# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Christoph Janiak' 'Anne-Christine Chamayou' 'Thomas Dorn' _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_requested_journal 'New Journal of Chemistry' _publ_section_title ; Hydrophilic interior between hydrophobic regions in inverse bilayer structures of cation-1,1'-binaphthalene-2,2'-diyl phosphate salts ; data_thomgm _database_code_depnum_ccdc_archive 'CCDC 286354' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (isonicotin-1-ium amide)(rac-1,1'-binaphthalene-2,2'-diyl phosphate).monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H21 N2 O6 P' _chemical_formula_weight 488.42 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.659(5) _cell_length_b 6.8903(12) _cell_length_c 24.209(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.548(3) _cell_angle_gamma 90.00 _cell_volume 4382.5(13) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description isometric _exptl_crystal_colour 'colorless to very light-yellow' _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 0.175 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9243 _exptl_absorpt_correction_T_max 0.9862 _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 18427 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.30 _reflns_number_total 4913 _reflns_number_gt 3247 _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 (isonicotinamide) and O (water) were found and refined with Ueq(H) = 1.5 Ueq(N/O). Hydrogen atoms on C (isonicotinamide 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^)+(0.0450P)^2^+2.9810P] 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 4913 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 P P 0.06523(2) 0.22723(8) 0.10841(2) 0.02331(14) Uani 1 1 d . . . O1 O 0.11998(5) 0.13958(19) 0.11828(6) 0.0254(3) Uani 1 1 d . . . O3 O 0.06177(6) 0.2173(2) 0.16760(6) 0.0306(3) Uani 1 1 d . . . O2 O 0.07170(5) 0.44969(19) 0.09065(6) 0.0225(3) Uani 1 1 d . . . O4 O 0.02412(6) 0.1463(2) 0.05386(6) 0.0302(3) Uani 1 1 d . . . C1 C 0.11789(7) 0.5451(3) 0.12173(8) 0.0208(4) Uani 1 1 d . . . C2 C 0.11822(8) 0.6885(3) 0.16288(9) 0.0244(4) Uani 1 1 d . . . H2 H 0.0888 0.7134 0.1698 0.029 Uiso 1 1 calc R . . C3 C 0.16124(8) 0.7909(3) 0.19256(9) 0.0268(5) Uani 1 1 d . . . H3 H 0.1613 0.8900 0.2193 0.032 Uiso 1 1 calc R . . C4 C 0.20626(8) 0.7504(3) 0.18387(9) 0.0253(4) Uani 1 1 d . . . C5 C 0.25188(9) 0.8511(3) 0.21682(9) 0.0330(5) Uani 1 1 d . . . H5 H 0.2515 0.9551 0.2418 0.040 Uiso 1 1 calc R . . C6 C 0.29647(9) 0.8000(4) 0.21307(10) 0.0375(6) Uani 1 1 d . . . H6 H 0.3266 0.8680 0.2355 0.045 Uiso 1 1 calc R . . C7 C 0.29732(9) 0.6456(3) 0.17562(10) 0.0341(5) Uani 1 1 d . . . H7 H 0.3283 0.6082 0.1739 0.041 Uiso 1 1 calc R . . C8 C 0.25343(8) 0.5489(3) 0.14160(9) 0.0277(5) Uani 1 1 d . . . H8 H 0.2546 0.4468 0.1164 0.033 Uiso 1 1 calc R . . C9 C 0.20632(7) 0.6000(3) 0.14367(8) 0.0221(4) Uani 1 1 d . . . C10 C 0.15986(7) 0.4991(3) 0.10994(8) 0.0209(4) Uani 1 1 d . . . C11 C 0.13618(8) 0.1655(3) 0.07149(9) 0.0227(4) Uani 1 1 d . . . C12 C 0.13072(8) 0.0093(3) 0.03262(9) 0.0277(5) Uani 1 1 d . . . H12 H 0.1182 -0.1104 0.0394 0.033 Uiso 1 1 calc R . . C13 C 0.14381(8) 0.0325(3) -0.01528(9) 0.0289(5) Uani 1 1 d . . . H13 H 0.1402 -0.0717 -0.0418 0.035 Uiso 1 1 calc R . . C14 C 0.16284(8) 0.2120(3) -0.02540(9) 0.0254(4) Uani 1 1 d . . . C15 C 0.17418(8) 0.2402(3) -0.07680(10) 0.0325(5) Uani 1 1 d . . . H15 H 0.1697 0.1368 -0.1038 0.039 Uiso 1 1 calc R . . C16 C 0.19146(9) 0.4137(4) -0.08773(10) 0.0368(6) Uani 1 1 d . . . H16 H 0.1992 0.4292 -0.1217 0.044 Uiso 1 1 calc R . . C17 C 0.19768(8) 0.5694(3) -0.04811(10) 0.0328(5) Uani 1 1 d . . . H17 H 0.2095 0.6893 -0.0558 0.039 Uiso 1 1 calc R . . C18 C 0.18674(8) 0.5490(3) 0.00163(9) 0.0258(4) Uani 1 1 d . . . H18 H 0.1908 0.6556 0.0274 0.031 Uiso 1 1 calc R . . C19 C 0.16933(7) 0.3692(3) 0.01503(9) 0.0221(4) Uani 1 1 d . . . C20 C 0.15615(7) 0.3424(3) 0.06584(8) 0.0212(4) Uani 1 1 d . . . N1 N 0.02588(7) 0.2320(3) -0.06328(9) 0.0397(5) Uani 1 1 d . . . H1 H 0.0166(10) 0.164(4) -0.0375(12) 0.060 Uiso 1 1 d . . . C21 C 0.02351(9) 0.1543(4) -0.11460(11) 0.0384(6) Uani 1 1 d . . . H21 H 0.0139 0.0238 -0.1236 0.046 Uiso 1 1 calc R . . C22 C 0.03515(8) 0.2650(3) -0.15436(10) 0.0303(5) Uani 1 1 d . . . H22 H 0.0331 0.2108 -0.1909 0.036 Uiso 1 1 calc R . . C23 C 0.04992(7) 0.4568(3) -0.14090(9) 0.0241(4) Uani 1 1 d . . . C24 C 0.05187(8) 0.5326(3) -0.08706(9) 0.0303(5) Uani 1 1 d . . . H24 H 0.0615 0.6625 -0.0768 0.036 Uiso 1 1 calc R . . C25 C 0.03956(9) 0.4157(4) -0.04879(10) 0.0379(6) Uani 1 1 d . . . H25 H 0.0408 0.4660 -0.0121 0.046 Uiso 1 1 calc R . . C26 C 0.06209(8) 0.5910(3) -0.18284(9) 0.0285(5) Uani 1 1 d . . . N2 N 0.06755(7) 0.5114(3) -0.22987(8) 0.0317(4) Uani 1 1 d . . . H2A H 0.0693(10) 0.381(4) -0.2346(11) 0.048 Uiso 1 1 d . . . H2B H 0.0708(9) 0.586(4) -0.2576(12) 0.048 Uiso 1 1 d . . . O5 O 0.06540(7) 0.7670(2) -0.17209(7) 0.0439(4) Uani 1 1 d . . . O6 O 0.07417(7) 1.0668(2) -0.24640(8) 0.0387(4) Uani 1 1 d . . . H6A H 0.0697(10) 0.996(4) -0.2783(13) 0.058 Uiso 1 1 d . . . H6B H 0.0723(10) 0.975(4) -0.2198(13) 0.058 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 P 0.0301(3) 0.0232(3) 0.0199(3) 0.0004(2) 0.0134(2) -0.0031(2) O1 0.0338(8) 0.0221(7) 0.0241(7) 0.0065(6) 0.0155(6) 0.0034(6) O3 0.0424(9) 0.0319(8) 0.0239(8) 0.0008(6) 0.0200(7) -0.0037(7) O2 0.0240(7) 0.0232(7) 0.0219(7) 0.0010(6) 0.0107(6) -0.0011(6) O4 0.0360(9) 0.0308(8) 0.0254(8) -0.0051(6) 0.0138(7) -0.0094(7) C1 0.0233(10) 0.0200(10) 0.0184(10) 0.0038(8) 0.0076(8) 0.0006(8) C2 0.0303(11) 0.0235(11) 0.0228(10) 0.0029(8) 0.0143(9) 0.0049(8) C3 0.0382(12) 0.0215(10) 0.0195(10) -0.0017(8) 0.0104(9) 0.0027(9) C4 0.0339(12) 0.0221(10) 0.0187(10) 0.0017(8) 0.0093(9) -0.0008(9) C5 0.0424(14) 0.0293(12) 0.0241(11) -0.0050(9) 0.0098(10) -0.0066(10) C6 0.0334(13) 0.0461(15) 0.0285(12) -0.0056(10) 0.0076(10) -0.0137(11) C7 0.0284(12) 0.0469(14) 0.0275(12) -0.0010(10) 0.0118(10) -0.0037(10) C8 0.0281(11) 0.0329(12) 0.0224(11) 0.0002(9) 0.0104(9) 0.0013(9) C9 0.0263(11) 0.0229(10) 0.0166(9) 0.0027(8) 0.0079(8) 0.0021(8) C10 0.0273(11) 0.0185(10) 0.0191(10) 0.0022(8) 0.0115(8) 0.0022(8) C11 0.0282(11) 0.0228(10) 0.0198(10) 0.0049(8) 0.0124(8) 0.0059(8) C12 0.0332(12) 0.0188(10) 0.0334(12) -0.0005(9) 0.0156(10) 0.0016(8) C13 0.0350(12) 0.0229(11) 0.0306(12) -0.0049(9) 0.0150(10) 0.0027(9) C14 0.0247(11) 0.0291(11) 0.0230(10) -0.0026(9) 0.0103(8) 0.0053(9) C15 0.0380(13) 0.0369(13) 0.0285(11) -0.0061(10) 0.0195(10) 0.0035(10) C16 0.0423(14) 0.0477(14) 0.0301(12) 0.0003(11) 0.0246(11) 0.0025(11) C17 0.0365(13) 0.0334(12) 0.0335(12) 0.0055(10) 0.0192(10) -0.0008(10) C18 0.0289(11) 0.0252(11) 0.0247(11) 0.0005(9) 0.0120(9) 0.0010(9) C19 0.0225(10) 0.0231(10) 0.0210(10) 0.0016(8) 0.0091(8) 0.0050(8) C20 0.0215(10) 0.0220(10) 0.0200(10) 0.0000(8) 0.0081(8) 0.0030(8) N1 0.0303(11) 0.0543(14) 0.0430(12) 0.0270(11) 0.0235(9) 0.0117(9) C21 0.0320(13) 0.0340(13) 0.0519(15) 0.0137(11) 0.0194(11) 0.0009(10) C22 0.0310(12) 0.0299(12) 0.0311(12) 0.0029(10) 0.0135(9) -0.0010(9) C23 0.0233(10) 0.0291(11) 0.0211(10) 0.0031(8) 0.0100(8) 0.0020(8) C24 0.0302(12) 0.0373(13) 0.0234(11) 0.0013(9) 0.0105(9) 0.0034(10) C25 0.0318(13) 0.0612(17) 0.0233(11) 0.0109(11) 0.0138(10) 0.0148(12) C26 0.0316(12) 0.0315(12) 0.0242(11) 0.0032(9) 0.0132(9) -0.0024(9) N2 0.0419(11) 0.0337(11) 0.0255(10) 0.0039(8) 0.0198(9) -0.0018(9) O5 0.0735(13) 0.0279(9) 0.0417(10) 0.0009(7) 0.0349(9) -0.0056(8) O6 0.0613(11) 0.0283(9) 0.0345(9) -0.0004(7) 0.0274(9) -0.0030(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O3 1.4768(14) . ? P O4 1.4831(15) . ? P O1 1.6077(15) . ? P O2 1.6225(14) . ? O1 C11 1.397(2) . ? O2 C1 1.398(2) . ? C1 C10 1.379(3) . ? C1 C2 1.400(3) . ? C2 C3 1.351(3) . ? C2 H2 0.9400 . ? C3 C4 1.416(3) . ? C3 H3 0.9400 . ? C4 C5 1.412(3) . ? C4 C9 1.422(3) . ? C5 C6 1.363(3) . ? C5 H5 0.9400 . ? C6 C7 1.405(3) . ? C6 H6 0.9400 . ? C7 C8 1.370(3) . ? C7 H7 0.9400 . ? C8 C9 1.415(3) . ? C8 H8 0.9400 . ? C9 C10 1.434(3) . ? C10 C20 1.492(3) . ? C11 C20 1.377(3) . ? C11 C12 1.397(3) . ? C12 C13 1.363(3) . ? C12 H12 0.9400 . ? C13 C14 1.412(3) . ? C13 H13 0.9400 . ? C14 C15 1.420(3) . ? C14 C19 1.421(3) . ? C15 C16 1.360(3) . ? C15 H15 0.9400 . ? C16 C17 1.402(3) . ? C16 H16 0.9400 . ? C17 C18 1.367(3) . ? C17 H17 0.9400 . ? C18 C19 1.421(3) . ? C18 H18 0.9400 . ? C19 C20 1.436(3) . ? N1 C21 1.330(3) . ? N1 C25 1.330(3) . ? N1 H1 0.90(3) . ? C21 C22 1.370(3) . ? C21 H21 0.9400 . ? C22 C23 1.386(3) . ? C22 H22 0.9400 . ? C23 C24 1.384(3) . ? C23 C26 1.514(3) . ? C24 C25 1.376(3) . ? C24 H24 0.9400 . ? C25 H25 0.9400 . ? C26 O5 1.236(3) . ? C26 N2 1.328(3) . ? N2 H2A 0.91(3) . ? N2 H2B 0.88(3) . ? O6 H6A 0.88(3) . ? O6 H6B 0.92(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 O3 P O4 120.62(9) . . ? O3 P O1 106.15(8) . . ? O4 P O1 111.84(8) . . ? O3 P O2 111.08(8) . . ? O4 P O2 104.68(8) . . ? O1 P O2 100.73(7) . . ? C11 O1 P 116.90(12) . . ? C1 O2 P 119.06(12) . . ? C10 C1 O2 119.79(17) . . ? C10 C1 C2 123.41(18) . . ? O2 C1 C2 116.78(17) . . ? C3 C2 C1 119.47(19) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 120.68(19) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 120.83(19) . . ? C5 C4 C9 119.38(19) . . ? C3 C4 C9 119.72(18) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 119.8(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C6 120.5(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 121.2(2) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C8 C9 C4 117.87(18) . . ? C8 C9 C10 122.77(18) . . ? C4 C9 C10 119.24(18) . . ? C1 C10 C9 117.32(17) . . ? C1 C10 C20 119.72(17) . . ? C9 C10 C20 122.89(17) . . ? C20 C11 C12 123.69(18) . . ? C20 C11 O1 118.67(17) . . ? C12 C11 O1 117.64(17) . . ? C13 C12 C11 119.19(19) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 120.46(19) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 120.75(19) . . ? C13 C14 C19 120.09(18) . . ? C15 C14 C19 119.13(19) . . ? C16 C15 C14 121.3(2) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 119.8(2) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 120.8(2) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 121.1(2) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C18 C19 C14 117.94(17) . . ? C18 C19 C20 122.98(18) . . ? C14 C19 C20 119.03(18) . . ? C11 C20 C19 117.46(17) . . ? C11 C20 C10 118.90(17) . . ? C19 C20 C10 123.52(17) . . ? C21 N1 C25 122.0(2) . . ? C21 N1 H1 121.2(18) . . ? C25 N1 H1 116.7(18) . . ? N1 C21 C22 119.8(2) . . ? N1 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? C21 C22 C23 120.2(2) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 118.34(19) . . ? C24 C23 C26 117.88(19) . . ? C22 C23 C26 123.74(19) . . ? C25 C24 C23 119.2(2) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? N1 C25 C24 120.5(2) . . ? N1 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? O5 C26 N2 124.1(2) . . ? O5 C26 C23 118.50(19) . . ? N2 C26 C23 117.39(19) . . ? C26 N2 H2A 123.2(16) . . ? C26 N2 H2B 119.7(17) . . ? H2A N2 H2B 117(2) . . ? H6A O6 H6B 102(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.90(3) 2.14(3) 2.917(2) 144(2) . N1 H1 O4 0.90(3) 2.39(3) 3.027(3) 128(2) 5 N2 H2A O6 0.91(3) 2.20(3) 3.105(3) 179(2) 1_545 N2 H2B O3 0.88(3) 2.19(3) 3.058(2) 168(2) 6_565 O6 H6A O3 0.88(3) 1.92(3) 2.775(2) 164(3) 6_565 O6 H6B O5 0.92(3) 1.90(3) 2.815(2) 174(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.240 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.059 # Attachment '2_INS.cif' data_thompm _database_code_depnum_ccdc_archive 'CCDC 286355' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (isonicotin-1-ium acid)(R-1,1'-binaphthalene-2,2'-diyl phosphate) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 N O6 P' _chemical_formula_weight 471.38 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.8200(11) _cell_length_b 12.3523(19) _cell_length_c 25.480(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2146.5(6) _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 light-yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9262 _exptl_absorpt_correction_T_max 0.9792 _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 17700 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0456 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.40 _reflns_number_total 4414 _reflns_number_gt 2736 _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 atom on N (isonicotinic acid) was found and refined with Ueq(H) = 1.5 Ueq(N). The protic hydrogen atom on O (isonicotinic acid) was found but had to be kept fixed during further refinement with Ueq(H) = 1.5 Ueq(O). Hydrogen atoms on C (isonicotinic acid 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^)+(0.0000P)^2^+3.4270P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_number_reflns 4414 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1214 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 P P 0.8055(3) 0.15092(9) 0.81568(6) 0.0737(6) Uani 1 1 d . . . O1 O 0.9962(6) 0.1009(3) 0.84372(17) 0.0684(12) Uani 1 1 d . . . O2 O 0.6353(5) 0.1334(2) 0.85861(12) 0.0540(9) Uani 1 1 d . . . O3 O 0.7751(7) 0.0791(2) 0.76924(14) 0.0802(14) Uani 1 1 d . . . O4 O 0.8230(9) 0.2688(2) 0.80857(17) 0.115(2) Uani 1 1 d . . . C1 C 1.0277(8) 0.1113(3) 0.8975(3) 0.0617(16) Uani 1 1 d . . . C2 C 1.1887(10) 0.1715(4) 0.9133(3) 0.099(3) Uani 1 1 d . . . H2 H 1.2672 0.2070 0.8883 0.119 Uiso 1 1 calc R . . C3 C 1.2311(10) 0.1784(5) 0.9640(4) 0.100(3) Uani 1 1 d . . . H3 H 1.3449 0.2155 0.9744 0.121 Uiso 1 1 calc R . . C4 C 1.1100(9) 0.1315(4) 1.0027(3) 0.0730(19) Uani 1 1 d . . . C5 C 1.1412(12) 0.1458(5) 1.0562(3) 0.099(3) Uani 1 1 d . . . H5 H 1.2537 0.1832 1.0673 0.119 Uiso 1 1 calc R . . C6 C 1.0145(12) 0.1076(5) 1.0927(3) 0.091(3) Uani 1 1 d . . . H6 H 1.0426 0.1179 1.1284 0.109 Uiso 1 1 calc R . . C7 C 0.8383(12) 0.0518(4) 1.0780(2) 0.084(2) Uani 1 1 d . . . H7 H 0.7487 0.0277 1.1035 0.101 Uiso 1 1 calc R . . C8 C 0.8045(10) 0.0344(3) 1.0245(2) 0.0618(16) Uani 1 1 d . . . H8 H 0.6917 -0.0034 1.0139 0.074 Uiso 1 1 calc R . . C9 C 0.9358(7) 0.0724(3) 0.9865(2) 0.0526(14) Uani 1 1 d . . . C10 C 0.9060(7) 0.0579(3) 0.9321(2) 0.0441(12) Uani 1 1 d . . . C11 C 0.6159(7) 0.0263(3) 0.87626(18) 0.0413(11) Uani 1 1 d . . . C12 C 0.4586(8) -0.0353(4) 0.8581(2) 0.0617(14) Uani 1 1 d . . . H12 H 0.3641 -0.0043 0.8358 0.074 Uiso 1 1 calc R . . C13 C 0.4436(7) -0.1401(5) 0.8728(2) 0.0663(16) Uani 1 1 d . . . H13 H 0.3338 -0.1804 0.8621 0.080 Uiso 1 1 calc R . . C14 C 0.5868(7) -0.1896(4) 0.9034(2) 0.0476(12) Uani 1 1 d . . . C15 C 0.5913(9) -0.3029(4) 0.9135(2) 0.0640(16) Uani 1 1 d . . . H15 H 0.4879 -0.3463 0.9011 0.077 Uiso 1 1 calc R . . C16 C 0.7359(10) -0.3494(4) 0.9398(2) 0.0660(17) Uani 1 1 d . . . H16 H 0.7337 -0.4245 0.9456 0.079 Uiso 1 1 calc R . . C17 C 0.8919(10) -0.2876(4) 0.9589(2) 0.0692(17) Uani 1 1 d . . . H17 H 0.9944 -0.3215 0.9773 0.083 Uiso 1 1 calc R . . C18 C 0.8963(8) -0.1773(3) 0.9510(2) 0.0553(14) Uani 1 1 d . . . H18 H 1.0013 -0.1362 0.9642 0.066 Uiso 1 1 calc R . . C19 C 0.7447(7) -0.1261(3) 0.92324(16) 0.0382(10) Uani 1 1 d . . . C20 C 0.7498(6) -0.0126(3) 0.91116(16) 0.0351(10) Uani 1 1 d . . . N N 0.7995(8) -0.1339(3) 0.77550(16) 0.0586(13) Uani 1 1 d . . . H H 0.757(9) -0.064(4) 0.770(2) 0.088 Uiso 1 1 d . . . C21 C 0.9441(9) -0.1729(4) 0.8042(2) 0.0611(15) Uani 1 1 d . . . H21 H 1.0358 -0.1250 0.8190 0.073 Uiso 1 1 calc R . . C22 C 0.9634(8) -0.2819(4) 0.8128(2) 0.0556(13) Uani 1 1 d . . . H22 H 1.0668 -0.3094 0.8332 0.067 Uiso 1 1 calc R . . C23 C 0.8278(10) -0.3491(4) 0.79085(18) 0.0572(15) Uani 1 1 d . . . C24 C 0.6740(12) -0.3078(4) 0.7622(2) 0.092(2) Uani 1 1 d . . . H24 H 0.5785 -0.3542 0.7480 0.110 Uiso 1 1 calc R . . C25 C 0.6617(12) -0.1976(5) 0.7547(2) 0.092(2) Uani 1 1 d . . . H25 H 0.5580 -0.1677 0.7352 0.111 Uiso 1 1 calc R . . C26 C 0.8445(16) -0.4695(5) 0.7988(3) 0.110(3) Uani 1 1 d . . . O5 O 0.7329(10) -0.5268(3) 0.7740(3) 0.139(3) Uani 1 1 d . . . H51 H 0.7732 -0.5925 0.7853 0.208 Uiso 1 1 d . . . O6 O 0.9631(10) -0.5067(4) 0.8289(2) 0.122(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P 0.1224(15) 0.0207(5) 0.0780(10) 0.0153(6) 0.0533(10) 0.0198(7) O1 0.074(3) 0.0272(16) 0.104(3) -0.0080(18) 0.046(2) -0.0052(18) O2 0.071(2) 0.0340(16) 0.057(2) 0.0159(15) 0.0220(18) 0.0215(16) O3 0.143(4) 0.0292(16) 0.068(2) 0.0100(16) 0.047(3) 0.020(2) O4 0.215(6) 0.0207(15) 0.109(3) 0.0189(19) 0.099(4) 0.024(3) C1 0.045(3) 0.019(2) 0.120(5) -0.021(3) 0.022(3) -0.008(2) C2 0.066(4) 0.043(3) 0.188(8) -0.055(4) 0.039(5) -0.028(3) C3 0.052(4) 0.048(3) 0.201(9) -0.048(5) 0.002(5) -0.019(3) C4 0.073(4) 0.028(3) 0.118(5) -0.034(3) -0.037(4) 0.011(3) C5 0.098(6) 0.046(4) 0.153(8) -0.038(5) -0.057(5) 0.025(4) C6 0.134(7) 0.037(3) 0.100(6) -0.032(3) -0.070(5) 0.037(4) C7 0.147(7) 0.031(3) 0.075(4) -0.002(3) -0.022(4) 0.031(4) C8 0.098(5) 0.024(2) 0.063(3) -0.002(2) -0.024(3) 0.006(3) C9 0.049(3) 0.0171(19) 0.091(4) -0.009(2) -0.017(3) 0.005(2) C10 0.037(3) 0.0168(19) 0.078(4) 0.000(2) -0.003(2) -0.0034(18) C11 0.043(3) 0.030(2) 0.051(3) 0.009(2) 0.009(2) 0.003(2) C12 0.044(3) 0.071(4) 0.070(4) -0.001(3) -0.016(3) 0.005(3) C13 0.042(3) 0.062(3) 0.095(4) -0.008(3) -0.019(3) -0.018(3) C14 0.050(3) 0.036(2) 0.056(3) -0.002(2) 0.004(2) -0.022(2) C15 0.081(4) 0.038(3) 0.073(4) -0.003(3) 0.012(3) -0.025(3) C16 0.110(5) 0.019(2) 0.068(3) 0.007(2) 0.014(4) -0.015(3) C17 0.116(5) 0.025(2) 0.067(4) 0.003(2) -0.016(3) 0.007(3) C18 0.076(4) 0.023(2) 0.068(3) -0.003(2) -0.021(3) 0.001(2) C19 0.048(3) 0.0200(19) 0.047(2) 0.0015(17) -0.004(2) -0.0084(18) C20 0.033(2) 0.0238(19) 0.049(2) 0.0053(18) 0.004(2) -0.0022(17) N 0.102(4) 0.0243(18) 0.050(2) 0.0060(18) 0.015(3) 0.017(2) C21 0.068(4) 0.031(2) 0.085(4) -0.013(3) 0.010(3) -0.007(2) C22 0.072(4) 0.033(2) 0.063(3) -0.005(3) -0.003(3) 0.007(2) C23 0.104(5) 0.025(2) 0.042(3) -0.001(2) 0.012(3) -0.002(3) C24 0.146(7) 0.045(3) 0.084(4) -0.026(3) -0.049(5) -0.014(4) C25 0.159(7) 0.061(4) 0.058(4) -0.011(3) -0.050(4) 0.005(4) C26 0.190(10) 0.032(3) 0.110(6) -0.004(4) 0.088(6) -0.007(5) O5 0.175(6) 0.037(2) 0.205(6) -0.035(3) 0.048(5) -0.034(3) O6 0.212(7) 0.046(3) 0.108(4) 0.030(3) 0.064(4) 0.044(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P O4 1.472(3) . ? P O3 1.494(4) . ? P O1 1.607(5) . ? P O2 1.610(3) . ? O1 C1 1.394(7) . ? O2 C11 1.403(5) . ? C1 C10 1.378(7) . ? C1 C2 1.385(8) . ? C2 C3 1.326(10) . ? C2 H2 0.9400 . ? C3 C4 1.412(9) . ? C3 H3 0.9400 . ? C4 C5 1.389(9) . ? C4 C9 1.454(7) . ? C5 C6 1.354(10) . ? C5 H5 0.9400 . ? C6 C7 1.434(9) . ? C6 H6 0.9400 . ? C7 C8 1.400(7) . ? C7 H7 0.9400 . ? C8 C9 1.399(7) . ? C8 H8 0.9400 . ? C9 C10 1.414(7) . ? C10 C20 1.476(6) . ? C11 C20 1.362(6) . ? C11 C12 1.394(7) . ? C12 C13 1.352(7) . ? C12 H12 0.9400 . ? C13 C14 1.391(7) . ? C13 H13 0.9400 . ? C14 C15 1.424(7) . ? C14 C19 1.425(6) . ? C15 C16 1.322(8) . ? C15 H15 0.9400 . ? C16 C17 1.397(8) . ? C16 H16 0.9400 . ? C17 C18 1.378(6) . ? C17 H17 0.9400 . ? C18 C19 1.403(6) . ? C18 H18 0.9400 . ? C19 C20 1.436(5) . ? N C21 1.319(7) . ? N C25 1.335(8) . ? N H 0.92(6) . ? C21 C22 1.370(6) . ? C21 H21 0.9400 . ? C22 C23 1.363(7) . ? C22 H22 0.9400 . ? C23 C24 1.376(8) . ? C23 C26 1.505(7) . ? C24 C25 1.377(8) . ? C24 H24 0.9400 . ? C25 H25 0.9400 . ? C26 O6 1.205(12) . ? C26 O5 1.217(11) . ? O5 H51 0.9041 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 P O3 120.1(2) . . ? O4 P O1 111.7(3) . . ? O3 P O1 103.7(2) . . ? O4 P O2 106.0(2) . . ? O3 P O2 111.0(2) . . ? O1 P O2 103.27(19) . . ? C1 O1 P 121.8(3) . . ? C11 O2 P 114.4(3) . . ? C10 C1 C2 123.3(7) . . ? C10 C1 O1 119.4(5) . . ? C2 C1 O1 117.2(6) . . ? C3 C2 C1 119.3(7) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 121.8(6) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 122.9(7) . . ? C5 C4 C9 117.9(7) . . ? C3 C4 C9 119.0(6) . . ? C6 C5 C4 122.0(7) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C7 121.6(7) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 117.7(7) . . ? C8 C7 H7 121.2 . . ? C6 C7 H7 121.2 . . ? C9 C8 C7 121.1(6) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 123.0(4) . . ? C8 C9 C4 119.7(6) . . ? C10 C9 C4 117.3(5) . . ? C1 C10 C9 118.7(5) . . ? C1 C10 C20 119.1(5) . . ? C9 C10 C20 122.2(4) . . ? C20 C11 C12 122.7(4) . . ? C20 C11 O2 118.6(4) . . ? C12 C11 O2 118.7(4) . . ? C13 C12 C11 119.2(5) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 121.6(5) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C13 C14 C15 123.3(5) . . ? C13 C14 C19 119.2(4) . . ? C15 C14 C19 117.4(5) . . ? C16 C15 C14 122.3(5) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C15 C16 C17 120.5(4) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C18 C17 C16 120.4(6) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 120.2(5) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C14 119.2(4) . . ? C18 C19 C20 122.0(4) . . ? C14 C19 C20 118.7(4) . . ? C11 C20 C19 117.9(4) . . ? C11 C20 C10 120.8(4) . . ? C19 C20 C10 121.1(4) . . ? C21 N C25 122.1(4) . . ? C21 N H 132(4) . . ? C25 N H 106(4) . . ? N C21 C22 121.3(5) . . ? N C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 117.9(5) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? C22 C23 C24 120.6(4) . . ? C22 C23 C26 119.7(7) . . ? C24 C23 C26 119.7(7) . . ? C23 C24 C25 119.2(6) . . ? C23 C24 H24 120.4 . . ? C25 C24 H24 120.4 . . ? N C25 C24 118.9(6) . . ? N C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? O6 C26 O5 121.9(6) . . ? O6 C26 C23 120.9(9) . . ? O5 C26 C23 117.2(10) . . ? C26 O5 H51 99.6 . . ? 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 N H O3 0.92(6) 1.77(6) 2.640(5) 156(6) . O5 H51 O4 0.90 1.84 2.744(6) 172.9 1_545 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.494 _refine_diff_density_min -0.756 _refine_diff_density_rms 0.064 # Attachment '3_Guanidin.cif' data_thomqm _database_code_depnum_ccdc_archive 'CCDC 286356' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (guanidinium)-(rac-1,1'-binaphthalene-2,2'-diylphosphate)- .dihydrate.semi-methanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H48 N6 O13 P2' _chemical_formula_weight 918.81 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0813(15) _cell_length_b 11.2429(17) _cell_length_c 21.107(3) _cell_angle_alpha 93.363(3) _cell_angle_beta 98.274(3) _cell_angle_gamma 112.770(3) _cell_volume 2165.7(6) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 0.174 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9330 _exptl_absorpt_correction_T_max 0.9850 _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 19709 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.1103 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 0.98 _diffrn_reflns_theta_max 28.81 _reflns_number_total 10115 _reflns_number_gt 4815 _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 hydrogen atoms on N (guanidinium) and O (water, methanol) were all found and refined with Ueq(H) = 1.5 Ueq(N/O). Hydrogen atoms on C (binaphthyl) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C), the ones on C (methanol) as an idealized CH3 group (AFIX 133) and Ueq(H) = 1.5 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10115 _refine_ls_number_parameters 640 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1333 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.0659 _refine_ls_wR_factor_gt 0.0553 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 P1 P 0.10144(8) 0.38044(7) 0.34076(3) 0.03233(19) Uani 1 1 d . . . O1 O 0.18901(16) 0.46196(15) 0.28896(7) 0.0300(4) Uani 1 1 d . . . O2 O -0.06143(16) 0.30320(15) 0.29961(8) 0.0321(4) Uani 1 1 d . . . O3 O 0.16804(17) 0.28713(15) 0.35897(7) 0.0344(5) Uani 1 1 d . . . O4 O 0.08661(18) 0.46672(16) 0.39300(8) 0.0395(5) Uani 1 1 d . . . C1 C 0.1204(3) 0.5311(2) 0.25322(11) 0.0259(6) Uani 1 1 d . . . C2 C 0.1752(3) 0.6650(2) 0.27089(11) 0.0320(7) Uani 1 1 d . . . H2 H 0.2559 0.7063 0.3045 0.038 Uiso 1 1 calc R . . C3 C 0.1097(3) 0.7348(2) 0.23849(12) 0.0321(7) Uani 1 1 d . . . H3 H 0.1461 0.8253 0.2498 0.038 Uiso 1 1 calc R . . C4 C -0.0122(3) 0.6736(2) 0.18804(12) 0.0284(6) Uani 1 1 d . . . C5 C -0.0845(3) 0.7449(3) 0.15627(13) 0.0387(7) Uani 1 1 d . . . H5 H -0.0470 0.8356 0.1667 0.046 Uiso 1 1 calc R . . C6 C -0.2080(3) 0.6838(3) 0.11052(13) 0.0409(7) Uani 1 1 d . . . H6 H -0.2547 0.7324 0.0895 0.049 Uiso 1 1 calc R . . C7 C -0.2647(3) 0.5484(2) 0.09508(12) 0.0335(7) Uani 1 1 d . . . H7 H -0.3511 0.5064 0.0644 0.040 Uiso 1 1 calc R . . C8 C -0.1963(3) 0.4771(2) 0.12385(11) 0.0293(6) Uani 1 1 d . . . H8 H -0.2359 0.3865 0.1124 0.035 Uiso 1 1 calc R . . C9 C -0.0670(3) 0.5364(2) 0.17060(11) 0.0267(6) Uani 1 1 d . . . C10 C 0.0071(3) 0.4654(2) 0.20355(11) 0.0234(6) Uani 1 1 d . . . C11 C -0.0769(3) 0.2451(2) 0.23727(12) 0.0298(7) Uani 1 1 d . . . C12 C -0.1308(3) 0.1093(2) 0.22710(14) 0.0376(7) Uani 1 1 d . . . H12 H -0.1535 0.0603 0.2616 0.045 Uiso 1 1 calc R . . C13 C -0.1500(3) 0.0494(3) 0.16673(14) 0.0424(8) Uani 1 1 d . . . H13 H -0.1910 -0.0420 0.1592 0.051 Uiso 1 1 calc R . . C14 C -0.1095(3) 0.1218(3) 0.11477(13) 0.0347(7) Uani 1 1 d . . . C15 C -0.1192(3) 0.0609(3) 0.05257(14) 0.0470(8) Uani 1 1 d . . . H15 H -0.1592 -0.0304 0.0445 0.056 Uiso 1 1 calc R . . C16 C -0.0718(3) 0.1320(3) 0.00442(14) 0.0513(9) Uani 1 1 d . . . H16 H -0.0788 0.0897 -0.0365 0.062 Uiso 1 1 calc R . . C17 C -0.0125(3) 0.2681(3) 0.01536(13) 0.0433(8) Uani 1 1 d . . . H17 H 0.0220 0.3170 -0.0179 0.052 Uiso 1 1 calc R . . C18 C -0.0048(3) 0.3302(3) 0.07467(12) 0.0353(7) Uani 1 1 d . . . H18 H 0.0338 0.4215 0.0813 0.042 Uiso 1 1 calc R . . C19 C -0.0538(2) 0.2594(2) 0.12591(12) 0.0279(6) Uani 1 1 d . . . C20 C -0.0440(2) 0.3218(2) 0.18860(12) 0.0260(6) Uani 1 1 d . . . P2 P 0.47316(8) 0.08085(7) 0.36284(3) 0.03130(19) Uani 1 1 d . . . O5 O 0.33173(16) 0.04061(15) 0.30633(7) 0.0284(4) Uani 1 1 d . . . O6 O 0.59195(16) 0.06378(15) 0.32390(7) 0.0287(4) Uani 1 1 d . . . O7 O 0.53313(18) 0.22040(16) 0.38810(7) 0.0372(5) Uani 1 1 d . . . O8 O 0.42846(18) -0.01834(17) 0.40779(7) 0.0386(5) Uani 1 1 d . . . C21 C 0.3471(3) 0.0899(2) 0.24697(11) 0.0256(6) Uani 1 1 d . . . C22 C 0.2853(3) 0.1795(2) 0.23348(12) 0.0317(7) Uani 1 1 d . . . H22 H 0.2409 0.2072 0.2641 0.038 Uiso 1 1 calc R . . C23 C 0.2901(3) 0.2261(2) 0.17547(12) 0.0333(7) Uani 1 1 d . . . H23 H 0.2436 0.2823 0.1649 0.040 Uiso 1 1 calc R . . C24 C 0.3647(3) 0.1905(2) 0.13104(11) 0.0267(6) Uani 1 1 d . . . C25 C 0.3768(3) 0.2430(2) 0.07140(12) 0.0329(7) Uani 1 1 d . . . H25 H 0.3269 0.2959 0.0596 0.040 Uiso 1 1 calc R . . C26 C 0.4596(3) 0.2179(2) 0.03114(12) 0.0350(7) Uani 1 1 d . . . H26 H 0.4663 0.2530 -0.0082 0.042 Uiso 1 1 calc R . . C27 C 0.5347(3) 0.1394(2) 0.04875(11) 0.0301(6) Uani 1 1 d . . . H27 H 0.5958 0.1260 0.0220 0.036 Uiso 1 1 calc R . . C28 C 0.5206(2) 0.0821(2) 0.10418(11) 0.0264(6) Uani 1 1 d . . . H28 H 0.5697 0.0277 0.1142 0.032 Uiso 1 1 calc R . . C29 C 0.4332(2) 0.1034(2) 0.14658(11) 0.0243(6) Uani 1 1 d . . . C30 C 0.4145(2) 0.0438(2) 0.20504(11) 0.0231(6) Uani 1 1 d . . . C31 C 0.5494(3) -0.0489(2) 0.28020(11) 0.0254(6) Uani 1 1 d . . . C32 C 0.6013(3) -0.1423(2) 0.29972(12) 0.0328(7) Uani 1 1 d . . . H32 H 0.6569 -0.1302 0.3412 0.039 Uiso 1 1 calc R . . C33 C 0.5708(3) -0.2502(2) 0.25834(12) 0.0350(7) Uani 1 1 d . . . H33 H 0.6090 -0.3113 0.2705 0.042 Uiso 1 1 calc R . . C34 C 0.4820(3) -0.2714(2) 0.19715(12) 0.0291(6) Uani 1 1 d . . . C35 C 0.4435(3) -0.3870(2) 0.15504(12) 0.0366(7) Uani 1 1 d . . . H35 H 0.4812 -0.4484 0.1672 0.044 Uiso 1 1 calc R . . C36 C 0.3527(3) -0.4104(3) 0.09715(13) 0.0385(7) Uani 1 1 d . . . H36 H 0.3300 -0.4866 0.0692 0.046 Uiso 1 1 calc R . . C37 C 0.2934(3) -0.3210(2) 0.07935(12) 0.0332(7) Uani 1 1 d . . . H37 H 0.2281 -0.3390 0.0400 0.040 Uiso 1 1 calc R . . C38 C 0.3292(3) -0.2075(2) 0.11852(11) 0.0273(6) Uani 1 1 d . . . H38 H 0.2884 -0.1485 0.1055 0.033 Uiso 1 1 calc R . . C39 C 0.4267(3) -0.1774(2) 0.17821(11) 0.0242(6) Uani 1 1 d . . . C40 C 0.4669(2) -0.0597(2) 0.22093(11) 0.0231(6) Uani 1 1 d . . . N1 N 0.2620(3) 0.4338(2) 0.51733(11) 0.0407(7) Uani 1 1 d . . . H1A H 0.247(3) 0.477(2) 0.5500(12) 0.061 Uiso 1 1 d . . . H1B H 0.219(3) 0.434(3) 0.4747(12) 0.061 Uiso 1 1 d . . . N2 N 0.3781(3) 0.3190(2) 0.47292(11) 0.0394(7) Uani 1 1 d . . . H2A H 0.320(3) 0.308(2) 0.4317(11) 0.059 Uiso 1 1 d . . . H2B H 0.446(3) 0.288(2) 0.4746(12) 0.059 Uiso 1 1 d . . . N3 N 0.4361(3) 0.3883(2) 0.58168(12) 0.0406(7) Uani 1 1 d . . . H3A H 0.430(3) 0.441(2) 0.6156(12) 0.061 Uiso 1 1 d . . . H3B H 0.504(3) 0.356(3) 0.5856(13) 0.061 Uiso 1 1 d . . . C41 C 0.3610(3) 0.3809(2) 0.52365(13) 0.0309(7) Uani 1 1 d . . . N4 N -0.1139(3) -0.1273(2) 0.43511(12) 0.0401(7) Uani 1 1 d . . . H4A H -0.181(3) -0.117(3) 0.4550(12) 0.060 Uiso 1 1 d . . . H4B H -0.106(3) -0.204(2) 0.4300(12) 0.060 Uiso 1 1 d . . . N5 N -0.0510(3) 0.0791(3) 0.40866(12) 0.0492(8) Uani 1 1 d . . . H5A H -0.122(3) 0.090(3) 0.4293(13) 0.074 Uiso 1 1 d . . . H5B H 0.010(3) 0.151(3) 0.3913(12) 0.074 Uiso 1 1 d . . . N6 N 0.0733(3) -0.0430(3) 0.37954(13) 0.0563(8) Uani 1 1 d . . . H6A H 0.124(3) 0.026(3) 0.3604(14) 0.084 Uiso 1 1 d . . . H6B H 0.089(3) -0.119(3) 0.3822(14) 0.084 Uiso 1 1 d . . . C42 C -0.0301(3) -0.0286(3) 0.40816(12) 0.0368(7) Uani 1 1 d . . . O9 O 0.0433(2) 0.7020(2) 0.42218(10) 0.0555(7) Uani 1 1 d . . . H9A H 0.083(3) 0.701(3) 0.4635(13) 0.083 Uiso 1 1 d . . . H9B H 0.043(3) 0.634(3) 0.4026(14) 0.083 Uiso 1 1 d . . . O10 O 0.3706(2) 0.7266(2) 0.43545(12) 0.0542(7) Uani 1 1 d . . . H10A H 0.387(3) 0.811(3) 0.4308(14) 0.081 Uiso 1 1 d . . . H10B H 0.288(3) 0.689(3) 0.4300(16) 0.081 Uiso 1 1 d . . . O11 O 0.8453(2) 0.3224(3) 0.45382(11) 0.0691(8) Uani 1 1 d . . . H11A H 0.903(3) 0.375(3) 0.4297(15) 0.104 Uiso 1 1 d . . . H11B H 0.765(3) 0.290(3) 0.4320(16) 0.104 Uiso 1 1 d . . . O12 O 0.3042(2) 0.0131(2) 0.52034(9) 0.0489(6) Uani 1 1 d . . . H12A H 0.322(3) 0.010(3) 0.4860(12) 0.073 Uiso 1 1 d . . . H12B H 0.387(3) 0.027(3) 0.5428(13) 0.073 Uiso 1 1 d . . . O13 O 0.6384(3) 0.44649(19) 0.33857(11) 0.0682(7) Uani 1 1 d . . . H13A H 0.590(3) 0.373(3) 0.3504(15) 0.102 Uiso 1 1 d . . . C43 C 0.6910(3) 0.4434(3) 0.28052(13) 0.0652(10) Uani 1 1 d . . . H43A H 0.7577 0.5302 0.2756 0.098 Uiso 1 1 calc R . . H43B H 0.6095 0.4120 0.2445 0.098 Uiso 1 1 calc R . . H43C H 0.7419 0.3857 0.2814 0.098 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 P1 0.0336(4) 0.0353(5) 0.0317(4) 0.0063(4) 0.0085(4) 0.0164(4) O1 0.0271(10) 0.0329(11) 0.0307(10) 0.0098(9) 0.0069(9) 0.0112(9) O2 0.0275(11) 0.0354(11) 0.0341(11) 0.0074(9) 0.0084(9) 0.0118(9) O3 0.0386(11) 0.0386(12) 0.0354(11) 0.0099(9) 0.0064(9) 0.0248(10) O4 0.0502(12) 0.0411(12) 0.0353(11) 0.0013(9) 0.0130(10) 0.0258(10) C1 0.0259(15) 0.0276(16) 0.0273(15) 0.0097(13) 0.0101(13) 0.0111(13) C2 0.0266(16) 0.0295(17) 0.0300(16) -0.0017(13) 0.0051(13) 0.0013(14) C3 0.0348(17) 0.0219(16) 0.0362(17) 0.0028(13) 0.0125(14) 0.0058(14) C4 0.0302(16) 0.0265(16) 0.0304(16) 0.0047(13) 0.0099(13) 0.0118(14) C5 0.0458(19) 0.0264(17) 0.0489(19) 0.0088(15) 0.0141(16) 0.0174(15) C6 0.049(2) 0.0375(19) 0.0449(19) 0.0106(15) 0.0069(16) 0.0265(16) C7 0.0326(16) 0.0325(17) 0.0357(17) 0.0021(14) 0.0013(13) 0.0154(15) C8 0.0330(17) 0.0247(16) 0.0307(16) 0.0014(13) 0.0067(14) 0.0120(14) C9 0.0294(16) 0.0253(16) 0.0277(15) 0.0067(13) 0.0115(13) 0.0110(13) C10 0.0243(15) 0.0220(15) 0.0243(15) 0.0040(12) 0.0077(12) 0.0084(13) C11 0.0203(15) 0.0299(17) 0.0381(17) 0.0037(14) 0.0036(13) 0.0097(13) C12 0.0312(17) 0.0257(17) 0.056(2) 0.0109(15) 0.0058(15) 0.0108(14) C13 0.0317(17) 0.0224(17) 0.072(2) 0.0042(17) -0.0031(17) 0.0146(14) C14 0.0237(16) 0.0298(17) 0.0500(19) -0.0081(15) -0.0048(14) 0.0160(14) C15 0.0401(19) 0.040(2) 0.061(2) -0.0179(17) -0.0096(17) 0.0252(16) C16 0.055(2) 0.065(2) 0.040(2) -0.0224(18) -0.0081(17) 0.041(2) C17 0.0415(18) 0.060(2) 0.0367(18) -0.0017(16) 0.0036(15) 0.0312(17) C18 0.0312(16) 0.0396(18) 0.0389(17) -0.0018(15) 0.0051(14) 0.0195(15) C19 0.0221(15) 0.0261(16) 0.0365(17) -0.0002(13) 0.0010(13) 0.0128(13) C20 0.0216(15) 0.0227(15) 0.0348(16) 0.0009(13) 0.0031(13) 0.0112(13) P2 0.0338(4) 0.0376(5) 0.0251(4) 0.0016(4) 0.0073(4) 0.0167(4) O5 0.0270(10) 0.0376(11) 0.0226(10) 0.0038(8) 0.0077(8) 0.0141(9) O6 0.0267(10) 0.0352(11) 0.0255(10) -0.0009(8) 0.0052(8) 0.0144(9) O7 0.0441(12) 0.0329(11) 0.0334(11) -0.0059(9) 0.0040(9) 0.0167(10) O8 0.0462(12) 0.0508(13) 0.0271(10) 0.0163(9) 0.0135(9) 0.0243(10) C21 0.0253(15) 0.0265(16) 0.0240(15) 0.0055(12) 0.0031(12) 0.0094(13) C22 0.0322(16) 0.0360(17) 0.0347(17) 0.0007(14) 0.0113(14) 0.0207(14) C23 0.0336(16) 0.0319(17) 0.0415(18) 0.0053(14) 0.0077(14) 0.0203(14) C24 0.0294(15) 0.0248(15) 0.0282(15) 0.0059(12) 0.0031(13) 0.0137(13) C25 0.0369(17) 0.0289(16) 0.0355(16) 0.0091(13) 0.0020(14) 0.0166(14) C26 0.0410(18) 0.0344(17) 0.0273(16) 0.0075(13) 0.0029(14) 0.0131(15) C27 0.0316(16) 0.0290(16) 0.0291(16) 0.0026(13) 0.0075(13) 0.0109(14) C28 0.0298(15) 0.0250(15) 0.0262(15) 0.0055(12) 0.0061(13) 0.0123(13) C29 0.0233(14) 0.0243(15) 0.0265(15) 0.0010(12) 0.0047(12) 0.0110(13) C30 0.0229(14) 0.0250(15) 0.0233(14) 0.0033(12) 0.0039(12) 0.0117(13) C31 0.0265(15) 0.0281(16) 0.0267(15) 0.0024(13) 0.0095(13) 0.0148(13) C32 0.0328(16) 0.0417(18) 0.0299(16) 0.0084(14) 0.0020(13) 0.0222(15) C33 0.0423(18) 0.0361(18) 0.0382(17) 0.0107(14) 0.0085(15) 0.0269(15) C34 0.0334(16) 0.0290(16) 0.0315(16) 0.0063(13) 0.0127(13) 0.0169(14) C35 0.0420(18) 0.0304(17) 0.0458(19) 0.0062(14) 0.0135(15) 0.0214(15) C36 0.0442(19) 0.0288(17) 0.0435(19) -0.0034(14) 0.0108(16) 0.0157(15) C37 0.0368(17) 0.0323(17) 0.0298(16) 0.0018(13) 0.0059(13) 0.0135(15) C38 0.0304(16) 0.0263(16) 0.0297(15) 0.0062(12) 0.0093(13) 0.0143(13) C39 0.0235(14) 0.0253(15) 0.0264(15) 0.0050(12) 0.0110(12) 0.0099(13) C40 0.0247(14) 0.0240(15) 0.0253(15) 0.0059(12) 0.0105(12) 0.0125(13) N1 0.0405(16) 0.0490(17) 0.0415(16) 0.0017(14) 0.0106(14) 0.0269(14) N2 0.0451(18) 0.0463(16) 0.0375(15) 0.0022(13) 0.0110(13) 0.0290(14) N3 0.0486(17) 0.0430(17) 0.0333(15) 0.0032(12) 0.0045(14) 0.0231(14) C41 0.0309(17) 0.0252(16) 0.0371(18) 0.0078(14) 0.0141(15) 0.0085(14) N4 0.0388(16) 0.0385(16) 0.0473(16) 0.0150(14) 0.0157(12) 0.0161(14) N5 0.055(2) 0.0376(17) 0.0545(18) 0.0179(14) 0.0107(14) 0.0167(15) N6 0.0429(17) 0.077(2) 0.0542(18) 0.0172(17) 0.0211(14) 0.0235(18) C42 0.0283(17) 0.047(2) 0.0283(16) 0.0065(15) 0.0000(14) 0.0091(16) O9 0.0649(16) 0.0545(16) 0.0566(15) 0.0044(13) 0.0192(13) 0.0317(13) O10 0.0383(13) 0.0559(16) 0.0706(15) 0.0097(14) 0.0068(13) 0.0222(14) O11 0.0493(16) 0.093(2) 0.0477(15) 0.0136(13) 0.0098(12) 0.0083(15) O12 0.0482(14) 0.0721(15) 0.0378(14) 0.0132(13) 0.0131(12) 0.0335(13) O13 0.0989(19) 0.0483(16) 0.0631(15) 0.0061(13) 0.0454(14) 0.0248(14) C43 0.086(3) 0.082(3) 0.059(2) 0.022(2) 0.038(2) 0.057(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 P1 O4 1.4876(16) . ? P1 O3 1.4891(16) . ? P1 O1 1.6075(16) . ? P1 O2 1.6131(16) . ? O1 C1 1.409(3) . ? O2 C11 1.394(3) . ? C1 C10 1.364(3) . ? C1 C2 1.394(3) . ? C2 C3 1.362(3) . ? C2 H2 0.9400 . ? C3 C4 1.414(3) . ? C3 H3 0.9400 . ? C4 C5 1.413(3) . ? C4 C9 1.427(3) . ? C5 C6 1.367(3) . ? C5 H5 0.9400 . ? C6 C7 1.402(3) . ? C6 H6 0.9400 . ? C7 C8 1.361(3) . ? C7 H7 0.9400 . ? C8 C9 1.413(3) . ? C8 H8 0.9400 . ? C9 C10 1.434(3) . ? C10 C20 1.490(3) . ? C11 C20 1.375(3) . ? C11 C12 1.399(3) . ? C12 C13 1.357(3) . ? C12 H12 0.9400 . ? C13 C14 1.418(3) . ? C13 H13 0.9400 . ? C14 C15 1.417(3) . ? C14 C19 1.418(3) . ? C15 C16 1.356(3) . ? C15 H15 0.9400 . ? C16 C17 1.401(4) . ? C16 H16 0.9400 . ? C17 C18 1.374(3) . ? C17 H17 0.9400 . ? C18 C19 1.413(3) . ? C18 H18 0.9400 . ? C19 C20 1.433(3) . ? P2 O7 1.4785(17) . ? P2 O8 1.4848(16) . ? P2 O6 1.6092(16) . ? P2 O5 1.6150(16) . ? O5 C21 1.404(2) . ? O6 C31 1.403(3) . ? C21 C30 1.380(3) . ? C21 C22 1.397(3) . ? C22 C23 1.360(3) . ? C22 H22 0.9400 . ? C23 C24 1.413(3) . ? C23 H23 0.9400 . ? C24 C25 1.423(3) . ? C24 C29 1.428(3) . ? C25 C26 1.362(3) . ? C25 H25 0.9400 . ? C26 C27 1.401(3) . ? C26 H26 0.9400 . ? C27 C28 1.367(3) . ? C27 H27 0.9400 . ? C28 C29 1.414(3) . ? C28 H28 0.9400 . ? C29 C30 1.440(3) . ? C30 C40 1.489(3) . ? C31 C40 1.370(3) . ? C31 C32 1.400(3) . ? C32 C33 1.356(3) . ? C32 H32 0.9400 . ? C33 C34 1.411(3) . ? C33 H33 0.9400 . ? C34 C35 1.416(3) . ? C34 C39 1.425(3) . ? C35 C36 1.362(3) . ? C35 H35 0.9400 . ? C36 C37 1.399(3) . ? C36 H36 0.9400 . ? C37 C38 1.370(3) . ? C37 H37 0.9400 . ? C38 C39 1.415(3) . ? C38 H38 0.9400 . ? C39 C40 1.437(3) . ? N1 C41 1.341(3) . ? N1 H1A 0.88(2) . ? N1 H1B 0.94(2) . ? N2 C41 1.311(3) . ? N2 H2A 0.95(2) . ? N2 H2B 0.88(2) . ? N3 C41 1.324(3) . ? N3 H3A 0.93(2) . ? N3 H3B 0.89(2) . ? N4 C42 1.325(3) . ? N4 H4A 0.88(2) . ? N4 H4B 0.90(2) . ? N5 C42 1.307(3) . ? N5 H5A 0.93(2) . ? N5 H5B 0.93(3) . ? N6 C42 1.333(3) . ? N6 H6A 0.90(3) . ? N6 H6B 0.93(3) . ? O9 H9A 0.91(3) . ? O9 H9B 0.84(3) . ? O10 H10A 0.91(3) . ? O10 H10B 0.76(3) . ? O11 H11A 0.89(3) . ? O11 H11B 0.80(3) . ? O12 H12A 0.77(2) . ? O12 H12B 0.85(3) . ? O13 C43 1.407(3) . ? O13 H13A 0.85(3) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C43 H43C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 P1 O3 118.57(10) . . ? O4 P1 O1 111.79(10) . . ? O3 P1 O1 107.00(9) . . ? O4 P1 O2 105.49(10) . . ? O3 P1 O2 110.10(10) . . ? O1 P1 O2 102.78(9) . . ? C1 O1 P1 115.74(14) . . ? C11 O2 P1 118.35(15) . . ? C10 C1 C2 123.8(2) . . ? C10 C1 O1 119.3(2) . . ? C2 C1 O1 117.0(2) . . ? C3 C2 C1 118.7(2) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 121.3(2) . . ? C5 C4 C9 119.3(2) . . ? C3 C4 C9 119.4(2) . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 120.9(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 121.3(2) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C4 117.8(2) . . ? C8 C9 C10 123.5(2) . . ? C4 C9 C10 118.6(2) . . ? C1 C10 C9 118.2(2) . . ? C1 C10 C20 119.7(2) . . ? C9 C10 C20 121.9(2) . . ? C20 C11 O2 119.3(2) . . ? C20 C11 C12 123.1(3) . . ? O2 C11 C12 117.5(2) . . ? C13 C12 C11 119.1(3) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 121.3(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 121.9(3) . . ? C15 C14 C19 119.1(3) . . ? C13 C14 C19 118.9(3) . . ? C16 C15 C14 121.2(3) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C17 120.3(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 121.3(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C14 118.1(2) . . ? C18 C19 C20 122.4(2) . . ? C14 C19 C20 119.5(2) . . ? C11 C20 C19 117.8(2) . . ? C11 C20 C10 119.3(2) . . ? C19 C20 C10 122.9(2) . . ? O7 P2 O8 119.53(10) . . ? O7 P2 O6 105.51(10) . . ? O8 P2 O6 111.65(10) . . ? O7 P2 O5 112.12(10) . . ? O8 P2 O5 104.84(9) . . ? O6 P2 O5 101.88(8) . . ? C21 O5 P2 119.92(14) . . ? C31 O6 P2 118.58(14) . . ? C30 C21 C22 124.4(2) . . ? C30 C21 O5 119.2(2) . . ? C22 C21 O5 116.3(2) . . ? C23 C22 C21 119.2(2) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 120.3(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 121.1(2) . . ? C23 C24 C29 119.9(2) . . ? C25 C24 C29 118.9(2) . . ? C26 C25 C24 121.2(2) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 C27 119.6(2) . . ? C25 C26 H26 120.2 . . ? C27 C26 H26 120.2 . . ? C28 C27 C26 121.2(2) . . ? C28 C27 H27 119.4 . . ? C26 C27 H27 119.4 . . ? C27 C28 C29 121.0(2) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C28 C29 C24 118.0(2) . . ? C28 C29 C30 122.6(2) . . ? C24 C29 C30 119.4(2) . . ? C21 C30 C29 116.2(2) . . ? C21 C30 C40 121.1(2) . . ? C29 C30 C40 122.7(2) . . ? C40 C31 C32 123.8(2) . . ? C40 C31 O6 119.6(2) . . ? C32 C31 O6 116.5(2) . . ? C33 C32 C31 119.4(2) . . ? C33 C32 H32 120.3 . . ? C31 C32 H32 120.3 . . ? C32 C33 C34 120.4(2) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C33 C34 C35 120.7(2) . . ? C33 C34 C39 119.8(2) . . ? C35 C34 C39 119.5(2) . . ? C36 C35 C34 120.9(3) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C35 C36 C37 119.9(3) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C38 C37 C36 120.8(2) . . ? C38 C37 H37 119.6 . . ? C36 C37 H37 119.6 . . ? C37 C38 C39 121.2(2) . . ? C37 C38 H38 119.4 . . ? C39 C38 H38 119.4 . . ? C38 C39 C34 117.6(2) . . ? C38 C39 C40 123.1(2) . . ? C34 C39 C40 119.3(2) . . ? C31 C40 C39 117.1(2) . . ? C31 C40 C30 119.8(2) . . ? C39 C40 C30 122.9(2) . . ? C41 N1 H1A 122.8(18) . . ? C41 N1 H1B 115.7(16) . . ? H1A N1 H1B 121(2) . . ? C41 N2 H2A 121.6(15) . . ? C41 N2 H2B 122.3(17) . . ? H2A N2 H2B 116(2) . . ? C41 N3 H3A 118.9(17) . . ? C41 N3 H3B 118.9(18) . . ? H3A N3 H3B 121(2) . . ? N2 C41 N3 121.2(3) . . ? N2 C41 N1 119.7(3) . . ? N3 C41 N1 119.1(3) . . ? C42 N4 H4A 118.5(18) . . ? C42 N4 H4B 119.3(18) . . ? H4A N4 H4B 122(3) . . ? C42 N5 H5A 121.3(18) . . ? C42 N5 H5B 121.3(18) . . ? H5A N5 H5B 117(2) . . ? C42 N6 H6A 114(2) . . ? C42 N6 H6B 119(2) . . ? H6A N6 H6B 127(3) . . ? N5 C42 N4 120.4(3) . . ? N5 C42 N6 121.1(3) . . ? N4 C42 N6 118.5(3) . . ? H9A O9 H9B 103(3) . . ? H10A O10 H10B 107(3) . . ? H11A O11 H11B 106(3) . . ? H12A O12 H12B 100(3) . . ? C43 O13 H13A 117(2) . . ? O13 C43 H43A 109.5 . . ? O13 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? O13 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? 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 O13 0.88(2) 2.41(2) 3.109(3) 136(2) 2_666 N1 H1B O4 0.94(2) 2.16(2) 3.072(3) 162(2) . N2 H2A O3 0.95(2) 1.94(2) 2.871(3) 167(2) . N2 H2B O7 0.88(2) 2.34(2) 2.965(3) 128(2) . N2 H2B O10 0.88(2) 2.51(3) 3.184(3) 134(2) 2_666 N3 H3A O13 0.93(2) 1.93(3) 2.814(3) 159(2) 2_666 N3 H3B O10 0.89(2) 1.91(3) 2.775(3) 161(3) 2_666 N4 H4A O12 0.88(2) 2.11(3) 2.915(3) 152(2) 2_556 N4 H4B O9 0.90(2) 2.16(3) 2.947(3) 145(2) 1_545 N5 H5A O12 0.93(2) 2.21(3) 3.012(3) 143(2) 2_556 N5 H5B O3 0.93(3) 1.98(3) 2.899(3) 168(2) . N6 H6A O5 0.90(3) 2.49(3) 3.081(3) 124(2) . N6 H6B O9 0.93(3) 2.14(3) 2.972(3) 149(3) 1_545 O9 H9A O11 0.91(3) 1.86(3) 2.768(3) 173(3) 2_666 O9 H9B O4 0.84(3) 2.10(3) 2.889(3) 156(3) . O10 H10A O8 0.91(3) 1.91(3) 2.811(3) 171(3) 1_565 O10 H10B O4 0.76(3) 2.52(3) 3.165(3) 143(3) . O10 H10B O9 0.76(3) 2.51(3) 3.171(3) 146(3) . O11 H11A O4 0.89(3) 2.03(3) 2.879(3) 158(3) 1_655 O11 H11B O7 0.80(3) 2.19(3) 2.984(3) 168(3) . O12 H12A O8 0.77(2) 2.17(3) 2.905(2) 160(3) . O12 H12B O8 0.85(3) 2.04(3) 2.874(3) 167(3) 2_656 O13 H13A O7 0.85(3) 1.86(3) 2.688(3) 164(3) . _diffrn_measured_fraction_theta_max 0.894 _diffrn_reflns_theta_full 28.81 _diffrn_measured_fraction_theta_full 0.894 _refine_diff_density_max 0.361 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.061 # Attachment '4_Cu-NH3.cif' data_thomim _database_code_depnum_ccdc_archive 'CCDC 286357' _audit_creation_method SHELXL-97 _chemical_name_systematic ; trans-(tetraammin-di(methanol~0.75/aqua~0.25)-copper(II))-bis(rac-1,1'- binaphthalene-2,2'-diylphosphate).dihydrate.monomethanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43.50 H54.50 Cu N4 O14 P2' _chemical_formula_weight 982.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 20.867(2) _cell_length_b 9.1006(11) _cell_length_c 12.2266(14) _cell_angle_alpha 90.00 _cell_angle_beta 97.654(2) _cell_angle_gamma 90.00 _cell_volume 2301.