Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Thomas C. W. Mak' _publ_contact_author_address ; Department of Chemistry The Chinese University of Hong Kong Shatin, New Territories Hong Kong SAR CHINA ; _publ_contact_author_email TCWMAK@CUHK.EDU.HK _publ_section_title ; Single-strand helical complexes constructed from 2-pyridinyl-3-pyridinylmethanone: tuning the helical pitch length by variation of metal cation and/or counter anion ; loop_ _publ_author_name 'T.C.W. Mak' 'Xu-Dong Chen.' data_Compound(1) _database_code_depnum_ccdc_archive 'CCDC 278821' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 Ag N3 O4' _chemical_formula_weight 354.07 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 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 7.9514(6) _cell_length_b 12.1163(9) _cell_length_c 12.4823(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.0770(10) _cell_angle_gamma 90.00 _cell_volume 1149.54(15) _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 Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 1.768 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.653134 _exptl_absorpt_correction_T_max 1.000000 _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 4920 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2035 _reflns_number_gt 1791 _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^)+(0.0486P)^2^+1.4728P] 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 2035 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 -0.05810(5) 0.19116(3) 0.04495(3) 0.05069(17) Uani 1 1 d . . . N1 N 0.1077(4) 0.3358(3) 0.0467(3) 0.0357(7) Uani 1 1 d . A . N2 N 0.1924(4) 0.5345(3) 0.4557(3) 0.0378(8) Uani 1 1 d . . . C1 C 0.1028(6) 0.3849(4) -0.0497(3) 0.0409(9) Uani 1 1 d . . . H1A H 0.0293 0.3554 -0.1157 0.049 Uiso 1 1 calc R A . C2 C 0.2008(6) 0.4769(4) -0.0571(4) 0.0464(11) Uani 1 1 d . A . H2A H 0.1950 0.5076 -0.1263 0.056 Uiso 1 1 calc R . . C3 C 0.3065(6) 0.5221(4) 0.0396(4) 0.0487(11) Uani 1 1 d . . . H3A H 0.3730 0.5847 0.0372 0.058 Uiso 1 1 calc R A . C4 C 0.3132(6) 0.4734(4) 0.1411(4) 0.0443(10) Uani 1 1 d . A . H4A H 0.3833 0.5035 0.2078 0.053 Uiso 1 1 calc R . . C5 C 0.2150(5) 0.3799(3) 0.1421(3) 0.0355(9) Uani 1 1 d . . . C6 C 0.2302(6) 0.3177(3) 0.2488(4) 0.0386(9) Uani 1 1 d . A . C7 C 0.1829(5) 0.4812(3) 0.3599(3) 0.0363(9) Uani 1 1 d . A . H7A H 0.1180 0.5132 0.2928 0.044 Uiso 1 1 calc R . . C8 C 0.2643(5) 0.3814(3) 0.3556(3) 0.0340(8) Uani 1 1 d . . . C9 C 0.3660(5) 0.3359(3) 0.4560(3) 0.0370(9) Uani 1 1 d . A . H9A H 0.4248 0.2695 0.4563 0.044 Uiso 1 1 calc R . . C10 C 0.3785(5) 0.3902(4) 0.5547(3) 0.0397(9) Uani 1 1 d . . . H10A H 0.4461 0.3613 0.6227 0.048 Uiso 1 1 calc R A . C11 C 0.2890(5) 0.4881(4) 0.5508(3) 0.0400(9) Uani 1 1 d . A . H11A H 0.2961 0.5237 0.6181 0.048 Uiso 1 1 calc R . . O1 O 0.2164(5) 0.2184(3) 0.2482(3) 0.0525(8) Uani 1 1 d . A . N3 N -0.2619(5) 0.2865(3) 0.2514(3) 0.0431(9) Uani 1 1 d . . . O2 O -0.285(2) 0.2544(17) 0.1606(13) 0.153(9) Uani 0.50 1 d P A 1 O3 O -0.372(2) 0.2635(17) 0.3011(15) 0.081(5) Uani 0.50 1 d P A 1 O4 O -0.1381(19) 0.3480(11) 0.2958(11) 0.066(4) Uani 0.50 1 d P A 1 O2' O -0.325(2) 0.2915(13) 0.1521(10) 0.138(8) Uani 0.50 1 d P A 2 O3' O -0.313(3) 0.2405(18) 0.3239(19) 0.104(7) Uani 0.50 1 d P A 2 O4' O -0.119(3) 0.322(2) 0.2814(19) 0.169(11) Uani 0.50 1 d P A 2 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 0.0581(3) 0.0416(2) 0.0546(2) -0.00289(15) 0.02018(18) -0.01641(15) N1 0.0422(19) 0.0325(17) 0.0356(17) -0.0045(14) 0.0164(15) -0.0010(14) N2 0.0373(18) 0.0382(18) 0.0372(18) -0.0021(15) 0.0101(14) 0.0016(14) C1 0.048(2) 0.041(2) 0.037(2) -0.0011(18) 0.0183(18) 0.0025(19) C2 0.060(3) 0.043(3) 0.043(2) 0.0059(19) 0.027(2) 0.002(2) C3 0.056(3) 0.039(2) 0.058(3) 0.001(2) 0.029(2) -0.009(2) C4 0.049(3) 0.042(2) 0.043(2) -0.0058(19) 0.0153(19) -0.0101(19) C5 0.038(2) 0.034(2) 0.037(2) -0.0034(17) 0.0147(17) 0.0031(16) C6 0.040(2) 0.039(2) 0.041(2) -0.0015(18) 0.0178(18) -0.0021(17) C7 0.036(2) 0.039(2) 0.0315(19) 0.0041(17) 0.0056(16) 0.0018(17) C8 0.035(2) 0.033(2) 0.0343(19) 0.0001(16) 0.0120(16) -0.0001(16) C9 0.035(2) 0.033(2) 0.044(2) 0.0022(17) 0.0116(17) 0.0013(16) C10 0.036(2) 0.043(2) 0.036(2) 0.0056(18) 0.0051(17) -0.0017(18) C11 0.045(2) 0.042(2) 0.031(2) -0.0048(17) 0.0085(17) -0.0028(19) O1 0.084(2) 0.0324(17) 0.0458(17) -0.0027(13) 0.0259(17) -0.0053(15) N3 0.044(2) 0.037(2) 0.050(2) -0.0033(18) 0.0169(19) 0.0001(17) O2 0.120(11) 0.231(18) 0.149(13) -0.160(14) 0.103(11) -0.094(11) O3 0.069(10) 0.106(12) 0.085(9) -0.013(9) 0.046(8) -0.011(7) O4 0.065(8) 0.073(6) 0.068(6) -0.052(6) 0.031(6) -0.045(6) O2' 0.143(13) 0.144(12) 0.075(8) 0.074(9) -0.048(8) -0.087(9) O3' 0.093(14) 0.101(10) 0.130(12) 0.064(8) 0.050(10) -0.009(9) O4' 0.050(8) 0.29(3) 0.17(2) 0.095(17) 0.020(11) 0.012(12) _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 2.177(3) 2_545 ? Ag1 N1 2.189(3) . ? Ag1 O2 2.728(11) . ? Ag1 O1 2.838(4) . ? N1 C1 1.334(5) . ? N1 C5 1.355(5) . ? N2 C11 1.335(5) . ? N2 C7 1.341(5) . ? N2 Ag1 2.177(3) 2 ? C1 C2 1.379(6) . ? C2 C3 1.366(7) . ? C3 C4 1.384(6) . ? C4 C5 1.379(6) . ? C5 C6 1.503(6) . ? C6 O1 1.209(5) . ? C6 C8 1.495(6) . ? C7 C8 1.380(6) . ? C8 C9 1.390(6) . ? C9 C10 1.374(6) . ? C10 C11 1.377(6) . ? N3 O2 1.161(12) . ? N3 O4' 1.17(2) . ? N3 O2' 1.193(12) . ? N3 O4 1.229(11) . ? N3 O3' 1.23(2) . ? N3 O3 1.246(19) . ? 