# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email wxt@fjirsm.ac.cn _publ_contact_author_name 'Xintao Wu' loop_ _publ_author_name 'Ruibiao Fu' 'Shengmin Hu' 'Xintao Wu' data_f1 _database_code_depnum_ccdc_archive 'CCDC 773345' #TrackingRef '- 1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 N O8 P2 Zn2' _chemical_formula_weight 427.83 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)/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 5.579(3) _cell_length_b 12.653(6) _cell_length_c 16.384(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.977(10) _cell_angle_gamma 90.00 _cell_volume 1150.3(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2608 _cell_measurement_theta_min 3.2199 _cell_measurement_theta_max 27.4487 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 4.488 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6173 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8785 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2616 _reflns_number_gt 2167 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0315P)^2^+5.1657P] 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 2616 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.08082(11) 0.17342(5) 0.21725(4) 0.01866(19) Uani 1 1 d . . . Zn2 Zn 0.23142(11) -0.08335(5) 0.44331(4) 0.01720(18) Uani 1 1 d . . . P1 P 0.0109(2) 0.15106(11) 0.40361(9) 0.0130(3) Uani 1 1 d . . . P2 P 0.2697(2) 0.20927(11) 0.57283(9) 0.0135(3) Uani 1 1 d . . . O1 O -0.0575(7) 0.1943(3) 0.3178(2) 0.0167(8) Uani 1 1 d . . . O2 O 0.1742(7) 0.0559(3) 0.4020(3) 0.0212(9) Uani 1 1 d . . . O3 O -0.2179(6) 0.1299(3) 0.4438(2) 0.0176(8) Uani 1 1 d . . . O4 O 0.0329(6) 0.1772(3) 0.6060(2) 0.0167(8) Uani 1 1 d . . . O5 O 0.4419(6) 0.1182(3) 0.5731(3) 0.0232(9) Uani 1 1 d . . . O6 O 0.3791(7) 0.3056(3) 0.6177(3) 0.0252(10) Uani 1 1 d . . . O7 O 0.4068(6) 0.2718(3) 0.4252(2) 0.0193(9) Uani 1 1 d . . . H3 H 0.5023 0.2233 0.4361 0.029 Uiso 1 1 calc R . . O8 O 0.3256(9) 0.2902(4) 0.2404(3) 0.0308(11) Uani 1 1 d . . . H1 H 0.436(15) 0.281(7) 0.214(5) 0.05(3) Uiso 1 1 d . . . H2 H 0.40(2) 0.287(11) 0.295(9) 0.16(6) Uiso 1 1 d . . . N1 N 0.1979(8) 0.5505(4) 0.3007(3) 0.0207(11) Uani 1 1 d . . . C1 C 0.1906(9) 0.2533(4) 0.4650(3) 0.0132(11) Uani 1 1 d . . . C2 C 0.0605(10) 0.3606(4) 0.4685(3) 0.0170(12) Uani 1 1 d . . . H4 H -0.0994 0.3479 0.4847 0.020 