# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name T.Yamada H.Kitagawa _publ_contact_author_name 'Teppei Yamada' _publ_contact_author_email teppei343@gmail.com data_p-1b _database_code_depnum_ccdc_archive 'CCDC 869666' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (Zn2(dppip)2(bpy)(H2O)4)(dmf)(H2O)1.5 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H60 N3 O22 P2 Zn2' _chemical_formula_weight 1139.60 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' O O 0.0106 0.0060 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5545(12) _cell_length_b 10.3457(13) _cell_length_c 13.7876(17) _cell_angle_alpha 81.6150(10) _cell_angle_beta 82.8130(10) _cell_angle_gamma 70.7230(10) _cell_volume 1268.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5785 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 27.70 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 593 _exptl_absorpt_coefficient_mu 1.090 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7369 _exptl_absorpt_correction_T_max 0.8124 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayered confocal mirror' _diffrn_measurement_device 'Bruker APEX-II CCD-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12527 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_sigmaI/netI 0.1235 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 26.99 _reflns_number_total 5347 _reflns_number_gt 3922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _publ_section_references ; Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses, Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn., 51, 218-224. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+6.5379P] 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 5347 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0788 _refine_ls_wR_factor_ref 0.1709 _refine_ls_wR_factor_gt 0.1565 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.23805(6) 0.44403(6) 0.13999(5) 0.02064(19) Uani 1 1 d . . . O1 O 0.4237(4) 0.3260(4) 0.1911(3) 0.0218(8) Uani 1 1 d . . . C1 C 0.5362(5) 0.3676(5) 0.1693(3) 0.0148(10) Uani 1 1 d . . . O2 O 0.5302(4) 0.4826(3) 0.1262(3) 0.0223(8) Uani 1 1 d . . . C2 C 0.6830(5) 0.2659(5) 0.1981(3) 0.0135(9) Uani 1 1 d . A . C3 C 0.8131(5) 0.3001(5) 0.1783(3) 0.0135(9) Uani 1 1 d . . . H3 H 0.812(6) 0.384(5) 0.157(4) 0.012(12) Uiso 1 1 d . . . O3 O 1.0741(3) 0.3681(3) 0.1639(3) 0.0163(7) Uani 1 1 d . . . C4 C 1.0914(5) 0.2396(5) 0.1762(3) 0.0136(9) Uani 1 1 d . . . O4 O 1.2106(4) 0.1442(4) 0.1694(3) 0.0220(8) Uani 1 1 d . . . C5 C 0.9499(5) 0.2033(5) 0.2006(3) 0.0124(9) Uani 1 1 d . . . C6 C 0.9542(6) 0.0708(5) 0.2427(3) 0.0147(10) Uani 1 1 d . . . H6 H 1.049(6) 0.003(6) 0.255(4) 0.021(14) Uiso 1 1 d . . . P1 P 0.82869(18) -0.12810(13) 0.32718(10) 0.0258(4) Uani 1 1 d . . . O5 O 0.7162(8) -0.1002(7) 0.4226(5) 0.0219(16) Uani 0.50 1 d P A 1 O6 O 0.7044(8) -0.1577(7) 0.2590(6) 0.0191(15) Uani 0.50 1 d P A 1 C7 C 0.8234(5) 0.0381(5) 0.2659(3) 0.0153(10) Uani 1 1 d . A . C8 C 0.6878(5) 0.1349(5) 0.2428(3) 0.0144(10) Uani 1 1 d . . . H8 H 0.594(6) 0.110(5) 0.256(4) 0.014(13) Uiso 1 1 d . . . C9 C 0.7783(18) -0.0970(16) 0.5145(12) 0.051(4) Uiso 0.50 1 d P A 1 C10 C 0.752(3) 0.059(3) 0.5234(19) 0.104(8) Uiso 0.50 1 d P A 1 C11 C 0.673(2) -0.1452(18) 0.5965(13) 0.047(5) Uiso 0.50 1 d P A 1 C12 C 0.6588(14) -0.2330(12) 0.2599(9) 0.025(2) Uiso 0.50 1 d P A 2 C13 C 0.709(2) -0.3892(18) 0.2790(13) 0.028(5) Uiso 0.50 1 d P A 1 C14 C 0.4831(18) -0.1762(16) 0.2539(11) 0.031(4) Uiso 0.50 1 d P A 2 O9 O 0.9642(11) -0.2249(9) 0.3317(7) 0.023(2) Uiso 0.50 1 d P A 1 N1 N 0.1542(4) 0.6465(4) 0.0879(3) 0.0125(8) Uani 1 1 d . . . C19 C 0.2369(6) 0.7306(5) 0.0716(5) 0.0300(14) Uani 1 1 d . . . H19 H 0.341(7) 0.690(6) 0.085(4) 0.025(15) Uiso 1 1 d . . . C20 C 0.1806(6) 0.8688(5) 0.0388(5) 0.0317(15) Uani 1 1 d . . . H20 H 0.247(7) 0.912(7) 0.023(5) 0.042(19) Uiso 1 1 d . . . C21 C 0.0317(5) 0.9258(4) 0.0191(3) 0.0135(9) Uani 1 1 d . . . C22 C -0.0535(5) 0.8388(5) 0.0373(4) 0.0175(10) Uani 1 1 d . . . H22 H -0.158(6) 0.866(5) 0.025(4) 0.019(14) Uiso 1 1 d . . . C23 C 0.0093(5) 0.7012(5) 0.0699(4) 0.0168(10) Uani 1 1 d . . . H23 H -0.048(6) 0.642(5) 0.083(4) 0.014(13) Uiso 1 1 d . . . O11 O 0.2992(4) 0.3885(4) -0.0074(3) 0.0217(8) Uani 1 1 d . . . O12 O 0.1830(6) 0.5200(5) 0.2873(4) 0.0523(13) Uani 1 1 d . . . H2 H 0.350(6) 0.317(6) -0.004(4) 0.016(16) Uiso 1 1 d . . . H2A H 0.344(6) 0.438(6) -0.039(4) 0.018(14) Uiso 1 1 d . . . O15 O 0.088(3) 0.503(2) 0.341(2) 0.035(10) Uani 0.165(16) 1 d P . . H2B H 0.401(8) 0.127(7) 0.086(5) 