# 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 ? _publ_contact_author_name 'Vitezslav Zima' _publ_contact_author_email Vitezslav.Zima@upce.cz loop_ _publ_author_name 'Vitezslav Zima' 'Jan Svoboda' 'Yaching Yang' 'Sue-Lein Wang' data_Cmpd1 _database_code_depnum_ccdc_archive 'CCDC 857310' #TrackingRef '- CuPP2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 Cu N2 O7 P S' _chemical_formula_weight 497.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.3822(2) _cell_length_b 11.1231(2) _cell_length_c 15.3382(2) _cell_angle_alpha 90.00 _cell_angle_beta 105.2120(10) _cell_angle_gamma 90.00 _cell_volume 1873.86(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5684 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Lump _exptl_crystal_colour Blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 1.410 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6910 _exptl_absorpt_correction_T_max 0.7457 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18131 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4661 _reflns_number_gt 3863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 2008)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _computing_publication_material 'Bruker APEX2' _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^)+(0.0433P)^2^+0.5676P] 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 4661 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 Cu1 Cu 0.29582(2) 0.08830(2) 1.006833(15) 0.02566(8) Uani 1 1 d . . . S1 S 0.28663(5) 0.40743(4) 1.04268(3) 0.02978(12) Uani 1 1 d . . . P1 P 0.03249(4) 0.54180(5) 0.63395(3) 0.02502(11) Uani 1 1 d . . . N1 N 0.18250(15) 0.09841(14) 1.08752(11) 0.0276(3) Uani 1 1 d . . . N2 N 0.14376(14) 0.13762(15) 0.91307(11) 0.0278(3) Uani 1 1 d . . . O1 O 0.34719(13) 0.29200(13) 1.03903(10) 0.0356(3) Uani 1 1 d . . . O2 O 0.37691(16) 0.50076(15) 1.07314(10) 0.0477(4) Uani 1 1 d . . . O3 O 0.19440(17) 0.40147(17) 1.09090(11) 0.0504(5) Uani 1 1 d . . . O4 O -0.07124(14) 0.45668(17) 0.60555(10) 0.0479(4) Uani 1 1 d . . . O5 O -0.01356(19) 0.67257(16) 0.63698(11) 0.0585(5) Uani 1 1 d . . . O6 O 0.12808(13) 0.53421(17) 0.58349(10) 0.0430(4) Uani 1 1 d . . . O7 O 0.42105(14) 0.70687(15) 0.98968(12) 0.0451(4) Uani 1 1 d . . . C1 C 0.2067(2) 0.0793(2) 1.17596(15) 0.0363(5) Uani 1 1 d . . . C2 C 0.1198(3) 0.1003(2) 1.22444(17) 0.0464(6) Uani 1 1 d . . . C3 C 0.0063(2) 0.1390(2) 1.17975(18) 0.0474(6) Uani 1 1 d . . . C4 C -0.02389(19) 0.1563(2) 1.08624(17) 0.0391(5) Uani 1 1 d . . . C5 C -0.1411(2) 0.1931(2) 1.0318(2) 0.0512(7) Uani 1 1 d . . . C6 C -0.1615(2) 0.2091(2) 0.9422(2) 0.0537(7) Uani 1 1 d . . . C7 C -0.06772(19) 0.1923(2) 0.89679(16) 0.0400(5) Uani 1 1 d . . . C8 C -0.0809(2) 0.2093(2) 0.80425(18) 0.0495(6) Uani 1 1 d . . . C9 C 0.0159(2) 0.1947(2) 0.76885(16) 0.0471(6) Uani 1 1 d . . . C10 C 0.1280(2) 0.1586(2) 0.82514(14) 0.0365(5) Uani 1 1 d . . . C11 C 0.04780(17) 0.15539(17) 0.94851(14) 0.0290(4) Uani 1 1 d . . . C12 C 0.06921(17) 0.13596(17) 1.04337(14) 0.0286(4) Uani 1 1 d . . . C13 C 0.21317(18) 0.44406(17) 0.92878(12) 0.0270(4) Uani 1 1 d . . . C14 C 0.10107(18) 0.5014(2) 0.90714(13) 0.0320(4) Uani 1 1 d . . . C15 C 0.04695(18) 0.53392(19) 0.81815(13) 0.0308(4) Uani 1 1 d . . . C16 C 0.10349(16) 0.50790(17) 0.75006(12) 0.0249(4) Uani 1 1 d . . . C17 C 0.21623(19) 0.4500(2) 0.77313(13) 0.0332(4) Uani 1 1 d . . . C18 C 0.2709(2) 0.4184(2) 0.86182(14) 0.0351(5) Uani 1 1 d . . . H1 H 0.2901 0.0553 1.2078 0.080 Uiso 1 1 d . . . H2 H 0.1405 0.0905 1.2912 0.080 Uiso 1 1 d . . . H3 H -0.0526 0.1586 1.2081 0.080 Uiso 1 1 d . . . H4 H -0.2013 0.2092 1.0657 0.080 Uiso 1 1 d . . . H5 H -0.2385 0.2303 0.9059 0.080 Uiso 1 1 d . . . H6 H -0.1579 0.2293 0.7687 0.080 Uiso 1 1 d . . . H7 H 0.0128 0.2017 0.7059 0.080 Uiso 1 1 d . . . H8 H 0.2013 0.1457 0.8009 0.080 Uiso 1 1 d . . . H9 H 0.0652 0.5158 0.9521 0.080 Uiso 1 1 d . . . H10 H -0.0276 0.5771 0.8031 0.080 Uiso 1 1 d . . . H11 H 0.2571 0.4290 0.7275 0.080 Uiso 1 1 d . . . H12 H 0.3473 0.3702 0.8797 0.080 Uiso 1 1 d . . . H13 H -0.0379 0.7065 0.5809 0.080 Uiso 1 1 d . . . H14 H 0.4873 0.7009 0.9684 0.080 Uiso 1 1 d . . . H15 H 0.4135 0.6319 1.0094 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 Cu1 0.02123(12) 0.03676(15) 0.01830(13) 0.00144(9) 0.00398(9) 0.00389(9) S1 0.0356(3) 0.0346(3) 0.0177(2) 0.00237(18) 0.0043(2) -0.0010(2) P1 0.0222(2) 0.0344(3) 0.0171(2) 0.00108(19) 0.00269(18) -0.00268(19) N1 0.0280(8) 0.0304(9) 0.0254(8) 0.0003(6) 0.0088(7) -0.0010(7) N2 0.0261(8) 0.0297(8) 0.0253(8) 0.0010(7) 0.0023(7) 0.0007(7) O1 0.0376(8) 0.0345(8) 0.0305(8) 0.0050(6) 0.0016(6) 0.0009(6) O2 0.0643(11) 0.0429(9) 0.0266(8) -0.0010(7) -0.0046(7) -0.0154(8) O3 0.0526(10) 0.0750(13) 0.0287(8) 0.0133(8) 0.0198(8) 0.0141(9) O4 0.0401(9) 0.0760(12) 0.0234(7) -0.0005(8) 0.0007(7) -0.0292(8) O5 0.0910(14) 0.0481(10) 0.0327(9) 0.0062(8) 0.0099(9) 0.0267(10) O6 0.0288(7) 0.0773(12) 0.0241(7) 0.0111(7) 0.0091(6) -0.0017(8) O7 0.0419(9) 0.0393(9) 0.0549(10) -0.0076(7) 0.0145(8) -0.0049(7) C1 0.0432(12) 0.0400(12) 0.0277(11) 0.0014(9) 0.0127(9) -0.0023(9) C2 0.0607(16) 0.0484(14) 0.0375(13) -0.0041(10) 0.0262(12) -0.0103(12) C3 0.0494(14) 0.0482(14) 0.0562(15) -0.0109(12) 0.0346(12) -0.0097(11) C4 0.0333(11) 0.0345(11) 0.0554(14) -0.0088(10) 0.0220(10) -0.0041(9) C5 0.0285(11) 0.0525(15) 0.0761(19) -0.0120(13) 0.0199(12) 0.0003(10) C6 0.0254(11) 0.0515(15) 0.080(2) -0.0048(14) 0.0059(12) 0.0079(10) C7 0.0285(10) 0.0348(12) 0.0504(14) -0.0021(10) -0.0007(10) 0.0021(9) C8 0.0385(13) 0.0450(14) 0.0513(15) 0.0063(11) -0.0124(11) 0.0069(11) C9 0.0519(14) 0.0453(14) 0.0330(12) 0.0054(10) -0.0089(11) 0.0007(11) C10 0.0410(11) 0.0393(12) 0.0255(10) 0.0027(9) 0.0018(9) -0.0008(9) C11 0.0242(9) 0.0259(10) 0.0347(11) -0.0022(8) 0.0042(8) -0.0021(7) C12 0.0246(9) 0.0249(9) 0.0373(11) -0.0034(8) 0.0096(8) -0.0034(7) C13 0.0315(10) 0.0296(10) 0.0176(9) 0.0015(7) 0.0023(7) -0.0018(8) C14 0.0326(10) 0.0435(12) 0.0213(9) -0.0017(8) 0.0093(8) 0.0026(9) C15 0.0264(9) 0.0420(11) 0.0234(9) -0.0002(8) 0.0056(8) 0.0034(8) C16 0.0256(9) 0.0303(9) 0.0179(8) -0.0010(7) 0.0040(7) -0.0044(7) C17 0.0303(10) 0.0495(12) 0.0207(9) 0.0026(9) 0.0081(8) 0.0088(9) C18 0.0323(11) 0.0482(13) 0.0238(10) 0.0055(9) 0.0056(8) 0.0099(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 Cu1 O4 1.9053(15) 4_666 ? Cu1 O6 1.9136(14) 2_546 ? Cu1 N1 2.0113(16) . ? Cu1 N2 2.0146(16) . ? Cu1 O1 2.3596(15) . ? S1 O3 1.4356(17) . ? S1 O2 1.4491(17) . ? S1 O1 1.4653(15) . ? S1 C13 1.7750(19) . ? P1 O4 1.4867(15) . ? P1 O6 1.4939(14) . ? P1 O5 1.5510(18) . ? P1 C16 1.7920(19) . ? N1 C1 1.329(3) . ? N1 C12 1.356(3) . ? N2 C10 1.334(3) . ? N2 C11 1.356(2) . ? O4 Cu1 1.9053(15) 4_565 ? O5 H13 0.9132 . ? O6 Cu1 1.9136(14) 2_556 ? O7 H14 0.8993 . ? O7 H15 0.8989 . ? C1 C2 1.404(3) . ? C1 H1 0.9837 . ? C2 C3 1.364(4) . ? C2 H2 0.9947 . ? C3 C4 1.398(3) . ? C3 H3 0.9157 . ? C4 C12 1.404(3) . ? C4 C5 1.435(3) . ? C5 C6 1.345(4) . ? C5 H4 0.9790 . ? C6 C7 1.431(4) . ? C6 H5 0.9366 . ? C7 C8 1.400(4) . ? C7 C11 1.407(3) . ? C8 C9 1.360(4) . ? C8 H6 0.9294 . ? C9 C10 1.398(3) . ? C9 H7 0.9601 . ? C10 H8 1.0092 . ? C11 C12 1.427(3) . ? C13 C18 1.386(3) . ? C13 C14 1.387(3) . ? C14 C15 1.390(3) . ? C14 H9 0.9031 . ? C15 C16 1.393(3) . ? C15 H10 0.9493 . ? C16 C17 1.396(3) . ? C17 C18 1.384(3) . ? C17 H11 0.9652 . ? C18 H12 0.9970 . ? 