# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Fabrizia Grepioni' _publ_contact_author_email FABRIZIA.GREPIONI@UNIBO.IT _publ_section_title ; Drug-containing coordination and hydrogen bonding networks obtained mechanochemically ; loop_ _publ_author_name 'Fabrizia Grepioni' 'Vania Andre' 'Dario Braga' 'Maria Duarte' # Attachment '1-rev.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 723417' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H12 Ag N3 O9' _chemical_formula_weight 474.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pmcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y, z' 'x, -y-1/2, z-1/2' _cell_length_a 28.665(3) _cell_length_b 5.402(7) _cell_length_c 10.882(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1685(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.253 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8944 _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 5150 _diffrn_reflns_av_R_equivalents 0.0894 _diffrn_reflns_av_sigmaI/netI 0.2689 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1835 _reflns_number_gt 659 _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^)+(0.0284P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1835 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2363 _refine_ls_R_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.864 _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 Ag1 Ag 0.2500 0.32495(15) 0.26470(11) 0.0481(4) Uani 1 2 d S . . O1 O 0.13469(13) -0.2171(8) -0.0813(5) 0.0404(16) Uani 1 1 d . . . H1 H 0.1124 -0.3074 -0.0964 0.061 Uiso 1 1 calc R . . O2 O 0.05162(16) -0.4054(9) -0.0454(5) 0.0438(18) Uani 1 1 d . . . O3 O 0.00694(16) -0.2419(9) 0.1037(6) 0.0572(18) Uani 1 1 d . . . H2 H -0.0087 -0.3675 0.0939 0.086 Uiso 1 1 calc R . . N1 N 0.18111(16) 0.4712(9) 0.1657(6) 0.033(2) Uani 1 1 d . . . C1 C 0.08095(14) -0.0682(8) 0.0738(5) 0.027(2) Uani 1 1 d G . . C2 C 0.12300(16) -0.0564(8) 0.0104(4) 0.023(2) Uani 1 1 d G . . C3 C 0.15591(12) 0.1220(9) 0.0413(5) 0.031(2) Uani 1 1 d G . . H3 H 0.1840 0.1299 -0.0011 0.037 Uiso 1 1 calc R . . C4 C 0.14677(13) 0.2887(8) 0.1356(5) 0.030(2) Uani 1 1 d G . . C5 C 0.10473(16) 0.2770(9) 0.1990(4) 0.044(3) Uani 1 1 d G . . H5 H 0.0986 0.3885 0.2620 0.052 Uiso 1 1 calc R . . C6 C 0.07182(12) 0.0985(9) 0.1680(5) 0.042(3) Uani 1 1 d G . . H6 H 0.0437 0.0907 0.2104 0.051 Uiso 1 1 calc R . . C7 C 0.0458(2) -0.2569(15) 0.0363(8) 0.034(2) Uani 1 1 d . . . N2 N 0.2500 -0.153(2) 0.3864(14) 0.044(4) Uani 1 2 d S . . O4 O 0.2500 -0.3456(14) 0.4411(8) 0.050(3) Uani 1 2 d S . . O5 O 0.2500 0.0519(14) 0.4458(9) 0.053(3) Uani 1 2 d S . . O6 O 0.2500 -0.1363(16) 0.2750(11) 0.063(3) Uani 1 2 d S . . 