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'pale plue' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1029 _exptl_absorpt_coefficient_mu 0.614 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8101 _exptl_absorpt_correction_T_max 0.9842 _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 16523 _diffrn_reflns_av_R_equivalents 0.0877 _diffrn_reflns_av_sigmaI/netI 0.0796 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 25.10 _reflns_number_total 4094 _reflns_number_gt 2342 _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. One of the hydrogen atoms on the water of crystallization was found and refined with Ueq(H) = 1.5 Ueq(O). The other hydrogen of the water molecule was found but had to be fixed upon further refinement. The hydrogen atoms of the ammin ligands were calculated as an idealized NH3 group with tetrahedral angles in a rotating group refinement (AFIX 137) with Ueq(H) = 1.5 Ueq(N). The methanolic O-H were placed at calculated positions as an idealized OH-group with C-O-H angle tetrahedral and formation of the best hydrogen bond to a neighboring acceptor (AFIX 83) with Ueq(H) = 1.5 Ueq(O). Furthermore, the methanol ligand was refined together with an aqua ligand in the same position. This was done by keeping the oxygen atom as fully occupied and refining the occupancy of the methyl group to a value of ~0.75. Hydrogen atoms on C (binaphthyl) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C), the ones on C (methanol) as an idealized CH3 group (AFIX 133) and Ueq(H) = 1.5 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^+7.7841P] 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 4094 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1384 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1332 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 Cu Cu 0.5000 0.5000 1.0000 0.0358(3) Uani 1 2 d S . . N1 N 0.5150(2) 0.5601(5) 0.8461(4) 0.0380(12) Uani 1 1 d . . . H1A H 0.5420 0.6377 0.8502 0.057 Uiso 1 1 calc R . . H1B H 0.4771 0.5846 0.8064 0.057 Uiso 1 1 calc R . . H1C H 0.5328 0.4846 0.8132 0.057 Uiso 1 1 calc R . . N2 N 0.5837(2) 0.3777(6) 1.0134(4) 0.0468(14) Uani 1 1 d . . . H2A H 0.6172 0.4365 1.0038 0.070 Uiso 1 1 calc R . . H2B H 0.5797 0.3070 0.9615 0.070 Uiso 1 1 calc R . . H2C H 0.5907 0.3363 1.0808 0.070 Uiso 1 1 calc R . . O5 O 0.4362(2) 0.2869(5) 0.9255(4) 0.0576(13) Uani 1 1 d . . . H5A H 0.4240 0.2928 0.8582 0.086 Uiso 1 1 calc R . . C21 C 0.4529(4) 0.1447(10) 0.9524(7) 0.047(3) Uani 0.749(14) 1 d P . . H21A H 0.4901 0.1168 0.9172 0.071 Uiso 0.749(14) 1 calc PR . . H21B H 0.4169 0.0803 0.9272 0.071 Uiso 0.749(14) 1 calc PR . . H21C H 0.4635 0.1361 1.0318 0.071 Uiso 0.749(14) 1 calc PR . . P P 0.35399(6) 0.44422(16) 0.67325(12) 0.0262(3) Uani 1 1 d . . . O1 O 0.30160(15) 0.4193(4) 0.5656(3) 0.0248(8) Uani 1 1 d . . . O2 O 0.30868(14) 0.4959(4) 0.7634(2) 0.0241(8) Uani 1 1 d . . . O3 O 0.38182(16) 0.2969(4) 0.7017(3) 0.0308(9) Uani 1 1 d . . . O4 O 0.39723(16) 0.5708(4) 0.6598(3) 0.0333(9) Uani 1 1 d . . . C1 C 0.2583(2) 0.5349(5) 0.5357(4) 0.0204(11) Uani 1 1 d . . . C2 C 0.2670(3) 0.6181(6) 0.4436(4) 0.0286(13) Uani 1 1 d . . . H2 H 0.3011 0.5962 0.4031 0.034 Uiso 1 1 calc R . . C3 C 0.2262(2) 0.7311(6) 0.4124(4) 0.0289(13) Uani 1 1 d . . . H3 H 0.2313 0.7857 0.3488 0.035 Uiso 1 1 calc R . . C4 C 0.1758(2) 0.7677(6) 0.4751(4) 0.0265(12) Uani 1 1 d . . . C5 C 0.1368(3) 0.8947(6) 0.4511(4) 0.0318(13) Uani 1 1 d . . . H5 H 0.1416 0.9503 0.3879 0.038 Uiso 1 1 calc R . . C6 C 0.0931(2) 0.9376(6) 0.5169(4) 0.0319(13) Uani 1 1 d . . . H6 H 0.0683 1.0228 0.4997 0.038 Uiso 1 1 calc R . . C7 C 0.0846(2) 0.8544(6) 0.6113(4) 0.0302(13) Uani 1 1 d . . . H7 H 0.0545 0.8849 0.6574 0.036 Uiso 1 1 calc R . . C8 C 0.1200(2) 0.7300(6) 0.6360(4) 0.0257(12) Uani 1 1 d . . . H8 H 0.1132 0.6746 0.6984 0.031 Uiso 1 1 calc R . . C9 C 0.1671(2) 0.6822(5) 0.5689(4) 0.0219(11) Uani 1 1 d . . . C10 C 0.2074(2) 0.5556(5) 0.5966(4) 0.0202(11) Uani 1 1 d . . . C11 C 0.2504(2) 0.4229(6) 0.7674(4) 0.0223(11) Uani 1 1 d . . . C12 C 0.2463(3) 0.3261(6) 0.8551(4) 0.0284(13) Uani 1 1 d . . . H12 H 0.2824 0.3103 0.9086 0.034 Uiso 1 1 calc R . . C13 C 0.1894(3) 0.2546(6) 0.8622(4) 0.0308(13) Uani 1 1 d . . . H13 H 0.1864 0.1912 0.9220 0.037 Uiso 1 1 calc R . . C14 C 0.1351(3) 0.2741(6) 0.7816(4) 0.0268(12) Uani 1 1 d . . . C15 C 0.0770(3) 0.1976(6) 0.7859(5) 0.0345(14) Uani 1 1 d . . . H15 H 0.0737 0.1335 0.8453 0.041 Uiso 1 1 calc R . . C16 C 0.0252(3) 0.2139(6) 0.7063(5) 0.0383(15) Uani 1 1 d . . . H16 H -0.0131 0.1613 0.7107 0.046 Uiso 1 1 calc R . . C17 C 0.0297(3) 0.3098(6) 0.6178(5) 0.0333(14) Uani 1 1 d . . . H17 H -0.0059 0.3206 0.5626 0.040 Uiso 1 1 calc R . . C18 C 0.0848(2) 0.3875(6) 0.6108(4) 0.0270(12) Uani 1 1 d . . . H18 H 0.0865 0.4514 0.5508 0.032 Uiso 1 1 calc R . . C19 C 0.1397(2) 0.3738(5) 0.6922(4) 0.0208(11) Uani 1 1 d . . . C20 C 0.1986(2) 0.4526(5) 0.6879(4) 0.0204(11) Uani 1 1 d . . . O6 O 0.4043(2) 0.8263(5) 0.7748(4) 0.0551(13) Uani 1 1 d D . . H6A H 0.374(3) 0.895(7) 0.741(6) 0.083 Uiso 1 1 d D . . H6B H 0.4106 0.7383 0.7419 0.083 Uiso 1 1 d . . . O7 O 0.3257(2) 0.0357(5) 0.6739(7) 0.137(3) Uani 1 1 d . . . H7A H 0.3364 0.1185 0.6983 0.206 Uiso 1 1 calc R . . C22 C 0.2609(3) 0.0286(8) 0.6515(5) 0.0556(19) Uani 1 1 d . . . H22A H 0.2432 0.1272 0.6452 0.083 Uiso 1 1 calc R . . H22B H 0.2437 -0.0232 0.7105 0.083 Uiso 1 1 calc R . . H22C H 0.2491 -0.0234 0.5825 0.083 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 Cu 0.0290(5) 0.0476(7) 0.0295(6) 0.0064(5) -0.0005(4) -0.0002(5) N1 0.032(3) 0.044(3) 0.037(3) 0.007(2) -0.002(2) 0.001(2) N2 0.046(3) 0.061(4) 0.033(3) 0.002(3) 0.005(2) -0.002(3) O5 0.072(3) 0.049(3) 0.046(3) 0.001(2) -0.013(2) -0.007(2) C21 0.059(7) 0.044(7) 0.039(6) 0.001(5) 0.008(5) -0.008(5) P 0.0211(7) 0.0271(8) 0.0294(8) -0.0026(6) 0.0002(6) 0.0026(6) O1 0.0206(18) 0.029(2) 0.0238(19) -0.0035(16) -0.0012(15) 0.0051(16) O2 0.0183(17) 0.030(2) 0.0239(18) -0.0052(16) 0.0014(14) 0.0009(16) O3 0.026(2) 0.026(2) 0.038(2) 0.0010(17) -0.0023(17) 0.0085(17) O4 0.0214(19) 0.031(2) 0.048(2) -0.0020(18) 0.0065(17) -0.0075(17) C1 0.017(2) 0.023(3) 0.021(3) -0.002(2) -0.001(2) -0.003(2) C2 0.029(3) 0.034(3) 0.025(3) -0.003(3) 0.013(2) -0.001(3) C3 0.031(3) 0.031(3) 0.025(3) 0.009(2) 0.003(2) -0.005(3) C4 0.026(3) 0.027(3) 0.024(3) 0.003(2) -0.002(2) -0.002(2) C5 0.036(3) 0.023(3) 0.034(3) 0.009(3) -0.004(3) -0.002(3) C6 0.031(3) 0.022(3) 0.041(3) 0.005(3) -0.003(3) 0.007(3) C7 0.028(3) 0.024(3) 0.038(3) -0.003(3) 0.005(3) 0.004(2) C8 0.022(3) 0.028(3) 0.027(3) 0.004(2) 0.003(2) 0.003(2) C9 0.021(3) 0.025(3) 0.019(3) -0.001(2) 0.001(2) -0.004(2) C10 0.024(3) 0.020(3) 0.015(2) -0.005(2) -0.002(2) -0.004(2) C11 0.023(3) 0.028(3) 0.017(3) -0.004(2) 0.005(2) 0.002(2) C12 0.032(3) 0.031(3) 0.022(3) 0.002(2) 0.001(2) 0.006(3) C13 0.038(3) 0.028(3) 0.027(3) 0.009(2) 0.006(3) 0.002(3) C14 0.035(3) 0.023(3) 0.025(3) 0.000(2) 0.012(2) 0.004(2) C15 0.047(4) 0.028(3) 0.032(3) 0.003(3) 0.019(3) -0.006(3) C16 0.032(3) 0.037(4) 0.049(4) -0.008(3) 0.016(3) -0.013(3) C17 0.029(3) 0.035(3) 0.036(3) -0.008(3) 0.004(3) -0.003(3) C18 0.028(3) 0.025(3) 0.026(3) -0.005(2) -0.001(2) -0.001(2) C19 0.020(3) 0.020(3) 0.023(3) -0.007(2) 0.004(2) -0.002(2) C20 0.027(3) 0.020(3) 0.014(2) 0.001(2) 0.002(2) 0.005(2) O6 0.076(4) 0.037(3) 0.052(3) -0.001(2) 0.006(2) 0.000(2) O7 0.037(3) 0.032(3) 0.332(10) -0.008(4) -0.012(4) 0.000(2) C22 0.053(4) 0.063(5) 0.048(4) -0.010(4) -0.006(3) -0.016(4) _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 Cu N1 2.024(4) 3_667 ? Cu N1 2.024(4) . ? Cu N2 2.059(5) 3_667 ? Cu N2 2.059(5) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N1 H1C 0.9000 . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? N2 H2C 0.9000 . ? O5 C21 1.369(9) . ? O5 H5A 0.8300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? P O3 1.484(4) . ? P O4 1.486(4) . ? P O1 1.611(3) . ? P O2 1.615(3) . ? O1 C1 1.404(5) . ? O2 C11 1.392(6) . ? C1 C10 1.388(6) . ? C1 C2 1.388(7) . ? C2 C3 1.358(7) . ? C2 H2 0.9400 . ? C3 C4 1.422(7) . ? C3 H3 0.9400 . ? C4 C9 1.418(7) . ? C4 C5 1.421(7) . ? C5 C6 1.353(7) . ? C5 H5 0.9400 . ? C6 C7 1.411(7) . ? C6 H6 0.9400 . ? C7 C8 1.363(7) . ? C7 H7 0.9400 . ? C8 C9 1.430(7) . ? C8 H8 0.9400 . ? C9 C10 1.439(7) . ? C10 C20 1.488(6) . ? C11 C20 1.380(6) . ? C11 C12 1.399(7) . ? C12 C13 1.366(7) . ? C12 H12 0.9400 . ? C13 C14 1.412(7) . ? C13 H13 0.9400 . ? C14 C15 1.405(7) . ? C14 C19 1.433(7) . ? C15 C16 1.362(8) . ? C15 H15 0.9400 . ? C16 C17 1.403(8) . ? C16 H16 0.9400 . ? C17 C18 1.363(7) . ? C17 H17 0.9400 . ? C18 C19 1.420(7) . ? C18 H18 0.9400 . ? C19 C20 1.430(7) . ? O6 H6A 0.95(6) . ? O6 H6B 0.9138 . ? O7 C22 1.345(7) . ? O7 H7A 0.8300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu N1 180.000(1) 3_667 . ? N1 Cu N2 89.15(18) 3_667 3_667 ? N1 Cu N2 90.85(18) . 3_667 ? N1 Cu N2 90.85(18) 3_667 . ? N1 Cu N2 89.15(18) . . ? N2 Cu N2 180.000(1) 3_667 . ? Cu N1 H1A 109.5 . . ? Cu N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? Cu N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? Cu N2 H2A 109.5 . . ? Cu N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? Cu N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C21 O5 H5A 109.5 . . ? O5 C21 H21A 109.5 . . ? O5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O3 P O4 120.1(2) . . ? O3 P O1 105.4(2) . . ? O4 P O1 112.0(2) . . ? O3 P O2 110.4(2) . . ? O4 P O2 105.6(2) . . ? O1 P O2 101.76(17) . . ? C1 O1 P 116.8(3) . . ? C11 O2 P 118.6(3) . . ? C10 C1 C2 123.6(5) . . ? C10 C1 O1 118.3(4) . . ? C2 C1 O1 118.0(4) . . ? C3 C2 C1 119.7(5) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 120.5(5) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C9 C4 C5 118.9(5) . . ? C9 C4 C3 119.4(5) . . ? C5 C4 C3 121.5(5) . . ? C6 C5 C4 121.6(5) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 120.0(5) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C8 C7 C6 120.3(5) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 121.3(5) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C4 C9 C8 117.9(5) . . ? C4 C9 C10 119.7(4) . . ? C8 C9 C10 122.3(4) . . ? C1 C10 C9 116.6(4) . . ? C1 C10 C20 119.7(4) . . ? C9 C10 C20 123.6(4) . . ? C20 C11 O2 119.2(4) . . ? C20 C11 C12 122.7(5) . . ? O2 C11 C12 118.0(4) . . ? C13 C12 C11 119.4(5) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.3(5) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 121.9(5) . . ? C15 C14 C19 119.3(5) . . ? C13 C14 C19 118.8(5) . . ? C16 C15 C14 121.6(5) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 119.5(5) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C18 C17 C16 121.0(5) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 121.3(5) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C20 123.2(5) . . ? C18 C19 C14 117.3(5) . . ? C20 C19 C14 119.5(4) . . ? C11 C20 C19 118.2(4) . . ? C11 C20 C10 119.2(4) . . ? C19 C20 C10 122.4(4) . . ? H6A O6 H6B 121.0 . . ? C22 O7 H7A 109.5 . . ? O7 C22 H22A 109.5 . . ? O7 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O7 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? 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 O3 0.90 2.30 3.155(6) 158.1 2_656 N1 H1B O4 0.90 2.28 3.122(5) 155.1 . N1 H1C O6 0.90 2.31 3.195(7) 167.7 2_646 N2 H2C O6 0.90 2.30 3.169(7) 163.6 3_667 O5 H5A O3 0.83 2.00 2.821(5) 171.4 . O6 H6A O7 0.95(6) 1.76(6) 2.703(7) 172(7) 1_565 O6 H6B O4 0.91 1.83 2.711(6) 162.5 . O7 H7A O3 0.83 1.88 2.651(6) 154.7 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.10 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.968 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.101 # Attachment '5_Cu-H2O-MeOH.cif' data_thomlm _database_code_depnum_ccdc_archive 'CCDC 286358' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (trans-diaqua-tetramethanol-copper(II))-bis(rac-1,1'- binaphthalene-2,2'-diylphosphate).hydrate.dimethanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H54 Cu O17 P2' _chemical_formula_weight 1004.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 41.876(6) _cell_length_b 8.6579(13) _cell_length_c 13.225(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.860(3) _cell_angle_gamma 90.00 _cell_volume 4612.5(12) _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 plate _exptl_crystal_colour 'pale greenish-blue' _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2100 _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7180 _exptl_absorpt_correction_T_max 0.9805 _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 17890 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.0762 _diffrn_reflns_limit_h_min -51 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.01 _diffrn_reflns_theta_max 26.05 _reflns_number_total 4565 _reflns_number_gt 2483 _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 hydrogen atoms on the aqua ligands and the hydrogen atom on the water of crystallization were found and refined with Ueq(H) = 1.5 Ueq(O). The hydrogen atoms on the methanol molecules could be found and refined but the ones on the methanol ligands were eventually prefered to place at calculated positions as an idealized OH-group with C-O-H angle tetrahedral and formation of the best hydrogen bond to a neighboring acceptor (AFIX 83) with Ueq(H) = 1.5 Ueq(N). The methanol of crystallization was still fully refined with Ueq(H) = 1.5 Ueq(O). Hydrogen atoms on C (binaphthyl) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C), the ones on C (methanol) as an idealized CH3 group (AFIX 133) and Ueq(H) = 1.5 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^+21.2945P] 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 4565 _refine_ls_number_parameters 294 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1475 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.283 _refine_ls_restrained_S_all 1.282 _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 Cu Cu 0.0000 0.0000 0.0000 0.0320(2) Uani 1 2 d S . . O5 O 0.03707(10) 0.0037(5) 0.1253(3) 0.0469(10) Uani 1 1 d D . . H51 H 0.0386(15) -0.072(6) 0.176(4) 0.070 Uiso 1 1 d D . . H52 H 0.0520(15) 0.086(7) 0.132(5) 0.070 Uiso 1 1 d . . . O6 O -0.02268(9) -0.1847(4) 0.0586(3) 0.0457(10) Uani 1 1 d . . . H61 H -0.0237 -0.1722 0.1198 0.069 Uiso 1 1 calc R . . C21 C -0.0189 -0.3449 0.0399 0.059 