0.03(2) Uiso 1 1 d . . . H2C H 0.481(14) 0.066(10) 0.008(10) 0.12(5) Uiso 1 1 d . . . O14 O 0.4614(5) 0.1180(4) 0.0468(4) 0.0306(10) Uani 1 1 d . . . O16 O 0.003(3) 0.525(3) 0.4681(19) 0.075(10) Uani 0.251(16) 1 d P . . O7 O 0.9717(8) -0.2403(7) 0.2931(6) 0.0147(16) Uani 0.50 1 d P A 2 C15 C 0.7201(18) -0.1436(15) 0.5990(11) 0.032(3) Uiso 0.50 1 d P A 2 C16 C 0.9857(14) -0.2868(12) 0.5600(9) 0.032(3) Uiso 0.50 1 d P A 2 C17 C 0.8319(12) -0.2152(10) 0.5244(8) 0.021(2) Uiso 0.50 1 d P A 2 C18 C 0.6146(13) -0.2497(11) 0.2977(9) 0.022(2) Uiso 0.50 1 d P A 1 O8 O 0.6894(8) -0.1541(6) 0.3309(5) 0.0156(14) Uani 0.50 1 d P A 2 O10 O 0.8453(8) -0.1084(7) 0.4425(5) 0.0180(15) Uani 0.50 1 d P A 2 N2 N 0.6116(10) 0.3784(10) 0.4930(7) 0.027(2) Uani 0.50 1 d P B 3 O13 O 0.3896(13) 0.4672(13) 0.4279(8) 0.039(3) Uani 0.50 1 d P C 2 C24 C 0.5075(14) 0.3750(14) 0.4387(9) 0.034(3) Uani 0.50 1 d P C 2 C25 C 0.594(2) 0.497(2) 0.5424(14) 0.045(5) Uani 0.50 1 d P B 3 H31 H 0.6028 0.4692 0.6115 0.067 Uiso 0.50 1 calc PR B 3 H32 H 0.4974 0.5630 0.5327 0.067 Uiso 0.50 1 calc PR B 3 H33 H 0.6693 0.5378 0.5159 0.067 Uiso 0.50 1 calc PR B 3 C26 C 0.7556(14) 0.2700(15) 0.4972(11) 0.045(3) Uani 0.50 1 d P B 3 H26 H 0.7513 0.1915 0.4696 0.08(6) Uiso 0.50 1 calc PR B 3 H26A H 0.7791 0.2438 0.5644 0.07(5) Uiso 0.50 1 calc PR B 3 H26B H 0.8310 0.3036 0.4602 0.23(16) Uiso 0.50 1 calc PR B 3 C27 C 0.4883(19) -0.2058(17) 0.2368(12) 0.036(4) Uiso 0.50 1 d P A 1 C28 C 0.719(2) -0.3935(19) 0.3000(14) 0.034(5) Uiso 0.50 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0064(3) 0.0117(3) 0.0420(4) 0.0056(2) -0.0087(3) -0.0017(2) O1 0.0086(17) 0.032(2) 0.0246(19) 0.0068(15) -0.0058(15) -0.0090(15) C1 0.013(2) 0.021(2) 0.009(2) -0.0024(18) -0.0013(19) -0.003(2) O2 0.0087(17) 0.0206(17) 0.033(2) 0.0059(15) -0.0039(16) -0.0022(14) C2 0.011(2) 0.017(2) 0.011(2) 0.0001(17) -0.0039(19) -0.0033(19) C3 0.012(2) 0.013(2) 0.013(2) -0.0010(17) 0.0000(19) -0.0019(19) O3 0.0049(15) 0.0172(16) 0.0254(19) 0.0002(13) -0.0009(14) -0.0027(14) C4 0.014(2) 0.021(2) 0.006(2) -0.0012(17) -0.0022(18) -0.005(2) O4 0.0073(17) 0.0219(18) 0.029(2) 0.0001(15) 0.0009(15) 0.0034(15) C5 0.008(2) 0.016(2) 0.011(2) -0.0029(17) -0.0014(18) -0.0017(19) C6 0.014(2) 0.014(2) 0.013(2) -0.0037(17) -0.002(2) 0.001(2) P1 0.0381(9) 0.0150(6) 0.0215(7) -0.0027(5) 0.0118(7) -0.0096(6) O5 0.027(4) 0.024(4) 0.019(4) 0.004(3) -0.009(3) -0.013(3) O6 0.022(4) 0.020(4) 0.018(4) 0.003(3) -0.003(3) -0.012(3) C7 0.018(3) 0.012(2) 0.014(2) -0.0010(17) 0.001(2) -0.003(2) C8 0.011(2) 0.020(2) 0.012(2) -0.0039(18) 0.0031(19) -0.006(2) N1 0.0075(19) 0.0127(18) 0.015(2) -0.0027(15) -0.0027(16) 0.0007(16) C19 0.009(2) 0.017(3) 0.062(4) 0.003(3) -0.015(3) -0.001(2) C20 0.011(3) 0.016(3) 0.068(5) 0.006(3) -0.016(3) -0.005(2) C21 0.008(2) 0.014(2) 0.016(2) -0.0048(18) -0.0012(19) 0.0017(19) C22 0.007(2) 0.018(2) 0.024(3) 0.0015(19) -0.003(2) 0.0008(19) C23 0.009(2) 0.019(2) 0.021(3) 0.0011(19) -0.002(2) -0.004(2) O11 0.016(2) 0.0169(19) 0.029(2) 0.0057(16) -0.0032(17) -0.0041(17) O12 0.062(4) 0.052(3) 0.041(3) -0.004(2) -0.013(3) -0.013(3) O15 0.017(14) 0.020(13) 0.048(18) 0.009(11) 0.011(12) 0.013(10) O14 0.020(2) 0.020(2) 0.048(3) -0.0125(19) 0.009(2) -0.0022(18) O16 0.069(16) 0.062(16) 0.08(2) 0.041(12) -0.010(14) -0.022(12) O7 0.013(4) 0.020(4) 0.004(4) 0.002(3) 0.000(3) 0.002(3) O8 0.015(4) 0.014(3) 0.016(4) -0.001(3) -0.003(3) -0.003(3) O10 0.023(4) 0.018(3) 0.013(3) 0.003(3) -0.002(3) -0.008(3) N2 0.021(5) 0.041(5) 0.018(5) -0.003(4) -0.002(4) -0.008(4) O13 0.026(6) 0.052(7) 0.036(7) -0.009(5) -0.020(5) -0.002(5) C24 0.029(7) 0.053(8) 0.024(6) 0.002(5) -0.008(5) -0.021(6) C25 0.047(10) 0.059(12) 0.041(11) 0.004(8) -0.022(8) -0.029(9) C26 0.020(6) 0.056(9) 0.047(8) 0.003(7) -0.011(6) 0.002(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.941(3) . ? Zn1 O3 1.946(3) 1_455 ? Zn1 N1 2.035(4) . ? Zn1 O11 2.151(4) . ? Zn1 O12 2.223(5) . ? O1 C1 1.272(6) . ? C1 O2 1.237(5) . ? C1 C2 1.508(6) . ? C2 C3 1.386(6) . ? C2 C8 1.393(6) . ? C3 C5 1.398(6) . ? O3 C4 1.272(5) . ? O3 Zn1 1.946(3) 1_655 ? C4 O4 1.241(6) . ? C4 C5 1.506(6) . ? C5 C6 1.398(6) . ? C6 C7 1.388(7) . ? P1 O9 1.353(10) . ? P1 O8 1.435(7) . ? P1 O7 1.545(8) . ? P1 O5 1.588(8) . ? P1 O10 1.666(7) . ? P1 O6 1.729(7) . ? P1 C7 1.790(4) . ? O5 C9 1.474(17) . ? O6 C18 1.485(12) . ? C7 C8 1.392(7) . ? C9 C11 1.56(2) . ? C9 C10 1.56(3) . ? C12 O8 1.473(13) . ? C12 C14 1.59(2) . ? C12 C28 1.60(2) . ? C13 C18 1.47(2) . ? N1 C19 1.336(6) . ? N1 C23 1.351(6) . ? C19 C20 1.379(7) . ? C20 C21 1.393(7) . ? C21 C22 1.380(6) . ? C21 C21 1.493(8) 2_575 ? C22 C23 1.380(6) . ? O12 O15 1.15(2) . ? O16 O16 0.95(4) 2_566 ? C15 C17 1.475(19) . ? C16 C17 1.518(16) . ? C17 O10 1.485(11) . ? C18 C27 1.47(2) . ? N2 C25 1.44(2) . ? N2 C26 1.462(16) . ? O13 C24 1.221(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 115.38(13) . 