# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Annie Powell' _publ_contact_author_email POWELL@AOC.UNI-KARLSRUHE.DE _publ_section_title ; Photo- and Thermally-Enhanced Charge Separation in Supramolecular Viologen-Hexacyanoferrate Complexes ; loop_ _publ_author_name 'Annie Powell' 'Ahmed S. Abouelwafa' 'Christopher E. Anson' 'Teodor S. Balaban' 'Valeriu Mereacre' # Attachment 'viologen.cif' data_v1a _database_code_depnum_ccdc_archive 'CCDC 692001' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C22 H14 N6 O8), (C6 Fe N6), 20(H2 O)' _chemical_formula_sum 'C50 H68 Fe N18 O36' _chemical_formula_weight 1553.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'I b a m' _symmetry_space_group_name_Hall '-I 2 2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1, y+1, -z+1/2' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x, -y, z+1/2' '-x, y, z+1/2' _cell_length_a 26.3998(15) _cell_length_b 11.3528(6) _cell_length_c 22.2355(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6664.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8752 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.13 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 0.338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.845 _exptl_absorpt_correction_T_max 0.951 _exptl_absorpt_process_details 'SADABS (Bruker AXS Inc., 2000)' _exptl_special_details ; The crystal used had been freshly prepared and grown in the dark. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex' _diffrn_measurement_method 'CCD area detector' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22965 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0162 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 28.13 _reflns_number_total 3955 _reflns_number_gt 3343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_cell_refinement 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_data_reduction 'SAINT+ 6.0 (Bruker AXS Inc., 2000)' _computing_structure_solution 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS Inc., 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. Unlike most atoms of the viologen molecule, the thermal parameters of the atoms of the hexacyanometallate complex anion are markedly anisotropic, suggesting unresolved disorder between two closely separated sites. Attempts to resolve this disorder, or twinned refinements of the structure in lower-symmetry space groups, did not improve the structure. Some of the of the lattice water molecules, those corresponding to O(15), O(16) and O(17), were disordered over two or more sites. The H-atoms bonded to O(11) and O(12) were located and refined with restraints on the O-H distances. ; _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^)+(0.0986P)^2^+27.7600P] 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 3955 _refine_ls_number_parameters 267 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.2023 _refine_ls_wR_factor_gt 0.1928 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.992 _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 