# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_trial2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H20 Cl N8 P' _chemical_formula_sum 'C20 H20 Cl N8 P' _chemical_formula_weight 438.86 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Cubic _symmetry_space_group_name_H-M I-43d loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/4, z+1/4, -y+3/4' '-x+1/4, -z+3/4, y+3/4' '-z+1/4, -y+3/4, x+3/4' 'z+1/4, -y+3/4, -x+1/4' 'y+1/4, -x+3/4, -z+1/4' '-y+1/4, x+1/4, -z+3/4' 'z, x, y' 'y, z, x' '-y, -z+1/2, x' 'z, -x, -y+1/2' '-y+1/2, z, -x' '-z, -x+1/2, y' '-z+1/2, x, -y' 'y, -z, -x+1/2' 'x, -y, -z+1/2' '-x+1/2, y, -z' '-x, -y+1/2, z' '-y+1/4, -x+3/4, z+3/4' 'y+1/4, x+1/4, z+1/4' '-z+1/4, y+1/4, -x+3/4' 'z+1/4, y+1/4, x+1/4' 'x+1/4, -z+3/4, -y+1/4' 'x+1/4, z+1/4, y+1/4' 'x+1/2, y+1/2, z+1/2' '-x+3/4, z+3/4, -y+5/4' '-x+3/4, -z+5/4, y+5/4' '-z+3/4, -y+5/4, x+5/4' 'z+3/4, -y+5/4, -x+3/4' 'y+3/4, -x+5/4, -z+3/4' '-y+3/4, x+3/4, -z+5/4' 'z+1/2, x+1/2, y+1/2' 'y+1/2, z+1/2, x+1/2' '-y+1/2, -z+1, x+1/2' 'z+1/2, -x+1/2, -y+1' '-y+1, z+1/2, -x+1/2' '-z+1/2, -x+1, y+1/2' '-z+1, x+1/2, -y+1/2' 'y+1/2, -z+1/2, -x+1' 'x+1/2, -y+1/2, -z+1' '-x+1, y+1/2, -z+1/2' '-x+1/2, -y+1, z+1/2' '-y+3/4, -x+5/4, z+5/4' 'y+3/4, x+3/4, z+3/4' '-z+3/4, y+3/4, -x+5/4' 'z+3/4, y+3/4, x+3/4' 'x+3/4, -z+5/4, -y+3/4' 'x+3/4, z+3/4, y+3/4' _cell_length_a 18.926(5) _cell_length_b 18.926(5) _cell_length_c 18.926(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 6779(3) _cell_formula_units_Z 12 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9962 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 26.79 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2736 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7046 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and oemga scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 53850 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0103 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.31 _diffrn_reflns_theta_max 28.22 _reflns_number_total 1398 _reflns_number_gt 1306 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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' _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^)+(0.1791P)^2^+2.3296P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(2) _refine_ls_number_reflns 1398 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0743 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.2389 _refine_ls_wR_factor_gt 0.2315 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.190 _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 P1 P 1.0000 0.7500 0.1250 0.0335(4) Uani 1 4 d S . . Cl1 Cl 1.0293(2) 0.44814(19) 0.4280(2) 0.0503(9) Uani 0.25 1 d P . . N1 N 0.94820(13) 0.69934(13) 0.17162(13) 0.0312(6) Uani 1 1 d . . . H1 H 0.9026 0.7031 0.1633 0.037 Uiso 1 1 calc R . . N24 N 1.00301(18) 0.54961(14) 0.32576(16) 0.0425(7) Uani 1 1 d . . . C21 C 0.96815(16) 0.65111(15) 0.22281(15) 0.0311(6) Uani 1 1 d . . . C22 C 0.91646(17) 0.61058(15) 0.25573(17) 0.0370(7) Uani 1 1 d . . . H22 H 0.8680 0.6172 0.2443 0.044 Uiso 1 1 calc R . . C23 C 0.9362(2) 0.56026(18) 0.30554(17) 0.0416(8) Uani 1 1 d . . . H23 H 0.9003 0.5320 0.3263 0.050 Uiso 1 1 calc R . . C25 C 1.05196(18) 0.58974(18) 0.29551(17) 0.0396(7) Uani 1 1 d . . . H25 H 1.0995 0.5835 0.3102 0.048 Uiso 1 1 calc R . . C26 C 1.03873(16) 0.64005(17) 0.24413(18) 0.0369(7) Uani 1 1 d . . . H26 H 1.0762 0.6665 0.2237 0.044 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0306(5) 0.0306(5) 0.0393(8) 0.000 0.000 0.000 Cl1 0.0580(19) 0.0303(13) 0.063(2) 0.0119(13) -0.0166(15) 0.0053(13) N1 0.0276(11) 0.0314(11) 0.0346(12) 0.0051(9) 0.0003(9) -0.0003(9) N24 0.0533(16) 0.0334(12) 0.0407(14) 0.0018(10) 0.0033(12) 0.0101(11) C21 0.0350(14) 0.0301(12) 0.0283(12) -0.0033(10) -0.0010(11) 0.0031(11) C22 0.0377(14) 0.0378(15) 0.0355(14) 0.0005(12) 0.0042(12) 0.0019(12) C23 0.0535(18) 0.0344(14) 0.0369(16) 0.0039(12) 0.0121(14) 0.0064(13) C25 0.0382(15) 0.0402(16) 0.0404(15) -0.0001(13) -0.0030(12) 0.0096(12) C26 0.0315(14) 0.0366(15) 0.0426(16) 0.0004(12) -0.0002(12) 0.0026(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 P1 N1 1.631(3) 18_765 ? P1 N1 1.631(3) 31_644 ? P1 N1 1.631(3) 6_565 ? P1 N1 1.631(3) . ? N1 C21 1.384(4) . ? N1 H1 0.8800 . ? N24 C25 1.328(4) . ? N24 C23 1.336(5) . ? C21 C22 1.391(4) . ? C21 C26 1.411(4) . ? C22 C23 1.391(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C25 C26 1.384(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 N1 107.02(8) 18_765 31_644 ? N1 P1 N1 107.02(8) 18_765 6_565 ? N1 P1 N1 114.49(16) 31_644 6_565 ? N1 P1 N1 114.49(16) 18_765 . ? N1 P1 N1 107.02(8) 31_644 . ? N1 P1 N1 107.02(8) 6_565 . ? C21 N1 P1 127.1(2) . . ? C21 N1 H1 116.5 . . ? P1 N1 H1 116.5 . . ? C25 N24 C23 116.8(3) . . ? N1 C21 C22 119.1(3) . . ? N1 C21 C26 123.8(3) . . ? C22 C21 C26 117.1(3) . . ? C21 C22 C23 119.5(3) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? N24 C23 C22 123.5(4) . . ? N24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? N24 C25 C26 124.8(3) . . ? N24 C25 H25 117.6 . . ? C26 C25 H25 117.6 . . ? C25 C26 C21 118.3(3) . . ? C25 C26 H26 120.8 . . ? C21 C26 H26 120.8 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 Cl1 0.88 1.96 2.801(4) 160.8 19_664 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.064 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 906702' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ag027c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H21 N6 O3 P' _chemical_formula_weight 376.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.9218(6) _cell_length_b 9.3485(5) _cell_length_c 9.7630(5) _cell_angle_alpha 90.00 _cell_angle_beta 110.049(3) _cell_angle_gamma 90.00 _cell_volume 936.42(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6576 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 28.33 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6221 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex II' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9844 _diffrn_reflns_av_R_equivalents 0.0742 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 28.38 _reflns_number_total 4083 _reflns_number_gt 3813 _reflns_threshold_expression >2sigma(I) _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' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogens of the solvated water were first located and then refined by using a riding model. The non-bonding distance between these two hydrogens were fixed by using the DANG command to impose the angle restraint in the water