Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Christoph Janiak' _publ_contact_author_address ; Albert-Ludwigs-Universitat Freiburg Institut fur Anorganische Chemie Albertstr. 21 Freiburg D-79104 GERMANY ; _publ_contact_author_email JANIAK@UNI-FREIBURG.DE _publ_section_title ; Hydrogen-bonding, pi-stacking and Cl-anion-pi interactions of linear bipyridinium cations with phosphate, chloride and [CoCl4]2- anions ; loop_ _publ_author_name 'Christoph Janiak' 'Khalid Abu-Shandi' 'Thomas Dorn' data_dorn2 _database_code_depnum_ccdc_archive 'CCDC 276029' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-bi-1,6-naphthyridin-1,6,6'-ium-tetrachlorocobaltate(II) -chloride ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 N4, CoCl4, Cl' _chemical_formula_sum 'C16 H13 Cl5 Co N4' _chemical_formula_weight 497.48 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.2231(5) _cell_length_b 10.3057(8) _cell_length_c 15.4812(11) _cell_angle_alpha 75.2950(10) _cell_angle_beta 79.2990(10) _cell_angle_gamma 74.7150(10) _cell_volume 918.84(12) _cell_formula_units_Z 2 _cell_measurement_temperature 205(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour pale-green _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.798 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 1.670 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5548 _exptl_absorpt_correction_T_max 0.5548 _exptl_absorpt_process_details 'SADABS (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 205(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD area detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7958 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.35 _reflns_number_total 4072 _reflns_number_gt 3452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 1997a)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The protic hydrogen atoms on N were found and refined with Ueq(H) = 1.5 Ueq(N/O). Hydrogen atoms on C were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C). ; _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^)+(0.0403P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4072 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0657 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Co Co 0.11400(4) 0.88303(3) 0.293145(16) 0.02213(8) Uani 1 1 d . . . Cl1 Cl -0.13481(8) 1.05521(5) 0.35104(3) 0.02966(11) Uani 1 1 d . . . Cl2 Cl 0.47113(8) 0.90128(5) 0.29698(3) 0.02781(11) Uani 1 1 d . . . Cl3 Cl 0.08468(8) 0.67537(5) 0.38192(3) 0.02812(11) Uani 1 1 d . . . Cl4 Cl 0.08211(8) 0.91083(5) 0.14494(3) 0.02658(11) Uani 1 1 d . . . Cl5 Cl 0.09912(8) 0.42370(5) 0.13242(3) 0.03054(12) Uani 1 1 d . . . N3 N 0.4469(3) 0.44436(16) 0.25806(10) 0.0225(3) Uani 1 1 d . . . N1 N 0.3934(3) 0.85180(16) -0.15081(11) 0.0243(3) Uani 1 1 d . . . H1 H 0.375(4) 0.901(2) -0.2011(15) 0.036 Uiso 1 1 d . . . N2 N 0.4395(3) 0.61167(16) 0.10167(10) 0.0206(3) Uani 1 1 d . . . H2 H 0.361(4) 0.555(2) 0.1200(15) 0.031 Uiso 1 1 d . . . N4 N 0.3819(3) 0.18489(17) 0.50398(11) 0.0264(4) Uani 1 1 d . . . H4 H 0.367(4) 0.132(2) 0.5511(17) 0.040 Uiso 1 1 d . . . C1 C 0.5786(3) 0.62422(18) 0.15343(12) 0.0210(4) Uani 1 1 d . . . C2 C 0.7107(3) 0.72235(19) 0.12321(12) 0.0240(4) Uani 1 1 d . . . H2A H 0.8074 0.7308 0.1604 0.029 Uiso 1 1 calc R . . C3 C 0.6972(3) 0.80516(19) 0.03948(12) 0.0237(4) Uani 1 1 d . . . H3 H 0.7843 0.8715 0.0185 0.028 Uiso 1 1 calc R . . C4 C 0.5513(3) 0.79058(18) -0.01560(12) 0.0206(4) Uani 1 1 d . . . C5 C 0.5325(3) 0.86975(19) -0.10290(12) 0.0244(4) Uani 1 1 d . . . H5 H 0.6192 0.9357 -0.1273 0.029 Uiso 1 1 calc R . . C6 C 0.2631(3) 0.75802(19) -0.12056(12) 0.0243(4) Uani 1 1 d . . . H6 H 0.1662 0.7497 -0.1577 0.029 Uiso 1 1 calc R . . C7 C 0.2731(3) 0.67624(18) -0.03649(12) 0.0221(4) Uani 1 1 d . . . H7 H 0.1844 0.6109 -0.0149 0.027 Uiso 1 1 calc R . . C8 C 0.4197(3) 0.69205(17) 0.01738(11) 0.0194(3) Uani 1 1 d . . . C9 C 0.5789(3) 0.53018(18) 0.24416(12) 0.0213(4) Uani 1 1 d . . . C10 C 0.7081(3) 0.53719(19) 0.30835(12) 0.0250(4) Uani 1 1 d . . . H10 H 0.8024 0.5995 0.2944 0.030 Uiso 1 1 calc R . . C11 C 0.6918(3) 0.45093(19) 0.39091(12) 0.0250(4) Uani 1 1 d . . . H11 H 0.7753 0.4524 0.4353 0.030 Uiso 1 1 calc R . . C12 C 0.5475(3) 0.35908(19) 0.40885(12) 0.0223(4) Uani 1 1 d . . . C13 C 0.5190(3) 0.26847(19) 0.49176(12) 0.0263(4) Uani 1 1 d . . . H13 H 0.5969 0.2668 0.5387 0.032 Uiso 1 1 calc R . . C14 C 0.2630(3) 0.1812(2) 0.43936(13) 0.0277(4) Uani 1 1 d . . . H14 H 0.1675 0.1199 0.4517 0.033 Uiso 1 1 calc R . . C15 C 0.2832(3) 0.2664(2) 0.35719(13) 0.0260(4) Uani 1 1 d . . . H15 H 0.2026 0.2646 0.3120 0.031 Uiso 1 1 calc R . . C16 C 0.4275(3) 0.35844(18) 0.34031(12) 0.0213(4) 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 Co 0.02205(14) 0.02283(14) 0.02266(14) -0.00486(10) -0.00361(10) -0.00658(10) Cl1 0.0285(2) 0.0262(2) 0.0354(3) -0.01130(19) -0.00155(19) -0.00549(19) Cl2 0.0262(2) 0.0344(3) 0.0237(2) 0.00360(18) -0.00776(17) -0.01467(19) Cl3 0.0279(2) 0.0240(2) 0.0334(3) -0.00329(19) -0.00571(19) -0.00906(18) Cl4 0.0263(2) 0.0319(2) 0.0250(2) -0.00813(18) -0.00496(17) -0.00943(19) Cl5 0.0268(2) 0.0333(3) 0.0368(3) -0.0107(2) -0.00560(19) -0.0119(2) N3 0.0250(8) 0.0246(8) 0.0196(8) -0.0040(6) -0.0037(6) -0.0088(6) N1 0.0267(8) 0.0232(8) 0.0203(8) 0.0018(6) -0.0044(6) -0.0063(7) N2 0.0235(8) 0.0192(7) 0.0206(8) -0.0032(6) -0.0027(6) -0.0087(6) N4 0.0291(9) 0.0288(9) 0.0178(8) 0.0009(6) -0.0014(6) -0.0075(7) C1 0.0222(9) 0.0195(9) 0.0217(9) -0.0060(7) -0.0038(7) -0.0033(7) C2 0.0238(9) 0.0259(9) 0.0253(9) -0.0062(7) -0.0055(7) -0.0086(7) C3 0.0231(9) 0.0215(9) 0.0286(10) -0.0066(7) -0.0012(7) -0.0091(7) C4 0.0210(9) 0.0195(9) 0.0210(9) -0.0043(7) -0.0010(7) -0.0054(7) C5 0.0244(9) 0.0218(9) 0.0261(9) -0.0024(7) -0.0020(7) -0.0071(7) C6 0.0245(9) 0.0233(9) 0.0258(9) -0.0036(7) -0.0061(7) -0.0061(7) C7 0.0236(9) 0.0205(9) 0.0238(9) -0.0040(7) -0.0043(7) -0.0076(7) C8 0.0206(8) 0.0175(8) 0.0189(9) -0.0040(7) -0.0019(7) -0.0028(7) C9 0.0225(9) 0.0200(9) 0.0216(9) -0.0057(7) -0.0038(7) -0.0035(7) C10 0.0264(9) 0.0249(9) 0.0274(10) -0.0067(8) -0.0070(7) -0.0088(8) C11 0.0266(9) 0.0267(10) 0.0246(9) -0.0069(8) -0.0100(7) -0.0050(8) C12 0.0232(9) 0.0232(9) 0.0202(9) -0.0062(7) -0.0040(7) -0.0024(7) C13 0.0273(10) 0.0278(10) 0.0225(9) -0.0059(8) -0.0049(7) -0.0024(8) C14 0.0277(10) 0.0298(10) 