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 172.49(12) 2_545 . ? N2 Ag1 O2 81.2(4) 2_545 . ? N1 Ag1 O2 105.0(4) . . ? N2 Ag1 O1 110.63(11) 2_545 . ? N1 Ag1 O1 66.12(11) . . ? O2 Ag1 O1 87.0(4) . . ? C1 N1 C5 117.5(4) . . ? C1 N1 Ag1 119.4(3) . . ? C5 N1 Ag1 123.1(3) . . ? C11 N2 C7 117.2(4) . . ? C11 N2 Ag1 121.6(3) . 2 ? C7 N2 Ag1 121.2(3) . 2 ? N1 C1 C2 123.6(4) . . ? C3 C2 C1 118.6(4) . . ? C2 C3 C4 119.1(4) . . ? C5 C4 C3 119.3(4) . . ? N1 C5 C4 121.9(4) . . ? N1 C5 C6 116.5(4) . . ? C4 C5 C6 121.4(4) . . ? O1 C6 C8 120.8(4) . . ? O1 C6 C5 120.7(4) . . ? C8 C6 C5 118.5(3) . . ? N2 C7 C8 123.5(4) . . ? C7 C8 C9 117.9(4) . . ? C7 C8 C6 121.5(4) . . ? C9 C8 C6 120.3(4) . . ? C10 C9 C8 119.2(4) . . ? C9 C10 C11 118.7(4) . . ? N2 C11 C10 123.4(4) . . ? C6 O1 Ag1 99.5(3) . . ? O2 N3 O4' 107.2(14) . . ? O2 N3 O2' 26.7(15) . . ? O4' N3 O2' 112.8(14) . . ? O2 N3 O4 121.2(10) . . ? O4' N3 O4 19.5(16) . . ? O2' N3 O4 118.3(10) . . ? O2 N3 O3' 125.2(16) . . ? O4' N3 O3' 115.6(16) . . ? O2' N3 O3' 131.1(14) . . ? O4 N3 O3' 109.7(14) . . ? O2 N3 O3 118.7(12) . . ? O4' N3 O3 133.0(15) . . ? O2' N3 O3 112.7(12) . . ? O4 N3 O3 119.9(11) . . ? O3' N3 O3 25.5(13) . . ? N3 O2 Ag1 132.3(11) . . ? 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 N2 Ag1 N1 C1 97.8(9) 2_545 . . . ? O2 Ag1 N1 C1 -116.6(6) . . . . ? O1 Ag1 N1 C1 163.6(3) . . . . ? N2 Ag1 N1 C5 -83.2(10) 2_545 . . . ? O2 Ag1 N1 C5 62.4(6) . . . . ? O1 Ag1 N1 C5 -17.4(3) . . . . ? C5 N1 C1 C2 0.2(6) . . . . ? Ag1 N1 C1 C2 179.3(3) . . . . ? N1 C1 C2 C3 -1.3(7) . . . . ? C1 C2 C3 C4 0.7(7) . . . . ? C2 C3 C4 C5 0.8(7) . . . . ? C1 N1 C5 C4 1.4(6) . . . . ? Ag1 N1 C5 C4 -177.6(3) . . . . ? C1 N1 C5 C6 -174.9(4) . . . . ? Ag1 N1 C5 C6 6.0(5) . . . . ? C3 C4 C5 N1 -1.9(7) . . . . ? C3 C4 C5 C6 174.2(4) . . . . ? N1 C5 C6 O1 31.1(6) . . . . ? C4 C5 C6 O1 -145.3(4) . . . . ? N1 C5 C6 C8 -149.4(4) . . . . ? C4 C5 C6 C8 34.2(6) . . . . ? C11 N2 C7 C8 1.2(6) . . . . ? Ag1 N2 C7 C8 -179.5(3) 2 . . . ? N2 C7 C8 C9 -2.1(6) . . . . ? N2 C7 C8 C6 171.5(4) . . . . ? O1 C6 C8 C7 -140.2(4) . . . . ? C5 C6 C8 C7 40.3(6) . . . . ? O1 C6 C8 C9 33.3(6) . . . . ? C5 C6 C8 C9 -146.2(4) . . . . ? C7 C8 C9 C10 1.4(6) . . . . ? C6 C8 C9 C10 -172.4(4) . . . . ? C8 C9 C10 C11 0.2(6) . . . . ? C7 N2 C11 C10 0.5(6) . . . . ? Ag1 N2 C11 C10 -178.8(3) 2 . . . ? C9 C10 C11 N2 -1.2(6) . . . . ? C8 C6 O1 Ag1 141.5(3) . . . . ? C5 C6 O1 Ag1 -39.1(4) . . . . ? N2 Ag1 O1 C6 -157.6(3) 2_545 . . . ? N1 Ag1 O1 C6 29.7(3) . . . . ? O2 Ag1 O1 C6 -78.2(5) . . . . ? O4' N3 O2 Ag1 22(2) . . . . ? O2' N3 O2 Ag1 129(4) . . . . ? O4 N3 O2 Ag1 37(3) . . . . ? O3' N3 O2 Ag1 -118.5(17) . . . . ? O3 N3 O2 Ag1 -147.6(15) . . . . ? N2 Ag1 O2 N3 117(2) 2_545 . . . ? N1 Ag1 O2 N3 -59(2) . . . . ? O1 Ag1 O2 N3 5.8(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.764 _refine_diff_density_min -0.563 _refine_diff_density_rms 0.089 #===END data_Compound(2) _database_code_depnum_ccdc_archive 'CCDC 278822' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 Ag F6 N2 O P' _chemical_formula_weight 437.03 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' F F 0.0171 0.0103 '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' Ag Ag -0.8971 1.1015 '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 8.6733(7) _cell_length_b 12.1933(10) _cell_length_c 13.2700(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.673(2) _cell_angle_gamma 90.00 _cell_volume 1374.36(19) _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 Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.112 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.654 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.452875 _exptl_absorpt_correction_T_max 1.000000 _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 7267 _diffrn_reflns_av_R_equivalents 0.0510 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2422 _reflns_number_gt 1895 _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^)+(0.0691P)^2^+3.7186P] 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 2422 