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 Cu1 O6 94.41(6) 4_666 2_546 ? O4 Cu1 N1 91.69(7) 4_666 . ? O6 Cu1 N1 161.49(7) 2_546 . ? O4 Cu1 N2 173.31(7) 4_666 . ? O6 Cu1 N2 92.07(7) 2_546 . ? N1 Cu1 N2 81.63(7) . . ? O4 Cu1 O1 89.10(7) 4_666 . ? O6 Cu1 O1 108.61(7) 2_546 . ? N1 Cu1 O1 88.93(6) . . ? N2 Cu1 O1 90.41(6) . . ? O3 S1 O2 114.80(11) . . ? O3 S1 O1 113.21(10) . . ? O2 S1 O1 109.83(10) . . ? O3 S1 C13 107.36(10) . . ? O2 S1 C13 105.31(9) . . ? O1 S1 C13 105.56(9) . . ? O4 P1 O6 116.27(10) . . ? O4 P1 O5 110.94(12) . . ? O6 P1 O5 111.49(11) . . ? O4 P1 C16 105.88(9) . . ? O6 P1 C16 107.65(9) . . ? O5 P1 C16 103.62(9) . . ? C1 N1 C12 118.32(18) . . ? C1 N1 Cu1 128.66(15) . . ? C12 N1 Cu1 112.92(13) . . ? C10 N2 C11 118.09(17) . . ? C10 N2 Cu1 129.21(14) . . ? C11 N2 Cu1 112.64(13) . . ? S1 O1 Cu1 139.13(9) . . ? P1 O4 Cu1 143.53(11) . 4_565 ? P1 O5 H13 112.4 . . ? P1 O6 Cu1 152.49(12) . 2_556 ? H14 O7 H15 102.5 . . ? N1 C1 C2 121.9(2) . . ? N1 C1 H1 117.7 . . ? C2 C1 H1 120.3 . . ? C3 C2 C1 119.5(2) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 121.2 . . ? C2 C3 C4 120.3(2) . . ? C2 C3 H3 123.5 . . ? C4 C3 H3 116.2 . . ? C3 C4 C12 116.5(2) . . ? C3 C4 C5 125.2(2) . . ? C12 C4 C5 118.3(2) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H4 124.1 . . ? C4 C5 H4 114.6 . . ? C5 C6 C7 121.9(2) . . ? C5 C6 H5 121.6 . . ? C7 C6 H5 116.4 . . ? C8 C7 C11 116.5(2) . . ? C8 C7 C6 125.4(2) . . ? C11 C7 C6 118.0(2) . . ? C9 C8 C7 120.4(2) . . ? C9 C8 H6 122.2 . . ? C7 C8 H6 117.4 . . ? C8 C9 C10 119.4(2) . . ? C8 C9 H7 124.9 . . ? C10 C9 H7 115.6 . . ? N2 C10 C9 122.3(2) . . ? N2 C10 H8 116.3 . . ? C9 C10 H8 121.5 . . ? N2 C11 C7 123.26(19) . . ? N2 C11 C12 116.52(17) . . ? C7 C11 C12 120.22(19) . . ? N1 C12 C4 123.5(2) . . ? N1 C12 C11 116.20(17) . . ? C4 C12 C11 120.33(19) . . ? C18 C13 C14 120.17(18) . . ? C18 C13 S1 119.31(15) . . ? C14 C13 S1 120.49(15) . . ? C13 C14 C15 119.84(17) . . ? C13 C14 H9 118.1 . . ? C15 C14 H9 122.1 . . ? C14 C15 C16 120.61(18) . . ? C14 C15 H10 120.5 . . ? C16 C15 H10 118.8 . . ? C15 C16 C17 118.72(17) . . ? C15 C16 P1 121.64(14) . . ? C17 C16 P1 119.60(14) . . ? C18 C17 C16 120.82(18) . . ? C18 C17 H11 118.3 . . ? C16 C17 H11 120.9 . . ? C17 C18 C13 119.84(19) . . ? C17 C18 H12 122.8 . . ? C13 C18 H12 117.1 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.371 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.064 #===END data_Cmpd2 _database_code_depnum_ccdc_archive 'CCDC 857311' #TrackingRef '- CuPP2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 Cu N2 O6 P' _chemical_formula_weight 461.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 10.2042(3) _cell_length_b 6.9866(2) _cell_length_c 24.8482(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.9290(10) _cell_angle_gamma 90.00 _cell_volume 1771.26(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description lump _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.366 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6997 _exptl_absorpt_correction_T_max 0.7457 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18050 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4371 _reflns_number_gt 3432 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0699P)^2^+0.0481P] 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 4371 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.1150 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 Cu1 Cu 0.29716(3) 0.66772(4) 0.129147(10) 0.02165(12) Uani 1 1 d . . . P1 P 0.37184(5) 0.54038(8) 0.25186(2) 0.01776(15) Uani 1 1 d . . . O1 O 0.34188(16) 0.3218(2) 0.25567(7) 0.0266(4) Uani 1 1 d . . . H1A H 0.4007 0.2612 0.2414 0.040 Uiso 1 1 calc R . . O2 O 0.38829(17) 0.6036(3) 0.19454(6) 0.0306(4) Uani 1 1 d . . . O3 O 0.48850(15) 0.5967(2) 0.28624(7) 0.0265(4) Uani 1 1 d . . . O4 O 0.30356(17) 0.9735(2) 0.15053(8) 0.0364(4) Uani 1 1 d . . . O5 O -0.12320(16) 1.0888(2) 0.34676(7) 0.0286(4) Uani 1 1 d . . . O6 O -0.18204(18) 0.8080(2) 0.38048(8) 0.0353(4) Uani 1 1 d . . . C1 C 0.1142(3) 0.7207(5) 0.03233(12) 0.0434(7) Uani 1 1 d . . . H1 H 0.0446 0.7042 0.0556 0.052 Uiso 1 1 calc R . . C2 C 0.7070(3) 0.7172(4) 0.08564(13) 0.0421(7) Uani 1 1 d . . . H2 H 0.7890 0.7149 0.1025 0.051 Uiso 1 1 calc R . . C3 C 0.5513(3) 0.7770(4) -0.04984(11) 0.0439(7) Uani 1 1 d . . . H3 H 0.6228 0.7892 -0.0723 0.053 Uiso 1 1 calc R . . C4 C 0.4296(3) 0.7870(4) -0.07100(11) 0.0440(8) Uani 1 1 d . . . H4A H 0.4186 0.8071 -0.1078 0.053 Uiso 1 1 calc R . . C5 C 0.1870(3) 0.7762(5) -0.05665(12) 0.0484(8) Uani 1 1 d . . . H5 H 0.1695 0.7978 -0.0930 0.058 Uiso 1 1 calc R . . C6 C 0.3159(3) 0.7671(4) -0.03794(10) 0.0342(6) Uani 1 1 d . . . C7 C 0.5934(2) 0.6939(4) 0.11598(11) 0.0321(6) Uani 1 1 d . . . H7 H 0.6014 0.6763 0.1530 0.038 Uiso 1 1 calc R . . C8 C 0.4643(2) 0.7264(3) 0.03966(9) 0.0249(5) Uani 1 1 d . . . C9 C 0.6972(3) 0.7430(4) 0.03156(12) 0.0407(7) Uani 1 1 d . . . H9 H 0.7723 0.7572 0.0113 0.049 Uiso 1 1 calc R . . C10 C 0.5732(2) 0.7481(4) 0.00648(10) 0.0317(6) Uani 1 1 d . . . C11 C 0.3351(2) 0.7356(3) 0.01735(9) 0.0255(5) Uani 1 1 d . . . C12 C 0.2267(2) 0.6458(3) 0.28007(9) 0.0189(5) Uani 1 1 d . . . C13 C 0.0866(3) 0.7538(5) -0.02225(13) 0.0535(8) Uani 1 1 d . . . H13 H 0.0004 0.7603 -0.0347 0.064 Uiso 1 1 calc R . . C14 C 0.2183(2) 0.8436(3) 0.28428(10) 0.0276(6) Uani 1 1 d . . . H14 H 0.2868 0.9196 0.2723 0.033 Uiso 1 1 calc R . . C15 C 0.1235(2) 0.5349(3) 0.29808(10) 0.0255(5) Uani 1 1 d . . . H15 H 0.1270 0.4024 0.2947 0.031 Uiso 1 1 calc R . . C16 