0.0262(10) -0.0042(8) -0.0011(8) -0.0112(8) C15 0.0273(10) 0.0289(10) 0.0241(9) -0.0048(8) -0.0050(7) -0.0099(8) C16 0.0222(9) 0.0215(9) 0.0194(9) -0.0048(7) -0.0023(7) -0.0036(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 Co Cl3 2.2631(5) . ? Co Cl4 2.2783(5) . ? Co Cl1 2.2787(5) . ? Co Cl2 2.2920(5) . ? N3 C9 1.313(2) . ? N3 C16 1.359(2) . ? N1 C5 1.314(2) . ? N1 C6 1.361(2) . ? N1 H1 0.83(2) . ? N2 C1 1.334(2) . ? N2 C8 1.364(2) . ? N2 H2 0.82(2) . ? N4 C13 1.323(2) . ? N4 C14 1.363(2) . ? N4 H4 0.80(2) . ? C1 C2 1.404(2) . ? C1 C9 1.490(2) . ? C2 C3 1.363(3) . ? C2 H2A 0.9400 . ? C3 C4 1.414(2) . ? C3 H3 0.9400 . ? C4 C5 1.398(2) . ? C4 C8 1.408(2) . ? C5 H5 0.9400 . ? C6 C7 1.361(2) . ? C6 H6 0.9400 . ? C7 C8 1.409(2) . ? C7 H7 0.9400 . ? C9 C10 1.415(2) . ? C10 C11 1.363(3) . ? C10 H10 0.9400 . ? C11 C12 1.415(3) . ? C11 H11 0.9400 . ? C12 C13 1.395(2) . ? C12 C16 1.408(2) . ? C13 H13 0.9400 . ? C14 C15 1.355(3) . ? C14 H14 0.9400 . ? C15 C16 1.418(3) . ? C15 H15 0.9400 . ? 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 Cl3 Co Cl4 115.98(2) . . ? Cl3 Co Cl1 110.29(2) . . ? Cl4 Co Cl1 110.19(2) . . ? Cl3 Co Cl2 105.552(19) . . ? Cl4 Co Cl2 105.774(19) . . ? Cl1 Co Cl2 108.64(2) . . ? C9 N3 C16 118.17(16) . . ? C5 N1 C6 123.59(17) . . ? C5 N1 H1 120.7(16) . . ? C6 N1 H1 115.7(16) . . ? C1 N2 C8 121.93(16) . . ? C1 N2 H2 120.6(15) . . ? C8 N2 H2 117.4(15) . . ? C13 N4 C14 123.69(17) . . ? C13 N4 H4 120.2(17) . . ? C14 N4 H4 116.1(18) . . ? N2 C1 C2 120.98(16) . . ? N2 C1 C9 115.49(16) . . ? C2 C1 C9 123.52(16) . . ? C3 C2 C1 119.38(16) . . ? C3 C2 H2A 120.3 . . ? C1 C2 H2A 120.3 . . ? C2 C3 C4 119.50(16) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C8 117.85(16) . . ? C5 C4 C3 122.65(17) . . ? C8 C4 C3 119.50(16) . . ? N1 C5 C4 119.89(17) . . ? N1 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 N1 120.05(17) . . ? C7 C6 H6 120.0 . . ? N1 C6 H6 120.0 . . ? C6 C7 C8 118.33(17) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? N2 C8 C4 118.70(16) . . ? N2 C8 C7 121.01(16) . . ? C4 C8 C7 120.28(16) . . ? N3 C9 C10 124.50(17) . . ? N3 C9 C1 113.65(16) . . ? C10 C9 C1 121.84(16) . . ? C11 C10 C9 117.99(17) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C10 C11 C12 119.02(17) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C13 C12 C16 118.37(17) . . ? C13 C12 C11 122.74(17) . . ? C16 C12 C11 118.89(16) . . ? N4 C13 C12 119.66(17) . . ? N4 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C15 C14 N4 119.66(18) . . ? C15 C14 H14 120.2 . . ? N4 C14 H14 120.2 . . ? C14 C15 C16 119.11(18) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? N3 C16 C12 121.41(16) . . ? N3 C16 C15 119.10(16) . . ? C12 C16 C15 119.49(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 N1 H1 Cl2 0.83(2) 2.49(2) 3.1313(16) 135(2) 2_675 N1 H1 Cl1 0.83(2) 2.87(2) 3.5565(17) 142(2) 2_575 N2 H2 Cl5 0.82(2) 2.33(2) 3.1282(16) 164(2) . N4 H4 Cl2 0.80(2) 2.64(2) 3.2170(17) 131(2) 2_666 N4 H4 Cl1 0.80(2) 2.69(2) 3.3806(17) 145(2) 2_566 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.35 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.555 _refine_diff_density_min -0.530 _refine_diff_density_rms 0.088 data_2zm_1_3 _database_code_depnum_ccdc_archive 'CCDC 276030' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-bipyridin-1,1'-ium bis(1,1'-binaphthalene-2,2'-diyl phosphate).2.5H2O ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H39 N2 O10.50 P2' _chemical_formula_weight 897.77 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 P21/n 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 19.004(16) _cell_length_b 12.519(11) _cell_length_c 19.141(18) _cell_angle_alpha 90.00 _cell_angle_beta 110.093(17) _cell_angle_gamma 90.00 _cell_volume 4277(7) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description isometric _exptl_crystal_colour bright-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1868 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9834 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD area detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23012 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.60 _reflns_number_total 8810 _reflns_number_gt 6038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 1997a)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The protic hydrogen atoms on N (bipyridine) and O (water) were found and refined with Ueq(H) = 1.5 Ueq(N/O). The H-atoms of the half-occupied water molecule with O11, which is crystallographically disordered around a center of inversion, could found but had to be fixed upon further refinement. Hydrogen atoms on C (bipyridine and binaphthyl) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8810 _refine_ls_number_parameters 604 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0898 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _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 N1 N 0.20657(9) 0.35541(14) 0.36706(10) 0.0491(5) Uani 1 1 d . . . H1A H 0.2546(13) 0.3872(19) 0.3809(12) 0.074 Uiso 1 1 d . . . C1 C 0.18484(10) 0.30338(17) 0.30242(12) 0.0469(5) Uani 1 1 d . . . H1 H 0.2184 0.2947 0.2765 0.056 Uiso 1 1 calc R . . C2 C 0.11382(9) 0.26253(15) 0.27355(11) 0.0395(4) Uani 1 1 d . . . H2 H 0.0985 0.2257 0.2280 0.047 Uiso 1 1 calc R . . C3 C 0.06438(9) 0.27626(15) 0.31256(10) 0.0357(4) Uani 1 1 d . . . C4 C 0.08910(11) 0.33020(17) 0.38023(11) 0.0487(5) Uani 1 1 d . . . H4 H 0.0570 0.3400 0.4077 0.058 Uiso 1 1 calc R . . C5 C 0.16184(12) 0.36919(18) 0.40648(12) 0.0554(6) Uani 1 1 d . . . H5 H 0.1795 0.4054 0.4522 0.066 Uiso 1 1 calc R . . N2 N -0.15754(8) 0.16420(13) 0.21533(8) 0.0367(4) Uani 1 1 d . . . H2A H -0.2087(12) 0.1376(16) 0.1876(11) 0.055 Uiso 1 1 d . . . C6 C -0.14495(10) 0.25453(16) 0.25544(10) 0.0383(4) Uani 1 1 d . . . H6 H -0.1857 0.2923 0.2605 0.046 Uiso 1 1 calc R . . C7 C -0.07341(10) 0.29280(15) 0.28936(10) 0.0373(4) Uani 1 1 d . . . H7 H -0.0648 0.3559 0.3177 0.045 Uiso 1 1 calc R . . C8 C -0.01355(9) 0.23547(15) 0.28062(9) 0.0327(4) Uani 1 1 d . . . C9 C -0.02841(9) 0.14098(16) 0.23944(10) 0.0385(4) Uani 1 1 d . . . H9 H 0.0111 0.1011 0.2336 0.046 Uiso 1 1 calc R . . C10 C -0.10113(10) 0.10651(17) 0.20744(10) 0.0397(5) Uani 1 1 d . . . H10 H -0.1114 0.0426 0.1800 0.048 Uiso 1 1 calc R . . P1 P -0.34781(2) 0.08427(4) 0.17853(2) 0.03632(13) Uani 1 1 d . . . O1 O -0.33999(6) 