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1399 _refine_ls_wR_factor_gt 0.1257 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 -0.04053(7) 0.16595(4) 0.06228(4) 0.0439(2) Uani 1 1 d . . . N1 N 0.0881(6) 0.3165(4) 0.0506(4) 0.0325(12) Uani 1 1 d . . . N2 N 0.1705(7) 0.5155(4) 0.4328(4) 0.0372(12) Uani 1 1 d . . . O1 O 0.1762(6) 0.2035(4) 0.2354(4) 0.0453(12) Uani 1 1 d . . . C1 C 0.0857(9) 0.3634(6) -0.0412(5) 0.0413(16) Uani 1 1 d . . . H1A H 0.0217 0.3328 -0.0991 0.050 Uiso 1 1 calc R . . C2 C 0.1741(9) 0.4552(6) -0.0541(5) 0.0502(18) Uani 1 1 d . . . H2A H 0.1712 0.4846 -0.1191 0.060 Uiso 1 1 calc R . . C3 C 0.2659(9) 0.5018(6) 0.0318(5) 0.0454(17) Uani 1 1 d . . . H3A H 0.3267 0.5633 0.0256 0.054 Uiso 1 1 calc R . . C4 C 0.2673(8) 0.4568(5) 0.1267(5) 0.0385(15) Uani 1 1 d . . . H4A H 0.3254 0.4893 0.1858 0.046 Uiso 1 1 calc R . . C5 C 0.1817(7) 0.3629(5) 0.1336(5) 0.0315(13) Uani 1 1 d . . . C6 C 0.1949(8) 0.3019(5) 0.2339(5) 0.0343(14) Uani 1 1 d . . . C7 C 0.1543(8) 0.4612(5) 0.3443(5) 0.0355(14) Uani 1 1 d . . . H7A H 0.0870 0.4900 0.2869 0.043 Uiso 1 1 calc R . . C8 C 0.2312(8) 0.3651(5) 0.3329(4) 0.0323(14) Uani 1 1 d . . . C9 C 0.3373(8) 0.3247(5) 0.4173(5) 0.0401(16) Uani 1 1 d . . . H9A H 0.3928 0.2603 0.4123 0.048 Uiso 1 1 calc R . . C10 C 0.3584(9) 0.3810(6) 0.5077(5) 0.0457(17) Uani 1 1 d . . . H10A H 0.4301 0.3561 0.5649 0.055 Uiso 1 1 calc R . . C11 C 0.2730(8) 0.4752(6) 0.5135(5) 0.0445(17) Uani 1 1 d . . . H11A H 0.2871 0.5122 0.5760 0.053 Uiso 1 1 calc R . . P1 P -0.3034(2) 0.28976(16) 0.24672(14) 0.0444(5) Uani 1 1 d . . . F1 F -0.3424(9) 0.2963(5) 0.1260(4) 0.0972(19) Uani 1 1 d . A . F2 F -0.1500(9) 0.3544(7) 0.2527(9) 0.161(4) Uani 1 1 d . A . F3 F -0.407(3) 0.385(3) 0.255(3) 0.128(14) Uani 0.50 1 d P A 1 F4 F -0.443(3) 0.205(3) 0.2381(15) 0.143(13) Uani 0.50 1 d P A 1 F5 F -0.183(4) 0.189(2) 0.2450(17) 0.102(10) Uani 0.50 1 d P A 1 F3' F -0.360(4) 0.413(3) 0.255(3) 0.148(15) Uani 0.50 1 d P A 2 F4' F -0.463(3) 0.248(4) 0.249(2) 0.173(17) Uani 0.50 1 d P A 2 F5' F -0.239(4) 0.1748(18) 0.242(3) 0.116(14) Uani 0.50 1 d P A 2 F6 F -0.2649(8) 0.2781(6) 0.3686(4) 0.104(2) Uani 1 1 d . A . 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 0.0624(4) 0.0390(3) 0.0317(3) -0.0022(2) 0.0127(2) -0.0112(2) N1 0.046(3) 0.030(3) 0.022(3) 0.000(2) 0.009(2) 0.000(2) N2 0.052(3) 0.036(3) 0.023(3) 0.002(2) 0.006(2) 0.003(2) O1 0.070(3) 0.034(2) 0.029(2) 0.000(2) 0.005(2) -0.004(2) C1 0.055(4) 0.045(4) 0.023(3) -0.004(3) 0.006(3) 0.005(3) C2 0.076(5) 0.052(4) 0.025(4) 0.012(3) 0.016(3) 0.003(4) C3 0.060(5) 0.037(3) 0.042(4) 0.005(3) 0.017(3) -0.003(3) C4 0.049(4) 0.039(3) 0.029(3) 0.000(3) 0.011(3) 0.000(3) C5 0.039(3) 0.034(3) 0.022(3) 0.000(2) 0.007(3) 0.005(3) C6 0.042(4) 0.033(3) 0.026(3) 0.002(3) 0.003(3) 0.003(3) C7 0.049(4) 0.034(3) 0.021(3) 0.003(3) 0.000(3) 0.003(3) C8 0.045(4) 0.034(3) 0.017(3) 0.005(2) 0.003(3) -0.002(3) C9 0.047(4) 0.038(3) 0.034(4) 0.010(3) 0.007(3) 0.009(3) C10 0.051(4) 0.051(4) 0.029(4) 0.009(3) -0.004(3) 0.002(3) C11 0.057(4) 0.048(4) 0.025(3) 0.000(3) 0.001(3) 0.003(3) P1 0.0464(10) 0.0503(10) 0.0357(10) -0.0094(8) 0.0062(8) -0.0001(9) F1 0.148(6) 0.108(4) 0.036(3) 0.005(3) 0.019(3) -0.014(4) F2 0.088(5) 0.136(7) 0.245(11) 0.055(7) -0.004(6) -0.052(5) F3 0.096(12) 0.14(3) 0.120(17) -0.049(17) -0.048(10) 0.092(16) F4 0.18(3) 0.19(2) 0.045(8) -0.013(10) -0.007(11) -0.15(2) F5 0.137(19) 0.12(2) 0.048(9) -0.009(9) 0.029(9) 0.064(15) F3' 0.28(4) 0.061(9) 0.075(13) -0.028(8) -0.032(18) 0.070(17) F4' 0.070(12) 0.33(5) 0.14(2) -0.06(2) 0.075(13) -0.072(17) F5' 0.20(4) 0.029(6) 0.15(2) 0.004(8) 0.088(19) 0.012(11) F6 0.148(5) 0.116(5) 0.033(3) -0.021(3) -0.017(3) 0.033(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.160(5) 2_545 ? Ag1 N1 2.170(5) . ? Ag1 O1 2.697(5) . ? Ag1 C7 3.040(6) 2_545 ? N1 C1 1.342(8) . ? N1 C5 1.354(8) . ? N2 C7 1.332(8) . ? N2 C11 1.340(8) . ? N2 Ag1 2.160(5) 2 ? O1 C6 1.212(8) . ? C1 C2 1.386(10) . ? C2 C3 1.374(10) . ? C3 C4 1.372(9) . ? C4 C5 1.378(9) . ? C5 C6 1.509(9) . ? C6 C8 1.499(9) . ? C7 C8 1.372(9) . ? C7 Ag1 3.040(6) 2 ? C8 C9 1.389(9) . ? C9 C10 1.362(10) . ? C10 C11 1.377(10) . ? P1 F3 1.48(2) . ? P1 F4' 1.48(2) . ? P1 F5' 1.51(2) . ? P1 F2 1.534(7) . ? P1 F1 1.571(5) . ? P1 F4 1.58(2) . ? P1 F6 1.590(5) . ? P1 F3' 1.60(3) . ? P1 F5 1.61(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Ag1 N1 177.67(19) 2_545 . ? N2 Ag1 O1 113.34(17) 2_545 . ? N1 Ag1 O1 68.76(16) . . ? N2 Ag1 C7 22.50(17) 2_545 2_545 ? N1 Ag1 C7 159.73(17) . 2_545 ? O1 Ag1 C7 91.12(15) . 2_545 ? C1 N1 C5 117.2(5) . . ? C1 N1 Ag1 120.8(4) . . ? C5 N1 Ag1 121.9(4) . . ? C7 N2 C11 117.2(6) . . ? C7 N2 Ag1 119.1(4) . 2 ? C11 N2 Ag1 123.6(4) . 