molecule. ; _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^)+(0.0870P)^2^+0.0973P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(10) _refine_ls_number_reflns 4083 _refine_ls_number_parameters 243 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1361 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.069 _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 P1 P 0.38467(5) 0.60150(5) 0.51467(5) 0.02935(14) Uani 1 1 d . . . O1 O 0.3605(2) 0.52167(18) 0.63357(19) 0.0390(4) Uani 1 1 d . . . N1 N 0.4803(2) 0.5133(2) 0.4433(2) 0.0353(4) Uani 1 1 d . . . H1 H 0.4687 0.5284 0.3528 0.042 Uiso 1 1 calc R . . N2 N 0.45609(19) 0.7580(2) 0.5633(2) 0.0334(4) Uani 1 1 d . . . H2 H 0.5306 0.7709 0.5534 0.040 Uiso 1 1 calc R . . N3 N 0.2548(2) 0.6433(2) 0.3758(2) 0.0328(4) Uani 1 1 d . . . H3 H 0.2502 0.7304 0.3462 0.039 Uiso 1 1 calc R . . N11 N 0.7661(3) 0.2127(3) 0.6573(3) 0.0613(7) Uani 1 1 d . . . N21 N 0.3052(3) 1.1051(3) 0.7302(4) 0.0583(7) Uani 1 1 d . . . N31 N -0.0623(3) 0.3873(3) 0.1361(4) 0.0628(8) Uani 1 1 d . . . C11 C 0.5775(2) 0.4168(3) 0.5174(3) 0.0340(5) Uani 1 1 d . . . C12 C 0.6083(3) 0.3051(3) 0.4399(3) 0.0428(6) Uani 1 1 d . . . H12 H 0.5654 0.2962 0.3399 0.051 Uiso 1 1 calc R . . C13 C 0.7033(3) 0.2080(3) 0.5139(4) 0.0552(7) Uani 1 1 d . . . H13 H 0.7246 0.1355 0.4607 0.066 Uiso 1 1 calc R . . C14 C 0.7361(3) 0.3213(4) 0.7281(4) 0.0592(8) Uani 1 1 d . . . H14 H 0.7794 0.3267 0.8282 0.071 Uiso 1 1 calc R . . C15 C 0.6469(3) 0.4253(4) 0.6656(3) 0.0493(7) Uani 1 1 d . . . H15 H 0.6330 0.5003 0.7211 0.059 Uiso 1 1 calc R . . C21 C 0.4042(3) 0.8709(3) 0.6193(3) 0.0363(5) Uani 1 1 d . . . C22 C 0.4579(4) 1.0073(3) 0.6284(5) 0.0586(8) Uani 1 1 d . . . H22 H 0.5285 1.0233 0.5976 0.070 Uiso 1 1 calc R . . C23 C 0.4058(4) 1.1177(3) 0.6830(5) 0.0675(10) Uani 1 1 d . . . H23 H 0.4432 1.2077 0.6875 0.081 Uiso 1 1 calc R . . C24 C 0.2572(4) 0.9745(4) 0.7236(4) 0.0565(8) Uani 1 1 d . . . H24 H 0.1880 0.9615 0.7572 0.068 Uiso 1 1 calc R . . C25 C 0.3019(3) 0.8554(3) 0.6703(4) 0.0496(7) Uani 1 1 d . . . H25 H 0.2634 0.7664 0.6691 0.059 Uiso 1 1 calc R . . C31 C 0.1504(2) 0.5548(3) 0.2993(3) 0.0345(5) Uani 1 1 d . . . C32 C 0.0575(3) 0.6069(3) 0.1724(4) 0.0537(8) Uani 1 1 d . . . H32 H 0.0639 0.6990 0.1396 0.064 Uiso 1 1 calc R . . C33 C -0.0441(4) 0.5187(4) 0.0967(5) 0.0670(10) Uani 1 1 d . . . H33 H -0.1045 0.5543 0.0112 0.080 Uiso 1 1 calc R . . C34 C 0.0270(3) 0.3399(4) 0.2587(5) 0.0611(9) Uani 1 1 d . . . H34 H 0.0158 0.2485 0.2900 0.073 Uiso 1 1 calc R . . C35 C 0.1358(3) 0.4171(4) 0.3434(4) 0.0502(7) Uani 1 1 d . . . H35 H 0.1965 0.3775 0.4264 0.060 Uiso 1 1 calc R . . O1S O 0.7219(3) 0.1952(3) 0.0924(5) 0.0832(10) Uani 1 1 d D . . H1S H 0.728(6) 0.129(5) 0.147(6) 0.100 Uiso 1 1 d D . . H2S H 0.791(4) 0.194(6) 0.078(7) 0.100 Uiso 1 1 d D . . O2M O 0.9109(7) -0.0113(4) 0.7985(6) 0.149(2) Uani 1 1 d . . . H2M H 0.8823 0.0624 0.7533 0.179 Uiso 1 1 calc R . . C2S C 0.9803(7) 0.0202(7) 0.9312(7) 0.1070(19) Uani 1 1 d . . . H2S1 H 1.0550 0.0748 0.9319 0.160 Uiso 1 1 calc R . . H2S2 H 1.0085 -0.0663 0.9860 0.160 Uiso 1 1 calc R . . H2S3 H 0.9289 0.0755 0.9743 0.160 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0341(3) 0.0322(2) 0.0212(2) 0.0001(2) 0.0089(2) -0.0006(2) O1 0.0499(10) 0.0427(9) 0.0252(8) 0.0026(7) 0.0137(8) -0.0037(8) N1 0.0438(11) 0.0397(10) 0.0227(9) 0.0001(8) 0.0117(8) 0.0069(8) N2 0.0324(9) 0.0363(9) 0.0317(10) -0.0041(8) 0.0111(8) -0.0038(7) N3 0.0337(9) 0.0339(9) 0.0278(10) 0.0030(8) 0.0066(8) -0.0014(7) N11 0.0591(15) 0.0595(15) 0.0533(16) 0.0127(13) 0.0037(13) 0.0174(13) N21 0.0666(18) 0.0518(15) 0.0563(17) -0.0151(12) 0.0206(15) 0.0051(12) N31 0.0415(13) 0.0685(19) 0.070(2) -0.0168(15) 0.0080(14) -0.0110(11) C11 0.0349(11) 0.0368(11) 0.0293(12) 0.0034(9) 0.0098(10) 0.0018(8) C12 0.0524(15) 0.0393(13) 0.0334(13) -0.0019(10) 0.0105(12) 0.0033(11) C13 0.0655(18) 0.0441(14) 0.0513(18) -0.0002(13) 0.0139(15) 0.0147(13) C14 0.0536(17) 0.077(2) 0.0363(16) 0.0065(15) 0.0013(14) 0.0114(16) C15 0.0501(16) 0.0606(17) 0.0347(15) -0.0086(13) 0.0115(13) 0.0080(13) C21 0.0383(12) 0.0373(12) 0.0294(12) -0.0028(9) 0.0067(10) 0.0008(9) C22 0.0694(19) 0.0435(15) 0.074(2) -0.0130(14) 0.0385(18) -0.0151(14) C23 0.077(2) 0.0392(15) 0.094(3) -0.0168(16) 0.039(2) -0.0120(14) C24 0.0537(16) 0.0591(18) 0.063(2) -0.0184(15) 0.0280(16) 0.0000(13) C25 0.0527(15) 0.0423(13) 0.0604(19) -0.0113(13) 0.0279(15) -0.0046(11) C31 0.0320(11) 0.0410(12) 0.0315(12) -0.0033(9) 0.0121(10) 0.0000(9) C32 0.0436(15) 0.0549(17) 0.0512(19) 0.0071(13) 0.0016(14) -0.0043(12) C33 0.0459(16) 0.072(2) 0.063(2) 0.0007(17) -0.0072(16) -0.0060(15) C34 0.0561(18) 0.0465(16) 0.076(3) -0.0068(17) 0.0160(17) -0.0149(14) C35 0.0455(15) 0.0490(16) 0.0475(18) -0.0007(13) 0.0049(14) -0.0084(11) O1S 0.0418(11) 0.0784(18) 0.126(3) 0.0179(17) 0.0240(15) -0.0035(12) O2M 0.210(6) 0.075(2) 0.099(3) -0.011(2) -0.028(3) 0.062(3) C2S 0.111(4) 0.111(4) 0.079(4) 0.000(3) 0.007(3) 0.034(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4781(17) . ? P1 N3 1.638(2) . ? P1 N2 1.649(2) . ? P1 N1 1.660(2) . ? N1 C11 1.392(3) . ? N2 C21 1.395(3) . ? N3 C31 1.399(3) . ? N11 C14 1.331(5) . ? N11 C13 1.332(5) . ? N21 C24 1.321(5) . ? N21 C23 1.335(5) . ? N31 C33 1.323(5) . ? N31 C34 1.334(5) . ? C11 C15 1.386(4) . ? C11 C12 1.397(3) . ? C12 C13 1.382(4) . ? C14 C15 1.363(5) . ? C21 C25 1.379(4) . ? C21 C22 1.394(4) . ? C22 C23 1.372(5) . ? C24 C25 1.386(4) . ? C31 C35 1.384(4) . ? C31 C32 1.392(4) . ? C32 C33 1.376(5) . ? C34 C35 1.394(4) . ? O2M C2S 1.291(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 O1 P1 N3 115.66(11) . . ? O1 P1 N2 114.60(11) . . ? N3 P1 N2 102.51(10) . . ? O1 P1 N1 112.73(10) . . ? N3 P1 N1 105.17(11) . . ? N2 P1 N1 104.95(11) . . ? C11 N1 P1 125.53(17) . . ? C21 N2 P1 124.62(16) . . ? C31 N3 P1 128.09(17) . . ? C14 N11 C13 116.2(3) . . ? C24 N21 C23 115.1(3) . . ? C33 N31 C34 115.7(3) . . ? C15 C11 N1 123.5(2) . . ? C15 C11 C12 117.5(2) . . ? N1 C11 C12 119.0(2) . . ? C13 C12 C11 119.0(3) . . ? N11 C13 C12 123.5(3) . . ? N11 C14 C15 125.3(3) . . ? C14 C15 C11 118.5(3) . . ? C25 C21 C22 116.7(3) . . ? C25 C21 N2 123.4(2) . . ? C22 C21 N2 119.9(2) . . ? C23 C22 C21 119.4(3) . . ? N21 C23 C22 124.6(3) . . ? N21 C24 C25 125.2(3) . . ? C21 C25 C24 118.9(3) . . ? C35 C31 C32 118.4(3) . . ? C35 C31 N3 122.9(2) . . ? C32 C31 N3 118.7(2) . . ? C33 C32 C31 118.4(3) . . ? N31 C33 C32 125.0(4) . . ? N31 C34 C35 124.9(3) . . ? C31 C35 C34 117.5(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.86 2.11 2.872(3) 146.9 2_564 N2 H2 O1S 0.86 2.02 2.852(3) 163.7 2_565 N3 H3 N21 0.86 2.12 2.897(3) 150.9 2_574 O1S H1S O2M 0.80(3) 2.32(6) 2.902(6) 130(5) 2_554 O1S H2S N31 0.81(3) 2.36(5) 2.877(4) 123(5) 1_655 O2M H2M N11 0.82 1.91 2.700(5) 161.5 . _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.438 _refine_diff_density_min -0.448 _refine_diff_density_rms 0.062 _database_code_depnum_ccdc_archive 'CCDC 906703' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_trial1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 N5 O6 P Zn' _chemical_formula_weight 450.