# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 _publ_contact_author ; Sue-Lein Wang Department of Chemistry National Tsing Hua University 101, Section 2, Kuang-Fu Road Hsinchu, Taiwan 30013 R.O.C ; _publ_contact_author_email slwang@nthu.edu.tw _publ_contact_author_fax '(+886) 35711082' # TITLE AND AUTHOR LIST _publ_section_title ; Boosting Reused Value by Converting Trashed PET Bottle into Potent Organic Reactants for Luminescent Nanoporous Materials ; loop_ _publ_author_name _publ_author_address 'Yu-Ting Huang' ;Department of Chemistry National Tsing Hua University 101, Section 2, Kuang-Fu Road Hsinchu, Taiwan 30013 R.O.C ; 'Yu-Lun Lai' ;Green Energy and Environment Research Laboratories, Industrial Technology Research Institute, Hsinchu, Taiwan 300 R.O.C ; 'Chia-Her Lin' ;Department of Chemistry, Chung-Yuan Christian University, Chungli 320, Taiwan. ; 'Sue-Lein Wang' ;Department of Chemistry National Tsing Hua University 101, Section 2, Kuang-Fu Road Hsinchu, Taiwan 30013 R.O.C ; _publ_contact_author_name 'Sue-Lein Wang' #================================================================END data_NTHU-3-TAEG _database_code_depnum_ccdc_archive 'CCDC 768399' #TrackingRef '- Combine CIF.pdf' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H60 N8 O24 P4 Zn3' _chemical_formula_weight 1164.79 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 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 14.9192(14) _cell_length_b 8.4607(8) _cell_length_c 34.445(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.271(2) _cell_angle_gamma 90.00 _cell_volume 4248.5(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4299 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.31 _exptl_crystal_description Lamellar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.821 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2408 _exptl_absorpt_coefficient_mu 1.927 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.592 _exptl_absorpt_correction_T_max 0.925 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15337 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0521 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.35 _reflns_number_total 5299 _reflns_number_gt 4865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHEXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHEXTL' _computing_publication_material 'Bruker SHEXTL' _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^)+(0.0466P)^2^+39.0824P] 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 . _refine_ls_extinction_method none _refine_ls_extinction_coef 0.00074(16) _refine_ls_number_reflns 5299 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1446 _refine_ls_wR_factor_gt 0.1422 _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_restrained_S_all 1.210 _refine_ls_shift/su_max 0.004 _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 Zn1 Zn 0.63144(3) 0.42880(5) 0.242306(13) 0.00985(12) Uani 1 1 d . . . Zn2 Zn 0.5000 0.04101(7) 0.2500 0.01070(15) Uani 1 2 d S . . P1 P 0.32614(6) -0.20719(11) 0.24228(3) 0.0088(2) Uani 1 1 d . . . P2 P 0.46285(6) 0.28173(12) 0.19142(3) 0.0098(2) Uani 1 1 d . . . O1 O 0.39893(18) -0.1042(3) 0.22910(9) 0.0138(6) Uani 1 1 d . . . O2 O 0.33819(19) -0.3773(3) 0.22786(9) 0.0129(5) Uani 1 1 d . . . O3 O 0.23241(18) -0.1460(3) 0.21972(9) 0.0127(5) Uani 1 1 d . . . O4 O 0.33486(19) -0.2044(3) 0.28700(8) 0.0132(6) Uani 1 1 d . . . O5 O 0.39770(19) 0.2791(3) 0.22002(9) 0.0136(6) Uani 1 1 d . . . O6 O 0.52518(18) 0.4283(3) 0.19660(8) 0.0120(5) Uani 1 1 d . . . O7 O 0.52083(18) 0.1310(3) 0.19889(9) 0.0127(5) Uani 1 1 d . . . O8 O 0.40138(19) 0.2790(4) 0.14902(9) 0.0156(6) Uani 1 1 d . . . O9 O 0.3377(2) 0.4331(4) 0.06571(10) 0.0227(7) Uani 1 1 d . . . O10 O 0.4695(2) 0.3122(4) 0.09126(9) 0.0177(6) Uani 1 1 d . . . O11 O 0.2118(2) 0.6276(4) -0.05947(10) 0.0228(7) Uani 1 1 d . . . O12 O 0.1973(2) 0.5970(4) 0.02343(10) 0.0211(7) Uani 1 1 d . . . N1 N 0.4051(2) -0.1960(4) 0.38256(10) 0.0118(6) Uani 1 1 d . . . N2 N 0.3225(2) 0.0611(4) 0.33060(11) 0.0158(7) Uani 1 1 d . . . N3 N 0.2548(2) -0.3957(4) 0.33447(11) 0.0143(7) Uani 1 1 d . . . N4 N 0.5176(2) -0.2575(4) 0.32333(10) 0.0136(7) Uani 1 1 d . . . C1 C 0.4012(3) -0.0328(5) 0.39690(13) 0.0161(8) Uani 1 1 d . . . C2 C 0.3188(3) 0.0559(5) 0.37349(13) 0.0172(8) Uani 1 1 d . . . C3 C 0.3432(3) -0.3004(5) 0.39900(12) 0.0141(8) Uani 1 1 d . . . C4 C 0.3146(3) -0.4437(5) 0.37280(13) 0.0150(8) Uani 1 1 d . . . C5 C 0.4995(3) -0.2579(5) 0.39236(12) 0.0146(8) Uani 1 1 d . . . C6 C 0.5567(3) -0.2018(5) 0.36390(12) 0.0153(8) Uani 1 1 d . . . C7 C 0.4174(3) 0.3944(5) 0.06443(12) 0.0143(8) Uani 1 1 d . . . C8 C 0.4596(3) 0.4477(5) 0.03093(12) 0.0148(8) Uani 1 1 d . . . C9 C 0.5368(3) 0.3707(5) 0.02314(12) 0.0149(8) Uani 1 1 d . . . C10 C 0.4235(3) 0.5770(5) 0.00770(13) 0.0161(8) Uani 1 1 d . . . C11 C 0.1965(3) 0.4815(6) -0.04140(15) 0.0241(9) Uani 1 1 d . . . C12 C 0.1466(3) 0.5030(6) -0.00795(15) 0.0226(9) Uani 1 1 d . . . H11A H 0.2466 0.6903 -0.0412 0.080 Uiso 1 1 d . . . H12A H 0.2444 0.5295 0.0413 0.080 Uiso 1 1 d . . . H2C H 0.2782 0.1046 0.3188 0.080 Uiso 1 1 d . . . H4C H 0.5429 -0.2217 0.3046 0.080 Uiso 1 1 d . . . H1A H 0.4595 0.0154 0.3951 0.080 Uiso 1 1 d . . . H1B H 0.3944 -0.0197 0.4258 0.080 Uiso 1 1 d . . . H2D H 0.2660 0.0018 0.3771 0.080 Uiso 1 1 d . . . H2E H 0.3146 0.1604 0.3828 0.080 Uiso 1 1 d . . . H3D H 0.2840 -0.2310 0.4020 0.080 Uiso 1 1 d . . . H3E H 0.3738 -0.3378 0.4263 0.080 Uiso 1 1 d . . . H4D H 0.3713 -0.5030 0.3656 0.080 Uiso 1 1 d . . . H4E H 0.2810 -0.5132 0.3864 0.080 Uiso 1 1 d . . . H5B H 0.4965 -0.3696 0.3914 0.080 Uiso 1 1 d . . . H5C H 0.5333 -0.2370 0.4196 0.080 Uiso 1 1 d . . . H6A H 0.5587 -0.0919 0.3626 0.080 Uiso 1 1 d . . . H6B H 0.6160 -0.2395 0.3720 0.080 Uiso 1 1 d . . . H9A H 0.5661 0.2850 0.0392 0.080 Uiso 1 1 d . . . H10A H 0.3698 0.6350 0.0149 0.080 Uiso 1 1 d . . . H11B H 0.2557 0.4285 -0.0286 0.080 Uiso 1 1 d . . . H11C H 0.1580 0.4227 -0.0654 0.080 Uiso 1 1 d . . . H12B H 0.0869 0.5590 -0.0181 0.080 Uiso 1 1 d . . . H12C H 0.1335 0.4030 0.0047 0.080 Uiso 1 1 d . . . H10 H 0.4520 0.3081 0.1135 0.080 Uiso 1 1 d . . . H3A H 0.2812 -0.3328 0.3199 0.080 Uiso 1 1 d . . . H4A H 0.5187 -0.3509 0.3228 0.080 Uiso 1 1 d . . . H4B H 0.4641 -0.2284 0.3210 0.080 Uiso 1 1 d . . . H2B H 0.3277 -0.0358 0.3208 0.080 Uiso 1 1 d . . . H2A H 0.3737 0.1101 0.3259 0.080 Uiso 1 1 d . . . H3B H 0.2080 -0.3522 0.3394 0.080 Uiso 1 1 d . . . H3C H 0.2343 -0.4693 0.3203 0.080 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 0.0063(2) 0.0074(2) 0.0161(2) -0.00008(16) 0.00318(16) -0.00012(15) Zn2 0.0084(3) 0.0077(3) 0.0167(3) 0.000 0.0042(2) 0.000 P1 0.0050(4) 0.0080(4) 0.0139(5) 0.0001(3) 0.0028(3) 0.0000(3) P2 0.0070(4) 0.0084(4) 0.0144(5) 0.0001(3) 0.0031(3) -0.0003(3) O1 0.0087(12) 0.0122(13) 0.0218(15) -0.0028(11) 0.0063(11) -0.0051(10) O2 0.0138(13) 0.0080(13) 0.0177(14) -0.0007(10) 0.0052(11) 0.0010(10) O3 0.0066(12) 0.0119(13) 0.0200(14) 0.0013(11) 0.0036(10) 0.0034(10) O4 0.0097(12) 0.0134(14) 0.0162(14) 0.0002(11) 0.0023(10) -0.0022(10) O5 0.0129(13) 0.0118(14) 0.0181(14) -0.0006(11) 0.0076(11) -0.0029(10) O6 0.0078(12) 0.0103(13) 0.0176(14) 0.0016(10) 0.0018(10) -0.0011(10) O7 0.0103(12) 0.0088(13) 0.0199(14) 0.0016(11) 0.0052(11) 0.0017(10) O8 0.0119(13) 0.0187(15) 0.0156(14) 0.0022(11) 0.0013(11) -0.0018(11) O9 0.0145(14) 0.0293(18) 0.0262(17) 0.0097(14) 0.0087(12) 0.0032(13) O10 0.0162(14) 0.0189(15) 0.0190(15) 0.0051(12) 0.0063(12) 0.0032(12) O11 0.0228(16) 0.0217(17) 0.0234(16) 0.0002(13) 0.0037(13) 0.0001(13) O12 0.0191(15) 0.0186(16) 0.0251(17) 0.0009(13) 0.0038(12) 0.0028(12) N1 0.0087(14) 0.0107(16) 0.0163(16) 0.0010(12) 0.0034(12) 0.0004(12) N2 0.0137(16) 0.0129(16) 0.0213(18) 0.0029(13) 0.0046(13) 0.0039(13) N3 0.0113(15) 0.0121(16) 0.0197(17) -0.0013(13) 0.0037(13) -0.0021(12) N4 0.0077(14) 0.0151(16) 0.0190(17) -0.0007(13) 0.0048(12) -0.0009(12) C1 0.0178(19) 0.0132(19) 0.0177(19) 0.0002(15) 0.0045(16) -0.0009(15) C2 