2 ? C6 O1 Ag1 103.1(4) . . ? N1 C1 C2 123.3(6) . . ? C3 C2 C1 118.3(6) . . ? C4 C3 C2 119.5(7) . . ? C3 C4 C5 119.3(6) . . ? N1 C5 C4 122.4(6) . . ? N1 C5 C6 116.0(5) . . ? C4 C5 C6 121.5(6) . . ? O1 C6 C8 120.0(6) . . ? O1 C6 C5 121.1(6) . . ? C8 C6 C5 119.0(5) . . ? N2 C7 C8 123.8(5) . . ? N2 C7 Ag1 38.4(3) . 2 ? C8 C7 Ag1 162.2(4) . 2 ? C7 C8 C9 118.1(6) . . ? C7 C8 C6 121.0(5) . . ? C9 C8 C6 120.8(6) . . ? C10 C9 C8 118.7(6) . . ? C9 C10 C11 119.5(6) . . ? N2 C11 C10 122.6(6) . . ? F3 P1 F4' 72(2) . . ? F3 P1 F5' 163(2) . . ? F4' P1 F5' 92(2) . . ? F3 P1 F2 97.4(15) . . ? F4' P1 F2 168.5(16) . . ? F5' P1 F2 99.0(14) . . ? F3 P1 F1 91.8(14) . . ? F4' P1 F1 91.8(12) . . ? F5' P1 F1 90.7(13) . . ? F2 P1 F1 91.8(5) . . ? F3 P1 F4 92.8(19) . . ? F4' P1 F4 22(2) . . ? F5' P1 F4 71(2) . . ? F2 P1 F4 169.8(14) . . ? F1 P1 F4 87.5(8) . . ? F3 P1 F6 89.7(14) . . ? F4' P1 F6 87.2(13) . . ? F5' P1 F6 87.3(13) . . ? F2 P1 F6 89.6(5) . . ? F1 P1 F6 177.8(4) . . ? F4 P1 F6 90.8(8) . . ? F3 P1 F3' 20(3) . . ? F4' P1 F3' 91(2) . . ? F5' P1 F3' 176(2) . . ? F2 P1 F3' 77.8(16) . . ? F1 P1 F3' 90.7(13) . . ? F4 P1 F3' 112(2) . . ? F6 P1 F3' 91.3(13) . . ? F3 P1 F5 175.9(15) . . ? F4' P1 F5 110(2) . . ? F5' P1 F5 18(2) . . ? F2 P1 F5 80.5(13) . . ? F1 P1 F5 91.8(8) . . ? F4 P1 F5 89.3(17) . . ? F6 P1 F5 86.7(8) . . ? F3' P1 F5 158.2(19) . . ? 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 N2 Ag1 N1 C1 9(5) 2_545 . . . ? O1 Ag1 N1 C1 163.2(5) . . . . ? C7 Ag1 N1 C1 170.5(5) 2_545 . . . ? N2 Ag1 N1 C5 -167(5) 2_545 . . . ? O1 Ag1 N1 C5 -12.4(4) . . . . ? C7 Ag1 N1 C5 -5.0(8) 2_545 . . . ? N2 Ag1 O1 C6 -157.1(4) 2_545 . . . ? N1 Ag1 O1 C6 24.0(4) . . . . ? C7 Ag1 O1 C6 -153.5(5) 2_545 . . . ? C5 N1 C1 C2 0.3(10) . . . . ? Ag1 N1 C1 C2 -175.4(5) . . . . ? N1 C1 C2 C3 -1.4(11) . . . . ? C1 C2 C3 C4 -0.2(11) . . . . ? C2 C3 C4 C5 2.8(11) . . . . ? C1 N1 C5 C4 2.5(9) . . . . ? Ag1 N1 C5 C4 178.2(5) . . . . ? C1 N1 C5 C6 -174.0(6) . . . . ? Ag1 N1 C5 C6 1.7(7) . . . . ? C3 C4 C5 N1 -4.1(10) . . . . ? C3 C4 C5 C6 172.2(6) . . . . ? Ag1 O1 C6 C8 146.9(5) . . . . ? Ag1 O1 C6 C5 -33.0(7) . . . . ? N1 C5 C6 O1 26.9(9) . . . . ? C4 C5 C6 O1 -149.6(7) . . . . ? N1 C5 C6 C8 -153.0(6) . . . . ? C4 C5 C6 C8 30.5(9) . . . . ? C11 N2 C7 C8 2.8(10) . . . . ? Ag1 N2 C7 C8 -180.0(5) 2 . . . ? C11 N2 C7 Ag1 -177.2(9) . . . 2 ? N2 C7 C8 C9 -3.0(10) . . . . ? Ag1 C7 C8 C9 -3.0(19) 2 . . . ? N2 C7 C8 C6 173.5(6) . . . . ? Ag1 C7 C8 C6 173.4(12) 2 . . . ? O1 C6 C8 C7 -134.2(7) . . . . ? C5 C6 C8 C7 45.6(9) . . . . ? O1 C6 C8 C9 42.2(10) . . . . ? C5 C6 C8 C9 -138.0(6) . . . . ? C7 C8 C9 C10 1.0(10) . . . . ? C6 C8 C9 C10 -175.5(6) . . . . ? C8 C9 C10 C11 1.0(11) . . . . ? C7 N2 C11 C10 -0.7(10) . . . . ? Ag1 N2 C11 C10 -177.8(5) 2 . . . ? C9 C10 C11 N2 -1.2(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.121 _refine_diff_density_min -0.655 _refine_diff_density_rms 0.140 #===END data_Compound(3) _database_code_depnum_ccdc_archive 'CCDC 278823' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 Ag B F4 N2 O' _chemical_formula_weight 378.87 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 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 8.0172(5) _cell_length_b 12.4067(8) _cell_length_c 13.2083(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.3550(10) _cell_angle_gamma 90.00 _cell_volume 1231.75(14) _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 Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.043 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 1.681 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.375764 _exptl_absorpt_correction_T_max 1.000000 _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 6505 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0249 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2165 _reflns_number_gt 1909 _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^)+(0.0565P)^2^+1.4207P] 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 2165 _refine_ls_number_parameters 217 _refine_ls_number_restraints 56 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0988 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.131 _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 0.34498(5) -0.07805(3) 0.05843(3) 0.04891(17) Uani 1 1 d . . . N1 N 0.1984(5) 0.0718(3) 0.0457(3) 0.0376(8) Uani 1 1 d . . . N2 N 0.5138(5) 0.2743(3) 0.4409(3) 0.0383(7) Uani 1 1 d . . . O1 O 0.2819(5) -0.0347(2) 0.2416(2) 0.0483(8) Uani 1 1 d . . . C1 C 0.1110(6) 0.1163(4) -0.0510(3) 0.0431(10) Uani 1 1 d . . . H1A H 0.1177 0.0831 -0.1126 0.052 Uiso 1 1 calc R . . C2 C 0.0117(6) 0.2093(4) -0.0625(4) 0.0473(11) Uani 1 1 d . . . H2A H -0.0489 0.2371 -0.1309 0.057 Uiso 1 1 calc R . . C3 C 