C 0.0148(2) 0.6203(4) 0.32117(10) 0.0268(5) Uani 1 1 d . . . H16 H -0.0532 0.5445 0.3336 0.032 Uiso 1 1 calc R . . C17 C 0.1084(2) 0.9284(3) 0.30619(10) 0.0261(5) Uani 1 1 d . . . H17 H 0.1027 1.0611 0.3078 0.031 Uiso 1 1 calc R . . C18 C -0.1080(2) 0.9092(3) 0.35282(9) 0.0236(5) Uani 1 1 d . . . C19 C 0.0072(2) 0.8179(3) 0.32571(9) 0.0212(5) Uani 1 1 d . . . N1 N 0.4750(2) 0.6963(3) 0.09330(8) 0.0243(4) Uani 1 1 d . . . N2 N 0.2354(2) 0.7118(3) 0.05216(8) 0.0295(5) Uani 1 1 d . . . H4B H 0.3558 1.0057 0.1665 0.080 Uiso 1 1 d . . . H4C H 0.2736 1.0588 0.1430 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 Cu1 0.02016(18) 0.02417(18) 0.02073(18) 0.00284(11) 0.00360(12) -0.00370(11) P1 0.0155(3) 0.0176(3) 0.0203(3) 0.0020(2) 0.0033(2) 0.0010(2) O1 0.0240(9) 0.0177(8) 0.0383(10) -0.0003(7) 0.0106(7) 0.0021(6) O2 0.0275(9) 0.0423(10) 0.0221(9) 0.0079(8) 0.0052(7) 0.0037(8) O3 0.0187(8) 0.0299(9) 0.0309(9) 0.0054(8) -0.0018(7) -0.0022(7) O4 0.0344(10) 0.0221(9) 0.0523(12) -0.0047(8) -0.0103(9) 0.0001(8) O5 0.0250(9) 0.0270(9) 0.0340(10) -0.0006(8) 0.0078(7) 0.0069(7) O6 0.0301(10) 0.0308(10) 0.0455(12) -0.0050(8) 0.0163(9) -0.0032(8) C1 0.0316(15) 0.0577(19) 0.0407(16) 0.0033(14) -0.0033(12) -0.0099(14) C2 0.0244(14) 0.0485(17) 0.0535(19) -0.0009(15) 0.0039(13) -0.0023(13) C3 0.061(2) 0.0390(16) 0.0321(15) 0.0023(13) 0.0248(15) 0.0007(15) C4 0.077(2) 0.0349(16) 0.0201(13) 0.0004(12) 0.0105(14) -0.0013(15) C5 0.070(2) 0.0471(18) 0.0277(15) 0.0053(14) -0.0131(15) -0.0096(17) C6 0.0516(17) 0.0263(13) 0.0245(13) -0.0013(11) -0.0039(12) -0.0066(12) C7 0.0272(13) 0.0374(15) 0.0317(14) -0.0017(11) 0.0022(11) -0.0016(11) C8 0.0316(13) 0.0191(11) 0.0242(12) -0.0026(10) 0.0076(10) -0.0012(10) C9 0.0315(14) 0.0403(16) 0.0511(18) 0.0013(14) 0.0216(13) -0.0009(13) C10 0.0393(15) 0.0235(13) 0.0327(14) -0.0015(11) 0.0156(12) -0.0026(11) C11 0.0346(13) 0.0216(12) 0.0206(12) -0.0018(10) 0.0033(10) -0.0060(10) C12 0.0174(11) 0.0209(11) 0.0183(11) 0.0008(9) 0.0013(9) 0.0027(8) C13 0.0472(19) 0.063(2) 0.0494(19) 0.0075(17) -0.0222(16) -0.0104(17) C14 0.0255(13) 0.0211(12) 0.0367(14) 0.0013(10) 0.0122(11) -0.0026(9) C15 0.0230(12) 0.0176(11) 0.0361(14) -0.0023(10) 0.0061(10) -0.0007(9) C16 0.0202(11) 0.0245(12) 0.0358(14) -0.0024(11) 0.0075(10) -0.0025(10) C17 0.0288(13) 0.0174(12) 0.0323(13) -0.0014(10) 0.0069(11) 0.0035(9) C18 0.0195(11) 0.0286(13) 0.0228(12) -0.0063(10) -0.0015(9) 0.0015(10) C19 0.0184(11) 0.0242(12) 0.0210(11) -0.0016(9) -0.0003(9) 0.0039(9) N1 0.0256(10) 0.0249(11) 0.0225(10) -0.0002(8) 0.0040(8) -0.0023(8) N2 0.0290(11) 0.0321(12) 0.0272(11) 0.0025(9) -0.0005(9) -0.0064(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 Cu1 O2 1.9122(17) . ? Cu1 O5 1.9617(15) 2_545 ? Cu1 N2 2.028(2) . ? Cu1 N1 2.0439(19) . ? Cu1 O4 2.2022(18) . ? P1 O2 1.5034(16) . ? P1 O3 1.5062(17) . ? P1 O1 1.5607(16) . ? P1 C12 1.806(2) . ? O1 H1A 0.8200 . ? O4 H4B 0.6963 . ? O4 H4C 0.6942 . ? O5 C18 1.273(3) . ? O5 Cu1 1.9616(15) 2 ? O6 C18 1.249(3) . ? C1 N2 1.325(3) . ? C1 C13 1.400(4) . ? C1 H1 0.9300 . ? C2 C9 1.358(4) . ? C2 C7 1.402(4) . ? C2 H2 0.9300 . ? C3 C4 1.342(4) . ? C3 C10 1.428(4) . ? C3 H3 0.9300 . ? C4 C6 1.439(4) . ? C4 H4A 0.9300 . ? C5 C13 1.353(5) . ? C5 C6 1.390(4) . ? C5 H5 0.9300 . ? C6 C11 1.402(3) . ? C7 N1 1.326(3) . ? C7 H7 0.9300 . ? C8 N1 1.352(3) . ? C8 C10 1.403(3) . ? C8 C11 1.424(3) . ? C9 C10 1.401(4) . ? C9 H9 0.9300 . ? C11 N2 1.356(3) . ? C12 C15 1.388(3) . ? C12 C14 1.388(3) . ? C13 H13 0.9300 . ? C14 C17 1.388(3) . ? C14 H14 0.9300 . ? C15 C16 1.392(3) . ? C15 H15 0.9300 . ? C16 C19 1.387(3) . ? C16 H16 0.9300 . ? C17 C19 1.383(3) . ? C17 H17 0.9300 . ? C18 C19 1.507(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 O2 Cu1 O5 96.02(7) . 2_545 ? O2 Cu1 N2 167.57(8) . . ? O5 Cu1 N2 93.54(8) 2_545 . ? O2 Cu1 N1 88.30(7) . . ? O5 Cu1 N1 167.05(7) 2_545 . ? N2 Cu1 N1 80.71(8) . . ? O2 Cu1 O4 90.59(8) . . ? O5 Cu1 O4 102.85(7) 2_545 . ? N2 Cu1 O4 95.03(8) . . ? N1 Cu1 O4 89.28(7) . . ? O2 P1 O3 111.18(10) . . ? O2 P1 O1 111.71(11) . . ? O3 P1 O1 112.02(10) . . ? O2 P1 C12 110.66(10) . . ? O3 P1 C12 108.60(10) . . ? O1 P1 C12 102.30(10) . . ? P1 O1 H1A 109.5 . . ? P1 O2 Cu1 144.46(11) . . ? Cu1 O4 H4B 118.0 . . ? Cu1 O4 H4C 139.2 . . ? H4B O4 H4C 101.9 . . ? C18 O5 Cu1 110.47(14) . 2 ? N2 C1 C13 122.6(3) . . ? N2 C1 H1 118.7 . . ? C13 C1 H1 118.7 . . ? C9 C2 C7 119.9(3) . . ? C9 C2 H2 120.0 . . ? C7 C2 H2 120.0 . . ? C4 C3 C10 121.4(3) . . ? C4 C3 H3 119.3 . . ? C10 C3 H3 119.3 . . ? C3 C4 C6 121.4(3) . . ? C3 C4 H4A 119.3 . . ? C6 C4 H4A 119.3 . . ? C13 C5 C6 120.3(3) . . ? C13 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C11 116.8(3) . . ? C5 C6 C4 124.9(3) . . ? C11 C6 C4 118.2(3) . . ? N1 C7 C2 121.7(2) . . ? N1 C7 H7 119.1 . . ? C2 C7 H7 119.1 . . ? N1 C8 C10 123.0(2) . . ? N1 C8 C11 116.7(2) . . ? C10 C8 C11 120.3(2) . . ? C2 C9 C10 119.7(2) . . ? C2 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C9 C10 C8 117.0(2) . . ? C9 C10 C3 124.4(2) . . ? C8 C10 C3 118.6(3) . . ? N2 C11 C6 123.4(2) . . ? N2 C11 C8 116.5(2) . . ? C6 C11 C8 120.2(2) . . ? C15 C12 C14 118.9(2) . . ? C15 C12 P1 121.92(17) . . ? C14 C12 P1 119.15(18) . . ? C5 C13 C1 119.3(3) . . ? C5 C13 H13 120.4 . . ? C1 C13 H13 120.4 . . ? C17 C14 C12 120.4(2) . . ? C17 C14 H14 119.8 . . ? C12 C14 H14 119.8 . . ? C12 C15 C16 120.5(2) . . ? C12 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C19 C16 C15 120.4(2) . . ? C19 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C19 C17 C14 120.8(2) . . ? C19 C17 H17 119.6 . . ? C14 C17 H17 119.6 . . ? O6 C18 O5 123.3(2) . . ? O6 C18 C19 119.3(2) . . ? O5 C18 C19 117.3(2) . . ? C17 C19 C16 118.9(2) . . ? C17 C19 C18 120.8(2) . . ? C16 C19 C18 120.2(2) . . ? C7 N1 C8 118.6(2) . . ? C7 N1 Cu1 128.56(17) . . ? C8 N1 Cu1 112.79(16) . . ? C1 N2 C11 117.5(2) . . ? C1 N2 Cu1 129.17(19) . . ? C11 N2 Cu1 113.29(16) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.609 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.221 #===END data_Cmpd3 _database_code_depnum_ccdc_archive 'CCDC 857312' #TrackingRef '- CuPP2.cif' _audit_creation_method 'APEX2 v2011.4-1' _chemical_name_systematic ? _chemical_name_common 3 _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 Cu N2 O9.50 P3' _chemical_formula_iupac ? _chemical_formula_weight 607.83 _chemical_melting_point ? _space_group_crystal_system triclinic _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.1238(8) _cell_length_b 10.4815(9) _cell_length_c 13.1430(11) _cell_angle_alpha 69.5690(10) _cell_angle_beta 75.0340(10) _cell_angle_gamma 63.5570(10) _cell_volume 1161.36(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9305 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _cell_measurement_temperature 296.