 C41 N1 O51 -175.91(11) . . . . ? C31 C41 N1 O61 -177.49(11) . . . . ? C51 C41 N1 O61 3.69(16) . . . . ? C61 C11 C21 C31 -1.90(16) . . . . ? C11 C21 C31 C41 0.80(16) . . . . ? C21 C31 C41 C51 0.65(17) . . . . ? C31 C41 C51 C61 -1.02(17) . . . . ? O22 P2 O12 C12 170.75(9) . . . . ? O32 P2 O12 C12 -73.32(10) . . . . ? O42 P2 O12 C12 51.79(10) . . . . ? P2 O12 C12 C22 -176.14(8) . . . . ? P2 O12 C12 C62 2.40(15) . . . . ? O12 C12 C22 C32 175.58(10) . . . . ? O12 C12 C62 C52 -174.53(10) . . . . ? N2 C42 C32 C22 -172.99(10) . . . . ? N2 C42 C52 C62 173.96(10) . . . . ? C32 C42 N2 O52 -21.96(16) . . . . ? C52 C42 N2 O52 162.34(11) . . . . ? C32 C42 N2 O62 156.12(10) . . . . ? C52 C42 N2 O62 -19.58(15) . . . . ? C62 C12 C22 C32 -3.00(17) . . . . ? C12 C22 C32 C42 -0.20(17) . . . . ? C22 C32 C42 C52 2.51(17) . . . . ? C32 C42 C52 C62 -1.58(17) . . . . ? O11 P1 O31 H3O -74.6(13) . . . . ? O11 P1 O41 H4O -101.3(12) . . . . ? O12 P2 O22 H2O -131.2(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 O31 H3O O42 0.918(17) 1.530(17) 2.4449(13) 174.7(18) 3_766 O41 H4O O32 0.987(18) 1.484(18) 2.4703(12) 178.3(17) 3_666 O22 H2O O21 0.84(3) 1.76(3) 2.5940(12) 174(3) . C61 H61 O31 0.926(19) 2.435(19) 3.0629(15) 125.1(15) . C62 H62 O42 0.931(18) 2.564(18) 3.0653(14) 114.1(14) . C31 H31 O51 0.925(19) 2.415(19) 2.7119(15) 98.6(13) . C32 H32 O52 0.895(18) 2.487(18) 2.7669(16) 98.7(13) . C51 H51 O61 0.914(18) 2.439(17) 2.7196(15) 97.9(12) . _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 35.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.651 _refine_diff_density_min -0.436 _refine_diff_density_rms 0.082 # Attachment 'CCDC279862.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 279862' _audit_creation_method SHELXL-97 _chemical_name_systematic ; POTASSIUM 4-NITROPHENYL HYDROGEN PHOSPHATE METHANOL SOLVATE ; _chemical_name_common 'POTASSIUM 4-NITROPHENYL HYDROGEN PHOSPHATE METHANOL SOLVATE' _chemical_formula_moiety 'C7 H9 K N O7 P' _chemical_formula_sum 'C7 H9 K N O7 P' _chemical_formula_weight 289.22 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' K K 0.2009 0.2494 '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 7.373(3) _cell_length_b 9.561(3) _cell_length_c 16.320(4) _cell_angle_alpha 84.44(3) _cell_angle_beta 89.23(3) _cell_angle_gamma 84.47(3) _cell_volume 1139.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13582 _cell_measurement_theta_min 3.14 _cell_measurement_theta_max 29 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.686 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.629 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7234 _exptl_absorpt_correction_T_max 0.9573 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'KUMA KM4CCD \k-geometry diffractometr' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15626 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 29.00 _reflns_number_total 5844 _reflns_number_gt 5062 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0456P)^2^+0.3569P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5844 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 K1 K 0.32474(4) 0.64731(3) -0.077081(19) 0.01309(8) Uani 1 1 d . . . K2 K 0.32207(4) 0.16355(3) -0.063399(19) 0.01370(8) Uani 1 1 d . . . P1 P 0.20076(5) 0.41004(4) 0.10531(2) 0.01069(9) Uani 1 1 d . . . O11 O 0.35343(15) 0.35384(12) 0.17550(6) 0.0147(2) Uani 1 1 d . . . O31 O 0.05009(15) 0.30490(12) 0.11743(7) 0.0148(2) Uani 1 1 d . . . H3O1 H 0.086(4) 0.230(3) 0.1078(18) 0.056(9) Uiso 1 1 d . . . O41 O 0.11086(15) 0.54913(12) 0.12654(7) 0.0169(2) Uani 1 1 d . . . O21 O 0.30568(15) 0.40094(12) 0.02756(6) 0.0147(2) Uani 1 1 d . . . C11 C 0.3329(2) 0.36090(16) 0.25903(9) 0.0140(3) Uani 1 1 d . . . C21 C 0.4937(2) 0.35293(18) 0.30330(10) 0.0179(3) Uani 1 1 d . . . H21 H 0.601(3) 0.349(2) 0.2745(13) 0.023(5) Uiso 1 1 d . . . C31 C 0.4874(2) 0.35519(19) 0.38797(10) 0.0197(3) Uani 1 1 d . . . H31 H 0.595(3) 0.351(2) 0.4186(13) 0.028(6) Uiso 1 1 d . . . C41 C 0.3190(2) 0.36654(18) 0.42636(9) 0.0176(3) Uani 1 1 d . . . C51 C 0.1571(2) 0.37492(18) 0.38364(10) 0.0186(3) Uani 1 1 d . . . H51 H 0.044(3) 0.380(2) 0.4134(12) 0.017(5) Uiso 1 1 d . . . C61 C 0.1645(2) 0.37148(17) 0.29851(10) 0.0164(3) Uani 1 1 d . . . H61 H 0.054(3) 0.373(2) 0.2686(14) 0.032(6) Uiso 1 1 d . . . N1 N 0.3122(2) 0.36924(16) 0.51615(8) 0.0223(3) Uani 