1_455 ? O1 Zn1 N1 135.61(15) . . ? O3 Zn1 N1 107.83(14) 1_455 . ? O1 Zn1 O11 95.00(16) . . ? O3 Zn1 O11 94.91(15) 1_455 . ? N1 Zn1 O11 90.87(15) . . ? O1 Zn1 O12 85.56(18) . . ? O3 Zn1 O12 90.13(18) 1_455 . ? N1 Zn1 O12 84.67(17) . . ? O11 Zn1 O12 174.10(17) . . ? C1 O1 Zn1 116.8(3) . . ? O2 C1 O1 123.8(4) . . ? O2 C1 C2 120.4(4) . . ? O1 C1 C2 115.7(4) . . ? C3 C2 C8 119.8(4) . . ? C3 C2 C1 120.8(4) . . ? C8 C2 C1 119.3(4) . . ? C2 C3 C5 120.6(4) . . ? C4 O3 Zn1 123.8(3) . 1_655 ? O4 C4 O3 126.8(4) . . ? O4 C4 C5 118.2(4) . . ? O3 C4 C5 115.0(4) . . ? C3 C5 C6 119.1(4) . . ? C3 C5 C4 120.4(4) . . ? C6 C5 C4 120.4(4) . . ? C7 C6 C5 120.2(4) . . ? O9 P1 O8 125.9(5) . . ? O9 P1 O7 21.3(4) . . ? O8 P1 O7 118.1(4) . . ? O9 P1 O5 121.0(5) . . ? O8 P1 O5 60.8(4) . . ? O7 P1 O5 138.4(4) . . ? O9 P1 O10 85.8(5) . . ? O8 P1 O10 104.9(4) . . ? O7 P1 O10 107.1(4) . . ? O5 P1 O10 45.9(3) . . ? O9 P1 O6 116.8(5) . . ? O8 P1 O6 34.8(3) . . ? O7 P1 O6 99.0(4) . . ? O5 P1 O6 94.6(4) . . ? O10 P1 O6 139.7(4) . . ? O9 P1 C7 116.7(4) . . ? O8 P1 C7 113.0(3) . . ? O7 P1 C7 110.9(3) . . ? O5 P1 C7 105.9(3) . . ? O10 P1 C7 101.0(3) . . ? O6 P1 C7 97.6(3) . . ? C9 O5 P1 117.2(8) . . ? C18 O6 P1 123.0(6) . . ? C6 C7 C8 120.2(4) . . ? C6 C7 P1 120.0(4) . . ? C8 C7 P1 119.9(4) . . ? C7 C8 C2 119.9(4) . . ? O5 C9 C11 103.7(12) . . ? O5 C9 C10 106.1(14) . . ? C11 C9 C10 106.6(15) . . ? O8 C12 C14 105.4(10) . . ? O8 C12 C28 108.1(10) . . ? C14 C12 C28 113.2(12) . . ? C19 N1 C23 117.4(4) . . ? C19 N1 Zn1 122.5(3) . . ? C23 N1 Zn1 120.1(3) . . ? N1 C19 C20 123.1(5) . . ? C19 C20 C21 119.9(5) . . ? C22 C21 C20 116.7(4) . . ? C22 C21 C21 122.0(5) . 2_575 ? C20 C21 C21 121.3(5) . 2_575 ? C21 C22 C23 120.7(4) . . ? N1 C23 C22 122.2(4) . . ? O15 O12 Zn1 123.4(16) . . ? C15 C17 O10 106.6(9) . . ? C15 C17 C16 114.5(10) . . ? O10 C17 C16 107.5(8) . . ? C27 C18 C13 109.4(12) . . ? C27 C18 O6 105.1(10) . . ? C13 C18 O6 105.9(11) . . ? P1 O8 C12 122.5(7) . . ? C17 O10 P1 120.5(6) . . ? C25 N2 C26 116.4(12) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.708 _refine_diff_density_min -1.200 _refine_diff_density_rms 0.128 data_4 _database_code_depnum_ccdc_archive 'CCDC 869667' #TrackingRef '.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ' dizinc 4,4'-bipyridyl bis(3-etacarboxy-5-carboxylphoshonate trihydrate' ; _chemical_name_common ; ' dizinc 4,4'-bipyridyl bis(3-etacarboxy-5-carboxylphoshonate trihydrate' ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 N O10 P Zn' _chemical_formula_weight 483.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.463(2) _cell_length_b 11.263(3) _cell_length_c 11.774(3) _cell_angle_alpha 110.960(2) _cell_angle_beta 96.523(3) _cell_angle_gamma 108.941(2) _cell_volume 957.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ' 8242' _cell_measurement_theta_min ' 2.17' _cell_measurement_theta_max ' 27.63' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 498 _exptl_absorpt_coefficient_mu 1.423 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6748 _exptl_absorpt_correction_T_max 0.8708 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayered confocal mirror' _diffrn_measurement_device 'Bruker APEX-II CCD-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8843 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3348 _reflns_number_gt 3269 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _publ_section_references ; Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses, Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn., 51, 218-224. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.7965P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3348 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0755 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 Zn1 Zn 0.64466(3) 0.03072(2) 0.30826(2) 0.01311(10) Uani 1 1 d . . . C1 C 0.2037(2) -0.0378(2) 0.18674(19) 0.0137(4) Uani 1 1 d . . . C2 C 0.2466(3) -0.0349(2) 0.07616(19) 0.0141(4) Uani 1 1 d . . . C3 C 0.2372(2) 0.0671(2) 0.03803(19) 0.0131(4) Uani 1 1 d . . . C4 C 0.1862(2) 0.1682(2) 0.11208(19) 0.0141(4) Uani 1 1 d . . . C5 C 0.1414(2) 0.1653(2) 0.22156(19) 0.0143(4) Uani 1 1 d . . . C6 C 0.1485(3) 0.0618(2) 0.25860(19) 0.0142(4) Uani 1 1 d . . . P1 P 0.23824(7) -0.16077(5) 0.24137(5) 0.01291(13) Uani 1 1 d . . . O1 O 0.43011(18) -0.11127(14) 0.29769(13) 0.0161(3) Uani 1 1 d . . . O2 O 0.12781(19) -0.18222(15) 0.32989(14) 0.0174(3) Uani 1 1 d . . . O3 O 0.17505(18) -0.30065(14) 0.11922(14) 0.0173(3) Uani 1 1 d . . . C7 C 0.2926(3) -0.3605(2) 0.0601(2) 0.0215(5) Uani 1 1 d . . . C8 C 0.2995(4) -0.4687(3) 0.1041(3) 0.0366(6) Uani 1 1 d . . . H8 H 0.279(3) -0.102(3) 0.026(2) 0.023(6) Uiso 1 1 d . . . H8A H 0.435(3) 0.351(3) 0.591(2) 0.018(6) Uiso 1 1 d . . . H8B H 0.121(3) 0.060(2) 0.329(2) 0.010(5) Uiso 1 1 d . . . H8C H 0.508(3) 0.166(3) 0.522(2) 0.024(6) Uiso 1 1 d . . . H8D H 0.402(3) -0.289(3) 0.089(2) 0.019(6) Uiso 1 1 d . . . H8E H 0.701(3) 0.285(3) 0.274(2) 0.020(6) Uiso 1 1 d . . . H8F H 0.640(4) 0.481(3) 0.344(3) 0.032(7) Uiso 1 1 d . . . H8G H 0.180(3) 0.236(3) 0.085(2) 0.025(7) Uiso 1 1 d . . . H8H H 0.804(4) -0.065(3) 0.407(3) 0.033(8) Uiso 1 1 d . . . C9 C 0.2195(4) -0.4194(3) -0.0802(2) 0.0336(6) Uani 1 1 d . . . H9 H 0.134(4) 0.239(3) 0.695(3) 0.036(9) Uiso 1 1 d . . . H9A H 0.828(3) 0.057(3) 0.497(3) 0.021(7) Uiso 1 1 d . . . H9B H 0.303(4) -0.455(3) -0.123(3) 0.047(9) Uiso 1 1 d . . . H9C H 0.069(4) 0.652(4) 0.367(3) 0.042(8) Uiso 1 1 d . . . H9D H 0.377(4) -0.510(3) 0.067(3) 0.043(8) Uiso 1 1 d . . . H9E H 0.101(5) -0.505(4) -0.110(3) 0.057(10) Uiso 1 1 d . . . H9F H 0.005(4) 0.613(3) 0.448(3) 0.041(9) Uiso 1 1 d . . . H9G H 0.203(4) -0.347(4) -0.107(3) 0.052(9) Uiso 1 1 d . . . H9H H 0.252(5) 0.230(4) 0.765(4) 0.056(10) Uiso 1 1 d . . . C10 C 0.2791(2) 0.0690(2) -0.08225(19) 0.0148(4) Uani 1 1 d . . . H9I H 0.079(5) 0.442(5) 0.319(4) 0.080(13) Uiso 1 1 d . . . H10 H 0.341(5) -0.429(4) 0.195(4) 0.058(10) Uiso 1 1 d . . . H10A H 0.177(5) -0.551(4) 0.076(4) 0.065(11) Uiso 1 1 d . . . O4 O 0.30284(19) -0.03737(15) -0.15396(13) 0.0177(3) Uani 1 1 d . . . O5 O 0.2890(2) 0.16871(16) -0.10722(14) 0.0197(3) Uani 1 1 d . . . C11 C 0.0882(3) 0.2743(2) 0.3033(2) 0.0168(4) Uani 1 1 d . . . O6 O 0.0498(2) 0.27665(17) 0.39971(16) 0.0287(4) Uani 1 1 d . . . O7 O 0.0921(2) 0.36796(18) 0.26033(16) 0.0288(4) Uani 1 1 d . . . N1 N 0.6074(2) 0.20762(17) 0.38700(16) 0.0145(3) Uani 1 1 d . . . C12 C 0.5314(3) 0.2303(2) 0.4823(2) 0.0163(4) Uani 1 1 d . . . C13 C 0.4875(3) 0.3428(2) 0.5286(2) 0.0166(4) Uani 1 1 d . . . C14 C 0.5237(3) 0.4394(2) 0.47674(19) 0.0146(4) Uani 1 1 d . . . C15 C 0.6061(3) 0.4163(2) 0.3794(2) 0.0236(5) Uani 1 1 d . . . C16 C 0.6449(3) 0.3011(2) 0.3377(2) 0.0211(5) Uani 1 1 d . . . O8 O 0.8095(2) 0.01478(18) 0.42750(17) 0.0191(3) Uani 1 1 d . . . O9 O 0.2266(2) 0.24478(17) 0.69634(16) 0.0223(3) Uani 1 1 d . . . O10 O 0.0285(2) 0.57968(17) 0.38370(17) 0.0226(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 Zn1 0.02055(15) 0.01438(15) 0.01136(15) 0.00783(11) 0.00937(10) 0.01081(11) C1 0.0152(9) 0.0154(10) 0.0136(10) 0.0078(8) 0.0060(8) 0.0071(8) C2 0.0168(9) 0.0154(10) 0.0134(10) 0.0062(8) 0.0071(8) 0.0091(8) C3 0.0128(9) 0.0158(10) 0.0131(10) 0.0075(8) 0.0050(8) 0.0065(8) C4 0.0153(9) 0.0160(10) 0.0145(10) 0.0088(8) 0.0055(8) 0.0074(8) C5 0.0155(9) 0.0153(10) 0.0144(10) 0.0067(8) 0.0068(8) 0.0075(8) C6 0.0170(10) 0.0180(10) 0.0107(10) 0.0075(8) 0.0067(8) 0.0077(8) P1 0.0187(3) 0.0142(3) 0.0118(3) 0.0082(2) 0.0086(2) 0.0090(2) O1 0.0190(7) 0.0172(7) 0.0169(7) 0.0103(6) 0.0068(6) 0.0087(6) O2 0.0237(7) 0.0218(8) 0.0165(7) 0.0129(6) 0.0125(6) 0.0130(6) O3 0.0205(7) 0.0155(7) 0.0169(8) 0.0057(6) 0.0075(6) 0.0087(6) C7 0.0227(11) 0.0214(11) 0.0218(12) 0.0075(9) 0.0126(9) 0.0097(10) C8 0.0524(17) 0.0423(16) 0.0343(16) 0.0195(13) 0.0182(13) 0.0357(15) C9 0.0505(16) 0.0325(14) 0.0214(13) 0.0108(11) 0.0164(12) 0.0190(13) C10 0.0134(9) 0.0197(10) 0.0139(10) 0.0086(9) 0.0055(8) 0.0073(8) O4 0.0266(8) 0.0203(7) 0.0139(7) 0.0092(6) 0.0124(6) 0.0139(6) O5 0.0273(8) 0.0227(8) 0.0191(8) 0.0149(7) 0.0120(6) 0.0129(7) C11 0.0193(10) 0.0158(10) 0.0179(11) 0.0072(9) 0.0081(8) 0.0090(8) O6 0.0521(11) 0.0275(9) 0.0241(9) 0.0156(7) 0.0280(8) 0.0255(8) O7 0.0562(11) 0.0276(9) 0.0253(9) 0.0181(7) 0.0263(8) 0.0312(9) N1 0.0196(8) 0.0149(8) 0.0131(9) 0.0073(7) 0.0080(7) 0.0088(7) C12 0.0230(10) 0.0166(10) 0.0158(10) 0.0098(9) 0.0097(8) 0.0108(9) C13 0.0234(10) 0.0202(10) 0.0141(10) 0.0099(9) 0.0123(9) 0.0128(9) C14 0.0170(10) 0.0156(10) 0.0148(10) 0.0079(8) 0.0080(8) 0.0079(8) C15 0.0385(13) 0.0233(11) 0.0263(12) 0.0183(10) 0.0231(11) 0.0194(10) C16 0.0320(12) 0.0198(11) 0.0217(12) 0.0124(9) 0.0191(10) 0.0144(10) O8 0.0267(8) 0.0204(8) 0.0136(9) 0.0075(7) 0.0059(7) 0.0128(7) O9 