Uiso 1 1 calc R . . H5 H 0.1472 0.4032 0.5111 0.020 Uiso 1 1 calc R . . C3 C 0.0351(10) 0.4239(4) 0.3897(4) 0.0170(12) Uani 1 1 d . . . C4 C 0.2134(9) 0.4940(4) 0.3707(4) 0.0174(12) Uani 1 1 d . . . H6 H 0.3494 0.5023 0.4081 0.021 Uiso 1 1 calc R . . C5 C -0.1700(10) 0.4175(4) 0.3337(4) 0.0205(12) Uani 1 1 d . . . H7 H -0.2982 0.3751 0.3454 0.025 Uiso 1 1 calc R . . C6 C -0.1852(11) 0.4733(5) 0.2612(4) 0.0241(13) Uani 1 1 d . . . H8 H -0.3203 0.4674 0.2231 0.029 Uiso 1 1 calc R . . C7 C 0.0027(10) 0.5377(5) 0.2463(4) 0.0222(13) Uani 1 1 d . . . H9 H -0.0052 0.5739 0.1967 0.027 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 0.0203(3) 0.0196(4) 0.0158(4) -0.0013(3) 0.0009(3) 0.0032(3) Zn2 0.0147(3) 0.0175(3) 0.0198(4) 0.0048(3) 0.0040(3) 0.0023(2) P1 0.0147(6) 0.0111(6) 0.0134(7) 0.0004(5) 0.0020(5) 0.0003(5) P2 0.0118(6) 0.0144(7) 0.0140(7) 0.0031(6) 0.0001(5) -0.0001(5) O1 0.0220(19) 0.0177(19) 0.010(2) -0.0019(16) 0.0013(16) -0.0009(15) O2 0.0220(19) 0.016(2) 0.026(2) 0.0008(17) 0.0053(17) 0.0046(16) O3 0.0124(17) 0.023(2) 0.017(2) 0.0012(17) 0.0032(15) -0.0034(16) O4 0.0163(18) 0.023(2) 0.012(2) 0.0033(16) 0.0052(15) -0.0003(16) O5 0.0148(18) 0.027(2) 0.029(2) 0.0114(19) 0.0054(17) 0.0058(17) O6 0.032(2) 0.022(2) 0.019(2) 0.0024(18) -0.0068(18) -0.0074(18) O7 0.0149(18) 0.022(2) 0.022(2) 0.0077(17) 0.0078(16) 0.0015(16) O8 0.033(3) 0.032(3) 0.028(3) -0.002(2) 0.005(2) -0.010(2) N1 0.020(2) 0.022(2) 0.020(3) 0.005(2) 0.001(2) -0.003(2) C1 0.014(2) 0.013(3) 0.012(3) 0.003(2) 0.003(2) 0.000(2) C2 0.023(3) 0.013(3) 0.014(3) 0.000(2) 0.000(2) 0.003(2) C3 0.021(3) 0.010(2) 0.019(3) 0.000(2) 0.000(2) 0.004(2) C4 0.014(2) 0.016(3) 0.021(3) 0.002(2) 0.001(2) 0.002(2) C5 0.020(3) 0.018(3) 0.024(3) 0.002(2) 0.001(2) -0.002(2) C6 0.024(3) 0.021(3) 0.025(3) 0.003(3) -0.008(3) -0.004(2) C7 0.028(3) 0.019(3) 0.020(3) 0.004(2) 0.001(3) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O6 1.902(4) 4_565 ? Zn1 O1 1.909(4) . ? Zn1 O8 2.021(5) . ? Zn1 N1 2.026(5) 2_545 ? Zn2 O2 1.903(4) . ? Zn2 O5 1.921(4) 3_656 ? Zn2 O3 1.950(4) 3_556 ? Zn2 O4 1.998(4) 3_556 ? P1 O2 1.512(4) . ? P1 O1 1.520(4) . ? P1 O3 1.520(4) . ? P1 C1 1.866(5) . ? P2 O5 1.500(4) . ? P2 O6 1.518(4) . ? P2 O4 1.534(4) . ? P2 C1 1.861(6) . ? O3 Zn2 1.950(4) 3_556 ? O4 Zn2 1.998(4) 3_556 ? O5 Zn2 1.921(4) 3_656 ? O6 Zn1 1.902(4) 4_666 ? O7 C1 1.448(6) . ? N1 C7 1.343(7) . ? N1 C4 1.347(7) . ? N1 Zn1 2.026(5) 2 ? C1 C2 1.544(7) . ? C2 C3 1.514(8) . ? C3 C4 1.392(8) . ? C3 C5 1.392(8) . ? C5 C6 1.377(8) . ? C6 C7 1.370(8) . ? 