1 1 d . . . O51 O 0.45543(19) 0.34531(16) 0.55433(8) 0.0316(3) Uani 1 1 d . . . O61 O 0.16346(19) 0.39732(18) 0.54849(8) 0.0359(4) Uani 1 1 d . . . P2 P 0.20754(5) -0.09524(4) 0.08360(2) 0.01065(9) Uani 1 1 d . . . O12 O 0.34775(14) -0.14760(12) 0.15903(6) 0.0141(2) Uani 1 1 d . . . O32 O 0.04555(15) -0.18957(13) 0.09869(7) 0.0159(2) Uani 1 1 d . . . H3O2 H 0.077(4) -0.269(3) 0.1019(16) 0.042(8) Uiso 1 1 d . . . O42 O 0.12819(16) 0.05307(12) 0.09087(7) 0.0170(2) Uani 1 1 d . . . O22 O 0.31939(14) -0.12378(12) 0.00957(7) 0.0147(2) Uani 1 1 d . . . C12 C 0.3047(2) -0.12750(17) 0.24055(9) 0.0141(3) Uani 1 1 d . . . C62 C 0.2145(2) -0.22745(18) 0.28856(10) 0.0187(3) Uani 1 1 d . . . H62 H 0.173(3) -0.307(2) 0.2619(13) 0.026(5) Uiso 1 1 d . . . C52 C 0.1813(2) -0.20959(19) 0.37136(11) 0.0212(3) Uani 1 1 d . . . H52 H 0.121(3) -0.273(2) 0.4051(14) 0.030(6) Uiso 1 1 d . . . C42 C 0.2422(2) -0.09318(19) 0.40275(10) 0.0197(3) Uani 1 1 d . . . C32 C 0.3330(2) 0.00587(19) 0.35531(10) 0.0211(3) Uani 1 1 d . . . H32 H 0.376(3) 0.080(3) 0.3812(15) 0.039(6) Uiso 1 1 d . . . C22 C 0.3636(2) -0.01131(18) 0.27272(10) 0.0186(3) Uani 1 1 d . . . H22 H 0.427(3) 0.053(2) 0.2372(13) 0.027(5) Uiso 1 1 d . . . N2 N 0.2142(2) -0.07541(19) 0.49075(9) 0.0274(3) Uani 1 1 d . . . O52 O 0.2716(2) 0.02661(17) 0.51820(8) 0.0419(4) Uani 1 1 d . . . O62 O 0.1357(2) -0.16488(19) 0.53310(8) 0.0393(4) Uani 1 1 d . . . O7 O 0.77010(17) 0.07514(14) 0.17649(8) 0.0230(3) Uani 1 1 d . . . H7 H 0.855(3) 0.057(3) 0.1476(15) 0.031(6) Uiso 1 1 d . . . C7 C 0.8351(3) 0.0585(2) 0.25943(12) 0.0246(4) Uani 1 1 d . . . H71 H 0.736(3) 0.073(2) 0.2968(14) 0.033(6) Uiso 1 1 d . . . H72 H 0.928(4) 0.119(3) 0.2685(17) 0.056(8) Uiso 1 1 d . . . H73 H 0.886(4) -0.035(3) 0.2739(17) 0.056(8) Uiso 1 1 d . . . O8 O -0.25228(17) 0.57747(13) 0.17240(7) 0.0178(2) Uani 1 1 d . . . H8 H -0.148(3) 0.562(3) 0.1618(14) 0.031(6) Uiso 1 1 d . . . C8 C -0.2665(3) 0.6377(2) 0.24924(11) 0.0227(4) Uani 1 1 d . . . H81 H -0.198(3) 0.577(2) 0.2912(13) 0.025(5) Uiso 1 1 d . . . H82 H -0.221(4) 0.731(3) 0.2433(17) 0.051(8) Uiso 1 1 d . . . H83 H -0.399(3) 0.644(2) 0.2663(13) 0.024(5) 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 K1 0.01151(15) 0.01333(17) 0.01454(15) -0.00216(11) -0.00081(11) -0.00086(11) K2 0.01084(15) 0.01377(17) 0.01609(15) 0.00050(12) -0.00101(11) -0.00084(11) P1 0.01030(17) 0.00752(18) 0.01416(17) -0.00059(13) -0.00042(13) -0.00076(13) O11 0.0129(5) 0.0191(6) 0.0116(5) -0.0009(4) 0.0004(4) 0.0006(4) O31 0.0127(5) 0.0082(5) 0.0239(6) -0.0036(4) 0.0018(4) -0.0017(4) O41 0.0177(5) 0.0077(5) 0.0252(6) -0.0019(4) 0.0016(4) -0.0003(4) O21 0.0150(5) 0.0148(6) 0.0142(5) -0.0001(4) -0.0001(4) -0.0018(4) C11 0.0178(7) 0.0113(7) 0.0127(7) -0.0004(5) -0.0008(5) -0.0008(5) C21 0.0145(7) 0.0219(9) 0.0174(7) -0.0011(6) 0.0007(6) -0.0026(6) C31 0.0190(8) 0.0231(9) 0.0172(7) -0.0014(6) -0.0042(6) -0.0029(6) C41 0.0241(8) 0.0159(8) 0.0128(7) -0.0020(6) -0.0004(6) -0.0016(6) C51 0.0172(8) 0.0207(9) 0.0175(7) -0.0028(6) 0.0025(6) 0.0005(6) C61 0.0153(7) 0.0174(8) 0.0162(7) -0.0007(6) -0.0002(6) 0.0000(6) N1 0.0275(8) 0.0246(8) 0.0147(6) -0.0040(5) -0.0014(5) -0.0004(6) O51 0.0311(7) 0.0431(9) 0.0193(6) -0.0038(6) -0.0070(5) 0.0039(6) O61 0.0298(7) 0.0588(10) 0.0183(6) -0.0113(6) 0.0028(5) 0.0061(7) P2 0.01030(17) 0.00710(18) 0.01457(18) -0.00113(13) -0.00042(13) -0.00079(13) O12 0.0118(5) 0.0163(6) 0.0139(5) -0.0020(4) -0.0007(4) 0.0008(4) O32 0.0107(5) 0.0085(6) 0.0282(6) 0.0011(4) -0.0015(4) -0.0016(4) O42 0.0207(6) 0.0076(5) 0.0225(6) -0.0014(4) 0.0002(4) 0.0002(4) O22 0.0137(5) 0.0152(6) 0.0155(5) -0.0031(4) 0.0000(4) -0.0010(4) C12 0.0115(7) 0.0158(8) 0.0142(7) -0.0004(5) -0.0007(5) 0.0020(5) C62 0.0182(8) 0.0179(8) 0.0198(7) 0.0000(6) -0.0012(6) -0.0025(6) C52 0.0185(8) 0.0242(9) 0.0197(8) 0.0050(7) 0.0013(6) -0.0024(7) C42 0.0185(8) 0.0255(9) 0.0135(7) -0.0002(6) -0.0005(6) 0.0050(6) C32 0.0262(9) 0.0182(9) 0.0191(8) -0.0042(6) -0.0022(6) -0.0007(7) C22 0.0209(8) 0.0166(8) 0.0181(7) -0.0013(6) 0.0011(6) -0.0018(6) N2 0.0233(8) 0.0401(10) 0.0163(7) -0.0002(6) -0.0004(6) 0.0067(7) O52 0.0606(11) 0.0447(10) 0.0215(7) -0.0120(6) -0.0004(7) -0.0018(8) O62 0.0369(8) 0.0616(11) 0.0184(6) 0.0045(6) 0.0061(6) -0.0089(7) O7 0.0179(6) 0.0288(7) 0.0216(6) 0.0008(5) 0.0029(5) -0.0027(5) C7 0.0203(8) 0.0259(10) 