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.073(2) _cell_length_b 15.623(3) _cell_length_c 18.459(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4058.3(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1111 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 16.50 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 1.328 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6001 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 47637 _diffrn_reflns_av_R_equivalents 0.1863 _diffrn_reflns_av_sigmaI/netI 0.0839 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3576 _reflns_number_gt 2180 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogens of the solvated water were first located and then refined by using a riding model. The non-bonding distance between these two water hydrogens were fixed by using the DANG command to impose the angle restraint in the water molecule. Crystals diffracted weakly beyond 2theta = 50 degree and hence a cutoff was applied. ; _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^)+(0.0449P)^2^+7.4809P] 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 SHELXL _refine_ls_extinction_coef 0.0009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3576 _refine_ls_number_parameters 253 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1046 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1302 _refine_ls_wR_factor_gt 0.1044 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.16580(4) 1.04053(4) 0.35947(3) 0.0258(2) Uani 1 1 d . . . P1 P 0.34223(9) 0.99500(8) 0.46331(7) 0.0235(3) Uani 1 1 d . . . O1 O 0.4052(2) 1.0687(2) 0.47885(19) 0.0304(9) Uani 1 1 d . . . O2 O 0.2842(2) 0.9950(2) 0.39494(17) 0.0279(8) Uani 1 1 d . . . N1 N 0.4127(3) 0.9094(3) 0.4621(2) 0.0275(10) Uani 1 1 d . . . H1 H 0.4718 0.9183 0.4756 0.033 Uiso 1 1 calc R . . N2 N 0.2631(3) 0.9799(3) 0.5295(2) 0.0299(11) Uani 1 1 d . . . H2 H 0.2032 0.9761 0.5161 0.036 Uiso 1 1 calc R . . C11 C 0.3906(4) 0.8261(3) 0.4426(3) 0.0253(12) Uani 1 1 d . . . C12 C 0.4615(4) 0.7630(3) 0.4466(3) 0.0323(13) Uani 1 1 d . . . H12 H 0.5228 0.7769 0.4646 0.039 Uiso 1 1 calc R . . C13 C 0.4415(4) 0.6815(3) 0.4243(3) 0.0331(13) Uani 1 1 d . . . H13 H 0.4908 0.6400 0.4260 0.040 Uiso 1 1 calc R . . N14 N 0.3553(3) 0.6572(3) 0.4002(2) 0.0285(10) Uani 1 1 d . . . C15 C 0.2866(4) 0.7177(3) 0.3992(3) 0.0350(14) Uani 1 1 d . . . H15 H 0.2250 0.7013 0.3833 0.042 Uiso 1 1 calc R . . C16 C 0.3000(4) 0.8006(3) 0.4196(3) 0.0337(13) Uani 1 1 d . . . H16 H 0.2490 0.8404 0.4182 0.040 Uiso 1 1 calc R . . C21 C 0.2807(4) 0.9728(3) 0.6024(3) 0.0280(12) Uani 1 1 d . . . C22 C 0.2053(4) 0.9622(4) 0.6508(3) 0.0337(13) Uani 1 1 d . . . H22 H 0.1421 0.9592 0.6329 0.040 Uiso 1 1 calc R . . C23 C 0.2216(4) 0.9560(4) 0.7234(3) 0.0354(13) Uani 1 1 d . . . H23 H 0.1689 0.9492 0.7550 0.043 Uiso 1 1 calc R . . N24 N 0.3102(3) 0.9591(3) 0.7523(2) 0.0292(10) Uani 1 1 d . . . C25 C 0.3826(4) 0.9683(4) 0.7053(3) 0.0338(13) Uani 1 1 d . . . H25 H 0.4454 0.9699 0.7241 0.041 Uiso 1 1 calc R . . C26 C 0.3711(4) 0.9757(3) 0.6326(3) 0.0336(13) Uani 1 1 d . . . H26 H 0.4250 0.9828 0.6022 0.040 Uiso 1 1 calc R . . O1S O 0.4139(6) 0.7357(5) 0.6647(5) 0.147(3) Uani 1 1 d . . . C1S C 0.3402(9) 0.7213(7) 0.6988(7) 0.125(4) Uani 1 1 d . . . H1S H 0.3453 0.7137 0.7497 0.149 Uiso 1 1 calc R . . N4 N 0.2565(6) 0.7157(4) 0.6704(4) 0.085(2) Uani 1 1 d . . . C2S C 0.2431(9) 0.7252(6) 0.5934(5) 0.131(4) Uani 1 1 d . . . H2S1 H 0.3052 0.7283 0.5695 0.197 Uiso 1 1 calc R . . H2S2 H 0.2075 0.7779 0.5837 0.197 Uiso 1 1 calc R . . H2S3 H 0.2077 0.6760 0.5746 0.197 Uiso 1 1 calc R . . C3S C 0.1711(8) 0.7045(7) 0.7140(6) 0.138(5) Uani 1 1 d . . . H3S1 H 0.1891 0.6914 0.7641 0.207 Uiso 1 1 calc R . . H3S2 H 0.1332 0.6573 0.6943 0.207 Uiso 1 1 calc R . . H3S3 H 0.1336 0.7573 0.7130 0.207 Uiso 1 1 calc R . . O3 O 0.0473(3) 0.9770(3) 0.3671(2) 0.0448(10) Uani 1 1 d . . . C1 C 0.0352(4) 0.9321(4) 0.4229(3) 0.0442(16) Uani 1 1 d . . . H1A H -0.0211 0.8986 0.4244 0.053 Uiso 1 1 calc R . . O4 O 0.0873(3) 0.9267(3) 0.4751(2) 0.0544(12) Uani 1 1 d . . . O1W O 0.5724(4) 0.8410(4) 0.6600(3) 0.0766(16) Uani 1 1 d D . . H1W H 0.572(6) 0.857(5) 0.6151(18) 0.115 Uiso 1 1 d D . . H2W H 0.531(5) 0.799(4) 0.659(4) 0.115 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0279(4) 0.0295(3) 0.0199(3) -0.0008(3) -0.0016(3) 0.0017(3) P1 0.0229(7) 0.0267(7) 0.0209(7) -0.0004(5) -0.0025(6) -0.0004(6) O1 0.025(2) 0.030(2) 0.036(2) -0.0010(16) -0.0025(16) -0.0050(16) O2 0.026(2) 0.036(2) 0.0221(18) 0.0012(16) -0.0028(15) 0.0023(17) N1 0.022(2) 0.026(2) 0.034(3) 0.000(2) -0.008(2) 0.001(2) N2 0.020(2) 0.045(3) 0.025(2) 0.000(2) -0.0029(18) -0.003(2) C11 0.022(3) 0.028(3) 0.026(3) 0.007(2) 0.002(2) -0.004(2) C12 0.020(3) 0.032(3) 0.045(4) -0.004(3) -0.010(2) -0.001(2) C13 0.029(3) 0.035(3) 0.036(3) -0.006(3) -0.006(3) 0.002(3) N14 0.029(3) 0.032(2) 0.025(2) -0.0016(19) -0.0048(19) -0.003(2) C15 0.026(3) 0.035(3) 0.043(3) -0.003(3) -0.010(3) -0.004(3) C16 0.025(3) 0.028(3) 0.048(4) -0.002(3) -0.003(3) 0.001(2) C21 0.029(3) 0.037(3) 0.018(3) -0.002(2) 0.002(2) 0.002(2) C22 0.020(3) 0.055(4) 0.026(3) -0.002(3) -0.004(2) 0.002(3) C23 0.024(3) 0.053(4) 0.029(3) 0.006(3) 0.007(2) 0.001(3) N24 0.025(3) 0.041(3) 0.021(2) 0.000(2) 0.0019(18) 0.000(2) C25 0.021(3) 0.054(4) 0.027(3) -0.001(3) 0.002(2) -0.002(3) C26 0.027(3) 0.053(4) 0.020(3) 0.003(3) 0.000(2) -0.002(3) O1S 0.101(6) 0.123(6) 0.215(9) -0.039(6) 0.063(6) -0.024(5) C1S 0.088(9) 0.131(10) 0.154(11) -0.057(8) 0.003(8) -0.024(8) N4 0.107(6) 0.065(4) 0.084(5) -0.016(4) 0.023(5) -0.018(4) C2S 0.196(13) 0.125(9) 0.074(7) 0.010(6) 0.025(8) -0.005(8) C3S 0.154(11) 0.131(9) 0.128(9) -0.053(7) 0.081(8) -0.058(8) O3 0.037(2) 0.060(3) 0.037(2) 0.007(2) -0.0022(18) -0.012(2) C1 0.037(4) 0.059(4) 0.037(4) 0.003(3) 0.000(3) -0.014(3) O4 0.033(2) 0.088(3) 0.043(3) 0.015(2) -0.007(2) -0.019(2) O1W 0.047(3) 0.109(5) 0.075(4) 0.021(3) 0.004(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 1.927(3) . ? Zn1 O3 1.945(4) . ? Zn1 N14 1.993(4) 6_665 ? Zn1 N24 2.007(4) 4_574 ? P1 O1 1.481(4) . ? P1 O2 1.503(3) . ? P1 N1 1.665(4) . ? P1 N2 1.670(4) . ? N1 C11 1.386(6) . ? N1 H1 0.8800 . ? N2 C21 1.373(6) . ? N2 H2 0.8800 . ? C11 C16 1.401(7) . ? C11 C12 1.404(7) . ? C12 C13 1.368(7) . ? C12 H12 0.9500 . ? C13 N14 1.347(6) . ? C13 H13 0.9500 . ? N14 C15 1.353(7) . ? N14 Zn1 1.993(4) 6_655 ? C15 C16 1.362(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.389(7) . ? C21 C22 1.397(7) . ? C22 C23 1.363(7) . ? C22 H22 0.9500 . ? C23 N24 1.358(6) . ? C23 H23 0.9500 . ? N24 C25 1.345(6) . ? N24 Zn1 2.007(4) 4_575 ? C25 C26 1.357(7) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O1S C1S 1.233(12) . ? C1S N4 1.292(12) . ? C1S H1S 0.9500 . ? N4 C2S 1.441(11) . ? N4 C3S 1.457(11) . ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? C3S H3S1 0.9800 . ? C3S H3S2 0.9800 . ? C3S H3S3 0.9800 . ? O3 C1 1.258(7) . ? C1 O4 1.213(7) . ? C1 H1A 0.9500 . ? O1W H1W 0.87(2) . ? O1W H2W 0.88(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 O2 Zn1 O3 121.88(16) . . ? O2 Zn1 N14 109.80(16) . 6_665 ? O3 Zn1 N14 108.15(18) . 6_665 ? O2 Zn1 N24 101.00(15) . 4_574 ? O3 Zn1 N24 102.52(17) . 4_574 ? N14 Zn1 N24 113.17(17) 6_665 4_574 ? O1 P1 O2 119.2(2) . . ? O1 P1 N1 105.7(2) . . ? O2 P1 N1 108.1(2) . . ? O1 P1 N2 111.5(2) . . ? O2 P1 N2 104.6(2) . . ? N1 P1 N2 107.1(2) . . ? P1 O2 Zn1 139.0(2) . . ? C11 N1 P1 128.6(4) . . ? C11 N1 H1 115.7 . . ? P1 N1 H1 115.7 . . ? C21 N2 P1 127.4(4) . . ? C21 N2 H2 116.3 . . ? P1 N2 H2 116.3 . . ? N1 C11 C16 123.3(5) . . ? N1 C11 C12 119.1(4) . . ? C16 C11 C12 117.6(5) . . ? C13 C12 C11 119.4(5) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? N14 C13 C12 123.2(5) . . ? N14 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C13 N14 C15 116.8(4) . . ? C13 N14 Zn1 121.1(4) . 6_655 ? C15 N14 Zn1 121.8(3) . 6_655 ? N14 C15 C16 124.2(5) . . ? N14 C15 H15 117.9 . . ? C16 C15 H15 117.9 . . ? C15 C16 C11 118.7(5) . . ? C15 C16 H16 120.7 . . ? C11 C16 H16 120.7 . . ? N2 C21 C26 123.8(4) . . ? N2 C21 C22 119.9(5) . . ? C26 C21 C22 116.3(4) . . ? C23 C22 C21 120.6(5) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? N24 C23 C22 122.6(5) . . ? N24 C23 H23 118.7 . . ? C22 C23 H23 118.7 . . ? C25 N24 C23 116.5(4) . . ? C25 N24 Zn1 120.5(3) . 4_575 ? C23 N24 Zn1 122.8(3) . 4_575 ? N24 C25 C26 123.8(5) . . ? N24 C25 H25 118.1 . . ? C26 C25 H25 118.1 . . ? C25 C26 C21 120.3(5) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? O1S C1S N4 124.9(13) . . ? O1S C1S H1S 117.5 . . ? N4 C1S H1S 117.5 . . ? C1S N4 C2S 120.8(10) . . ? C1S N4 C3S 122.4(10) . . ? C2S N4 C3S 116.8(9) . . ? N4 C2S H2S1 109.5 . . ? N4 C2S H2S2 109.5 . . ? H2S1 C2S H2S2 109.5 . . ? N4 C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? N4 C3S H3S1 109.5 . . ? N4 C3S H3S2 109.5 . . ? H3S1 C3S H3S2 109.5 . . ? N4 C3S H3S3 109.5 . . ? H3S1 C3S H3S3 109.5 . . ? H3S2 C3S H3S3 109.5 . . ? C1 O3 Zn1 117.4(4) . . ? O4 C1 O3 127.4(6) . . ? O4 C1 H1A 116.3 . . ? O3 C1 H1A 116.3 . . ? H1W O1W H2W 101(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.88 1.93 2.806(5) 170.3 5_676 N2 H2 O4 0.88 1.96 2.797(6) 158.9 . O1W H1W O1 0.87(2) 2.11(3) 2.943(6) 161(7) 5_676 O1W H2W O1S 0.88(2) 1.92(4) 2.773(9) 162(9) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.973 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.098 _database_code_depnum_ccdc_archive 'CCDC 906704' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_trial1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H17 N4 O6 P Zn' _chemical_formula_weight 409.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.135(2) _cell_length_b 15.420(3) _cell_length_c 18.524(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4037.5(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5170 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 24.82 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 1.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6730 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 46565 _diffrn_reflns_av_R_equivalents 0.0831 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4988 _reflns_number_gt 3568 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The solvated methanol and water molecules could not be precisely located as they were disordered along the channel and hence the electron difference peaks due to solvents were refined as partially occupied O-atoms. The occupancies of these solvated atoms were by determined by initially fixing their Ueq values at 0.05 and then were approximated with meaningful occupancy factors. Thermogravimetric analysis confirmed one solvated methanol molecule and one molecule of water per formula unit. We have also provided a squeeze model for a better refinement data. ; _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^)+(0.0664P)^2^+11.2819P] 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 4988 _refine_ls_number_parameters 215 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0889 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1700 _refine_ls_wR_factor_gt 0.1557 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.66484(3) 1.03515(3) 0.35667(2) 0.02714(16) Uani 1 1 d . . . P1 P 0.84368(7) 0.99551(7) 0.46069(5) 0.0251(2) Uani 1 1 d . . . O1 O 0.7849(2) 0.9935(2) 0.39270(15) 0.0301(6) Uani 1 1 d . . . O2 O 0.9082(2) 1.07006(19) 0.47406(16) 0.0324(7) Uani 1 1 d . . . N1 N 0.9123(2) 0.9077(2) 0.4612(2) 0.0320(8) Uani 1 1 d . . . H1 H 0.9704 0.9161 0.4769 0.038 Uiso 1 1 calc R . . N2 N 0.7645(2) 0.9839(3) 0.52737(17) 0.0319(8) Uani 1 1 d . . . H2 H 0.7049 0.9797 0.5142 0.038 Uiso 1 1 calc R . . C1 C 0.5341(3) 0.9303(4) 0.4262(3) 0.0437(12) Uani 1 1 d . . . H1A H 0.4769 0.8984 0.4302 0.052 Uiso 1 1 calc R . . O3 O 0.5470(3) 0.9707(2) 0.36785(18) 0.0441(8) Uani 1 1 d . . . O4 O 0.5871(3) 0.9279(3) 0.4779(2) 0.0629(12) Uani 1 1 d . . . C11 C 0.8916(3) 0.8241(3) 0.4409(2) 0.0338(10) Uani 1 1 d . . . C12 C 0.8005(4) 0.7981(3) 0.4199(4) 0.0539(15) Uani 1 1 d . . . H12 H 0.7493 0.8380 0.4206 0.065 Uiso 1 1 calc R . . C13 C 0.7871(4) 0.7136(3) 0.3984(3) 0.0521(14) Uani 1 1 d . . . H13 H 0.7253 0.6965 0.3843 0.063 Uiso 1 1 calc R . . N14 N 0.8569(3) 0.6533(2) 0.3962(2) 0.0360(9) Uani 1 1 d . . . C15 C 0.9425(3) 0.6782(3) 0.4196(3) 0.0382(11) Uani 1 1 d . . . H15 H 0.9921 0.6366 0.4203 0.046 Uiso 1 1 calc R . . C16 C 0.9621(3) 0.7614(3) 0.4428(3) 0.0374(10) Uani 1 1 d . . . H16 H 1.0235 0.7757 0.4599 0.045 Uiso 1 1 calc R . . C21 C 0.7821(3) 0.9802(3) 0.6003(2) 0.0302(9) Uani 1 1 d . . . C22 C 0.7069(3) 0.9693(3) 0.6486(2) 0.0377(11) Uani 1 1 d . . . H22 H 0.6439 0.9649 0.6311 0.045 Uiso 1 1 calc R . . C23 C 0.7249(3) 0.9649(3) 0.7216(2) 0.0383(11) Uani 1 1 d . . . H23 H 0.6729 0.9577 0.7536 0.046 Uiso 1 1 calc R . . N24 N 0.8115(3) 0.9703(2) 0.74969(19) 0.0310(8) Uani 1 1 d . . . C25 C 0.8838(3) 0.9808(3) 0.7035(2) 0.0394(11) Uani 1 1 d . . . H25 H 0.9461 0.9844 0.7226 0.047 Uiso 1 1 calc R . . C26 C 0.8722(3) 0.9864(4) 0.6304(2) 0.0434(12) Uani 1 1 d . . . H26 H 0.9257 0.9946 0.6001 0.052 Uiso 1 1 calc R . . O1S O 0.5693(6) 0.6523(5) 0.3334(4) 0.0562(19) Uiso 0.50 1 d PU . . O2S O 0.535(2) 0.700(2) 0.3695(15) 0.122(5) Uiso 0.25 1 d PU . . O3S O 0.838(2) 0.750(2) 0.1332(16) 0.122(5) Uiso 0.25 1 d P . . O4S O 0.941(2) 0.840(2) 0.2504(18) 0.136(10) Uiso 0.25 1 d PU . . O5S O 0.710(2) 0.7344(19) 0.2356(16) 0.122(5) Uiso 0.25 1 d P . . O6S O 0.9150(16) 0.7468(16) 0.2331(13) 0.100(7) Uiso 0.25 1 d PU . . O7S O 1.243(2) 0.7687(17) 0.3925(16) 0.122(5) Uiso 0.25 1 d P . . 