Uani 1 1 d . . . H21A H -0.0317 -0.4051 0.0767 0.088 Uiso 1 1 calc R . . H21B H 0.0043 -0.3731 0.0653 0.088 Uiso 1 1 calc R . . H21C H -0.0267 -0.3656 -0.0349 0.088 Uiso 1 1 calc R . . O7 O -0.02509(10) 0.1550(5) 0.0818(3) 0.0646(13) Uani 1 1 d . . . H71 H -0.0144 0.2263 0.1175 0.097 Uiso 1 1 calc R . . C22 C -0.0578 0.1849 0.0611 0.099 Uani 1 1 d . . . H22A H -0.0615 0.2594 0.1114 0.148 Uiso 1 1 calc R . . H22B H -0.0696 0.0902 0.0662 0.148 Uiso 1 1 calc R . . H22C H -0.0658 0.2266 -0.0094 0.148 Uiso 1 1 calc R . . P P 0.07161(3) 0.65914(16) 0.27191(11) 0.0293(3) Uani 1 1 d . . . O1 O 0.09981(8) 0.6388(4) 0.3820(2) 0.0292(8) Uani 1 1 d . . . O2 O 0.09336(8) 0.7144(4) 0.1949(2) 0.0312(8) Uani 1 1 d . . . O3 O 0.05739(8) 0.5026(4) 0.2437(3) 0.0377(9) Uani 1 1 d . . . O4 O 0.04909(8) 0.7900(4) 0.2757(3) 0.0339(9) Uani 1 1 d . . . C1 C 0.12413(12) 0.6493(6) 0.2024(4) 0.0292(12) Uani 1 1 d . . . C2 C 0.12699(13) 0.5535(6) 0.1195(4) 0.0347(13) Uani 1 1 d . . . H2 H 0.1083 0.5318 0.0632 0.042 Uiso 1 1 calc R . . C3 C 0.15719(13) 0.4924(6) 0.1215(4) 0.0368(13) Uani 1 1 d . . . H3 H 0.1593 0.4312 0.0650 0.044 Uiso 1 1 calc R . . C4 C 0.18519(12) 0.5189(6) 0.2062(4) 0.0333(12) Uani 1 1 d . . . C5 C 0.21648(14) 0.4521(6) 0.2113(5) 0.0425(15) Uani 1 1 d . . . H5 H 0.2189 0.3911 0.1551 0.051 Uiso 1 1 calc R . . C6 C 0.24309(14) 0.4742(7) 0.2955(5) 0.0446(15) Uani 1 1 d . . . H6 H 0.2636 0.4286 0.2973 0.054 Uiso 1 1 calc R . . C7 C 0.23984(13) 0.5652(6) 0.3797(5) 0.0402(14) Uani 1 1 d . . . H7 H 0.2583 0.5797 0.4381 0.048 Uiso 1 1 calc R . . C8 C 0.21028(12) 0.6330(6) 0.3782(4) 0.0329(12) Uani 1 1 d . . . H8 H 0.2085 0.6922 0.4360 0.039 Uiso 1 1 calc R . . C9 C 0.18229(12) 0.6155(5) 0.2908(4) 0.0275(11) Uani 1 1 d . . . C10 C 0.15075(11) 0.6870(5) 0.2852(4) 0.0245(11) Uani 1 1 d . . . C11 C 0.12102(12) 0.7645(6) 0.4159(4) 0.0280(12) Uani 1 1 d . . . C12 C 0.11614(12) 0.8541(6) 0.4992(4) 0.0350(13) Uani 1 1 d . . . H12 H 0.0990 0.8301 0.5299 0.042 Uiso 1 1 calc R . . C13 C 0.13666(12) 0.9758(7) 0.5345(4) 0.0385(14) Uani 1 1 d . . . H13 H 0.1345 1.0319 0.5932 0.046 Uiso 1 1 calc R . . C14 C 0.16107(12) 1.0197(6) 0.4851(4) 0.0319(12) Uani 1 1 d . . . C15 C 0.17994(13) 1.1555(6) 0.5143(5) 0.0407(14) Uani 1 1 d . . . H15 H 0.1775 1.2134 0.5718 0.049 Uiso 1 1 calc R . . C16 C 0.20161(14) 1.2045(6) 0.4613(5) 0.0491(16) Uani 1 1 d . . . H16 H 0.2138 1.2959 0.4816 0.059 Uiso 1 1 calc R . . C17 C 0.20574(13) 1.1178(6) 0.3758(5) 0.0414(15) Uani 1 1 d . . . H17 H 0.2205 1.1525 0.3384 0.050 Uiso 1 1 calc R . . C18 C 0.18853(11) 0.9837(6) 0.3466(4) 0.0308(12) Uani 1 1 d . . . H18 H 0.1919 0.9265 0.2900 0.037 Uiso 1 1 calc R . . C19 C 0.16569(12) 0.9293(5) 0.4002(4) 0.0274(11) Uani 1 1 d . . . C20 C 0.14586(11) 0.7928(5) 0.3688(4) 0.0239(11) Uani 1 1 d . . . O8 O 0.0000 0.3475(7) 0.2500 0.0457(15) Uani 1 2 d S . . H81 H 0.0176(13) 0.401(7) 0.253(5) 0.069 Uiso 1 1 d . . . O9 O 0.07982(10) 0.2344(4) 0.1885(3) 0.0422(10) Uani 1 1 d . . . H91 H 0.0729(15) 0.318(7) 0.191(5) 0.063 Uiso 1 1 d . . . C23 C 0.11041(14) 0.2009(8) 0.2622(5) 0.0590(18) Uani 1 1 d . . . H23A H 0.1283 0.2481 0.2397 0.088 Uiso 1 1 calc R . . H23B H 0.1136 0.0899 0.2672 0.088 Uiso 1 1 calc R . . H23C H 0.1103 0.2416 0.3304 0.088 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 Cu 0.0364(5) 0.0275(5) 0.0307(5) 0.0013(4) 0.0066(4) -0.0002(4) O5 0.052(2) 0.038(2) 0.042(2) 0.013(2) -0.0037(19) -0.011(2) O6 0.062(3) 0.040(2) 0.038(2) -0.0018(19) 0.019(2) 0.001(2) C21 0.066 0.050 0.063 -0.004 0.023 0.011 O7 0.043(3) 0.066(3) 0.079(3) -0.024(3) 0.007(2) -0.004(2) C22 0.041 0.179 0.072 -0.038 0.009 0.015 P 0.0259(7) 0.0275(7) 0.0341(8) 0.0027(6) 0.0074(6) -0.0018(6) O1 0.0308(19) 0.029(2) 0.0280(19) 0.0052(16) 0.0078(15) -0.0018(16) O2 0.0236(18) 0.039(2) 0.030(2) 0.0024(17) 0.0059(16) -0.0019(16) O3 0.0300(19) 0.033(2) 0.050(2) -0.006(2) 0.0105(17) -0.0085(18) O4 0.034(2) 0.029(2) 0.039(2) 0.0067(17) 0.0098(17) 0.0076(16) C1 0.028(3) 0.029(3) 0.033(3) 0.004(2) 0.013(2) -0.002(2) C2 0.036(3) 0.036(3) 0.032(3) 0.000(2) 0.010(3) -0.008(2) C3 0.045(3) 0.033(3) 0.037(3) -0.014(3) 0.019(3) -0.014(3) C4 0.036(3) 0.034(3) 0.036(3) 0.001(3) 0.019(2) -0.002(3) C5 0.046(4) 0.037(3) 0.054(4) 0.000(3) 0.031(3) 0.002(3) C6 0.035(3) 0.046(4) 0.056(4) 0.008(3) 0.019(3) 0.010(3) C7 0.031(3) 0.042(3) 0.048(4) 0.003(3) 0.012(3) 0.000(3) C8 0.034(3) 0.029(3) 0.037(3) 0.005(2) 0.012(3) 0.003(2) C9 0.026(3) 0.022(3) 0.035(3) 0.004(2) 0.009(2) -0.004(2) C10 0.028(3) 0.021(3) 0.026(3) 0.002(2) 0.008(2) -0.005(2) C11 0.024(3) 0.026(3) 0.031(3) 0.003(2) 0.003(2) 0.002(2) C12 0.030(3) 0.045(3) 0.031(3) 0.001(3) 0.010(2) 0.005(3) C13 0.037(3) 0.047(4) 0.029(3) -0.008(3) 0.004(2) 0.008(3) C14 0.030(3) 0.030(3) 0.033(3) 0.000(3) 0.003(2) 0.006(2) C15 0.036(3) 0.030(3) 0.051(4) -0.013(3) 0.002(3) 0.000(3) C16 0.038(3) 0.025(3) 0.073(5) -0.006(3) -0.004(3) -0.004(3) C17 0.034(3) 0.032(3) 0.057(4) 0.005(3) 0.010(3) -0.006(3) C18 0.028(3) 0.025(3) 0.037(3) 0.003(3) 0.006(2) 0.001(2) C19 0.025(3) 0.024(3) 0.030(3) 0.001(2) 0.002(2) 0.004(2) C20 0.024(3) 0.024(3) 0.023(3) 0.005(2) 0.004(2) 0.001(2) O8 0.025(3) 0.038(3) 0.073(4) 0.000 0.013(3) 0.000 O9 0.035(2) 0.037(2) 0.049(3) 0.002(2) 0.0026(19) 0.0056(19) C23 0.048(4) 0.070(5) 0.051(4) 0.007(4) 0.000(3) 0.021(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu O5 1.937(4) 5 ? Cu O5 1.937(4) . ? Cu O6 2.112(4) . ? Cu O6 2.112(4) 5 ? Cu O7 2.167(4) . ? Cu O7 2.167(4) 5 ? O5 H51 0.93(4) . ? O5 H52 0.94(6) . ? O6 C21 1.425(4) . ? O6 H61 0.8300 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? O7 C22 1.346(4) . ? O7 H71 0.8300 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 H22C 0.9700 . ? P O4 1.483(3) . ? P O3 1.486(4) . ? P O2 1.614(3) . ? P O1 1.614(3) . ? O1 C11 1.399(6) . ? O2 C1 1.385(6) . ? C1 C10 1.372(6) . ? C1 C2 1.405(7) . ? C2 C3 1.364(7) . ? C2 H2 0.9400 . ? C3 C4 1.401(7) . ? C3 H3 0.9400 . ? C4 C5 1.417(7) . ? C4 C9 1.429(7) . ? C5 C6 1.356(7) . ? C5 H5 0.9400 . ? C6 C7 1.401(7) . ? C6 H6 0.9400 . ? C7 C8 1.365(7) . ? C7 H7 0.9400 . ? C8 C9 1.411(7) . ? C8 H8 0.9400 . ? C9 C10 1.442(6) . ? C10 C20 1.492(6) . ? C11 C20 1.373(6) . ? C11 C12 1.406(7) . ? C12 C13 1.359(7) . ? C12 H12 0.9400 . ? C13 C14 1.408(7) . ? C13 H13 0.9400 . ? C14 C15 1.411(7) . ? C14 C19 1.425(7) . ? C15 C16 1.358(8) . ? C15 H15 0.9400 . ? C16 C17 1.406(8) . ? C16 H16 0.9400 . ? C17 C18 1.365(7) . ? C17 H17 0.9400 . ? C18 C19 1.417(6) . ? C18 H18 0.9400 . ? C19 C20 1.439(6) . ? O8 H81 0.86(5) . ? O9 C23 1.412(6) . ? O9 H91 0.78(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 H23C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu O5 180.0(2) 5 . ? O5 Cu O6 88.03(16) 5 . ? O5 Cu O6 91.97(16) . . ? O5 Cu O6 91.97(16) 5 5 ? O5 Cu O6 88.03(16) . 5 ? O6 Cu O6 180.0(3) . 5 ? O5 Cu O7 93.03(17) 5 . ? O5 Cu O7 86.97(17) . . ? O6 Cu O7 87.58(15) . . ? O6 Cu O7 92.42(15) 5 . ? O5 Cu O7 86.97(17) 5 5 ? O5 Cu O7 93.03(17) . 5 ? O6 Cu O7 92.42(15) . 5 ? O6 Cu O7 87.58(15) 5 5 ? O7 Cu O7 180.0(2) . 5 ? Cu O5 H51 119(4) . . ? Cu O5 H52 117(4) . . ? H51 O5 H52 123(5) . . ? C21 O6 Cu 126.2(2) . . ? C21 O6 H61 109.5 . . ? Cu O6 H61 114.0 . . ? O6 C21 H21A 109.5 . . ? O6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C22 O7 Cu 128.5(3) . . ? C22 O7 H71 109.5 . . ? Cu O7 H71 119.0 . . ? O7 C22 H22A 109.5 . . ? O7 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O7 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O4 P O3 119.4(2) . . ? O4 P O2 105.60(19) . . ? O3 P O2 111.6(2) . . ? O4 P O1 111.6(2) . . ? O3 P O1 105.73(19) . . ? O2 P O1 101.62(18) . . ? C11 O1 P 116.6(3) . . ? C1 O2 P 120.6(3) . . ? C10 C1 O2 119.8(4) . . ? C10 C1 C2 122.6(5) . . ? O2 C1 C2 117.4(4) . . ? C3 C2 C1 119.3(5) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 121.4(5) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 122.2(5) . . ? C3 C4 C9 119.3(5) . . ? C5 C4 C9 118.5(5) . . ? C6 C5 C4 121.6(5) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C7 119.7(5) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 121.0(5) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 120.8(5) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 118.4(5) . . ? C8 C9 C10 122.7(5) . . ? C4 C9 C10 118.9(4) . . ? C1 C10 C9 118.2(4) . . ? C1 C10 C20 119.5(4) . . ? C9 C10 C20 122.3(4) . . ? C20 C11 O1 119.1(4) . . ? C20 C11 C12 123.2(5) . . ? O1 C11 C12 117.7(4) . . ? C13 C12 C11 118.9(5) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 121.4(5) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C15 121.4(5) . . ? C13 C14 C19 119.4(5) . . ? C15 C14 C19 119.2(5) . . ? C16 C15 C14 121.5(5) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 119.7(5) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C18 C17 C16 120.7(5) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 121.2(5) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C18 C19 C14 117.8(5) . . ? C18 C19 C20 123.0(4) . . ? C14 C19 C20 119.1(4) . . ? C11 C20 C19 117.7(4) . . ? C11 C20 C10 120.1(4) . . ? C19 C20 C10 122.2(4) . . ? C23 O9 H91 116(5) . . ? O9 C23 H23A 109.5 . . ? O9 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O9 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? 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 O5 H51 O4 0.93(4) 1.74(4) 2.662(5) 170(6) 1_545 O5 H52 O9 0.94(6) 1.76(6) 2.660(6) 161(6) . O6 H61 O4 0.83 1.99 2.721(5) 146.8 2_545 O7 H71 O8 0.83 1.99 2.748(5) 151.6 . O8 H81 O3 0.86(5) 1.92(5) 2.774(4) 172(6) . O9 H91 O3 0.78(6) 1.93(6) 2.679(5) 162(7) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.05 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.533 _refine_diff_density_min -0.635 _refine_diff_density_rms 0.101 # Attachment '6_Ni-en2-100K.CIF' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 286359' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (cis-diaqua-bis(ethylene diamine)-nickel(II))-bis(rac-1,1'- binaphthalene-2,2'-diylphosphate).dihydrate.dimethanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H56 N4 Ni O14 P2' _chemical_formula_weight 1009.60 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' Ni Ni 0.3393 1.1124 '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 42.5440(18) _cell_length_b 9.0870(4) _cell_length_c 12.3730(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.7550(19) _cell_angle_gamma 90.00 _cell_volume 4727.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2120 _exptl_absorpt_coefficient_mu 0.549 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8269 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius Kappa CCD diffractometer' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7505 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0360 _diffrn_reflns_limit_h_min -53 _diffrn_reflns_limit_h_max 53 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 26.70 _reflns_number_total 7505 _reflns_number_gt 7043 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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 hydrogen atoms of the aqua ligands and the water of crystallization were initially found but had to be fixed upon further refinement with Ueq(H) = 1.5 Ueq(O). The hydrogen atoms of the ethylene diamine ligands were calculated as an idealized C/NH2 groups with tetrahedral angles (AFIX 23) and Ueq(H) = 1.2 Ueq(C/N). The methanolic O-H were placed at calculated positions as an idealized OH-group with C-O-H angle tetrahedral and formation of the best hydrogen bond to a neighboring acceptor (AFIX 83) with Ueq(H) = 1.5 Ueq(O). Hydrogen atoms on C (binaphthyl) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C), the ones on C (methanol) as an idealized CH3 group (AFIX 133) and Ueq(H) = 1.5 Ueq(C). The structure was solved and refined in the non-centrosymmetric polar space group Cc with racemic twinning (twin law 1 0 0 0 1 0 0 0 1 and BASF 0.50563. Structure solution and refinement was also carried out in the centrosymmetric space group C2/c. However, the Ni(en)2(H2O)2 fragment was then found crystallographically disordered due to the two-fold rotation axis in the vicinity of the nickel atom. The disorder could be fully resolved, yet, refinement did not progress below R1 = 0.1770 for 6113 data with Fo > 4sig(Fo) and R1 = 0.1832 and wR2 = 0.4414 for all 6666 data. The data set was also measured at T = 200(2) K on a Bruker AXS CCD diffractometer with a similar result in terms of refinements in Cc anc C2/c as stated above. ; _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^)+(0.0575P)^2^+9.9327P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(11) _refine_ls_number_reflns 7505 _refine_ls_number_parameters 605 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.007 _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 Ni Ni 0.802941(13) 0.53675(5) 0.08113(3) 0.01486(10) Uani 1 1 d . . . O1 O 0.84907(7) 0.5359(3) 0.1726(2) 0.0188(6) Uani 1 1 d . . . H1C H 0.8536 0.6072 0.2003 0.028 Uiso 1 1 d . . . H1D H 0.8514 0.4729 0.2087 0.028 Uiso 1 1 d . . . O2 O 0.78896(7) 0.6255(3) 0.2272(2) 0.0184(5) Uani 1 1 d . . . H2C H 0.7910 0.7111 0.2375 0.028 Uiso 1 1 d . . . H2D H 0.7674 0.5973 0.2454 0.028 Uiso 1 1 d . . . N1 N 0.75551(8) 0.5553(4) 0.0037(3) 0.0198(7) Uani 1 1 d . . . H1E H 0.7527 0.5046 -0.0614 0.024 Uiso 1 1 calc R . . H1F H 0.7419 0.5172 0.0476 0.024 Uiso 1 1 calc R . . C1 C 0.74901(9) 0.7149(5) -0.0163(3) 0.0243(9) Uani 1 1 d . . . H1A H 0.7457 0.7641 0.0525 0.029 Uiso 1 1 calc R . . H1B H 0.7296 0.7279 -0.0705 0.029 Uiso 1 1 calc R . . C2 C 0.77724(11) 0.7808(5) -0.0588(3) 0.0271(9) Uani 1 1 d . . . H2A H 0.7792 0.7373 -0.1308 0.032 Uiso 1 1 calc R . . H2B H 0.7742 0.8882 -0.0685 0.032 Uiso 1 1 calc R . . N2 N 0.80651(8) 0.7516(4) 0.0193(3) 0.0220(7) Uani 1 1 d . . . H2E H 0.8085 0.8190 0.0754 0.026 Uiso 1 1 calc R . . H2F H 0.8241 0.7590 -0.0155 0.026 Uiso 1 1 calc R . . N3 N 0.79707(7) 0.3186(3) 0.1268(2) 0.0184(6) Uani 1 1 d . . . H3C H 0.8107 0.2975 0.1900 0.022 Uiso 1 1 calc R . . H3D H 0.7766 0.3036 0.1395 0.022 Uiso 1 1 calc R . . C3 C 0.80398(10) 0.2222(4) 0.0372(3) 0.0227(8) Uani 1 1 d . . . H3A H 0.7850 0.2149 -0.0197 0.027 Uiso 1 1 calc R . . H3B H 0.8094 0.1222 0.0658 0.027 Uiso 1 1 calc R . . C4 C 0.83170(10) 0.2864(4) -0.0119(3) 0.0229(8) Uani 1 1 d . . . H4A H 0.8513 0.2832 0.0424 0.027 Uiso 1 1 calc R . . H4B H 0.8353 0.2282 -0.0766 0.027 Uiso 1 1 calc R . . N4 N 