0.022(2) 0.0130(19) 0.018(2) 0.0005(15) 0.0070(16) 0.0039(15) C3 0.0144(18) 0.0132(18) 0.0152(18) 0.0014(15) 0.0041(15) -0.0026(14) C4 0.0141(18) 0.0107(18) 0.021(2) 0.0021(15) 0.0048(15) 0.0003(14) C5 0.0103(17) 0.0163(19) 0.0160(19) 0.0017(15) 0.0006(14) -0.0011(14) C6 0.0102(17) 0.0163(19) 0.0173(19) -0.0013(15) -0.0019(14) -0.0010(14) C7 0.0131(17) 0.0124(18) 0.0176(19) -0.0012(15) 0.0038(15) -0.0016(14) C8 0.0143(18) 0.0129(19) 0.0178(19) 0.0003(15) 0.0047(15) -0.0026(14) C9 0.0134(17) 0.0148(19) 0.0166(19) 0.0011(15) 0.0031(15) 0.0014(14) C10 0.0130(18) 0.0150(19) 0.020(2) 0.0009(16) 0.0038(15) 0.0014(15) C11 0.025(2) 0.020(2) 0.027(2) -0.0042(18) 0.0044(19) -0.0006(18) C12 0.017(2) 0.020(2) 0.030(2) 0.0008(18) 0.0023(18) -0.0008(17) _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 O5 1.928(3) 2_655 ? Zn1 O2 1.938(3) 2_665 ? Zn1 O3 1.943(3) 3 ? Zn1 O6 1.983(3) . ? Zn2 O1 1.960(3) 2_655 ? Zn2 O1 1.960(3) . ? Zn2 O7 2.002(3) 2_655 ? Zn2 O7 2.002(3) . ? Zn2 P2 2.8374(11) . ? Zn2 P2 2.8374(11) 2_655 ? P1 O4 1.518(3) . ? P1 O1 1.534(3) . ? P1 O3 1.538(3) . ? P1 O2 1.546(3) . ? P2 O5 1.524(3) . ? P2 O7 1.532(3) . ? P2 O6 1.538(3) . ? P2 O8 1.551(3) . ? O2 Zn1 1.938(3) 2_645 ? O3 Zn1 1.943(3) 3_445 ? O5 Zn1 1.928(3) 2_655 ? O9 C7 1.243(5) . ? O10 C7 1.279(5) . ? O10 H10 0.8612 . ? O11 C11 1.424(6) . ? O11 H11A 0.8985 . ? O12 C12 1.423(6) . ? O12 H12A 1.0067 . ? N1 C1 1.472(5) . ? N1 C5 1.473(5) . ? N1 C3 1.475(5) . ? N2 C2 1.491(6) . ? N2 H2C 0.7899 . ? N2 H2B 0.8962 . ? N2 H2A 0.9126 . ? N3 C4 1.484(5) . ? N3 H3A 0.8800 . ? N3 H3B 0.8372 . ? N3 H3C 0.8094 . ? N4 C6 1.473(5) . ? N4 H4C 0.8701 . ? N4 H4A 0.7913 . ? N4 H4B 0.8223 . ? C1 C2 1.518(6) . ? C1 H1A 0.9746 . ? C1 H1B 1.0270 . ? C2 H2D 0.9418 . ? C2 H2E 0.9476 . ? C3 C4 1.517(6) . ? C3 H3D 1.0835 . ? C3 H3E 1.0059 . ? C4 H4D 1.0577 . ? C4 H4E 0.9561 . ? C5 C6 1.508(6) . ? C5 H5B 0.9459 . ? C5 H5C 0.9820 . ? C6 H6A 0.9313 . ? C6 H6B 0.9254 . ? C7 C8 1.497(6) . ? C8 C10 1.395(6) . ? C8 C9 1.398(6) . ? C9 C10 1.394(6) 5_665 ? C9 H9A 0.9579 . ? C10 C9 1.394(6) 5_665 ? C10 H10A 1.0134 . ? C11 C12 1.510(7) . ? C11 H11B 1.0056 . ? C11 H11C 1.0290 . ? C12 H12B 1.0033 . ? C12 H12C 0.9892 . ? 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 Zn1 O2 105.07(12) 2_655 2_665 ? O5 Zn1 O3 111.11(12) 2_655 3 ? O2 Zn1 O3 111.99(12) 2_665 3 ? O5 Zn1 O6 106.05(12) 2_655 . ? O2 Zn1 O6 118.70(12) 2_665 . ? O3 Zn1 O6 103.81(12) 3 . ? O1 Zn2 O1 102.35(18) 2_655 . ? O1 Zn2 O7 99.58(12) 2_655 2_655 ? O1 Zn2 O7 108.08(12) . 2_655 ? O1 Zn2 O7 108.08(12) 2_655 . ? O1 Zn2 O7 99.58(12) . . ? O7 Zn2 O7 135.30(17) 2_655 . ? O1 Zn2 P2 136.89(9) 2_655 . ? O1 Zn2 P2 99.79(9) . . ? O7 Zn2 P2 108.00(9) 2_655 . ? O7 Zn2 P2 31.25(8) . . ? O1 Zn2 P2 99.79(9) 2_655 2_655 ? O1 Zn2 P2 136.89(9) . 2_655 ? O7 Zn2 P2 31.25(8) 2_655 2_655 ? O7 Zn2 P2 108.00(9) . 2_655 ? P2 Zn2 P2 88.26(4) . 2_655 ? O4 P1 O1 112.22(16) . . ? O4 P1 O3 112.35(16) . . ? O1 P1 O3 106.51(16) . . ? O4 P1 O2 110.46(16) . . ? O1 P1 O2 107.20(16) . . ? O3 P1 O2 107.83(16) . . ? O5 P2 O7 107.10(16) . . ? O5 P2 O6 112.95(16) . . ? O7 P2 O6 110.25(15) . . ? O5 P2 O8 106.12(16) . . ? O7 P2 O8 110.20(17) . . ? O6 P2 O8 110.09(16) . . ? O5 P2 Zn2 65.47(12) . . ? O7 P2 Zn2 42.69(11) . . ? O6 P2 Zn2 118.33(11) . . ? O8 P2 Zn2 130.23(12) . . ? P1 O1 Zn2 141.73(19) . . ? P1 O2 Zn1 130.39(18) . 2_645 ? P1 O3 Zn1 127.34(18) . 3_445 ? P2 O5 Zn1 133.73(18) . 2_655 ? P2 O6 Zn1 117.10(16) . . ? P2 O7 Zn2 106.06(15) . . ? C7 O10 H10 114.3 . . ? C11 O11 H11A 109.2 . . ? C12 O12 H12A 109.6 . . ? C1 N1 C5 111.1(3) . . ? C1 N1 C3 111.1(3) . . ? C5 N1 C3 110.2(3) . . ? C2 N2 H2C 108.6 . . ? C2 N2 H2B 111.7 . . ? H2C N2 H2B 111.3 . . ? C2 N2 H2A 113.4 . . ? H2C N2 H2A 109.8 . . ? H2B N2 H2A 102.0 . . ? C4 N3 H3A 114.6 . . ? C4 N3 H3B 108.1 . . ? H3A N3 H3B 110.0 . . ? C4 N3 H3C 113.9 . . ? H3A N3 H3C 106.2 . . ? H3B N3 H3C 103.6 . . ? C6 N4 H4C 116.5 . . ? C6 N4 H4A 109.6 . . ? H4C N4 H4A 108.5 . . ? C6 N4 H4B 100.3 . . ? H4C N4 H4B 112.9 . . ? H4A N4 H4B 108.7 . . ? N1 C1 C2 111.8(3) . . ? N1 C1 H1A 105.8 . . ? C2 C1 H1A 113.0 . . ? N1 C1 H1B 116.5 . . ? C2 C1 H1B 103.1 . . ? H1A C1 H1B 106.9 . . ? N2 C2 C1 110.2(3) . . ? N2 C2 H2D 110.6 . . ? C1 C2 H2D 107.2 . . ? N2 C2 H2E 109.1 . . ? C1 C2 H2E 112.7 . . ? H2D C2 H2E 106.9 . . ? N1 C3 C4 111.7(3) . . ? N1 C3 H3D 107.5 . . ? C4 C3 H3D 111.0 . . ? N1 C3 H3E 110.5 . . ? C4 C3 H3E 108.6 . . ? H3D C3 H3E 107.4 . . ? N3 C4 C3 110.5(3) . . ? N3 C4 H4D 106.3 . . ? C3 C4 H4D 112.4 . . ? N3 C4 H4E 108.9 . . ? C3 C4 H4E 108.1 . . ? H4D C4 H4E 110.6 . . ? N1 C5 C6 112.7(3) . . ? N1 C5 H5B 108.2 . . ? C6 C5 H5B 108.7 . . ? N1 C5 H5C 115.3 . . ? C6 C5 H5C 108.5 . . ? H5B C5 H5C 102.9 . . ? N4 C6 C5 110.5(3) . . ? N4 C6 H6A 106.5 . . ? C5 C6 H6A 111.9 . . ? N4 C6 H6B 109.6 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.7 . . ? O9 C7 O10 123.8(4) . . ? O9 C7 C8 120.7(4) . . ? O10 C7 C8 115.5(4) . . ? C10 C8 C9 119.3(4) . . ? C10 C8 C7 120.2(4) . . ? C9 C8 C7 120.4(4) . . ? C10 C9 C8 119.9(4) 5_665 . ? C10 C9 H9A 117.6 5_665 . ? C8 C9 H9A 122.3 . . ? C9 C10 C8 120.7(4) 5_665 . ? C9 C10 H10A 121.2 5_665 . ? C8 C10 H10A 118.0 . . ? O11 C11 C12 112.3(4) . . ? O11 C11 H11B 111.8 . . ? C12 C11 H11B 104.4 . . ? O11 C11 H11C 100.5 . . ? C12 C11 H11C 112.9 . . ? H11B C11 H11C 115.2 . . ? O12 C12 C11 112.2(4) . . ? O12 C12 H12B 106.9 . . ? C11 C12 H12B 109.6 . . ? O12 C12 H12C 105.5 . . ? C11 C12 H12C 114.1 . . ? H12B C12 H12C 108.3 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.507 _refine_diff_density_min -1.188 _refine_diff_density_rms 0.162 #================================================================END data_NTHU-3-TAH2O _database_code_depnum_ccdc_archive 'CCDC 768400' #TrackingRef '- Combine CIF.pdf' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H52 N8 O22 P4 Zn3' _chemical_formula_weight 1076.69 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 ? _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 15.0025(5) _cell_length_b 8.6854(3) _cell_length_c 30.5449(11) _cell_angle_alpha 90.00 _cell_angle_beta 97.1810(10) _cell_angle_gamma 90.00 _cell_volume 3948.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5845 _cell_measurement_theta_min 2.692 _cell_measurement_theta_max 28.26 _exptl_crystal_description lamellar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 2.062 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.903 _exptl_absorpt_correction_T_max 0.952 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19570 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4908 _reflns_number_gt 3207 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0203P)^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 . _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4908 _refine_ls_number_parameters 313 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0673 _refine_ls_wR_factor_gt 0.0623 _refine_ls_goodness_of_fit_ref 0.836 _refine_ls_restrained_S_all 0.839 _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 0.0000 0.28610(5) 0.2500 0.02290(13) Uani 1 2 d S . . Zn2 Zn 0.13585(2) 0.69567(4) 0.252537(11) 0.01858(9) Uani 1 1 d . . . P1 P 0.33723(5) 0.56019(8) 0.25848(2) 0.01680(17) Uani 1 1 d . . . P2 P 0.01503(5) 0.55561(9) 0.31462(2) 0.01958(18) Uani 1 1 d . . . O1 O 0.32496(14) 0.5660(2) 0.20837(6) 0.0272(5) Uani 1 1 d . . . O2 O 0.25398(13) 0.6226(2) 0.27771(6) 0.0244(5) Uani 1 1 d . . . O3 O 0.35249(14) 0.3944(2) 0.27529(6) 0.0260(5) Uani 1 1 d . . . O4 O 0.41822(13) 0.6572(2) 0.27834(7) 0.0254(5) Uani 1 1 d . . . O5 O 0.06727(13) 0.6975(2) 0.30311(6) 0.0242(5) Uani 1 1 d . . . O6 O -0.08374(13) 0.5664(2) 0.29630(6) 0.0259(5) Uani 1 1 d . . . O7 O 0.05703(14) 0.4091(2) 0.29937(7) 0.0310(5) Uani 1 1 d . . . O8 O 0.01824(18) 0.5436(3) 0.36563(7) 0.0532(8) Uani 1 1 d . . . O9 O 0.2123(4) 0.6744(6) 0.47746(16) 0.0505(15) Uani 0.499(2) 1 d P A 1 O10 O 0.1533(3) 0.5576(5) 0.41599(14) 0.0397(13) Uani 0.499(2) 1 d P A 1 H10A H 0.1020 0.5588 0.4031 0.060 Uiso 0.499(2) 1 calc PR A 1 C7 C 0.0651(3) 0.5365(5) 0.47342(12) 0.0448(10) Uani 0.499(2) 1 d PD A 1 C8 C 0.0272(5) 0.6521(8) 0.5027(3) 0.0402(19) Uani 0.499(2) 1 d PD . 