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 0.0296(3) 0.0334(3) 0.0184(2) -0.00240(19) -0.00064(19) 0.0004(2) P1 0.0248(5) 0.0310(5) 0.0194(5) -0.0023(4) -0.0027(4) -0.0022(4) O1 0.0269(15) 0.0436(17) 0.0199(13) -0.0018(12) -0.0036(11) -0.0016(13) O2 0.0301(16) 0.0326(15) 0.0345(16) -0.0005(13) -0.0071(13) -0.0043(13) N1 0.0238(18) 0.0308(18) 0.042(2) -0.0065(16) -0.0057(16) -0.0022(14) N2 0.0202(17) 0.056(2) 0.0194(16) -0.0021(15) -0.0035(13) -0.0024(16) C1 0.032(2) 0.061(3) 0.038(3) 0.002(2) -0.001(2) -0.016(2) O3 0.0401(19) 0.059(2) 0.0336(18) 0.0019(16) -0.0022(15) -0.0126(16) O4 0.035(2) 0.109(3) 0.044(2) 0.021(2) -0.0070(17) -0.026(2) C11 0.030(2) 0.033(2) 0.037(2) -0.0049(18) -0.0069(19) -0.0011(18) C12 0.030(2) 0.039(3) 0.093(4) -0.017(3) -0.020(3) 0.004(2) C13 0.035(3) 0.040(3) 0.081(4) -0.013(3) -0.018(3) -0.001(2) N14 0.036(2) 0.0322(19) 0.040(2) -0.0047(16) -0.0078(17) 0.0006(16) C15 0.032(2) 0.042(3) 0.041(3) -0.006(2) -0.008(2) 0.006(2) C16 0.027(2) 0.046(3) 0.040(3) -0.007(2) -0.0106(19) 0.0015(19) C21 0.026(2) 0.043(2) 0.0216(19) -0.0003(17) -0.0007(16) -0.0005(17) C22 0.023(2) 0.064(3) 0.027(2) 0.002(2) -0.0011(18) -0.001(2) C23 0.027(2) 0.061(3) 0.027(2) 0.005(2) 0.0017(18) -0.001(2) N24 0.0282(18) 0.045(2) 0.0192(16) 0.0025(16) 0.0006(14) 0.0010(16) C25 0.024(2) 0.072(3) 0.022(2) -0.001(2) -0.0028(17) -0.001(2) C26 0.026(2) 0.082(4) 0.022(2) -0.001(2) 0.0027(18) -0.002(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 O1 1.934(3) . ? Zn1 O3 1.950(3) . ? Zn1 N14 1.988(4) 6_765 ? Zn1 N24 2.011(4) 4_674 ? P1 O2 1.488(3) . ? P1 O1 1.509(3) . ? P1 N1 1.666(4) . ? P1 N2 1.676(4) . ? N1 C11 1.375(5) . ? N1 H1 0.8800 . ? N2 C21 1.374(5) . ? N2 H2 0.8800 . ? C1 O4 1.215(6) . ? C1 O3 1.260(6) . ? C1 H1A 0.9500 . ? C11 C16 1.388(6) . ? C11 C12 1.404(6) . ? C12 C13 1.376(7) . ? C12 H12 0.9500 . ? C13 N14 1.356(6) . ? C13 H13 0.9500 . ? N14 C15 1.342(6) . ? N14 Zn1 1.987(4) 6_755 ? C15 C16 1.382(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.395(6) . ? C21 C22 1.399(6) . ? C22 C23 1.378(6) . ? C22 H22 0.9500 . ? C23 N24 1.333(6) . ? C23 H23 0.9500 . ? N24 C25 1.342(6) . ? N24 Zn1 2.012(4) 4_675 ? C25 C26 1.367(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? O1S O2S 1.11(3) . ? O3S O7S 1.46(4) 8_556 ? O4S O6S 1.51(4) . ? O7S O3S 1.46(4) 8_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 122.92(14) . . ? O1 Zn1 N14 108.23(15) . 6_765 ? O3 Zn1 N14 107.23(16) . 6_765 ? O1 Zn1 N24 100.39(14) . 4_674 ? O3 Zn1 N24 103.00(14) . 4_674 ? N14 Zn1 N24 115.30(16) 6_765 4_674 ? O2 P1 O1 119.48(18) . . ? O2 P1 N1 105.65(18) . . ? O1 P1 N1 107.99(18) . . ? O2 P1 N2 111.66(18) . . ? O1 P1 N2 104.21(17) . . ? N1 P1 N2 107.31(19) . . ? P1 O1 Zn1 139.84(19) . . ? C11 N1 P1 129.5(3) . . ? C11 N1 H1 115.2 . . ? P1 N1 H1 115.2 . . ? C21 N2 P1 127.5(3) . . ? C21 N2 H2 116.3 . . ? P1 N2 H2 116.3 . . ? O4 C1 O3 127.0(5) . . ? O4 C1 H1A 116.5 . . ? O3 C1 H1A 116.5 . . ? C1 O3 Zn1 117.8(3) . . ? N1 C11 C16 119.5(4) . . ? N1 C11 C12 122.6(4) . . ? C16 C11 C12 117.9(4) . . ? C13 C12 C11 118.5(5) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? N14 C13 C12 123.9(5) . . ? N14 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C15 N14 C13 116.8(4) . . ? C15 N14 Zn1 121.4(3) . 6_755 ? C13 N14 Zn1 121.8(3) . 6_755 ? N14 C15 C16 123.2(4) . . ? N14 C15 H15 118.4 . . ? C16 C15 H15 118.4 . . ? C15 C16 C11 119.7(4) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? N2 C21 C26 123.8(4) . . ? N2 C21 C22 119.8(4) . . ? C26 C21 C22 116.5(4) . . ? C23 C22 C21 119.6(4) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? N24 C23 C22 123.3(4) . . ? N24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C23 N24 C25 117.3(4) . . ? C23 N24 Zn1 122.3(3) . 4_675 ? C25 N24 Zn1 120.4(3) . 4_675 ? N24 C25 C26 123.2(4) . . ? N24 C25 H25 118.4 . . ? C26 C25 H25 118.4 . . ? C25 C26 C21 120.1(4) . . ? C25 C26 H26 119.9 . . ? C21 C26 H26 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 Zn1 -86.2(3) . . . . ? N1 P1 O1 Zn1 153.2(3) . . . . ? N2 P1 O1 Zn1 39.3(3) . . . . ? O3 Zn1 O1 P1 -87.5(3) . . . . ? N14 Zn1 O1 P1 38.3(3) 6_765 . . . ? N24 Zn1 O1 P1 159.5(3) 4_674 . . . ? O2 P1 N1 C11 -168.9(4) . . . . ? O1 P1 N1 C11 -40.0(5) . . . . ? N2 P1 N1 C11 71.8(4) . . . . ? O2 P1 N2 C21 -50.8(4) . . . . ? O1 P1 N2 C21 178.9(4) . . . . ? N1 P1 N2 C21 64.5(4) . . . . ? O4 C1 O3 Zn1 1.2(8) . . . . ? O1 Zn1 O3 C1 37.9(4) . . . . ? N14 Zn1 O3 C1 -88.4(4) 6_765 . . . ? N24 Zn1 O3 C1 149.6(4) 4_674 . . . ? P1 N1 C11 C16 177.0(4) . . . . ? P1 N1 C11 C12 -5.0(7) . . . . ? N1 C11 C12 C13 178.1(5) . . . . ? C16 C11 C12 C13 -3.7(9) . . . . ? C11 C12 C13 N14 0.0(10) . . . . ? C12 C13 N14 C15 2.9(9) . . . . ? C12 C13 N14 Zn1 -174.7(5) . . . 6_755 ? C13 N14 C15 C16 -2.2(7) . . . . ? Zn1 N14 C15 C16 175.4(4) 6_755 . . . ? N14 C15 C16 C11 -1.4(8) . . . . ? N1 C11 C16 C15 -177.4(4) . . . . ? C12 C11 C16 C15 4.4(7) . . . . ? P1 N2 C21 C26 0.4(7) . . . . ? P1 N2 C21 C22 -179.3(4) . . . . ? N2 C21 C22 C23 179.5(5) . . . . ? C26 C21 C22 C23 -0.3(7) . . . . ? C21 C22 C23 N24 -0.2(8) . . . . ? C22 C23 N24 C25 0.2(7) . . . . ? C22 C23 N24 Zn1 179.4(4) . . . 4_675 ? C23 N24 C25 C26 0.3(8) . . . . ? Zn1 N24 C25 C26 -178.9(4) 4_675 . . . ? N24 C25 C26 C21 -0.8(9) . . . . ? N2 C21 C26 C25 -179.0(5) . . . . ? C22 C21 C26 C25 0.8(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.88 1.95 2.826(5) 171.3 5_776 N2 H2 O4 0.88 1.97 2.807(5) 159.5 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.335 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 906705' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ag175_sq _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H17 N4 O6 P Zn' _chemical_formula_weight 409.64 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 14.135(2) _cell_length_b 15.420(3) _cell_length_c 18.524(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4037.5(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5170 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 24.82 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 1.