0.20578(10) 0.21179(6) 0.0360(3) Uani 1 1 d . . . O2 O -0.32298(6) 0.01320(10) 0.25438(6) 0.0356(3) Uani 1 1 d . . . O3 O -0.28794(7) 0.07985(11) 0.14432(7) 0.0452(3) Uani 1 1 d . . . O4 O -0.42546(7) 0.05382(12) 0.13615(7) 0.0498(4) Uani 1 1 d . . . C11 C -0.36551(9) 0.22802(14) 0.27102(9) 0.0313(4) Uani 1 1 d . . . C12 C -0.43258(10) 0.28678(15) 0.25512(10) 0.0370(4) Uani 1 1 d . . . H12 H -0.4590 0.3094 0.2063 0.044 Uiso 1 1 calc R . . C13 C -0.45864(10) 0.31036(15) 0.31148(10) 0.0390(4) Uani 1 1 d . . . H13 H -0.5027 0.3508 0.3014 0.047 Uiso 1 1 calc R . . C14 C -0.42013(9) 0.27457(14) 0.38499(9) 0.0324(4) Uani 1 1 d . . . C15 C -0.44853(10) 0.29571(15) 0.44324(10) 0.0404(5) Uani 1 1 d . . . H15 H -0.4935 0.3339 0.4330 0.049 Uiso 1 1 calc R . . C16 C -0.41107(11) 0.26105(16) 0.51429(11) 0.0430(5) Uani 1 1 d . . . H16 H -0.4302 0.2760 0.5525 0.052 Uiso 1 1 calc R . . C17 C -0.34379(10) 0.20285(15) 0.52996(10) 0.0399(4) Uani 1 1 d . . . H17 H -0.3181 0.1798 0.5789 0.048 Uiso 1 1 calc R . . C18 C -0.31550(10) 0.17949(15) 0.47507(9) 0.0348(4) Uani 1 1 d . . . H18 H -0.2715 0.1385 0.4865 0.042 Uiso 1 1 calc R . . C19 C -0.35149(9) 0.21608(13) 0.40081(9) 0.0295(4) Uani 1 1 d . . . C20 C -0.32317(9) 0.19394(14) 0.34182(9) 0.0287(4) Uani 1 1 d . . . C21 C -0.25497(9) 0.04170(14) 0.31005(9) 0.0312(4) Uani 1 1 d . . . C22 C -0.19226(10) -0.02352(15) 0.31833(10) 0.0363(4) Uani 1 1 d . . . H22 H -0.1970 -0.0852 0.2890 0.044 Uiso 1 1 calc R . . C23 C -0.12444(10) 0.00364(15) 0.36931(10) 0.0386(4) Uani 1 1 d . . . H23 H -0.0827 -0.0407 0.3759 0.046 Uiso 1 1 calc R . . C24 C -0.11625(9) 0.09841(15) 0.41252(9) 0.0353(4) Uani 1 1 d . . . C25 C -0.04511(10) 0.13314(18) 0.46201(10) 0.0451(5) Uani 1 1 d . . . H25 H -0.0026 0.0908 0.4680 0.054 Uiso 1 1 calc R . . C26 C -0.03730(11) 0.22651(19) 0.50089(11) 0.0518(6) Uani 1 1 d . . . H26 H 0.0101 0.2475 0.5336 0.062 Uiso 1 1 calc R . . C27 C -0.10051(11) 0.29142(18) 0.49189(11) 0.0496(5) Uani 1 1 d . . . H27 H -0.0949 0.3560 0.5183 0.059 Uiso 1 1 calc R . . C28 C -0.17006(10) 0.26136(16) 0.44504(10) 0.0390(4) Uani 1 1 d . . . H28 H -0.2114 0.3060 0.4395 0.047 Uiso 1 1 calc R . . C29 C -0.18075(9) 0.16371(14) 0.40463(9) 0.0309(4) Uani 1 1 d . . . C30 C -0.25283(9) 0.13127(14) 0.35291(9) 0.0291(4) Uani 1 1 d . . . P2 P 0.35887(2) 0.50364(4) 0.34347(2) 0.03151(12) Uani 1 1 d . . . O5 O 0.32248(6) 0.42578(9) 0.27145(6) 0.0311(3) Uani 1 1 d . . . O6 O 0.30786(6) 0.61105(10) 0.31794(6) 0.0323(3) Uani 1 1 d . . . O7 O 0.43609(6) 0.53580(11) 0.35187(6) 0.0410(3) Uani 1 1 d . . . O8 O 0.34243(6) 0.44666(11) 0.40440(6) 0.0393(3) Uani 1 1 d . . . C31 C 0.30727(9) 0.47120(14) 0.20097(8) 0.0284(4) Uani 1 1 d . . . C32 C 0.35557(9) 0.44447(16) 0.16217(9) 0.0379(4) Uani 1 1 d . . . H32 H 0.3955 0.3968 0.1829 0.045 Uiso 1 1 calc R . . C33 C 0.34367(10) 0.48874(16) 0.09395(10) 0.0420(5) Uani 1 1 d . . . H33 H 0.3758 0.4714 0.0677 0.050 Uiso 1 1 calc R . . C34 C 0.28352(10) 0.56058(15) 0.06214(9) 0.0369(4) Uani 1 1 d . . . C35 C 0.27219(13) 0.60997(18) -0.00785(10) 0.0527(6) Uani 1 1 d . . . H35 H 0.3051 0.5944 -0.0336 0.063 Uiso 1 1 calc R . . C36 C 0.21493(14) 0.6790(2) -0.03796(11) 0.0610(7) Uani 1 1 d . . . H36 H 0.2084 0.7101 -0.0845 0.073 Uiso 1 1 calc R . . C37 C 0.16511(12) 0.70481(16) -0.00060(11) 0.0521(6) Uani 1 1 d . . . H37 H 0.1258 0.7533 -0.0220 0.063 Uiso 1 1 calc R . . C38 C 0.17394(10) 0.65906(15) 0.06736(9) 0.0394(4) Uani 1 1 d . . . H38 H 0.1406 0.6769 0.0922 0.047 Uiso 1 1 calc R . . C39 C 0.23302(9) 0.58496(14) 0.10056(8) 0.0302(4) Uani 1 1 d . . . C40 C 0.24524(8) 0.53666(13) 0.17211(8) 0.0262(4) Uani 1 1 d . . . C41 C 0.22969(9) 0.59667(14) 0.28969(8) 0.0291(4) Uani 1 1 d . . . C42 C 0.18899(10) 0.62178(15) 0.33648(9) 0.0374(4) Uani 1 1 d . . . H42 H 0.2133 0.6510 0.3839 0.045 Uiso 1 1 calc R . . C43 C 0.11389(10) 0.60321(15) 0.31201(10) 0.0393(4) Uani 1 1 d . . . H43 H 0.0861 0.6211 0.3426 0.047 Uiso 1 1 calc R . . C44 C 0.07667(9) 0.55721(14) 0.24105(9) 0.0329(4) Uani 1 1 d . . . C45 C -0.00059(10) 0.52867(15) 0.21784(11) 0.0398(5) Uani 1 1 d . . . H45 H -0.0279 0.5426 0.2495 0.048 Uiso 1 1 calc R . . C46 C -0.03554(10) 0.48154(16) 0.15051(11) 0.0441(5) Uani 1 1 d . . . H46 H -0.0865 0.4633 0.1361 0.053 Uiso 1 1 calc R . . C47 C 0.00468(10) 0.46026(16) 0.10273(10) 0.0418(5) Uani 1 1 d . . . H47 H -0.0197 0.4279 0.0564 0.050 Uiso 1 1 calc R . . C48 C 0.07915(9) 0.48630(15) 0.12301(9) 0.0347(4) Uani 1 1 d . . . H48 H 0.1051 0.4712 0.0903 0.042 Uiso 1 1 calc R . . C49 C 0.11780(9) 0.53573(14) 0.19265(9) 0.0290(4) Uani 1 1 d . . . C50 C 0.19680(9) 0.55901(13) 0.21787(8) 0.0264(4) Uani 1 1 d . . . O9 O 0.58653(8) 0.55976(13) 0.44180(7) 0.0509(4) Uani 1 1 d . . . H9A H 0.5352(14) 0.5514(19) 0.4230(13) 0.076 Uiso 1 1 d . . . H9B H 0.5942(13) 0.5550(19) 0.4897(14) 0.076 Uiso 1 1 d . . . O10 O -0.23803(9) -0.02149(13) 0.03553(9) 0.0595(4) Uani 1 1 d . . . H10A H -0.1845(16) -0.004(2) 0.0493(15) 0.089 Uiso 1 1 d . . . H10B H -0.2538(14) 0.013(2) 0.0766(15) 0.089 Uiso 1 1 d . . . O11 O -0.53837(17) -0.0416(3) 0.01772(15) 0.0604(8) Uani 0.50 1 d P . . H11A H -0.5062 -0.0052 0.0454 0.091 Uiso 0.50 1 d P . . H11B H -0.5495 -0.0456 -0.0293 0.091 Uiso 0.50 1 d P . . 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 N1 0.0268(8) 0.0452(11) 0.0671(12) 0.0146(9) 0.0057(8) -0.0033(8) C1 0.0308(10) 0.0443(13) 0.0634(13) 0.0109(11) 0.0134(9) 0.0022(9) C2 0.0264(9) 0.0414(12) 0.0501(11) 0.0061(9) 0.0125(8) 0.0003(8) C3 0.0280(9) 0.0332(11) 0.0436(10) 0.0064(8) 0.0097(8) 0.0000(8) C4 0.0402(11) 0.0535(14) 0.0501(11) -0.0022(10) 0.0127(9) -0.0072(10) C5 0.0502(13) 0.0516(15) 0.0522(12) -0.0005(11) 0.0019(10) -0.0078(11) N2 0.0249(8) 0.0483(11) 0.0373(8) 0.0074(8) 0.0113(6) -0.0023(7) C6 0.0287(9) 0.0385(12) 0.0529(11) 0.0103(10) 0.0206(9) 0.0053(8) C7 0.0349(10) 0.0365(12) 0.0459(10) 0.0028(9) 0.0208(8) 0.0015(8) C8 0.0251(9) 0.0375(11) 0.0366(9) 0.0069(8) 0.0120(7) 0.0010(8) C9 0.0280(9) 0.0473(13) 0.0441(10) -0.0038(9) 0.0173(8) 0.0016(9) C10 0.0347(10) 0.0487(13) 0.0395(10) -0.0042(9) 0.0177(8) -0.0036(9) P1 0.0255(2) 0.0499(3) 0.0339(2) -0.0080(2) 0.01074(19) -0.0084(2) O1 0.0351(7) 0.0428(8) 0.0322(6) 0.0022(6) 0.0144(5) -0.0028(6) O2 0.0300(6) 0.0356(8) 0.0410(6) -0.0067(6) 0.0121(5) -0.0083(5) O3 0.0324(7) 0.0654(10) 0.0416(7) -0.0123(7) 0.0176(6) -0.0092(7) O4 0.0287(7) 0.0758(11) 