0.0031(6) 0.2605(4) 0.0277(4) 0.0493(11) Uani 1 1 d . . . H3A H -0.0615 0.3239 0.0217 0.059 Uiso 1 1 calc R . . C4 C 0.0929(6) 0.2154(4) 0.1279(3) 0.0422(9) Uani 1 1 d . . . H4A H 0.0891 0.2482 0.1903 0.051 Uiso 1 1 calc R . . C5 C 0.1878(5) 0.1216(3) 0.1344(3) 0.0344(8) Uani 1 1 d . . . C6 C 0.2711(5) 0.0628(3) 0.2398(3) 0.0361(9) Uani 1 1 d . . . C7 C 0.4312(5) 0.2225(3) 0.3479(3) 0.0364(9) Uani 1 1 d . . . H7A H 0.4347 0.2525 0.2841 0.044 Uiso 1 1 calc R . . C8 C 0.3407(5) 0.1261(3) 0.3426(3) 0.0340(8) Uani 1 1 d . . . C9 C 0.3295(6) 0.0837(3) 0.4370(3) 0.0383(9) Uani 1 1 d . . . H9A H 0.2678 0.0200 0.4358 0.046 Uiso 1 1 calc R . . C10 C 0.4120(6) 0.1380(3) 0.5335(3) 0.0420(10) Uani 1 1 d . . . H10A H 0.4049 0.1118 0.5979 0.050 Uiso 1 1 calc R . . C11 C 0.5042(6) 0.2308(4) 0.5322(3) 0.0414(9) Uani 1 1 d . . . H11A H 0.5628 0.2653 0.5974 0.050 Uiso 1 1 calc R . . B1 B 0.2248(6) 0.5386(3) 0.2249(3) 0.0467(12) Uani 1 1 d D . . F1 F 0.2585(18) 0.5759(12) 0.1413(10) 0.168(10) Uani 0.50 1 d PD A 1 F2 F 0.3420(16) 0.4674(14) 0.2770(14) 0.176(10) Uani 0.50 1 d PD A 1 F3 F 0.0645(13) 0.4905(14) 0.1926(12) 0.171(6) Uani 0.50 1 d PD A 1 F4 F 0.213(3) 0.6204(11) 0.2855(13) 0.257(13) Uani 0.50 1 d PD A 1 F1' F 0.2219(18) 0.5570(8) 0.1243(5) 0.114(6) Uani 0.50 1 d PD A 2 F2' F 0.2493(19) 0.4343(5) 0.2416(9) 0.097(4) Uani 0.50 1 d PD A 2 F3' F 0.0865(11) 0.5737(9) 0.2436(9) 0.099(3) Uani 0.50 1 d PD A 2 F4' F 0.3700(12) 0.5855(12) 0.2923(10) 0.161(6) Uani 0.50 1 d PD A 2 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 0.0579(3) 0.0377(2) 0.0481(2) -0.00308(14) 0.01468(18) 0.01053(14) N1 0.0426(19) 0.0338(18) 0.0345(18) -0.0002(13) 0.0110(15) -0.0013(14) N2 0.0447(19) 0.0331(18) 0.0374(18) 0.0023(14) 0.0146(15) 0.0003(15) O1 0.068(2) 0.0313(17) 0.0401(16) 0.0029(12) 0.0113(15) 0.0029(14) C1 0.049(2) 0.043(2) 0.034(2) 0.0009(18) 0.0111(19) -0.006(2) C2 0.049(3) 0.046(3) 0.037(2) 0.0135(19) 0.0032(19) -0.002(2) C3 0.049(2) 0.038(2) 0.058(3) 0.007(2) 0.014(2) 0.010(2) C4 0.044(2) 0.042(2) 0.041(2) 0.0000(18) 0.0136(18) 0.0033(18) C5 0.036(2) 0.031(2) 0.036(2) 0.0016(16) 0.0121(16) -0.0031(16) C6 0.038(2) 0.035(2) 0.034(2) 0.0016(16) 0.0121(17) -0.0004(16) C7 0.044(2) 0.034(2) 0.0314(19) 0.0055(16) 0.0140(17) 0.0035(17) C8 0.039(2) 0.029(2) 0.034(2) 0.0022(16) 0.0124(17) 0.0046(16) C9 0.044(2) 0.033(2) 0.041(2) 0.0072(16) 0.0178(19) 0.0027(16) C10 0.056(3) 0.040(2) 0.033(2) 0.0094(17) 0.0198(19) 0.0066(19) C11 0.048(2) 0.043(2) 0.030(2) 0.0006(17) 0.0097(18) 0.0052(19) B1 0.047(3) 0.042(3) 0.049(3) 0.005(2) 0.014(2) 0.002(2) F1 0.097(8) 0.179(14) 0.27(2) 0.161(14) 0.119(12) 0.044(8) F2 0.095(9) 0.26(2) 0.172(14) 0.140(15) 0.039(9) 0.106(12) F3 0.099(9) 0.238(18) 0.154(12) -0.029(12) 0.017(8) -0.053(11) F4 0.29(3) 0.207(17) 0.214(18) -0.151(15) 0.012(18) 0.075(18) F1' 0.195(14) 0.112(8) 0.041(4) 0.026(5) 0.048(5) 0.085(8) F2' 0.190(13) 0.031(3) 0.099(7) 0.014(4) 0.085(8) 0.023(5) F3' 0.069(5) 0.142(9) 0.114(7) 0.039(6) 0.067(5) 0.054(5) F4' 0.097(8) 0.161(12) 0.205(14) -0.131(11) 0.026(8) -0.030(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 2.152(3) 2_645 ? Ag1 N1 2.174(3) . ? N1 C1 1.343(6) . ? N1 C5 1.353(5) . ? N2 C7 1.339(5) . ? N2 C11 1.348(5) . ? N2 Ag1 2.152(3) 2_655 ? O1 C6 1.212(5) . ? C1 C2 1.380(7) . ? C2 C3 1.374(7) . ? C3 C4 1.385(6) . ? C4 C5 1.377(6) . ? C5 C6 1.507(6) . ? C6 C8 1.499(6) . ? C7 C8 1.388(6) . ? C8 C9 1.385(6) . ? C9 C10 1.389(6) . ? C10 C11 1.372(6) . ? B1 F3' 1.293(6) . ? B1 F2 1.299(7) . ? B1 F1 1.309(7) . ? B1 F2' 1.316(6) . ? B1 F4 1.316(7) . ? B1 F4' 1.329(6) . ? B1 F1' 1.340(6) . ? B1 F3 1.344(7) . ? 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 176.01(13) 2_645 . ? C1 N1 C5 117.8(4) . . ? C1 N1 Ag1 120.9(3) . . ? C5 N1 Ag1 121.2(3) . . ? C7 N2 C11 117.7(4) . . ? C7 N2 Ag1 120.2(3) . 2_655 ? C11 N2 Ag1 122.1(3) . 2_655 ? N1 C1 C2 122.6(4) . . ? C3 C2 C1 119.5(4) . . ? C2 C3 C4 118.4(4) . . ? C5 C4 C3 119.6(4) . . ? N1 C5 C4 122.1(4) . . ? N1 C5 C6 116.0(3) . . ? C4 C5 C6 121.7(4) . . ? O1 C6 C8 120.3(4) . . ? O1 C6 C5 120.5(4) . . ? C8 C6 C5 119.3(3) . . ? N2 C7 C8 122.9(4) . . ? C9 C8 C7 118.6(4) . . ? C9 C8 C6 119.8(4) . . ? C7 C8 C6 121.4(3) . . ? C8 C9 C10 118.9(4) . . ? C11 C10 C9 118.8(4) . . ? N2 C11 C10 123.1(4) . . ? F3' B1 F2 129.7(8) . . ? F3' B1 F1 119.0(7) . . ? F2 B1 F1 111.3(7) . . ? F3' B1 F2' 112.8(6) . . ? F2 B1 F2' 37.3(8) . . ? F1 B1 F2' 115.2(9) . . ? F3' B1 F4 51.5(8) . . ? F2 B1 F4 113.2(13) . . ? F1 B1 F4 108.6(7) . . ? F2' B1 F4 134.0(10) . . ? F3' B1 F4' 109.5(6) . . ? F2 B1 F4' 68.8(10) . . ? F1 B1 F4' 91.2(10) . . ? F2' B1 F4' 105.9(9) . . ? F4 B1 F4' 59.0(8) . . ? F3' B1 F1' 114.3(7) . . ? F2 B1 F1' 113.6(10) . . ? F1 B1 F1' 