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6730 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 46565 _diffrn_reflns_av_R_equivalents 0.0779 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.23 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4988 _reflns_number_gt 3620 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The solvated methanol and water molecules could not be precicely located as they were disordered along the channel and have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON. ; _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^)+(0.0543P)^2^+2.4069P] 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 4988 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 Zn1 Zn 0.66487(2) 1.03516(2) 0.356659(17) 0.02676(11) Uani 1 1 d . . . P1 P 0.84368(5) 0.99552(5) 0.46064(4) 0.02481(16) Uani 1 1 d . . . O1 O 0.78498(14) 0.99366(13) 0.39285(10) 0.0300(4) Uani 1 1 d . . . O2 O 0.90803(14) 1.06976(13) 0.47423(11) 0.0322(5) Uani 1 1 d . . . N1 N 0.91229(17) 0.90752(14) 0.46133(13) 0.0314(5) Uani 1 1 d . . . H1 H 0.9703 0.9158 0.4772 0.038 Uiso 1 1 calc R . . N2 N 0.76435(16) 0.98410(16) 0.52723(12) 0.0304(6) Uani 1 1 d . . . H2 H 0.7047 0.9801 0.5140 0.037 Uiso 1 1 calc R . . C1 C 0.5341(2) 0.9304(2) 0.42612(18) 0.0435(8) Uani 1 1 d . . . H1A H 0.4765 0.8991 0.4304 0.052 Uiso 1 1 calc R . . O3 O 0.54716(17) 0.97013(15) 0.36786(12) 0.0442(6) Uani 1 1 d . . . O4 O 0.58722(17) 0.9277(2) 0.47760(14) 0.0622(8) Uani 1 1 d . . . C11 C 0.8915(2) 0.82399(18) 0.44078(16) 0.0331(7) Uani 1 1 d . . . C12 C 0.8010(2) 0.7978(2) 0.4196(2) 0.0534(10) Uani 1 1 d . . . H12 H 0.7497 0.8377 0.4199 0.064 Uiso 1 1 calc R . . C13 C 0.7874(3) 0.7142(2) 0.3983(2) 0.0524(10) Uani 1 1 d . . . H13 H 0.7256 0.6972 0.3841 0.063 Uiso 1 1 calc R . . N14 N 0.85704(18) 0.65367(16) 0.39635(14) 0.0356(6) Uani 1 1 d . . . C15 C 0.9423(2) 0.6786(2) 0.41933(17) 0.0374(7) Uani 1 1 d . . . H15 H 0.9920 0.6371 0.4196 0.045 Uiso 1 1 calc R . . C16 C 0.9619(2) 0.7613(2) 0.44268(17) 0.0377(7) Uani 1 1 d . . . H16 H 1.0233 0.7755 0.4600 0.045 Uiso 1 1 calc R . . C21 C 0.7820(2) 0.98020(19) 0.60050(15) 0.0299(6) Uani 1 1 d . . . C22 C 0.7067(2) 0.9691(2) 0.64863(16) 0.0368(7) Uani 1 1 d . . . H22 H 0.6437 0.9645 0.6311 0.044 Uiso 1 1 calc R . . C23 C 0.7247(2) 0.9650(2) 0.72143(16) 0.0378(7) Uani 1 1 d . . . H23 H 0.6727 0.9580 0.7534 0.045 Uiso 1 1 calc R . . N24 N 0.81157(17) 0.97030(16) 0.74958(13) 0.0310(5) Uani 1 1 d . . . C25 C 0.8838(2) 0.9809(2) 0.70357(16) 0.0392(8) Uani 1 1 d . . . H25 H 0.9460 0.9846 0.7227 0.047 Uiso 1 1 calc R . . C26 C 0.8723(2) 0.9865(3) 0.63039(16) 0.0441(9) Uani 1 1 d . . . H26 H 0.9257 0.9946 0.6000 0.053 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 0.02922(19) 0.03292(18) 0.01814(16) -0.00245(13) -0.00071(14) 0.00040(14) P1 0.0244(4) 0.0307(4) 0.0193(3) -0.0025(3) -0.0024(3) -0.0023(3) O1 0.0275(11) 0.0419(11) 0.0206(10) -0.0015(9) -0.0031(8) -0.0007(9) O2 0.0303(11) 0.0322(10) 0.0340(11) -0.0007(9) -0.0071(9) -0.0052(9) N1 0.0247(13) 0.0299(12) 0.0395(14) -0.0051(11) -0.0056(11) -0.0035(10) N2 0.0193(12) 0.0533(16) 0.0187(11) -0.0019(10) -0.0041(9) -0.0024(10) C1 0.0325(18) 0.062(2) 0.0358(18) 0.0013(16) -0.0012(15) -0.0162(16) O3 0.0404(13) 0.0577(15) 0.0345(12) 0.0009(11) -0.0022(10) -0.0135(11) O4 0.0363(14) 0.107(2) 0.0429(15) 0.0216(15) -0.0057(12) -0.0258(14) C11 0.0298(16) 0.0330(15) 0.0365(17) -0.0039(13) -0.0066(13) 0.0002(12) C12 0.0285(17) 0.0385(18) 0.093(3) -0.0179(19) -0.0226(19) 0.0050(14) C13 0.0322(18) 0.0402(18) 0.085(3) -0.0138(18) -0.0186(19) 0.0015(14) N14 0.0348(15) 0.0327(13) 0.0393(15) -0.0053(11) -0.0080(11) -0.0006(11) C15 0.0302(16) 0.0401(17) 0.0420(18) -0.0066(14) -0.0093(14) 0.0049(13) C16 0.0259(15) 0.0455(18) 0.0416(18) -0.0083(14) -0.0110(13) 0.0031(13) C21 0.0250(15) 0.0437(17) 0.0209(13) -0.0006(12) -0.0005(11) 0.0000(12) C22 0.0222(15) 0.062(2) 0.0258(15) 0.0015(14) -0.0004(12) -0.0003(14) C23 0.0274(16) 0.059(2) 0.0265(15) 0.0030(14) 0.0021(12) -0.0020(14) N24 0.0269(13) 0.0463(14) 0.0197(11) 0.0033(11) 0.0010(9) 0.0026(11) C25 0.0229(15) 0.073(2) 0.0220(14) -0.0009(15) -0.0039(12) -0.0002(15) C26 0.0252(16) 0.087(3) 0.0202(15) -0.0032(15) 0.0025(12) -0.0022(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O1 1.934(2) . ? Zn1 O3 1.954(2) . ? Zn1 N14 1.994(2) 6_765 ? Zn1 N24 2.013(2) 4_674 ? P1 O2 1.484(2) . ? P1 O1 1.505(2) . ? P1 N1 1.668(2) . ? P1 N2 1.676(2) . ? N1 C11 1.375(3) . ? N1 H1 0.8800 . ? N2 C21 1.381(3) . ? N2 H2 0.8800 . ? C1 O4 1.215(4) . ? C1 O3 1.255(4) . ? C1 H1A 0.9500 . ? C11 C16 1.388(4) . ? C11 C12 1.398(4) . ? C12 C13 1.362(5) . ? C12 H12 0.9500 . ? C13 N14 1.357(4) . ? C13 H13 0.9500 . ? N14 C15 1.335(4) . ? N14 Zn1 1.994(2) 6_755 ? C15 C16 1.375(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.394(4) . ? C21 C22 1.398(4) . ? C22 C23 1.374(4) . ? C22 H22 0.9500 . ? C23 N24 1.337(4) . ? C23 H23 0.9500 . ? N24 C25 1.340(4) . ? N24 Zn1 2.013(2) 4_675 ? C25 C26 1.368(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Zn1 O3 122.74(10) . . ? O1 Zn1 N14 108.16(10) . 6_765 ? O3 Zn1 N14 107.40(10) . 6_765 ? O1 Zn1 N24 100.51(9) . 4_674 ? O3 Zn1 N24 102.95(10) . 4_674 ? N14 Zn1 N24 115.30(10) 6_765 4_674 ? O2 P1 O1 119.61(12) . . ? O2 P1 N1 105.66(12) . . ? O1 P1 N1 108.14(12) . . ? O2 P1 N2 111.49(12) . . ? O1 P1 N2 104.07(12) . . ? N1 P1 N2 107.33(13) . . ? P1 O1 Zn1 140.05(13) . . ? C11 N1 P1 129.5(2) . . ? C11 N1 H1 115.3 . . ? P1 N1 H1 115.3 . . ? C21 N2 P1 127.4(2) . . ? C21 N2 H2 116.3 . . ? P1 N2 H2 116.3 . . ? O4 C1 O3 126.9(3) . . ? O4 C1 H1A 116.5 . . ? O3 C1 H1A 116.5 . . ? C1 O3 Zn1 117.9(2) . . ? N1 C11 C16 119.5(3) . . ? N1 C11 C12 123.0(3) . . ? C16 C11 C12 117.6(3) . . ? C13 C12 C11 118.9(3) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? N14 C13 C12 123.9(3) . . ? N14 C13 H13 118.1 . . ? C12 C13 H13 118.1 . . ? C15 N14 C13 116.6(3) . . ? C15 N14 Zn1 121.5(2) . 6_755 ? C13 N14 Zn1 121.9(2) . 