(2) _exptl_crystal_description lump _exptl_crystal_colour blue _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.220 _exptl_crystal_density_diffrn 1.738 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 618 _exptl_absorpt_coefficient_mu 1.207 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_process_details ; ; _exptl_absorpt_correction_T_min 0.682 _exptl_absorpt_correction_T_max 0.745 _exptl_special_details ; ; _diffrn_ambient_temperature 296.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _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 13691 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _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. ; _reflns_number_total 5740 _reflns_number_gt 5073 _reflns_threshold_expression >2sigma(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_gt 0.0955 _refine_ls_wR_factor_ref 0.0988 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _refine_ls_number_reflns 5740 _refine_ls_number_parameters 335 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+0.3035P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.833 _refine_diff_density_min -0.352 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection 'Bruker Smart' _computing_cell_refinement 'Bruker Smart' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker Shelxtl' _computing_publication_material 'Bruker Shelxtl' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu1 0.96707(2) 0.12749(2) 0.054613(17) 0.02365(8) Uani d . 1 . . P P1 1.29734(5) -0.18682(5) 0.06484(4) 0.02290(11) Uani d . 1 . . P P2 0.73083(6) 0.11258(5) 0.26210(4) 0.02723(12) Uani d . 1 . . P P3 0.61198(7) -0.45196(6) 0.58913(4) 0.03279(13) Uani d . 1 . . O O1 1.14482(14) -0.08751(14) 0.02567(11) 0.0251(3) Uani d . 1 . . O O2 1.37796(16) -0.30893(15) 0.00327(12) 0.0316(3) Uani d . 1 . . O O3 1.29167(18) -0.25572(17) 0.18629(12) 0.0363(3) Uani d . 1 . . O O4 0.87428(16) 0.04301(16) 0.19428(11) 0.0313(3) Uani d . 1 . . O O5 0.59824(17) 0.21672(16) 0.20239(12) 0.0363(3) Uani d . 1 . . O O6 0.76444(19) 0.19120(18) 0.32935(13) 0.0396(4) Uani d . 1 . . O O7 0.44820(19) -0.41997(17) 0.60924(12) 0.0375(3) Uani d . 1 . . O O8 0.6914(2) -0.50632(18) 0.68906(13) 0.0458(4) Uani d . 1 . . O O9 0.6962(2) -0.57048(19) 0.52282(15) 0.0463(4) Uani d . 1 . . N N1 1.08044(18) 0.17711(19) 0.12860(14) 0.0289(3) Uani d . 1 . . N N2 1.03588(18) 0.26432(18) -0.07794(13) 0.0268(3) Uani d . 1 . . C C1 1.40729(19) -0.07743(19) 0.02960(15) 0.0227(3) Uani d . 1 . . C C2 0.6919(2) -0.0402(2) 0.36132(15) 0.0288(4) Uani d . 1 . . C C3 0.6401(2) -0.2875(2) 0.50538(16) 0.0314(4) Uani d . 1 . . C C4 0.7941(3) -0.1456(3) 0.43320(18) 0.0377(5) Uani d . 1 . . C C5 0.7681(3) -0.2674(2) 0.50437(18) 0.0382(5) Uani d . 1 . . C C6 0.5378(3) -0.1811(3) 0.43490(19) 0.0390(5) Uani d . 1 . . C C7 0.5639(2) -0.0583(2) 0.36346(18) 0.0375(5) Uani d . 1 . . C C8 1.0176(2) 0.3004(2) -0.18254(17) 0.0335(4) Uani d . 1 . . C C9 1.0729(3) 0.3989(3) -0.26417(19) 0.0442(5) Uani d . 1 . . C C10 1.1489(3) 0.4610(3) -0.2380(2) 0.0467(6) Uani d . 1 . . C C11 1.1717(2) 0.4240(2) -0.1280(2) 0.0362(5) Uani d . 1 . . C C12 1.2533(3) 0.4779(3) -0.0900(3) 0.0477(6) Uani d . 1 . . C C13 1.2754(3) 0.4332(3) 0.0159(3) 0.0466(6) Uani d . 1 . . C C14 1.2198(2) 0.3286(2) 0.0949(2) 0.0362(5) Uani d . 1 . . C C15 1.2432(3) 0.2718(3) 0.2060(2) 0.0461(6) Uani d . 1 . . C C16 1.1886(3) 0.1696(3) 0.2727(2) 0.0469(6) Uani d . 1 . . C C17 1.1068(3) 0.1238(3) 0.23202(18) 0.0383(5) Uani d . 1 . . C C18 1.1371(2) 0.2768(2) 0.06005(17) 0.0291(4) Uani d . 1 . . C C19 1.1129(2) 0.3246(2) -0.05123(17) 0.0280(4) Uani d . 1 . . C C20 1.4967(2) -0.0977(2) 0.10362(15) 0.0260(4) Uani d . 1 . . C C21 1.4111(2) 0.0207(2) -0.07406(15) 0.0267(4) Uani d . 1 . . O O1W 1.1112(7) -0.1238(6) 0.4645(5) 0.1021(19) Uani d P 0.5 . . H H1 0.4936 0.017 0.3116 0.08 Uiso d . 1 . . H H2 0.4466 -0.1941 0.4383 0.08 Uiso d . 1 . . H H3 0.8351 -0.3432 0.5505 0.08 Uiso d . 1 . . H H4 0.8868 -0.1309 0.4338 0.08 Uiso d . 1 . . H H5 0.9611 0.255 -0.1975 0.08 Uiso d . 1 . . H H6 1.0545 0.4182 -0.3378 0.08 Uiso d . 1 . . H H7 1.1861 0.5209 -0.2906 0.08 Uiso d . 1 . . H H8 1.2925 0.5416 -0.1418 0.08 Uiso d . 1 . . H H9 1.3242 0.4761 0.0439 0.08 Uiso d . 1 . . H H10 1.2963 0.3037 0.2307 0.08 Uiso d . 1 . . H H11 1.1927 0.1336 0.3419 0.08 Uiso d . 1 . . H H12 1.065 0.0601 0.2774 0.08 Uiso d . 1 . . H H13 1.3404 0.0395 -0.1295 0.08 Uiso d . 1 . . H H14 1.4987 -0.1731 0.1796 0.08 Uiso d . 1 . . H H15 0.6421 -0.5715 0.4887 0.08 Uiso d . 1 . . H H16 0.6874 0.2583 0.3515 0.08 Uiso d . 1 . . H H17 1.3931 -0.2828 -0.0724 0.08 Uiso d . 1 . . H H18 0.6987 -0.6243 0.7508 0.08 Uiso d . 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.02682(13) 0.02720(13) 0.02294(13) -0.01756(10) -0.00217(9) -0.00502(9) P1 0.0251(2) 0.0219(2) 0.0254(2) -0.01480(18) -0.00690(17) -0.00049(17) P2 0.0340(3) 0.0276(2) 0.0237(2) -0.0187(2) 0.00039(19) -0.00507(19) P3 0.0482(3) 0.0286(3) 0.0263(2) -0.0225(2) -0.0051(2) -0.0025(2) O1 0.0233(6) 0.0267(6) 0.0292(6) -0.0133(5) -0.0056(5) -0.0057(5) O2 0.0328(7) 0.0238(6) 0.0403(8) -0.0122(6) -0.0064(6) -0.0083(6) O3 0.0500(9) 0.0377(8) 0.0280(7) -0.0287(7) -0.0135(6) 0.0050(6) O4 0.0347(7) 0.0341(7) 0.0259(7) -0.0192(6) 0.0029(6) -0.0060(6) O5 0.0380(8) 0.0339(8) 0.0341(8) -0.0164(7) -0.0034(6) -0.0035(6) O6 0.0485(9) 0.0413(8) 0.0408(8) -0.0247(7) -0.0024(7) -0.0176(7) O7 0.0511(9) 0.0395(8) 0.0315(7) -0.0292(7) 0.0033(7) -0.0114(6) O8 0.0728(12) 0.0387(8) 0.0358(8) -0.0351(9) -0.0207(8) 0.0062(7) O9 0.0513(10) 0.0405(9) 0.0510(10) -0.0170(8) -0.0061(8) -0.0185(8) N1 0.0282(8) 0.0337(8) 0.0314(8) -0.0158(7) -0.0025(6) -0.0122(7) N2 0.0268(8) 0.0266(8) 0.0297(8) -0.0150(7) -0.0008(6) -0.0065(6) C1 0.0221(8) 0.0213(8) 0.0274(8) -0.0124(7) -0.0048(7) -0.0035(7) C2 0.0357(10) 0.0306(9) 0.0232(8) -0.0192(8) 0.0013(7) -0.0062(7) C3 0.0415(11) 0.0314(10) 0.0247(9) -0.0217(9) -0.0024(8) -0.0028(8) C4 0.0443(12) 0.0429(12) 0.0332(10) -0.0279(10) -0.0100(9) -0.0005(9) C5 0.0480(13) 0.0383(11) 0.0309(10) -0.0232(10) -0.0140(9) 0.0024(9) C6 0.0378(11) 0.0390(11) 0.0399(11) -0.0242(10) -0.0083(9) 0.0043(9) C7 