Fe1 Fe 0.5000 0.5000 0.5000 0.0578(4) Uani 1 4 d S . . C1 C 0.5000 0.5000 0.4141(2) 0.0470(11) Uani 1 2 d S . . N1 N 0.5000 0.5000 0.36180(16) 0.0407(8) Uani 1 2 d S . . C2 C 0.4348(2) 0.4280(5) 0.5000 0.0580(15) Uani 1 2 d S . . N2 N 0.39496(19) 0.3830(4) 0.5000 0.0571(12) Uani 1 2 d S . . C3 C 0.4691(3) 0.6509(7) 0.5000 0.067(2) Uani 1 2 d S . . N3 N 0.4498(2) 0.7426(6) 0.5000 0.0747(19) Uani 1 2 d S . . C4 C 0.45500(12) 0.7536(3) 0.33823(18) 0.0449(8) Uani 1 1 d . . . H4A H 0.4631 0.6742 0.3287 0.054 Uiso 1 1 calc R . . C5 C 0.49226(11) 0.8374(3) 0.33899(19) 0.0471(8) Uani 1 1 d . . . H5A H 0.5263 0.8162 0.3303 0.057 Uiso 1 1 calc R . . C6 C 0.48013(11) 0.9540(2) 0.35260(15) 0.0368(6) Uani 1 1 d . . . C7 C 0.43018(11) 0.9814(2) 0.36674(15) 0.0385(7) Uani 1 1 d . . . H7A H 0.4212 1.0598 0.3771 0.046 Uiso 1 1 calc R . . C8 C 0.39396(11) 0.8952(2) 0.36579(14) 0.0366(6) Uani 1 1 d . . . H8A H 0.3598 0.9136 0.3755 0.044 Uiso 1 1 calc R . . N4 N 0.40702(9) 0.7837(2) 0.35097(11) 0.0326(5) Uani 1 1 d . . . C9 C 0.36780(10) 0.6937(2) 0.34971(12) 0.0303(6) Uani 1 1 d . . . C10 C 0.33263(10) 0.6859(2) 0.30339(12) 0.0278(5) Uani 1 1 d . . . C11 C 0.29422(10) 0.6036(2) 0.30596(12) 0.0288(5) Uani 1 1 d . . . H11A H 0.2695 0.5988 0.2750 0.035 Uiso 1 1 calc R . . C12 C 0.29278(11) 0.5284(3) 0.35490(13) 0.0333(6) Uani 1 1 d . . . C13 C 0.32799(12) 0.5311(3) 0.40022(13) 0.0401(7) Uani 1 1 d . . . H13A H 0.3264 0.4770 0.4327 0.048 Uiso 1 1 calc R . . C14 C 0.36609(12) 0.6154(3) 0.39715(13) 0.0386(7) Uani 1 1 d . . . H14A H 0.3911 0.6192 0.4279 0.046 Uiso 1 1 calc R . . N5 N 0.33502(9) 0.7615(2) 0.24929(11) 0.0325(5) Uani 1 1 d . . . O1 O 0.36820(8) 0.83596(17) 0.24553(10) 0.0404(5) Uani 1 1 d . . . O2 O 0.30315(8) 0.7434(2) 0.21036(10) 0.0435(5) Uani 1 1 d . . . N6 N 0.25131(10) 0.4410(2) 0.35762(12) 0.0417(6) Uani 1 1 d . . . O3 O 0.22149(8) 0.4380(2) 0.31539(11) 0.0438(5) Uani 1 1 d . . . O4 O 0.24933(10) 0.3763(2) 0.40152(12) 0.0586(7) Uani 1 1 d . . . O11 O 0.38963(11) 0.2600(2) 0.38494(14) 0.0564(7) Uani 1 1 d D . . H111 H 0.396(2) 0.294(4) 0.4196(18) 0.085 Uiso 1 1 d D . . H112 H 0.3586(15) 0.217(4) 0.399(2) 0.085 Uiso 1 1 d D . . O12 O 0.42046(12) 0.4043(3) 0.28865(15) 0.0674(8) Uani 1 1 d D . . H121 H 0.4487(16) 0.434(5) 0.304(3) 0.101 Uiso 1 1 d D . . H122 H 0.408(2) 0.362(5) 0.322(2) 0.101 Uiso 1 1 d D . . O13 O 0.19285(13) 0.6106(4) 0.41707(16) 0.0885(12) Uani 1 1 d . . . O14 O 0.26540(17) 0.6945(4) 0.5000 0.0700(12) Uani 1 2 d S . . O15A O 0.3448(6) 0.8764(16) 0.5000 0.082(4) Uiso 0.34 2 d SP A 1 O17A O 0.3852(10) 1.106(2) 0.5000 0.137(8) Uiso 0.34 2 d SP B 1 O15B O 0.3560(3) 0.8179(7) 0.5000 0.0556(16) Uiso 0.56 2 d SP C 2 O17B O 0.3640(5) 1.0474(11) 0.5000 0.098(3) Uiso 0.56 2 d SP D 2 O15C O 0.3813(5) 0.9712(12) 0.5000 0.029(3) Uiso 0.20 2 d SP E 3 O16A O 0.4750(5) 1.0713(12) 0.5000 0.089(3) Uiso 0.50 2 d SP F 1 O16B O 0.4596(4) 1.1143(10) 0.5000 0.073(3) Uiso 0.50 2 d SP G 2 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 0.0707(7) 0.0837(8) 0.0191(4) 0.000 0.000 -0.0462(6) C1 0.055(3) 