6_755 ? N14 C15 C16 123.3(3) . . ? N14 C15 H15 118.3 . . ? C16 C15 H15 118.3 . . ? C15 C16 C11 119.6(3) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? N2 C21 C26 123.5(3) . . ? N2 C21 C22 119.6(3) . . ? C26 C21 C22 116.8(3) . . ? C23 C22 C21 119.4(3) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? N24 C23 C22 123.4(3) . . ? N24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C23 N24 C25 117.3(3) . . ? C23 N24 Zn1 122.3(2) . 4_675 ? C25 N24 Zn1 120.4(2) . 4_675 ? N24 C25 C26 123.2(3) . . ? N24 C25 H25 118.4 . . ? C26 C25 H25 118.4 . . ? C25 C26 C21 119.9(3) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 Zn1 -86.2(2) . . . . ? N1 P1 O1 Zn1 152.95(18) . . . . ? N2 P1 O1 Zn1 39.0(2) . . . . ? O3 Zn1 O1 P1 -87.4(2) . . . . ? N14 Zn1 O1 P1 38.4(2) 6_765 . . . ? N24 Zn1 O1 P1 159.6(2) 4_674 . . . ? O2 P1 N1 C11 -168.9(3) . . . . ? O1 P1 N1 C11 -39.7(3) . . . . ? N2 P1 N1 C11 72.0(3) . . . . ? O2 P1 N2 C21 -50.9(3) . . . . ? O1 P1 N2 C21 178.8(2) . . . . ? N1 P1 N2 C21 64.3(3) . . . . ? O4 C1 O3 Zn1 0.1(5) . . . . ? O1 Zn1 O3 C1 38.3(3) . . . . ? N14 Zn1 O3 C1 -87.8(3) 6_765 . . . ? N24 Zn1 O3 C1 150.1(3) 4_674 . . . ? P1 N1 C11 C16 176.8(2) . . . . ? P1 N1 C11 C12 -5.0(5) . . . . ? N1 C11 C12 C13 178.4(4) . . . . ? C16 C11 C12 C13 -3.4(6) . . . . ? C11 C12 C13 N14 0.0(7) . . . . ? C12 C13 N14 C15 2.5(6) . . . . ? C12 C13 N14 Zn1 -174.6(3) . . . 6_755 ? C13 N14 C15 C16 -1.5(5) . . . . ? Zn1 N14 C15 C16 175.6(3) 6_755 . . . ? N14 C15 C16 C11 -2.0(5) . . . . ? N1 C11 C16 C15 -177.3(3) . . . . ? C12 C11 C16 C15 4.4(5) . . . . ? P1 N2 C21 C26 0.8(5) . . . . ? P1 N2 C21 C22 -179.0(2) . . . . ? N2 C21 C22 C23 179.8(3) . . . . ? C26 C21 C22 C23 -0.1(5) . . . . ? C21 C22 C23 N24 -0.5(5) . . . . ? C22 C23 N24 C25 0.5(5) . . . . ? C22 C23 N24 Zn1 179.5(2) . . . 4_675 ? C23 N24 C25 C26 0.2(5) . . . . ? Zn1 N24 C25 C26 -178.9(3) 4_675 . . . ? N24 C25 C26 C21 -0.7(6) . . . . ? N2 C21 C26 C25 -179.2(3) . . . . ? C22 C21 C26 C25 0.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.88 1.95 2.828(3) 171.9 5_776 N2 H2 O4 0.88 1.97 2.805(3) 158.9 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.026 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.072 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.026 0.231 0.750 393 87 ' ' 2 -0.025 0.269 0.250 393 86 ' ' 3 -0.021 0.731 0.750 393 87 ' ' 4 -0.026 0.769 0.250 393 86 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 906706' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_mo_ag168a_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 N5 O6 P Zn' _chemical_formula_weight 450.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 11.5224(15) _cell_length_b 13.9000(19) _cell_length_c 11.7135(16) _cell_angle_alpha 90.00 _cell_angle_beta 103.699(3) _cell_angle_gamma 90.00 _cell_volume 1822.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2121 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 24.50 _exptl_crystal_description Prism _exptl_crystal_colour colourless' _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6730 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13936 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0613 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4492 _reflns_number_gt 3307 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _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' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The solvated DMF was disordered and hence was split over two positions and refined isotropically with occupancy factors and similar-distance and similar U restraints. One of the disordered DMF O-atom has a low Ueq value and hence the oxygen atoms both the disordered fragments were refiend with equal Ueq values. ; _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^)+(0.0517P)^2^+2.5327P] 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 4492 _refine_ls_number_parameters 244 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.16779(3) 0.61520(3) 1.14736(3) 0.01393(12) Uani 1 1 d . . . P1 P 0.26545(7) 0.82890(6) 1.05630(7) 0.01371(19) Uani 1 1 d . . . O1 O 0.3650(2) 0.88130(17) 1.1362(2) 0.0183(5) Uani 1 1 d . . . O2 O 0.1911(2) 0.75953(17) 1.1063(2) 0.0160(5) Uani 1 1 d . . . O3 O 0.1422(2) 0.46137(18) 1.1588(2) 0.0175(5) Uani 1 1 d D . . H1W H 0.081(3) 0.452(3) 1.115(3) 0.026 Uiso 1 1 d DU . . H2W H 0.147(4) 0.433(3) 1.218(3) 0.026 Uiso 1 1 d DU . . N1 N 0.1779(2) 0.9151(2) 0.9802(2) 0.0161(6) Uani 1 1 d . . . H1 H 0.2075 0.9737 0.9889 0.019 Uiso 1 1 calc R . . N2 N 0.3180(2) 0.7635(2) 0.9586(2) 0.0174(6) Uani 1 1 d . . . H2 H 0.2941 0.7032 0.9502 0.021 Uiso 1 1 calc R . . C1 C 0.1563(4) 0.5618(3) 0.9196(3) 0.0288(9) Uani 1 1 d . . . H1A H 0.1250 0.5378 0.8426 0.035 Uiso 1 1 calc R . . O4 O 0.0810(2) 0.58906(19) 0.9768(2) 0.0238(6) Uani 1 1 d . . . O5 O 0.2655(3) 0.5635(2) 0.9546(3) 0.0351(7) Uani 1 1 d . . . O6 O 0.2704(4) 0.1054(3) 0.9325(5) 0.0487(12) Uiso 0.791(5) 1 d PDU A 1 C2 C 0.3291(5) 0.1653(5) 0.9033(5) 0.0412(14) Uiso 0.791(5) 1 d PDU A 1 H2A H 0.3879 0.1429 0.8649 0.049 Uiso 0.791(5) 1 calc PR A 1 N3 N 0.3249(7) 0.2595(5) 0.9166(7) 0.027(2) Uiso 0.791(5) 1 d PDU A 1 C3 C 0.3998(6) 0.3280(5) 0.8766(6) 0.0474(16) Uiso 0.791(5) 1 d PDU A 1 H3A H 0.3781 0.3932 0.8956 0.071 Uiso 0.791(5) 1 calc PR A 1 H3B H 0.3890 0.3219 0.7914 0.071 Uiso 0.791(5) 1 calc PR A 1 H3C H 0.4835 0.3156 0.9156 0.071 Uiso 0.791(5) 1 calc PR A 1 C4 C 0.2395(5) 0.3034(4) 0.9733(5) 0.0398(13) Uiso 0.791(5) 1 d PDU A 1 H4A H 0.2491 0.3735 0.9739 0.060 Uiso 0.791(5) 1 calc PR A 1 H4B H 0.2531 0.2799 1.0542 0.060 Uiso 0.791(5) 1 calc PR A 1 H4C H 0.1583 0.2867 0.9302 0.060 Uiso 0.791(5) 1 calc PR A 1 O6' O 0.2436(16) 0.1133(12) 0.9756(17) 0.0487(12) Uiso 0.209(5) 1 d PDU A 2 C2' C 0.258(2) 0.1942(15) 0.972(2) 0.059(7) Uiso 0.209(5) 1 d PDU A 2 H2' H 0.2220 0.2299 1.0239 0.071 Uiso 0.209(5) 1 calc PR A 2 N3' N 0.316(3) 0.2474(13) 0.911(2) 0.024(8) Uiso 0.209(5) 1 d PDU A 2 C3' C 0.386(3) 0.219(2) 0.834(3) 0.084(10) Uiso 0.209(5) 1 d PDU A 2 H3'1 H 0.4187 0.2759 0.8039 0.126 Uiso 0.209(5) 1 calc PR A 2 H3'2 H 0.3366 0.1826 0.7686 0.126 Uiso 0.209(5) 1 calc PR A 2 H3'3 H 0.4516 0.1780 0.8764 0.126 Uiso 0.209(5) 1 calc PR A 2 C4' C 0.3150(19) 0.3508(13) 0.929(2) 0.0398(13) Uiso 0.209(5) 1 d PDU A 2 H4'1 H 0.3578 0.3824 0.8764 0.060 Uiso 0.209(5) 1 calc PR A 2 H4'2 H 0.3545 0.3658 1.0108 0.060 Uiso 0.209(5) 1 calc PR A 2 H4'3 H 0.2324 0.3740 0.9120 0.060 Uiso 0.209(5) 1 calc PR A 2 C11 C 0.0656(3) 0.9067(2) 0.9057(3) 0.0166(7) Uani 1 1 d . . . C12 C 0.0125(3) 0.9867(3) 0.8414(3) 0.0221(8) Uani 1 1 d . . . H12 H 0.0538 1.0464 0.8491 0.027 Uiso 1 1 calc R . . C13 C -0.0987(3) 0.9793(3) 0.7675(3) 0.0222(8) Uani 1 1 d . . . H13 H -0.1322 1.0348 