0.0247(9) 0.0287(9) 0.0248(9) 0.0166(7) 0.0133(7) 0.0161(7) O10 0.0357(9) 0.0193(8) 0.0215(9) 0.0112(7) 0.0176(7) 0.0150(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 1.9397(15) 2_655 ? Zn1 O1 1.9470(14) . ? Zn1 O8 1.9615(16) . ? Zn1 N1 2.0202(17) . ? C1 C6 1.394(3) . ? C1 C2 1.399(3) . ? C1 P1 1.810(2) . ? C2 C3 1.396(3) . ? C3 C4 1.392(3) . ? C3 C10 1.504(3) . ? C4 C5 1.392(3) . ? C5 C6 1.398(3) . ? C5 C11 1.500(3) . ? P1 O2 1.5076(14) . ? P1 O1 1.5134(15) . ? P1 O3 1.5792(15) . ? O3 C7 1.479(3) . ? C7 C8 1.499(3) . ? C7 C9 1.507(4) . ? C10 O5 1.239(3) . ? C10 O4 1.288(3) . ? O4 Zn1 1.9397(15) 2_655 ? C11 O6 1.210(3) . ? C11 O7 1.316(3) . ? N1 C12 1.343(3) . ? N1 C16 1.345(3) . ? C12 C13 1.377(3) . ? C13 C14 1.397(3) . ? C14 C15 1.398(3) . ? C14 C14 1.482(4) 2_666 ? C15 C16 1.374(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 O4 Zn1 O1 118.99(6) 2_655 . ? O4 Zn1 O8 119.77(7) 2_655 . ? O1 Zn1 O8 100.53(7) . . ? O4 Zn1 N1 101.73(6) 2_655 . ? O1 Zn1 N1 103.41(7) . . ? O8 Zn1 N1 111.53(7) . . ? C6 C1 C2 119.25(18) . . ? C6 C1 P1 120.90(15) . . ? C2 C1 P1 119.63(15) . . ? C3 C2 C1 120.98(18) . . ? C4 C3 C2 119.32(18) . . ? C4 C3 C10 119.36(17) . . ? C2 C3 C10 121.31(18) . . ? C3 C4 C5 120.11(18) . . ? C4 C5 C6 120.47(18) . . ? C4 C5 C11 120.81(18) . . ? C6 C5 C11 118.71(18) . . ? C1 C6 C5 119.83(19) . . ? O2 P1 O1 114.25(8) . . ? O2 P1 O3 108.73(8) . . ? O1 P1 O3 109.74(8) . . ? O2 P1 C1 110.15(9) . . ? O1 P1 C1 108.43(9) . . ? O3 P1 C1 105.14(9) . . ? P1 O1 Zn1 137.92(9) . . ? C7 O3 P1 123.96(14) . . ? O3 C7 C8 108.21(18) . . ? O3 C7 C9 106.52(19) . . ? C8 C7 C9 112.6(2) . . ? O5 C10 O4 124.00(18) . . ? O5 C10 C3 120.17(18) . . ? O4 C10 C3 115.82(17) . . ? C10 O4 Zn1 114.33(13) . 2_655 ? O6 C11 O7 124.13(19) . . ? O6 C11 C5 123.06(19) . . ? O7 C11 C5 112.79(18) . . ? C12 N1 C16 117.90(17) . . ? C12 N1 Zn1 121.52(13) . . ? C16 N1 Zn1 120.34(14) . . ? N1 C12 C13 122.67(19) . . ? C12 C13 C14 119.83(19) . . ? C13 C14 C15 117.02(19) . . ? C13 C14 C14 121.2(2) . 2_666 ? C15 C14 C14 121.8(2) . 2_666 ? C16 C15 C14 119.8(2) . . ? N1 C16 C15 122.76(19) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.554 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.069 # Attachment '5.cif' data_(dma)[Zn(ipipc)] _database_code_depnum_ccdc_archive 'CCDC 869668' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dimethylammonium zinc (monoisopropyl 3,5-dicarboxyphenyl phosphonate) ; _chemical_name_common ;dimethylammonium zinc (monoisopropyl 3,5-dicarboxyphenyl phosphonate) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H18 N O7 P Zn' _chemical_formula_weight 396.62 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7414(11) _cell_length_b 16.0486(18) _cell_length_c 11.0596(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.4460(10) _cell_angle_gamma 90.00 _cell_volume 1721.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ' 7992' _cell_measurement_theta_min ' 2.45' _cell_measurement_theta_max ' 25.07' _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 1.552 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.8129 _exptl_absorpt_correction_T_max 0.9131 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayered confocal mirror' _diffrn_measurement_device 'Bruker APEX-II CCD-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14931 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.07 _reflns_number_total 3054 _reflns_number_gt 2523 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _publ_section_references ; Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses, Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn., 51, 218-224. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+3.3295P] 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 3054 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0880 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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 Zn1 Zn 0.65794(4) 0.41742(2) -0.08300(3) 0.01271(14) Uani 1 1 d . . . C1 C 0.6684(4) 0.2045(2) 0.1288(3) 0.0166(7) Uani 1 1 d . . . C2 C 0.5329(4) 0.1954(2) 0.1557(3) 0.0168(7) Uani 1 1 d . . . H2 H 0.4644 0.2326 0.1205 0.020(10) Uiso 1 1 calc R . . C3 C 0.4958(3) 0.1329(2) 0.2331(3) 0.0154(7) Uani 1 1 d . . . C4 C 0.5964(3) 0.0775(2) 0.2822(3) 0.0157(7) Uani 1 1 d . . . H4 H 0.5716 0.0340 0.3342 0.012(9) Uiso 1 1 calc R . . C5 C 0.7334(3) 0.0853(2) 0.2558(3) 0.0155(7) Uani 1 1 d . . . C6 C 0.7686(4) 0.1494(2) 0.1802(3) 0.0161(7) Uani 1 1 d . . . H6 H 0.8618 0.1559 0.1634 0.022(10) Uiso 1 1 calc R . . C7 C 0.7086(4) 