0.057(3) 0.030(2) 0.000 0.000 -0.024(2) N1 0.054(2) 0.0424(19) 0.0261(17) 0.000 0.000 -0.0081(17) C2 0.079(4) 0.077(4) 0.0180(19) 0.000 0.000 -0.034(3) N2 0.072(3) 0.071(3) 0.0289(18) 0.000 0.000 -0.036(3) C3 0.092(5) 0.086(4) 0.022(2) 0.000 0.000 -0.066(4) N3 0.094(4) 0.096(4) 0.034(2) 0.000 0.000 -0.067(4) C4 0.0375(15) 0.0221(12) 0.075(2) -0.0055(14) 0.0119(15) -0.0010(11) C5 0.0283(14) 0.0244(13) 0.089(3) -0.0001(15) 0.0100(15) 0.0012(11) C6 0.0308(13) 0.0249(12) 0.0547(18) -0.0014(12) -0.0002(12) -0.0037(12) C7 0.0333(14) 0.0261(14) 0.0562(18) -0.0131(12) 0.0030(13) -0.0010(11) C8 0.0302(13) 0.0300(13) 0.0496(17) -0.0121(12) 0.0061(12) -0.0020(11) N4 0.0300(11) 0.0256(11) 0.0423(13) -0.0068(9) 0.0054(9) -0.0058(9) C9 0.0303(13) 0.0267(12) 0.0338(13) -0.0084(10) 0.0086(10) -0.0078(10) C10 0.0309(12) 0.0234(11) 0.0291(12) -0.0023(10) 0.0082(10) 0.0018(10) C11 0.0279(12) 0.0282(12) 0.0303(12) -0.0050(10) 0.0046(10) -0.0015(10) C12 0.0340(14) 0.0351(14) 0.0307(13) -0.0032(11) 0.0069(11) -0.0105(11) C13 0.0474(17) 0.0457(17) 0.0271(13) 0.0011(12) 0.0047(12) -0.0178(13) C14 0.0427(15) 0.0452(16) 0.0278(13) -0.0053(12) 0.0002(11) -0.0141(13) N5 0.0340(11) 0.0279(11) 0.0357(12) 0.0009(9) 0.0080(10) 0.0046(9) O1 0.0465(12) 0.0272(10) 0.0475(12) 0.0034(9) 0.0104(10) -0.0052(9) O2 0.0401(11) 0.0480(13) 0.0423(12) 0.0089(10) -0.0002(9) 0.0011(10) N6 0.0397(13) 0.0446(14) 0.0409(14) -0.0005(11) 0.0076(11) -0.0156(11) O3 0.0361(11) 0.0475(13) 0.0479(13) -0.0075(10) 0.0013(9) -0.0150(10) O4 0.0551(14) 0.0623(16) 0.0583(15) 0.0200(13) 0.0037(12) -0.0256(13) O11 0.0607(15) 0.0411(13) 0.0673(17) -0.0135(12) -0.0146(13) -0.0008(11) O12 0.0658(18) 0.0665(18) 0.0699(19) -0.0261(15) -0.0018(15) -0.0247(15) O13 0.069(2) 0.130(3) 0.0658(19) -0.029(2) -0.0078(15) 0.037(2) O14 0.069(3) 0.087(3) 0.054(2) 0.000 0.000 -0.012(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 C3 1.897(9) 9_666 ? Fe1 C3 1.897(9) . ? Fe1 C2 1.906(5) 9_666 ? Fe1 C2 1.906(5) . ? Fe1 C1 1.910(4) . ? Fe1 C1 1.910(4) 9_666 ? C1 N1 1.163(6) . ? C2 N2 1.169(7) . ? C3 N3 1.159(10) . ? C4 N4 1.342(4) . ? C4 C5 1.369(4) . ? C4 H4A 0.9500 . ? C5 C6 1.395(4) . ? C5 H5A 0.9500 . ? C6 C7 1.391(4) . ? C6 C6 1.481(5) 2_675 ? C7 C8 1.368(4) . ? C7 H7A 0.9500 . ? C8 N4 1.353(4) . ? C8 H8A 0.9500 . ? N4 C9 1.455(3) . ? C9 C14 1.380(4) . ? C9 C10 1.390(4) . ? C10 C11 1.380(4) . ? C10 N5 1.479(3) . ? C11 C12 1.384(4) . ? C11 H11A 0.9500 . ? C12 C13 1.371(4) . ? C12 N6 1.479(4) . ? C13 C14 1.390(4) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? N5 O1 1.220(3) . ? N5 O2 1.224(3) . ? N6 O4 1.223(4) . ? N6 O3 1.226(4) . ? O11 H111 0.88(3) . ? O11 H112 1.01(3) . ? O12 H121 0.89(3) . ? O12 H122 0.94(3) . ? 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 C3 Fe1 C3 180.0 9_666 . ? C3 Fe1 C2 89.9(3) 9_666 9_666 ? C3 Fe1 C2 90.1(3) . 9_666 ? C3 Fe1 C2 90.1(3) 9_666 . ? C3 Fe1 C2 89.9(3) . . ? C2 Fe1 C2 180.0 9_666 . ? C3 Fe1 C1 90.0 9_666 . ? C3 Fe1 C1 90.0 . . ? C2 Fe1 C1 90.0 9_666 . ? C2 Fe1 C1 90.0 . . ? C3 Fe1 C1 90.0 9_666 9_666 ? C3 Fe1 C1 90.0 . 