16.5(10) . . ? F2' B1 F1' 106.5(5) . . ? F4 B1 F1' 119.4(10) . . ? F4' B1 F1' 107.4(6) . . ? F3' B1 F3 54.6(7) . . ? F2 B1 F3 107.6(7) . . ? F1 B1 F3 110.1(9) . . ? F2' B1 F3 71.8(8) . . ? F4 B1 F3 105.8(7) . . ? F4' B1 F3 157.6(9) . . ? F1' B1 F3 94.3(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 N2 Ag1 N1 C1 6(2) 2_645 . . . ? N2 Ag1 N1 C5 -175.6(17) 2_645 . . . ? C5 N1 C1 C2 -0.3(6) . . . . ? Ag1 N1 C1 C2 177.8(3) . . . . ? N1 C1 C2 C3 1.2(7) . . . . ? C1 C2 C3 C4 -1.1(7) . . . . ? C2 C3 C4 C5 0.2(7) . . . . ? C1 N1 C5 C4 -0.6(6) . . . . ? Ag1 N1 C5 C4 -178.7(3) . . . . ? C1 N1 C5 C6 173.7(4) . . . . ? Ag1 N1 C5 C6 -4.5(5) . . . . ? C3 C4 C5 N1 0.7(6) . . . . ? C3 C4 C5 C6 -173.2(4) . . . . ? N1 C5 C6 O1 -27.7(6) . . . . ? C4 C5 C6 O1 146.6(4) . . . . ? N1 C5 C6 C8 152.3(4) . . . . ? C4 C5 C6 C8 -33.4(6) . . . . ? C11 N2 C7 C8 -1.3(6) . . . . ? Ag1 N2 C7 C8 178.8(3) 2_655 . . . ? N2 C7 C8 C9 2.5(6) . . . . ? N2 C7 C8 C6 -171.6(4) . . . . ? O1 C6 C8 C9 -34.2(6) . . . . ? C5 C6 C8 C9 145.9(4) . . . . ? O1 C6 C8 C7 139.9(4) . . . . ? C5 C6 C8 C7 -40.1(5) . . . . ? C7 C8 C9 C10 -1.3(6) . . . . ? C6 C8 C9 C10 173.0(4) . . . . ? C8 C9 C10 C11 -1.0(6) . . . . ? C7 N2 C11 C10 -1.1(6) . . . . ? Ag1 N2 C11 C10 178.7(3) 2_655 . . . ? C9 C10 C11 N2 2.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.801 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.090 #===END data_Compound(4) _database_code_depnum_ccdc_archive 'CCDC 278824' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 Ag Cl N2 O5' _chemical_formula_weight 391.51 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' Cl Cl 0.1484 0.1585 '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 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 8.1126(9) _cell_length_b 12.5127(13) _cell_length_c 13.4177(17) _cell_angle_alpha 90.00 _cell_angle_beta 111.047(2) _cell_angle_gamma 90.00 _cell_volume 1271.2(3) _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 Block _exptl_crystal_colour Light-yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.046 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 1.816 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.785705 _exptl_absorpt_correction_T_max 1.000000 _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 6706 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2241 _reflns_number_gt 1834 _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^)+(0.0633P)^2^+4.6551P] 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 2241 _refine_ls_number_parameters 217 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1453 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_restrained_S_all 1.211 _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 0.34785(9) -0.07870(5) 0.06310(5) 0.0551(3) Uani 1 1 d . . . N1 N 0.2002(8) 0.0696(5) 0.0493(5) 0.0419(14) Uani 1 1 d . . . N2 N 0.5134(8) 0.2740(5) 0.4386(5) 0.0409(13) Uani 1 1 d . . . O1 O 0.2847(8) -0.0340(4) 0.2446(4) 0.0532(13) Uani 1 1 d . . . C1 C 0.1119(11) 0.1136(7) -0.0458(6) 0.0506(19) Uani 1 1 d . . . H1A H 0.1170 0.0802 -0.1066 0.061 Uiso 1 1 calc R . . C2 C 0.0149(11) 0.2047(7) -0.0583(6) 0.0512(19) Uani 1 1 d . . . H2A H -0.0463 0.2315 -0.1262 0.061 Uiso 1 1 calc R . . C3 C 0.0081(11) 0.2558(7) 0.0285(7) 0.056(2) Uani 1 1 d . . . H3A H -0.0550 0.3191 0.0216 0.068 Uiso 1 1 calc R . . C4 C 0.0964(10) 0.2123(6) 0.1275(6) 0.0448(17) Uani 1 1 d . . . H4A H 0.0919 0.2454 0.1885 0.054 Uiso 1 1 calc R . . C5 C 0.1904(9) 0.1204(6) 0.1356(6) 0.0389(15) Uani 1 1 d . . . C6 C 0.2736(9) 0.0633(6) 0.2418(6) 0.0400(16) Uani 1 1 d . . . C7 C 0.4303(10) 0.2218(5) 0.3473(6) 0.0406(16) Uani 1 1 d . . . H7A H 0.4315 0.2511 0.2839 0.049 Uiso 1 1 calc R . . C8 C 0.3428(9) 0.1263(5) 0.3431(5) 0.0371(15) Uani 1 1 d . . . C9 C 0.3335(10) 0.0859(6) 0.4361(6) 0.0469(18) Uani 1 1 d . . . H9A H 0.2720 0.0229 0.4349 0.056 Uiso 1 1 calc R . . C10 C 0.4154(11) 0.1388(6) 0.5311(7) 0.0506(19) Uani 1 1 d . . . H10A H 0.4100 0.1128 0.5948 0.061 Uiso 1 1 calc R . . C11 C 0.5072(10) 0.2334(6) 0.5286(6) 0.0475(18) Uani 1 1 d . . . H11A H 0.5659 0.2689 0.5924 0.057 Uiso 1 1 calc R . . Cl1 Cl 0.2236(2) 0.53880(15) 0.22689(16) 0.0485(5) Uani 1 1 d D . . O2 O 0.221(4) 0.5589(17) 0.1245(11) 0.143(14) Uani 0.50 1 d PD A 1 O3 O 0.239(5) 0.4301(7) 0.241(2) 0.132(12) Uani 0.50 1 d PD A 1 O4 O 0.082(2) 0.5804(17) 0.244(2) 0.113(8) Uani 0.50 1 d PD A 1 O5 O 0.3788(19) 0.576(2) 0.3016(19) 0.217(18) Uani 0.50 1 d PD A 1 O2' O 0.268(4) 0.579(2) 0.146(2) 0.24(3) Uani 0.50 1 d PD A 2 O3' O 0.340(3) 0.457(2) 0.269(3) 0.20(2) Uani 0.50 1 d PD A 2 O4' O 0.060(2) 0.490(2) 0.196(2) 0.166(11) Uani 0.50 1 d PD A 2 O5' O 0.203(5) 0.6270(19) 0.282(3) 0.26(2) Uani 0.50 1 d PD A 2 