0.2757(2) 0.0508(3) 0.0171(7) Uani 1 1 d . . . O1 O 0.8310(3) 0.29599(16) 0.0497(2) 0.0256(6) Uani 1 1 d . . . O2 O 0.6081(2) 0.31211(14) -0.0108(2) 0.0179(5) Uani 1 1 d . . . C8 C 0.3515(3) 0.1279(2) 0.2697(3) 0.0157(7) Uani 1 1 d . . . O3 O 0.3257(2) 0.06594(14) 0.3364(2) 0.0171(5) Uani 1 1 d . . . O4 O 0.2674(2) 0.18351(16) 0.2370(2) 0.0222(6) Uani 1 1 d . . . P1 P 0.86118(9) 0.01479(6) 0.32493(7) 0.0140(2) Uani 1 1 d . . . O5 O 0.9995(2) 0.05024(15) 0.30541(19) 0.0166(5) Uani 1 1 d . . . O6 O 0.8270(2) -0.00003(15) 0.4519(2) 0.0180(5) Uani 1 1 d . . . O7 O 0.8400(3) -0.07086(15) 0.2542(2) 0.0210(6) Uani 1 1 d . A . C9 C 0.8795(4) -0.0783(3) 0.1297(3) 0.0284(9) Uani 1 1 d . . . H9 H 0.002(5) 0.295(3) 0.143(4) 0.038(13) Uiso 1 1 d . . . H9A H 0.129(5) 0.263(3) 0.192(4) 0.034(12) Uiso 1 1 d . . . C10 C 0.7729(7) -0.1340(5) 0.0659(5) 0.084(2) Uani 1 1 d . A 1 H17 H 0.7665 -0.1856 0.1124 0.126 Uiso 1 1 calc R A 1 H18 H 0.7989 -0.1472 -0.0154 0.126 Uiso 1 1 calc R A 1 H19 H 0.6833 -0.1057 0.0589 0.126 Uiso 1 1 calc R A 1 C13 C 1.0220(6) -0.1149(4) 0.1342(5) 0.0601(15) Uani 1 1 d . A 1 H20 H 1.0872 -0.0783 0.1816 0.090 Uiso 1 1 calc R A 1 H21 H 1.0491 -0.1203 0.0515 0.090 Uiso 1 1 calc R A 1 H22 H 1.0225 -0.1700 0.1725 0.090 Uiso 1 1 calc R A 1 N1 N 0.0820(4) 0.3080(2) 0.1773(3) 0.0275(8) Uani 1 1 d . . . C14 C 0.1559(5) 0.3591(3) 0.0922(4) 0.0344(10) Uani 1 1 d . . . H14 H 0.2495 0.3709 0.1287 0.048(14) Uiso 1 1 calc R . . H14A H 0.1063 0.4116 0.0756 0.050(14) Uiso 1 1 calc R . . H14B H 0.1606 0.3285 0.0160 0.035(12) Uiso 1 1 calc R . . C15 C 0.0648(6) 0.3507(3) 0.2925(4) 0.0470(13) Uani 1 1 d . . . H15 H 0.0063 0.4000 0.2766 0.058(15) Uiso 1 1 calc R . . H15A H 0.1552 0.3679 0.3307 0.056(15) Uiso 1 1 calc R . . H15B H 0.0213 0.3128 0.3469 0.050(14) Uiso 1 1 calc R . . H16 H 0.875(5) -0.025(3) 0.087(4) 0.043(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0106(2) 0.0126(2) 0.0148(2) 0.00003(15) 0.00100(14) -0.00057(16) C1 0.0169(19) 0.0174(18) 0.0155(16) 0.0023(13) 0.0008(13) 0.0022(15) C2 0.0157(19) 0.0173(18) 0.0169(16) -0.0004(13) -0.0003(13) 0.0021(15) C3 0.0157(18) 0.0163(18) 0.0140(15) -0.0021(13) 0.0011(13) -0.0013(14) C4 0.0181(19) 0.0151(17) 0.0136(15) 0.0024(14) 0.0002(13) -0.0013(15) C5 0.0159(18) 0.0154(18) 0.0150(15) -0.0006(14) 0.0003(13) -0.0004(15) C6 0.0135(19) 0.0169(18) 0.0181(16) -0.0006(14) 0.0028(13) -0.0023(15) C7 0.015(2) 0.0177(19) 0.0187(16) -0.0013(14) 0.0015(13) 0.0035(15) O1 0.0173(15) 0.0262(15) 0.0331(14) 0.0123(11) 0.0014(11) -0.0025(12) O2 0.0184(13) 0.0147(13) 0.0204(12) 0.0047(10) 0.0010(10) 0.0000(10) C8 0.0142(18) 0.0174(19) 0.0155(15) -0.0005(14) 0.0017(13) 0.0007(15) O3 0.0146(13) 0.0143(13) 0.0230(12) 0.0005(10) 0.0050(9) 0.0010(10) O4 0.0159(14) 0.0250(15) 0.0259(13) 0.0050(11) 0.0041(10) 0.0074(12) P1 0.0126(5) 0.0138(5) 0.0154(4) 0.0007(3) 0.0001(3) 0.0008(4) O5 0.0130(12) 0.0191(13) 0.0172(11) 0.0002(10) -0.0015(9) -0.0008(10) O6 0.0169(13) 0.0185(13) 0.0186(12) 0.0047(10) 0.0018(9) 0.0035(10) O7 0.0229(14) 0.0174(14) 0.0231(12) -0.0023(10) 0.0041(10) -0.0016(11) C9 0.034(2) 0.029(2) 0.0222(18) -0.0077(17) 0.0024(16) 0.0017(19) C10 0.085(5) 0.119(6) 0.050(3) -0.044(4) 0.007(3) -0.026(4) C13 0.072(4) 0.066(4) 0.046(3) 0.003(3) 0.025(3) 0.029(3) N1 0.027(2) 0.0207(19) 0.0335(18) 0.0049(14) -0.0051(15) 0.0066(17) C14 0.039(3) 0.028(2) 0.035(2) 0.0035(18) 0.0018(19) -0.004(2) C15 0.067(4) 0.039(3) 0.036(2) 0.007(2) 0.009(2) 0.015(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 Zn1 O2 1.950(2) . ? Zn1 O5 1.953(2) 4_565 ? Zn1 O3 1.953(2) 4_665 ? Zn1 O6 1.959(2) 2_655 ? C1 C2 1.388(5) . ? C1 C6 1.397(5) . ? C1 C7 1.505(5) . ? C2 C3 1.389(5) . ? C3 C4 1.395(5) . ? C3 C8 1.501(5) . ? C4 C5 1.398(5) . ? C5 C6 1.389(5) . ? C5 P1 1.799(3) . ? C7 O1 1.237(4) . ? C7 O2 1.280(4) . ? C8 O4 1.242(4) . ? C8 O3 1.277(4) . ? O3 Zn1 1.953(2) 4_566 ? P1 O6 1.492(2) . ? P1 O5 1.497(3) . ? P1 O7 1.585(2) . ? O5 Zn1 1.953(2) 4_666 ? O6 Zn1 1.959(2) 2_645 ? O7 C9 1.469(4) . ? C9 C10 1.496(7) . ? C9 C13 1.504(7) . ? N1 C15 1.471(6) . ? N1 C14 1.485(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zn1 O5 106.06(10) . 4_565 ? O2 Zn1 O3 123.83(10) . 4_665 ? O5 Zn1 O3 108.72(10) 4_565 4_665 ? O2 Zn1 O6 106.69(10) . 2_655 ? O5 Zn1 O6 106.69(10) 4_565 2_655 ? O3 Zn1 O6 103.78(10) 4_665 2_655 ? C2 C1 C6 119.3(3) . . ? C2 C1 C7 120.4(3) . . ? C6 C1 C7 120.2(3) . . ? C1 C2 C3 121.1(3) . . ? C2 C3 C4 119.1(3) . . ? C2 C3 C8 120.7(3) . . ? C4 C3 C8 120.1(3) . . ? C3 C4 C5 120.7(3) . . ? C6 C5 C4 119.2(3) . . ? C6 C5 P1 121.4(3) . . ? C4 C5 P1 119.4(3) . . ? C5 C6 C1 120.7(3) . . ? O1 C7 O2 124.3(3) . . ? O1 C7 C1 120.6(3) . . ? O2 C7 C1 115.1(3) . . ? C7 O2 Zn1 114.0(2) . . ? O4 C8 O3 124.6(3) . . ? O4 C8 C3 119.4(3) . . ? O3 C8 C3 116.0(3) . . ? C8 O3 Zn1 112.1(2) . 