9_666 ? C2 Fe1 C1 90.0 9_666 9_666 ? C2 Fe1 C1 90.0 . 9_666 ? C1 Fe1 C1 180.0 . 9_666 ? N1 C1 Fe1 180.0 . . ? N2 C2 Fe1 179.5(6) . . ? N3 C3 Fe1 179.4(5) . . ? N4 C4 C5 119.9(3) . . ? N4 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5A 120.1 . . ? C6 C5 H5A 120.1 . . ? C7 C6 C5 118.6(3) . . ? C7 C6 C6 120.9(3) . 2_675 ? C5 C6 C6 120.4(3) . 2_675 ? C8 C7 C6 120.0(3) . . ? C8 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? N4 C8 C7 119.7(3) . . ? N4 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C4 N4 C8 122.0(2) . . ? C4 N4 C9 119.2(2) . . ? C8 N4 C9 118.7(2) . . ? C14 C9 C10 120.3(2) . . ? C14 C9 N4 117.4(3) . . ? C10 C9 N4 122.3(3) . . ? C11 C10 C9 120.2(2) . . ? C11 C10 N5 117.2(2) . . ? C9 C10 N5 122.5(2) . . ? C10 C11 C12 118.1(3) . . ? C10 C11 H11A 121.0 . . ? C12 C11 H11A 121.0 . . ? C13 C12 C11 123.1(3) . . ? C13 C12 N6 119.1(3) . . ? C11 C12 N6 117.8(3) . . ? C12 C13 C14 118.0(3) . . ? C12 C13 H13A 121.0 . . ? C14 C13 H13A 121.0 . . ? C9 C14 C13 120.3(3) . . ? C9 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? O1 N5 O2 124.1(3) . . ? O1 N5 C10 119.2(2) . . ? O2 N5 C10 116.7(2) . . ? O4 N6 O3 124.6(3) . . ? O4 N6 C12 117.9(3) . . ? O3 N6 C12 117.6(3) . . ? H111 O11 H112 96(5) . . ? H121 O12 H122 100(5) . . ? 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 N4 C4 C5 C6 -0.5(6) . . . . ? C4 C5 C6 C7 1.7(6) . . . . ? C4 C5 C6 C6 -179.0(3) . . . 2_675 ? C5 C6 C7 C8 -1.5(5) . . . . ? C6 C6 C7 C8 179.2(2) 2_675 . . . ? C6 C7 C8 N4 -0.1(5) . . . . ? C5 C4 N4 C8 -1.2(5) . . . . ? C5 C4 N4 C9 179.7(3) . . . . ? C7 C8 N4 C4 1.4(5) . . . . ? C7 C8 N4 C9 -179.4(3) . . . . ? C4 N4 C9 C14 75.3(4) . . . . ? C8 N4 C9 C14 -103.9(3) . . . . ? C4 N4 C9 C10 -105.5(4) . . . . ? C8 N4 C9 C10 75.4(4) . . . . ? C14 C9 C10 C11 3.2(4) . . . . ? N4 C9 C10 C11 -176.0(2) . . . . ? C14 C9 C10 N5 -175.3(2) . . . . ? N4 C9 C10 N5 5.6(4) . . . . ? C9 C10 C11 C12 -1.5(4) . . . . ? N5 C10 C11 C12 177.0(2) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C10 C11 C12 N6 179.6(2) . . . . ? C11 C12 C13 C14 1.5(5) . . . . ? N6 C12 C13 C14 -178.9(3) . . . . ? C10 C9 C14 C13 -2.5(4) . . . . ? N4 C9 C14 C13 176.7(3) . . . . ? C12 C13 C14 C9 0.2(5) . . . . ? C11 C10 N5 O1 179.4(2) . . . . ? C9 C10 N5 O1 -2.1(4) . . . . ? C11 C10 N5 O2 -1.3(3) . . . . ? C9 C10 N5 O2 177.1(2) . . . . ? C13 C12 N6 O4 2.1(4) . . . . ? C11 C12 N6 O4 -178.3(3) . . . . ? C13 C12 N6 O3 -177.5(3) . . . . ? C11 C12 N6 O3 2.1(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 O11 H111 N2 0.88(3) 2.05(4) 2.918(4) 167(5) . O11 H112 O13 1.01(3) 1.86(4) 2.851(4) 168(5) 12_655 O12 H121 N1 0.89(3) 2.01(4) 2.869(3) 163(6) . O12 H122 O11 0.94(3) 1.88(4) 2.816(5) 172(6) . C4 H4A N1 0.95 2.32 3.158(3) 146.2 . C13 H13A N2 0.95 2.58 3.298(5) 132.7 . C14 H14A N2 0.95 3.13 3.574(5) 110.7 . C14 H14A N3 0.95 2.63 3.492(5) 150.5 . C8 H8A O3 0.95 2.54 3.283(4) 134.9 12_665 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.819 _refine_diff_density_min -1.488 _refine_diff_density_rms 0.080 ############################################################# data_108 _database_code_depnum_ccdc_archive 'CCDC 692002' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C22 H14 N6 O8), (C6 Fe N6), 20(H2 O)' _chemical_formula_sum 'C50 H68 Fe N18 O36' _chemical_formula_weight 1553.07 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'I b a m' _symmetry_space_group_name_Hall '-I 2 2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' '-x+1, y+1, -z+1/2' 'x+1, -y+1, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x-1/2, -y-1/2, z' '-x-1/2, y-1/2, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' 'x, -y, z+1/2' '-x, y, z+1/2' _cell_length_a 26.442(3) _cell_length_b 11.3715(12) _cell_length_c 22.311(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6708.8(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8025 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.99 _exptl_crystal_description needle _exptl_crystal_colour green-black _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.538 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3232 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.948 _exptl_absorpt_correction_T_max 0.989 _exptl_absorpt_process_details 'SADABS (Bruker AXS Inc., 2000)' _exptl_special_details ; The crystal used had been irradiated with sunlight until the colour had changed from pale greenish-blue to dark greenish-black. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex' _diffrn_measurement_method 'CCD area detector' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16154 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.98 _reflns_number_total 3935 _reflns_number_gt 3122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_cell_refinement 'SMART-NT 5.6 (Bruker AXS Inc., 2000)' _computing_data_reduction 'SAINT+ 6.0 (Bruker AXS Inc., 2000)' _computing_structure_solution 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_structure_refinement 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_molecular_graphics 'SHELXTL 5.1 (Bruker AXS Inc., 1997)' _computing_publication_material 'SHELXTL 5.1 (Bruker AXS Inc., 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. Unlike most atoms of the viologen molecule, the thermal parameters of the atoms of the hexacyanometallate complex anion are markedly anisotropic, suggesting unresolved disorder between two closely separated sites. Attempts to resolve this disorder, or twinned refinements of the structure in lower-symmetry space groups, did not improve the structure. Some of the of the lattice water molecules, those corresponding to O(15), O(16) and O(17), were disordered over two or more sites. The H-atoms bonded to O(11) and O(12) were located and refined with restraints on the O-H distances. ; _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^)+(0.1131P)^2^+14.3861P] 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 3935 _refine_ls_number_parameters 267 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.2028 _refine_ls_wR_factor_gt 0.1904 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.047 _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 Fe1 Fe 0.5000 0.5000 0.5000 0.0591(4) Uani 1 4 d S . . C1 C 0.5000 0.5000 0.41404(19) 0.0477(11) Uani 1 2 d S . . N1 N 0.5000 0.5000 0.36218(15) 0.0418(8) Uani 1 2 d S . . C2 C 0.4346(2) 0.4276(5) 0.5000 0.0591(14) Uani 1 2 d S . . N2 N 0.39478(18) 0.3826(4) 0.5000 0.0586(12) Uani 1 2 d S . . C3 C 0.4694(3) 0.6498(7) 0.5000 0.0662(18) Uani 1 2 d S . . N3 N 0.4497(2) 0.7417(6) 0.5000 0.0757(17) Uani 1 2 d S . . C4 C 0.45489(11) 0.7537(2) 0.33827(17) 0.0459(7) Uani 1 1 d . . . H4A H 0.4629 0.6745 0.3287 0.055 Uiso 1 1 calc R . . C5 C 0.49228(11) 0.8376(2) 0.33906(18) 0.0477(8) Uani 1 1 d . . . H5A H 0.5262 0.8165 0.3303 0.057 Uiso 1 1 calc R . . C6 C 0.48008(10) 0.9540(2) 0.35287(14) 0.0368(6) Uani 1 1 d . . . C7 C 0.43006(10) 0.9814(2) 0.36677(14) 0.0384(6) Uani 1 1 d . . . H7A H 0.4211 1.0599 0.3768 0.046 Uiso 1 1 calc R . . C8 C 0.39392(10) 0.8951(2) 0.36590(13) 0.0371(6) Uani 1 1 d . . . H8A H 0.3598 0.9133 0.3757 0.045 Uiso 1 1 calc R . . N4 N 0.40700(8) 0.78391(18) 0.35107(11) 0.0329(5) Uani 1 1 d . . . C9 C 0.36773(9) 0.6937(2) 0.34979(11) 0.0311(5) Uani 1 1 d . . . C10 C 0.33269(9) 0.6860(2) 0.30341(11) 0.0290(5) Uani 1 1 d . . . C11 C 0.29440(9) 0.6035(2) 0.30592(12) 0.0300(5) Uani 1 1 d . . . H11A H 0.2698 0.5983 0.2750 0.036 Uiso 1 1 calc R . . C12 C 0.29279(10) 0.5286(2) 0.35469(12) 0.0337(6) Uani 1 1 d . . . C13 C 0.32806(12) 0.5312(3) 0.40006(12) 0.0400(6) Uani 1 1 d . . . H13A H 0.3265 0.4769 0.4324 0.048 Uiso 1 1 calc R . . C14 C 0.36600(11) 0.6155(3) 0.39726(12) 0.0391(6) Uani 1 1 d . . . H14A H 0.3908 0.6194 0.4280 0.047 Uiso 1 1 calc R . . N5 N 0.33505(9) 0.76146(19) 0.24952(10) 0.0334(5) Uani 1 1 d . . . O1 O 0.36823(8) 0.83597(16) 0.24571(10) 0.0407(5) Uani 1 1 d . . . O2 O 0.30320(8) 0.74343(19) 0.21055(10) 0.0441(5) Uani 1 1 d . . . N6 N 0.25140(10) 0.4409(2) 0.35747(11) 0.0418(6) Uani 1 1 d . . . O3 O 0.22160(8) 0.43815(19) 0.31519(10) 0.0444(5) Uani 1 1 d . . . O4 O 0.24933(10) 0.3765(2) 0.40114(12) 0.0586(7) Uani 1 1 d . . . O11 O 0.38954(10) 0.2604(2) 0.38478(13) 0.0567(6) Uani 1 1 d D . . H111 H 0.3971(19) 0.292(4) 0.4177(18) 0.085 Uiso 1 1 d D . . H112 H 0.3601(15) 0.216(4) 0.399(2) 0.085 Uiso 1 1 d D . . O12 O 0.42055(12) 0.4045(3) 0.28882(14) 0.0695(8) Uani 1 1 d D . . H121 H 0.4480(16) 0.432(5) 0.303(3) 0.104 Uiso 1 1 d D . . H122 H 0.407(2) 0.358(5) 0.320(2) 0.104 Uiso 1 1 d D . . O13 O 0.19294(12) 0.6114(3) 0.41657(14) 0.0869(11) Uani 1 1 d . . . O14 O 0.26516(16) 0.6945(4) 0.5000 0.0718(11) Uani 1 2 d S . . O15A O 0.3452(5) 0.8776(13) 0.5000 0.075(3) Uiso 0.34 2 d SPU A 1 O17A O 0.3856(6) 1.1119(15) 0.5000 0.087(3) Uiso 0.34 2 d SPU B 1 O15B O 0.3561(3) 0.8176(7) 0.5000 0.0571(15) Uiso 0.56 2 d SPU C 2 O17B O 0.3642(4) 1.0477(10) 0.5000 0.088(2) Uiso 0.56 2 d SPU D 2 O15C O 0.3808(7) 0.9716(18) 0.5000 0.059(3) Uiso 0.20 2 d SPU E 3 O16A O 0.4753(5) 1.0718(10) 0.5000 0.086(3) Uiso 0.50 2 d SPU F 1 O16B O 0.4589(4) 1.1154(9) 0.5000 0.077(2) Uiso 0.50 2 d SPU G 2 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 