0.0267(9) -0.0010(7) -0.0027(7) 0.0010(7) O8 0.0166(6) 0.0214(6) 0.0164(5) -0.0054(4) 0.0022(4) -0.0037(5) C8 0.0265(9) 0.0234(10) 0.0189(8) -0.0063(7) 0.0009(7) -0.0013(7) _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 K1 O22 2.7154(14) 1_565 ? K1 O21 2.7861(15) . ? K1 O31 2.8332(16) 2_565 ? K1 O21 2.8348(16) 2_665 ? K1 O11 2.8471(16) 2_665 ? K1 O8 2.8662(15) 2_565 ? K1 O7 3.0003(17) 2_665 ? K1 K2 4.1448(15) 2_665 ? K1 K1 4.2827(18) 2_665 ? K2 O32 2.7612(16) 2 ? K2 O22 2.7764(16) 2_655 ? K2 O21 2.8223(15) . ? K2 O12 2.8736(16) 2_655 ? K2 O22 2.8881(15) . ? K2 O8 2.9131(16) 2_565 ? K2 O42 3.0293(16) . ? K2 O7 3.1977(17) 2_655 ? P1 O21 1.4826(12) . ? P1 O41 1.4970(13) . ? P1 O31 1.5667(13) . ? P1 O11 1.6329(13) . ? O11 C11 1.3771(18) . ? O11 K1 2.8471(16) 2_665 ? O31 K1 2.8332(16) 2_565 ? O31 H3O1 0.77(3) . ? O21 K1 2.8348(16) 2_665 ? C11 C21 1.389(2) . ? C11 C61 1.391(2) . ? C21 C31 1.384(2) . ? C21 H21 0.91(2) . ? C31 C41 1.383(2) . ? C31 H31 0.94(2) . ? C41 C51 1.382(2) . ? C41 N1 1.468(2) . ? C51 C61 1.393(2) . ? C51 H51 0.96(2) . ? C61 H61 0.96(2) . ? N1 O51 1.225(2) . ? N1 O61 1.228(2) . ? P2 O22 1.4860(12) . ? P2 O42 1.4959(13) . ? P2 O32 1.5676(13) . ? P2 O12 1.6278(12) . ? O12 C12 1.3907(18) . ? O12 K2 2.8736(16) 2_655 ? O32 K2 2.7612(16) 2 ? O32 H3O2 0.77(3) . ? O22 K1 2.7154(14) 1_545 ? O22 K2 2.7764(16) 2_655 ? C12 C22 1.382(2) . ? C12 C62 1.391(2) . ? C62 C52 1.394(2) . ? C62 H62 0.99(2) . ? C52 C42 1.384(3) . ? C52 H52 0.92(2) . ? C42 C32 1.382(2) . ? C42 N2 1.472(2) . ? C32 C22 1.386(2) . ? C32 H32 0.94(3) . ? C22 H22 0.95(2) . ? N2 O52 1.225(2) . ? N2 O62 1.231(2) . ? O7 C7 1.431(2) . ? O7 K1 3.0003(17) 2_665 ? O7 K2 3.1977(17) 2_655 ? O7 H7 0.79(2) . ? C7 H71 0.96(2) . ? C7 H72 0.96(3) . ? C7 H73 0.94(3) . ? O8 C8 1.428(2) . ? O8 K1 2.8662(15) 2_565 ? O8 K2 2.9131(16) 2_565 ? O8 H8 0.79(2) . ? C8 K2 3.427(2) 2_565 ? C8 H81 0.97(2) . ? C8 H82 0.98(3) . ? C8 H83 1.01(2) . ? 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 O22 K1 O21 111.07(4) 1_565 . ? O22 K1 O31 93.99(4) 1_565 2_565 ? O21 K1 O31 97.48(5) . 2_565 ? O22 K1 O21 84.32(4) 1_565 2_665 ? O21 K1 O21 80.73(5) . 2_665 ? O31 K1 O21 176.89(3) 2_565 2_665 ? O22 K1 O11 106.41(4) 1_565 2_665 ? O21 K1 O11 113.53(4) . 2_665 ? O31 K1 O11 132.31(4) 2_565 2_665 ? O21 K1 O11 50.79(4) 2_665 2_665 ? O22 K1 O8 168.28(4) 1_565 2_565 ? O21 K1 O8 70.84(4) . 2_565 ? O31 K1 O8 74.29(4) 2_565 2_565 ? O21 K1 O8 107.35(4) 2_665 2_565 ? O11 K1 O8 82.53(4) 2_665 2_565 ? O22 K1 O7 65.40(4) 1_565 2_665 ? O21 K1 O7 163.24(4) . 2_665 ? O31 K1 O7 67.15(4) 2_565 2_665 ? O21 K1 O7 114.30(4) 2_665 2_665 ? O11 K1 O7 82.76(5) 2_665 2_665 ? O8 K1 O7 109.24(4) 2_565 2_665 ? O32 K2 O22 173.24(4) 2 2_655 ? O32 K2 O21 95.17(5) 2 . ? O22 K2 O21 83.45(4) 2_655 . ? O32 K2 O12 135.20(4) 2 2_655 ? O22 K2 O12 51.08(4) 2_655 2_655 ? O21 K2 O12 109.72(4) . 2_655 ? O32 K2 O22 93.31(5) 2 . ? O22 K2 O22 82.09(5) 2_655 . ? O21 K2 O22 124.13(4) . . ? O12 K2 O22 101.78(4) 2_655 . ? O32 K2 O8 73.65(5) 2 2_565 ? O22 K2 O8 111.83(5) 2_655 2_565 ? O21 K2 O8 69.66(4) . 2_565 ? O12 K2 O8 80.80(5) 2_655 2_565 ? O22 K2 O8 162.58(3) . 2_565 ? O32 K2 O42 73.02(4) 2 . ? O22 K2 O42 100.22(4) 2_655 . ? O21 K2 O42 79.34(4) . . ? O12 K2 O42 146.27(4) 2_655 . ? O22 K2 O42 51.11(4) . . ? O8 K2 O42 131.47(4) 2_565 . ? O32 K2 O7 69.64(4) 2 2_655 ? O22 K2 O7 111.87(4) 2_655 2_655 ? O21 K2 O7 164.68(4) . 2_655 ? O12 K2 O7 81.39(4) 2_655 2_655 ? O22 K2 O7 60.93(4) . 2_655 ? O8 K2 O7 102.95(4) 2_565 2_655 ? O42 K2 O7 97.33(4) . 2_655 ? O21 P1 O41 120.15(7) . . ? O21 P1 O31 114.02(7) . . ? O41 P1 O31 105.47(7) . . ? O21 P1 O11 102.80(7) . . ? O41 P1 O11 108.13(7) . . ? O31 P1 O11 105.22(7) . . ? C11 O11 P1 126.08(10) . . ? C11 O11 K1 129.62(9) . 2_665 ? K1 O21 K2 110.60(4) . . ? K1 O21 K1 99.27(5) . 2_665 ? K2 O21 K1 94.22(4) . 