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 Ag1 0.0498(4) 0.0405(4) 0.0541(10) 0.0063(8) 0.000 0.000 O1 0.035(3) 0.040(3) 0.046(5) -0.008(4) 0.011(3) -0.012(2) O2 0.045(3) 0.054(4) 0.033(5) -0.025(4) 0.012(3) -0.021(3) O3 0.049(3) 0.068(4) 0.054(5) -0.021(4) 0.018(3) -0.033(3) N1 0.028(3) 0.030(3) 0.040(6) 0.005(4) -0.022(3) -0.009(3) C1 0.026(4) 0.048(5) 0.009(6) 0.009(5) 0.004(4) -0.005(4) C2 0.030(4) 0.025(4) 0.015(6) -0.003(5) 0.007(4) 0.010(4) C3 0.024(3) 0.027(4) 0.042(7) 0.005(5) 0.006(4) -0.003(3) C4 0.032(4) 0.035(4) 0.022(6) 0.003(5) -0.007(4) 0.013(4) C5 0.043(4) 0.056(5) 0.032(7) -0.031(5) 0.007(4) -0.010(4) C6 0.036(4) 0.064(6) 0.027(7) -0.011(5) 0.010(4) -0.012(4) C7 0.034(4) 0.046(5) 0.023(7) 0.006(5) 0.000(5) -0.010(5) N2 0.019(4) 0.048(8) 0.064(12) 0.048(11) 0.000 0.000 O4 0.057(4) 0.040(5) 0.054(8) 0.035(6) 0.000 0.000 O5 0.064(5) 0.029(5) 0.067(10) -0.012(6) 0.000 0.000 O6 0.097(6) 0.020(4) 0.071(9) 0.018(8) 0.000 0.000 _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 Ag1 N1 2.384(5) . ? Ag1 N1 2.384(5) 7_655 ? Ag1 O5 2.462(9) . ? Ag1 O6 2.494(10) . ? O1 C2 1.365(6) . ? O1 H1 0.8200 . ? O2 C7 1.209(8) . ? O3 C7 1.337(8) . ? O3 H2 0.8200 . ? N1 C4 1.431(6) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.490(8) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? N2 O4 1.198(12) . ? N2 O6 1.215(13) . ? N2 O5 1.282(14) . ? 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 Ag1 N1 111.8(3) . 7_655 ? N1 Ag1 O5 124.09(14) . . ? N1 Ag1 O5 124.09(13) 7_655 . ? N1 Ag1 O6 110.57(19) . . ? N1 Ag1 O6 110.57(19) 7_655 . ? O5 Ag1 O6 50.6(3) . . ? C2 O1 H1 109.5 . . ? C7 O3 H2 109.5 . . ? C4 N1 Ag1 116.4(3) . . ? C2 C1 C6 120.0 . . ? C2 C1 C7 118.8(5) . . ? C6 C1 C7 121.2(5) . . ? O1 C2 C3 116.8(4) . . ? O1 C2 C1 123.1(4) . . ? C3 C2 C1 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 N1 121.0(4) . . ? C3 C4 N1 119.0(4) . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O2 C7 O3 124.0(7) . . ? O2 C7 C1 124.2(7) . . ? O3 C7 C1 111.8(7) . . ? O4 N2 O6 124.1(16) . . ? O4 N2 O5 119.9(14) . . ? O6 N2 O5 116.0(14) . . ? N2 O5 Ag1 96.6(9) . . ? N2 O6 Ag1 96.9(10) . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.623 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.110 # Attachment '1H2O-rev.CIF' data_1_H2O _database_code_depnum_ccdc_archive 'CCDC 723418' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 Ag2 N6 O20' _chemical_formula_weight 984.30 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' Ag Ag -0.8971 1.1015 '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 7.580(5) _cell_length_b 7.627(5) _cell_length_c 17.111(5) _cell_angle_alpha 92.062(5) _cell_angle_beta 97.578(5) _cell_angle_gamma 118.434(5) _cell_volume 856.7(8) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.908 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 1.240 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8673 _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 5742 _diffrn_reflns_av_R_equivalents 0.1647 _diffrn_reflns_av_sigmaI/netI 0.7254 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2872 _reflns_number_gt 519 _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^)+(0.0230P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2872 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.3692 _refine_ls_R_factor_gt 0.0569 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.0649 _refine_ls_goodness_of_fit_ref 0.633 _refine_ls_restrained_S_all 0.633 _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 Ag1 Ag 0.3508(3) 0.4474(2) 0.39499(7) 0.0759(6) Uani 1 1 d . . . O1 O 0.3706(19) -0.3510(14) 0.2585(4) 0.070(4) Uani 1 1 d . . . H1 H 0.3590 -0.4215 0.2187 0.105 Uiso 1 1 calc R . . O2 O 0.3027(14) -0.4574(14) 0.1046(4) 0.059(3) Uani 1 1 d . . . O3 O 0.2822(18) -0.2456(16) 0.0248(5) 0.071(4) Uani 1 1 d . . . H2 H 0.3233 -0.2958 -0.0065 0.107 Uiso 1 1 calc R . . O4 O -0.1355(14) -0.3709(13) 0.2407(4) 0.072(4) Uani 1 1 d . . . H7 H -0.1599 -0.4434 0.1997 0.108 Uiso 1 1 calc R . . O5 O -0.2036(13) -0.4729(13) 0.0877(4) 0.050(3) Uani 1 1 d . . . O6 O -0.2279(19) -0.2593(15) 0.0072(5) 0.077(4) Uani 1 1 d . . . H8 H -0.2044 -0.3224 -0.0259 0.116 Uiso 1 1 calc R . . N1 N 0.5684(15) 0.3329(15) 0.3474(5) 0.049(4) Uani 1 1 d . . . N2 N 0.0042(15) 0.2945(15) 0.3330(5) 0.047(4) Uani 1 1 d . . . N3 N 0.171(3) 0.743(3) 0.4737(10) 0.067(6) Uani 1 1 d . . . O8 O 0.3148(19) 0.720(2) 0.4801(7) 0.084(5) Uani 1 1 d . . . O9 O 0.1649(18) 0.8745(17) 0.5203(6) 0.087(5) Uani 1 1 d . . . O10 O 0.0150(19) 0.645(2) 0.4201(7) 0.091(5) Uani 1 1 d . . . C1 C 0.3633(13) -0.1359(12) 0.1606(4) 0.043(4) Uiso 1 1 d G . . C2 C 0.3949(14) -0.1746(10) 0.2385(6) 0.061(5) Uiso 1 1 d G . . C3 C 0.4550(13) -0.0248(14) 0.3007(4) 0.051(4) Uiso 1 1 d G . . H3 H 0.4762 -0.0507 0.3528 0.062 Uiso 1 1 calc R . . C4 C 0.4835(13) 0.1636(12) 0.2849(4) 0.051(5) Uiso 1 1 d G . . C5 C 0.4519(12) 0.2022(10) 0.2070(5) 0.037(4) Uiso 1 1 d G . . H5 H 0.4709 0.3283 0.1965 0.044 Uiso 1 1 calc R . . C6 C 0.3918(12) 0.0525(14) 0.1449(3) 0.050(4) Uiso 1 1 d G . . H6 H 0.3706 0.0783 0.0928 0.060 Uiso 1 1 calc R . . C7 C 0.317(3) -0.294(3) 0.0985(9) 0.061(6) Uiso 1 1 d . . . C8 C -0.1387(13) -0.1492(12) 0.1444(4) 0.042(4) Uiso 1 1 d G . . C9 C -0.1136(14) -0.1902(10) 0.2224(6) 0.060(5) Uiso 1 1 d G . . C10 C -0.0664(13) -0.0448(14) 0.2847(4) 0.051(4) Uiso 1 1 d G . . H10 H -0.0496 -0.0723 0.3369 0.061 Uiso 1 1 calc R . . C11 C -0.0443(13) 0.1415(12) 0.2691(4) 0.043(4) Uiso 1 1 d G . . C12 C -0.0694(13) 0.1825(10) 0.1912(5) 0.050(4) Uiso 1 1 d G . . H12 H -0.0546 0.3072 0.1808 0.060 Uiso 1 1 calc R . . C13 C -0.1166(12) 0.0372(14) 0.1289(3) 0.051(4) Uiso 1 1 d G . . H13 H -0.1334 0.0646 0.0767 0.062 Uiso 1 1 calc R . . C14 C -0.189(2) -0.308(2) 0.0795(8) 0.040(5) Uiso 1 1 d . . . O7 O 0.2947(13) 0.2791(12) 0.5272(4) 0.050(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0784(14) 0.0871(13) 0.0528(8) -0.0093(7) -0.0047(7) 0.0376(11) O1 0.102(11) 0.053(9) 0.051(6) 0.000(6) -0.022(7) 0.044(9) O2 0.077(10) 0.049(9) 0.051(6) -0.001(5) -0.002(6) 0.035(8) O3 0.102(12) 0.065(9) 