4_566 ? O6 P1 O5 118.71(13) . . ? O6 P1 O7 107.21(14) . . ? O5 P1 O7 109.57(14) . . ? O6 P1 C5 107.04(15) . . ? O5 P1 C5 107.21(15) . . ? O7 P1 C5 106.45(14) . . ? P1 O5 Zn1 132.69(14) . 4_666 ? P1 O6 Zn1 142.78(16) . 2_645 ? C9 O7 P1 120.0(2) . . ? O7 C9 C10 105.0(4) . . ? O7 C9 C13 108.9(3) . . ? C10 C9 C13 112.3(5) . . ? C15 N1 C14 113.2(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.113 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.114 # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 869669' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common (Zn2(H2pip)2(bpy))2(H2O) _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 N2 O16 P2 Zn2' _chemical_formula_weight 811.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1360(14) _cell_length_b 12.264(3) _cell_length_c 12.574(3) _cell_angle_alpha 69.555(3) _cell_angle_beta 79.414(3) _cell_angle_gamma 82.245(3) _cell_volume 727.3(3) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2430 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 28.12 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.852 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 1.844 _exptl_absorpt_correction_type 'multi-scan, numerical' _exptl_absorpt_correction_T_min 0.8368 _exptl_absorpt_correction_T_max 0.9640 _exptl_absorpt_process_details 'SADABS; Sheldrick, 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker TXS fine-focus rotating anode' _diffrn_radiation_monochromator 'Bruker Helios multilayered confocal mirror' _diffrn_measurement_device 'Bruker APEX-II CCD-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8164 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0872 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3259 _reflns_number_gt 2474 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)' _publ_section_references ; Wakita, K. (2001). Yadokari-XG. Software for Crystal Structure Analyses. Release of Software (Yadokari-XG 2009) for Crystal Structure Analyses, Kabuto, C., Akine, S., Nemoto, T. & Kwon, E. (2009). J. Cryst. Soc. Jpn., 51, 218-224. ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.3021P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3259 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.0976 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.26250(8) 0.14500(2) 0.47312(3) 0.01224(12) Uani 1 1 d . . . P1 P 0.83434(17) 0.09853(5) 0.34754(6) 0.01039(18) Uani 1 1 d . . . O1S O -0.4168(6) 0.0668(3) 0.7445(2) 0.0473(9) Uani 1 1 d . . . O1 O 0.1186(4) 0.11048(17) 0.35609(18) 0.0160(5) Uani 1 1 d . . . O2 O 0.2118(5) 0.03013(16) 0.62630(18) 0.0226(6) Uani 1 1 d . . . O3 O 0.6368(5) 0.15609(17) 0.42027(18) 0.0145(5) Uani 1 1 d . . . O4 O 0.1489(5) 0.41759(17) 0.10696(18) 0.0185(5) Uani 1 1 d . . . O5 O 0.2872(5) 0.44171(18) -0.07899(18) 0.0206(5) Uani 1 1 d . . . H5 H 0.1513 0.4855 -0.0867 0.031 Uiso 1 1 calc R . . O6 O 1.3123(6) 0.0960(3) -0.0652(2) 0.0453(8) Uani 1 1 d . . . H6 H 1.4075 0.0853 -0.1212 0.068 Uiso 1 1 calc R . . O7 O 1.1183(6) 0.2412(4) -0.1998(2) 0.0544(10) Uani 1 1 d . . . N1 N 0.0405(6) 0.29204(19) 0.4829(3) 0.0181(6) Uani 1 1 d . . . C3 C -0.3840(7) 0.4576(2) 0.4964(3) 0.0188(7) Uani 1 1 d . . . C6 C 0.7928(7) 0.1717(2) 0.1986(2) 0.0123(6) Uani 1 1 d . . . C7 C 0.5804(7) 0.2535(2) 0.1702(3) 0.0142(7) Uani 1 1 d . . . H7 H 0.4609 0.2712 0.2281 0.017 Uiso 1 1 calc R . . C8 C 0.5430(7) 0.3098(2) 0.0558(3) 0.0153(7) Uani 1 1 d . . . C9 C 0.3081(7) 0.3940(2) 0.0311(2) 0.0154(7) Uani 1 1 d . . . C10 C 0.7228(7) 0.2855(3) -0.0312(3) 0.0184(7) Uani 1 1 d . . . H10 H 0.6995 0.3233 -0.1074 0.022 Uiso 1 1 calc R . . C11 C 0.9394(7) 0.2040(3) -0.0037(3) 0.0192(7) Uani 1 1 d . . . C12 C 1.1307(8) 0.1829(4) -0.1000(3) 0.0343(10) Uani 1 1 d . . . C13 C 0.9713(7) 0.1469(2) 0.1104(3) 0.0156(7) Uani 1 1 d . . . H13 H 1.1133 0.0914 0.1283 0.019 Uiso 1 1 calc R . . C14 C -0.2749(14) 0.3881(5) 0.5828(5) 0.0125(11) Uiso 0.50 1 d P A 2 H14 H -0.3388 0.3928 0.6554 0.015 Uiso 0.50 1 calc PR A 2 C15 C -0.0656(14) 0.3065(5) 0.5714(6) 0.0134(12) Uiso 0.50 1 d P A 2 H15 H -0.0012 0.2586 0.6382 0.016 Uiso 0.50 1 calc PR A 2 C16 C -0.3623(13) 0.3464(5) 0.5995(5) 0.0096(11) Uiso 0.50 1 d P A 1 H16 H -0.4896 0.3312 0.6648 0.011 Uiso 0.50 1 calc PR A 1 C17 C 0.0046(14) 0.3875(5) 0.4061(6) 0.0113(11) Uiso 0.50 