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 0.0583(4) 0.0417(4) 0.0608(4) -0.0027(3) 0.0158(3) 0.0110(3) N1 0.039(3) 0.041(3) 0.040(3) -0.001(3) 0.007(3) -0.001(3) N2 0.041(3) 0.037(3) 0.040(3) 0.004(3) 0.009(3) 0.000(3) O1 0.069(4) 0.034(3) 0.049(3) 0.005(2) 0.013(3) 0.002(3) C1 0.056(5) 0.052(4) 0.037(4) -0.003(4) 0.010(3) -0.010(4) C2 0.054(5) 0.052(5) 0.039(4) 0.011(4) 0.006(3) -0.003(4) C3 0.048(5) 0.048(5) 0.066(6) 0.009(4) 0.011(4) 0.011(4) C4 0.044(4) 0.046(4) 0.042(4) 0.004(3) 0.013(3) 0.005(3) C5 0.034(4) 0.040(4) 0.040(4) 0.001(3) 0.009(3) -0.003(3) C6 0.035(4) 0.041(4) 0.043(4) 0.005(3) 0.013(3) 0.001(3) C7 0.050(4) 0.037(4) 0.033(4) 0.007(3) 0.013(3) 0.004(3) C8 0.037(4) 0.034(4) 0.036(4) 0.006(3) 0.008(3) 0.006(3) C9 0.046(4) 0.039(4) 0.053(5) 0.004(4) 0.015(4) 0.003(3) C10 0.060(5) 0.045(4) 0.049(5) 0.014(4) 0.023(4) 0.013(4) C11 0.056(5) 0.043(4) 0.037(4) -0.006(3) 0.008(4) 0.002(4) Cl1 0.0453(10) 0.0442(10) 0.0543(11) 0.0056(9) 0.0156(9) 0.0070(8) O2 0.23(3) 0.16(2) 0.058(10) 0.049(12) 0.086(15) 0.11(2) O3 0.26(4) 0.030(7) 0.16(2) 0.014(10) 0.14(3) 0.019(13) O4 0.077(12) 0.136(19) 0.16(2) 0.046(16) 0.078(14) 0.053(12) O5 0.101(16) 0.20(3) 0.27(3) -0.19(3) -0.034(18) -0.011(17) O2' 0.115(18) 0.24(3) 0.42(6) 0.27(4) 0.17(3) 0.09(2) O3' 0.088(17) 0.24(4) 0.25(4) 0.17(3) 0.06(2) 0.09(2) O4' 0.073(14) 0.21(3) 0.20(3) 0.00(2) 0.020(14) -0.036(18) O5' 0.25(4) 0.24(4) 0.22(4) -0.15(3) -0.01(3) 0.06(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N2 2.164(6) 2_645 ? Ag1 N1 2.180(6) . ? N1 C1 1.337(10) . ? N1 C5 1.349(10) . ? N2 C11 1.327(10) . ? N2 C7 1.338(9) . ? N2 Ag1 2.164(6) 2_655 ? O1 C6 1.220(8) . ? C1 C2 1.361(12) . ? C2 C3 1.346(12) . ? C3 C4 1.374(11) . ? C4 C5 1.362(10) . ? C5 C6 1.519(10) . ? C6 C8 1.496(10) . ? C7 C8 1.381(10) . ? C8 C9 1.373(10) . ? C9 C10 1.377(11) . ? C10 C11 1.405(11) . ? Cl1 O4 1.355(8) . ? Cl1 O2' 1.364(8) . ? Cl1 O3' 1.364(8) . ? Cl1 O5' 1.370(9) . ? Cl1 O3 1.372(8) . ? Cl1 O5 1.378(8) . ? Cl1 O4' 1.380(8) . ? Cl1 O2 1.389(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 N2 Ag1 N1 174.9(2) 2_645 . ? C1 N1 C5 116.7(6) . . ? C1 N1 Ag1 121.4(5) . . ? C5 N1 Ag1 121.9(5) . . ? C11 N2 C7 118.4(6) . . ? C11 N2 Ag1 121.7(5) . 2_655 ? C7 N2 Ag1 119.9(5) . 2_655 ? N1 C1 C2 123.4(8) . . ? C3 C2 C1 119.5(7) . . ? C2 C3 C4 118.6(7) . . ? C5 C4 C3 119.6(7) . . ? N1 C5 C4 122.2(7) . . ? N1 C5 C6 116.1(6) . . ? C4 C5 C6 121.3(7) . . ? O1 C6 C8 119.9(6) . . ? O1 C6 C5 120.1(7) . . ? C8 C6 C5 120.0(6) . . ? N2 C7 C8 122.8(6) . . ? C9 C8 C7 118.5(7) . . ? C9 C8 C6 120.4(6) . . ? C7 C8 C6 120.9(6) . . ? C8 C9 C10 119.9(7) . . ? C9 C10 C11 117.8(7) . . ? N2 C11 C10 122.6(7) . . ? O4 Cl1 O2' 118.5(13) . . ? O4 Cl1 O3' 136.0(15) . . ? O2' Cl1 O3' 105.4(12) . . ? O4 Cl1 O5' 47.3(13) . . ? O2' Cl1 O5' 104.3(12) . . ? O3' Cl1 O5' 126(3) . . ? O4 Cl1 O3 113.6(11) . . ? O2' Cl1 O3 116.1(16) . . ? O3' Cl1 O3 35.7(17) . . ? O5' Cl1 O3 138.5(19) . . ? O4 Cl1 O5 110.7(10) . . ? O2' Cl1 O5 91(2) . . ? O3' Cl1 O5 68.7(18) . . ? O5' Cl1 O5 66.1(15) . . ? O3 Cl1 O5 102.7(19) . . ? O4 Cl1 O4' 55.6(12) . . ? O2' Cl1 O4' 115(2) . . ? O3' Cl1 O4' 104.1(11) . . ? O5' Cl1 O4' 102.7(12) . . ? O3 Cl1 O4' 68.8(14) . . ? O5 Cl1 O4' 153.3(18) . . ? O4 Cl1 O2 112.8(14) . . ? O2' Cl1 O2 19(2) . . ? O3' Cl1 O2 108(2) . . ? O5' Cl1 O2 115(2) . . ? O3 Cl1 O2 106.3(9) . . ? O5 Cl1 O2 110.1(11) . . ? O4' Cl1 O2 96.6(17) . . ? 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 N2 Ag1 N1 C1 -1(3) 2_645 . . . ? N2 Ag1 N1 C5 178(2) 2_645 . . . ? C5 N1 C1 C2 -0.3(11) . . . . ? Ag1 N1 C1 C2 178.5(6) . . . . ? N1 C1 C2 C3 1.3(13) . . . . ? C1 C2 C3 C4 -1.7(12) . . . . ? C2 C3 C4 C5 1.2(12) . . . . ? C1 N1 C5 C4 -0.3(10) . . . . ? Ag1 N1 C5 C4 -179.1(5) . . . . ? C1 N1 C5 C6 173.3(6) . . . . ? Ag1 N1 C5 C6 -5.5(8) . . . . ? C3 C4 C5 N1 -0.2(11) . . . . ? C3 C4 C5 C6 -173.4(7) . . . . ? N1 C5 C6 O1 -27.0(10) . . . . ? C4 C5 C6 O1 146.6(7) . . . . ? N1 C5 C6 C8 152.6(6) . . . . ? C4 C5 C6 C8 -33.7(10) . . . . ? C11 N2 C7 C8 -1.8(10) . . . . ? Ag1 N2 C7 C8 178.5(5) 2_655 . . . ? N2 C7 C8 C9 3.2(10) . . . . ? N2 C7 C8 C6 -171.4(6) . . . . ? O1 C6 C8 C9 -33.9(10) . . . . ? C5 C6 C8 C9 146.4(7) . . . . ? O1 C6 C8 C7 140.6(7) . . . . ? C5 C6 C8 C7 -39.1(9) . . . . ? C7 C8 C9 C10 -2.1(10) . . . . ? C6 C8 C9 C10 172.6(7) . . . . ? C8 C9 C10 C11 -0.3(11) . . . . ? C7 N2 C11 C10 -0.7(11) . . . . ? Ag1 N2 C11 C10 178.9(6) 2_655 . . . ? C9 C10 C11 N2 1.8(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.782 _refine_diff_density_min -1.053 _refine_diff_density_rms 0.131 #===END data_Compound(5) _database_code_depnum_ccdc_archive 'CCDC 278825' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 Ag F3 N2 