0.0733(7) 0.0838(8) 0.0201(4) 0.000 0.000 -0.0461(6) C1 0.056(3) 0.058(3) 0.0288(19) 0.000 0.000 -0.024(2) N1 0.058(2) 0.0423(18) 0.0254(15) 0.000 0.000 -0.0089(16) C2 0.081(4) 0.076(3) 0.0199(17) 0.000 0.000 -0.033(3) N2 0.073(3) 0.074(3) 0.0288(17) 0.000 0.000 -0.037(2) C3 0.090(4) 0.083(4) 0.025(2) 0.000 0.000 -0.061(4) N3 0.093(4) 0.099(4) 0.035(2) 0.000 0.000 -0.064(4) C4 0.0373(14) 0.0241(12) 0.076(2) -0.0045(13) 0.0112(14) -0.0024(11) C5 0.0309(14) 0.0250(12) 0.087(2) -0.0010(14) 0.0107(14) 0.0009(10) C6 0.0317(13) 0.0246(11) 0.0540(17) -0.0004(11) -0.0002(11) -0.0055(11) C7 0.0344(13) 0.0270(13) 0.0539(17) -0.0135(11) 0.0029(12) -0.0020(10) C8 0.0321(12) 0.0308(13) 0.0484(16) -0.0133(11) 0.0060(11) -0.0026(10) N4 0.0314(11) 0.0252(10) 0.0423(12) -0.0067(9) 0.0049(9) -0.0074(8) C9 0.0332(12) 0.0264(11) 0.0338(12) -0.0082(10) 0.0081(10) -0.0086(10) C10 0.0316(12) 0.0233(11) 0.0322(12) -0.0034(9) 0.0079(9) 0.0017(9) C11 0.0309(12) 0.0271(11) 0.0321(12) -0.0069(9) 0.0035(9) 0.0000(9) C12 0.0349(13) 0.0336(13) 0.0327(12) -0.0050(10) 0.0069(10) -0.0111(10) C13 0.0473(16) 0.0450(15) 0.0277(12) 0.0010(11) 0.0045(11) -0.0171(12) C14 0.0457(15) 0.0435(15) 0.0282(12) -0.0047(11) -0.0005(11) -0.0134(12) N5 0.0356(11) 0.0281(10) 0.0365(11) -0.0011(9) 0.0074(9) 0.0040(8) O1 0.0481(11) 0.0277(9) 0.0464(11) 0.0026(8) 0.0100(9) -0.0063(8) O2 0.0427(11) 0.0470(11) 0.0425(11) 0.0081(9) -0.0003(9) 0.0005(9) N6 0.0410(12) 0.0419(13) 0.0424(13) -0.0013(10) 0.0076(11) -0.0146(10) O3 0.0381(10) 0.0469(12) 0.0481(12) -0.0094(9) 0.0024(9) -0.0144(9) O4 0.0563(14) 0.0588(14) 0.0605(14) 0.0194(12) 0.0036(11) -0.0245(12) O11 0.0621(15) 0.0413(12) 0.0668(16) -0.0147(11) -0.0154(12) -0.0001(10) O12 0.0663(17) 0.0686(17) 0.0734(18) -0.0281(15) -0.0023(14) -0.0233(14) O13 0.0713(19) 0.126(3) 0.0634(18) -0.0310(18) -0.0088(14) 0.0363(19) O14 0.072(3) 0.093(3) 0.051(2) 0.000 0.000 -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 Fe1 C3 1.887(9) 9_666 ? Fe1 C3 1.887(9) . ? Fe1 C2 1.914(5) . ? Fe1 C2 1.914(5) 9_666 ? Fe1 C1 1.918(4) 9_666 ? Fe1 C1 1.918(4) . ? C1 N1 1.157(6) . ? C2 N2 1.172(6) . ? C3 N3 1.167(9) . ? C4 N4 1.343(4) . ? C4 C5 1.374(4) . ? C4 H4A 0.9500 . ? C5 C6 1.397(4) . ? C5 H5A 0.9500 . ? C6 C7 1.394(4) . ? C6 C6 1.485(5) 2_675 ? C7 C8 1.370(4) . ? C7 H7A 0.9500 . ? C8 N4 1.352(3) . ? C8 H8A 0.9500 . ? N4 C9 1.460(3) . ? C9 C14 1.384(4) . ? C9 C10 1.392(4) . ? C10 C11 1.382(3) . ? C10 N5 1.478(3) . ? C11 C12 1.382(4) . ? C11 H11A 0.9500 . ? C12 C13 1.377(4) . ? C12 N6 1.481(3) . ? C13 C14 1.389(4) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? N5 O1 1.223(3) . ? N5 O2 1.228(3) . ? N6 O4 1.220(3) . ? N6 O3 1.230(3) . ? O11 H111 0.84(3) . ? O11 H112 0.98(3) . ? O12 H121 0.85(3) . ? O12 H122 0.95(3) . ? 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 C3 Fe1 C3 180.0 9_666 . ? C3 Fe1 C2 89.9(3) 9_666 . ? C3 Fe1 C2 90.1(3) . . ? C3 Fe1 C2 90.1(3) 9_666 9_666 ? C3 Fe1 C2 89.9(3) . 9_666 ? C2 Fe1 C2 180.0 . 9_666 ? C3 Fe1 C1 90.0 9_666 9_666 ? C3 Fe1 C1 90.0 . 9_666 ? C2 Fe1 C1 90.0 . 