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 O6 Zn1 O1 117.71(17) 4_565 . ? O6 Zn1 O8 112.8(2) 4_565 . ? O1 Zn1 O8 93.6(2) . . ? O6 Zn1 N1 107.32(19) 4_565 2_545 ? O1 Zn1 N1 122.58(19) . 2_545 ? O8 Zn1 N1 100.3(2) . 2_545 ? O2 Zn2 O5 106.78(17) . 3_656 ? O2 Zn2 O3 126.55(17) . 3_556 ? O5 Zn2 O3 101.23(16) 3_656 3_556 ? O2 Zn2 O4 108.51(16) . 3_556 ? O5 Zn2 O4 118.57(17) 3_656 3_556 ? O3 Zn2 O4 95.98(15) 3_556 3_556 ? O2 P1 O1 111.3(2) . . ? O2 P1 O3 113.7(2) . . ? O1 P1 O3 108.9(2) . . ? O2 P1 C1 105.7(2) . . ? O1 P1 C1 108.5(2) . . ? O3 P1 C1 108.5(2) . . ? O5 P2 O6 113.0(2) . . ? O5 P2 O4 111.7(2) . . ? O6 P2 O4 111.0(2) . . ? O5 P2 C1 108.8(2) . . ? O6 P2 C1 105.2(2) . . ? O4 P2 C1 106.7(2) . . ? P1 O1 Zn1 131.6(2) . . ? P1 O2 Zn2 144.1(3) . . ? P1 O3 Zn2 125.5(2) . 3_556 ? P2 O4 Zn2 129.9(2) . 3_556 ? P2 O5 Zn2 142.4(3) . 3_656 ? P2 O6 Zn1 134.4(3) . 4_666 ? C7 N1 C4 118.5(5) . . ? C7 N1 Zn1 117.4(4) . 2 ? C4 N1 Zn1 123.0(4) . 2 ? O7 C1 C2 106.9(4) . . ? O7 C1 P2 110.5(3) . . ? C2 C1 P2 107.1(4) . . ? O7 C1 P1 107.2(4) . . ? C2 C1 P1 113.7(4) . . ? P2 C1 P1 111.4(3) . . ? C3 C2 C1 115.9(5) . . ? C4 C3 C5 116.6(5) . . ? C4 C3 C2 121.5(5) . . ? C5 C3 C2 121.9(5) . . ? N1 C4 C3 123.0(5) . . ? C6 C5 C3 120.7(5) . . ? C7 C6 C5 118.7(5) . . ? N1 C7 C6 122.4(6) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H3 O3 0.82 1.95 2.751(5) 164.7 1_655 O8 H1 O4 0.80(9) 1.98(9) 2.625(7) 138(8) 4_665 O8 H2 O7 0.96(14) 2.13(14) 3.024(7) 154(11) . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.822 _refine_diff_density_min -0.899 _refine_diff_density_rms 0.162 # Attachment '- 2.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 773346' #TrackingRef '- 2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24.50 Cu4 N2 O19.25 P4' _chemical_formula_weight 906.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.741(9) _cell_length_b 11.109(9) _cell_length_c 11.933(11) _cell_angle_alpha 77.678(19) _cell_angle_beta 84.65(3) _cell_angle_gamma 75.99(2) _cell_volume 1348(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2945 _cell_measurement_theta_min 2.3326 _cell_measurement_theta_max 27.4719 