2_665 ? O11 C11 C21 115.51(14) . . ? O11 C11 C61 123.52(14) . . ? C21 C11 C61 120.95(14) . . ? C31 C21 C11 119.87(15) . . ? C31 C21 H21 122.3(13) . . ? C11 C21 H21 117.8(13) . . ? C41 C31 C21 118.56(15) . . ? C41 C31 H31 120.5(13) . . ? C21 C31 H31 120.9(13) . . ? C51 C41 C31 122.65(15) . . ? C51 C41 N1 118.74(15) . . ? C31 C41 N1 118.60(15) . . ? C41 C51 C61 118.47(15) . . ? C41 C51 H51 119.3(11) . . ? C61 C51 H51 122.2(11) . . ? C11 C61 C51 119.49(15) . . ? C11 C61 H61 121.2(14) . . ? C51 C61 H61 119.3(14) . . ? O51 N1 O61 123.79(15) . . ? O51 N1 C41 118.10(15) . . ? O61 N1 C41 118.10(14) . . ? O22 P2 O42 117.98(7) . . ? O22 P2 O32 114.21(7) . . ? O42 P2 O32 105.93(7) . . ? O22 P2 O12 102.95(7) . . ? O42 P2 O12 110.28(7) . . ? O32 P2 O12 104.72(7) . . ? C12 O12 P2 122.60(10) . . ? P2 O32 H3O2 113(2) . . ? K1 O22 K2 98.00(5) 1_545 2_655 ? K1 O22 K2 124.54(4) 1_545 . ? K2 O22 K2 97.91(5) 2_655 . ? C22 C12 C62 121.87(15) . . ? C22 C12 O12 118.15(14) . . ? C62 C12 O12 119.86(14) . . ? C12 C62 C52 119.12(16) . . ? C12 C62 H62 118.3(12) . . ? C52 C62 H62 122.5(12) . . ? C42 C52 C62 118.28(16) . . ? C42 C52 H52 120.1(14) . . ? C62 C52 H52 121.6(14) . . ? C32 C42 C52 122.73(15) . . ? C32 C42 N2 118.25(16) . . ? C52 C42 N2 119.00(16) . . ? C42 C32 C22 118.80(16) . . ? C42 C32 H32 118.3(15) . . ? C22 C32 H32 122.8(15) . . ? C12 C22 C32 119.19(16) . . ? C12 C22 H22 118.3(13) . . ? C32 C22 H22 122.5(13) . . ? O52 N2 O62 123.41(16) . . ? O52 N2 C42 118.47(16) . . ? O62 N2 C42 118.11(17) . . ? K1 O7 K2 106.28(4) 2_665 2_655 ? C7 O7 H7 107.3(17) . . ? O7 C7 H71 110.1(14) . . ? O7 C7 H72 113.1(17) . . ? H71 C7 H72 111(2) . . ? O7 C7 H73 110.9(17) . . ? H71 C7 H73 105(2) . . ? H72 C7 H73 107(2) . . ? K1 O8 K2 105.84(4) 2_565 2_565 ? C8 O8 H8 108.3(17) . . ? O8 C8 H81 110.4(13) . . ? O8 C8 H82 109.9(16) . . ? H81 C8 H82 110(2) . . ? O8 C8 H83 107.7(12) . . ? H81 C8 H83 107.7(18) . . ? H82 C8 H83 111(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O21 P1 O11 C11 169.78(12) . . . . ? O31 P1 O11 C11 -70.60(13) . . . . ? O41 P1 O11 C11 41.73(14) . . . . ? P1 O11 C11 C21 -158.73(12) . . . . ? P1 O11 C11 C61 22.9(2) . . . . ? O11 C11 C21 C31 -178.23(15) . . . . ? O11 C11 C61 C51 178.60(15) . . . . ? N1 C41 C31 C21 -179.87(16) . . . . ? N1 C41 C51 C61 -179.63(15) . . . . ? C31 C41 N1 O51 -8.1(2) . . . . ? C51 C41 N1 O51 171.65(16) . . . . ? C31 C41 N1 O61 170.87(17) . . . . ? C51 C41 N1 O61 -9.4(2) . . . . ? C61 C11 C21 C31 0.1(2) . . . . ? C11 C21 C31 C41 -0.5(3) . . . . ? C21 C31 C41 C51 0.4(3) . . . . ? C31 C41 C51 C61 0.1(3) . . . . ? O22 P2 O12 C12 173.60(11) . . . . ? O32 P2 O12 C12 -66.70(13) . . . . ? O42 P2 O12 C12 46.86(13) . . . . ? P2 O12 C12 C22 -96.12(15) . . . . ? P2 O12 C12 C62 87.66(16) . . . . ? O12 C12 C22 C32 -175.73(14) . . . . ? O12 C12 C62 C52 176.51(14) . . . . ? N2 C42 C32 C22 178.66(15) . . . . ? N2 C42 C52 C62 -177.80(15) . . . . ? C32 C42 N2 O52 0.4(2) . . . . ? C52 C42 N2 O52 178.72(17) . . . . ? C32 C42 N2 O62 -178.96(16) . . . . ? C52 C42 N2 O62 -0.6(2) . . . . ? C62 C12 C22 C32 0.4(2) . . . . ? C12 C22 C32 C42 -0.8(2) . . . . ? C22 C32 C42 C52 0.4(3) . . . . ? C32 C42 C52 C62 0.5(3) . . . . ? 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 O31 H3O1 O42 0.77(3) 1.74(3) 2.4990(18) 169(3) . O32 H3O2 O41 0.77(3) 1.74(3) 2.4968(18) 167(3) 1_545 O7 H7 O42 0.79(2) 2.21(3) 2.970(2) 162(2) 1_655 O8 H8 O41 0.79(2) 1.98(3) 2.765(2) 172(2) . C22 H22 O7 0.95(2) 2.73(2) 3.497(3) 138.4(17) . C31 H31 O62 0.94(2) 2.61(2) 3.370(3) 138.2(18) 2_656 C51 H51 O61 0.96(2) 2.62(2) 3.310(3) 129.1(15) 2_566 C51 H51 O62 0.96(2) 2.625(19) 3.281(3) 126.0(15) 2_556 C52 H52 O61 0.92(2) 2.58(2) 3.425(3) 152.7(18) 2_556 C31 H31 O51 0.94(2) 2.43(2) 2.715(2) 97.7(15) . C32 H32 O52 0.94(3) 2.38(2) 2.714(2) 100.6(17) . C51 H51 O61 0.96(2) 2.410(19) 2.721(2) 98.4(13) . C52 H52 O62 0.92(2) 2.43(2) 2.726(2) 98.7(16) . _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.602 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.073 # Attachment 'CCDC279863.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 279863' _audit_creation_method SHELXL-97 _chemical_name_systematic ; POTASSIUM 4-NITROPHENYL HYDROGEN PHOSPHATE DIHYRATE ; _chemical_name_common 'POTASSIUM 4-NITROPHENYL HYDROGEN PHOSPHATE DIHYRATE' _chemical_formula_moiety 'C6 H9 K N O8 P' _chemical_formula_sum 'C6 H9 K N O8 P' _chemical_formula_weight 293.21 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' K K 0.2009 0.2494 '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 12.580(3) _cell_length_b 6.743(2) _cell_length_c 13.316(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.89(3) _cell_angle_gamma 90.00 _cell_volume 1127.