0.82395(7) 0.4394(4) -0.0440(3) 0.0189(7) Uani 1 1 d . . . H4C H 0.8101 0.4417 -0.1088 0.023 Uiso 1 1 calc R . . H4D H 0.8421 0.4896 -0.0534 0.023 Uiso 1 1 calc R . . P1 P 0.86711(2) 0.17984(10) 0.31918(7) 0.01407(18) Uani 1 1 d . . . O3 O 0.89405(6) 0.1589(3) 0.4247(2) 0.0149(5) Uani 1 1 d . . . O4 O 0.88813(6) 0.2198(3) 0.22460(19) 0.0163(5) Uani 1 1 d . . . O5 O 0.85071(6) 0.0356(3) 0.2994(2) 0.0216(6) Uani 1 1 d . . . O6 O 0.84726(6) 0.3131(3) 0.3297(2) 0.0176(5) Uani 1 1 d . . . C10 C 0.91449(8) 0.2797(4) 0.4491(3) 0.0140(7) Uani 1 1 d . . . C11 C 0.90970(9) 0.3688(5) 0.5377(3) 0.0190(8) Uani 1 1 d . . . H11 H 0.8934 0.3459 0.5797 0.023 Uiso 1 1 calc R . . C12 C 0.92866(9) 0.4882(4) 0.5628(3) 0.0187(8) Uani 1 1 d . . . H12 H 0.9260 0.5470 0.6242 0.022 Uiso 1 1 calc R . . C13 C 0.95241(8) 0.5263(4) 0.4982(3) 0.0170(7) Uani 1 1 d . . . C14 C 0.97053(9) 0.6572(4) 0.5172(3) 0.0214(8) Uani 1 1 d . . . H14 H 0.9681 0.7165 0.5786 0.026 Uiso 1 1 calc R . . C15 C 0.99127(10) 0.7005(4) 0.4501(3) 0.0237(8) Uani 1 1 d . . . H15 H 1.0027 0.7902 0.4633 0.028 Uiso 1 1 calc R . . C16 C 0.99576(10) 0.6103(4) 0.3602(3) 0.0231(8) Uani 1 1 d . . . H16 H 1.0103 0.6397 0.3132 0.028 Uiso 1 1 calc R . . C17 C 0.97923(8) 0.4807(4) 0.3405(3) 0.0168(7) Uani 1 1 d . . . H17 H 0.9826 0.4215 0.2799 0.020 Uiso 1 1 calc R . . C18 C 0.95728(8) 0.4337(4) 0.4088(3) 0.0136(7) Uani 1 1 d . . . C19 C 0.93843(8) 0.3027(4) 0.3872(3) 0.0125(7) Uani 1 1 d . . . C20 C 0.91769(8) 0.1549(4) 0.2229(3) 0.0146(7) Uani 1 1 d . . . C21 C 0.92023(9) 0.0557(4) 0.1366(3) 0.0172(7) Uani 1 1 d . . . H21 H 0.9022 0.0336 0.0837 0.021 Uiso 1 1 calc R . . C22 C 0.94905(9) -0.0078(4) 0.1305(3) 0.0196(8) Uani 1 1 d . . . H22 H 0.9511 -0.0728 0.0718 0.024 Uiso 1 1 calc R . . C23 C 0.97597(9) 0.0217(4) 0.2105(3) 0.0166(7) Uani 1 1 d . . . C24 C 1.00543(9) -0.0492(5) 0.2072(3) 0.0221(8) Uani 1 1 d . . . H24 H 1.0076 -0.1137 0.1484 0.027 Uiso 1 1 calc R . . C25 C 1.03091(9) -0.0260(5) 0.2879(3) 0.0229(8) Uani 1 1 d . . . H25 H 1.0505 -0.0751 0.2850 0.027 Uiso 1 1 calc R . . C26 C 1.02803(9) 0.0713(5) 0.3754(3) 0.0209(8) Uani 1 1 d . . . H26 H 1.0457 0.0868 0.4313 0.025 Uiso 1 1 calc R . . C27 C 1.00001(9) 0.1427(4) 0.3797(3) 0.0165(7) Uani 1 1 d . . . H27 H 0.9985 0.2078 0.4387 0.020 Uiso 1 1 calc R . . C28 C 0.97318(8) 0.1218(4) 0.2981(3) 0.0139(7) Uani 1 1 d . . . C29 C 0.94312(8) 0.1948(4) 0.2999(3) 0.0133(7) Uani 1 1 d . . . P2 P 1.21136(2) 0.32115(10) 0.66047(7) 0.01457(19) Uani 1 1 d . . . O7 O 1.18933(6) 0.2795(3) 0.7516(2) 0.0162(5) Uani 1 1 d . . . O8 O 1.18503(6) 0.3457(3) 0.55318(19) 0.0151(5) Uani 1 1 d . . . O9 O 1.23062(6) 0.1876(3) 0.6493(2) 0.0192(6) Uani 1 1 d . . . O10 O 1.22763(6) 0.4642(3) 0.6844(2) 0.0220(6) Uani 1 1 d . . . C30 C 1.15988(8) 0.3455(4) 0.7512(3) 0.0135(7) Uani 1 1 d . . . C31 C 1.15664(9) 0.4431(4) 0.8364(3) 0.0174(7) Uani 1 1 d . . . H31 H 1.1743 0.4641 0.8908 0.021 Uiso 1 1 calc R . . C32 C 1.12791(9) 0.5077(4) 0.8408(3) 0.0192(8) Uani 1 1 d . . . H32 H 1.1255 0.5718 0.8996 0.023 Uiso 1 1 calc R . . C33 C 1.10161(8) 0.4798(4) 0.7582(3) 0.0154(7) Uani 1 1 d . . . C34 C 1.07215(10) 0.5534(4) 0.7590(3) 0.0212(9) Uani 1 1 d . . . H34 H 1.0697 0.6176 0.8178 0.025 Uiso 1 1 calc R . . C35 C 1.04724(9) 0.5329(5) 0.6761(3) 0.0235(8) Uani 1 1 d . . . H35 H 1.0278 0.5835 0.6772 0.028 Uiso 1 1 calc R . . C36 C 1.05059(8) 0.4367(4) 0.5893(3) 0.0207(8) Uani 1 1 d . . . H36 H 1.0333 0.4229 0.5319 0.025 Uiso 1 1 calc R . . C37 C 1.07874(8) 0.3625(4) 0.5871(3) 0.0159(7) Uani 1 1 d . . . H37 H 1.0807 0.2981 0.5279 0.019 Uiso 1 1 calc R . . C38 C 1.10488(8) 0.3810(4) 0.6719(3) 0.0137(7) Uani 1 1 d . . . C39 C 1.13480(8) 0.3076(4) 0.6707(3) 0.0123(7) Uani 1 1 d . . . C40 C 1.16445(8) 0.2267(4) 0.5244(3) 0.0131(6) Uani 1 1 d . . . C41 C 1.16992(9) 0.1399(4) 0.4347(3) 0.0181(7) Uani 1 1 d . . . H41 H 1.1868 0.1630 0.3954 0.022 Uiso 1 1 calc R . . C42 C 1.15073(9) 0.0229(5) 0.4055(3) 0.0200(8) Uani 1 1 d . . . H42 H 1.1535 -0.0333 0.3429 0.024 Uiso 1 1 calc R . . C43 C 1.12656(9) -0.0166(4) 0.4671(3) 0.0162(7) Uani 1 1 d . . . C44 C 1.10843(9) -0.1486(4) 0.4436(3) 0.0203(8) Uani 1 1 d . . . H44 H 1.1114 -0.2069 0.3823 0.024 Uiso 1 1 calc R . . C45 C 1.08689(10) -0.1915(4) 0.5083(3) 0.0225(8) Uani 1 1 d . . . H45 H 1.0750 -0.2792 0.4918 0.027 Uiso 1 1 calc R . . C46 C 1.08221(9) -0.1063(4) 0.5995(3) 0.0209(8) Uani 1 1 d . . . H46 H 1.0676 -0.1385 0.6453 0.025 Uiso 1 1 calc R . . C47 C 1.09864(8) 0.0229(4) 0.6230(3) 0.0176(7) Uani 1 1 d . . . H47 H 1.0949 0.0799 0.6842 0.021 Uiso 1 1 calc R . . C48 C 1.12101(8) 0.0722(4) 0.5574(3) 0.0135(7) Uani 1 1 d . . . C49 C 1.14003(8) 0.2024(4) 0.5835(3) 0.0125(7) Uani 1 1 d . . . O11 O 0.79056(7) 0.9260(3) 0.2208(3) 0.0273(6) Uani 1 1 d . . . H11A H 0.7749 0.9701 0.2026 0.041 Uiso 1 1 d . . . H11B H 0.8046 0.9661 0.2659 0.041 Uiso 1 1 d . . . O12 O 1.23254(7) 0.9478(3) 0.7775(2) 0.0235(6) Uani 1 1 d . . . H12A H 1.2184 0.8596 0.7642 0.035 Uiso 1 1 d . . . H12B H 1.2260 1.0200 0.7318 0.035 Uiso 1 1 d . . . O13 O 0.87678(7) 0.7839(3) 0.2499(2) 0.0256(6) Uani 1 1 d . . . H13A H 0.8692 0.8668 0.2609 0.038 Uiso 1 1 calc R . . C5 C 0.90482(11) 0.7603(5) 0.3263(3) 0.0305(9) Uani 1 1 d . . . H5A H 0.9188 0.8462 0.3271 0.046 Uiso 1 1 calc R . . H5B H 0.9159 0.6729 0.3050 0.046 Uiso 1 1 calc R . . H5C H 0.8991 0.7456 0.3993 0.046 Uiso 1 1 calc R . . O14 O 1.19680(8) 0.7151(3) 0.7160(2) 0.0275(6) Uani 1 1 d . . . H14A H 1.2049 0.6312 0.7126 0.041 Uiso 1 1 calc R . . C6 C 1.16913(11) 0.7259(5) 0.6369(4) 0.0312(9) Uani 1 1 d . . . H6A H 1.1557 0.8059 0.6568 0.047 Uiso 1 1 calc R . . H6B H 1.1573 0.6330 0.6339 0.047 Uiso 1 1 calc R . . H6C H 1.1752 0.7463 0.5651 0.047 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 Ni 0.01457(18) 0.0153(2) 0.01501(19) 0.0009(2) 0.00306(13) -0.00070(19) O1 0.0165(13) 0.0163(14) 0.0230(14) 0.0013(11) 0.0009(11) -0.0029(11) O2 0.0188(11) 0.0177(12) 0.0198(12) -0.0020(11) 0.0058(9) -0.0007(12) N1 0.0164(16) 0.0251(19) 0.0177(16) 0.0033(13) 0.0021(12) 0.0000(13) C1 0.0207(19) 0.029(2) 0.0215(19) 0.0005(17) -0.0032(15) 0.0087(17) C2 0.036(2) 0.023(2) 0.0213(19) 0.0097(17) 0.0006(16) 0.0058(18) N2 0.0253(16) 0.0181(16) 0.0238(16) 0.0028(13) 0.0080(13) 0.0010(14) N3 0.0154(14) 0.0177(16) 0.0224(15) 0.0015(13) 0.0038(11) -0.0028(12) C3 0.031(2) 0.0163(19) 0.0229(18) -0.0018(15) 0.0114(16) -0.0047(16) C4 0.029(2) 0.020(2) 0.0218(19) 0.0004(16) 0.0094(16) 0.0056(17) N4 0.0183(15) 0.0206(17) 0.0184(15) -0.0024(13) 0.0054(11) -0.0029(13) P1 0.0094(4) 0.0151(5) 0.0179(4) -0.0014(4) 0.0026(3) 0.0004(3) O3 0.0128(12) 0.0129(12) 0.0188(12) 0.0024(10) 0.0014(9) -0.0003(10) O4 0.0105(11) 0.0252(14) 0.0128(12) 0.0011(10) 0.0001(9) 0.0033(11) O5 0.0147(12) 0.0182(14) 0.0321(14) -0.0022(12) 0.0040(10) -0.0008(11) O6 0.0165(13) 0.0177(13) 0.0193(13) 0.0006(10) 0.0056(10) 0.0038(10) C10 0.0121(16) 0.0141(17) 0.0148(16) 0.0047(14) -0.0010(13) 0.0031(14) C11 0.0154(17) 0.026(2) 0.0156(17) 0.0001(15) 0.0015(13) 0.0026(15) C12 0.0224(18) 0.021(2) 0.0123(16) -0.0037(14) 0.0013(13) 0.0044(15) C13 0.0151(16) 0.0178(18) 0.0173(16) -0.0018(15) 0.0002(13) 0.0028(15) C14 0.0205(19) 0.018(2) 0.0238(19) -0.0072(15) -0.0029(15) 0.0047(15) C15 0.0243(19) 0.0116(17) 0.034(2) -0.0010(16) 0.0006(16) -0.0039(15) C16 0.0231(19) 0.0172(19) 0.030(2) 0.0021(17) 0.0077(15) -0.0025(16) C17 0.0163(16) 0.0141(18) 0.0207(17) -0.0002(14) 0.0053(13) 0.0003(14) C18 0.0127(15) 0.0137(18) 0.0139(16) -0.0003(13) 0.0002(12) 0.0036(13) C19 0.0096(14) 0.0167(18) 0.0110(15) 0.0002(13) 0.0009(12) 0.0021(13) C20 0.0125(16) 0.0138(17) 0.0181(17) -0.0002(14) 0.0046(13) 0.0005(13) C21 0.0170(16) 0.019(2) 0.0157(16) -0.0061(14) 0.0017(13) -0.0024(15) C22 0.0242(18) 0.0170(19) 0.0186(17) -0.0054(14) 0.0066(14) -0.0022(15) C23 0.0204(17) 0.0137(17) 0.0175(17) -0.0004(15) 0.0087(14) -0.0024(15) C24 0.0223(18) 0.021(2) 0.026(2) 0.0011(16) 0.0121(15) 0.0031(16) C25 0.0184(17) 0.023(2) 0.029(2) 0.0018(17) 0.0092(15) 0.0057(17) C26 0.0139(17) 0.021(2) 0.027(2) 0.0057(17) 0.0024(15) 0.0005(15) C27 0.0173(17) 0.0133(17) 0.0189(17) 0.0000(14) 0.0025(13) -0.0004(14) C28 0.0112(15) 0.0111(16) 0.0207(17) 0.0014(14) 0.0060(13) -0.0023(13) C29 0.0115(15) 0.0114(16) 0.0175(17) -0.0005(14) 0.0033(13) -0.0015(13) P2 0.0098(4) 0.0132(4) 0.0212(5) 0.0011(4) 0.0038(3) 0.0005(3) O7 0.0110(11) 0.0189(13) 0.0192(13) 0.0002(11) 0.0036(9) 0.0022(10) O8 0.0119(11) 0.0156(13) 0.0186(12) 0.0028(10) 0.0050(9) -0.0013(10) O9 0.0138(12) 0.0150(13) 0.0297(14) 0.0011(11) 0.0062(10) 0.0036(10) O10 0.0151(12) 0.0166(13) 0.0343(15) -0.0021(12) 0.0036(10) -0.0046(11) C30 0.0091(15) 0.0158(17) 0.0163(16) 0.0008(14) 0.0035(12) 0.0018(13) C31 0.0169(16) 0.021(2) 0.0144(16) -0.0019(14) 0.0030(12) -0.0048(15) C32 0.0220(18) 0.017(2) 0.0200(18) -0.0053(14) 0.0071(14) -0.0025(15) C33 0.0161(16) 0.0139(18) 0.0175(17) -0.0007(14) 0.0060(13) -0.0012(14) C34 0.023(2) 0.0154(19) 0.028(2) -0.0023(16) 0.0128(16) 0.0017(16) C35 0.0153(17) 0.024(2) 0.033(2) 0.0011(18) 0.0122(15) 0.0049(16) C36 0.0123(16) 0.022(2) 0.0272(19) 0.0055(16) 0.0023(14) -0.0005(15) C37 0.0131(16) 0.0167(18) 0.0183(17) 0.0007(14) 0.0037(13) -0.0012(14) C38 0.0150(16) 0.0095(16) 0.0182(17) -0.0005(14) 0.0073(13) -0.0014(13) C39 0.0108(15) 0.0133(16) 0.0137(16) -0.0007(13) 0.0044(12) -0.0016(13) C40 0.0113(15) 0.0145(17) 0.0134(15) 0.0005(14) 0.0017(12) -0.0005(13) C41 0.0183(17) 0.0224(19) 0.0157(16) 0.0000(15) 0.0095(13) 0.0028(15) C42 0.0225(18) 0.025(2) 0.0132(16) -0.0053(15) 0.0043(13) 0.0043(16) C43 0.0201(17) 0.0134(17) 0.0146(16) 0.0002(14) 0.0011(13) 0.0027(14) C44 0.0178(17) 0.0193(19) 0.0221(18) -0.0044(15) -0.0023(14) -0.0003(15) C45 0.0218(19) 0.0138(18) 0.031(2) -0.0036(16) 0.0023(15) -0.0008(15) C46 0.0177(17) 0.0182(19) 0.027(2) -0.0006(16) 0.0043(14) -0.0026(16) C47 0.0149(16) 0.0186(19) 0.0200(17) 0.0011(15) 0.0044(13) -0.0001(15) C48 0.0113(15) 0.0145(18) 0.0145(16) -0.0007(13) 0.0011(12) 0.0008(13) C49 0.0108(15) 0.0124(16) 0.0139(15) -0.0014(13) 0.0003(12) 0.0024(13) O11 0.0157(12) 0.0186(13) 0.0462(18) -0.0076(13) 0.0001(11) -0.0004(11) O12 0.0237(13) 0.0207(14) 0.0266(14) 0.0028(12) 0.0056(11) -0.0001(11) O13 0.0242(14) 0.0158(14) 0.0354(16) -0.0040(12) -0.0006(12) 0.0034(11) C5 0.029(2) 0.032(2) 0.028(2) 0.0006(18) -0.0033(17) 0.0061(19) O14 0.0293(16) 0.0195(15) 0.0335(16) -0.0027(13) 0.0042(12) 0.0015(13) C6 0.032(2) 0.028(2) 0.033(2) 0.0017(19) 0.0012(18) 0.0062(19) _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 Ni N3 2.087(3) . ? Ni N4 2.098(3) . ? Ni N1 2.105(3) . ? Ni N2 2.111(3) . ? Ni O1 2.111(3) . ? Ni O2 2.145(3) . ? O1 H1C 0.7438 . ? O1 H1D 0.7229 . ? O2 H2C 0.7907 . ? O2 H2D 1.0110 . ? N1 C1 1.489(5) . ? N1 H1E 0.9200 . ? N1 H1F 0.9200 . ? C1 C2 1.507(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N2 1.480(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? N2 H2E 0.9200 . ? N2 H2F 0.9200 . ? N3 C3 1.477(5) . ? N3 H3C 0.9200 . ? N3 H3D 0.9200 . ? C3 C4 1.523(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N4 1.469(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? N4 H4C 0.9200 . ? N4 H4D 0.9200 . ? P1 O5 1.487(3) . ? P1 O6 1.494(3) . ? P1 O3 1.612(3) . ? P1 O4 1.619(3) . ? O3 C10 1.404(4) . ? O4 C20 1.392(4) . ? C10 C19 1.380(5) . ? C10 C11 1.403(5) . ? C11 C12 1.360(6) . ? C11 H11 0.9500 . ? C12 C13 1.423(5) . ? C12 H12 0.9500 . ? C13 C14 1.418(6) . ? C13 C18 1.430(5) . ? C14 C15 1.358(6) . ? C14 H14 0.9500 . ? C15 C16 1.418(6) . ? C15 H15 0.9500 . ? C16 C17 1.374(5) . ? C16 H16 0.9500 . ? C17 C18 1.417(5) . ? C17 H17 0.9500 . ? C18 C19 1.437(5) . ? C19 C29 1.495(5) . ? C20 C29 1.377(5) . ? C20 C21 1.414(5) . ? C21 C22 1.368(5) . ? C21 H21 0.9500 . ? C22 C23 1.421(5) . ? C22 H22 0.9500 . ? C23 C24 1.415(5) . ? C23 C28 1.434(5) . ? C24 C25 1.374(6) . ? C24 H24 0.9500 . ? C25 C26 1.417(6) . ? C25 H25 0.9500 . ? C26 C27 1.365(5) . ? C26 H26 0.9500 . ? C27 C28 1.417(5) . ? C27 H27 0.9500 . ? C28 C29 1.444(5) . ? P2 O10 1.481(3) . ? P2 O9 1.482(3) . ? P2 O8 1.617(3) . ? P2 O7 1.617(3) . ? O7 C30 1.388(4) . ? O8 C40 1.402(4) . ? C30 C39 1.387(5) . ? C30 C31 1.400(5) . ? C31 C32 1.364(5) . ? C31 H31 0.9500 . ? C32 C33 1.419(5) . ? C32 H32 0.9500 . ? C33 C38 1.418(5) . ? C33 C34 1.422(5) . ? C34 C35 1.371(6) . ? C34 H34 0.9500 . ? C35 C36 1.408(6) . ? C35 H35 0.9500 . ? C36 C37 1.379(5) . ? C36 H36 0.9500 . ? C37 C38 1.418(5) . ? C37 H37 0.9500 . ? C38 C39 1.439(5) . ? C39 C49 1.484(5) . ? C40 C49 1.376(5) . ? C40 C41 1.409(5) . ? C41 C42 1.356(6) . ? C41 H41 0.9500 . ? C42 C43 1.416(5) . ? C42 H42 0.9500 . ? C43 C48 1.426(5) . ? C43 C44 1.433(5) . ? C44 C45 1.362(6) . ? C44 H44 0.9500 . ? C45 C46 1.408(5) . ? C45 H45 0.9500 . ? C46 C47 1.375(5) . ? C46 H46 0.9500 . ? C47 C48 1.414(5) . ? C47 H47 0.9500 . ? C48 C49 1.442(5) . ? O11 H11A 0.7812 . ? O11 H11B 0.8366 . ? O12 H12A 1.0002 . ? O12 H12B 0.8832 . ? O13 C5 1.421(5) . ? O13 H13A 0.8400 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? O14 C6 1.415(5) . ? O14 H14A 0.8400 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? 