0.0427(7) -0.0129(7) 0.0096(6) -0.0140(7) C11 0.0295(9) 0.0322(11) 0.0337(9) 0.0020(8) 0.0128(7) -0.0030(8) C12 0.0321(9) 0.0402(12) 0.0354(9) 0.0089(8) 0.0072(8) 0.0037(8) C13 0.0301(9) 0.0385(12) 0.0470(10) 0.0041(9) 0.0112(8) 0.0087(8) C14 0.0308(9) 0.0272(10) 0.0398(9) 0.0001(8) 0.0128(8) 0.0005(7) C15 0.0378(10) 0.0364(12) 0.0517(11) -0.0045(9) 0.0212(9) 0.0033(9) C16 0.0491(12) 0.0436(13) 0.0438(10) -0.0047(9) 0.0257(9) -0.0030(10) C17 0.0438(11) 0.0402(12) 0.0360(9) 0.0017(8) 0.0140(8) -0.0046(9) C18 0.0328(9) 0.0334(11) 0.0375(9) 0.0039(8) 0.0111(8) 0.0005(8) C19 0.0277(9) 0.0261(10) 0.0343(9) -0.0006(7) 0.0100(7) -0.0030(7) C20 0.0249(8) 0.0264(10) 0.0346(8) 0.0006(7) 0.0100(7) -0.0030(7) C21 0.0270(9) 0.0333(11) 0.0344(9) 0.0002(8) 0.0117(7) -0.0045(8) C22 0.0388(10) 0.0321(11) 0.0423(10) 0.0010(8) 0.0197(8) 0.0031(8) C23 0.0339(10) 0.0413(12) 0.0440(10) 0.0095(9) 0.0175(8) 0.0086(9) C24 0.0282(9) 0.0425(12) 0.0352(9) 0.0107(8) 0.0109(7) 0.0024(8) C25 0.0259(9) 0.0595(15) 0.0455(10) 0.0134(10) 0.0069(8) 0.0017(9) C26 0.0323(11) 0.0675(16) 0.0473(11) 0.0022(11) 0.0027(9) -0.0111(10) C27 0.0468(12) 0.0532(14) 0.0454(11) -0.0104(10) 0.0115(9) -0.0158(10) C28 0.0336(10) 0.0433(12) 0.0400(10) -0.0030(9) 0.0126(8) -0.0047(9) C29 0.0281(9) 0.0346(11) 0.0307(8) 0.0044(8) 0.0109(7) -0.0021(8) C30 0.0280(9) 0.0297(10) 0.0310(8) 0.0029(7) 0.0122(7) -0.0019(7) P2 0.0217(2) 0.0454(3) 0.0242(2) 0.0028(2) 0.00367(16) -0.0028(2) O5 0.0268(6) 0.0368(7) 0.0262(5) 0.0033(5) 0.0046(5) 0.0024(5) O6 0.0264(6) 0.0405(8) 0.0266(6) -0.0043(5) 0.0047(5) -0.0042(5) O7 0.0244(6) 0.0604(9) 0.0351(6) 0.0046(6) 0.0063(5) -0.0059(6) O8 0.0277(6) 0.0597(9) 0.0258(6) 0.0077(6) 0.0035(5) -0.0071(6) C31 0.0240(8) 0.0358(11) 0.0236(7) -0.0023(7) 0.0057(6) -0.0028(7) C32 0.0253(9) 0.0505(13) 0.0366(9) -0.0065(9) 0.0089(7) 0.0024(8) C33 0.0353(10) 0.0609(14) 0.0345(9) -0.0111(9) 0.0182(8) -0.0049(10) C34 0.0430(11) 0.0421(12) 0.0249(8) -0.0065(8) 0.0109(8) -0.0146(9) C35 0.0687(14) 0.0613(15) 0.0304(9) -0.0028(10) 0.0202(10) -0.0177(12) C36 0.0879(18) 0.0597(16) 0.0269(9) 0.0083(10) 0.0087(11) -0.0181(14) C37 0.0627(14) 0.0374(13) 0.0381(10) 0.0059(9) -0.0058(10) -0.0037(10) C38 0.0415(10) 0.0351(12) 0.0320(9) 0.0002(8) 0.0003(8) -0.0045(9) C39 0.0317(9) 0.0303(10) 0.0239(8) -0.0030(7) 0.0036(7) -0.0074(8) C40 0.0231(8) 0.0300(10) 0.0232(7) -0.0036(7) 0.0049(6) -0.0035(7) C41 0.0243(8) 0.0324(10) 0.0289(8) -0.0012(7) 0.0071(7) 0.0006(7) C42 0.0404(10) 0.0424(12) 0.0300(8) -0.0079(8) 0.0126(8) 0.0016(9) C43 0.0390(10) 0.0440(12) 0.0412(10) -0.0046(9) 0.0222(8) 0.0062(9) C44 0.0282(9) 0.0321(11) 0.0392(9) 0.0016(8) 0.0127(8) 0.0066(8) C45 0.0275(9) 0.0417(12) 0.0544(11) 0.0035(9) 0.0195(9) 0.0071(8) C46 0.0222(9) 0.0461(13) 0.0607(12) 0.0010(10) 0.0100(9) 0.0001(8) C47 0.0287(9) 0.0460(13) 0.0430(10) -0.0048(9) 0.0024(8) -0.0009(9) C48 0.0273(9) 0.0401(12) 0.0337(9) -0.0032(8) 0.0067(7) 0.0025(8) C49 0.0243(8) 0.0291(10) 0.0319(8) 0.0003(7) 0.0074(7) 0.0042(7) C50 0.0246(8) 0.0271(10) 0.0263(8) -0.0001(7) 0.0071(6) 0.0026(7) O9 0.0392(8) 0.0755(11) 0.0319(7) 0.0041(7) 0.0043(6) -0.0174(8) O10 0.0553(10) 0.0677(11) 0.0570(9) -0.0075(8) 0.0212(8) -0.0020(8) O11 0.072(2) 0.063(2) 0.0386(15) -0.0040(14) 0.0087(14) -0.0170(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C5 1.327(3) . ? N1 C1 1.332(3) . ? N1 H1A 0.95(2) . ? C1 C2 1.370(3) . ? C1 H1 0.9400 . ? C2 C3 1.397(3) . ? C2 H2 0.9400 . ? C3 C4 1.392(3) . ? C3 C8 1.485(3) . ? C4 C5 1.387(3) . ? C4 H4 0.9400 . ? C5 H5 0.9400 . ? N2 C6 1.341(3) . ? N2 C10 1.344(2) . ? N2 H2A 0.99(2) . ? C6 C7 1.376(3) . ? C6 H6 0.9400 . ? C7 C8 1.403(2) . ? C7 H7 0.9400 . ? C8 C9 1.395(3) . ? C9 C10 1.375(3) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? P1 O4 1.4692(16) . ? P1 O3 1.4961(16) . ? P1 O2 1.6283(17) . ? P1 O1 1.6359(18) . ? O1 C11 1.406(2) . ? O2 C21 1.410(2) . ? C11 C20 1.384(2) . ? C11 C12 1.411(3) . ? C12 C13 1.365(3) . ? C12 H12 0.9400 . ? C13 C14 1.417(3) . ? C13 H13 0.9400 . ? C14 C15 1.421(3) . ? C14 C19 1.435(2) . ? C15 C16 1.371(3) . ? C15 H15 0.9400 . ? C16 C17 1.411(3) . ? C16 H16 0.9400 . ? C17 C18 1.366(3) . ? C17 H17 0.9400 . ? C18 C19 1.425(3) . ? C18 H18 0.9400 . ? C19 C20 1.435(2) . ? C20 C30 1.501(2) . ? C21 C30 1.382(3) . ? C21 C22 1.408(3) . ? C22 C23 1.366(3) . ? C22 H22 0.9400 . ? C23 C24 1.424(3) . ? C23 H23 0.9400 . ? C24 C25 1.426(3) . ? C24 C29 1.438(3) . ? C25 C26 1.366(3) . ? C25 H25 0.9400 . ? C26 C27 1.411(3) . ? C26 H26 0.9400 . ? C27 C28 1.371(3) . ? C27 H27 0.9400 . ? C28 C29 1.423(3) . ? C28 H28 0.9400 . ? C29 C30 1.446(2) . ? P2 O7 1.4764(17) . ? P2 O8 1.4890(16) . ? P2 O6 1.6313(17) . ? P2 O5 1.6351(16) . ? O5 C31 1.400(2) . ? O6 C41 1.407(2) . ? C31 C40 1.385(2) . ? C31 C32 1.405(2) . ? C32 C33 1.364(3) . ? C32 H32 0.9400 . ? C33 C34 1.417(3) . ? C33 H33 0.9400 . ? C34 C35 1.423(3) . ? C34 C39 1.428(3) . ? C35 C36 1.353(3) . ? C35 H35 0.9400 . ? C36 C37 1.406(3) . ? C36 H36 0.9400 . ? C37 C38 1.378(3) . ? C37 H37 0.9400 . ? C38 C39 1.426(3) . ? C38 H38 0.9400 . ? C39 C40 1.441(2) . ? C40 C50 1.499(2) . ? C41 C50 1.383(2) . ? C41 C42 1.405(2) . ? C42 C43 1.361(3) . ? C42 H42 0.9400 . ? C43 C44 1.420(3) . ? C43 H43 0.9400 . ? C44 C45 1.426(3) . ? C44 C49 1.428(2) . ? C45 C46 1.365(3) . ? C45 H45 0.9400 . ? C46 C47 1.404(3) . ? C46 H46 0.9400 . ? C47 C48 1.372(3) . ? C47 H47 0.9400 . ? C48 C49 1.424(2) . ? C48 H48 0.9400 . ? C49 C50 1.440(2) . ? O9 H9A 0.92(3) . ? O9 H9B 0.88(2) . ? O10 H10A 0.99(3) . ? O10 H10B 1.03(3) . ? O11 H11A 0.7993 . ? O11 H11B 0.8523 . ? 