1 C9 C 0.0401(8) 0.4033(16) 0.4742(3) 0.043(3) Uani 0.499(2) 1 d PD . 1 C10 C 0.1524(4) 0.5990(7) 0.4553(2) 0.0293(16) Uani 0.499(2) 1 d PD A 1 O9' O -0.0023(3) 0.7658(5) 0.40652(14) 0.0370(13) Uani 0.501(2) 1 d P A 2 H9'B H 0.0027 0.6747 0.4002 0.056 Uiso 0.501(2) 1 calc PR A 2 O10' O -0.0382(4) 0.8997(5) 0.46379(16) 0.0501(15) Uani 0.501(2) 1 d P A 2 C7' C -0.0065(5) 0.6353(8) 0.4744(2) 0.0261(16) Uani 0.501(2) 1 d P A 2 C8' C 0.0651(3) 0.5365(5) 0.47342(12) 0.0448(10) Uani 0.501(2) 1 d P . 2 C9' C -0.0622(8) 0.6108(14) 0.5065(3) 0.029(2) Uani 0.501(2) 1 d P . 2 C10' C -0.0161(4) 0.7775(7) 0.4464(2) 0.0290(16) Uani 0.501(2) 1 d P A 2 O1W O -0.1101(4) 1.0556(7) 0.46014(18) 0.0703(19) Uani 0.499(2) 1 d P A 1 O1W' O 0.2939(5) 0.5579(7) 0.4666(2) 0.087(2) Uani 0.501(2) 1 d P A 2 N1 N 0.2847(2) 0.5713(3) 0.10273(8) 0.0344(7) Uani 1 1 d . . . N2 N 0.26495(19) 0.8287(3) 0.16302(9) 0.0335(7) Uani 1 1 d . . . N3 N 0.46089(18) 0.5021(3) 0.15839(9) 0.0359(7) Uani 1 1 d . . . N4 N 0.20086(17) 0.3691(3) 0.16378(8) 0.0277(6) Uani 1 1 d . . . C1 C 0.2641(4) 0.7309(4) 0.08818(12) 0.0702(16) Uani 1 1 d . . . C2 C 0.2123(3) 0.8168(4) 0.11969(12) 0.0585(13) Uani 1 1 d . . . C3 C 0.3664(3) 0.5160(4) 0.08645(11) 0.0475(10) Uani 1 1 d . . . C4 C 0.4511(3) 0.5719(5) 0.11451(13) 0.0594(12) Uani 1 1 d . . . C5 C 0.2081(2) 0.4696(4) 0.08896(10) 0.0376(9) Uani 1 1 d . . . C6 C 0.2076(2) 0.3281(4) 0.11737(11) 0.0356(9) Uani 1 1 d . . . H9A H 0.0677 0.3306 0.4577 0.078 Uiso 0.50 1 d P . . H8'A H 0.1148 0.5656 0.4599 -0.002 Uiso 0.50 1 d P . . H9'A H -0.0986 0.6875 0.5148 0.040 Uiso 0.50 1 d P . . H2NA H 0.2329 0.8771 0.1815 0.065 Uiso 1 1 d . . . H2NB H 0.3149 0.8823 0.1608 0.097 Uiso 1 1 d . . . H2NC H 0.2795 0.7352 0.1734 0.063 Uiso 1 1 d . . . H3NA H 0.5091 0.5413 0.1747 0.080 Uiso 1 1 d . . . H3NB H 0.4678 0.4006 0.1561 0.100 Uiso 1 1 d . . . H3NC H 0.4123 0.5215 0.1714 0.048 Uiso 1 1 d . . . H4NA H 0.2036 0.2841 0.1802 0.053 Uiso 1 1 d . . . H4NB H 0.1488 0.4167 0.1655 0.050 Uiso 1 1 d . . . H4NC H 0.2459 0.4315 0.1738 0.046 Uiso 1 1 d . . . H1A H 0.2295 0.7296 0.0592 0.070 Uiso 1 1 d . . . H1B H 0.3199 0.7854 0.0858 0.095 Uiso 1 1 d . . . H2A H 0.1974 0.9190 0.1082 0.078 Uiso 1 1 d . . . H2B H 0.1565 0.7628 0.1224 0.077 Uiso 1 1 d . . . H3A H 0.3673 0.5504 0.0563 0.045 Uiso 1 1 d . . . H3B H 0.3662 0.4039 0.0862 0.034 Uiso 1 1 d . . . H4A H 0.5033 0.5462 0.1000 0.101 Uiso 1 1 d . . . H4B H 0.4489 0.6828 0.1173 0.078 Uiso 1 1 d . . . H5A H 0.2098 0.4384 0.0586 0.061 Uiso 1 1 d . . . H5B H 0.1527 0.5263 0.0902 0.041 Uiso 1 1 d . . . H6A H 0.1573 0.2631 0.1063 0.073 Uiso 1 1 d . . . H6B H 0.2625 0.2702 0.1159 0.045 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 0.0152(3) 0.0144(3) 0.0390(3) 0.000 0.0029(2) 0.000 Zn2 0.01461(18) 0.01513(17) 0.02662(19) -0.00072(15) 0.00506(14) -0.00090(14) P1 0.0141(4) 0.0141(4) 0.0225(4) -0.0015(3) 0.0036(3) -0.0002(3) P2 0.0178(4) 0.0186(4) 0.0224(4) 0.0020(3) 0.0028(3) -0.0013(3) O1 0.0281(13) 0.0299(12) 0.0240(12) -0.0022(9) 0.0045(10) -0.0006(10) O2 0.0132(11) 0.0299(12) 0.0306(12) -0.0032(9) 0.0040(9) 0.0067(9) O3 0.0320(13) 0.0142(10) 0.0336(13) -0.0001(9) 0.0105(10) 0.0037(9) O4 0.0167(12) 0.0242(12) 0.0347(12) -0.0016(9) 0.0008(10) -0.0088(9) O5 0.0247(12) 0.0171(10) 0.0334(12) -0.0058(9) 0.0138(10) -0.0052(9) O6 0.0161(12) 0.0243(11) 0.0370(13) 0.0096(10) 0.0013(10) -0.0011(9) O7 0.0207(12) 0.0188(11) 0.0512(15) -0.0073(10) -0.0042(11) 0.0038(9) O8 0.069(2) 0.0663(18) 0.0233(13) 0.0105(12) 0.0027(13) -0.0234(15) O9 0.040(3) 0.068(4) 0.044(3) -0.010(3) 0.005(3) -0.020(3) O10 0.028(3) 0.063(3) 0.028(3) 0.000(2) 0.002(2) -0.004(2) C7 0.034(2) 0.054(3) 0.051(2) 0.022(2) 0.0240(19) 0.012(2) C8 0.040(5) 0.032(4) 0.055(6) -0.001(4) 0.029(4) 0.003(4) C9 0.043(7) 0.045(6) 0.048(7) -0.013(7) 0.027(6) 0.001(5) C10 0.025(4) 0.033(4) 0.032(4) 0.008(3) 0.014(3) 0.005(3) O9' 0.058(4) 0.026(3) 0.028(3) 0.0034(19) 0.010(2) -0.005(2) O10' 0.065(4) 0.040(3) 0.047(3) -0.004(2) 0.016(3) 0.003(3) C7' 0.028(4) 0.035(4) 0.015(3) -0.003(3) 0.001(3) -0.002(3) C8' 0.034(2) 0.054(3) 0.051(2) 0.022(2) 0.0240(19) 0.012(2) C9' 0.034(6) 0.031(4) 0.024(5) 0.003(5) 0.010(4) 0.010(4) C10' 0.024(4) 0.035(4) 0.028(4) -0.001(3) 0.002(3) -0.005(3) O1W 0.058(4) 0.092(5) 0.059(4) -0.022(3) 0.005(3) -0.004(4) O1W' 0.094(6) 0.089(5) 0.075(5) -0.032(4) 0.000(4) -0.001(4) N1 0.052(2) 0.0266(15) 0.0259(15) -0.0010(12) 0.0113(14) -0.0043(14) N2 0.0377(18) 0.0260(15) 0.0384(17) -0.0077(12) 0.0106(14) 0.0041(13) N3 0.0215(16) 0.0372(17) 0.0500(19) -0.0117(14) 0.0087(14) -0.0054(12) N4 0.0281(16) 0.0215(14) 0.0346(16) 0.0025(12) 0.0076(13) -0.0026(12) C1 0.152(5) 0.033(2) 0.027(2) 0.0082(17) 0.016(3) 0.004(3) C2 0.103(4) 0.036(2) 0.033(2) 0.0019(18) -0.006(2) 0.027(2) C3 0.057(3) 0.056(3) 0.033(2) -0.0124(18) 0.020(2) -0.020(2) C4 0.051(3) 0.092(3) 0.039(2) -0.018(2) 0.021(2) -0.037(2) C5 0.041(2) 0.046(2) 0.0254(18) 0.0018(16) 0.0021(16) 0.0087(18) C6 0.040(2) 0.034(2) 0.033(2) -0.0104(16) 0.0089(17) -0.0091(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 1.943(2) 3_445 ? Zn1 O4 1.943(2) 4_545 ? Zn1 O7 1.956(2) 2 ? Zn1 O7 1.956(2) . ? Zn2 O3 1.9416(19) 4 ? Zn2 O2 1.9478(19) . ? Zn2 O6 1.9506(19) 2 ? Zn2 O5 1.960(2) . ? P1 O1 1.519(2) . ? P1 O3 1.5362(19) . ? P1 O4 1.5394(19) . ? P1 O2 1.544(2) . ? P2 O7 1.519(2) . ? P2 O6 1.520(2) . ? P2 O5 1.525(2) . ? P2 O8 1.556(2) . ? O3 Zn2 1.9415(19) 4_545 ? O4 Zn1 1.943(2) 3 ? O6 Zn2 1.9505(19) 2 ? O9 C10 1.242(8) . ? O10 C10 1.256(7) . ? O10 H10A 0.8200 . ? C7 C9 1.217(14) . ? C7 C8 1.503(8) . ? C7 C10 1.579(7) . ? C7 H8'A 0.9319 . ? C8 C9 1.388(15) 5_566 ? C9 C8 1.388(15) 5_566 ? C9 H9A 0.9365 . ? C10 H8'A 0.6634 . ? O9' C10' 1.266(7) . ? O9' H9'B 0.8200 . ? O10' C10' 1.250(7) . ? C7' C9' 1.382(13) . ? C7' C10' 1.498(9) . ? C9' C8' 1.422(12) 5_566 ? C9' H9'A 0.9179 . ? N1 C3 1.461(5) . ? N1 C5 1.469(4) . ? N1 C1 1.477(4) . ? N2 C2 1.458(4) . ? N2 H2NA 0.8917 . ? N2 H2NB 0.8922 . ? N2 H2NC 0.8886 . ? N3 C4 1.462(5) . ? N3 H3NA 0.8928 . ? N3 H3NB 0.8917 . ? N3 H3NC 0.8882 . ? N4 C6 1.477(4) . ? N4 H4NA 0.8903 . ? N4 H4NB 0.8913 . ? N4 H4NC 0.8900 . ? C1 C2 1.508(6) . ? C1 H1A 0.9687 . ? C1 H1B 0.9725 . ? C2 H2A 0.9695 . ? C2 H2B 0.9712 . ? C3 C4 1.521(5) . ? C3 H3A 0.9708 . ? C3 H3B 0.9736 . ? C4 H4A 0.9728 . ? C4 H4B 0.9679 . ? C5 C6 1.505(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9698 . ? C6 H6A 0.9686 . ? C6 H6B 0.9708 . ? 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 O4 109.60(12) 3_445 4_545 ? O4 Zn1 O7 114.75(8) 3_445 2 ? O4 Zn1 O7 102.18(9) 4_545 2 ? O4 Zn1 O7 102.18(9) 3_445 . ? O4 Zn1 O7 114.75(8) 4_545 . ? O7 Zn1 O7 113.79(12) 2 . ? O3 Zn2 O2 109.58(9) 4 . ? O3 Zn2 O6 103.07(8) 4 2 ? O2 Zn2 O6 111.87(8) . 2 ? O3 Zn2 O5 115.01(8) 4 . ? O2 Zn2 O5 103.46(8) . . ? O6 Zn2 O5 114.06(8) 2 . ? O1 P1 O3 111.22(11) . . ? O1 P1 O4 111.67(12) . . ? O3 P1 O4 107.67(11) . . ? O1 P1 O2 111.72(11) . . ? O3 P1 O2 107.22(12) . . ? O4 P1 O2 107.10(11) . . ? O7 P2 O6 111.21(12) . . ? O7 P2 O5 111.20(12) . . ? O6 P2 O5 111.76(11) . . ? O7 P2 O8 106.79(14) . . ? O6 P2 O8 106.22(13) . . ? O5 P2 O8 109.40(12) . . ? P1 O2 Zn2 134.73(12) . . ? P1 O3 Zn2 134.80(13) . 4_545 ? P1 O4 Zn1 130.62(12) . 3 ? P2 O5 Zn2 120.71(11) . . ? P2 O6 Zn2 126.60(12) . 2 ? P2 O7 Zn1 122.40(12) . . ? C10 O10 H10A 109.5 . . ? C9 C7 C8 118.8(7) . . ? C9 C7 C10 127.2(7) . . ? C8 C7 C10 111.7(5) . . ? C9 C7 H8'A 122.2 . . ? C8 C7 H8'A 117.8 . . ? C10 C7 H8'A 6.9 . . ? C9 C8 C7 115.1(7) 5_566 . ? C7 C9 C8 125.9(10) . 5_566 ? C7 C9 H9A 118.1 . . ? C8 C9 H9A 116.0 5_566 . ? O9 C10 O10 125.3(6) . . ? O9 C10 C7 124.4(6) . . ? O10 C10 C7 110.2(5) . . ? O9 C10 H8'A 133.8 . . ? O10 C10 H8'A 100.7 . . ? C7 C10 H8'A 9.6 . . ? C10' O9' H9'B 109.5 . . ? C9' C7' C10' 120.5(7) . . ? C7' C9' C8' 120.0(9) . 