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13685 _cell_measurement_theta_min 3 _cell_measurement_theta_max 33 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.728 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.644 _exptl_absorpt_correction_type ANALYTICAL _exptl_absorpt_correction_T_min 0.848 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_process_details ; XPREP-Brucker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'KUMA KM4CCD \k-geometry diffractometr' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15894 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 33.00 _reflns_number_total 4149 _reflns_number_gt 3652 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0386P)^2^+0.0996P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4149 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.003 _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 K K 0.900095(17) 0.83834(3) 0.564855(15) 0.01243(5) Uani 1 1 d . . . P P 0.181968(19) 0.52253(3) 0.231306(17) 0.00816(6) Uani 1 1 d . . . O1 O 0.29607(6) 0.41296(11) 0.25927(5) 0.01253(13) Uani 1 1 d . . . O2 O 0.13455(6) 0.37709(11) 0.14807(5) 0.01139(13) Uani 1 1 d . . . H2O H 0.1199(17) 0.272(3) 0.1748(16) 0.054(6) Uiso 1 1 d . . . O3 O 0.11949(6) 0.51388(10) 0.32350(5) 0.01161(13) Uani 1 1 d . . . O4 O 0.20006(6) 0.72023(10) 0.18510(5) 0.01240(13) Uani 1 1 d . . . C1 C 0.38119(7) 0.49383(14) 0.31397(7) 0.00995(15) Uani 1 1 d . . . C2 C 0.47286(7) 0.37523(14) 0.32130(7) 0.01130(16) Uani 1 1 d . . . H2 H 0.4682(12) 0.246(2) 0.2909(12) 0.022(4) Uiso 1 1 d . . . C3 C 0.56625(8) 0.44559(14) 0.36996(7) 0.01175(16) Uani 1 1 d . . . H3 H 0.6284(13) 0.371(2) 0.3726(12) 0.022(4) Uiso 1 1 d . . . C4 C 0.56488(7) 0.63333(14) 0.41323(7) 0.01114(16) Uani 1 1 d . . . C5 C 0.47346(8) 0.74996(15) 0.41000(7) 0.01207(16) Uani 1 1 d . . . H5 H 0.4740(13) 0.872(2) 0.4426(12) 0.021(4) Uiso 1 1 d . . . C6 C 0.38043(8) 0.67959(14) 0.36004(7) 0.01176(16) Uani 1 1 d . . . H6 H 0.3179(12) 0.763(2) 0.3551(11) 0.016(3) Uiso 1 1 d . . . N N 0.66250(7) 0.70668(13) 0.46537(6) 0.01275(15) Uani 1 1 d . . . O5 O 0.74047(6) 0.59599(12) 0.47247(6) 0.01686(15) Uani 1 1 d . . . O6 O 0.66364(7) 0.87549(12) 0.50160(6) 0.01990(16) Uani 1 1 d . . . O1W O 0.09148(6) 1.04715(11) 0.23070(6) 0.01331(13) Uani 1 1 d . . . H11 H 0.0226(15) 1.022(3) 0.2148(13) 0.031(4) Uiso 1 1 d . . . H21 H 0.1280(16) 0.943(3) 0.2147(14) 0.042(5) Uiso 1 1 d . . . O2W O 0.09555(6) 0.76765(12) 0.48782(6) 0.01581(14) Uani 1 1 d . . . H12 H 0.1380(15) 0.754(3) 0.5341(14) 0.034(5) Uiso 1 1 d . . . H22 H 0.1084(14) 0.685(3) 0.4410(14) 0.034(5) 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 K 0.01373(9) 0.01296(9) 0.01049(9) 0.00118(6) 0.00002(7) -0.00122(7) P 0.00823(10) 0.00831(10) 0.00778(10) -0.00004(7) -0.00063(7) -0.00024(7) O1 0.0094(3) 0.0117(3) 0.0159(3) -0.0029(2) -0.0026(2) 0.0006(2) O2 0.0139(3) 0.0113(3) 0.0087(3) -0.0011(2) -0.0009(2) -0.0026(2) O3 0.0122(3) 0.0134(3) 0.0093(3) -0.0008(2) 0.0012(2) -0.0003(2) O4 0.0146(3) 0.0098(3) 0.0126(3) 0.0015(2) 0.0000(2) -0.0011(2) C1 0.0092(4) 0.0119(4) 0.0087(4) 0.0002(3) 0.0002(3) -0.0004(3) C2 0.0104(4) 0.0126(4) 0.0108(4) -0.0011(3) 0.0001(3) 0.0011(3) C3 0.0102(4) 0.0146(4) 0.0103(4) 0.0000(3) -0.0001(3) 0.0013(3) C4 0.0093(4) 0.0145(4) 0.0095(4) 0.0000(3) -0.0006(3) -0.0019(3) C5 0.0116(4) 0.0129(4) 0.0116(4) -0.0025(3) -0.0001(3) 0.0000(3) C6 0.0104(4) 0.0128(4) 0.0119(4) -0.0019(3) -0.0001(3) 0.0010(3) N 0.0115(4) 0.0171(4) 0.0095(3) 0.0006(3) -0.0004(3) -0.0024(3) O5 0.0108(3) 0.0195(4) 0.0197(3) 0.0035(3) -0.0037(3) 0.0003(3) O6 0.0164(4) 0.0198(4) 0.0231(4) -0.0088(3) -0.0015(3) -0.0026(3) O1W 0.0129(3) 0.0110(3) 0.0160(3) -0.0016(2) 0.0002(3) -0.0005(2) O2W 0.0178(4) 0.0164(3) 0.0127(3) -0.0033(3) -0.0028(3) 0.0036(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 K O2W 2.7493(11) 3_676 ? K O2W 2.7691(11) 1_655 ? K O5 2.8073(10) . ? K O3 2.8216(10) 3_666 ? K O1W 2.8248(10) 3_676 ? K O2 2.8512(10) 2_655 ? K O6 3.0464(12) . ? K N 3.3075(12) . ? K K 3.8267(9) 3_776 ? P O4 1.4922(8) . ? P O3 1.5031(8) . ? P O2 1.5674(8) . ? P O1 1.6348(8) . ? O1 C1 1.3669(12) . ? O2 H2O 0.82(2) . ? C1 C6 1.3951(13) . ? C1 C2 1.4014(13) . ? C2 C3 1.3863(14) . ? C2 H2 0.963(16) . ? C3 C4 1.3914(14) . ? C3 H3 0.927(16) . ? C4 C5 1.3915(14) . ? C4 N 1.4557(13) . ? C5 C6 1.3899(14) . ? C5 H5 0.929(15) . ? C6 H6 0.967(15) . ? N O5 1.2311(12) . ? N O6 1.2360(12) . ? O1W H11 0.894(19) . ? O1W H21 0.87(2) . ? O2W H12 0.79(2) . ? O2W H22 0.860(19) . ? 