0.0342(11) 0.0364(11) 0.0362(11) -0.0186(9) -0.0066(9) 0.0047(9) C8 0.0356(11) 0.0342(10) 0.0305(10) -0.0173(9) -0.0004(8) -0.0063(8) C9 0.0517(14) 0.0442(13) 0.0320(11) -0.0240(11) 0.0029(10) -0.0036(9) C10 0.0461(13) 0.0387(12) 0.0476(13) -0.0259(11) 0.0095(11) -0.0013(10) C11 0.0278(10) 0.0252(9) 0.0537(13) -0.0144(8) 0.0020(9) -0.0083(9) C12 0.0355(11) 0.0297(11) 0.0811(19) -0.0216(10) -0.0006(12) -0.0113(11) C13 0.0314(11) 0.0351(11) 0.085(2) -0.0173(9) -0.0067(11) -0.0247(12) C14 0.0249(9) 0.0322(10) 0.0603(14) -0.0109(8) -0.0070(9) -0.0219(10) C15 0.0368(12) 0.0544(14) 0.0652(16) -0.0175(11) -0.0125(11) -0.0332(13) C16 0.0424(13) 0.0646(16) 0.0450(13) -0.0196(12) -0.0116(10) -0.0250(12) C17 0.0352(11) 0.0512(13) 0.0348(11) -0.0200(10) -0.0052(9) -0.0140(10) C18 0.0239(9) 0.0264(9) 0.0426(11) -0.0113(7) -0.0009(8) -0.0161(8) C19 0.0235(9) 0.0227(8) 0.0400(10) -0.0127(7) 0.0023(8) -0.0108(8) C20 0.0309(9) 0.0266(9) 0.0244(8) -0.0173(8) -0.0080(7) -0.0001(7) C21 0.0298(9) 0.0280(9) 0.0277(9) -0.0174(8) -0.0088(7) -0.0021(7) O1W 0.101(4) 0.071(3) 0.123(5) -0.007(3) -0.066(4) -0.012(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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 O4 . 1.9369(13) ? Cu1 O1 2_755 1.9801(13) ? Cu1 N1 . 1.9987(16) ? Cu1 N2 . 2.0239(16) ? Cu1 O1 . 2.2571(13) ? P1 O3 . 1.5026(14) ? P1 O1 . 1.5289(13) ? P1 O2 . 1.5526(15) ? P1 C1 . 1.8078(17) ? P2 O5 . 1.5001(16) ? P2 O4 . 1.5091(15) ? P2 O6 . 1.5777(15) ? P2 C2 . 1.8048(19) ? P3 O7 . 1.5072(17) ? P3 O8 . 1.5202(17) ? P3 O9 . 1.5679(17) ? P3 C3 . 1.793(2) ? O1 Cu1 2_755 1.9801(13) ? O2 H17 . 0.9252 ? O6 H16 . 0.8514 ? O8 H18 . 1.2009 ? O9 H15 . 0.7982 ? N1 C17 . 1.325(3) ? N1 C18 . 1.357(3) ? N2 C8 . 1.332(3) ? N2 C19 . 1.365(2) ? C1 C21 . 1.395(2) ? C1 C20 . 1.396(2) ? C2 C7 . 1.383(3) ? C2 C4 . 1.393(3) ? C3 C6 . 1.386(3) ? C3 C5 . 1.399(3) ? C4 C5 . 1.382(3) ? C4 H4 . 1.0193 ? C5 H3 . 0.9246 ? C6 C7 . 1.393(3) ? C6 H2 . 0.979 ? C7 H1 . 0.9845 ? C8 C9 . 1.401(3) ? C8 H5 . 0.9785 ? C9 C10 . 1.368(4) ? C9 H6 . 0.967 ? C10 C11 . 1.412(4) ? C10 H7 . 0.8871 ? C11 C19 . 1.403(3) ? C11 C12 . 1.441(3) ? C12 C13 . 1.349(4) ? C12 H8 . 0.9197 ? C13 C14 . 1.431(3) ? C13 H9 . 0.9945 ? C14 C18 . 1.408(3) ? C14 C15 . 1.411(4) ? C15 C16 . 1.358(4) ? C15 H10 . 0.9123 ? C16 C17 . 1.401(3) ? C16 H11 . 0.8588 ? C17 H12 . 0.9079 ? C18 C19 . 1.419(3) ? C20 C21 2_855 1.393(2) ? C20 H14 . 1.033 ? C21 C20 2_855 1.393(2) ? C21 H13 . 1.0609 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O4 Cu1 O1 . 2_755 91.54(6) ? O4 Cu1 N1 . . 91.23(7) ? O1 Cu1 N1 2_755 . 176.87(6) ? O4 Cu1 N2 . . 165.01(6) ? O1 Cu1 N2 2_755 . 95.14(6) ? N1 Cu1 N2 . . 81.83(7) ? O4 Cu1 O1 . . 97.11(5) ? O1 Cu1 O1 2_755 . 82.09(5) ? N1 Cu1 O1 . . 99.01(6) ? N2 Cu1 O1 . . 97.09(6) ? O3 P1 O1 . . 113.99(8) ? O3 P1 O2 . . 110.18(9) ? O1 P1 O2 . . 108.87(8) ? O3 P1 C1 . . 107.06(8) ? O1 P1 C1 . . 108.94(8) ? O2 P1 C1 . . 107.61(8) ? O5 P2 O4 . . 117.04(9) ? O5 P2 O6 . . 110.85(9) ? O4 P2 O6 . . 107.11(9) ? O5 P2 C2 . . 109.72(9) ? O4 P2 C2 . . 105.51(9) ? O6 P2 C2 . . 105.94(9) ? O7 P3 O8 . . 117.06(10) ? O7 P3 O9 . . 109.84(9) ? O8 P3 O9 . . 107.08(10) ? O7 P3 C3 . . 109.33(10) ? O8 P3 C3 . . 106.55(9) ? O9 P3 C3 . . 106.43(10) ? P1 O1 Cu1 . 2_755 128.44(8) ? P1 O1 Cu1 . . 133.28(8) ? Cu1 O1 Cu1 2_755 . 97.91(5) ? P1 O2 H17 . . 119.9 ? P2 O4 Cu1 . . 130.79(9) ? P2 O6 H16 . . 113.7 ? P3 O8 H18 . . 117.2 ? P3 O9 H15 . . 111.5 ? C17 N1 C18 . . 118.68(18) ? C17 N1 Cu1 . . 128.29(15) ? C18 N1 Cu1 . . 113.01(13) ? C8 N2 C19 . . 118.21(17) ? C8 N2 Cu1 . . 129.79(13) ? C19 N2 Cu1 . . 112.00(13) ? C21 C1 C20 . . 119.43(15) ? C21 C1 P1 . . 120.36(13) ? C20 C1 P1 . . 120.07(13) ? C7 C2 C4 . . 119.03(18) ? C7 C2 P2 . . 120.50(16) ? C4 C2 P2 . . 120.39(15) ? C6 C3 C5 . . 118.63(18) ? C6 C3 P3 . . 119.74(16) ? C5 C3 P3 . . 121.51(16) ? C5 C4 C2 . . 120.19(19) ? C5 C4 H4 . . 120.5 ? C2 C4 H4 . . 119.3 ? C4 C5 C3 . . 120.9(2) ? C4 C5 H3 . . 123.4 ? C3 C5 H3 . . 115.5 ? C3 C6 C7 . . 120.30(19) ? C3 C6 H2 . . 118.1 ? C7 C6 H2 . . 121.6 ? C2 C7 C6 . . 120.9(2) ? C2 C7 H1 . . 117.8 ? C6 C7 H1 . . 121.3 ? N2 C8 C9 . . 121.9(2) ? N2 C8 H5 . . 115.2 ? C9 C8 H5 . . 122.9 ? C10 C9 C8 . . 120.3(2) ? C10 C9 H6 . . 123.7 ? C8 C9 H6 . . 116.0 ? C9 C10 C11 . . 119.30(19) ? C9 C10 H7 . . 119.6 ? C11 C10 H7 . . 121.1 ? C19 C11 C10 . . 116.9(2) ? C19 C11 C12 . . 118.2(2) ? C10 C11 C12 . . 124.9(2) ? C13 C12 C11 . . 121.6(2) ? C13 C12 H8 . . 121.5 ? C11 C12 H8 . . 116.9 ? C12 C13 C14 . . 121.0(2) ? C12 C13 H9 . . 122.0 ? C14 C13 H9 . . 116.8 ? C18 C14 C15 . . 117.1(2) ? C18 C14 C13 . . 118.4(2) ? C15 C14 C13 . . 124.6(2) ? C16 C15 C14 . . 119.3(2) ? C16 C15 H10 . . 121.9 ? C14 C15 H10 . . 118.8 ? C15 C16 C17 . . 120.3(2) ? C15 C16 H11 . . 125.4 ? C17 C16 H11 . . 114.1 ? N1 C17 C16 . . 121.9(2) ? N1 C17 H12 . . 117.5 ? C16 C17 H12 . . 120.4 ? N1 C18 C14 . . 122.7(2) ? N1 C18 C19 . . 116.65(17) ? C14 C18 C19 . . 120.60(19) ? N2 C19 C11 . . 123.4(2) ? N2 C19 C18 . . 116.38(16) ? C11 C19 C18 . . 120.21(18) ? C21 C20 C1 2_855 . 120.22(16) ? C21 C20 H14 2_855 . 119.1 ? C1 C20 H14 . . 120.6 ? C20 C21 C1 2_855 . 120.34(16) ? C20 C21 H13 2_855 . 119.9 ? C1 C21 H13 . . 119.7 ? #===END data_mo_Cmpd4 _database_code_depnum_ccdc_archive 'CCDC 857313' #TrackingRef '- CuPP2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H14 Cu N2 O6 P2' _chemical_formula_weight 455.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 '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 9.143(3) _cell_length_b 9.400(3) _cell_length_c 11.457(4) _cell_angle_alpha 101.379(7) _cell_angle_beta 91.586(7) _cell_angle_gamma 114.862(6) _cell_volume 869.