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.2000 _exptl_crystal_size_min 0.0800 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.234 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 905 _exptl_absorpt_coefficient_mu 3.441 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.6863 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10248 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0697 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 27.55 _reflns_number_total 5895 _reflns_number_gt 4035 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1239P)^2^+51.2984P] 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 5895 _refine_ls_number_parameters 397 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1286 _refine_ls_R_factor_gt 0.0961 _refine_ls_wR_factor_ref 0.3059 _refine_ls_wR_factor_gt 0.2824 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.45385(14) -0.00692(13) 0.19766(13) 0.0182(4) Uani 1 1 d . . . Cu2 Cu 0.52193(15) 0.24335(14) 0.06587(12) 0.0214(4) Uani 1 1 d . . . Cu3 Cu 0.50959(14) 0.41749(13) 0.33146(12) 0.0149(4) Uani 0.95 1 d P . . Cu4 Cu 0.9698(2) -0.21568(19) -0.06598(18) 0.0423(5) Uani 1 1 d . . . P1 P 0.5760(3) 0.1298(3) 0.3361(2) 0.0147(6) Uani 1 1 d . . . P2 P 0.7531(3) 0.2749(3) 0.1915(3) 0.0189(6) Uani 1 1 d . . . P3 P 0.5124(3) -0.3030(3) 0.1962(3) 0.0166(6) Uani 1 1 d . . . P4 P 0.6872(3) -0.1518(3) 0.0561(3) 0.0166(6) Uani 1 1 d . . . O1 O 0.5109(7) 0.1454(7) 0.2223(7) 0.0150(15) Uani 1 1 d . . . O2 O 0.5273(9) 0.2399(7) 0.3941(7) 0.0206(18) Uani 1 1 d . . . O3 O 0.5630(8) 0.0030(7) 0.4093(7) 0.0205(18) Uani 1 1 d . . . O4 O 0.6806(9) 0.3846(8) 0.2475(8) 0.0245(19) Uani 1 1 d . . . O5 O 0.6935(9) 0.2660(9) 0.0832(8) 0.027(2) Uani 1 1 d . . . O6 O 0.8930(9) 0.2789(8) 0.1703(8) 0.0257(19) Uani 1 1 d . . . O7 O 0.8013(9) 0.0186(8) 0.2438(8) 0.0229(18) Uani 1 1 d . . . H13 H 0.8675 0.0297 0.2073 0.034 Uiso 1 1 calc R . . O8 O 0.5008(8) -0.4050(7) 0.2998(7) 0.0200(17) Uani 1 1 d . . . O9 O 0.4312(9) -0.1745(8) 0.2141(9) 0.028(2) Uani 1 1 d . . . O10 O 0.4779(10) -0.3379(9) 0.0877(7) 0.028(2) Uani 1 1 d . . . O11 O 0.6200(8) -0.0373(7) 0.1081(8) 0.0226(18) Uani 1 1 d . . . O12 O 0.8268(9) -0.1492(9) 0.0267(8) 0.027(2) Uani 1 1 d . . . O13 O 0.6199(9) -0.1651(8) -0.0463(7) 0.0225(18) Uani 1 1 d . . . O14 O 0.7551(9) -0.4023(8) 0.1311(8) 0.0254(19) Uani 1 1 d . . . H14 