5_566 ? C7' C9' H9'A 121.3 . . ? C8' C9' H9'A 118.8 5_566 . ? O10' C10' O9' 124.1(6) . . ? O10' C10' C7' 118.1(6) . . ? O9' C10' C7' 117.8(6) . . ? C3 N1 C5 111.4(3) . . ? C3 N1 C1 111.1(3) . . ? C5 N1 C1 110.5(3) . . ? C2 N2 H2NA 109.6 . . ? C2 N2 H2NB 109.5 . . ? H2NA N2 H2NB 109.1 . . ? C2 N2 H2NC 109.8 . . ? H2NA N2 H2NC 109.4 . . ? H2NB N2 H2NC 109.4 . . ? C4 N3 H3NA 109.5 . . ? C4 N3 H3NB 109.7 . . ? H3NA N3 H3NB 109.1 . . ? C4 N3 H3NC 109.7 . . ? H3NA N3 H3NC 109.4 . . ? H3NB N3 H3NC 109.5 . . ? C6 N4 H4NA 109.6 . . ? C6 N4 H4NB 109.5 . . ? H4NA N4 H4NB 109.3 . . ? C6 N4 H4NC 109.6 . . ? H4NA N4 H4NC 109.4 . . ? H4NB N4 H4NC 109.4 . . ? N1 C1 C2 112.2(3) . . ? N1 C1 H1A 109.4 . . ? C2 C1 H1A 109.2 . . ? N1 C1 H1B 109.2 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.8 . . ? N2 C2 C1 110.5(3) . . ? N2 C2 H2A 109.7 . . ? C1 C2 H2A 109.7 . . ? N2 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.1 . . ? N1 C3 C4 112.4(3) . . ? N1 C3 H3A 109.4 . . ? C4 C3 H3A 109.1 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.5 . . ? N3 C4 C3 111.4(3) . . ? N3 C4 H4A 109.3 . . ? C3 C4 H4A 109.4 . . ? N3 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 107.9 . . ? N1 C5 C6 112.7(3) . . ? N1 C5 H5A 109.1 . . ? C6 C5 H5A 109.0 . . ? N1 C5 H5B 109.1 . . ? C6 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N4 C6 C5 111.2(3) . . ? N4 C6 H6A 109.4 . . ? C5 C6 H6A 109.5 . . ? N4 C6 H6B 109.3 . . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.600 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.084 #================================================================END data_2 _database_code_depnum_ccdc_archive 'CCDC 804562' #TrackingRef '- Combine CIF.pdf' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O12 P2 Zn2' _chemical_formula_weight 687.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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 9.9740(5) _cell_length_b 9.1804(5) _cell_length_c 27.5385(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2521.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4851 _cell_measurement_theta_min 2.339 _cell_measurement_theta_max 26.192 _exptl_crystal_description lamellar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.810 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 2.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6790 _exptl_absorpt_correction_T_max 0.7869 _exptl_absorpt_process_details 'SADABS (Bruker, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25732 _diffrn_reflns_av_R_equivalents 0.1036 _diffrn_reflns_av_sigmaI/netI 0.1018 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.43 _reflns_number_total 6271 _reflns_number_gt 4151 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 (Bruker, 2007)' _computing_cell_refinement 'Bruker SAINT (Bruker, 2007)' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 2007)' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0400P)^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 constr _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 0.575(17) _refine_ls_number_reflns 6271 _refine_ls_number_parameters 353 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1146 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 0.62128(7) 0.32750(7) 0.05796(2) 0.02012(16) Uani 1 1 d . . . Zn2 Zn 0.43416(7) 0.67979(7) -0.03946(2) 0.02122(17) Uani 1 1 d . . . P1 P 0.72228(16) 0.57882(18) -0.01527(6) 0.0198(4) Uani 1 1 d . . . P2 P 0.32699(15) 0.41845(19) 0.03494(6) 0.0211(4) Uani 1 1 d . . . O1 O 0.6216(4) 0.6998(4) -0.02519(16) 0.0239(11) Uani 1 1 d . . . O2 O 0.6992(4) 0.5025(4) 0.03279(15) 0.0304(11) Uani 1 1 d . . . O3 O 0.3648(4) 0.8662(5) -0.01594(16) 0.0262(10) Uani 1 1 d . . . O4 O 0.7069(4) 0.4594(5) -0.05581(16) 0.0341(12) Uani 1 1 d . . . H4A H 0.6647 0.4933 -0.0788 0.051 Uiso 1 1 calc R . . O5 O 0.4383(4) 0.3056(4) 0.04014(19) 0.0328(13) Uani 1 1 d . . . O6 O 0.6914(4) 0.1487(4) 0.02861(15) 0.0261(10) Uani 1 1 d . . . O7 O 0.3496(5) 0.5213(5) -0.00686(18) 0.0407(13) Uani 1 1 d . . . O8 O 0.3247(5) 0.5130(5) 0.08314(17) 0.0392(12) Uani 1 1 d . . . H8A H 0.3126 0.4595 0.1066 0.059 Uiso 1 1 calc R . . O9 O 0.6323(5) 0.3605(5) 0.12794(17) 0.0400(13) Uani 1 1 d . . . O10 O 0.3941(5) 0.6550(6) -0.10787(18) 0.0434(14) Uani 1 1 d . . . O11 O 0.7798(6) 0.1966(6) 0.1526(2) 0.0591(16) Uani 1 1 d . . . O12 O 0.5762(6) 0.5415(6) -0.13492(18) 0.0560(16) Uani 1 1 d . . . N1 N 0.5250(6) 0.1131(7) -0.4226(2) 0.0399(15) Uani 1 1 d . . . H1A H 0.5580 0.1071 -0.4514 0.048 Uiso 1 1 calc R . . N2 N 0.5725(8) 0.1047(10) -0.0614(3) 0.062(2) Uani 1 1 d . . . H2A H 0.6128 0.1007 -0.0338 0.074 Uiso 1 1 calc R . . C1 C 0.6955(7) 0.2953(8) 0.1601(2) 0.0329(17) Uani 1 1 d . . . C2 C 0.6632(7) 0.3349(8) 0.2121(2) 0.0334(17) Uani 1 1 d . . . C3 C 0.7297(8) 0.2706(8) 0.2501(3) 0.045(2) Uani 1 1 d . . . H3A H 0.8004 0.2076 0.2435 0.054 Uiso 1 1 calc R . . C4 C 0.6947(8) 0.2966(8) 0.2974(3) 0.045(2) Uani 1 1 d . . . H4B H 0.7445 0.2558 0.3226 0.054 Uiso 1 1 calc R . . C5 C 0.5859(7) 0.3834(8) 0.3077(2) 0.0294(16) Uani 1 1 d . . . C6 C 0.5184(7) 0.4519(8) 0.2698(2) 0.0357(17) Uani 1 1 d . . . H6A H 0.4470 0.5139 0.2765 0.043 Uiso 1 1 calc R . . C7 C 0.5576(6) 0.4279(8) 0.2227(2) 0.0340(17) Uani 1 1 d . . . H7A H 0.5126 0.4746 0.1975 0.041 Uiso 1 1 calc R . . C8 C 0.4661(7) 0.6011(8) -0.1411(2) 0.0336(16) Uani 1 1 d . . . C9 C 0.5448(8) 0.0018(9) -0.3914(3) 0.042(2) Uani 1 1 d . . . H9A H 0.5951 -0.0788 -0.4008 0.051 Uiso 1 1 calc R . . C10 C 0.4916(7) 0.0082(8) -0.3468(3) 0.0419(19) Uani 1 1 d . . . H10A H 0.5053 -0.0682 -0.3252 0.050 Uiso 1 1 calc R . . C11 C 0.4138(7) 0.1315(9) -0.3322(3) 0.0385(19) Uani 1 1 d . . . C12 C 0.4008(7) 0.2407(9) -0.3655(3) 0.0396(19) Uani 1 1 d . . . H12A H 0.3528 0.3241 -0.3574 0.047 Uiso 1 1 calc R . . C13 C 0.4576(8) 0.2292(8) -0.4107(3) 0.0415(19) Uani 1 1 d . . . H13A H 0.4479 0.3047 -0.4329 0.050 Uiso 1 1 calc R . . C14 C 0.3467(9) 0.1347(10) -0.2835(3) 0.056(2) Uani 1 1 d . . . H14A H 0.2804 0.0576 -0.2824 0.067 Uiso 1 1 calc R . . H14B H 0.2996 0.2266 -0.2801 0.067 Uiso 1 1 calc R . . C15 C 0.4399(8) 0.1172(8) -0.2408(3) 0.048(2) Uani 1 1 d . . . H15A H 0.5075 0.1931 -0.2415 0.057 Uiso 1 1 calc R . . H15B H 0.4850 0.0238 -0.2428 0.057 Uiso 1 1 calc R . . C16 C 0.3607(9) 0.1262(9) -0.1930(3) 0.054(2) Uani 1 1 d . . . H16A H 0.3107 0.2169 -0.1930 0.065 Uiso 1 1 calc R . . H16B H 0.2959 0.0475 -0.1927 0.065 Uiso 1 1 calc R . . C17 C 0.4389(8) 0.1191(8) -0.1474(3) 0.0372(18) Uani 1 1 d . . . C18 C 0.5262(9) 0.0035(10) -0.1366(3) 0.058(2) Uani 1 1 d . . . H18A H 0.5383 -0.0704 -0.1593 0.069 Uiso 1 1 calc R . . C19 C 0.5939(9) -0.0028(11) -0.0936(4) 0.063(3) Uani 1 1 d . . . H19A H 0.6527 -0.0788 -0.0868 0.076 Uiso 1 1 calc R . . C20 C 0.4931(11) 0.2150(14) -0.0700(4) 0.077(3) Uani 1 1 d . . . H20A H 0.4836 0.2888 -0.0471 0.092 Uiso 1 1 calc R . . C21 C 0.4248(9) 0.2215(11) -0.1125(3) 0.053(2) Uani 1 1 d . . . H21A H 0.3664 0.2988 -0.1179 0.063 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 Zn1 0.0209(4) 0.0245(4) 0.0150(3) 0.0016(4) 0.0004(3) 0.0012(3) Zn2 0.0219(4) 0.0270(4) 0.0148(3) 0.0011(4) 0.0007(3) 0.0012(3) P1 0.0181(9) 0.0224(9) 0.0189(8) 0.0022(7) -0.0014(7) -0.0002(7) P2 0.0162(8) 0.0259(9) 0.0213(9) 0.0035(7) 0.0013(7) -0.0005(7) O1 0.025(3) 0.015(2) 0.031(3) 0.0033(19) -0.0033(17) 0.0059(17) O2 0.035(3) 0.029(3) 0.026(2) 0.010(2) 0.003(2) -0.010(2) O3 0.014(2) 0.035(3) 0.030(3) -0.010(2) 0.0050(19) -0.0008(19) O4 0.040(3) 0.033(3) 0.029(3) -0.010(2) -0.013(2) 0.005(2) O5 0.042(3) 0.027(3) 0.029(3) 0.005(2) 0.023(2) 0.013(2) O6 0.017(2) 0.038(3) 0.023(2) -0.008(2) -0.0012(18) 0.001(2) O7 0.040(3) 0.038(3) 0.044(3) 0.020(2) 0.003(2) -0.007(2) O8 0.049(3) 0.035(3) 0.033(3) -0.014(2) 0.003(2) -0.004(2) O9 0.057(4) 0.052(3) 0.011(3) -0.002(2) -0.003(2) -0.001(3) O10 0.046(3) 0.067(4) 0.018(3) 0.000(2) 0.006(2) 0.001(3) O11 0.066(4) 0.077(4) 0.034(3) -0.013(3) 0.003(3) 0.029(3) O12 0.064(4) 0.078(4) 0.026(3) -0.009(3) -0.012(3) 0.023(3) N1 0.047(4) 0.056(4) 