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 C5 N1 C1 122.47(18) . . ? C5 N1 H1A 122.0(14) . . ? C1 N1 H1A 115.3(14) . . ? N1 C1 C2 120.35(19) . . ? N1 C1 H1 119.8 . . ? C2 C1 H1 119.8 . . ? C1 C2 C3 119.3(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 118.90(18) . . ? C4 C3 C8 121.33(16) . . ? C2 C3 C8 119.76(17) . . ? C5 C4 C3 118.9(2) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 120.1(2) . . ? N1 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C6 N2 C10 121.68(16) . . ? C6 N2 H2A 122.6(12) . . ? C10 N2 H2A 115.7(12) . . ? N2 C6 C7 121.11(17) . . ? N2 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C8 118.42(19) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? C9 C8 C7 119.08(16) . . ? C9 C8 C3 120.23(16) . . ? C7 C8 C3 120.65(18) . . ? C10 C9 C8 119.68(17) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? N2 C10 C9 120.00(19) . . ? N2 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? O4 P1 O3 121.30(10) . . ? O4 P1 O2 106.19(8) . . ? O3 P1 O2 109.82(9) . . ? O4 P1 O1 113.32(8) . . ? O3 P1 O1 102.92(7) . . ? O2 P1 O1 101.62(9) . . ? C11 O1 P1 119.18(11) . . ? C21 O2 P1 116.44(11) . . ? C20 C11 O1 118.87(16) . . ? C20 C11 C12 123.35(16) . . ? O1 C11 C12 117.76(15) . . ? C13 C12 C11 119.24(16) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 120.82(17) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C15 120.96(17) . . ? C13 C14 C19 119.53(16) . . ? C15 C14 C19 119.50(16) . . ? C16 C15 C14 120.79(18) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 119.87(17) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 120.95(18) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 121.15(18) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C14 117.70(15) . . ? C18 C19 C20 122.79(16) . . ? C14 C19 C20 119.48(15) . . ? C11 C20 C19 117.50(16) . . ? C11 C20 C30 119.31(15) . . ? C19 C20 C30 123.11(15) . . ? C30 C21 C22 123.55(16) . . ? C30 C21 O2 119.11(15) . . ? C22 C21 O2 117.33(16) . . ? C23 C22 C21 119.38(18) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 120.71(17) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C23 C24 C25 121.97(17) . . ? C23 C24 C29 119.58(16) . . ? C25 C24 C29 118.42(18) . . ? C26 C25 C24 121.57(19) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C25 C26 C27 119.84(18) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C28 C27 C26 120.7(2) . . ? C28 C27 H27 119.6 . . ? C26 C27 H27 119.6 . . ? C27 C28 C29 121.12(19) . . ? C27 C28 H28 119.4 . . ? C29 C28 H28 119.4 . . ? C28 C29 C24 118.29(16) . . ? C28 C29 C30 122.56(16) . . ? C24 C29 C30 119.04(17) . . ? C21 C30 C29 117.53(16) . . ? C21 C30 C20 119.81(15) . . ? C29 C30 C20 122.58(16) . . ? O7 P2 O8 120.90(7) . . ? O7 P2 O6 105.90(9) . . ? O8 P2 O6 111.51(8) . . ? O7 P2 O5 111.78(7) . . ? O8 P2 O5 103.47(10) . . ? O6 P2 O5 101.72(8) . . ? C31 O5 P2 117.25(12) . . ? C41 O6 P2 116.74(11) . . ? C40 C31 O5 119.37(14) . . ? C40 C31 C32 123.44(16) . . ? O5 C31 C32 117.16(15) . . ? C33 C32 C31 119.05(18) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C32 C33 C34 120.88(16) . . ? C32 C33 H33 119.6 . . ? C34 C33 H33 119.6 . . ? C33 C34 C35 121.26(18) . . ? C33 C34 C39 120.00(16) . . ? C35 C34 C39 118.73(19) . . ? C36 C35 C34 121.2(2) . . ? C36 C35 H35 119.4 . . ? C34 C35 H35 119.4 . . ? C35 C36 C37 120.90(19) . . ? C35 C36 H36 119.5 . . ? C37 C36 H36 119.5 . . ? C38 C37 C36 120.0(2) . . ? C38 C37 H37 120.0 . . ? C36 C37 H37 120.0 . . ? C37 C38 C39 120.85(19) . . ? C37 C38 H38 119.6 . . ? C39 C38 H38 119.6 . . ? C38 C39 C34 118.36(16) . . ? C38 C39 C40 122.78(16) . . ? C34 C39 C40 118.83(16) . . ? C31 C40 C39 117.67(14) . . ? C31 C40 C50 119.13(15) . . ? C39 C40 C50 123.11(15) . . ? C50 C41 C42 123.36(16) . . ? C50 C41 O6 118.86(14) . . ? C42 C41 O6 117.78(15) . . ? C43 C42 C41 118.97(17) . . ? C43 C42 H42 120.5 . . ? C41 C42 H42 120.5 . . ? C42 C43 C44 121.15(16) . . ? C42 C43 H43 119.4 . . ? C44 C43 H43 119.4 . . ? C43 C44 C45 121.38(16) . . ? C43 C44 C49 119.55(16) . . ? C45 C44 C49 119.04(17) . . ? C46 C45 C44 121.17(17) . . ? C46 C45 H45 119.4 . . ? C44 C45 H45 119.4 . . ? C45 C46 C47 119.99(18) . . ? C45 C46 H46 120.0 . . ? C47 C46 H46 120.0 . . ? C48 C47 C46 120.66(18) . . ? C48 C47 H47 119.7 . . ? C46 C47 H47 119.7 . . ? C47 C48 C49 121.24(17) . . ? C47 C48 H48 119.4 . . ? C49 C48 H48 119.4 . . ? C48 C49 C44 117.90(16) . . ? C48 C49 C50 123.03(15) . . ? C44 C49 C50 118.98(15) . . ? C41 C50 C49 117.73(14) . . ? C41 C50 C40 119.07(15) . . ? C49 C50 C40 123.04(14) . . ? H9A O9 H9B 100(2) . . ? H10A O10 H10B 104(2) . . ? H11A O11 H11B 126.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O8 0.95(2) 1.74(2) 2.686(3) 179(2) . N2 H2A O3 0.99(2) 1.62(2) 2.606(3) 173.1(19) . O9 H9A O7 0.92(3) 1.92(3) 2.801(3) 160(2) . O9 H9B O8 0.88(2) 1.97(3) 2.786(3) 154(2) 3_666 O10 H10A O9 0.99(3) 1.98(3) 2.942(3) 166(2) 2_545 O10 H10B O3 1.03(3) 1.84(3) 2.864(3) 175(2) . O11 H11A O4 0.80 2.02 2.798(3) 163.7 . O11 H11B O4 0.85 1.94 2.789(4) 179.6 3_455 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 26.60 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.232 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.043 # Attachment '5_isoquino-Cl.cif' data_d1 _database_code_depnum_ccdc_archive 'CCDC 276031' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6,6'-diisoquinolin-2,2'-ium dichloride dihydrate ; _chemical_name_common "6,6'-diisoquinolin-2,2'-ium dichloride dihydrate" _chemical_melting_point ? _chemical_formula_moiety '(C18 H14 N2), Cl2, 2(H2 O)' _chemical_formula_sum 'C18 H18 Cl2 N2 O2' _chemical_formula_weight 365.24 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9715(19) _cell_length_b 9.162(4) _cell_length_c 10.233(4) _cell_angle_alpha 109.757(7) _cell_angle_beta 92.325(7) _cell_angle_gamma 98.082(7) _cell_volume 432.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 207(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 190 _exptl_absorpt_coefficient_mu 0.388 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9334 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 207(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD area detector' _diffrn_measurement_method \\w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3520 _diffrn_reflns_av_R_equivalents 0.2267 _diffrn_reflns_av_sigmaI/netI 0.2438 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.20 _reflns_number_total 1725 _reflns_number_gt 768 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 1997a)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The protic hydrogen atoms on N (diisoquinoline) and one of the H-atoms on O (water) were found and refined with Ueq(H) = 1.5 Ueq(N/O). The other H-atom of the water molecule was disordered and two positions (H1B, H1C) were found but had to be fixed upon further refinement. Hydrogen atoms on C (diisoquinoline) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C). ; _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.020(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\\l^3^/sin(2\\q)]^-1/4^ _refine_ls_number_reflns 1725 _refine_ls_number_parameters 116 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1561 _refine_ls_R_factor_gt 0.0686 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 0.815 _refine_ls_restrained_S_all 0.815 _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 Cl Cl 0.1306(2) 0.71098(15) 0.87065(15) 0.0489(5) Uani 1 1 d . . . O O 0.2591(9) 0.5452(6) 0.5561(5) 0.0898(16) Uani 1 1 d D . . H1A H 0.230(13) 0.568(9) 0.659(7) 0.135 Uiso 1 1 d D . . H1B H 0.4060 0.5179 0.5224 0.135 Uiso 0.50 1 d P . . H1C H 0.1043 0.5179 0.5224 0.135 Uiso 0.50 1 d P . . N N -0.2624(7) 0.7649(5) 1.0931(4) 0.0397(11) Uani 1 1 d . . . H H -0.144(9) 0.745(6) 1.017(6) 0.060 Uiso 1 1 d . . . C1 C -0.3567(8) 0.8984(6) 1.1325(5) 0.0387(12) Uani 1 1 d . . . H1 H -0.2992 0.9740 1.0919 0.046 Uiso 1 1 calc R . . C2 C -0.5410(8) 0.9299(5) 1.2340(5) 0.0359(12) Uani 1 1 d . . . C3 C -0.6479(8) 1.0709(5) 1.2798(6) 0.0411(12) Uani 1 1 d . . . H3 H -0.5971 1.1483 1.2401 0.049 Uiso 1 1 calc R . . C4 C -0.8231(8) 1.0971(5) 1.3801(5) 0.0410(12) Uani 1 1 d . . . H4 H -0.8917 1.1924 1.4086 0.049 Uiso 1 1 calc R . . C5 C -0.9058(7) 0.9830(5) 1.4437(5) 0.0333(12) Uani 1 1 d . . . C5N C -0.8100(7) 0.8427(5) 1.3965(5) 0.0372(12) Uani 1 1 d . . . H5N H -0.8677 0.7652 1.4351 0.045 Uiso 1 1 calc R . . C6 C -0.6272(8) 0.8108(6) 1.2916(5) 0.0367(12) Uani 1 1 d . . . C7 C -0.5226(9) 0.6703(6) 1.2433(6) 0.0466(13) Uani 1 1 d . . . H7 H -0.5784 0.5906 1.2796 0.056 Uiso 1 1 calc R . . C8 C -0.3421(9) 0.6464(6) 1.1451(6) 0.0466(13) Uani 1 1 d . . . H8 H -0.2729 0.5513 1.1133 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl 0.0478(7) 0.0445(8) 0.0561(8) 0.0173(6) 0.0219(6) 0.0087(5) O 0.084(3) 0.103(4) 0.068(3) 0.014(3) 0.014(2) 0.008(2) N 0.030(2) 0.042(3) 0.043(3) 0.010(2) 0.0133(18) 0.0040(18) C1 0.028(2) 0.040(3) 0.045(3) 0.013(3) 0.008(2) 0.002(2) C2 0.031(2) 0.036(3) 0.039(3) 0.011(2) 0.008(2) 0.0031(19) C3 0.042(3) 0.030(3) 0.051(3) 0.015(3) 0.016(2) 0.002(2) C4 0.040(3) 0.033(3) 0.052(3) 0.014(3) 0.016(2) 0.010(2) C5 0.026(2) 0.032(3) 0.035(3) 0.005(2) 0.0042(19) -0.003(2) C5N 0.033(2) 0.029(3) 0.048(3) 0.013(2) 0.011(2) -0.001(2) C6 0.028(2) 0.038(3) 0.042(3) 0.012(2) 0.004(2) 0.005(2) C7 0.051(3) 0.036(3) 0.054(4) 0.015(3) 0.020(3) 0.011(2) C8 0.046(3) 0.038(3) 0.056(3) 0.013(3) 0.012(3) 0.011(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 O H1A 1.03(6) . ? O H1B 0.8534 . ? O H1C 0.8001 . ? N C1 1.312(6) . ? N C8 1.381(6) . ? N H 0.98(5) . ? C1 C2 1.396(6) . ? C1 H1 0.9400 . ? C2 C3 1.405(6) . ? C2 C6 1.430(6) . ? C3 C4 1.355(6) . ? C3 H3 0.9400 . ? C4 C5 1.430(6) . ? C4 H4 0.9400 . ? C5 C5N 1.372(6) . ? C5 C5 1.493(8) 2_378 ? C5N C6 1.416(6) . ? C5N H5N 0.9400 . ? C6 C7 1.397(7) . ? C7 C8 1.357(6) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? 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 H1A O H1B 122.4 . . ? H1A O H1C 100.0 . . ? H1B O H1C 130.2 . . ? C1 N C8 123.0(4) . . ? C1 N H 118(3) . . ? C8 N H 119(3) . . ? N C1 C2 121.0(4) . . ? N C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 123.2(4) . . ? C1 C2 C6 117.8(4) . . ? C3 C2 C6 119.0(4) . . ? C4 C3 C2 121.1(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 121.5(4) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C5N C5 C4 117.9(4) . . ? C5N C5 C5 121.9(5) . 2_378 ? C4 C5 C5 120.1(5) . 2_378 ? C5 C5N C6 122.2(4) . . ? C5 C5N H5N 118.9 . . ? C6 C5N H5N 118.9 . . ? C7 C6 C5N 123.5(4) . . ? C7 C6 C2 118.3(4) . . ? C5N C6 C2 118.3(4) . . ? C8 C7 C6 121.5(5) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 N 118.4(5) . . ? C7 C8 H8 120.8 . . ? N C8 H8 120.8 . . ? 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 C8 N C1 C2 1.7(7) . . . . ? N C1 C2 C3 -180.0(5) . . . . ? N C1 C2 C6 -1.1(7) . . . . ? C1 C2 C3 C4 -178.9(4) . . . . ? C6 C2 C3 C4 2.2(7) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? C3 C4 C5 C5N -2.3(7) . . . . ? C3 C4 C5 C5 178.6(5) . . . 2_378 ? C4 C5 C5N C6 2.1(7) . . . . ? C5 C5 C5N C6 -178.8(4) 2_378 . . . ? C5 C5N C6 C7 178.8(5) . . . . ? C5 C5N C6 C2 0.1(7) . . . . ? C1 C2 C6 C7 0.0(7) . . . . ? C3 C2 C6 C7 178.9(5) . . . . ? C1 C2 C6 C5N 178.8(4) . . . . ? C3 C2 C6 C5N -2.3(6) . . . . ? C5N C6 C7 C8 -178.2(4) . . . . ? C2 C6 C7 C8 0.5(7) . . . . ? C6 C7 C8 N 0.0(8) . . . . ? C1 N C8 C7 -1.2(7) . . . . ? 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 N H Cl 0.98(5) 2.04(5) 3.019(4) 175(4) . O H1A Cl 1.03(6) 2.23(7) 3.195(5) 155(7) . O H1B O 0.85 1.95 2.807(10) 179.6 2_666 O H1C O 0.80 1.88 2.676(9) 179.7 2_566 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.20 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.329 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.078 data_dorn1 _database_code_depnum_ccdc_archive 'CCDC 276032' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2'-bi-1,6-naphthyridin-6,6'-ium-dichloride dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Cl2 N4 O2' _chemical_formula_weight 367.23 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9382(6) _cell_length_b 9.1344(11) _cell_length_c 10.2335(12) _cell_angle_alpha 110.667(2) _cell_angle_beta 91.904(2) _cell_angle_gamma 98.093(2) _cell_volume 425.88(9) _cell_formula_units_Z 1 _cell_measurement_temperature 205(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 190 _exptl_absorpt_coefficient_mu 0.398 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8571 _exptl_absorpt_correction_T_max 0.8571 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 205(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD area detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3470 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 26.39 _reflns_number_total 1724 _reflns_number_gt 1500 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 1997a)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The protic hydrogen atoms on 6,6'-N (binaphthyridine) and one of the H-atoms on O (water) were found and refined with Ueq(H) = 1.5 Ueq(N/O). The other H-atom of the water molecule was disordered and two positions (H1B, H1C) were found but had to be fixed upon further refinement. Hydrogen atoms on C (binaphthyridine) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C). ; _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^)+(0.0640P)^2^+0.0151P] 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 1724 _refine_ls_number_parameters 115 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N -0.2671(3) 0.76668(16) 