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 N3 Ni N4 83.18(12) . . ? N3 Ni N1 93.07(13) . . ? N4 Ni N1 100.64(13) . . ? N3 Ni N2 174.28(13) . . ? N4 Ni N2 93.46(13) . . ? N1 Ni N2 82.97(13) . . ? N3 Ni O1 89.49(11) . . ? N4 Ni O1 85.91(12) . . ? N1 Ni O1 173.20(13) . . ? N2 Ni O1 94.90(12) . . ? N3 Ni O2 93.95(11) . . ? N4 Ni O2 169.99(12) . . ? N1 Ni O2 89.07(12) . . ? N2 Ni O2 90.12(11) . . ? O1 Ni O2 84.47(11) . . ? Ni O1 H1C 113.5 . . ? Ni O1 H1D 111.3 . . ? H1C O1 H1D 113.8 . . ? Ni O2 H2C 117.9 . . ? Ni O2 H2D 118.1 . . ? H2C O2 H2D 107.1 . . ? C1 N1 Ni 107.1(2) . . ? C1 N1 H1E 110.3 . . ? Ni N1 H1E 110.3 . . ? C1 N1 H1F 110.3 . . ? Ni N1 H1F 110.3 . . ? H1E N1 H1F 108.5 . . ? N1 C1 C2 107.9(3) . . ? N1 C1 H1A 110.1 . . ? C2 C1 H1A 110.1 . . ? N1 C1 H1B 110.1 . . ? C2 C1 H1B 110.1 . . ? H1A C1 H1B 108.4 . . ? N2 C2 C1 109.7(3) . . ? N2 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N2 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 N2 Ni 107.6(3) . . ? C2 N2 H2E 110.2 . . ? Ni N2 H2E 110.2 . . ? C2 N2 H2F 110.2 . . ? Ni N2 H2F 110.2 . . ? H2E N2 H2F 108.5 . . ? C3 N3 Ni 108.3(2) . . ? C3 N3 H3C 110.0 . . ? Ni N3 H3C 110.0 . . ? C3 N3 H3D 110.0 . . ? Ni N3 H3D 110.0 . . ? H3C N3 H3D 108.4 . . ? N3 C3 C4 109.1(3) . . ? N3 C3 H3A 109.9 . . ? C4 C3 H3A 109.9 . . ? N3 C3 H3B 109.9 . . ? C4 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N4 C4 C3 108.3(3) . . ? N4 C4 H4A 110.0 . . ? C3 C4 H4A 110.0 . . ? N4 C4 H4B 110.0 . . ? C3 C4 H4B 110.0 . . ? H4A C4 H4B 108.4 . . ? C4 N4 Ni 107.6(2) . . ? C4 N4 H4C 110.2 . . ? Ni N4 H4C 110.2 . . ? C4 N4 H4D 110.2 . . ? Ni N4 H4D 110.2 . . ? H4C N4 H4D 108.5 . . ? O5 P1 O6 118.13(15) . . ? O5 P1 O3 106.68(15) . . ? O6 P1 O3 111.54(14) . . ? O5 P1 O4 112.07(15) . . ? O6 P1 O4 105.26(14) . . ? O3 P1 O4 102.06(13) . . ? C10 O3 P1 115.0(2) . . ? C20 O4 P1 121.1(2) . . ? C19 C10 C11 123.6(3) . . ? C19 C10 O3 119.0(3) . . ? C11 C10 O3 117.4(3) . . ? C12 C11 C10 119.2(3) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C13 120.9(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 121.7(3) . . ? C14 C13 C18 118.9(3) . . ? C12 C13 C18 119.4(3) . . ? C15 C14 C13 121.9(4) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 119.3(4) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 121.2(3) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C17 C18 C13 118.1(3) . . ? C17 C18 C19 122.6(3) . . ? C13 C18 C19 119.2(3) . . ? C10 C19 C18 117.4(3) . . ? C10 C19 C29 119.5(3) . . ? C18 C19 C29 123.0(3) . . ? C29 C20 O4 119.7(3) . . ? C29 C20 C21 123.2(3) . . ? O4 C20 C21 117.0(3) . . ? C22 C21 C20 118.9(3) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 121.1(3) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 121.2(3) . . ? C24 C23 C28 119.1(3) . . ? C22 C23 C28 119.7(3) . . ? C25 C24 C23 120.9(4) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 120.1(4) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C27 C26 C25 120.2(4) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 121.5(4) . . ? C26 C27 H27 119.3 . . ? C28 C27 H27 119.3 . . ? C27 C28 C23 118.2(3) . . ? C27 C28 C29 123.1(3) . . ? C23 C28 C29 118.6(3) . . ? C20 C29 C28 118.2(3) . . ? C20 C29 C19 119.7(3) . . ? C28 C29 C19 121.9(3) . . ? O10 P2 O9 119.28(16) . . ? O10 P2 O8 106.73(15) . . ? O9 P2 O8 111.08(15) . . ? O10 P2 O7 111.63(15) . . ? O9 P2 O7 105.11(14) . . ? O8 P2 O7 101.66(13) . . ? C30 O7 P2 121.0(2) . . ? C40 O8 P2 115.5(2) . . ? C39 C30 O7 119.4(3) . . ? C39 C30 C31 123.0(3) . . ? O7 C30 C31 117.6(3) . . ? C32 C31 C30 119.6(3) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C31 C32 C33 120.5(3) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C38 C33 C32 119.9(3) . . ? C38 C33 C34 119.4(3) . . ? C32 C33 C34 120.7(3) . . ? C35 C34 C33 120.8(4) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C34 C35 C36 119.9(3) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C37 C36 C35 120.5(3) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C36 C37 C38 120.8(3) . . ? C36 C37 H37 119.6 . . ? C38 C37 H37 119.6 . . ? C37 C38 C33 118.5(3) . . ? C37 C38 C39 122.2(3) . . ? C33 C38 C39 119.3(3) . . ? C30 C39 C38 117.5(3) . . ? C30 C39 C49 119.9(3) . . ? C38 C39 C49 122.5(3) . . ? C49 C40 O8 118.8(3) . . ? C49 C40 C41 123.8(3) . . ? O8 C40 C41 117.4(3) . . ? C42 C41 C40 119.0(3) . . ? C42 C41 H41 120.5 . . ? C40 C41 H41 120.5 . . ? C41 C42 C43 120.8(3) . . ? C41 C42 H42 119.6 . . ? C43 C42 H42 119.6 . . ? C42 C43 C48 119.9(3) . . ? C42 C43 C44 121.0(3) . . ? C48 C43 C44 119.0(3) . . ? C45 C44 C43 120.6(4) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C44 C45 C46 120.3(4) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C47 C46 C45 120.6(3) . . ? C47 C46 H46 119.7 . . ? C45 C46 H46 119.7 . . ? C46 C47 C48 120.9(3) . . ? C46 C47 H47 119.5 . . ? C48 C47 H47 119.5 . . ? C47 C48 C43 118.5(3) . . ? C47 C48 C49 122.4(3) . . ? C43 C48 C49 119.0(3) . . ? C40 C49 C48 117.2(3) . . ? C40 C49 C39 119.5(3) . . ? C48 C49 C39 123.4(3) . . ? H11A O11 H11B 117.6 . . ? H12A O12 H12B 111.6 . . ? C5 O13 H13A 109.5 . . ? O13 C5 H5A 109.5 . . ? O13 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O13 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C6 O14 H14A 109.5 . . ? O14 C6 H6A 109.5 . . ? O14 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O14 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 O1 H1C O13 0.74 1.93 2.653(4) 162.3 . O1 H1D O6 0.72 2.11 2.815(4) 164.3 . O2 H2C O11 0.79 1.96 2.733(4) 164.3 . O2 H2D O12 1.01 1.64 2.655(4) 178.9 4_464 N1 H1E O12 0.92 2.11 2.985(5) 158.4 3_444 N1 H1F O9 0.92 2.34 3.134(4) 144.8 4_454 N2 H2E O11 0.92 2.28 3.116(4) 151.4 . N2 H2F O6 0.92 2.38 3.177(4) 145.4 2_564 N3 H3C O6 0.92 2.15 3.038(4) 163.0 . N3 H3D O9 0.92 1.98 2.883(4) 167.5 4_454 N4 H4C O2 0.92 2.18 3.049(4) 157.5 2_564 N4 H4D O6 0.92 2.33 2.993(4) 128.2 2_564 O11 H11A O10 0.78 2.08 2.828(4) 161.6 4_464 O11 H11B O5 0.84 2.04 2.780(4) 146.9 1_565 O12 H12A O14 1.00 1.66 2.648(4) 168.1 . O12 H12B O9 0.88 1.86 2.690(4) 155.6 1_565 O13 H13A O5 0.84 1.82 2.655(4) 172.7 1_565 O14 H14A O10 0.84 1.86 2.688(4) 168.1 . _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.70 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.564 _refine_diff_density_min -0.770 _refine_diff_density_rms 0.088 # Attachment '6_Ni-en2-203K.CIF' data_thomrm _database_code_depnum_ccdc_archive 'CCDC 286360' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (cis-diaqua-bis(ethylene diamine)-nickel(II))-bis(rac-1,1'- binaphthalene-2,2'-diylphosphate).dihydrate.dimethanol ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H56 N4 Ni O14 P2' _chemical_formula_weight 1009.60 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' Ni Ni 0.3393 1.1124 '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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 42.599(8) _cell_length_b 9.0906(18) _cell_length_c 12.432(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.762(4) _cell_angle_gamma 90.00 _cell_volume 4758.1(16) _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 plate _exptl_crystal_colour violet _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2120 _exptl_absorpt_coefficient_mu 0.545 _exptl_absorpt_correction_type Mulit-scan _exptl_absorpt_correction_T_min 0.8053 _exptl_absorpt_correction_T_max 0.9801 _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 17756 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.1327 _diffrn_reflns_limit_h_min -51 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 0.97 _diffrn_reflns_theta_max 25.60 _reflns_number_total 8847 _reflns_number_gt 5040 _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 hydrogen atoms of the aqua ligands and the water of crystallization were initially found but had to be fixed upon further refinement with Ueq(H) = 1.5 Ueq(O). The hydrogen atoms of the ethylene diamine ligands were calculated as an idealized C/NH2 groups with tetrahedral angles (AFIX 23) and Ueq(H) = 1.2 Ueq(C/N). The methanolic O-H were placed at calculated positions as an idealized OH-group with C-O-H angle tetrahedral and formation of the best hydrogen bond to a neighboring acceptor (AFIX 83) with Ueq(H) = 1.5 Ueq(O). Hydrogen atoms on C (binaphthyl) were calculated with an appropriate riding model (AFIX 43) and Ueq(H) = 1.2 Ueq(C), the ones on C (methanol) as an idealized CH3 group (AFIX 133) and Ueq(H) = 1.5 Ueq(C). The structure was solved and refined in the non-centrosymmetric polar space group Cc with racemic twinning (twin law 1 0 0 0 1 0 0 0 1 and BASF 0.47895. Structure solution and refinement was also carried out in the centrosymmetric space group C2/c. However, the Ni(en)2(H2O)2 fragment was then found crystallographically disordered due to the two-fold rotation axis in the vicinity of the nickel atom. The disorder could be fully resolved, yet, refinement did not progress below R1 = 0.1419 for 3073 data with Fo > 4sig(Fo) and R1 = 0.2105 and wR2 = 0.3554 for all 5786 data. The data set was also measured at T = 100(2) K on an Enraf-Nonius Kappa CCD diffractometer with a similar result in terms of refinements in Cc anc C2/c as stated above. ; _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^+7.9830P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(4) _refine_ls_number_reflns 8847 _refine_ls_number_parameters 605 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1201 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.001 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 Ni Ni 0.80304(2) 0.53806(9) 0.08115(7) 0.0275(2) Uani 1 1 d . . . O1 O 0.84908(12) 0.5386(6) 0.1708(4) 0.0335(14) Uani 1 1 d . . . H1C H 0.8536 0.6072 0.2003 0.050 Uiso 1 1 d . . . H1D H 0.8514 0.4729 0.2087 0.050 Uiso 1 1 d . . . O2 O 0.78843(13) 0.6263(4) 0.2279(4) 0.0291(10) Uani 1 1 d . . . H2C H 0.7910 0.7111 0.2375 0.044 Uiso 1 1 d . . . H2D H 0.7674 0.5973 0.2454 0.044 Uiso 1 1 d . . . N1 N 0.75611(13) 0.5587(7) 0.0037(4) 0.0289(17) Uani 1 1 d . . . H1E H 0.7534 0.5079 -0.0601 0.035 Uiso 1 1 calc R . . H1F H 0.7426 0.5214 0.0468 0.035 Uiso 1 1 calc R . . C1 C 0.74938(18) 0.7191(9) -0.0175(6) 0.042(2) Uani 1 1 d . . . H1A H 0.7296 0.7320 -0.0683 0.050 Uiso 1 1 calc R . . H1B H 0.7474 0.7705 0.0505 0.050 Uiso 1 1 calc R . . C2 C 0.77629(18) 0.7756(9) -0.0642(6) 0.044(2) Uani 1 1 d . . . H2A H 0.7734 0.8806 -0.0803 0.053 Uiso 1 1 calc R . . H2B H 0.7780 0.7238 -0.1322 0.053 Uiso 1 1 calc R . . N2 N 0.80667(14) 0.7515(6) 0.0188(4) 0.0439(17) Uani 1 1 d . . . H2E H 0.8080 0.8193 0.0731 0.053 Uiso 1 1 calc R . . H2F H 0.8242 0.7593 -0.0143 0.053 Uiso 1 1 calc R . . N3 N 0.79642(13) 0.3174(6) 0.1274(4) 0.0347(15) Uani 1 1 d . . . H3C H 0.8100 0.2949 0.1890 0.042 Uiso 1 1 calc R . . H3D H 0.7762 0.3036 0.1404 0.042 Uiso 1 1 calc R . . C3 C 0.8030(2) 0.2204(8) 0.0337(6) 0.044(2) Uani 1 1 d . . . H3A H 0.7843 0.2169 -0.0230 0.053 Uiso 1 1 calc R . . H3B H 0.8080 0.1200 0.0595 0.053 Uiso 1 1 calc R . . C4 C 0.83194(18) 0.2884(8) -0.0130(6) 0.035(2) Uani 1 1 d . . . H4A H 0.8510 0.2845 0.0419 0.042 Uiso 1 1 calc R . . H4B H 0.8360 0.2330 -0.0771 0.042 Uiso 1 1 calc R . . N4 N 0.82402(12) 0.4409(7) -0.0426(4) 0.0285(15) Uani 1 1 d . . . H4C H 0.8104 0.4439 -0.1064 0.034 Uiso 1 1 calc R . . H4D H 0.8419 0.4910 -0.0517 0.034 Uiso 1 1 calc R . . P1 P 0.86704(4) 0.1806(2) 0.31759(15) 0.0238(5) Uani 1 1 d . . . O3 O 0.89397(11) 0.1584(5) 0.4230(3) 0.0224(12) Uani 1 1 d . . . O4 O 0.88845(10) 0.2210(5) 0.2241(3) 0.0229(12) Uani 1 1 d . . . O5 O 0.85088(9) 0.0359(6) 0.2974(4) 0.0336(12) Uani 1 1 d . . . O6 O 0.84728(10) 0.3108(5) 0.3295(3) 0.0279(12) Uani 1 1 d . . . C10 C 0.91436(18) 0.2786(8) 0.4468(6) 0.0231(19) Uani 1 1 d . . . C11 C 0.90969(17) 0.3677(9) 0.5381(6) 0.033(2) Uani 1 1 d . . . H11 H 0.8939 0.3445 0.5806 0.039 Uiso 1 1 calc R . . C12 C 0.92868(16) 0.4860(8) 0.5612(5) 0.0285(19) Uani 1 1 d . . . H12 H 0.9259 0.5455 0.6209 0.034 Uiso 1 1 calc R . . C13 C 0.95222(15) 0.5229(8) 0.4993(5) 0.0251(17) Uani 1 1 d . . . C14 C 0.97068(17) 0.6533(8) 0.5168(6) 0.033(2) Uani 1 1 d . . . H14 H 0.9681 0.7122 0.5770 0.039 Uiso 1 1 calc R . . C15 C 0.99160(18) 0.6978(9) 0.4523(6) 0.039(2) Uani 1 1 d . . . H15 H 1.0026 0.7870 0.4664 0.047 Uiso 1 1 calc R . . C16 C 0.99682(18) 0.6091(8) 0.3630(6) 0.037(2) Uani 1 1 d . . . H16 H 1.0118 0.6368 0.3186 0.044 Uiso 1 1 calc R . . C17 C 0.97969(15) 0.4827(8) 0.3428(5) 0.0260(18) Uani 1 1 d . . . H17 H 0.9826 0.4260 0.2819 0.031 Uiso 1 1 calc R . . C18 C 0.95761(14) 0.4328(7) 0.4098(5) 0.0191(16) Uani 1 1 d . . . C19 C 0.93839(16) 0.3002(7) 0.3873(5) 0.0193(17) Uani 1 1 d . . . C20 C 0.91802(16) 0.1569(7) 0.2221(5) 0.0196(16) Uani 1 1 d . . . C21 C 0.92056(16) 0.0581(9) 0.1363(6) 0.0266(18) Uani 1 1 d . . . H21 H 0.9028 0.0368 0.0837 0.032 Uiso 1 1 calc R . . C22 C 0.94882(16) -0.0048(7) 0.1313(5) 0.029(2) Uani 1 1 d . . . H22 H 0.9506 -0.0704 0.0741 0.035 Uiso 1 1 calc R . . C23 C 0.97603(15) 0.0242(8) 0.2094(5) 0.0220(16) Uani 1 1 d . . . C24 C 1.00532(16) -0.0465(10) 0.2084(6) 0.0340(19) Uani 1 1 d . . . H24 H 1.0076 -0.1105 0.1506 0.041 Uiso 1 1 calc R . . C25 C 1.03069(16) -0.0252(9) 0.2888(6) 0.0341(19) Uani 1 1 d . . . H25 H 1.0500 -0.0741 0.2864 0.041 Uiso 1 1 calc R . . C26 C 1.02749(18) 0.0698(9) 0.3742(6) 0.031(2) Uani 1 1 d . . . H26 H 1.0450 0.0854 0.4290 0.037 Uiso 1 1 calc R . . C27 C 0.99986(17) 0.1403(7) 0.3804(5) 0.0232(17) Uani 1 1 d . . . H27 H 0.9982 0.2011 0.4405 0.028 Uiso 1 1 calc R . . C28 C 0.97345(16) 0.1235(7) 0.2975(5) 0.0182(16) Uani 1 1 d . . . C29 C 0.94291(17) 0.1938(7) 0.2985(6) 0.0216(17) Uani 1 1 d . . . P2 P 1.21148(4) 0.3212(2) 0.66077(14) 0.0254(5) Uani 1 1 d . . . O7 O 1.18971(10) 0.2789(5) 0.7510(4) 0.0236(12) Uani 1 1 d . . . O8 O 1.18512(11) 0.3463(5) 0.5531(4) 0.0244(12) Uani 1 1 d . . . O9 O 1.23080(10) 0.1879(5) 0.6498(4) 0.0273(12) Uani 1 1 d . . . O10 O 1.22793(9) 0.4635(6) 0.6841(4) 0.0335(12) Uani 1 1 d . . . C30 C 1.16028(16) 0.3454(7) 0.7509(5) 0.0232(17) Uani 1 1 d . . . C31 C 1.15664(17) 0.4411(8) 0.8372(5) 0.0273(18) Uani 1 1 d . . . H31 H 1.1740 0.4603 0.8918 0.033 Uiso 1 1 calc R . . C32 C 1.12847(17) 0.5047(8) 0.8414(6) 0.032(2) Uani 1 1 d . . . H32 H 1.1260 0.5672 0.8998 0.039 Uiso 1 1 calc R . . C33 C 1.10204(17) 0.4784(8) 0.7576(5) 0.0255(17) Uani 1 1 d . . . C34 C 1.07251(17) 0.5516(9) 0.7597(6) 0.030(2) Uani 1 1 d . . . H34 H 1.0701 0.6147 0.8178 0.036 Uiso 1 1 calc R . . C35 C 1.04814(17) 0.5307(9) 0.6793(6) 0.038(2) Uani 1 1 d . . . H35 H 1.0289 0.5802 0.6815 0.045 Uiso 1 1 calc R . . C36 C 1.05088(17) 0.4355(9) 0.5908(6) 0.036(2) Uani 1 1 d . . . H36 H 1.0337 0.4220 0.5344 0.043 Uiso 1 1 calc R . . C37 C 1.07936(16) 0.3628(8) 0.5892(6) 0.0267(19) Uani 1 1 d . . . H37 H 1.0814 0.2990 0.5311 0.032 Uiso 1 1 calc R . . C38 C 1.10526(16) 0.3818(7) 0.6718(5) 0.0194(17) Uani 1 1 d . . . C39 C 1.13516(15) 0.3069(7) 0.6697(5) 0.0180(16) Uani 1 1 d . . . C40 C 1.16466(16) 0.2271(8) 0.5241(5) 0.0196(17) Uani 1 1 d . . . C41 C 1.17005(17) 0.1426(8) 0.4379(5) 0.0279(19) Uani 1 1 d . . . H41 H 1.1869 0.1652 0.4001 0.034 Uiso 1 1 calc R . . C42 C 1.15090(16) 0.0254(9) 0.4069(5) 0.0315(18) Uani 1 1 d . . . H42 H 1.1538 -0.0288 0.3448 0.038 Uiso 1 1 calc R . . C43 C 1.12687(16) -0.0154(8) 0.4666(5) 0.0274(18) Uani 1 1 d . . . C44 C 1.10881(17) -0.1471(8) 0.4425(6) 0.0325(19) Uani 1 1 d . . . H44 H 1.1119 -0.2048 0.3822 0.039 Uiso 1 1 calc R . . C45 C 1.08725(18) -0.1890(8) 0.5064(6) 0.038(2) Uani 1 1 d . . . H45 H 1.0751 -0.2743 0.4890 0.045 Uiso 1 1 calc R . . C46 C 1.08305(16) -0.1057(8) 0.5984(6) 0.0307(19) Uani 1 1 d . . . H46 H 1.0690 -0.1390 0.6444 0.037 Uiso 1 1 calc R . . C47 C 1.09936(15) 0.0245(9) 0.6220(6) 0.0275(17) Uani 1 1 