0.017(3) 0.003(3) 0.007(3) -0.005(3) N2 0.057(5) 0.100(7) 0.029(4) 0.011(5) -0.011(4) -0.037(5) C1 0.031(4) 0.054(5) 0.014(3) 0.002(3) 0.003(3) -0.007(4) C2 0.035(4) 0.046(5) 0.020(3) -0.003(3) 0.004(3) 0.001(4) C3 0.049(6) 0.059(5) 0.028(5) -0.001(4) 0.004(3) 0.019(4) C4 0.041(5) 0.067(6) 0.027(4) 0.010(4) -0.006(3) 0.010(4) C5 0.033(4) 0.045(4) 0.010(3) -0.004(3) 0.002(3) -0.002(3) C6 0.037(5) 0.050(4) 0.020(4) 0.000(3) -0.005(3) 0.007(3) C7 0.034(4) 0.050(5) 0.018(3) 0.012(3) 0.002(3) 0.001(3) C8 0.037(4) 0.043(4) 0.020(4) -0.003(3) -0.004(3) -0.002(4) C9 0.041(5) 0.040(5) 0.046(5) -0.013(4) 0.006(4) 0.008(4) C10 0.043(5) 0.043(5) 0.039(5) 0.013(4) 0.000(3) 0.005(4) C11 0.036(4) 0.050(5) 0.029(4) -0.009(4) 0.001(3) -0.001(3) C12 0.052(5) 0.028(4) 0.039(5) 0.000(4) -0.007(4) 0.009(4) C13 0.060(5) 0.035(4) 0.030(4) 0.010(3) 0.005(4) -0.003(4) C14 0.062(6) 0.080(6) 0.024(4) -0.003(4) 0.007(4) 0.009(5) C15 0.065(7) 0.058(4) 0.020(3) -0.003(5) 0.005(4) -0.002(4) C16 0.070(6) 0.069(6) 0.024(4) 0.003(4) 0.001(4) 0.020(5) C17 0.050(5) 0.038(5) 0.023(4) 0.001(4) -0.002(3) -0.007(4) C18 0.075(7) 0.051(5) 0.047(5) -0.015(4) -0.022(5) 0.007(5) C19 0.047(6) 0.056(6) 0.087(8) 0.026(6) -0.018(5) -0.003(5) C20 0.072(7) 0.119(10) 0.039(6) -0.039(6) 0.007(5) -0.034(7) C21 0.050(5) 0.063(6) 0.045(6) 0.000(5) 0.002(4) 0.001(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 Zn1 O2 1.915(4) . ? Zn1 O5 1.900(5) . ? Zn1 O9 1.954(5) . ? Zn1 O6 1.959(4) . ? Zn2 O7 1.906(4) . ? Zn2 O1 1.919(4) . ? Zn2 O10 1.939(5) . ? Zn2 O3 1.956(4) . ? P1 O3 1.509(4) 3_565 ? P1 O2 1.515(4) . ? P1 O1 1.522(4) . ? P1 O4 1.572(4) . ? P2 O6 1.497(4) 3_455 ? P2 O7 1.506(5) . ? P2 O5 1.525(5) . ? P2 O8 1.586(5) . ? O3 P1 1.509(4) 3_465 ? O4 H4A 0.8200 . ? O6 P2 1.497(4) 3 ? O8 H8A 0.8200 . ? O9 C1 1.241(8) . ? O10 C8 1.263(8) . ? O11 C1 1.253(8) . ? O12 C8 1.239(8) . ? N1 C13 1.303(9) . ? N1 C9 1.351(9) . ? N1 H1A 0.8600 . ? N2 C20 1.307(14) . ? N2 C19 1.344(12) . ? N2 H2A 0.8600 . ? C1 C2 1.512(9) . ? C2 C3 1.371(10) . ? C2 C7 1.387(9) . ? C3 C4 1.371(10) . ? C3 H3A 0.9300 . ? C4 C5 1.376(10) . ? C4 H4B 0.9300 . ? C5 C6 1.391(9) . ? C5 C8 1.510(9) 2_665 ? C6 C7 1.374(10) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C5 1.510(9) 2_664 ? C9 C10 1.338(11) . ? C9 H9A 0.9300 . ? C10 C11 1.431(10) . ? C10 H10A 0.9300 . ? C11 C12 1.364(11) . ? C11 C14 1.500(10) . ? C12 C13 1.371(11) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.507(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.537(11) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.479(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C21 1.351(12) . ? C17 C18 1.405(11) . ? C18 C19 1.366(13) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C20 C21 1.357(14) . ? C20 H20A 0.9300 . ? C21 H21A 0.9300 . ? 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 112.62(19) . . ? O2 Zn1 O9 101.8(2) . . ? O5 Zn1 O9 109.0(2) . . ? O2 Zn1 O6 114.14(18) . . ? O5 Zn1 O6 98.49(18) . . ? O9 Zn1 O6 121.11(19) . . ? O7 Zn2 O1 114.07(19) . . ? O7 Zn2 O10 106.1(2) . . ? O1 Zn2 O10 114.3(2) . . ? O7 Zn2 O3 110.8(2) . . ? O1 Zn2 O3 101.11(17) . . ? O10 Zn2 O3 110.6(2) . . ? O3 P1 O2 108.0(2) 3_565 . ? O3 P1 O1 112.0(2) 3_565 . ? O2 P1 O1 113.2(3) . . ? O3 P1 O4 108.5(3) 3_565 . ? O2 P1 O4 106.4(3) . . ? O1 P1 O4 108.5(3) . . ? O6 P2 O7 107.7(3) 3_455 . ? O6 P2 O5 112.9(3) 3_455 . ? O7 P2 O5 112.9(3) . . ? O6 P2 O8 108.1(3) 3_455 . ? O7 P2 O8 107.4(3) . . ? O5 P2 O8 107.7(3) . . ? P1 O1 Zn2 127.5(3) . . ? P1 O2 Zn1 140.0(3) . . ? P1 O3 Zn2 129.1(3) 3_465 . ? P1 O4 H4A 109.5 . . ? P2 O5 Zn1 130.7(3) . . ? P2 O6 Zn1 128.3(3) 3 . ? P2 O7 Zn2 154.8(3) . . ? P2 O8 H8A 109.5 . . ? C1 O9 Zn1 131.2(5) . . ? C8 O10 Zn2 129.2(5) . . ? C13 N1 C9 122.2(6) . . ? C13 N1 H1A 118.9 . . ? C9 N1 H1A 118.9 . . ? C20 N2 C19 123.0(8) . . ? C20 N2 H2A 118.5 . . ? C19 N2 H2A 118.5 . . ? O9 C1 O11 124.7(6) . . ? O9 C1 C2 116.9(6) . . ? O11 C1 C2 118.3(6) . . ? C3 C2 C7 118.2(6) . . ? C3 C2 C1 121.0(6) . . ? C7 C2 C1 120.6(6) . . ? C4 C3 C2 121.8(7) . . ? C4 C3 H3A 119.1 . . ? C2 C3 H3A 119.1 . . ? C3 C4 C5 119.7(7) . . ? C3 C4 H4B 120.1 . . ? C5 C4 H4B 120.1 . . ? C4 C5 C6 119.4(6) . . ? C4 C5 C8 121.1(6) . 2_665 ? C6 C5 C8 119.4(6) . 2_665 ? C7 C6 C5 119.9(6) . . ? C7 C6 H6A 120.1 . . ? C5 C6 H6A 120.1 . . ? C6 C7 C2 120.8(6) . . ? C6 C7 H7A 119.6 . . ? C2 C7 H7A 119.6 . . ? O12 C8 O10 125.3(6) . . ? O12 C8 C5 118.3(6) . 2_664 ? O10 C8 C5 116.4(6) . 2_664 ? C10 C9 N1 119.6(7) . . ? C10 C9 H9A 120.2 . . ? N1 C9 H9A 120.2 . . ? C9 C10 C11 120.6(7) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C12 C11 C10 116.3(7) . . ? C12 C11 C14 123.0(7) . . ? C10 C11 C14 120.6(7) . . ? C13 C12 C11 120.9(7) . . ? C13 C12 H12A 119.5 . . ? C11 C12 H12A 119.5 . . ? N1 C13 C12 120.4(7) . . ? N1 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C11 C14 C15 114.9(7) . . ? C11 C14 H14A 108.6 . . ? C15 C14 H14A 108.6 . . ? C11 C14 H14B 108.6 . . ? C15 C14 H14B 108.6 . . ? H14A C14 H14B 107.5 . . ? C14 C15 C16 110.2(7) . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C15 116.9(7) . . ? C17 C16 H16A 108.1 . . ? C15 C16 H16A 108.1 . . ? C17 C16 H16B 108.1 . . ? C15 C16 H16B 108.1 . . ? H16A C16 H16B 107.3 . . ? C21 C17 C18 116.1(8) . . ? C21 C17 C16 121.2(8) . . ? C18 C17 C16 122.7(7) . . ? C19 C18 C17 121.5(9) . . ? C19 C18 H18A 119.3 . . ? C17 C18 H18A 119.3 . . ? N2 C19 C18 117.6(9) . . ? N2 C19 H19A 121.2 . . ? C18 C19 H19A 121.2 . . ? N2 C20 C21 119.7(9) . . ? N2 C20 H20A 120.2 . . ? C21 C20 H20A 120.2 . . ? C17 C21 C20 122.1(10) . . ? C17 C21 H21A 118.9 . . ? C20 C21 H21A 118.9 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.43 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.449 _refine_diff_density_min -0.752 _refine_diff_density_rms 0.121 #================================================================END data_1 _database_code_depnum_ccdc_archive 'CCDC 823953' #TrackingRef '- Combine CIF.pdf' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O12 P2 Zn2' _chemical_formula_weight 687.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 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 27.6213(12) _cell_length_b 9.1189(4) _cell_length_c 9.9954(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.2110(10) _cell_angle_gamma 90.00 _cell_volume 2515.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6964 _cell_measurement_theta_min 2.352 _cell_measurement_theta_max 28.235 _exptl_crystal_description block _exptl_crystal_colour Brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.814 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 2.103 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_process_details . _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18089 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 0.74 _diffrn_reflns_theta_max 28.29 _reflns_number_total 6213 _reflns_number_gt 4980 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SHELXTL' _computing_data_reduction 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0379P)^2^+9.0829P] 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 . _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6213 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1324 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.191 _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 0.049544(16) 0.32200(5) 0.09595(5) 0.02128(13) Uani 1 1 d . . . Zn2 Zn 0.451647(17) 0.32169(6) 0.08788(5) 0.02737(14) Uani 1 1 d . . . P1 P 0.02663(4) 0.41946(12) -0.19539(11) 0.0217(2) Uani 1 1 d . . . P2 P 0.47664(4) 0.42296(14) -0.19868(11) 0.0273(2) Uani 1 1 d . . . O1 O 0.03338(12) 0.2971(3) -0.0949(3) 0.0292(7) Uani 1 1 d . . . O2 O 0.02171(11) 0.1428(4) 0.1621(3) 0.0271(7) Uani 1 1 d . . . O3 O 0.01638(12) 0.4852(4) 0.1718(3) 0.0374(8) Uani 1 1 d . . . O4 O 0.07394(13) 0.5189(4) -0.1868(4) 0.0394(8) Uani 1 1 d . . . O5 O 0.46738(12) 0.3029(4) -0.0988(3) 0.0321(7) Uani 1 1 d . . . O6 O 0.47525(12) 0.4990(4) 0.1737(4) 0.0381(8) Uani 1 1 d . . . O7 O 