0.054(7) -0.005(6) 0.007(7) 0.049(9) O4 0.099(12) 0.064(10) 0.047(6) -0.005(6) -0.003(6) 0.039(9) O5 0.086(10) 0.038(8) 0.034(6) 0.000(5) -0.002(5) 0.039(8) O6 0.135(13) 0.070(10) 0.044(7) -0.007(6) 0.001(7) 0.068(9) N1 0.023(10) 0.067(10) 0.044(7) -0.024(6) -0.006(6) 0.016(9) N2 0.024(10) 0.059(10) 0.043(7) -0.034(6) 0.007(6) 0.011(9) N3 0.06(2) 0.066(17) 0.082(14) 0.027(11) 0.005(13) 0.036(17) O8 0.052(13) 0.113(12) 0.101(9) -0.002(7) -0.007(8) 0.056(11) O9 0.107(13) 0.064(11) 0.107(10) -0.005(7) 0.023(8) 0.056(10) O10 0.025(11) 0.121(13) 0.127(11) -0.006(9) -0.008(8) 0.043(10) O7 0.031(9) 0.054(8) 0.056(6) -0.003(5) 0.000(5) 0.016(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.376(10) . ? Ag1 N1 2.413(9) . ? Ag1 O7 2.625(9) . ? Ag1 O7 2.620(9) 2_666 ? Ag1 O8 2.635(14) . ? O1 C2 1.332(8) . ? O1 H1 0.8200 . ? O2 C7 1.207(13) . ? O3 C7 1.354(14) . ? O3 H2 0.8200 . ? O4 C9 1.361(8) . ? O4 H7 0.8200 . ? O5 C14 1.227(12) . ? O6 C14 1.339(12) . ? O6 H8 0.8200 . ? N1 C4 1.467(10) . ? N2 C11 1.444(9) . ? N3 O8 1.172(15) . ? N3 O9 1.282(16) . ? N3 O10 1.275(17) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.455(15) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.3900 . ? C8 C13 1.3900 . ? C8 C14 1.481(13) . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 C12 1.3900 . ? C12 C13 1.3900 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? O7 Ag1 2.620(9) 2_666 ? 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 N2 Ag1 N1 118.6(3) . . ? N2 Ag1 O7 159.5(2) . 2_666 ? N1 Ag1 O7 79.9(3) . 2_666 ? C2 O1 H1 109.5 . . ? C7 O3 H2 109.5 . . ? C9 O4 H7 109.5 . . ? C14 O6 H8 109.5 . . ? C4 N1 Ag1 120.1(6) . . ? C11 N2 Ag1 112.3(6) . . ? O8 N3 O9 121(2) . . ? O8 N3 O10 124(2) . . ? O9 N3 O10 115.4(17) . . ? C2 C1 C6 120.0 . . ? C2 C1 C7 116.9(10) . . ? C6 C1 C7 122.9(10) . . ? O1 C2 C3 116.4(8) . . ? O1 C2 C1 123.6(8) . . ? C3 C2 C1 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 N1 122.1(7) . . ? C5 C4 N1 117.6(7) . . ? C6 C5 C4 120.0 . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O2 C7 O3 118.3(14) . . ? O2 C7 C1 129.0(15) . . ? O3 C7 C1 112.7(14) . . ? C9 C8 C13 120.0 . . ? C9 C8 C14 118.5(9) . . ? C13 C8 C14 121.5(9) . . ? O4 C9 C8 122.2(8) . . ? O4 C9 C10 117.8(8) . . ? C8 C9 C10 120.0 . . ? C9 C10 C11 120.0 . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 120.0 . . ? C10 C11 N2 120.9(8) . . ? C12 C11 N2 119.1(8) . . ? C13 C12 C11 120.0 . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 120.0 . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.0 . . ? O5 C14 O6 120.4(12) . . ? O5 C14 C8 125.8(12) . . ? O6 C14 C8 113.7(12) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.316 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.084 # Attachment '2-rev.