d . . . H47 H 1.0953 0.0809 0.6818 0.033 Uiso 1 1 calc R . . C48 C 1.12180(15) 0.0742(7) 0.5587(5) 0.0216(17) Uani 1 1 d . . . C49 C 1.14027(15) 0.2030(7) 0.5840(5) 0.0176(16) Uani 1 1 d . . . O11 O 0.79017(12) 0.9271(4) 0.2249(5) 0.0475(13) Uani 1 1 d . . . H11A H 0.7749 0.9701 0.2026 0.071 Uiso 1 1 d . . . H11B H 0.8046 0.9661 0.2659 0.071 Uiso 1 1 d . . . O12 O 1.23311(10) 0.9497(6) 0.7810(3) 0.0368(13) Uani 1 1 d . . . H12A H 1.2184 0.8596 0.7642 0.055 Uiso 1 1 d . . . H12B H 1.2260 1.0200 0.7318 0.055 Uiso 1 1 d . . . O13 O 0.87718(12) 0.7834(5) 0.2519(4) 0.0425(15) Uani 1 1 d . . . H13A H 0.8657 0.8443 0.2767 0.064 Uiso 1 1 calc R . . C5 C 0.90465(19) 0.7619(10) 0.3261(6) 0.053(3) Uani 1 1 d . . . H5A H 0.9184 0.8470 0.3260 0.079 Uiso 1 1 calc R . . H5B H 0.9157 0.6752 0.3058 0.079 Uiso 1 1 calc R . . H5C H 0.8991 0.7484 0.3983 0.079 Uiso 1 1 calc R . . O14 O 1.19824(14) 0.7178(6) 0.7158(5) 0.0491(17) Uani 1 1 d . . . H14A H 1.2053 0.6329 0.7138 0.074 Uiso 1 1 calc R . . C6 C 1.1699(2) 0.7323(10) 0.6364(7) 0.058(3) Uani 1 1 d . . . H6A H 1.1544 0.7910 0.6668 0.087 Uiso 1 1 calc R . . H6B H 1.1612 0.6356 0.6175 0.087 Uiso 1 1 calc R . . H6C H 1.1752 0.7801 0.5717 0.087 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 Ni 0.0295(5) 0.0275(5) 0.0254(5) 0.0018(5) 0.0039(4) -0.0002(5) O1 0.035(3) 0.021(3) 0.042(3) 0.004(3) 0.000(3) -0.004(3) O2 0.032(2) 0.025(2) 0.030(3) -0.004(3) 0.0033(19) -0.003(3) N1 0.026(4) 0.035(4) 0.025(4) 0.003(3) 0.001(3) -0.002(3) C1 0.037(5) 0.045(6) 0.039(5) -0.001(4) -0.010(4) 0.008(4) C2 0.042(5) 0.052(6) 0.036(5) 0.023(4) -0.002(4) 0.009(5) N2 0.052(4) 0.035(4) 0.046(4) -0.001(3) 0.014(3) -0.002(3) N3 0.041(4) 0.039(4) 0.026(3) 0.018(3) 0.009(3) -0.008(3) C3 0.074(6) 0.019(4) 0.041(5) -0.007(4) 0.017(5) -0.001(5) C4 0.049(5) 0.036(5) 0.023(4) 0.003(4) 0.017(4) 0.012(4) N4 0.023(3) 0.037(4) 0.027(3) 0.007(3) 0.006(3) 0.002(3) P1 0.0175(11) 0.0231(12) 0.0304(12) 0.0000(9) 0.0021(9) 0.0012(9) O3 0.023(3) 0.021(3) 0.022(3) 0.005(2) -0.003(2) 0.001(2) O4 0.020(3) 0.032(3) 0.016(3) 0.001(2) -0.001(2) 0.007(2) O5 0.025(3) 0.020(3) 0.052(3) -0.002(3) -0.005(2) -0.001(3) O6 0.030(3) 0.031(3) 0.023(3) 0.002(2) 0.003(2) 0.009(2) C10 0.021(4) 0.029(5) 0.016(4) 0.003(4) -0.007(4) 0.008(4) C11 0.032(5) 0.044(5) 0.020(4) -0.007(4) -0.003(4) 0.013(4) C12 0.037(4) 0.036(5) 0.012(4) -0.011(3) 0.002(3) 0.012(4) C13 0.028(4) 0.026(5) 0.019(4) -0.003(3) -0.003(3) 0.005(4) C14 0.034(5) 0.029(5) 0.032(5) -0.013(4) -0.004(4) 0.003(4) C15 0.038(5) 0.028(5) 0.046(5) 0.007(4) -0.009(4) -0.004(4) C16 0.042(5) 0.028(5) 0.044(5) -0.006(4) 0.014(4) -0.001(4) C17 0.033(4) 0.021(4) 0.024(4) 0.002(3) 0.005(3) 0.007(4) C18 0.019(4) 0.021(4) 0.017(4) -0.004(3) 0.000(3) 0.007(3) C19 0.022(4) 0.020(4) 0.014(4) 0.005(3) -0.003(3) 0.004(3) C20 0.022(4) 0.017(4) 0.021(4) -0.005(3) 0.006(3) -0.002(3) C21 0.022(4) 0.029(5) 0.028(4) -0.006(4) 0.001(3) 0.000(4) C22 0.045(5) 0.023(5) 0.019(4) -0.005(3) 0.005(4) -0.003(4) C23 0.021(4) 0.021(4) 0.024(4) 0.007(4) 0.005(3) 0.008(4) C24 0.036(5) 0.040(5) 0.031(4) 0.004(4) 0.022(4) 0.011(5) C25 0.026(4) 0.038(5) 0.041(5) 0.012(5) 0.015(4) 0.011(4) C26 0.022(5) 0.037(6) 0.031(5) 0.004(4) -0.002(4) 0.005(4) C27 0.026(4) 0.021(4) 0.022(4) -0.001(3) 0.000(3) 0.001(4) C28 0.020(4) 0.012(4) 0.025(4) 0.001(3) 0.010(3) -0.002(3) C29 0.026(4) 0.012(4) 0.028(4) 0.003(3) 0.009(4) 0.003(3) P2 0.0209(11) 0.0228(12) 0.0324(12) 0.0017(10) 0.0036(9) 0.0020(10) O7 0.017(3) 0.025(3) 0.030(3) -0.004(2) 0.005(2) 0.001(2) O8 0.023(3) 0.026(3) 0.026(3) 0.002(2) 0.006(2) 0.001(3) O9 0.022(3) 0.021(3) 0.039(3) 0.005(2) 0.004(2) 0.008(2) O10 0.023(3) 0.023(3) 0.053(3) -0.003(3) -0.001(2) -0.006(3) C30 0.023(4) 0.019(4) 0.027(4) 0.008(3) 0.005(4) 0.004(3) C31 0.036(5) 0.026(5) 0.018(4) -0.010(4) 0.000(3) -0.011(4) C32 0.036(5) 0.025(6) 0.038(5) -0.009(4) 0.014(4) -0.007(4) C33 0.032(4) 0.016(4) 0.030(4) 0.000(4) 0.008(3) -0.005(4) C34 0.026(4) 0.024(5) 0.042(5) -0.002(4) 0.012(4) 0.007(4) C35 0.027(4) 0.028(5) 0.059(6) 0.004(5) 0.013(4) 0.011(4) C36 0.029(5) 0.033(5) 0.046(5) 0.012(4) 0.008(4) 0.000(4) C37 0.022(4) 0.022(4) 0.035(5) 0.004(4) 0.002(4) -0.006(4) C38 0.019(4) 0.016(4) 0.023(4) 0.006(3) 0.003(3) -0.003(3) C39 0.016(4) 0.019(4) 0.018(4) -0.001(3) 0.000(3) -0.007(3) C40 0.021(4) 0.024(4) 0.013(4) 0.001(3) -0.002(3) -0.002(3) C41 0.032(5) 0.036(5) 0.020(4) 0.005(4) 0.014(4) 0.003(4) C42 0.036(4) 0.040(5) 0.019(4) -0.003(4) 0.007(3) 0.015(4) C43 0.030(4) 0.029(5) 0.023(4) 0.001(4) 0.002(3) 0.009(4) C44 0.030(5) 0.030(5) 0.035(5) -0.006(4) -0.001(4) -0.002(4) C45 0.044(5) 0.022(5) 0.046(5) -0.012(4) 0.004(4) -0.004(4) C46 0.021(4) 0.031(5) 0.039(5) 0.006(4) 0.003(4) -0.005(4) C47 0.021(4) 0.026(4) 0.035(4) 0.001(4) 0.003(3) 0.003(4) C48 0.019(4) 0.026(5) 0.019(4) 0.005(3) 0.002(3) 0.006(3) C49 0.013(4) 0.020(4) 0.018(4) 0.001(3) -0.003(3) 0.003(3) O11 0.033(3) 0.027(3) 0.077(4) -0.013(3) -0.008(2) 0.006(3) O12 0.038(3) 0.038(3) 0.033(3) 0.007(3) -0.002(2) -0.006(3) O13 0.037(4) 0.030(3) 0.056(4) -0.012(3) -0.008(3) 0.007(3) C5 0.050(6) 0.066(7) 0.039(6) 0.005(5) -0.003(5) 0.015(5) O14 0.062(5) 0.032(4) 0.054(4) -0.002(3) 0.010(4) 0.000(3) C6 0.061(7) 0.045(6) 0.065(7) 0.013(5) -0.001(6) 0.020(5) _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 Ni N4 2.090(5) . ? Ni N1 2.091(6) . ? Ni N2 2.104(5) . ? Ni O1 2.103(5) . ? Ni N3 2.118(5) . ? Ni O2 2.169(5) . ? O1 H1C 0.7338 . ? O1 H1D 0.7571 . ? O2 H2C 0.7852 . ? O2 H2D 0.9904 . ? N1 C1 1.502(9) . ? N1 H1E 0.9100 . ? N1 H1F 0.9100 . ? C1 C2 1.455(9) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C2 N2 1.543(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? N2 H2E 0.9100 . ? N2 H2F 0.9100 . ? N3 C3 1.521(8) . ? N3 H3C 0.9100 . ? N3 H3D 0.9100 . ? C3 C4 1.567(10) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 N4 1.461(9) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? N4 H4C 0.9100 . ? N4 H4D 0.9100 . ? P1 O6 1.473(5) . ? P1 O5 1.488(5) . ? P1 O3 1.617(5) . ? P1 O4 1.625(5) . ? O3 C10 1.400(8) . ? O4 C20 1.391(7) . ? C10 C19 1.365(9) . ? C10 C11 1.433(9) . ? C11 C12 1.350(9) . ? C11 H11 0.9400 . ? C12 C13 1.395(8) . ? C12 H12 0.9400 . ? C13 C14 1.421(10) . ? C13 C18 1.428(8) . ? C14 C15 1.349(9) . ? C14 H14 0.9400 . ? C15 C16 1.416(10) . ? C15 H15 0.9400 . ? C16 C17 1.364(9) . ? C16 H16 0.9400 . ? C17 C18 1.422(8) . ? C17 H17 0.9400 . ? C18 C19 1.460(8) . ? C19 C29 1.502(9) . ? C20 C29 1.353(9) . ? C20 C21 1.411(9) . ? C21 C22 1.343(9) . ? C21 H21 0.9400 . ? C22 C23 1.419(8) . ? C22 H22 0.9400 . ? C23 C24 1.405(9) . ? C23 C28 1.436(9) . ? C24 C25 1.370(9) . ? C24 H24 0.9400 . ? C25 C26 1.391(10) . ? C25 H25 0.9400 . ? C26 C27 1.353(9) . ? C26 H26 0.9400 . ? C27 C28 1.413(9) . ? C27 H27 0.9400 . ? C28 C29 1.451(9) . ? P2 O10 1.479(5) . ? P2 O9 1.482(4) . ? P2 O7 1.607(5) . ? P2 O8 1.627(5) . ? O7 C30 1.392(7) . ? O8 C40 1.403(8) . ? C30 C39 1.399(9) . ? C30 C31 1.407(9) . ? C31 C32 1.341(9) . ? C31 H31 0.9400 . ? C32 C33 1.433(9) . ? C32 H32 0.9400 . ? C33 C38 1.404(9) . ? C33 C34 1.427(9) . ? C34 C35 1.341(10) . ? C34 H34 0.9400 . ? C35 C36 1.419(10) . ? C35 H35 0.9400 . ? C36 C37 1.384(9) . ? C36 H36 0.9400 . ? C37 C38 1.399(9) . ? C37 H37 0.9400 . ? C38 C39 1.448(9) . ? C39 C49 1.465(9) . ? C40 C41 1.366(9) . ? C40 C49 1.385(9) . ? C41 C42 1.361(9) . ? C41 H41 0.9400 . ? C42 C43 1.402(8) . ? C42 H42 0.9400 . ? C43 C44 1.430(9) . ? C43 C48 1.448(9) . ? C44 C45 1.357(9) . ? C44 H44 0.9400 . ? C45 C46 1.406(9) . ? C45 H45 0.9400 . ? C46 C47 1.381(9) . ? C46 H46 0.9400 . ? C47 C48 1.402(8) . ? C47 H47 0.9400 . ? C48 C49 1.419(9) . ? O11 H11A 0.7738 . ? O11 H11B 0.8178 . ? O12 H12A 1.0332 . ? O12 H12B 0.9047 . ? O13 C5 1.389(8) . ? O13 H13A 0.8300 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C5 H5C 0.9700 . ? O14 C6 1.442(9) . ? O14 H14A 0.8300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 H6C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N4 Ni N1 100.7(2) . . ? N4 Ni N2 93.1(2) . . ? N1 Ni N2 82.3(2) . . ? N4 Ni O1 85.5(2) . . ? N1 Ni O1 173.1(2) . . ? N2 Ni O1 94.5(2) . . ? N4 Ni N3 83.6(2) . . ? N1 Ni N3 93.0(2) . . ? N2 Ni N3 173.8(2) . . ? O1 Ni N3 90.6(2) . . ? N4 Ni O2 170.2(2) . . ? N1 Ni O2 88.7(2) . . ? N2 Ni O2 90.89(19) . . ? O1 Ni O2 85.3(2) . . ? N3 Ni O2 93.15(18) . . ? Ni O1 H1C 114.8 . . ? Ni O1 H1D 110.6 . . ? H1C O1 H1D 111.1 . . ? Ni O2 H2C 116.1 . . ? Ni O2 H2D 118.2 . . ? H2C O2 H2D 109.6 . . ? C1 N1 Ni 108.1(5) . . ? C1 N1 H1E 110.1 . . ? Ni N1 H1E 110.1 . . ? C1 N1 H1F 110.1 . . ? Ni N1 H1F 110.1 . . ? H1E N1 H1F 108.4 . . ? C2 C1 N1 105.8(6) . . ? C2 C1 H1A 110.6 . . ? N1 C1 H1A 110.6 . . ? C2 C1 H1B 110.6 . . ? N1 C1 H1B 110.6 . . ? H1A C1 H1B 108.7 . . ? C1 C2 N2 108.3(6) . . ? C1 C2 H2A 110.0 . . ? N2 C2 H2A 110.0 . . ? C1 C2 H2B 110.0 . . ? N2 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? C2 N2 Ni 106.0(4) . . ? C2 N2 H2E 110.5 . . ? Ni N2 H2E 110.5 . . ? C2 N2 H2F 110.5 . . ? Ni N2 H2F 110.5 . . ? H2E N2 H2F 108.7 . . ? C3 N3 Ni 107.0(4) . . ? C3 N3 H3C 110.3 . . ? Ni N3 H3C 110.3 . . ? C3 N3 H3D 110.3 . . ? Ni N3 H3D 110.3 . . ? H3C N3 H3D 108.6 . . ? N3 C3 C4 107.6(6) . . ? N3 C3 H3A 110.2 . . ? C4 C3 H3A 110.2 . . ? N3 C3 H3B 110.2 . . ? C4 C3 H3B 110.2 . . ? H3A C3 H3B 108.5 . . ? N4 C4 C3 107.7(6) . . ? N4 C4 H4A 110.2 . . ? C3 C4 H4A 110.2 . . ? N4 C4 H4B 110.2 . . ? C3 C4 H4B 110.2 . . ? H4A C4 H4B 108.5 . . ? C4 N4 Ni 108.9(4) . . ? C4 N4 H4C 109.9 . . ? Ni N4 H4C 109.9 . . ? C4 N4 H4D 109.9 . . ? Ni N4 H4D 109.9 . . ? H4C N4 H4D 108.3 . . ? O6 P1 O5 118.1(3) . . ? O6 P1 O3 111.4(3) . . ? O5 P1 O3 106.2(3) . . ? O6 P1 O4 106.4(3) . . ? O5 P1 O4 112.0(3) . . ? O3 P1 O4 101.6(2) . . ? C10 O3 P1 114.5(4) . . ? C20 O4 P1 121.8(4) . . ? C19 C10 O3 119.4(6) . . ? C19 C10 C11 123.7(7) . . ? O3 C10 C11 116.9(7) . . ? C12 C11 C10 117.8(7) . . ? C12 C11 H11 121.1 . . ? C10 C11 H11 121.1 . . ? C11 C12 C13 122.2(7) . . ? C11 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? C12 C13 C14 123.0(7) . . ? C12 C13 C18 120.4(7) . . ? C14 C13 C18 116.5(6) . . ? C15 C14 C13 124.1(7) . . ? C15 C14 H14 118.0 . . ? C13 C14 H14 118.0 . . ? C14 C15 C16 119.4(8) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C17 C16 C15 118.7(7) . . ? C17 C16 H16 120.6 . . ? C15 C16 H16 120.6 . . ? C16 C17 C18 122.9(7) . . ? C16 C17 H17 118.5 . . ? C18 C17 H17 118.5 . . ? C17 C18 C13 118.2(7) . . ? C17 C18 C19 123.5(6) . . ? C13 C18 C19 118.1(6) . . ? C10 C19 C18 117.4(6) . . ? C10 C19 C29 119.7(6) . . ? C18 C19 C29 122.8(6) . . ? C29 C20 O4 119.9(6) . . ? C29 C20 C21 123.1(7) . . ? O4 C20 C21 117.0(6) . . ? C22 C21 C20 118.6(7) . . ? C22 C21 H21 120.7 . . ? C20 C21 H21 120.7 . . ? C21 C22 C23 122.3(6) . . ? C21 C22 H22 118.9 . . ? C23 C22 H22 118.9 . . ? C24 C23 C22 122.9(7) . . ? C24 C23 C28 117.8(6) . . ? C22 C23 C28 119.3(6) . . ? C25 C24 C23 122.1(7) . . ? C25 C24 H24 119.0 . . ? C23 C24 H24 119.0 . . ? C24 C25 C26 119.1(7) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C27 C26 C25 121.6(7) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C26 C27 C28 120.7(7) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C23 118.6(6) . . ? C27 C28 C29 124.1(6) . . ? C23 C28 C29 117.1(6) . . ? C20 C29 C28 119.5(6) . . ? C20 C29 C19 120.0(6) . . ? C28 C29 C19 120.4(6) . . ? O10 P2 O9 118.7(3) . . ? O10 P2 O7 112.2(3) . . ? O9 P2 O7 104.8(3) . . ? O10 P2 O8 106.6(3) . . ? O9 P2 O8 111.2(3) . . ? O7 P2 O8 102.0(2) . . ? C30 O7 P2 120.7(4) . . ? C40 O8 P2 115.2(4) . . ? O7 C30 C39 118.8(6) . . ? O7 C30 C31 118.2(6) . . ? C39 C30 C31 122.9(6) . . ? C32 C31 C30 120.0(7) . . ? C32 C31 H31 120.0 . . ? C30 C31 H31 120.0 . . ? C31 C32 C33 120.5(7) . . ? C31 C32 H32 119.7 . . ? C33 C32 H32 119.7 . . ? C38 C33 C34 119.6(7) . . ? C38 C33 C32 120.0(7) . . ? C34 C33 C32 120.4(7) . . ? C35 C34 C33 120.3(7) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 121.3(7) . . ? C34 C35 H35 119.4 . . ? C36 C35 H35 119.4 . . ? C37 C36 C35 118.6(7) . . ? C37 C36 H36 120.7 . . ? C35 C36 H36 120.7 . . ? C36 C37 C38 121.7(7) . . ? C36 C37 H37 119.2 . . ? C38 C37 H37 119.2 . . ? C37 C38 C33 118.5(6) . . ? C37 C38 C39 121.8(6) . . ? C33 C38 C39 119.7(6) . . ? C30 C39 C38 116.6(6) . . ? C30 C39 C49 120.3(6) . . ? C38 C39 C49 123.0(6) . . ? C41 C40 C49 124.2(7) . . ? C41 C40 O8 117.6(6) . . ? C49 C40 O8 118.1(6) . . ? C42 C41 C40 119.8(7) . . ? C42 C41 H41 120.1 . . ? C40 C41 H41 120.1 . . ? C41 C42 C43 120.8(7) . . ? C41 C42 H42 119.6 . . ? C43 C42 H42 119.6 . . ? C42 C43 C44 121.6(7) . . ? C42 C43 C48 118.6(7) . . ? C44 C43 C48 119.7(6) . . ? C45 C44 C43 120.2(7) . . ? C45 C44 H44 119.9 . . ? C43 C44 H44 119.9 . . ? C44 C45 C46 120.4(7) . . ? C44 C45 H45 119.8 . . ? C46 C45 H45 119.8 . . ? C47 C46 C45 120.9(7) . . ? C47 C46 H46 119.6 . . ? C45 C46 H46 119.6 . . ? C46 C47 C48 121.3(7) . . ? C46 C47 H47 119.3 . . ? C48 C47 H47 119.3 . . ? C47 C48 C49 122.9(6) . . ? C47 C48 C43 117.4(7) . . ? C49 C48 C43 119.7(6) . . ? C40 C49 C48 116.6(6) . . ? C40 C49 C39 119.8(6) . . ? C48 C49 C39 123.7(6) . . ? H11A O11 H11B 121.2 . . ? H12A O12 H12B 107.0 . . ? C5 O13 H13A 109.5 . . ? O13 C5 H5A 109.5 . . ? O13 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O13 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C6 O14 H14A 109.5 . . ? O14 C6 H6A 109.5 . . ? O14 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O14 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? 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 O1 H1C O13 0.73 1.95 2.652(7) 161.2 . O1 H1D O6 0.76 2.13 2.869(7) 165.1 . O2 H2C O11 0.79 1.97 2.736(5) 165.1 . O2 H2D O12 0.99 1.65 2.635(7) 177.2 4_464 N1 H1E O12 0.91 2.10 2.963(7) 158.2 3_444 N1 H1F O9 0.91 2.39 3.175(8) 144.6 4_454 N2 H2E O11 0.91 2.35 3.187(8) 152.5 . N2 H2F O6 0.91 2.39 3.176(7) 144.4 2_564 N3 H3C O6 0.91 2.18 3.058(7) 162.2 . N3 H3D O9 0.91 1.96 2.851(7) 167.8 4_454 N4 H4C O2 0.91 2.22 3.081(7) 157.3 2_564 N4 H4D O6 0.91 2.36 3.014(7) 128.4 2_564 O11 H11A O10 0.77 2.07 2.805(7) 159.2 4_464 O11 H11B O5 0.82 2.05 2.787(7) 149.7 1_565 O12 H12A O14 1.03 1.61 2.635(8) 168.8 . O12 H12B O9 0.90 1.86 2.704(7) 153.5 1_565 O13 H13A O5 0.83 1.88 2.653(7) 153.7 1_565 O14 H14A O10 0.83 1.88 2.693(7) 164.7 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.60 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.278 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.087