H 0.8023 -0.3807 0.0763 0.038 Uiso 1 1 calc R . . O15 O 0.9228(17) -0.3825(15) -0.0443(15) 0.077(4) Uani 1 1 d U . . O16 O 0.982(2) -0.0380(19) -0.1221(19) 0.103(6) Uani 1 1 d U . . O17 O 1.106(2) -0.274(2) 0.084(2) 0.121(8) Uani 1 1 d U . . O18 O 1.148(3) -0.510(3) 0.193(3) 0.169(12) Uani 1 1 d U . . O19 O 0.4113(12) 0.4275(10) 0.1490(11) 0.046(3) Uani 1 1 d . . . O20 O 0.860(5) 0.154(4) -0.234(4) 0.049(13) Uani 0.25 1 d P . . N1 N 0.7018(10) -0.0362(9) 0.6925(8) 0.018(2) Uani 1 1 d . . . N2 N 0.6481(11) -0.4493(10) 0.5608(8) 0.022(2) Uani 1 1 d . . . C1 C 0.7452(12) 0.1263(10) 0.2963(10) 0.018(2) Uani 1 1 d . . . C2 C 0.8231(13) 0.1187(13) 0.4024(11) 0.025(3) Uani 1 1 d . . . H1 H 0.9136 0.1039 0.3790 0.030 Uiso 1 1 calc R . . H2 H 0.7994 0.2004 0.4251 0.030 Uiso 1 1 calc R . . C3 C 0.8055(12) 0.0178(12) 0.5070(12) 0.024(3) Uani 1 1 d . . . C4 C 0.7249(12) 0.0482(11) 0.5987(11) 0.021(2) Uani 1 1 d . . . H3 H 0.6838 0.1328 0.5955 0.026 Uiso 1 1 calc R . . C5 C 0.7620(13) -0.1568(12) 0.6957(11) 0.027(3) Uani 1 1 d . . . H4 H 0.7469 -0.2169 0.7596 0.032 Uiso 1 1 calc R . . C6 C 0.8435(15) -0.1962(13) 0.6112(14) 0.036(3) Uani 1 1 d . . . H5 H 0.8843 -0.2813 0.6179 0.044 Uiso 1 1 calc R . . C7 C 0.8663(14) -0.1075(12) 0.5125(12) 0.029(3) Uani 1 1 d . . . H6 H 0.9211 -0.1329 0.4525 0.035 Uiso 1 1 calc R . . C8 C 0.6818(12) -0.2911(10) 0.1726(10) 0.019(2) Uani 1 1 d . . . C9 C 0.7489(13) -0.2733(12) 0.2756(10) 0.022(3) Uani 1 1 d . . . H7 H 0.8362 -0.2671 0.2511 0.027 Uiso 1 1 calc R . . H8 H 0.7045 -0.1938 0.2969 0.027 Uiso 1 1 calc R . . C10 C 0.7530(12) -0.3777(11) 0.3804(10) 0.019(2) Uani 1 1 d . . . C11 C 0.8503(15) -0.4858(13) 0.3990(12) 0.033(3) Uani 1 1 d . . . H12 H 0.9175 -0.4996 0.3447 0.039 Uiso 1 1 calc R . . C12 C 0.8456(14) -0.5732(14) 0.4999(13) 0.036(3) Uani 1 1 d . . . H10 H 0.9120 -0.6450 0.5150 0.043 Uiso 1 1 calc R . . C13 C 0.7438(14) -0.5554(13) 0.5783(12) 0.031(3) Uani 1 1 d . . . H11 H 0.7406 -0.6169 0.6443 0.038 Uiso 1 1 calc R . . C14 C 0.6554(13) -0.3630(11) 0.4653(10) 0.021(2) Uani 1 1 d . . . H9 H 0.5916 -0.2887 0.4548 0.025 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 Cu1 0.0211(8) 0.0126(7) 0.0206(7) -0.0036(5) 0.0042(6) -0.0053(5) Cu2 0.0273(8) 0.0235(8) 0.0141(7) 0.0019(5) 0.0008(6) -0.0126(6) Cu3 0.0193(8) 0.0107(7) 0.0135(7) -0.0014(5) 0.0059(6) -0.0046(5) Cu4 