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 O2W K O2W 92.19(3) 3_676 1_655 ? O2W K O5 118.47(3) 3_676 . ? O2W K O5 111.36(3) 1_655 . ? O2W K O3 162.14(2) 3_676 3_666 ? O2W K O3 99.31(3) 1_655 3_666 ? O5 K O3 69.85(3) . 3_666 ? O2W K O1W 88.95(3) 3_676 3_676 ? O2W K O1W 115.33(3) 1_655 3_676 ? O5 K O1W 124.08(3) . 3_676 ? O3 K O1W 73.81(3) 3_666 3_676 ? O2W K O2 70.25(2) 3_676 2_655 ? O2W K O2 74.16(3) 1_655 2_655 ? O5 K O2 63.96(3) . 2_655 ? O3 K O2 126.03(2) 3_666 2_655 ? O1W K O2 157.90(2) 3_676 2_655 ? O2W K O6 83.45(2) 3_676 . ? O2W K O6 141.87(3) 1_655 . ? O5 K O6 43.17(3) . . ? O3 K O6 95.53(3) 3_666 . ? O1W K O6 102.48(4) 3_676 . ? O2 K O6 68.72(4) 2_655 . ? O4 P O3 118.32(4) . . ? O4 P O2 109.20(4) . . ? O3 P O2 110.99(4) . . ? O4 P O1 109.97(4) . . ? O3 P O1 107.23(4) . . ? O2 P O1 99.46(4) . . ? C1 O1 P 125.80(7) . . ? P O2 K 141.79(4) . 2_645 ? P O2 H2O 108.7(15) . . ? P O3 K 122.16(4) . 3_666 ? O1 C1 C6 124.33(8) . . ? O1 C1 C2 114.88(8) . . ? C6 C1 C2 120.79(9) . . ? C3 C2 C1 120.30(9) . . ? C3 C2 H2 122.2(9) . . ? C1 C2 H2 117.5(9) . . ? C2 C3 C4 118.10(9) . . ? C2 C3 H3 121.2(10) . . ? C4 C3 H3 120.7(10) . . ? C3 C4 C5 122.33(9) . . ? C3 C4 N 118.22(8) . . ? C5 C4 N 119.44(9) . . ? C6 C5 C4 119.29(9) . . ? C6 C5 H5 120.3(10) . . ? C4 C5 H5 120.4(10) . . ? C5 C6 C1 119.10(9) . . ? C5 C6 H6 119.2(9) . . ? C1 C6 H6 121.6(9) . . ? O5 N O6 122.71(9) . . ? O5 N C4 118.20(9) . . ? O6 N C4 119.08(8) . . ? N O5 K 102.90(6) . . ? N O6 K 91.00(6) . . ? H11 O1W H21 108.1(17) . . ? K O2W K 87.81(2) 3_676 1_455 ? H12 O2W H22 109.7(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P O1 C1 166.24(8) . . . . ? O3 P O1 C1 -78.17(8) . . . . ? O4 P O1 C1 51.71(9) . . . . ? P O1 C1 C2 -175.44(7) . . . . ? P O1 C1 C6 4.45(13) . . . . ? O1 C1 C2 C3 176.33(8) . . . . ? O1 C1 C6 C5 -177.15(9) . . . . ? N C4 C3 C2 179.32(9) . . . . ? N C4 C5 C6 179.91(9) . . . . ? C3 C4 N O5 -3.03(13) . . . . ? C5 C4 N O5 175.66(9) . . . . ? C3 C4 N O6 177.82(9) . . . . ? C5 C4 N O6 -3.49(13) . . . . ? C6 C1 C2 C3 -3.56(14) . . . . ? C1 C2 C3 C4 1.82(14) . . . . ? C2 C3 C4 C5 0.67(14) . . . . ? C3 C4 C5 C6 -1.46(15) . . . . ? H2O O2 P O1 69.8(16) . . . . ? 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 O2 H2O O1W 0.82(2) 1.74(2) 2.5564(12) 179(2) 1_545 O1W H11 O3 0.894(19) 1.826(19) 2.7120(13) 170.8(16) 2 O1W H21 O4 0.87(2) 1.81(2) 2.6845(12) 177.3(19) . O2W H12 O4 0.79(2) 2.11(2) 2.8578(14) 156.2(18) 4_576 O2W H22 O3 0.860(19) 1.956(19) 2.8100(12) 171.6(18) . C3 H3 O4 0.927(16) 2.552(16) 3.4325(14) 158.8(13) 2_645 C5 H5 O6 0.929(15) 2.574(16) 3.3188(14) 137.5(13) 3_676 C3 H3 O5 0.927(16) 2.409(16) 2.6999(14) 98.1(11) . C5 H5 O6 0.929(15) 2.461(16) 2.7445(14) 97.7(11) . _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 33.00 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.478 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.063 # Attachment 'CCDC279864.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 279864' _audit_creation_method SHELXL-97 _chemical_name_systematic ; DIPOTASSIUM 4-NITROPHENYL PHOSPHATE TETRAHYDRATE ; _chemical_name_common 'DIPOTASSIUM 4-NITROPHENYL PHOSPHATE TETRAHYDRATE' _chemical_formula_moiety 'C6 H12 K2 N O10 P' _chemical_formula_sum 'C6 H12 K2 N O10 P' _chemical_formula_weight 367.34 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' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ORTHORHOMBIC _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.529(4) _cell_length_b 7.131(3) _cell_length_c 31.914(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2851.3(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8608 _cell_measurement_theta_min 3.29 _cell_measurement_theta_max 29 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.711 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1504 _exptl_absorpt_coefficient_mu 0.822 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.764 _exptl_absorpt_correction_T_max 0.957 _exptl_absorpt_process_details ; XPREP-Brucker Analytical X-ray Systems, 1997 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'KUMA KM4CCD \k-geometry diffractometr' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23007 _diffrn_reflns_av_R_equivalents 0.0783 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 29.00 _reflns_number_total 3667 _reflns_number_gt 2811 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD (Oxford Diffraction, Poland Sp. z o.o)' _computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_data_reduction 'CrysAlis RED (Oxford Diffraction, Poland Sp. z o.o)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-NT V5.1, Bruker AXS 1999' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0531P)^2^+1.0047P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3667 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1168 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 K1 K 0.38225(5) 0.68878(7) 0.291907(17) 0.01635(15) Uani 1 1 d . . . K2 K 0.74104(5) 0.67451(7) 0.330475(17) 0.01723(15) Uani 1 1 d . . . P P 0.11329(6) 0.67977(9) 0.32176(2) 0.01371(16) Uani 1 1 d . . . O1 O 0.21758(15) 0.6882(3) 0.35388(5) 0.0169(4) Uani 1 1 d . . . O2 O 0.16927(16) 0.6612(2) 0.28010(6) 0.0174(4) Uani 1 1 d . . . O3 O 0.04978(15) 0.5082(2) 0.33363(6) 0.0182(4) Uani 1 1 d . . . O4 O 0.05414(15) 0.8632(2) 0.32710(6) 0.0162(4) Uani 1 1 d . . . C1 C 0.2133(2) 0.7337(3) 0.39531(8) 0.0163(6) Uani 1 1 d . . . C2 C 0.3113(3) 0.7623(4) 0.41507(10) 0.0242(7) Uani 1 1 d . . . H2 H 0.370(3) 0.748(5) 0.3975(11) 0.029 Uiso 1 1 d . . . C3 C 0.3137(3) 0.8142(4) 0.45679(10) 0.0314(8) Uani 1 1 d . . . H3 H 0.383(3) 0.832(5) 0.4678(12) 0.038 Uiso 1 1 d . . . C4 C 0.2188(3) 0.8371(4) 0.47811(9) 0.0331(8) Uani 1 1 d . . . C5 C 0.1216(3) 0.8045(4) 0.45954(9) 0.0307(8) Uani 1 1 d . . . H5 H 0.060(3) 0.823(5) 0.4752(11) 0.037 Uiso 1 1 d . . . C6 C 0.1185(3) 0.7508(4) 0.41789(9) 0.0230(6) Uani 1 1 d . . . H6 H 0.051(3) 0.725(4) 0.4048(10) 0.028 Uiso 1 1 d . . . N N 0.2205(4) 0.9027(4) 0.52151(9) 0.0478(10) Uani 1 1 d . . . O5 O 0.3090(3) 0.9265(4) 0.53798(8) 0.0637(9) Uani 1 1 d . . . O6 O 0.1351(3) 0.9335(4) 0.53929(8) 0.0632(10) Uani 1 1 d . . . O1W O 0.61649(18) 0.9143(3) 0.28111(7) 0.0193(4) Uani 1 1 d . . . H11 H 0.570(4) 0.949(6) 0.2987(14) 0.056(13) Uiso 1 1 d . . . H12 H 0.625(4) 0.987(7) 0.2616(17) 0.082(17) Uiso 1 1 d . . . O2W O 0.62322(19) 0.4364(3) 0.27737(7) 0.0202(4) Uani 1 1 d . . . H21 H 0.572(3) 0.407(5) 0.2913(11) 0.029(10) Uiso 1 1 d . . . H22 H 0.637(3) 0.359(5) 0.2595(12) 0.038(11) Uiso 1 1 d . . . O3W O 0.8753(2) 0.4123(3) 0.37927(8) 0.0265(5) Uani 1 1 d . . . H31 H 0.867(3) 0.437(6) 0.4021(14) 0.049(13) Uiso 1 1 d . . . H32 H 0.937(3) 0.442(5) 0.3702(11) 0.033(10) Uiso 1 1 d . . . O4W O 0.62470(19) 0.4091(3) 0.37481(7) 0.0219(5) Uani 1 1 d . . . H41 H 0.621(3) 0.440(5) 0.3956(12) 0.026(10) Uiso 1 1 d . . . H42 H 0.564(3) 0.403(5) 0.3625(13) 0.045(12) 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 K1 0.0177(3) 0.0144(3) 0.0170(3) -0.0002(2) 0.0005(2) -0.0006(2) K2 0.0196(3) 0.0121(2) 0.0200(3) -0.0006(2) -0.0007(2) 0.0001(2) P 0.0146(3) 0.0133(3) 0.0132(3) -0.0010(2) -0.0006(3) -0.0008(3) O1 0.0158(10) 0.0206(9) 0.0144(9) -0.0021(7) -0.0006(8) 0.0005(8) O2 0.0175(10) 0.0196(9) 0.0152(9) 0.0002(7) -0.0016(8) 0.0015(8) O3 0.0191(11) 0.0157(9) 0.0199(9) -0.0010(7) -0.0003(8) -0.0011(8) O4 0.0168(10) 0.0138(8) 0.0180(9) -0.0001(7) -0.0021(8) 0.0033(7) C1 0.0245(16) 0.0123(11) 0.0121(11) 0.0003(9) -0.0036(11) -0.0007(10) C2 0.0314(19) 0.0178(13) 0.0234(15) 0.0027(11) -0.0061(14) -0.0033(12) C3 0.048(2) 0.0204(14) 0.0262(15) 0.0033(12) -0.0153(16) -0.0103(15) C4 0.069(3) 0.0133(13) 0.0173(14) -0.0016(11) -0.0070(16) 0.0011(14) C5 0.054(2) 0.0194(14) 0.0182(14) 0.0018(12) 0.0023(15) 0.0093(15) C6 0.0318(19) 0.0193(13) 0.0179(13) 0.0008(11) 0.0007(14) 0.0020(12) N 0.098(3) 0.0234(14) 0.0217(15) -0.0029(11) -0.0145(19) 0.0024(16) O5 0.110(3) 0.0521(17) 0.0289(14) -0.0088(12) -0.0271(17) -0.0042(18) O6 0.112(3) 0.0574(18) 0.0203(12) -0.0132(12) 0.0023(16) 0.0219(18) O1W 0.0240(12) 0.0163(9) 0.0176(10) 0.0023(8) 0.0034(9) 0.0061(8) O2W 0.0240(13) 0.0193(10) 0.0172(10) -0.0017(8) 0.0028(9) -0.0039(9) O3W 0.0268(14) 0.0322(12) 0.0205(12) -0.0055(9) 0.0042(10) -0.0093(10) O4W 0.0197(13) 0.0301(11) 0.0159(11) -0.0052(9) -0.0004(10) -0.0037(9) _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 K1 O4 2.699(2) 8_655 ? K1 O2 2.702(2) . ? K1 O3 2.773(2) 8_665 ? K1 O1W 2.831(2) 3_655 ? K1 O2W 2.852(2) 3_655 ? K1 O1 2.858(2) . ? K1 O1W 3.364(3) . ? K2 O3W 2.725(2) 8_765 ? K2 O4W 2.762(2) 8_765 ? K2 O4W 2.776(2) . ? K2 O1W 2.800(2) . ? K2 O2W 2.817(2) . ? K2 O3W 2.958(3) . ? K2 O1W 3.018(2) 8_755 ? K2 O2W 3.042(2) 8_765 ? P O3 1.508(2) . ? P O2 1.509(2) . ? P O4 1.5133(19) . ? P O1 1.662(2) . ? O1 C1 1.362(3) . ? C1 C6 1.395(4) . ? C1 C2 1.395(4) . ? C2 C3 1.382(4) . ? C2 H2 0.93(4) . ? C3 C4 1.380(5) . ? C3 H3 0.95(4) . ? C4 C5 1.374(5) . ? C4 N 1.462(4) . ? C5 C6 1.384(4) . ? C5 H5 0.93(4) . ? C6 H6 0.96(4) . ? N O6 1.232(5) . ? N O5 1.239(5) . ? O1W H11 0.85(4) . ? O1W H12 0.82(5) . ? O2W H21 0.81(4) . ? O2W H22 0.81(4) . ? O3W H31 0.76(4) . ? O3W H32 0.85(4) . ? O4W H41 0.70(4) . ? O4W H42 0.86(4) . ? 