1.10280(14) 0.0367(3) Uani 1 1 d . . . H H -0.151(5) 0.741(3) 1.034(2) 0.055 Uiso 1 1 d . . . C1 C -0.3561(3) 0.90329(19) 1.14054(15) 0.0356(3) Uani 1 1 d . . . H1 H -0.2928 0.9772 1.0992 0.043 Uiso 1 1 calc R . . C2 C -0.5457(3) 0.93983(18) 1.24243(14) 0.0313(3) Uani 1 1 d . . . C3 C -0.6465(3) 1.08495(18) 1.28893(16) 0.0363(4) Uani 1 1 d . . . H3 H -0.5913 1.1631 1.2509 0.044 Uiso 1 1 calc R . . C4 C -0.8255(3) 1.10976(18) 1.39016(17) 0.0351(3) Uani 1 1 d . . . H4 H -0.8959 1.2054 1.4237 0.042 Uiso 1 1 calc R . . C5 C -0.9031(3) 0.98744(17) 1.44389(14) 0.0291(3) Uani 1 1 d . . . N2 N -0.8168(3) 0.84977(15) 1.40146(13) 0.0318(3) Uani 1 1 d . . . C6 C -0.6381(3) 0.82382(17) 1.30004(15) 0.0309(3) Uani 1 1 d . . . C7 C -0.5400(3) 0.6775(2) 1.25280(17) 0.0400(4) Uani 1 1 d . . . H7 H -0.6027 0.5983 1.2886 0.048 Uiso 1 1 calc R . . C8 C -0.3548(3) 0.6521(2) 1.15553(17) 0.0397(4) Uani 1 1 d . . . H8 H -0.2870 0.5555 1.1244 0.048 Uiso 1 1 calc R . . Cl Cl 0.13495(8) 0.71831(5) 0.88410(4) 0.04154(17) Uani 1 1 d . . . O O 0.2591(4) 0.5264(2) 0.56324(17) 0.0739(5) Uani 1 1 d . . . H1A H 0.236(7) 0.585(4) 0.650(3) 0.111 Uiso 1 1 d . . . H1B H 0.0937 0.5268 0.5065 0.111 Uiso 0.50 1 d P . . H1C H 0.4408 0.5516 0.5397 0.111 Uiso 0.50 1 d P . . 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 N1 0.0323(7) 0.0447(8) 0.0299(7) 0.0082(6) 0.0087(5) 0.0088(6) C1 0.0342(8) 0.0402(8) 0.0314(8) 0.0118(7) 0.0073(6) 0.0053(6) C2 0.0288(7) 0.0351(8) 0.0279(7) 0.0093(6) 0.0043(6) 0.0034(6) C3 0.0409(8) 0.0333(8) 0.0375(8) 0.0156(7) 0.0112(6) 0.0055(6) C4 0.0400(8) 0.0291(7) 0.0372(8) 0.0116(6) 0.0106(6) 0.0078(6) C5 0.0279(7) 0.0315(7) 0.0257(7) 0.0080(6) 0.0030(6) 0.0037(5) N2 0.0321(6) 0.0336(6) 0.0308(6) 0.0118(5) 0.0080(5) 0.0069(5) C6 0.0294(7) 0.0335(8) 0.0292(7) 0.0101(6) 0.0039(6) 0.0055(6) C7 0.0439(9) 0.0376(8) 0.0420(9) 0.0159(7) 0.0119(7) 0.0119(7) C8 0.0412(9) 0.0371(8) 0.0405(9) 0.0104(7) 0.0093(7) 0.0142(7) Cl 0.0474(3) 0.0413(2) 0.0391(3) 0.01492(18) 0.01787(17) 0.01305(17) O 0.0818(11) 0.0784(11) 0.0511(9) 0.0093(8) 0.0074(8) 0.0164(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 N1 C1 1.313(2) . ? N1 C8 1.364(2) . ? N1 H 0.91(2) . ? C1 C2 1.408(2) . ? C1 H1 0.9400 . ? C2 C3 1.410(2) . ? C2 C6 1.415(2) . ? C3 C4 1.363(2) . ? C3 H3 0.9400 . ? C4 C5 1.423(2) . ? C4 H4 0.9400 . ? C5 N2 1.315(2) . ? C5 C5 1.495(3) 2_378 ? N2 C6 1.3634(19) . ? C6 C7 1.413(2) . ? C7 C8 1.356(2) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? O H1A 0.88(3) . ? O H1B 0.9874 . ? O H1C 0.9546 . ? 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 C1 N1 C8 123.05(14) . . ? C1 N1 H 120.8(14) . . ? C8 N1 H 116.0(14) . . ? N1 C1 C2 120.50(14) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C1 C2 C3 123.33(14) . . ? C1 C2 C6 117.65(14) . . ? C3 C2 C6 119.01(13) . . ? C4 C3 C2 118.69(14) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 118.40(14) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N2 C5 C4 124.57(14) . . ? N2 C5 C5 116.04(16) . 2_378 ? C4 C5 C5 119.39(16) . 2_378 ? C5 N2 C6 117.43(13) . . ? N2 C6 C7 118.83(14) . . ? N2 C6 C2 121.88(14) . . ? C7 C6 C2 119.28(14) . . ? C8 C7 C6 119.50(16) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 N1 119.98(15) . . ? C7 C8 H8 120.0 . . ? N1 C8 H8 120.0 . . ? H1A O H1B 105.4 . . ? H1A O H1C 111.9 . . ? H1B O H1C 122.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H Cl 0.91(2) 2.10(2) 2.9982(14) 171(2) . O H1A Cl 0.88(3) 2.38(3) 3.2563(16) 174(3) . O H1B O 0.99 1.79 2.729(4) 156.9 2_566 O H1C O 0.95 1.92 2.767(4) 146.6 2_666 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.244 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.050 data_abu1 _database_code_depnum_ccdc_archive 'CCDC 276033' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,4'-bipyridin-1,1'-ium bis(dihydrogenphosphate) dihydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2, 2(H2 P O4), 2(H2 O)' _chemical_formula_sum 'C10 H18 N2 O10 P2' _chemical_formula_weight 388.20 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 P21/c 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 18.9374(18) _cell_length_b 9.0233(9) _cell_length_c 9.4739(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.801(2) _cell_angle_gamma 90.00 _cell_volume 1616.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 205(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless-white _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.324 _exptl_absorpt_correction_type Multiscan _exptl_absorpt_correction_T_min 0.8547 _exptl_absorpt_correction_T_max 0.8813 _exptl_absorpt_process_details 'SADABS (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 205(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS CCD area detector' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9392 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3556 _reflns_number_gt 2360 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker 1997a)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The protic hydrogen atoms on N (bipyridine) and O (water and phosphate) were found and refined with Ueq(H) = 1.5 Ueq(N/O). Hydrogen atoms on C (bipyridine) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C). ; _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^)+(0.0647P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3556 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0409 _refine_ls_wR_factor_ref 0.1148 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 0.941 _refine_ls_restrained_S_all 0.941 _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 N1 N 0.10967(10) 0.7864(2) 0.0045(2) 0.0362(5) Uani 1 1 d . . . H1 H 0.0708(14) 0.811(3) -0.069(3) 0.054 Uiso 1 1 d . . . N2 N 0.39310(9) 0.6768(2) 0.48943(19) 0.0313(4) Uani 1 1 d . . . H2 H 0.4305(13) 0.654(3) 0.554(3) 0.047 Uiso 1 1 d . . . C1 C 0.13496(12) 0.6500(3) 0.0252(2) 0.0388(6) Uani 1 1 d . . . H1A H 0.1147 0.5702 -0.0261 0.047 Uiso 1 1 calc R . . C2 C 0.19068(11) 0.6250(3) 0.1212(2) 0.0349(5) Uani 1 1 d . . . H2A H 0.2089 0.5289 0.1348 0.042 Uiso 1 1 calc R . . C3 C 0.21967(11) 0.7439(2) 0.1981(2) 0.0276(5) Uani 1 1 d . . . C4 C 0.19097(12) 0.8834(3) 0.1759(2) 0.0361(5) Uani 1 1 d . . . H4 H 0.2089 0.9650 0.2278 0.043 Uiso 1 1 calc R . . C5 C 0.13563(12) 0.9019(3) 0.0766(3) 0.0399(6) Uani 1 1 d . . . H5 H 0.1163 0.9967 0.0602 0.048 Uiso 1 1 calc R . . C6 