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description lump _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 462 _exptl_absorpt_coefficient_mu 1.479 _exptl_absorpt_correction_type semi-empirical _exptl_absorpt_correction_T_min 0.6815 _exptl_absorpt_correction_T_max 0.7454 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15494 _diffrn_reflns_av_R_equivalents 0.0152 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4244 _reflns_number_gt 3901 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0300P)^2^+0.5449P] 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 4244 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.002 _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 Cu1 Cu 0.81255(2) 0.55583(2) 0.370584(17) 0.02382(7) Uani 1 1 d . . . P1 P 0.84274(4) 0.28221(5) 0.47920(3) 0.02246(9) Uani 1 1 d . . . P2 P 0.81869(4) 0.34008(4) 0.07954(3) 0.02066(8) Uani 1 1 d . . . O1 O 0.80796(13) 0.42575(13) 0.48303(10) 0.0266(2) Uani 1 1 d . . . O2 O 0.89217(14) 0.22801(15) 0.35500(11) 0.0313(3) Uani 1 1 d . . . O3 O 1.03786(14) 0.70287(15) 0.42047(12) 0.0340(3) Uani 1 1 d . . . O4 O 0.79878(13) 0.46016(14) 0.02009(10) 0.0272(2) Uani 1 1 d . . . O5 O 0.84219(15) 0.38427(14) 0.21526(10) 0.0301(2) Uani 1 1 d . . . O6 O 0.95903(14) 0.29898(14) 0.03213(11) 0.0309(3) Uani 1 1 d . . . N1 N 0.79099(17) 0.69353(17) 0.26563(13) 0.0287(3) Uani 1 1 d . . . N2 N 0.56780(16) 0.45679(17) 0.33534(13) 0.0277(3) Uani 1 1 d . . . C1 C 0.65306(17) 0.11920(18) 0.49113(13) 0.0225(3) Uani 1 1 d . . . C2 C 0.5743(2) -0.0159(2) 0.39745(14) 0.0293(3) Uani 1 1 d . . . C3 C 0.5777(2) 0.1336(2) 0.59367(15) 0.0315(4) Uani 1 1 d . . . C4 C 0.64019(17) 0.14837(17) 0.03440(13) 0.0215(3) Uani 1 1 d . . . C5 C 0.53329(19) 0.09049(19) 0.11654(13) 0.0261(3) Uani 1 1 d . . . C6 C 0.60485(19) 0.05569(19) -0.08282(14) 0.0260(3) Uani 1 1 d . . . C7 C 0.9142(2) 0.8143(2) 0.23581(18) 0.0375(4) Uani 1 1 d . . . C8 C 0.8922(3) 0.8871(2) 0.14718(19) 0.0440(5) Uani 1 1 d . . . C9 C 0.7389(3) 0.8313(3) 0.08788(19) 0.0457(5) Uani 1 1 d . . . C10 C 0.6102(3) 0.7061(3) 0.11782(18) 0.0403(4) Uani 1 1 d . . . C11 C 0.6397(2) 0.6397(2) 0.20802(15) 0.0294(3) Uani 1 1 d . . . C12 C 0.5132(2) 0.5085(2) 0.24997(15) 0.0298(3) Uani 1 1 d . . . C13 C 0.3482(2) 0.4438(3) 0.20902(19) 0.0423(4) Uani 1 1 d . . . C14 C 0.2387(2) 0.3255(3) 0.2586(2) 0.0499(5) Uani 1 1 d . . . C15 C 0.2944(2) 0.2753(3) 0.3470(2) 0.0453(5) Uani 1 1 d . . . C16 C 0.4603(2) 0.3425(2) 0.38295(17) 0.0352(4) Uani 1 1 d . . . H6 H 0.6740 0.0937 -0.1382 0.050 Uiso 1 1 d . . . H7 H 1.0150 0.8538 0.2827 0.050 Uiso 1 1 d . . . H3 H 0.6289 0.2197 0.6562 0.050 Uiso 1 1 d . . . H5 H 0.5549 0.1576 0.1971 0.050 Uiso 1 1 d . . . H16 H 0.5008 0.3107 0.4402 0.050 Uiso 1 1 d . . . H9 H 0.7213 0.8869 0.0269 0.050 Uiso 1 1 d . . . H2 H 0.6228 -0.0247 0.3302 0.050 Uiso 1 1 d . . . H14 H 0.1365 0.2988 0.2418 0.050 Uiso 1 1 d . . . H8 H 0.9896 0.9716 0.1284 0.050 Uiso 1 1 d . . . H10 H 0.5005 0.6653 0.0766 0.050 Uiso 1 1 d . . . H13 H 0.3078 0.4796 0.1523 0.050 Uiso 1 1 d . . . H15 H 0.2246 0.2075 0.3889 0.050 Uiso 1 1 d . . . H02 H 0.8750 0.2814 0.3022 0.050 Uiso 1 1 d . . . H06 H 1.0394 0.3834 0.0142 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 Cu1 0.01622(10) 0.02205(10) 0.02859(11) 0.00970(7) -0.00381(7) 0.00269(7) P1 0.01405(16) 0.02065(18) 0.02609(18) 0.01070(14) -0.00199(13) -0.00074(14) P2 0.01874(17) 0.01900(17) 0.02132(17) 0.00667(13) 0.00019(13) 0.00471(14) O1 0.0233(5) 0.0230(5) 0.0285(5) 0.0104(4) 0.0004(4) 0.0036(4) O2 0.0278(6) 0.0322(6) 0.0353(6) 0.0146(5) 0.0090(5) 0.0109(5) O3 0.0198(5) 0.0308(6) 0.0413(7) 0.0202(5) -0.0093(5) -0.0032(5) O4 0.0231(5) 0.0250(5) 0.0335(6) 0.0137(5) 0.0017(4) 0.0077(4) O5 0.0337(6) 0.0271(6) 0.0219(5) 0.0054(4) -0.0025(4) 0.0065(5) O6 0.0234(6) 0.0276(6) 0.0438(7) 0.0136(5) 0.0086(5) 0.0106(5) N1 0.0280(7) 0.0269(7) 0.0309(7) 0.0081(5) -0.0025(5) 0.0113(6) N2 0.0191(6) 0.0296(7) 0.0314(7) 0.0048(5) -0.0010(5) 0.0089(5) C1 0.0154(6) 0.0209(7) 0.0247(7) 0.0091(5) -0.0015(5) 0.0003(5) C2 0.0249(8) 0.0255(8) 0.0260(7) 0.0052(6) 0.0060(6) 0.0004(6) C3 0.0267(8) 0.0231(8) 0.0267(7) 0.0010(6) 0.0014(6) -0.0040(6) C4 0.0200(7) 0.0195(6) 0.0232(7) 0.0070(5) 0.0002(5) 0.0061(5) C5 0.0260(7) 0.0243(7) 0.0208(6) 0.0036(6) 0.0021(6) 0.0049(6) C6 0.0236(7) 0.0255(7) 0.0233(7) 0.0073(6) 0.0046(6) 0.0045(6) C7 0.0371(9) 0.0314(9) 0.0411(10) 0.0145(8) -0.0003(8) 0.0098(7) C8 0.0556(12) 0.0363(10) 0.0464(11) 0.0206(9) 0.0096(9) 0.0211(9) C9 0.0661(14) 0.0479(11) 0.0408(10) 0.0189(9) 0.0044(9) 0.0380(11) C10 0.0468(11) 0.0470(11) 0.0381(9) 0.0100(8) -0.0040(8) 0.0311(9) C11 0.0309(8) 0.0314(8) 0.0298(8) 0.0037(6) -0.0025(6) 0.0190(7) C12 0.0245(8) 0.0341(9) 0.0308(8) 0.0011(7) -0.0031(6) 0.0158(7) C13 0.0281(9) 0.0544(12) 0.0448(10) 0.0057(9) -0.0066(8) 0.0214(9) C14 0.0199(8) 0.0634(14) 0.0579(13) 0.0040(11) -0.0018(8) 0.0149(9) C15 0.0228(8) 0.0493(12) 0.0540(12) 0.0097(9) 0.0090(8) 0.0070(8) C16 0.0248(8) 0.0388(9) 0.0386(9) 0.0097(8) 0.0043(7) 0.0102(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 Cu1 O3 1.9260(12) . ? Cu1 O1 1.9334(12) . ? Cu1 N1 1.9939(14) . ? Cu1 N2 2.0216(15) . ? Cu1 O5 2.2589(13) . ? P1 O1 1.5039(13) . ? P1 O3 1.5068(12) 2_766 ? P1 O2 1.5593(13) . ? P1 C1 1.7987(15) . ? P2 O4 1.4968(12) . ? P2 O5 1.5125(12) . ? P2 O6 1.5694(13) . ? P2 C4 1.8142(16) . ? O2 H02 0.9073 . ? O3 P1 1.5068(12) 2_766 ? O6 H06 0.8912 . ? N1 C7 1.332(2) . ? N1 C11 1.354(2) . ? N2 C16 1.339(2) . ? N2 C12 1.344(2) . ? C1 C3 1.390(2) . ? C1 C2 1.391(2) . ? C2 C3 1.388(2) 2_656 ? C2 H2 0.9062 . ? C3 C2 1.388(2) 2_656 ? C3 H3 0.9065 . ? C4 C5 1.394(2) . ? C4 C6 1.394(2) . ? C5 C6 1.392(2) 2_655 ? C5 H5 0.9716 . ? C6 C5 1.392(2) 2_655 ? C6 H6 0.9228 . ? C7 C8 1.385(3) . ? C7 H7 0.9393 . ? C8 C9 1.374(3) . ? C8 H8 0.9764 . ? C9 C10 1.380(3) . ? C9 H9 0.9979 . ? C10 C11 1.383(2) . ? C10 H10 0.9773 . ? C11 C12 1.468(3) . ? C12 C13 1.394(2) . ? C13 C14 1.381(3) . ? C13 H13 0.9219 . ? C14 C15 1.367(3) . ? C14 H14 0.8641 . ? C15 C16 1.388(3) . ? C15 H15 0.9161 . ? C16 H16 0.9018 . ? 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 Cu1 O1 93.74(5) . . ? O3 Cu1 N1 90.85(6) . . ? O1 Cu1 N1 171.79(5) . . ? O3 Cu1 N2 164.22(6) . . ? O1 Cu1 N2 93.46(5) . . ? N1 Cu1 N2 80.47(6) . . ? O3 Cu1 O5 99.05(6) . . ? O1 Cu1 O5 93.31(5) . . ? N1 Cu1 O5 92.69(6) . . ? N2 Cu1 O5 94.53(5) . . ? O1 P1 O3 116.36(7) . 