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 723419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H28 Cl2 N4 Ni1 O8' _chemical_formula_weight 485.97 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' Cl Cl 0.1484 0.1585 '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' Ni Ni 0.3393 1.1124 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.6316(7) _cell_length_b 7.3983(5) _cell_length_c 15.8730(14) _cell_angle_alpha 90.00 _cell_angle_beta 113.769(6) _cell_angle_gamma 90.00 _cell_volume 1035.13(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour light_green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 508 _exptl_absorpt_coefficient_mu 1.240 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9238 _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 4466 _diffrn_reflns_av_R_equivalents 0.0759 _diffrn_reflns_av_sigmaI/netI 0.1864 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1817 _reflns_number_gt 955 _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1817 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1543 _refine_ls_R_factor_gt 0.0695 _refine_ls_wR_factor_ref 0.2429 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 0.728 _refine_ls_restrained_S_all 0.728 _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 Ni1 Ni 0.0000 0.0000 0.0000 0.0200(5) Uani 1 2 d S . . O1 O 0.2176(6) 0.0114(9) 0.0979(4) 0.0286(15) Uani 1 1 d . . . H1 H 0.2330 0.0789 0.1445 0.034 Uiso 1 1 d R . . H2 H 0.2440 -0.0861 0.1155 0.034 Uiso 1 1 d R . . O2 O -0.0328(7) -0.1958(9) 0.0844(4) 0.0287(16) Uani 1 1 d . . . O3 O -0.0542(6) -0.7964(8) 0.0678(4) 0.0260(15) Uani 1 1 d . . . N1 N -0.1942(9) -0.3940(12) -0.0163(5) 0.044(2) Uani 1 1 d . . . H10 H -0.2121 -0.3310 -0.0625 0.053 Uiso 1 1 d R . . H11 H -0.2361 -0.4880 -0.0205 0.053 Uiso 1 1 d R . . N2 N -0.1897(8) -0.6170(10) 0.1217(5) 0.0262(19) Uani 1 1 d . . . C1 C -0.1038(9) -0.3407(13) 0.0661(6) 0.024(2) Uani 1 1 d . . . C2 C -0.0852(10) -0.4663(11) 0.1451(6) 0.024(2) Uani 1 1 d . . . H2A H 0.0178 -0.5125 0.1704 0.029 Uiso 1 1 d R . . H2B H -0.0985 -0.3968 0.1931 0.029 Uiso 1 1 d R . . C3 C -0.1660(10) -0.7744(13) 0.0876(6) 0.025(2) Uani 1 1 d . . . C4 C -0.2907(10) -0.9014(14) 0.0787(7) 0.030(2) Uani 1 1 d . . . H4A H -0.2561 -0.9933 0.1263 0.036 Uiso 1 1 d R . . H4B H -0.3292 -0.9600 0.0190 0.036 Uiso 1 1 d R . . C5 C -0.4113(12) -0.7850(15) 0.0897(8) 0.046(3) Uani 1 1 d . . . H5A H -0.4601 -0.8477 0.1241 0.056 Uiso 1 1 d R . . H5B H -0.4877 -0.7514 0.0300 0.056 Uiso 1 1 d R . . C6 C -0.3269(12) -0.6208(14) 0.1403(8) 0.047(3) Uani 1 1 d . . . H6A H -0.3865 -0.5120 0.1174 0.057 Uiso 1 1 d R . . H6B H -0.3018 -0.6322 0.2057 0.057 Uiso 1 1 d R . . O4 O -0.3621(7) -0.6858(9) -0.1467(5) 0.0433(19) Uani 1 1 d . . . H3 H -0.4477 -0.7113 -0.1801 0.052 Uiso 1 1 d R . . H4 H -0.3437 -0.5973 -0.1771 0.052 Uiso 1 1 d R . . Cl1 Cl 0.3087(3) -0.6794(4) 0.24174(16) 0.0376(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ni1 0.0240(8) 0.0087(9) 0.0273(9) -0.0020(8) 0.0101(6) -0.0012(8) O1 0.029(3) 0.021(4) 0.030(3) -0.001(3) 0.006(3) 0.003(3) O2 0.036(4) 