C 0.35276(11) 0.5622(3) 0.4515(2) 0.0337(5) Uani 1 1 d . . . H6 H 0.3633 0.4677 0.4887 0.040 Uiso 1 1 calc R . . C7 C 0.29543(11) 0.5809(3) 0.3577(2) 0.0334(5) Uani 1 1 d . . . H7 H 0.2666 0.4996 0.3316 0.040 Uiso 1 1 calc R . . C8 C 0.28053(11) 0.7203(2) 0.3019(2) 0.0265(5) Uani 1 1 d . . . C9 C 0.38030(12) 0.8122(3) 0.4385(2) 0.0367(6) Uani 1 1 d . . . H9 H 0.4101 0.8912 0.4671 0.044 Uiso 1 1 calc R . . C10 C 0.32427(11) 0.8376(3) 0.3450(2) 0.0345(5) Uani 1 1 d . . . H10 H 0.3153 0.9336 0.3101 0.041 Uiso 1 1 calc R . . P1 P 0.53812(3) 0.78370(6) 0.71219(5) 0.02352(16) Uani 1 1 d . . . O11 O 0.57718(8) 0.78175(18) 0.85216(14) 0.0318(4) Uani 1 1 d . . . O12 O 0.50351(7) 0.64022(16) 0.66265(15) 0.0295(3) Uani 1 1 d . . . O13 O 0.47628(9) 0.89790(19) 0.70742(18) 0.0442(5) Uani 1 1 d . . . H13 H 0.4826(14) 0.987(4) 0.756(3) 0.066 Uiso 1 1 d . . . O14 O 0.59162(9) 0.8346(2) 0.60187(16) 0.0415(5) Uani 1 1 d . . . H14 H 0.5825(16) 0.803(3) 0.535(3) 0.062 Uiso 1 1 d . . . P2 P -0.04075(3) 0.69623(6) -0.21463(6) 0.02721(17) Uani 1 1 d . . . O21 O -0.07745(8) 0.68856(19) -0.35713(15) 0.0379(4) Uani 1 1 d . . . O22 O 0.00898(9) 0.8244(2) -0.18674(19) 0.0493(5) Uani 1 1 d . . . O23 O 0.00538(11) 0.5583(2) -0.1794(2) 0.0662(6) Uani 1 1 d . . . H23 H -0.0049(16) 0.468(4) -0.228(3) 0.099 Uiso 1 1 d . . . O24 O -0.09897(9) 0.7008(2) -0.10597(18) 0.0540(6) Uani 1 1 d . . . H24 H -0.0874(17) 0.734(4) -0.028(3) 0.081 Uiso 1 1 d . . . O1 O 0.72169(10) 0.7289(3) 0.8771(2) 0.0731(8) Uani 1 1 d . . . H1B H 0.7389(19) 0.761(4) 0.809(4) 0.110 Uiso 1 1 d . . . H1C H 0.677(2) 0.738(4) 0.872(4) 0.110 Uiso 1 1 d . . . O2 O 0.78413(10) 0.8071(3) 0.6375(2) 0.0563(6) Uani 1 1 d . . . H2B H 0.8230(19) 0.748(4) 0.634(4) 0.084 Uiso 1 1 d . . . H2C H 0.7634(16) 0.789(4) 0.549(4) 0.084 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 N1 0.0271(10) 0.0485(13) 0.0321(10) 0.0091(9) -0.0073(8) -0.0022(9) N2 0.0281(10) 0.0377(11) 0.0272(10) 0.0036(8) -0.0076(8) 0.0000(8) C1 0.0371(13) 0.0424(14) 0.0356(13) 0.0046(11) -0.0110(10) -0.0077(11) C2 0.0354(12) 0.0323(13) 0.0357(12) 0.0023(10) -0.0101(10) -0.0008(10) C3 0.0264(11) 0.0328(12) 0.0235(10) 0.0012(9) -0.0018(9) -0.0009(9) C4 0.0358(12) 0.0347(13) 0.0369(13) -0.0003(10) -0.0068(10) 0.0032(10) C5 0.0348(13) 0.0406(15) 0.0433(14) 0.0061(11) -0.0071(10) 0.0059(11) C6 0.0364(12) 0.0311(12) 0.0329(12) 0.0034(10) -0.0072(10) 0.0027(10) C7 0.0331(12) 0.0315(12) 0.0348(12) 0.0006(10) -0.0078(9) -0.0031(10) C8 0.0247(11) 0.0316(12) 0.0229(10) -0.0001(9) -0.0014(8) 0.0008(9) C9 0.0381(13) 0.0346(13) 0.0363(13) 0.0035(10) -0.0109(10) -0.0087(10) C10 0.0362(12) 0.0315(12) 0.0348(12) 0.0047(10) -0.0096(10) -0.0027(10) P1 0.0256(3) 0.0256(3) 0.0188(3) -0.0002(2) -0.0037(2) -0.0006(2) O11 0.0329(8) 0.0421(10) 0.0196(7) 0.0012(6) -0.0063(6) -0.0014(7) O12 0.0316(8) 0.0248(8) 0.0311(8) 0.0042(6) -0.0084(6) -0.0042(6) O13 0.0419(10) 0.0381(10) 0.0504(10) -0.0190(8) -0.0206(8) 0.0142(8) O14 0.0518(11) 0.0500(11) 0.0228(8) -0.0066(8) 0.0051(8) -0.0233(9) P2 0.0308(3) 0.0293(3) 0.0209(3) 0.0013(2) -0.0056(2) -0.0010(2) O21 0.0391(9) 0.0528(11) 0.0212(8) 0.0045(7) -0.0060(7) -0.0021(8) O22 0.0442(10) 0.0469(11) 0.0542(11) 0.0259(9) -0.0252(8) -0.0199(8) O23 0.0917(15) 0.0419(12) 0.0601(12) -0.0213(10) -0.0459(11) 0.0249(11) O24 0.0397(10) 0.0950(17) 0.0276(9) -0.0180(10) 0.0039(8) -0.0177(10) O1 0.0305(10) 0.149(3) 0.0390(12) 0.0185(13) -0.0012(9) 0.0053(13) O2 0.0353(10) 0.0988(18) 0.0345(10) -0.0055(10) -0.0022(8) 0.0077(10) _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 N1 C5 1.328(3) . ? N1 C1 1.332(3) . ? N1 H1 1.01(3) . ? N2 C6 1.325(3) . ? N2 C9 1.332(3) . ? N2 H2 0.94(3) . ? C1 C2 1.378(3) . ? C1 H1A 0.9400 . ? C2 C3 1.395(3) . ? C2 H2A 0.9400 . ? C3 C4 1.383(3) . ? C3 C8 1.493(3) . ? C4 C5 1.383(3) . ? C4 H4 0.9400 . ? C5 H5 0.9400 . ? C6 C7 1.380(3) . ? C6 H6 0.9400 . ? C7 C8 1.389(3) . ? C7 H7 0.9400 . ? C8 C10 1.393(3) . ? C9 C10 1.368(3) . ? C9 H9 0.9400 . ? C10 H10 0.9400 . ? P1 O11 1.4866(14) . ? P1 O12 1.5152(15) . ? P1 O13 1.5589(16) . ? P1 O14 1.5598(17) . ? O13 H13 0.93(3) . ? O14 H14 0.71(3) . ? P2 O21 1.4895(15) . ? P2 O22 1.5067(16) . ? P2 O24 1.5453(18) . ? P2 O23 1.5473(19) . ? O23 H23 0.95(4) . ? O24 H24 0.82(3) . ? O1 H1B 0.79(4) . ? O1 H1C 0.85(4) . ? O2 H2B 0.91(4) . ? O2 H2C 0.92(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 C5 N1 C1 121.9(2) . . ? C5 N1 H1 115.0(15) . . ? C1 N1 H1 123.1(15) . . ? C6 N2 C9 121.71(19) . . ? C6 N2 H2 114.6(16) . . ? C9 N2 H2 123.7(16) . . ? N1 C1 C2 120.4(2) . . ? N1 C1 H1A 119.8 . . ? C2 C1 H1A 119.8 . . ? C1 C2 C3 119.2(2) . . ? C1 C2 H2A 120.4 . . ? C3 C2 H2A 120.4 . . ? C4 C3 C2 118.6(2) . . ? C4 C3 C8 121.0(2) . . ? C2 C3 C8 120.4(2) . . ? C3 C4 C5 119.5(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 120.3(2) . . ? N1 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? N2 C6 C7 120.3(2) . . ? N2 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C8 119.6(2) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C7 C8 C10 118.04(19) . . ? C7 C8 C3 121.0(2) . . ? C10 C8 C3 120.9(2) . . ? N2 C9 C10 120.7(2) . . ? N2 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C8 119.6(2) . . ? C9 C10 H10 120.2 . . ? C8 C10 H10 120.2 . . ? O11 P1 O12 117.06(9) . . ? O11 P1 O13 111.96(9) . . ? O12 P1 O13 104.06(9) . . ? O11 P1 O14 106.86(9) . . ? O12 P1 O14 109.22(9) . . ? O13 P1 O14 107.31(11) . . ? P1 O13 H13 118.5(17) . . ? P1 O14 H14 110(2) . . ? O21 P2 O22 117.04(10) . . ? O21 P2 O24 106.77(9) . . ? O22 P2 O24 108.83(11) . . ? O21 P2 O23 113.07(10) . . ? O22 P2 O23 103.76(11) . . ? O24 P2 O23 106.95(13) . . ? P2 O23 H23 118.9(19) . . ? P2 O24 H24 116(2) . . ? H1B O1 H1C 112(3) . . ? H2B O2 H2C 100(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 N1 H1 O22 1.01(3) 1.58(3) 2.588(2) 172(2) . N2 H2 O12 0.94(3) 1.69(3) 2.615(2) 171(2) . O13 H13 O12 0.93(3) 1.60(3) 2.529(2) 178(3) 2_656 O14 H14 O11 0.71(3) 1.89(3) 2.590(2) 169(3) 4_575 O23 H23 O22 0.95(4) 1.53(4) 2.471(2) 171(3) 2_544 O24 H24 O21 0.82(3) 1.76(3) 2.574(2) 171(3) 4_576 O1 H1B O2 0.79(4) 1.92(4) 2.704(3) 171(4) . O1 H1C O11 0.85(4) 1.93(4) 2.777(2) 173(4) . O2 H2B O21 0.91(4) 1.96(4) 2.829(2) 160(3) 1_656 O2 H2C O1 0.92(4) 1.79(4) 2.703(3) 175(3) 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.464 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.076