9_666 ? C2 Fe1 C1 90.0 9_666 9_666 ? C3 Fe1 C1 90.0 9_666 . ? C3 Fe1 C1 90.0 . . ? C2 Fe1 C1 90.0 . . ? C2 Fe1 C1 90.0 9_666 . ? C1 Fe1 C1 180.0 9_666 . ? N1 C1 Fe1 180.0 . . ? N2 C2 Fe1 179.6(6) . . ? N3 C3 Fe1 179.0(5) . . ? N4 C4 C5 119.9(2) . . ? N4 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5A 120.2 . . ? C6 C5 H5A 120.2 . . ? C7 C6 C5 118.7(2) . . ? C7 C6 C6 121.0(3) . 2_675 ? C5 C6 C6 120.3(3) . 2_675 ? C8 C7 C6 119.9(2) . . ? C8 C7 H7A 120.1 . . ? C6 C7 H7A 120.1 . . ? N4 C8 C7 119.7(2) . . ? N4 C8 H8A 120.2 . . ? C7 C8 H8A 120.2 . . ? C4 N4 C8 122.2(2) . . ? C4 N4 C9 119.1(2) . . ? C8 N4 C9 118.7(2) . . ? C14 C9 C10 120.4(2) . . ? C14 C9 N4 117.4(2) . . ? C10 C9 N4 122.1(2) . . ? C11 C10 C9 120.0(2) . . ? C11 C10 N5 117.3(2) . . ? C9 C10 N5 122.7(2) . . ? C10 C11 C12 118.2(2) . . ? C10 C11 H11A 120.9 . . ? C12 C11 H11A 120.9 . . ? C13 C12 C11 123.0(2) . . ? C13 C12 N6 119.0(2) . . ? C11 C12 N6 118.0(2) . . ? C12 C13 C14 118.1(3) . . ? C12 C13 H13A 120.9 . . ? C14 C13 H13A 120.9 . . ? C9 C14 C13 120.1(3) . . ? C9 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? O1 N5 O2 124.0(2) . . ? O1 N5 C10 119.3(2) . . ? O2 N5 C10 116.8(2) . . ? O4 N6 O3 124.6(2) . . ? O4 N6 C12 118.1(3) . . ? O3 N6 C12 117.3(2) . . ? H111 O11 H112 97(5) . . ? H121 O12 H122 105(5) . . ? 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 N4 C4 C5 C6 -0.4(6) . . . . ? C4 C5 C6 C7 1.3(5) . . . . ? C4 C5 C6 C6 -178.9(3) . . . 2_675 ? C5 C6 C7 C8 -0.9(5) . . . . ? C6 C6 C7 C8 179.4(2) 2_675 . . . ? C6 C7 C8 N4 -0.5(5) . . . . ? C5 C4 N4 C8 -1.1(5) . . . . ? C5 C4 N4 C9 179.8(3) . . . . ? C7 C8 N4 C4 1.5(5) . . . . ? C7 C8 N4 C9 -179.3(3) . . . . ? C4 N4 C9 C14 75.5(3) . . . . ? C8 N4 C9 C14 -103.7(3) . . . . ? C4 N4 C9 C10 -105.3(3) . . . . ? C8 N4 C9 C10 75.6(3) . . . . ? C14 C9 C10 C11 3.0(4) . . . . ? N4 C9 C10 C11 -176.2(2) . . . . ? C14 C9 C10 N5 -175.3(2) . . . . ? N4 C9 C10 N5 5.4(4) . . . . ? C9 C10 C11 C12 -1.2(3) . . . . ? N5 C10 C11 C12 177.2(2) . . . . ? C10 C11 C12 C13 -1.3(4) . . . . ? C10 C11 C12 N6 179.4(2) . . . . ? C11 C12 C13 C14 1.9(4) . . . . ? N6 C12 C13 C14 -178.8(3) . . . . ? C10 C9 C14 C13 -2.4(4) . . . . ? N4 C9 C14 C13 176.9(2) . . . . ? C12 C13 C14 C9 -0.1(4) . . . . ? C11 C10 N5 O1 179.7(2) . . . . ? C9 C10 N5 O1 -1.9(3) . . . . ? C11 C10 N5 O2 -1.2(3) . . . . ? C9 C10 N5 O2 177.2(2) . . . . ? C13 C12 N6 O4 2.2(4) . . . . ? C11 C12 N6 O4 -178.4(3) . . . . ? C13 C12 N6 O3 -177.5(3) . . . . ? C11 C12 N6 O3 1.9(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 O11 H111 N2 0.84(3) 2.10(4) 2.926(3) 164(5) . O11 H112 O13 0.98(3) 1.88(3) 2.851(4) 170(5) 12_655 O12 H121 N1 0.85(3) 2.06(4) 2.876(3) 161(6) . O12 H122 O11 0.95(3) 1.88(4) 2.818(4) 172(5) . C4 H4A N1 0.95 2.34 3.167(3) 145.8 . C13 H13A N2 0.95 2.59 3.307(5) 133.0 . C14 H14A N2 0.95 3.14 3.584(5) 110.6 . C14 H14A N3 0.95 2.63 3.495(4) 150.8 . C8 H8A O3 0.95 2.56 3.294(3) 134.6 12_665 _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.613 _refine_diff_density_min -1.672 _refine_diff_density_rms 0.088