0.018(4) 0.031(4) -0.009(3) 0.013(3) -0.013(3) O3 0.022(3) 0.019(4) 0.035(4) -0.005(3) 0.010(3) -0.009(3) N1 0.061(6) 0.028(6) 0.026(4) 0.016(4) -0.002(4) -0.011(5) N2 0.035(4) 0.020(5) 0.038(5) 0.002(4) 0.030(4) 0.000(4) C1 0.023(4) 0.024(6) 0.031(5) -0.004(5) 0.015(4) 0.007(4) C2 0.040(5) 0.013(6) 0.023(5) -0.011(4) 0.017(4) -0.010(4) C3 0.034(5) 0.021(6) 0.019(5) 0.007(4) 0.009(4) -0.005(4) C4 0.034(5) 0.024(6) 0.039(6) -0.006(5) 0.021(4) -0.006(5) C5 0.049(7) 0.032(7) 0.073(8) -0.012(6) 0.040(6) -0.013(6) C6 0.052(6) 0.036(7) 0.072(8) -0.010(7) 0.044(6) -0.005(6) O4 0.040(4) 0.022(4) 0.050(4) 0.002(4) 0.000(3) -0.001(3) Cl1 0.0419(14) 0.0319(16) 0.0327(13) -0.0033(12) 0.0083(10) 0.0036(13) _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 Ni1 O3 2.038(6) 1_565 ? Ni1 O3 2.038(6) 3_545 ? Ni1 O1 2.047(5) . ? Ni1 O1 2.047(5) 3 ? Ni1 O2 2.082(6) . ? Ni1 O2 2.082(6) 3 ? O1 H1 0.8544 . ? O1 H2 0.7783 . ? O2 C1 1.242(11) . ? O3 C3 1.247(10) . ? O3 Ni1 2.038(6) 1_545 ? N1 C1 1.305(11) . ? N1 H10 0.8263 . ? N1 H11 0.7933 . ? N2 C3 1.342(12) . ? N2 C2 1.447(11) . ? N2 C6 1.466(11) . ? C1 C2 1.512(12) . ? C2 H2A 0.9701 . ? C2 H2B 0.9695 . ? C3 C4 1.487(12) . ? C4 C5 1.511(13) . ? C4 H4A 0.9702 . ? C4 H4B 0.9696 . ? C5 C6 1.501(14) . ? C5 H5A 0.9701 . ? C5 H5B 0.9691 . ? C6 H6A 0.9702 . ? C6 H6B 0.9700 . ? O4 H3 0.8025 . ? O4 H4 0.8729 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Ni1 O3 180.0(3) 1_565 3_545 ? O3 Ni1 O1 88.3(2) 1_565 . ? O3 Ni1 O1 91.7(2) 3_545 . ? O3 Ni1 O1 91.7(2) 1_565 3 ? O3 Ni1 O1 88.3(2) 3_545 3 ? O1 Ni1 O1 180.0(5) . 3 ? O3 Ni1 O2 92.1(2) 1_565 . ? O3 Ni1 O2 87.9(2) 3_545 . ? O1 Ni1 O2 85.1(2) . . ? O1 Ni1 O2 94.9(2) 3 . ? O3 Ni1 O2 87.9(2) 1_565 3 ? O3 Ni1 O2 92.1(2) 3_545 3 ? O1 Ni1 O2 94.9(2) . 3 ? O1 Ni1 O2 85.1(2) 3 3 ? O2 Ni1 O2 180.0(4) . 3 ? Ni1 O1 H1 116.7 . . ? Ni1 O1 H2 108.7 . . ? H1 O1 H2 108.3 . . ? C1 O2 Ni1 131.5(6) . . ? C3 O3 Ni1 131.3(6) . 1_545 ? C1 N1 H10 122.3 . . ? C1 N1 H11 117.4 . . ? H10 N1 H11 120.2 . . ? C3 N2 C2 123.9(7) . . ? C3 N2 C6 112.2(8) . . ? C2 N2 C6 123.6(8) . . ? O2 C1 N1 125.3(9) . . ? O2 C1 C2 117.8(8) . . ? N1 C1 C2 117.0(8) . . ? N2 C2 C1 115.0(7) . . ? N2 C2 H2A 108.9 . . ? C1 C2 H2A 108.6 . . ? N2 C2 H2B 108.2 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.4 . . ? O3 C3 N2 121.3(8) . . ? O3 C3 C4 129.8(9) . . ? N2 C3 C4 108.9(8) . . ? C3 C4 C5 104.9(8) . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4A 110.4 . . ? C3 C4 H4B 110.6 . . ? C5 C4 H4B 111.0 . . ? H4A C4 H4B 108.9 . . ? C6 C5 C4 104.3(8) . . ? C6 C5 H5A 111.5 . . ? C4 C5 H5A 111.2 . . ? C6 C5 H5B 110.4 . . ? C4 C5 H5B 110.4 . . ? H5A C5 H5B 108.9 . . ? N2 C6 C5 104.2(8) . . ? N2 C6 H6A 110.8 . . ? C5 C6 H6A 111.1 . . ? N2 C6 H6B 111.1 . . ? C5 C6 H6B 110.4 . . ? H6A C6 H6B 109.1 . . ? H3 O4 H4 101.2 . . ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 0.353 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.090