2_766 ? O1 P1 O2 111.20(7) . . ? O3 P1 O2 110.50(8) 2_766 . ? O1 P1 C1 106.12(7) . . ? O3 P1 C1 106.08(7) 2_766 . ? O2 P1 C1 105.81(7) . . ? O4 P2 O5 115.60(7) . . ? O4 P2 O6 111.15(7) . . ? O5 P2 O6 109.89(7) . . ? O4 P2 C4 109.55(7) . . ? O5 P2 C4 106.67(7) . . ? O6 P2 C4 103.16(7) . . ? P1 O1 Cu1 134.57(8) . . ? P1 O2 H02 110.1 . . ? P1 O3 Cu1 131.73(7) 2_766 . ? P2 O5 Cu1 140.61(7) . . ? P2 O6 H06 112.1 . . ? C7 N1 C11 119.42(15) . . ? C7 N1 Cu1 125.24(12) . . ? C11 N1 Cu1 114.51(12) . . ? C16 N2 C12 118.88(15) . . ? C16 N2 Cu1 126.82(12) . . ? C12 N2 Cu1 114.19(11) . . ? C3 C1 C2 119.01(14) . . ? C3 C1 P1 119.02(12) . . ? C2 C1 P1 121.83(12) . . ? C3 C2 C1 120.21(15) 2_656 . ? C3 C2 H2 120.7 2_656 . ? C1 C2 H2 119.0 . . ? C2 C3 C1 120.78(15) 2_656 . ? C2 C3 H3 119.3 2_656 . ? C1 C3 H3 119.9 . . ? C5 C4 C6 118.13(14) . . ? C5 C4 P2 120.48(11) . . ? C6 C4 P2 121.39(11) . . ? C6 C5 C4 121.06(14) 2_655 . ? C6 C5 H5 120.7 2_655 . ? C4 C5 H5 118.1 . . ? C5 C6 C4 120.81(14) 2_655 . ? C5 C6 H6 120.4 2_655 . ? C4 C6 H6 118.8 . . ? N1 C7 C8 121.83(18) . . ? N1 C7 H7 116.4 . . ? C8 C7 H7 121.5 . . ? C9 C8 C7 118.72(19) . . ? C9 C8 H8 124.6 . . ? C7 C8 H8 116.6 . . ? C8 C9 C10 120.05(17) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 120.8 . . ? C9 C10 C11 118.47(18) . . ? C9 C10 H10 121.0 . . ? C11 C10 H10 120.5 . . ? N1 C11 C10 121.50(18) . . ? N1 C11 C12 114.63(14) . . ? C10 C11 C12 123.86(16) . . ? N2 C12 C13 121.42(17) . . ? N2 C12 C11 114.67(14) . . ? C13 C12 C11 123.88(16) . . ? C14 C13 C12 119.08(18) . . ? C14 C13 H13 118.0 . . ? C12 C13 H13 122.9 . . ? C15 C14 C13 119.32(18) . . ? C15 C14 H14 121.8 . . ? C13 C14 H14 117.9 . . ? C14 C15 C16 119.04(19) . . ? C14 C15 H15 121.5 . . ? C16 C15 H15 119.0 . . ? N2 C16 C15 122.23(18) . . ? N2 C16 H16 116.7 . . ? C15 C16 H16 121.1 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.323 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.051 #===END data_Cmpd5 _database_code_depnum_ccdc_archive 'CCDC 857314' #TrackingRef '- CuPP2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H23 Cu N4 O6 P2' _chemical_formula_weight 661.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 26.9341(8) _cell_length_b 8.4997(2) _cell_length_c 26.9792(8) _cell_angle_alpha 90.00 _cell_angle_beta 117.0430(10) _cell_angle_gamma 90.00 _cell_volume 5501.1(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8742 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Lump _exptl_crystal_colour Black _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2704 _exptl_absorpt_coefficient_mu 0.965 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6690 _exptl_absorpt_correction_T_max 0.7455 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25175 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.13 _reflns_number_total 6064 _reflns_number_gt 4398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker APEX2' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 2008)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _computing_publication_material 'Bruker APEX2' _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^)+(0.0541P)^2^+1.8747P] 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 6064 _refine_ls_number_parameters 389 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 Cu1 Cu 0.261555(13) 0.49347(4) 0.227930(14) 0.04984(13) Uani 1 1 d . . . P1 P 0.38135(2) 0.73106(7) 0.07922(3) 0.03213(16) Uani 1 1 d . . . P2 P 0.39901(2) 0.18490(7) 0.12690(3) 0.03297(16) Uani 1 1 d . . . O1 O 0.41074(7) 0.8404(2) 0.05484(7) 0.0414(4) Uani 1 1 d . . . O2 O 0.38959(7) 0.78275(19) 0.13532(7) 0.0389(4) Uani 1 1 d . . . O3 O 0.40222(7) 0.5661(2) 0.07652(8) 0.0469(4) Uani 1 1 d . . . H23 H 0.3913 0.5044 0.0928 0.070 Uiso 1 1 calc R . . O4 O 0.41957(7) 0.12239(19) 0.08754(7) 0.0394(4) Uani 1 1 d . . . O5 O 0.35607(6) 0.0712(2) 0.13211(7) 0.0407(4) Uani 1 1 d . . . O6 O 0.37123(7) 0.3441(2) 0.11235(8) 0.0489(5) Uani 1 1 d . . . N1 N 0.22994(8) 0.3789(2) 0.15268(9) 0.0402(5) Uani 1 1 d . . . N2 N 0.17893(8) 0.5503(2) 0.19914(9) 0.0414(5) Uani 1 1 d . . . N3 N 0.34234(8) 0.5710(2) 0.26157(8) 0.0388(5) Uani 1 1 d . . . N4 N 0.28728(9) 0.4266(3) 0.30980(9) 0.0440(5) Uani 1 1 d . . . C1 C 0.25565(11) 0.3008(3) 0.12796(12) 0.0498(7) Uani 1 1 d . . . C2 C 0.22779(12) 0.2321(4) 0.07546(12) 0.0561(8) Uani 1 1 d . . . C3 C 0.17111(13) 0.2461(3) 0.04668(12) 0.0549(7) Uani 1 1 d . . . C4 C 0.14212(11) 0.3301(3) 0.07037(11) 0.0440(6) Uani 1 1 d . . . C5 C 0.17358(9) 0.3950(3) 0.12329(10) 0.0370(5) Uani 1 1 d . . . C6 C 0.08281(12) 0.3500(4) 0.04340(12) 0.0588(8) Uani 1 1 d . . . C7 C 0.05719(11) 0.4281(4) 0.06851(12) 0.0584(8) Uani 1 1 d . . . C8 C 0.08783(11) 0.4984(3) 0.12204(12) 0.0455(6) Uani 1 1 d . . . C9 C 0.14629(10) 0.4833(3) 0.14938(11) 0.0363(6) Uani 1 1 d . . . C10 C 0.06322(11) 0.5842(4) 0.14966(13) 0.0555(8) Uani 1 1 d . . . C11 C 0.09596(13) 0.6470(4) 0.20012(15) 0.0583(8) Uani 1 1 d . . . C12 C 0.15357(12) 0.6295(3) 0.22373(12) 0.0508(7) Uani 1 1 d . . . C13 C 0.37020(11) 0.6386(3) 0.23711(12) 0.0477(7) Uani 1 1 d . . . C14 C 0.42662(11) 0.6744(3) 0.26505(13) 0.0540(7) Uani 1 1 d . . . C15 C 0.45610(11) 0.6359(3) 0.31949(13) 0.0541(7) Uani 1 1 d . . . C16 C 0.42930(11) 0.5590(3) 0.34684(11) 0.0463(6) Uani 1 1 d . . . C17 C 0.37188(10) 0.5303(3) 0.31571(10) 0.0371(5) Uani 1 1 d . . . C18 C 0.45798(13) 0.5056(4) 0.40322(13) 0.0625(9) Uani 1 1 d . . . C19 C 0.43022(14) 0.4303(4) 0.42704(12) 0.0661(9) Uani 1 1 d . . . C20 C 0.37128(12) 0.4019(3) 0.39716(11) 0.0502(7) Uani 1 1 d . . . C21 C 0.34235(11) 0.4522(3) 0.34170(10) 0.0388(6) Uani 1 1 d . . . C22 C 0.34031(15) 0.3259(4) 0.41991(13) 0.0669(9) Uani 1 1 d . . . C23 C 0.28449(16) 0.3070(4) 0.38868(15) 0.0682(9) Uani 1 1 d . . . C24 C 0.25911(13) 0.3587(4) 0.33370(13) 0.0571(8) Uani 1 1 d . . . C25 C 0.30785(8) 0.7391(2) 0.03281(9) 0.0278(5) Uani 1 1 d . . . C26 C 0.27420(9) 0.6085(3) 0.02494(10) 0.0338(5) Uani 1 1 d . . . C27 C 0.28328(9) 0.8809(3) 0.00752(10) 0.0332(5) Uani 1 1 d . . . C28 C 0.45636(9) 0.1929(3) 0.19589(9) 0.0296(5) Uani 1 1 d . . . C29 C 0.47884(9) 0.0523(3) 0.22345(10) 0.0348(5) Uani 1 1 d . . . C30 C 0.47810(10) 0.3342(3) 0.22308(10) 0.0366(5) Uani 1 1 d . . . H1 H 0.2990 0.2948 0.1509 0.080 Uiso 1 1 d . . . H2 H 0.2521 0.1674 0.0616 0.080 Uiso 1 1 d . . . H3 H 0.1515 0.2132 0.0073 0.080 Uiso 1 1 d . . . H4 H 0.0605 0.2976 0.0042 0.080 Uiso 1 1 d . . . H5 H 0.0164 0.4430 0.0495 0.080 Uiso 1 1 d . . . H6 H 0.0210 0.5873 0.1302 0.080 Uiso 1 1 d . . . H7 H 0.0808 0.7081 0.2199 0.080 Uiso 1 1 d . . . H8 H 0.1824 0.6742 0.2617 0.080 Uiso 1 1 d . . . H9 H 0.3483 0.6739 0.1992 0.080 Uiso 1 1 d . . . H10 H 0.4461 0.7209 0.2425 0.080 Uiso 1 1 d . . . H11 H 0.4978 0.6595 0.3428 0.080 Uiso 1 1 d . . . H12 H 0.4996 0.5220 0.4238 0.080 Uiso 1 1 d . . . H13 H 0.4484 0.3842 0.4646 0.080 Uiso 1 1 d . . . H14 H 0.3598 0.2850 0.4595 0.080 Uiso 1 1 d . . . H15 H 0.2612 0.2701 0.4059 0.080 Uiso 1 1 d . . . H16 H 0.2195 0.3451 0.3123 0.080 Uiso 1 1 d . . . H17 H 0.2890 0.5099 0.0427 0.080 Uiso 1 1 d . . . H18 H 0.3079 0.9761 0.0109 0.080 Uiso 1 1 d . . . H19 H 0.4662 -0.0479 0.2060 0.080 Uiso 1 1 d . . . H20 H 0.4640 0.4390 0.2049 0.080 Uiso 1 1 d . . . H21 H 0.3658 -0.0258 0.1383 0.080 Uiso 1 1 d . . . H22 H 0.4115 0.9544 0.0651 