0.0406(11) 0.0402(11) 0.0450(12) -0.0087(9) 0.0088(9) -0.0110(9) P1 0.0192(14) 0.0127(13) 0.0119(13) -0.0028(10) 0.0032(11) -0.0044(10) P2 0.0233(16) 0.0149(14) 0.0185(15) -0.0012(11) 0.0045(12) -0.0082(11) P3 0.0218(15) 0.0127(13) 0.0143(14) 0.0009(10) 0.0022(12) -0.0061(11) P4 0.0220(15) 0.0116(13) 0.0156(14) -0.0012(10) 0.0033(12) -0.0054(11) O1 0.015(4) 0.018(4) 0.013(4) -0.003(3) -0.001(3) -0.006(3) O2 0.031(5) 0.012(4) 0.017(4) -0.004(3) 0.010(4) -0.006(3) O3 0.029(5) 0.013(4) 0.019(4) -0.001(3) 0.005(4) -0.007(3) O4 0.024(5) 0.013(4) 0.032(5) -0.003(3) 0.009(4) -0.002(3) O5 0.031(5) 0.033(5) 0.019(4) -0.004(4) 0.004(4) -0.015(4) O6 0.029(5) 0.022(4) 0.025(5) -0.002(4) 0.009(4) -0.011(4) O7 0.028(5) 0.018(4) 0.023(4) -0.008(3) 0.004(4) -0.005(3) O8 0.029(5) 0.012(4) 0.017(4) 0.003(3) 0.007(4) -0.009(3) O9 0.023(5) 0.018(4) 0.045(6) -0.012(4) 0.010(4) -0.005(3) O10 0.042(6) 0.029(5) 0.015(4) -0.002(4) -0.002(4) -0.014(4) O11 0.022(4) 0.010(4) 0.032(5) -0.005(3) 0.011(4) -0.002(3) O12 0.026(5) 0.026(5) 0.026(5) -0.006(4) 0.011(4) -0.008(4) O13 0.039(5) 0.020(4) 0.010(4) 0.001(3) 0.002(4) -0.014(4) O14 0.033(5) 0.016(4) 0.026(5) -0.006(3) 0.010(4) -0.007(4) O15 0.081(8) 0.062(7) 0.090(8) -0.013(6) 0.017(7) -0.026(6) O16 0.104(10) 0.090(9) 0.112(10) -0.015(7) 0.027(8) -0.035(8) O17 0.121(11) 0.131(11) 0.105(10) -0.018(8) -0.003(8) -0.024(8) O18 0.166(14) 0.171(14) 0.167(14) -0.031(9) -0.009(9) -0.036(9) O19 0.062(8) 0.021(5) 0.057(7) -0.010(5) 0.019(6) -0.017(5) O20 0.08(4) 0.04(3) 0.04(2) -0.01(2) -0.01(2) -0.04(3) N1 0.023(5) 0.015(4) 0.017(5) 0.000(4) 0.001(4) -0.008(4) N2 0.030(6) 0.021(5) 0.013(5) 0.003(4) -0.002(4) -0.004(4) C1 0.023(6) 0.013(5) 0.019(6) -0.004(4) -0.003(5) -0.004(4) C2 0.025(7) 0.031(7) 0.020(6) -0.004(5) 0.004(5) -0.014(5) C3 0.019(6) 0.025(6) 0.030(7) -0.006(5) 0.002(5) -0.008(5) C4 0.021(6) 0.019(6) 0.025(6) -0.001(5) -0.006(5) -0.008(5) C5 0.028(7) 0.022(6) 0.023(6) 0.003(5) 0.012(5) -0.004(5) C6 0.044(9) 0.018(6) 0.040(8) -0.003(6) 0.011(7) 0.000(6) C7 0.031(7) 0.020(6) 0.029(7) -0.001(5) 0.002(6) 0.004(5) C8 0.030(7) 0.007(5) 0.017(6) -0.001(4) 0.003(5) -0.003(4) C9 0.029(7) 0.028(6) 0.010(5) 0.005(4) -0.001(5) -0.014(5) C10 0.020(6) 0.024(6) 0.014(5) -0.005(4) 0.000(5) -0.004(5) C11 0.038(8) 0.024(7) 0.024(7) 0.002(5) 0.005(6) 0.008(6) C12 0.030(8) 0.027(7) 0.036(8) 