0.7250 0.027 Uiso 1 1 calc R . . N14 N -0.1633(2) 0.8970(2) 0.7517(2) 0.0177(6) Uani 1 1 d . . . C15 C -0.1122(3) 0.8201(3) 0.8150(3) 0.0195(7) Uani 1 1 d . . . H15 H -0.1559 0.7615 0.8063 0.023 Uiso 1 1 calc R . . C16 C -0.0009(3) 0.8213(3) 0.8912(3) 0.0204(7) Uani 1 1 d . . . H16 H 0.0303 0.7650 0.9334 0.024 Uiso 1 1 calc R . . C21 C 0.3938(3) 0.7926(2) 0.8903(3) 0.0156(7) Uani 1 1 d . . . C22 C 0.4331(3) 0.7256(3) 0.8181(3) 0.0193(7) Uani 1 1 d . . . H22 H 0.4073 0.6605 0.8162 0.023 Uiso 1 1 calc R . . C23 C 0.5093(3) 0.7545(3) 0.7497(3) 0.0192(7) Uani 1 1 d . . . H23 H 0.5338 0.7081 0.7006 0.023 Uiso 1 1 calc R . . N24 N 0.5511(2) 0.8457(2) 0.7488(2) 0.0149(6) Uani 1 1 d . . . C25 C 0.5140(3) 0.9093(3) 0.8198(3) 0.0184(7) Uani 1 1 d . . . H25 H 0.5436 0.9732 0.8226 0.022 Uiso 1 1 calc R . . C26 C 0.4354(3) 0.8870(3) 0.8886(3) 0.0178(7) Uani 1 1 d . . . H26 H 0.4099 0.9355 0.9344 0.021 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 0.01203(19) 0.0168(2) 0.01302(19) 0.00054(15) 0.00315(14) -0.00040(15) P1 0.0131(4) 0.0152(4) 0.0132(4) -0.0009(3) 0.0040(3) -0.0012(3) O1 0.0191(12) 0.0198(13) 0.0154(11) -0.0028(10) 0.0026(10) -0.0047(10) O2 0.0154(11) 0.0182(13) 0.0157(11) 0.0013(9) 0.0066(9) -0.0018(9) O3 0.0178(12) 0.0189(14) 0.0147(12) 0.0014(10) 0.0019(10) -0.0012(10) N1 0.0119(13) 0.0138(14) 0.0218(15) 0.0006(11) 0.0024(11) -0.0013(11) N2 0.0197(14) 0.0150(15) 0.0198(14) -0.0043(11) 0.0092(12) -0.0045(11) C1 0.042(2) 0.022(2) 0.0234(19) -0.0027(15) 0.0093(18) -0.0140(17) O4 0.0293(14) 0.0217(14) 0.0177(12) 0.0020(10) 0.0001(11) -0.0071(11) O5 0.0338(16) 0.0245(16) 0.0472(18) -0.0023(13) 0.0102(14) -0.0074(13) C11 0.0149(16) 0.0181(18) 0.0173(16) 0.0006(13) 0.0051(13) 0.0022(13) C12 0.0187(17) 0.0178(19) 0.030(2) 0.0004(15) 0.0051(15) -0.0019(14) C13 0.0176(17) 0.0200(19) 0.0285(19) 0.0034(15) 0.0045(15) 0.0022(14) N14 0.0145(13) 0.0187(16) 0.0189(14) 0.0023(12) 0.0024(11) 0.0000(12) C15 0.0182(17) 0.0209(19) 0.0190(17) 0.0026(14) 0.0036(14) -0.0010(14) C16 0.0188(17) 0.0198(19) 0.0210(17) 0.0059(14) 0.0015(14) 0.0013(14) C21 0.0138(15) 0.0175(18) 0.0161(16) 0.0001(13) 0.0049(13) -0.0015(13) C22 0.0221(18) 0.0135(17) 0.0241(18) -0.0047(14) 0.0090(15) -0.0030(13) C23 0.0199(17) 0.0183(19) 0.0210(17) -0.0049(14) 0.0082(14) -0.0027(14) N24 0.0141(13) 0.0138(14) 0.0173(14) 0.0002(11) 0.0046(11) 0.0010(11) C25 0.0192(17) 0.0182(18) 0.0176(16) -0.0009(13) 0.0042(14) 0.0002(14) C26 0.0197(16) 0.0187(18) 0.0171(16) -0.0040(13) 0.0089(13) -0.0028(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O4 2.044(2) . ? Zn1 N14 2.045(3) 4_676 ? Zn1 N24 2.067(3) 4_576 ? Zn1 O2 2.095(2) . ? Zn1 O3 2.167(3) . ? P1 O1 1.488(2) . ? P1 O2 1.498(2) . ? P1 N1 1.680(3) . ? P1 N2 1.682(3) . ? O3 H1W 0.78(3) . ? O3 H2W 0.79(3) . ? N1 C11 1.383(4) . ? N1 H1 0.8800 . ? N2 C21 1.377(4) . ? N2 H2 0.8800 . ? C1 O5 1.228(5) . ? C1 O4 1.273(5) . ? C1 H1A 0.9500 . ? O6 C2 1.173(7) . ? C2 N3 1.321(9) . ? C2 H2A 0.9500 . ? N3 C3 1.435(8) . ? N3 C4 1.447(8) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? O6' C2' 1.139(17) . ? C2' N3' 1.312(17) . ? C2' H2' 0.9500 . ? N3' C3' 1.407(18) . ? N3' C4' 1.452(17) . ? C3' H3'1 0.9800 . ? C3' H3'2 0.9800 . ? C3' H3'3 0.9800 . ? C4' H4'1 0.9800 . ? C4' H4'2 0.9800 . ? C4' H4'3 0.9800 . ? C11 C12 1.400(5) . ? C11 C16 1.401(5) . ? C12 C13 1.370(5) . ? C12 H12 0.9500 . ? C13 N14 1.353(5) . ? C13 H13 0.9500 . ? N14 C15 1.353(4) . ? N14 Zn1 2.045(3) 4_575 ? C15 C16 1.379(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.399(5) . ? C21 C22 1.404(4) . ? C22 C23 1.382(4) . ? C22 H22 0.9500 . ? C23 N24 1.356(4) . ? C23 H23 0.9500 . ? N24 C25 1.351(4) . ? N24 Zn1 2.067(3) 4_675 ? C25 C26 1.382(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Zn1 N14 138.19(11) . 4_676 ? O4 Zn1 N24 112.00(11) . 4_576 ? N14 Zn1 N24 109.55(11) 4_676 4_576 ? O4 Zn1 O2 90.33(10) . . ? N14 Zn1 O2 93.50(11) 4_676 . ? N24 Zn1 O2 90.93(10) 4_576 . ? O4 Zn1 O3 80.96(10) . . ? N14 Zn1 O3 90.29(11) 4_676 . ? N24 Zn1 O3 96.18(10) 4_576 . ? O2 Zn1 O3 170.34(9) . . ? O1 P1 O2 119.75(14) . . ? O1 P1 N1 105.16(15) . . ? O2 P1 N1 109.83(14) . . ? O1 P1 N2 110.13(14) . . ? O2 P1 N2 104.43(14) . . ? N1 P1 N2 106.99(15) . . ? P1 O2 Zn1 145.31(14) . . ? Zn1 O3 H1W 104(3) . . ? Zn1 O3 H2W 124(3) . . ? H1W O3 H2W 111(4) . . ? C11 N1 P1 129.0(2) . . ? C11 N1 H1 115.5 . . ? P1 N1 H1 115.5 . . ? C21 N2 P1 128.0(2) . . ? C21 N2 H2 116.0 . . ? P1 N2 H2 116.0 . . ? O5 C1 O4 126.3(4) . . ? O5 C1 H1A 116.9 . . ? O4 C1 H1A 116.9 . . ? C1 O4 Zn1 109.3(2) . . ? O6 C2 N3 129.0(6) . . ? O6 C2 H2A 115.5 . . ? N3 C2 H2A 115.5 . . ? C2 N3 C3 125.3(6) . . ? C2 N3 C4 121.3(6) . . ? C3 N3 C4 113.4(6) . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N3 C4 H4A 109.5 . . ? N3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O6' C2' N3' 132(2) . . ? O6' C2' H2' 113.9 . . ? N3' C2' H2' 113.9 . . ? C2' N3' C3' 129(2) . . ? C2' N3' C4' 117.4(17) . . ? C3' N3' C4' 113.2(18) . . ? N3' C3' H3'1 109.5 . . ? N3' C3' H3'2 109.5 . . ? H3'1 C3' H3'2 109.5 . . ? N3' C3' H3'3 109.5 . . ? H3'1 C3' H3'3 109.5 . . ? H3'2 C3' H3'3 109.5 . . ? N3' C4' H4'1 109.5 . . ? N3' C4' H4'2 109.5 . . ? H4'1 C4' H4'2 109.5 . . ? N3' C4' H4'3 109.5 . . ? H4'1 C4' H4'3 109.5 . . ? H4'2 C4' H4'3 109.5 . . ? N1 C11 C12 119.8(3) . . ? N1 C11 C16 123.4(3) . . ? C12 C11 C16 116.8(3) . . ? C13 C12 C11 120.3(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N14 C13 C12 123.5(3) . . ? N14 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? C13 N14 C15 116.0(3) . . ? C13 N14 Zn1 124.5(2) . 4_575 ? C15 N14 Zn1 119.4(2) . 4_575 ? N14 C15 C16 124.2(3) . . ? N14 C15 H15 117.9 . . ? C16 C15 H15 117.9 . . ? C15 C16 C11 119.1(3) . . ? C15 C16 H16 120.4 . . ? C11 C16 H16 120.4 . . ? N2 C21 C26 123.4(3) . . ? N2 C21 C22 119.6(3) . . ? C26 C21 C22 116.9(3) . . ? C23 C22 C21 119.8(3) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? N24 C23 C22 123.5(3) . . ? N24 C23 H23 118.3 . . ? C22 C23 H23 118.3 . . ? C25 N24 C23 116.3(3) . . ? C25 N24 Zn1 121.7(2) . 4_675 ? C23 N24 Zn1 122.0(2) . 4_675 ? N24 C25 C26 124.0(3) . . ? N24 C25 H25 118.0 . . ? C26 C25 H25 118.0 . . ? C25 C26 C21 119.5(3) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1W O4 0.78(3) 2.01(3) 2.775(3) 170(4) 3_567 O3 H2W O1 0.79(3) 1.89(3) 2.666(3) 170(4) 2_547 N1 H1 O6' 0.88 2.00 2.862(17) 166.5 1_565 N1 H1 O6 0.88 2.13 2.955(5) 155.6 1_565 N2 H2 O5 0.88 1.97 2.842(4) 169.7 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.471 _refine_diff_density_min -1.089 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 906707'