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 Cu1 0.03120(18) 0.0716(3) 0.0404(2) -0.00084(16) 0.01071(15) -0.00155(15) P1 0.0243(3) 0.0340(3) 0.0330(3) 0.0017(3) 0.0086(3) 0.0022(2) P2 0.0273(3) 0.0330(3) 0.0335(3) 0.0049(3) 0.0093(3) 0.0051(2) O1 0.0363(9) 0.0446(10) 0.0468(11) 0.0010(8) 0.0221(8) -0.0036(7) O2 0.0410(9) 0.0406(9) 0.0272(9) 0.0010(7) 0.0086(7) -0.0026(7) O3 0.0346(9) 0.0382(9) 0.0647(13) 0.0039(9) 0.0199(9) 0.0084(8) O4 0.0424(9) 0.0424(9) 0.0338(9) 0.0002(7) 0.0178(8) -0.0020(7) O5 0.0289(8) 0.0430(9) 0.0488(11) 0.0031(8) 0.0165(8) 0.0002(7) O6 0.0420(10) 0.0406(10) 0.0555(12) 0.0121(8) 0.0148(9) 0.0152(8) N1 0.0303(10) 0.0507(12) 0.0393(12) 0.0011(10) 0.0155(9) 0.0067(9) N2 0.0346(11) 0.0485(12) 0.0443(13) -0.0049(10) 0.0207(10) -0.0005(9) N3 0.0323(10) 0.0487(12) 0.0364(12) 0.0058(10) 0.0165(9) -0.0013(9) N4 0.0426(12) 0.0516(13) 0.0439(13) 0.0002(10) 0.0249(11) -0.0074(10) C1 0.0409(14) 0.0654(18) 0.0445(16) 0.0054(13) 0.0207(13) 0.0162(13) C2 0.0591(18) 0.0663(19) 0.0456(17) 0.0006(14) 0.0261(15) 0.0180(15) C3 0.0628(19) 0.0606(18) 0.0386(16) -0.0023(13) 0.0207(15) 0.0066(15) C4 0.0417(14) 0.0514(15) 0.0353(14) 0.0039(12) 0.0145(12) 0.0006(12) C5 0.0325(12) 0.0403(13) 0.0373(14) 0.0069(11) 0.0152(11) 0.0038(10) C6 0.0444(16) 0.080(2) 0.0408(16) -0.0020(15) 0.0095(14) -0.0036(15) C7 0.0297(14) 0.086(2) 0.0484(18) 0.0071(16) 0.0083(13) 0.0018(14) C8 0.0335(13) 0.0570(17) 0.0479(16) 0.0099(13) 0.0201(12) 0.0042(11) C9 0.0296(12) 0.0423(13) 0.0390(14) 0.0060(11) 0.0173(11) 0.0022(10) C10 0.0346(14) 0.073(2) 0.067(2) 0.0057(16) 0.0298(15) 0.0074(14) C11 0.0565(18) 0.0617(19) 0.078(2) 0.0028(17) 0.0497(18) 0.0101(15) C12 0.0497(16) 0.0537(16) 0.0587(18) -0.0045(14) 0.0333(15) 0.0012(13) C13 0.0434(15) 0.0525(16) 0.0515(17) 0.0135(13) 0.0254(13) 0.0040(12) C14 0.0435(15) 0.0573(17) 0.067(2) 0.0097(15) 0.0302(15) -0.0029(13) C15 0.0347(14) 0.0565(17) 0.066(2) -0.0068(15) 0.0180(14) -0.0117(12) C16 0.0386(14) 0.0509(15) 0.0421(16) -0.0057(13) 0.0118(12) -0.0043(12) C17 0.0369(13) 0.0386(13) 0.0351(14) -0.0016(10) 0.0157(11) -0.0023(10) C18 0.0470(17) 0.082(2) 0.0403(17) -0.0065(15) 0.0041(14) -0.0050(15) C19 0.062(2) 0.086(2) 0.0326(16) 0.0034(16) 0.0053(15) 0.0069(18) C20 0.0634(18) 0.0567(17) 0.0317(14) -0.0002(12) 0.0226(14) 0.0028(14) C21 0.0426(14) 0.0432(14) 0.0325(13) -0.0026(11) 0.0186(12) -0.0023(11) C22 0.087(3) 0.079(2) 0.0446(18) 0.0078(16) 0.0382(19) 0.0036(19) C23 0.094(3) 0.073(2) 0.066(2) 0.0092(17) 0.061(2) -0.0075(19) C24 0.0607(18) 0.0629(19) 0.063(2) 0.0002(15) 0.0419(17) -0.0125(15) C25 0.0259(10) 0.0334(12) 0.0233(11) -0.0010(9) 0.0105(9) 0.0020(9) C26 0.0313(12) 0.0288(12) 0.0352(13) 0.0036(10) 0.0099(10) 0.0045(9) C27 0.0296(11) 0.0295(12) 0.0359(13) 0.0010(10) 0.0111(10) -0.0003(9) C28 0.0266(11) 0.0314(11) 0.0316(12) 0.0013(9) 0.0140(10) 0.0028(9) C29 0.0322(12) 0.0270(11) 0.0359(13) -0.0014(10) 0.0074(10) 0.0013(9) C30 0.0386(13) 0.0272(11) 0.0417(14) 0.0022(10) 0.0161(11) 0.0022(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 2.0485(19) . ? Cu1 N2 2.054(2) . ? Cu1 N1 2.055(2) . ? Cu1 N4 2.071(2) . ? P1 O2 1.4924(17) . ? P1 O3 1.5244(17) . ? P1 O1 1.5484(17) . ? P1 C25 1.799(2) . ? P2 O4 1.5003(17) . ? P2 O6 1.5090(17) . ? P2 O5 1.5622(17) . ? P2 C28 1.800(2) . ? N1 C1 1.336(3) . ? N1 C5 1.363(3) . ? N2 C12 1.331(3) . ? N2 C9 1.351(3) . ? N3 C13 1.334(3) . ? N3 C17 1.352(3) . ? N4 C24 1.330(3) . ? N4 C21 1.352(3) . ? C1 C2 1.394(4) . ? C2 C3 1.367(4) . ? C3 C4 1.408(4) . ? C4 C5 1.400(4) . ? C4 C6 1.433(4) . ? C5 C9 1.438(3) . ? C6 C7 1.342(4) . ? C7 C8 1.428(4) . ? C8 C10 1.406(4) . ? C8 C9 1.408(3) . ? C10 C11 1.351(4) . ? C11 C12 1.392(4) . ? C13 C14 1.389(4) . ? C14 C15 1.354(4) . ? C15 C16 1.406(4) . ? C16 C17 1.406(3) . ? C16 C18 1.431(4) . ? C17 C21 1.440(3) . ? C18 C19 1.348(5) . ? C19 C20 1.437(4) . ? C20 C22 1.398(4) . ? C20 C21 1.403(4) . ? C22 C23 1.358(5) . ? C23 C24 1.392(5) . ? C25 C26 1.387(3) . ? C25 C27 1.395(3) . ? C26 C27 1.393(3) 7_565 ? C27 C26 1.393(3) 7_565 ? C28 C30 1.390(3) . ? C28 C29 1.393(3) . ? C29 C29 1.366(4) 2_655 ? C30 C30 1.394(5) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N2 147.36(9) . . ? N3 Cu1 N1 118.01(8) . . ? N2 Cu1 N1 81.18(8) . . ? N3 Cu1 N4 80.95(8) . . ? N2 Cu1 N4 104.32(8) . . ? N1 Cu1 N4 135.32(9) . . ? O2 P1 O3 115.54(10) . . ? O2 P1 O1 112.64(10) . . ? O3 P1 O1 105.12(10) . . ? O2 P1 C25 107.70(10) . . ? O3 P1 C25 108.33(10) . . ? O1 P1 C25 107.15(10) . . ? O4 P2 O6 115.61(10) . . ? O4 P2 O5 111.78(10) . . ? O6 P2 O5 106.16(10) . . ? O4 P2 C28 109.02(9) . . ? O6 P2 C28 109.02(10) . . ? O5 P2 C28 104.63(10) . . ? C1 N1 C5 116.9(2) . . ? C1 N1 Cu1 130.74(17) . . ? C5 N1 Cu1 112.26(16) . . ? C12 N2 C9 117.3(2) . . ? C12 N2 Cu1 130.08(19) . . ? C9 N2 Cu1 112.35(15) . . ? C13 N3 C17 117.2(2) . . ? C13 N3 Cu1 129.98(18) . . ? C17 N3 Cu1 112.41(15) . . ? C24 N4 C21 117.6(2) . . ? C24 N4 Cu1 130.4(2) . . ? C21 N4 Cu1 111.91(16) . . ? N1 C1 C2 123.6(2) . . ? C3 C2 C1 119.1(3) . . ? C2 C3 C4 119.5(3) . . ? C5 C4 C3 117.3(2) . . ? C5 C4 C6 119.3(2) . . ? C3 C4 C6 123.4(3) . . ? N1 C5 C4 123.5(2) . . ? N1 C5 C9 116.7(2) . . ? C4 C5 C9 119.8(2) . . ? C7 C6 C4 120.8(3) . . ? C6 C7 C8 121.6(2) . . ? C10 C8 C9 117.0(3) . . ? C10 C8 C7 123.9(3) . . ? C9 C8 C7 119.1(2) . . ? N2 C9 C8 123.3(2) . . ? N2 C9 C5 117.4(2) . . ? C8 C9 C5 119.3(2) . . ? C11 C10 C8 119.4(2) . . ? C10 C11 C12 120.0(3) . . ? N2 C12 C11 123.0(3) . . ? N3 C13 C14 123.3(3) . . ? C15 C14 C13 119.5(3) . . ? C14 C15 C16 119.6(2) . . ? C17 C16 C15 117.1(2) . . ? C17 C16 C18 119.7(3) . . ? C15 C16 C18 123.2(3) . . ? N3 C17 C16 123.2(2) . . ? N3 C17 C21 117.4(2) . . ? C16 C17 C21 119.4(2) . . ? C19 C18 C16 120.6(3) . . ? C18 C19 C20 121.5(3) . . ? C22 C20 C21 117.1(3) . . ? C22 C20 C19 124.0(3) . . ? C21 C20 C19 118.9(3) . . ? N4 C21 C20 123.1(2) . . ? N4 C21 C17 117.0(2) . . ? C20 C21 C17 119.9(2) . . ? C23 C22 C20 119.7(3) . . ? C22 C23 C24 119.5(3) . . ? N4 C24 C23 122.8(3) . . ? C26 C25 C27 119.02(19) . . ? C26 C25 P1 120.79(16) . . ? C27 C25 P1 120.01(16) . . ? C25 C26 C27 120.4(2) . 7_565 ? C26 C27 C25 120.6(2) 7_565 . ? C30 C28 C29 118.9(2) . . ? C30 C28 P2 122.40(17) . . ? C29 C28 P2 118.69(17) . . ? C29 C29 C28 120.85(13) 2_655 . ? C28 C30 C30 120.24(13) . 2_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.13 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.275 _refine_diff_density_min -0.520 _refine_diff_density_rms 0.059 #===END