0.007(6) 0.003(6) 0.007(6) C13 0.033(8) 0.030(7) 0.024(7) 0.003(5) 0.007(6) -0.002(6) C14 0.035(7) 0.015(5) 0.013(5) -0.003(4) 0.004(5) -0.008(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O9 1.902(9) . ? Cu1 O11 1.987(9) . ? Cu1 O1 2.018(8) . ? Cu1 N1 2.053(10) 2_656 ? Cu1 O13 2.367(8) 2_655 ? Cu2 O10 1.908(9) 2_655 ? Cu2 O5 1.954(10) . ? Cu2 O1 1.959(8) . ? Cu2 O13 1.982(9) 2_655 ? Cu2 O19 2.460(11) . ? Cu3 O8 1.908(8) 1_565 ? Cu3 O2 1.924(8) . ? Cu3 O4 2.000(9) . ? Cu3 N2 2.036(11) 2_656 ? Cu3 O19 2.477(14) . ? Cu4 O12 1.901(9) . ? Cu4 O6 1.935(9) 2_755 ? Cu4 O16 1.98(2) . ? Cu4 O15 1.995(16) . ? Cu4 O17 2.30(2) . ? P1 O2 1.494(8) . ? P1 O3 1.521(8) . ? P1 O1 1.543(8) . ? P1 C1 1.828(13) . ? P2 O6 1.510(10) . ? P2 O4 1.525(9) . ? P2 O5 1.527(10) . ? P2 C1 1.861(12) . ? P3 O8 1.506(8) . ? P3 O10 1.529(9) . ? P3 O9 1.529(9) . ? P3 C8 1.848(13) . ? P4 O12 1.514(10) . ? P4 O13 1.526(9) . ? P4 O11 1.527(9) . ? P4 C8 1.855(11) . ? O6 Cu4 1.935(9) 2_755 ? O7 C1 1.445(14) . ? O8 Cu3 1.908(8) 1_545 ? O10 Cu2 1.908(9) 2_655 ? O13 Cu2 1.982(9) 2_655 ? O13 Cu1 2.367(8) 2_655 ? O14 C8 1.452(14) . ? N1 C5 1.333(16) . ? N1 C4 1.345(15) . ? N1 Cu1 2.053(10) 2_656 ? N2 C14 1.333(15) . ? N2 C13 1.355(17) . ? N2 Cu3 2.036(11) 2_656 ? C1 C2 1.559(16) . ? C2 C3 1.520(18) . ? C3 C7 1.377(18) . ? C3 C4 1.379(19) . ? C5 C6 1.35(2) . ? C6 C7 1.41(2) . ? C8 C9 1.551(16) . ? C9 C10 1.509(16) . ? C10 C11 1.380(18) . ? C10 C14 1.394(18) . ? C11 C12 1.381(19) . ? C12 C13 1.38(2) . ? 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 O9 Cu1 O11 95.0(4) . . ? O9 Cu1 O1 162.4(4) . . ? O11 Cu1 O1 83.3(3) . . ? O9 Cu1 N1 90.9(4) . 2_656 ? O11 Cu1 N1 170.4(4) . 2_656 ? O1 Cu1 N1 88.7(4) . 2_656 ? O9 Cu1 O13 126.1(4) . 2_655 ? O11 Cu1 O13 87.2(3) . 2_655 ? O1 Cu1 O13 71.5(3) . 2_655 ? N1 Cu1 O13 95.4(4) 2_656 2_655 ? O10 Cu2 O5 90.1(4) 2_655 . ? O10 Cu2 O1 176.4(4) 2_655 . ? O5 Cu2 O1 93.4(4) . . ? O10 Cu2 O13 95.0(4) 2_655 2_655 ? O5 Cu2 O13 161.6(4) . 2_655 ? O1 Cu2 O13 81.7(3) . 2_655 ? O10 Cu2 O19 94.3(4) 2_655 . ? O5 Cu2 O19 94.0(4) . . ? O1 Cu2 O19 85.4(4) . . ? O13 Cu2 O19 103.1(4) 2_655 . ? O8 Cu3 O2 168.3(4) 1_565 . ? O8 Cu3 O4 91.2(4) 1_565 . ? O2 Cu3 O4 91.5(3) . . ? O8 Cu3 N2 88.3(4) 1_565 2_656 ? O2 Cu3 N2 87.3(4) . 2_656 ? O4 Cu3 N2 170.8(4) . 2_656 ? O8 Cu3 O19 92.9(3) 1_565 . ? O2 Cu3 O19 98.6(4) . . ? O4 Cu3 O19 87.5(4) . . ? N2 Cu3 O19 101.7(4) 2_656 . ? O12 Cu4 O6 175.6(4) . 