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 K1 O2 106.68(6) 8_655 . ? O4 K1 O3 114.59(6) 8_655 8_665 ? O2 K1 O3 115.47(6) . 8_665 ? O4 K1 O1W 146.03(6) 8_655 3_655 ? O2 K1 O1W 86.10(6) . 3_655 ? O3 K1 O1W 85.81(6) 8_665 3_655 ? O4 K1 O2W 77.70(6) 8_655 3_655 ? O2 K1 O2W 79.76(6) . 3_655 ? O3 K1 O2W 153.93(7) 8_665 3_655 ? O1W K1 O2W 73.77(7) 3_655 3_655 ? O4 K1 O1 85.64(6) 8_655 . ? O2 K1 O1 51.94(6) . . ? O3 K1 O1 83.71(6) 8_665 . ? O1W K1 O1 125.05(6) 3_655 . ? O2W K1 O1 121.22(6) 3_655 . ? O4 K1 O1W 101.31(6) 8_655 . ? O2 K1 O1W 151.88(5) . . ? O3 K1 O1W 52.30(5) 8_665 . ? O1W K1 O1W 68.86(7) 3_655 . ? O2W K1 O1W 104.08(6) 3_655 . ? O1 K1 O1W 134.52(6) . . ? O3W K2 O4W 69.90(8) 8_765 8_765 ? O3W K2 O4W 81.50(7) 8_765 . ? O4W K2 O4W 118.13(10) 8_765 . ? O3W K2 O1W 69.10(7) 8_765 . ? O4W K2 O1W 104.93(7) 8_765 . ? O4W K2 O1W 114.23(8) . . ? O3W K2 O2W 116.01(8) 8_765 . ? O4W K2 O2W 172.93(7) 8_765 . ? O4W K2 O2W 67.70(7) . . ? O1W K2 O2W 74.78(7) . . ? O3W K2 O3W 113.38(10) 8_765 . ? O4W K2 O3W 76.51(7) 8_765 . ? O4W K2 O3W 66.39(7) . . ? O1W K2 O3W 177.50(7) . . ? O2W K2 O3W 103.52(7) . . ? O3W K2 O1W 175.68(7) 8_765 8_755 ? O4W K2 O1W 106.23(7) 8_765 8_755 ? O4W K2 O1W 99.06(7) . 8_755 ? O1W K2 O1W 114.29(8) . 8_755 ? O2W K2 O1W 68.00(7) . 8_755 ? O3W K2 O1W 63.25(7) . 8_755 ? O3W K2 O2W 103.61(7) 8_765 8_765 ? O4W K2 O2W 64.73(7) 8_765 8_765 ? O4W K2 O2W 174.87(6) . 8_765 ? O1W K2 O2W 67.86(7) . 8_765 ? O2W K2 O2W 109.14(9) . 8_765 ? O3W K2 O2W 111.31(7) . 8_765 ? O1W K2 O2W 75.88(6) 8_755 8_765 ? O3 P O2 113.31(11) . . ? O3 P O4 114.50(11) . . ? O2 P O4 113.74(10) . . ? O3 P O1 106.83(10) . . ? O2 P O1 100.44(11) . . ? O4 P O1 106.51(10) . . ? C1 O1 P 125.20(18) . . ? O1 C1 C6 123.8(3) . . ? O1 C1 C2 116.0(3) . . ? C6 C1 C2 120.2(3) . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2 126(2) . . ? C1 C2 H2 114(2) . . ? C4 C3 C2 119.2(3) . . ? C4 C3 H3 127(2) . . ? C2 C3 H3 114(2) . . ? C5 C4 C3 122.1(3) . . ? C5 C4 N 118.4(3) . . ? C3 C4 N 119.5(3) . . ? C4 C5 C6 119.1(3) . . ? C4 C5 H5 119(2) . . ? C6 C5 H5 122(2) . . ? C5 C6 C1 119.8(3) . . ? C5 C6 H6 120(2) . . ? C1 C6 H6 121(2) . . ? O6 N O5 123.9(3) . . ? O6 N C4 118.7(4) . . ? O5 N C4 117.4(4) . . ? K2 O1W K1 96.49(6) . 3_655 ? K2 O1W K2 75.65(6) . 8_765 ? K1 O1W K2 140.84(9) 3_655 8_765 ? K2 O1W K1 97.85(7) . . ? K1 O1W K1 79.49(5) 3_655 . ? K2 O1W K1 139.14(8) 8_765 . ? H11 O1W H12 114(4) . . ? K2 O2W K1 95.67(7) . 3_655 ? K2 O2W K2 75.04(6) . 8_755 ? K1 O2W K2 146.40(9) 3_655 8_755 ? H21 O2W H22 112(4) . . ? K2 O3W K2 77.77(7) 8_755 . ? H31 O3W H32 113(4) . . ? K2 O4W K2 80.33(6) 8_755 . ? H41 O4W H42 113(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P O1 C1 169.32(19) . . . . ? O3 P O1 C1 -72.3(2) . . . . ? O4 P O1 C1 50.5(2) . . . . ? P O1 C1 C2 -169.97(18) . . . . ? P O1 C1 C6 10.5(3) . . . . ? O1 C1 C2 C3 178.1(2) . . . . ? O1 C1 C6 C5 -177.6(2) . . . . ? N C4 C3 C2 -176.4(3) . . . . ? N C4 C5 C6 177.0(3) . . . . ? C3 C4 N O5 -3.4(4) . . . . ? C5 C4 N O5 178.2(3) . . . . ? C3 C4 N O6 175.6(3) . . . . ? C5 C4 N O6 -2.9(4) . . . . ? C6 C1 C2 C3 -2.3(4) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C2 C3 C4 C5 2.0(4) . . . . ? C3 C4 C5 C6 -1.4(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 O1W H11 O3 0.85(4) 1.91(5) 2.756(3) 172(4) 8_665 O1W H12 O2 0.82(5) 1.90(5) 2.712(3) 170(5) 6_666 O2W H21 O4 0.81(4) 1.98(4) 2.780(3) 174(4) 8_655 O2W H22 O2 0.81(4) 1.93(4) 2.747(3) 176(4) 6_656 O3W H31 O5 0.76(4) 2.26(4) 2.998(4) 163(4) 4_566 O3W H32 O3 0.85(4) 1.89(4) 2.714(3) 161(3) 1_655 O4W H41 O6 0.70(4) 2.27(4) 2.965(3) 171(4) 4_566 O4W H42 O4 0.86(4) 1.88(4) 2.729(3) 168(4) 8_655 C5 H5 O6 0.93(4) 2.39(4) 2.712(4) 100(3) . _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 29.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.480 _refine_diff_density_min -0.712 _refine_diff_density_rms 0.091