0.43551(13) 0.5414(4) -0.1887(4) 0.0448(9) Uani 1 1 d . . . O8 O 0.47657(12) 0.1374(4) 0.1593(3) 0.0346(8) Uani 1 1 d . . . O10 O 0.11821(11) 0.3668(4) 0.1196(4) 0.0408(8) Uani 1 1 d . . . O11 O 0.14355(13) 0.1944(5) 0.2643(4) 0.0541(11) Uani 1 1 d . . . O12 O 0.35655(14) 0.4599(6) -0.0658(5) 0.0593(12) Uani 1 1 d . . . O13 O 0.38197(12) 0.3340(4) 0.1155(4) 0.0433(9) Uani 1 1 d . . . C1 C 0.20219(16) 0.3348(6) 0.1545(5) 0.0317(10) Uani 1 1 d . . . C2 C 0.24007(18) 0.2662(7) 0.2268(6) 0.0439(13) Uani 1 1 d . . . C3 C 0.21277(17) 0.4294(6) 0.0513(5) 0.0363(11) Uani 1 1 d . . . C4 C 0.28789(17) 0.2906(7) 0.1932(6) 0.0446(13) Uani 1 1 d . . . C5 C 0.26060(17) 0.4527(6) 0.0181(5) 0.0367(11) Uani 1 1 d . . . C6 C 0.29827(15) 0.3807(6) 0.0869(5) 0.0328(10) Uani 1 1 d . . . C7 C 0.34974(17) 0.3944(6) 0.0394(5) 0.0372(11) Uani 1 1 d . . . C8 C 0.08036(18) 0.7356(6) 0.5313(6) 0.0411(12) Uani 1 1 d . . . C9 C 0.12569(18) 0.7445(6) 0.5912(6) 0.0415(12) Uani 1 1 d . . . C10 C 0.15859(16) 0.6329(6) 0.5754(5) 0.0356(11) Uani 1 1 d . . . C11 C 0.0987(2) 0.5058(6) 0.4385(6) 0.0415(12) Uani 1 1 d . . . C12 C 0.14487(19) 0.5141(6) 0.4963(6) 0.0415(12) Uani 1 1 d . . . C13 C 0.20727(19) 0.6385(8) 0.6490(6) 0.0512(15) Uani 1 1 d . . . C14 C 0.25075(18) 0.6183(7) 0.5602(6) 0.0451(13) Uani 1 1 d . . . C15 C 0.29784(18) 0.6339(8) 0.6418(6) 0.0516(15) Uani 1 1 d . . . C16 C 0.34330(17) 0.6186(6) 0.5645(5) 0.0387(12) Uani 1 1 d . . . C17 C 0.3810(2) 0.7174(8) 0.5845(7) 0.0559(16) Uani 1 1 d . . . C18 C 0.3504(2) 0.5027(7) 0.4778(7) 0.0549(16) Uani 1 1 d . . . C19 C 0.4226(2) 0.7011(11) 0.5188(7) 0.071(2) Uani 1 1 d . . . C20 C 0.3933(3) 0.4872(9) 0.4130(8) 0.072(2) Uani 1 1 d . . . C21 C 0.15037(16) 0.2953(6) 0.1840(5) 0.0354(11) Uani 1 1 d . . . N1 N 0.06783(14) 0.6173(5) 0.4566(4) 0.0389(10) Uani 1 1 d . . . N2 N 0.42837(18) 0.5892(8) 0.4371(6) 0.0674(19) Uani 1 1 d . . . H11A H 0.0804 0.4211 0.3844 0.080 Uiso 1 1 d . . . H5A H 0.2688 0.5219 -0.0626 0.080 Uiso 1 1 d . . . H12A H 0.1679 0.4386 0.4824 0.080 Uiso 1 1 d . . . H8A H 0.0564 0.8122 0.5199 0.080 Uiso 1 1 d . . . H18A H 0.3285 0.4293 0.4804 0.080 Uiso 1 1 d . . . H3A H 0.1895 0.4896 0.0042 0.080 Uiso 1 1 d . . . H14A H 0.2484 0.5325 0.4910 0.080 Uiso 1 1 d . . . H2A H 0.2336 0.2117 0.2989 0.080 Uiso 1 1 d . . . H13A H 0.2116 0.7442 0.6938 0.080 Uiso 1 1 d . . . H4A H 0.3148 0.2332 0.2405 0.080 Uiso 1 1 d . . . H17A H 0.3695 0.8258 0.5835 0.080 Uiso 1 1 d . . . H15A H 0.2999 0.7140 0.6984 0.080 Uiso 1 1 d . . . H19A H 0.4569 0.7245 0.5205 0.080 Uiso 1 1 d . . . H13B H 0.2121 0.5724 0.7229 0.080 Uiso 1 1 d . . . H15B H 0.3004 0.5486 0.7210 0.080 Uiso 1 1 d . . . H9A H 0.1294 0.8283 0.6492 0.080 Uiso 1 1 d . . . H14B H 0.2521 0.7088 0.4943 0.080 Uiso 1 1 d . . . H1 H 0.0389 0.6152 0.4148 0.080 Uiso 1 1 d . . . H2 H 0.4541 0.5796 0.3694 0.080 Uiso 1 1 d . . . H4C H 0.0990 0.4509 -0.1761 0.050 Uiso 1 1 d . . . H7C H 0.4203 0.5313 -0.1226 0.050 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 0.0170(2) 0.0253(2) 0.0217(2) 0.00098(19) 0.00205(17) 0.00139(18) Zn2 0.0182(2) 0.0401(3) 0.0239(3) 0.0008(2) 0.00220(19) -0.0011(2) P1 0.0222(5) 0.0237(5) 0.0192(5) -0.0016(4) 0.0018(4) 0.0033(4) P2 0.0221(5) 0.0384(6) 0.0217(5) -0.0012(5) 0.0032(4) -0.0045(5) O1 0.0376(17) 0.0304(17) 0.0194(14) -0.0014(12) -0.0028(12) 0.0063(13) O2 0.0276(15) 0.0353(17) 0.0183(14) 0.0037(12) -0.0011(12) -0.0075(13) O3 0.0385(19) 0.0390(19) 0.0348(18) -0.0077(15) 0.0019(15) 0.0188(15) O4 0.0365(19) 0.0385(19) 0.043(2) 0.0007(16) 0.0003(16) -0.0114(15) O5 0.0304(16) 0.042(2) 0.0242(16) 0.0009(14) 0.0072(13) -0.0007(14) O6 0.0278(17) 0.049(2) 0.0377(19) -0.0106(16) 0.0029(14) -0.0120(15) O7 0.038(2) 0.052(2) 0.045(2) 0.0146(18) 0.0151(17) 0.0102(17) O8 0.0340(18) 0.051(2) 0.0193(15) 0.0002(14) 0.0004(13) 0.0111(15) O10 0.0166(15) 0.052(2) 0.054(2) -0.0006(18) 0.0004(15) 0.0005(14) O11 0.0289(19) 0.076(3) 0.058(3) 0.023(2) 0.0063(17) -0.0083(19) O12 0.0285(19) 0.086(3) 0.064(3) 0.021(3) 0.0161(19) 0.003(2) O13 0.0165(15) 0.066(3) 0.048(2) -0.0008(19) 0.0012(14) 0.0005(15) C1 0.019(2) 0.044(3) 0.032(2) -0.002(2) 0.0016(17) -0.0031(18) C2 0.026(2) 0.057(3) 0.049(3) 0.016(3) 0.005(2) -0.002(2) C3 0.025(2) 0.045(3) 0.039(3) 0.004(2) 0.0063(19) 0.006(2) C4 0.019(2) 0.062(4) 0.052(3) 0.012(3) -0.001(2) 0.000(2) C5 0.027(2) 0.047(3) 0.036(3) 0.007(2) 0.005(2) -0.001(2) C6 0.0162(19) 0.045(3) 0.038(3) -0.005(2) 0.0021(18) -0.0049(18) C7 0.021(2) 0.046(3) 0.045(3) -0.007(2) 0.007(2) -0.005(2) C8 0.030(2) 0.043(3) 0.051(3) 0.008(3) 0.007(2) 0.010(2) C9 0.030(2) 0.044(3) 0.050(3) -0.003(3) 0.005(2) 0.000(2) C10 0.021(2) 0.049(3) 0.037(3) -0.001(2) 0.0051(19) 0.001(2) C11 0.040(3) 0.044(3) 0.040(3) 0.001(2) 0.001(2) -0.005(2) C12 0.032(3) 0.047(3) 0.045(3) 0.003(2) 0.000(2) 0.007(2) C13 0.023(2) 0.083(4) 0.047(3) -0.008(3) 0.002(2) 0.004(3) C14 0.024(2) 0.065(4) 0.047(3) -0.001(3) 0.004(2) 0.001(2) C15 0.022(2) 0.084(5) 0.049(3) -0.016(3) 0.007(2) 0.001(3) C16 0.022(2) 0.057(3) 0.038(3) 0.007(2) 0.0040(19) 0.001(2) C17 0.044(3) 0.066(4) 0.057(4) 0.007(3) -0.004(3) -0.011(3) C18 0.045(3) 0.057(4) 0.063(4) -0.004(3) 0.021(3) -0.005(3) C19 0.030(3) 0.127(7) 0.055(4) 0.027(5) 0.000(3) -0.021(4) C20 0.064(5) 0.086(5) 0.068(5) 0.009(4) 0.034(4) 0.020(4) C21 0.021(2) 0.050(3) 0.037(3) -0.007(2) 0.0069(18) 0.000(2) N1 0.025(2) 0.056(3) 0.035(2) 0.008(2) -0.0017(17) 0.0014(19) N2 0.028(2) 0.121(6) 0.055(3) 0.042(4) 0.019(2) 0.018(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 O3 1.919(3) . ? Zn1 O2 1.933(3) . ? Zn1 O10 1.946(3) . ? Zn1 O1 1.955(3) . ? Zn2 O6 1.932(3) . ? Zn2 O5 1.940(3) . ? Zn2 O8 1.941(4) . ? Zn2 O13 1.958(3) . ? P1 O3 1.498(3) 3_565 ? P1 O1 1.508(3) . ? P1 O2 1.535(3) 4_565 ? P1 O4 1.590(3) . ? P2 O5 1.510(3) . ? P2 O6 1.520(3) 3_665 ? P2 O8 1.522(3) 4_565 ? P2 O7 1.573(4) . ? O2 P1 1.535(3) 4_566 ? O3 P1 1.498(3) 3_565 ? O4 H4C 0.9324 . ? O6 P2 1.520(3) 3_665 ? O7 H7C 0.8015 . ? O8 P2 1.522(3) 4_566 ? O10 C21 1.259(6) . ? O11 C21 1.240(6) . ? O12 C7 1.230(7) . ? O13 C7 1.273(6) . ? C1 C3 1.384(7) . ? C1 C2 1.397(7) . ? C1 C21 1.516(6) . ? C2 C4 1.393(7) . ? C2 H2A 0.8991 . ? C3 C5 1.391(6) . ? C3 H3A 0.9556 . ? C4 C6 1.381(8) . ? C4 H4A 1.0115 . ? C5 C6 1.390(7) . ? C5 H5A 1.0553 . ? C6 C7 1.521(6) . ? C8 N1 1.349(7) . ? C8 C9 1.369(7) . ? C8 H8A 0.9661 . ? C9 C10 1.378(7) . ? C9 H9A 0.9622 . ? C10 C12 1.386(8) . ? C10 C13 1.509(7) . ? C11 N1 1.345(7) . ? C11 C12 1.381(7) . ? C11 H11A 1.0602 . ? C12 H12A 0.9513 . ? C13 C14 1.532(7) . ? C13 H13A 1.0675 . ? C13 H13B 0.9582 . ? C14 C15 1.515(7) . ? C14 H14A 1.0447 . ? C14 H14B 1.0579 . ? C15 C16 1.506(7) . ? C15 H15A 0.9244 . ? C15 H15B 1.1102 . ? C16 C17 1.385(8) . ? C16 C18 1.385(8) . ? C17 C19 1.353(10) . ? C17 H17A 1.0383 . ? C18 C20 1.378(8) . ? C18 H18A 0.9035 . ? C19 N2 1.321(11) . ? C19 H19A 0.9719 . ? C20 N2 1.358(11) . ? N1 H1 0.8866 . ? N2 H2 1.0035 . ? 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 108.56(15) . . ? O3 Zn1 O10 105.49(16) . . ? O2 Zn1 O10 122.31(15) . . ? O3 Zn1 O1 112.40(14) . . ? O2 Zn1 O1 99.01(13) . . ? O10 Zn1 O1 109.14(15) . . ? O6 Zn2 O5 114.62(15) . . ? O6 Zn2 O8 116.89(15) . . ? O5 Zn2 O8 100.85(14) . . ? O6 Zn2 O13 101.89(16) . . ? O5 Zn2 O13 113.48(15) . . ? O8 Zn2 O13 109.54(16) . . ? O3 P1 O1 113.8(2) 3_565 . ? O3 P1 O2 108.56(19) 3_565 4_565 ? O1 P1 O2 110.41(18) . 4_565 ? O3 P1 O4 108.4(2) 3_565 . ? O1 P1 O4 107.80(19) . . ? O2 P1 O4 107.72(19) 4_565 . ? O5 P2 O6 113.6(2) . 3_665 ? O5 P2 O8 111.1(2) . 