2_755 ? O12 Cu4 O16 85.8(7) . . ? O6 Cu4 O16 93.2(6) 2_755 . ? O12 Cu4 O15 92.9(6) . . ? O6 Cu4 O15 86.9(5) 2_755 . ? O16 Cu4 O15 163.9(9) . . ? O12 Cu4 O17 92.9(7) . . ? O6 Cu4 O17 91.5(7) 2_755 . ? O16 Cu4 O17 100.6(9) . . ? O15 Cu4 O17 95.5(8) . . ? O2 P1 O3 114.5(5) . . ? O2 P1 O1 112.9(5) . . ? O3 P1 O1 107.3(5) . . ? O2 P1 C1 106.4(5) . . ? O3 P1 C1 109.9(5) . . ? O1 P1 C1 105.5(5) . . ? O6 P2 O4 110.3(5) . . ? O6 P2 O5 111.8(5) . . ? O4 P2 O5 114.1(6) . . ? O6 P2 C1 107.4(5) . . ? O4 P2 C1 107.0(5) . . ? O5 P2 C1 105.8(5) . . ? O8 P3 O10 110.9(5) . . ? O8 P3 O9 111.0(5) . . ? O10 P3 O9 111.8(6) . . ? O8 P3 C8 109.1(5) . . ? O10 P3 C8 105.7(6) . . ? O9 P3 C8 108.1(5) . . ? O12 P4 O13 111.9(5) . . ? O12 P4 O11 109.9(5) . . ? O13 P4 O11 113.6(5) . . ? O12 P4 C8 107.8(6) . . ? O13 P4 C8 108.2(5) . . ? O11 P4 C8 105.1(5) . . ? P1 O1 Cu2 136.3(5) . . ? P1 O1 Cu1 116.1(4) . . ? Cu2 O1 Cu1 102.6(3) . . ? P1 O2 Cu3 129.0(5) . . ? P2 O4 Cu3 132.5(5) . . ? P2 O5 Cu2 128.7(6) . . ? P2 O6 Cu4 135.3(6) . 2_755 ? P3 O8 Cu3 137.5(6) . 1_545 ? P3 O9 Cu1 137.4(6) . . ? P3 O10 Cu2 128.0(6) . 2_655 ? P4 O11 Cu1 129.5(5) . . ? P4 O12 Cu4 141.7(6) . . ? P4 O13 Cu2 135.2(5) . 2_655 ? P4 O13 Cu1 122.9(5) . 2_655 ? Cu2 O13 Cu1 90.7(3) 2_655 2_655 ? Cu2 O19 Cu3 109.3(5) . . ? C5 N1 C4 117.0(11) . . ? C5 N1 Cu1 119.6(8) . 2_656 ? C4 N1 Cu1 121.2(8) . 2_656 ? C14 N2 C13 118.0(12) . . ? C14 N2 Cu3 118.1(9) . 2_656 ? C13 N2 Cu3 123.8(9) . 2_656 ? O7 C1 C2 109.0(10) . . ? O7 C1 P1 109.9(8) . . ? C2 C1 P1 111.7(8) . . ? O7 C1 P2 109.6(8) . . ? C2 C1 P2 108.9(8) . . ? P1 C1 P2 107.8(6) . . ? C3 C2 C1 116.1(10) . . ? C7 C3 C4 117.6(12) . . ? C7 C3 C2 121.5(12) . . ? C4 C3 C2 120.9(12) . . ? N1 C4 C3 124.3(12) . . ? N1 C5 C6 123.4(12) . . ? C5 C6 C7 119.4(13) . . ? C3 C7 C6 118.4(13) . . ? O14 C8 C9 109.5(10) . . ? O14 C8 P3 108.3(8) . . ? C9 C8 P3 117.3(8) . . ? O14 C8 P4 107.3(8) . . ? C9 C8 P4 106.7(7) . . ? P3 C8 P4 107.2(6) . . ? C10 C9 C8 114.7(10) . . ? C11 C10 C14 117.7(12) . . ? C11 C10 C9 123.8(12) . . ? C14 C10 C9 118.4(11) . . ? C10 C11 C12 118.6(13) . . ? C13 C12 C11 120.8(13) . . ? N2 C13 C12 120.9(12) . . ? N2 C14 C10 123.8(12) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 2.448 _refine_diff_density_min -3.191 _refine_diff_density_rms 0.321