1 d P A 1 H17 H 0.1296 0.4036 0.3400 0.014 Uiso 0.50 1 calc PR A 1 C18 C -0.2019(15) 0.4720(5) 0.4089(6) 0.0146(13) Uiso 0.50 1 d P A 1 H18 H -0.2088 0.5405 0.3464 0.018 Uiso 0.50 1 calc PR A 1 C19 C -0.0472(14) 0.3706(5) 0.3753(6) 0.0133(12) Uiso 0.50 1 d P A 2 H19 H 0.0318 0.3628 0.3053 0.016 Uiso 0.50 1 calc PR A 2 C20 C -0.1424(13) 0.2695(5) 0.5903(5) 0.0082(11) Uiso 0.50 1 d P A 1 H20 H -0.1114 0.2034 0.6527 0.010 Uiso 0.50 1 calc PR A 1 C21 C -0.2486(14) 0.4560(5) 0.3799(6) 0.0113(12) Uiso 0.50 1 d P A 2 H21 H -0.2994 0.5110 0.3132 0.014 Uiso 0.50 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0105(2) 0.00908(14) 0.01061(19) 0.00121(12) 0.00338(15) 0.00246(12) P1 0.0117(5) 0.0094(3) 0.0073(4) -0.0012(3) 0.0026(3) -0.0010(3) O1S 0.0309(19) 0.094(2) 0.0262(16) -0.0414(16) -0.0158(14) 0.0371(17) O1 0.0064(13) 0.0205(9) 0.0134(11) 0.0024(8) -0.0008(9) 0.0027(8) O2 0.0462(18) 0.0130(8) 0.0056(10) -0.0012(8) 0.0062(11) -0.0107(10) O3 0.0092(13) 0.0232(9) 0.0117(11) -0.0081(8) -0.0013(9) 0.0021(9) O4 0.0220(15) 0.0191(9) 0.0100(11) 0.0012(8) -0.0051(10) 0.0004(9) O5 0.0254(16) 0.0243(10) 0.0071(11) 0.0021(8) -0.0058(10) -0.0004(10) O6 0.0195(17) 0.097(2) 0.0306(17) -0.0425(17) 0.0017(14) 0.0102(17) O7 0.0267(19) 0.126(3) 0.0176(16) -0.0362(18) 0.0050(14) -0.0080(19) N1 0.0073(15) 0.0129(10) 0.0356(17) -0.0106(11) -0.0014(13) -0.0006(10) C3 0.012(2) 0.0185(12) 0.033(2) -0.0184(13) -0.0078(15) 0.0055(13) C6 0.0128(18) 0.0133(10) 0.0096(15) -0.0021(10) 0.0014(13) -0.0052(11) C7 0.0185(19) 0.0113(10) 0.0110(15) -0.0024(11) 0.0030(13) -0.0056(11) C8 0.020(2) 0.0142(11) 0.0126(15) -0.0032(11) -0.0022(14) -0.0061(12) C9 0.024(2) 0.0149(11) 0.0052(14) 0.0022(10) -0.0034(14) -0.0076(12) C10 0.020(2) 0.0292(14) 0.0072(15) -0.0046(12) -0.0001(14) -0.0111(14) C11 0.016(2) 0.0307(14) 0.0149(16) -0.0131(13) 0.0054(14) -0.0093(14) C12 0.014(2) 0.080(3) 0.022(2) -0.034(2) 0.0047(17) -0.013(2) C13 0.0168(19) 0.0163(11) 0.0144(16) -0.0069(11) 0.0028(14) -0.0056(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.922(2) . ? Zn1 O2 1.944(2) . ? Zn1 O1 1.952(2) . ? Zn1 N1 2.029(2) . ? P1 O3 1.510(2) . ? P1 O1 1.514(2) 1_655 ? P1 O2 1.5374(19) 2_656 ? P1 C6 1.811(3) . ? O1 P1 1.514(2) 1_455 ? O2 P1 1.5374(19) 2_656 ? O4 C9 1.226(4) . ? O5 C9 1.320(3) . ? O6 C12 1.325(5) . ? O7 C12 1.216(5) . ? N1 C15 1.206(7) . ? N1 C17 1.247(6) . ? N1 C20 1.458(7) . ? N1 C19 1.469(7) . ? C3 C18 1.283(8) . ? C3 C14 1.292(7) . ? C3 C3 1.483(6) 2_466 ? C3 C21 1.507(7) . ? C3 C16 1.526(6) . ? C6 C7 1.386(4) . ? C6 C13 1.396(4) . ? C7 C8 1.397(4) . ? C8 C10 1.386(5) . ? C8 C9 1.482(5) . ? C10 C11 1.399(5) . ? C11 C13 1.389(5) . ? C11 C12 1.487(5) . ? C14 C15 1.390(9) . ? C16 C20 1.386(8) . ? C17 C18 1.384(9) . ? C19 C21 1.378(9) . ? 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 Zn1 O2 108.92(10) . . ? O3 Zn1 O1 105.85(9) . . ? O2 Zn1 O1 115.63(9) . . ? O3 Zn1 N1 117.69(9) . . ? O2 Zn1 N1 106.34(11) . . ? O1 Zn1 N1 102.69(10) . . ? O3 P1 O1 112.16(13) . 1_655 ? O3 P1 O2 112.89(13) . 2_656 ? O1 P1 O2 110.53(13) 1_655 2_656 ? O3 P1 C6 108.52(13) . . ? O1 P1 C6 106.49(14) 1_655 . ? O2 P1 C6 105.83(12) 2_656 . ? P1 O1 Zn1 129.96(14) 1_455 . ? P1 O2 Zn1 124.55(13) 2_656 . ? P1 O3 Zn1 132.78(13) . . ? C15 N1 C17 105.5(5) . . ? C15 N1 C20 23.6(3) . . ? C17 N1 C20 117.2(4) . . ? C15 N1 C19 118.2(4) . . ? C17 N1 C19 24.3(3) . . ? C20 N1 C19 120.0(4) . . ? C15 N1 Zn1 124.4(3) . . ? C17 N1 Zn1 129.8(4) . . ? C20 N1 Zn1 111.6(3) . . ? C19 N1 Zn1 115.6(3) . . ? C18 C3 C14 105.7(5) . . ? C18 C3 C3 124.0(5) . 2_466 ? C14 C3 C3 125.1(5) . 2_466 ? C18 C3 C21 21.7(4) . . ? C14 C3 C21 115.9(4) . . ? C3 C3 C21 118.9(4) 2_466 . ? C18 C3 C16 118.3(4) . . ? C14 C3 C16 26.2(3) . . ? C3 C3 C16 117.7(4) 2_466 . ? C21 C3 C16 118.5(3) . . ? C7 C6 C13 118.7(3) . . ? C7 C6 P1 120.1(2) . . ? C13 C6 P1 121.1(2) . . ? C6 C7 C8 121.0(3) . . ? C10 C8 C7 119.9(3) . . ? C10 C8 C9 121.6(3) . . ? C7 C8 C9 118.5(3) . . ? O4 C9 O5 123.3(3) . . ? O4 C9 C8 122.4(3) . . ? O5 C9 C8 114.3(3) . . ? C8 C10 C11 119.6(3) . . ? C13 C11 C10 119.9(3) . . ? C13 C11 C12 122.4(3) . . ? C10 C11 C12 117.7(3) . . ? O7 C12 O6 124.6(4) . . ? O7 C12 C11 122.3(4) . . ? O6 C12 C11 113.0(3) . . ? C11 C13 C6 120.8(3) . . ? C3 C14 C15 122.4(6) . . ? N1 C15 C14 126.1(6) . . ? C20 C16 C3 116.3(5) . . ? N1 C17 C18 126.7(6) . . ? C3 C18 C17 121.1(6) . . ? C21 C19 N1 118.7(5) . . ? C16 C20 N1 120.1(5) . . ? C19 C21 C3 118.0(5) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.617 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.116