4_565 ? O6 P2 O8 107.00(19) 3_665 4_565 ? O5 P2 O7 108.32(19) . . ? O6 P2 O7 107.3(2) 3_665 . ? O8 P2 O7 109.4(2) 4_565 . ? P1 O1 Zn1 125.56(19) . . ? P1 O2 Zn1 127.45(18) 4_566 . ? P1 O3 Zn1 154.9(2) 3_565 . ? P1 O4 H4C 103.4 . . ? P2 O5 Zn2 128.5(2) . . ? P2 O6 Zn2 138.0(2) 3_665 . ? P2 O7 H7C 112.1 . . ? P2 O8 Zn2 130.1(2) 4_566 . ? C21 O10 Zn1 128.2(4) . . ? C7 O13 Zn2 127.5(3) . . ? C3 C1 C2 119.3(4) . . ? C3 C1 C21 121.4(4) . . ? C2 C1 C21 119.1(5) . . ? C4 C2 C1 120.1(5) . . ? C4 C2 H2A 120.1 . . ? C1 C2 H2A 119.6 . . ? C1 C3 C5 120.2(5) . . ? C1 C3 H3A 124.6 . . ? C5 C3 H3A 114.9 . . ? C6 C4 C2 120.5(5) . . ? C6 C4 H4A 119.8 . . ? C2 C4 H4A 119.4 . . ? C6 C5 C3 120.6(5) . . ? C6 C5 H5A 118.8 . . ? C3 C5 H5A 120.5 . . ? C4 C6 C5 119.2(4) . . ? C4 C6 C7 120.9(5) . . ? C5 C6 C7 119.8(5) . . ? O12 C7 O13 126.4(5) . . ? O12 C7 C6 118.9(5) . . ? O13 C7 C6 114.7(5) . . ? N1 C8 C9 120.0(5) . . ? N1 C8 H8A 110.7 . . ? C9 C8 H8A 128.3 . . ? C8 C9 C10 120.1(5) . . ? C8 C9 H9A 112.6 . . ? C10 C9 H9A 126.9 . . ? C9 C10 C12 118.4(5) . . ? C9 C10 C13 119.9(5) . . ? C12 C10 C13 121.6(5) . . ? N1 C11 C12 118.9(5) . . ? N1 C11 H11A 109.0 . . ? C12 C11 H11A 132.0 . . ? C11 C12 C10 120.6(5) . . ? C11 C12 H12A 120.7 . . ? C10 C12 H12A 118.7 . . ? C10 C13 C14 114.7(5) . . ? C10 C13 H13A 108.5 . . ? C14 C13 H13A 105.9 . . ? C10 C13 H13B 116.7 . . ? C14 C13 H13B 106.4 . . ? H13A C13 H13B 103.6 . . ? C15 C14 C13 110.7(5) . . ? C15 C14 H14A 117.2 . . ? C13 C14 H14A 116.4 . . ? C15 C14 H14B 102.2 . . ? C13 C14 H14B 108.3 . . ? H14A C14 H14B 100.0 . . ? C16 C15 C14 115.5(5) . . ? C16 C15 H15A 110.8 . . ? C14 C15 H15A 115.8 . . ? C16 C15 H15B 105.6 . . ? C14 C15 H15B 110.3 . . ? H15A C15 H15B 96.7 . . ? C17 C16 C18 117.6(5) . . ? C17 C16 C15 120.1(6) . . ? C18 C16 C15 122.2(5) . . ? C19 C17 C16 120.4(7) . . ? C19 C17 H17A 111.3 . . ? C16 C17 H17A 113.0 . . ? C20 C18 C16 121.1(6) . . ? C20 C18 H18A 121.7 . . ? C16 C18 H18A 115.8 . . ? N2 C19 C17 120.7(7) . . ? N2 C19 H19A 92.2 . . ? C17 C19 H19A 144.5 . . ? N2 C20 C18 117.8(7) . . ? O11 C21 O10 126.4(5) . . ? O11 C21 C1 118.1(5) . . ? O10 C21 C1 115.5(5) . . ? C11 N1 C8 121.9(4) . . ? C11 N1 H1 119.0 . . ? C8 N1 H1 119.0 . . ? C19 N2 C20 122.4(5) . . ? C19 N2 H2 126.1 . . ? C20 N2 H2 109.9 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.630 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.105 #================================================================END data_3 _database_code_depnum_ccdc_archive 'CCDC 823954' #TrackingRef '- Combine CIF.pdf' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H34 N2 O12 P2 Zn2' _chemical_formula_weight 699.18 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 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 10.8928(2) _cell_length_b 8.79170(10) _cell_length_c 27.7665(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.0510(10) _cell_angle_gamma 90.00 _cell_volume 2609.79(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8095 _cell_measurement_theta_min 2.434 _cell_measurement_theta_max 28.276 _exptl_crystal_description lamellar _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.779 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 2.028 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6311 _exptl_absorpt_correction_T_max 0.8229 _exptl_absorpt_process_details . _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 24229 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.38 _reflns_number_total 6482 _reflns_number_gt 4962 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX 2' _computing_cell_refinement 'Bruker APEX 2' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0329P)^2^+2.6287P] 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 . _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6482 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.62956(3) -0.96692(4) -0.199058(11) 0.01716(9) Uani 1 1 d . . . Zn2 Zn 0.87284(3) -0.76219(4) -0.295995(11) 0.01644(9) Uani 1 1 d . . . P1 P 0.88172(7) -1.04710(8) -0.23217(3) 0.01599(16) Uani 1 1 d . . . P2 P 0.61328(7) -0.69500(8) -0.27101(3) 0.01604(16) Uani 1 1 d . . . O1 O 0.8878(2) -0.9796(2) -0.28177(7) 0.0249(5) Uani 1 1 d . . . O2 O 0.95466(18) -1.1955(2) -0.22300(8) 0.0224(4) Uani 1 1 d . . . O3 O 0.74679(18) -1.0796(2) -0.22810(8) 0.0238(5) Uani 1 1 d . . . O4 O 0.9396(2) -0.9247(2) -0.19322(7) 0.0278(5) Uani 1 1 d . . . O5 O 0.75207(18) -0.6523(2) -0.26639(7) 0.0206(4) Uani 1 1 d . . . O6 O 0.5880(2) -0.7607(2) -0.22339(7) 0.0229(5) Uani 1 1 d . . . O8 O 0.5844(2) -0.8247(2) -0.31067(7) 0.0267(5) Uani 1 1 d . . . O9 O 0.6680(2) -0.9354(3) -0.12854(8) 0.0341(6) Uani 1 1 d . . . O10 O 0.8365(2) -0.7622(3) 0.13210(8) 0.0351(6) Uani 1 1 d . . . O11 O 0.8769(2) -0.9420(3) -0.10832(8) 0.0439(7) Uani 1 1 d . . . O12 O 0.6284(2) -0.7848(3) 0.11091(8) 0.0432(7) Uani 1 1 d . . . N1 N 0.8225(2) -0.4519(3) -0.19068(9) 0.0252(6) Uani 1 1 d . . . N2 N 0.6137(3) -0.3218(3) 0.17196(10) 0.0353(7) Uani 1 1 d . . . C1 C 0.7042(3) -0.3977(4) -0.17658(12) 0.0276(7) Uani 1 1 d . . . C2 C 0.8884(3) -0.5653(4) -0.15522(12) 0.0327(8) Uani 1 1 d . . . C3 C 0.7310(3) -0.3314(4) -0.12548(12) 0.0288(7) Uani 1 1 d . . . C4 C 0.9137(3) -0.5022(5) -0.10349(12) 0.0376(8) Uani 1 1 d . . . C5 C 0.7960(3) -0.4446(4) -0.08754(11) 0.0301(7) Uani 1 1 d . . . C6 C 0.8308(3) -0.3783(5) -0.03566(12) 0.0450(10) Uani 1 1 d . . . C7 C 0.7253(3) -0.3470(4) -0.00833(12) 0.0363(8) Uani 1 1 d . . . C8 C 0.7822(3) -0.2979(5) 0.04390(12) 0.0396(9) Uani 1 1 d . . . C9 C 0.6947(3) -0.2626(4) 0.07883(11) 0.0257(7) Uani 1 1 d . . . C10 C 0.6138(3) -0.3978(4) 0.08614(12) 0.0340(8) Uani 1 1 d . . . C11 C 0.7722(3) -0.2165(4) 0.12876(12) 0.0336(8) Uani 1 1 d . . . C12 C 0.5356(3) -0.3696(4) 0.12420(12) 0.0358(8) Uani 1 1 d . . . C13 C 0.6929(4) -0.1856(4) 0.16635(13) 0.0409(9) Uani 1 1 d . . . C14 C 0.7720(3) -0.9270(4) -0.09831(11) 0.0253(7) Uani 1 1 d . . . C15 C 0.7632(3) -0.8973(3) -0.04570(10) 0.0229(6) Uani 1 1 d . . . C16 C 0.6477(3) -0.8963(4) -0.03191(11) 0.0301(7) Uani 1 1 d . . . C17 C 0.6392(3) -0.8605(4) 0.01566(11) 0.0306(8) Uani 1 1 d . . . C18 C 0.7468(3) -0.8308(4) 0.05056(10) 0.0241(7) Uani 1 1 d . . . C19 C 0.8623(3) -0.8378(4) 0.03730(11) 0.0320(8) Uani 1 1 d . . . C20 C 0.8709(3) -0.8695(4) -0.01092(12) 0.0328(8) Uani 1 1 d . . . C21 C 0.7355(3) -0.7904(4) 0.10215(11) 0.0268(7) Uani 1 1 d . . . H7 H 0.9243 -0.9437 -0.1615 0.080 Uiso 1 1 d . . . H18 H 0.6011 -0.7895 -0.3379 0.080 Uiso 1 1 d . . . H15 H 0.8764 -0.3808 -0.1909 0.080 Uiso 1 1 d . . . H21 H 0.7984 -0.5058 -0.2220 0.080 Uiso 1 1 d . . . H1 H 0.6631 -0.4001 0.1861 0.080 Uiso 1 1 d . . . H2 H 0.5696 -0.2922 0.1971 0.080 Uiso 1 1 d . . . H16 H 0.5764 -0.9179 -0.0548 0.080 Uiso 1 1 d . . . H17 H 0.5614 -0.8581 0.0243 0.080 Uiso 1 1 d . . . H19 H 0.9345 -0.8236 0.0608 0.080 Uiso 1 1 d . . . H20 H 0.9484 -0.8710 -0.0196 0.080 Uiso 1 1 d . . . H3A H 0.6528 -0.2990 -0.1169 0.080 Uiso 1 1 d . . . H3B H 0.7832 -0.2412 -0.1252 0.080 Uiso 1 1 d . . . H12 H 0.7402 -0.5301 -0.0866 0.080 Uiso 1 1 d . . . H4A H 0.9731 -0.4194 -0.1015 0.080 Uiso 1 1 d . . . H4B H 0.9512 -0.5808 -0.0808 0.080 Uiso 1 1 d . . . H2A H 0.9668 -0.5932 -0.1641 0.080 Uiso 1 1 d . . . H2B H 0.8375 -0.6571 -0.1563 0.080 Uiso 1 1 d . . . H6A H 0.8895 -0.4454 -0.0159 0.080 Uiso 1 1 d . . . H6B H 0.8738 -0.2816 -0.0379 0.080 Uiso 1 1 d . . . H7A H 0.6761 -0.4378 -0.0079 0.080 Uiso 1 1 d . . . H7B H 0.6716 -0.2669 -0.0248 0.080 Uiso 1 1 d . . . H8A H 0.8322 -0.2084 0.0419 0.080 Uiso 1 1 d . . . H8B H 0.8380 -0.3781 0.0586 0.080 Uiso 1 1 d . . . H9A H 0.6402 -0.1776 0.0654 0.080 Uiso 1 1 d . . . H10A H 0.5578 -0.4217 0.0554 0.080 Uiso 1 1 d . . . H10B H 0.6663 -0.4851 0.0962 0.080 Uiso 1 1 d . . . H12A H 0.4746 -0.2902 0.1125 0.080 Uiso 1 1 d . . . H12B H 0.4905 -0.4609 0.1290 0.080 Uiso 1 1 d . . . H13A H 0.7457 -0.1623 0.1975 0.080 Uiso 1 1 d . . . H13B H 0.6382 -0.0991 0.1561 0.080 Uiso 1 1 d . . . H11A H 0.8312 -0.2954 0.1407 0.080 Uiso 1 1 d . . . H11B H 0.8183 -0.1242 0.1247 0.080 Uiso 1 1 d . . . H1A H 0.6464 -0.4823 -0.1775 0.080 Uiso 1 1 d . . . H1B H 0.6698 -0.3312 -0.2005 0.080 Uiso 1 1 d . . . O7 O 0.5337(2) -0.5580(3) -0.28629(9) 0.0314(5) 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 0.01460(17) 0.02166(19) 0.01606(16) -0.00139(13) 0.00505(12) -0.00112(13) Zn2 0.01435(17) 0.01940(18) 0.01675(17) 0.00043(13) 0.00595(13) 0.00035(13) P1 0.0153(4) 0.0167(4) 0.0170(3) -0.0007(3) 0.0057(3) 0.0003(3) P2 0.0133(4) 0.0191(4) 0.0169(3) 0.0016(3) 0.0059(3) 0.0005(3) O1 0.0373(13) 0.0210(11) 0.0190(10) 0.0022(8) 0.0119(9) 0.0019(9) O2 0.0153(11) 0.0196(11) 0.0329(12) 0.0045(9) 0.0061(9) 0.0036(8) O3 0.0146(11) 0.0267(11) 0.0319(12) -0.0062(9) 0.0091(9) 0.0002(9) O4 0.0357(13) 0.0276(12) 0.0216(11) -0.0060(9) 0.0092(9) -0.0110(10) O5 0.0153(10) 0.0236(11) 0.0239(10) -0.0044(8) 0.0065(8) -0.0001(8) O6 0.0301(12) 0.0225(11) 0.0192(10) 0.0018(8) 0.0124(9) 0.0018(9) O8 0.0295(12) 0.0315(12) 0.0203(11) -0.0061(9) 0.0078(9) -0.0123(10) O9 0.0343(14) 0.0511(15) 0.0152(10) -0.0036(10) 0.0003(9) 0.0077(11) O10 0.0377(14) 0.0520(16) 0.0165(11) -0.0074(10) 0.0072(10) -0.0046(12) O11 0.0351(15) 0.077(2) 0.0217(12) -0.0102(12) 0.0112(11) -0.0022(13) O12 0.0369(15) 0.074(2) 0.0221(12) -0.0072(12) 0.0141(11) 0.0002(13) N1 0.0276(15) 0.0264(14) 0.0238(13) -0.0034(11) 0.0103(11) -0.0070(11) N2 0.0429(18) 0.0442(18) 0.0215(14) 0.0071(12) 0.0133(12) 0.0076(14) C1 0.0259(17) 0.0284(17) 0.0300(17) 0.0015(14) 0.0091(14) 0.0043(14) C2 0.0309(19) 0.038(2) 0.0314(18) -0.0022(15) 0.0105(14) 0.0103(15) C3 0.0320(18) 0.0276(17) 0.0292(17) -0.0061(14) 0.0118(14) 0.0023(14) C4 0.0286(19) 0.056(2) 0.0280(18) -0.0027(16) 0.0057(14) 0.0096(17) C5 0.0234(17) 0.044(2) 0.0234(16) -0.0030(14) 0.0070(13) 0.0024(15) C6 0.0283(19) 0.085(3) 0.0233(18) -0.0121(18) 0.0096(15) 0.002(2) C7 0.0296(19) 0.057(2) 0.0251(17) -0.0044(16) 0.0119(14) 0.0001(17) C8 0.0259(19) 0.068(3) 0.0272(18) -0.0094(17) 0.0116(14) 0.0001(18) C9 0.0248(17) 0.0323(18) 0.0219(15) -0.0017(13) 0.0090(13) 0.0007(13) C10 0.037(2) 0.039(2) 0.0288(18) -0.0038(15) 0.0118(15) -0.0079(16) C11 0.0309(19) 0.045(2) 0.0261(17) -0.0069(15) 0.0078(14) -0.0067(16) C12 0.0337(19) 0.048(2) 0.0268(17) 0.0085(16) 0.0082(14) -0.0008(16) C13 0.055(3) 0.040(2) 0.0310(19) -0.0085(16) 0.0165(17) -0.0031(18) C14 0.0316(18) 0.0276(17) 0.0180(15) -0.0035(12) 0.0080(13) -0.0001(14) C15 0.0263(17) 0.0252(16) 0.0177(14) -0.0009(12) 0.0052(12) 0.0020(13) C16 0.0266(17) 0.043(2) 0.0208(15) 0.0008(14) 0.0047(13) -0.0002(15) C17 0.0244(17) 0.046(2) 0.0228(16) 0.0003(14) 0.0089(13) -0.0003(15) C18 0.0315(18) 0.0263(16) 0.0161(14) -0.0011(12) 0.0087(12) 0.0007(13) C19 0.0285(18) 0.050(2) 0.0182(15) -0.0078(15) 0.0066(13) -0.0059(16) C20 0.0243(17) 0.053(2) 0.0224(16) -0.0071(15) 0.0080(13) -0.0046(16) C21 0.038(2) 0.0261(17) 0.0184(15) 0.0018(12) 0.0104(14) 0.0006(14) O7 0.0198(12) 0.0301(13) 0.0465(14) 0.0136(11) 0.0122(10) 0.0108(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O3 1.912(2) . ? Zn1 O7 1.922(2) 2_644 ? Zn1 O9 1.942(2) . ? Zn1 O6 1.957(2) . ? Zn2 O5 1.9377(19) . ? Zn2 O2 1.942(2) 2_754 ? Zn2 O1 1.952(2) . ? Zn2 O10 1.971(2) 4_545 ? P1 O1 1.513(2) . ? P1 O3 1.523(2) . ? P1 O2 1.523(2) . ? P1 O4 1.569(2) . ? P2 O7 1.497(2) . ? P2 O6 1.516(2) . ? P2 O5 1.539(2) . ? P2 O8 1.574(2) . ? O2 Zn2 1.9424(19) 2_744 ? O4 H7 0.9431 . ? O8 H18 0.8677 . ? O9 C14 1.276(4) . ? O10 C21 1.271(4) . ? O10 Zn2 1.971(2) 4_546 ? O11 C14 1.234(4) . ? O12 C21 1.237(4) . ? N1 C2 1.486(4) . ? N1 C1 1.495(4) . ? N1 H15 0.8591 . ? N1 H21 0.9804 . ? N2 C12 1.492(4) . ? N2 C13 1.501(5) . ? N2 H1 0.9149 . ? N2 H2 0.9563 . ? C1 C3 1.510(4) . ? C1 H1A 0.9710 . ? C1 H1B 0.9102 . ? C2 C4 1.515(5) . ? C2 H2A 0.9645 . ? C2 H2B 0.9770 . ? C3 C5 1.522(5) . ? C3 H3A 0.9698 . ? C3 H3B 0.9750 . ? C4 C5 1.521(5) . ? C4 H4A 0.9686 . ? C4 H4B 0.9702 . ? C5 C6 1.533(5) . ? C5 H12 0.9706 . ? C6 C7 1.519(5) . ? C6 H6A 0.9610 . ? C6 H6B 0.9784 . ? C7 C8 1.526(5) . ? C7 H7A 0.9627 . ? C7 H7B 0.9727 . ? C8 C9 1.516(4) . ? C8 H8A 0.9645 . ? C8 H8B 0.9688 . ? C9 C10 1.516(5) . ? C9 C11 1.533(4) . ? C9 H9A 0.9828 . ? C10 C12 1.499(5) . ? C10 H10A 0.9726 . ? C10 H10B 0.9660 . ? C11 C13 1.501(5) . ? C11 H11A 0.9605 . ? C11 H11B 0.9720 . ? C12 H12A 0.9756 . ? C12 H12B 0.9635 . ? C13 H13A 0.9656 . ? C13 H13B 0.9744 . ? C14 C15 1.505(4) . ? C15 C16 1.384(4) . ? C15 C20 1.391(4) . ? C16 C17 1.378(4) . ? C16 H16 0.9227 . ? C17 C18 1.395(4) . ? C17 H17 0.9244 . ? C18 C19 1.378(4) . ? C18 C21 1.503(4) . ? C19 C20 1.388(4) . ? C19 H19 0.9285 . ? C20 H20 0.9209 . ? O7 Zn1 1.922(2) 2_654 ? 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 O7 111.14(9) . 2_644 ? O3 Zn1 O9 117.82(9) . . ? O7 Zn1 O9 106.55(10) 2_644 . ? O3 Zn1 O6 117.59(9) . . ? O7 Zn1 O6 99.76(10) 2_644 . ? O9 Zn1 O6 101.92(9) . . ? O5 Zn2 O2 115.73(8) . 2_754 ? O5 Zn2 O1 116.09(9) . . ? O2 Zn2 O1 101.64(9) 2_754 . ? O5 Zn2 O10 110.77(9) . 4_545 ? O2 Zn2 O10 103.77(10) 2_754 4_545 ? O1 Zn2 O10 107.71(9) . 4_545 ? O1 P1 O3 110.65(13) . . ? O1 P1 O2 112.05(12) . . ? O3 P1 O2 107.88(12) . . ? O1 P1 O4 106.06(12) . . ? O3 P1 O4 110.07(12) . . ? O2 P1 O4 110.15(12) . . ? O7 P2 O6 111.21(12) . . ? O7 P2 O5 109.46(12) . . ? O6 P2 O5 111.11(12) . . ? O7 P2 O8 110.93(13) . . ? O6 P2 O8 106.80(12) . . ? O5 P2 O8 107.24(11) . . ? P1 O1 Zn2 123.48(12) . . ? P1 O2 Zn2 138.63(13) . 2_744 ? P1 O3 Zn1 131.78(13) . . ? P1 O4 H7 113.8 . . ? P2 O5 Zn2 125.37(12) . . ? P2 O6 Zn1 125.83(12) . . ? P2 O8 H18 107.7 . . ? C14 O9 Zn1 131.6(2) . . ? C21 O10 Zn2 131.7(2) . 4_546 ? C2 N1 C1 111.8(2) . . ? C2 N1 H15 104.4 . . ? C1 N1 H15 113.3 . . ? C2 N1 H21 106.1 . . ? C1 N1 H21 106.8 . . ? H15 N1 H21 114.4 . . ? C12 N2 C13 111.9(3) . . ? C12 N2 H1 111.0 . . ? C13 N2 H1 110.0 . . ? C12 N2 H2 116.4 . . ? C13 N2 H2 103.8 . . ? H1 N2 H2 103.1 . . ? N1 C1 C3 110.4(3) . . ? N1 C1 H1A 109.6 . . ? C3 C1 H1A 109.2 . . ? N1 C1 H1B 105.5 . . ? C3 C1 H1B 114.6 . . ? H1A C1 H1B 107.4 . . ? N1 C2 C4 111.1(3) . . ? N1 C2 H2A 109.9 . . ? C4 C2 H2A 109.0 . . ? N1 C2 H2B 109.6 . . ? C4 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C1 C3 C5 112.2(3) . . ? C1 C3 H3A 108.9 . . ? C5 C3 H3A 109.7 . . ? C1 C3 H3B 109.2 . . ? C5 C3 H3B 109.4 . . ? H3A C3 H3B 107.3 . . ? C2 C4 C5 112.8(3) . . ? C2 C4 H4A 109.1 . . ? C5 C4 H4A 108.9 . . ? C2 C4 H4B 109.4 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C3 108.8(3) . . ? C4 C5 C6 109.3(3) . . ? C3 C5 C6 113.6(3) . . ? C4 C5 H12 108.5 . . ? C3 C5 H12 108.3 . . ? C6 C5 H12 108.3 . . ? C7 C6 C5 117.7(3) . . ? C7 C6 H6A 108.1 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6B 107.0 . . ? C5 C6 H6B 107.8 . . ? H6A C6 H6B 107.2 . . ? C6 C7 C8 108.5(3) . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7A 110.4 . . ? C6 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.6 . . ? C9 C8 C7 118.4(3) . . ? C9 C8 H8A 107.5 . . ? C7 C8 H8A 107.9 . . ? C9 C8 H8B 107.4 . . ? C7 C8 H8B 107.6 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 112.2(3) . . ? C8 C9 C11 109.2(3) . . ? C10 C9 C11 108.6(3) . . ? C8 C9 H9A 108.7 . . ? C10 C9 H9A 108.8 . . ? C11 C9 H9A 109.3 . . ? C12 C10 C9 112.8(3) . . ? C12 C10 H10A 108.0 . . ? C9 C10 H10A 109.6 . . ? C12 C10 H10B 108.3 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.6 . . ? C13 C11 C9 112.7(3) . . ? C13 C11 H11A 109.1 . . ? C9 C11 H11A 109.7 . . ? C13 C11 H11B 108.0 . . ? C9 C11 H11B 108.8 . . ? H11A C11 H11B 108.4 . . ? N2 C12 C10 111.6(3) . . ? N2 C12 H12A 109.2 . . ? C10 C12 H12A 109.1 . . ? N2 C12 H12B 109.3 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 108.0 . . ? N2 C13 C11 110.3(3) . . ? N2 C13 H13A 109.4 . . ? C11 C13 H13A 109.8 . . ? N2 C13 H13B 108.7 . . ? C11 C13 H13B 109.9 . . ? H13A C13 H13B 108.7 . . ? O11 C14 O9 126.1(3) . . ? O11 C14 C15 118.1(3) . . ? O9 C14 C15 115.8(3) . . ? C16 C15 C20 119.8(3) . . ? C16 C15 C14 120.0(3) . . ? C20 C15 C14 120.2(3) . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 120.5(3) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 120.3 . . ? C19 C18 C17 119.6(3) . . ? C19 C18 C21 120.7(3) . . ? C17 C18 C21 119.6(3) . . ? C18 C19 C20 120.0(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 120.1(3) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 120.7 . . ? O12 C21 O10 126.5(3) . . ? O12 C21 C18 116.7(3) . . ? O10 C21 C18 116.8(3) . . ? P2 O7 Zn1 149.01(15) . 2_654 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.460 _refine_diff_density_min -0.547 _refine_diff_density_rms 0.098