O3' _chemical_formula_weight 405.08 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' F F 0.0171 0.0103 '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 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 7.7407(5) _cell_length_b 13.6362(8) _cell_length_c 13.5921(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.4240(10) _cell_angle_gamma 90.00 _cell_volume 1353.04(15) _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 Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.989 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 1.539 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.674420 _exptl_absorpt_correction_T_max 1.000000 _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 7177 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2388 _reflns_number_gt 1974 _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^)+(0.0557P)^2^+0.3269P] 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 2388 _refine_ls_number_parameters 226 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0879 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.090 _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 Ag1 Ag 0.38055(5) -0.05714(2) 0.06938(2) 0.05657(16) Uani 1 1 d . . . N1 N 0.2114(4) 0.0788(2) 0.0571(2) 0.0438(7) Uani 1 1 d . . . N2 N 0.5112(4) 0.2923(2) 0.4265(2) 0.0450(7) Uani 1 1 d . . . O1 O 0.3411(5) -0.0044(2) 0.2521(2) 0.0648(8) Uani 1 1 d . . . C1 C 0.1118(5) 0.1134(3) -0.0366(3) 0.0543(10) Uani 1 1 d . . . H1A H 0.1171 0.0808 -0.0956 0.065 Uiso 1 1 calc R . . C2 C 0.0005(6) 0.1956(3) -0.0500(4) 0.0616(12) Uani 1 1 d . . . H2A H -0.0666 0.2178 -0.1164 0.074 Uiso 1 1 calc R . . C3 C -0.0079(6) 0.2429(3) 0.0363(4) 0.0616(12) Uani 1 1 d . . . H3A H -0.0815 0.2981 0.0299 0.074 Uiso 1 1 calc R . . C4 C 0.0938(5) 0.2081(3) 0.1332(3) 0.0526(10) Uani 1 1 d . . . H4A H 0.0893 0.2394 0.1930 0.063 Uiso 1 1 calc R . . C5 C 0.2029(5) 0.1263(3) 0.1409(3) 0.0406(8) Uani 1 1 d . . . C6 C 0.3093(6) 0.0826(3) 0.2450(3) 0.0451(9) Uani 1 1 d . . . C7 C 0.4383(5) 0.2395(3) 0.3404(3) 0.0428(8) Uani 1 1 d . . . H7A H 0.4303 0.2676 0.2767 0.051 Uiso 1 1 calc R . . C8 C 0.3740(5) 0.1452(3) 0.3408(3) 0.0420(8) Uani 1 1 d . . . C9 C 0.3847(6) 0.1044(3) 0.4358(3) 0.0492(9) Uani 1 1 d . . . H9A H 0.3419 0.0412 0.4390 0.059 Uiso 1 1 calc R . . C10 C 0.4591(6) 0.1580(3) 0.5252(3) 0.0548(10) Uani 1 1 d . . . H10A H 0.4673 0.1316 0.5897 0.066 Uiso 1 1 calc R . . C11 C 0.5213(6) 0.2511(3) 0.5181(3) 0.0492(9) Uani 1 1 d . . . H11A H 0.5724 0.2870 0.5790 0.059 Uiso 1 1 calc R . . C12 C 0.2497(6) 0.5791(3) 0.2730(3) 0.0531(10) Uani 1 1 d . A . O2 O 0.3092(5) 0.5388(2) 0.3583(2) 0.0701(9) Uani 1 1 d . . . O3 O 0.2558(7) 0.6658(3) 0.2492(3) 0.1004(14) Uani 1 1 d . . . C13 C 0.1621(6) 0.5126(3) 0.1818(3) 0.0683(13) Uani 1 1 d D . . F1 F 0.256(2) 0.4394(11) 0.1637(14) 0.194(11) Uani 0.50 1 d PD A 1 F2 F 0.081(3) 0.5517(9) 0.0906(7) 0.208(10) Uani 0.50 1 d PD A 1 F3 F 0.0223(13) 0.4630(9) 0.1961(9) 0.125(4) Uani 0.50 1 d PD A 1 F1' F 0.2285(18) 0.4231(4) 0.2025(8) 0.103(4) Uani 0.50 1 d PD A 2 F2' F 0.2102(12) 0.5372(7) 0.0996(5) 0.084(2) Uani 0.50 1 d PD A 2 F3' F -0.0146(9) 0.5094(15) 0.1491(10) 0.191(9) Uani 0.50 1 d PD A 2 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 0.0709(3) 0.0406(2) 0.0543(2) -0.00453(13) 0.01568(17) 0.01096(14) N1 0.0481(18) 0.0366(15) 0.0436(18) -0.0026(13) 0.0112(14) -0.0014(13) N2 0.0535(19) 0.0393(16) 0.0413(17) 0.0024(13) 0.0147(14) -0.0015(13) O1 0.107(2) 0.0368(16) 0.0493(17) 0.0048(13) 0.0247(17) 0.0113(15) C1 0.058(2) 0.054(2) 0.043(2) -0.0007(19) 0.0059(19) -0.0010(19) C2 0.052(2) 0.059(3) 0.060(3) 0.008(2) 0.000(2) 0.002(2) C3 0.050(2) 0.048(2) 0.078(3) 0.003(2) 0.010(2) 0.0108(18) C4 0.053(2) 0.046(2) 0.056(2) -0.0036(19) 0.0141(19) 0.0074(17) C5 0.045(2) 0.0349(17) 0.042(2) -0.0030(15) 0.0147(16) -0.0045(15) C6 0.056(2) 0.036(2) 0.047(2) 0.0035(16) 0.0214(18) 0.0019(16) C7 0.050(2) 0.0417(19) 0.0376(19) 0.0054(16) 0.0163(16) -0.0002(16) C8 0.046(2) 0.0390(19) 0.043(2) 0.0016(16) 0.0169(16) 0.0028(15) C9 0.062(2) 0.041(2) 0.048(2) 0.0046(18) 0.0238(19) -0.0012(18) C10 0.075(3) 0.052(2) 0.040(2) 0.0089(19) 0.023(2) 0.001(2) C11 0.060(2) 0.044(2) 0.042(2) -0.0008(17) 0.0144(18) 0.0005(18) C12 0.059(3) 0.057(3) 0.044(2) 0.0023(19) 0.017(2) 0.0066(19) O2 0.087(2) 0.071(2) 0.0449(18) 0.0094(15) 0.0128(16) 0.0108(17) O3 0.166(4) 0.058(2) 0.066(2) 0.0037(18) 0.022(2) -0.006(2) C13 0.079(3) 0.071(3) 0.050(3) -0.005(2) 0.015(2) 0.000(3) F1 0.129(9) 0.25(2) 0.22(2) -0.154(17) 0.074(12) 0.013(11) F2 0.32(2) 0.125(9) 0.070(7) 0.018(6) -0.080(11) -0.052(13) F3 0.089(8) 0.155(8) 0.110(9) -0.045(7) 0.003(6) -0.057(7) F1' 0.184(13) 0.031(3) 0.081(5) -0.012(3) 0.025(6) 0.009(4) F2' 0.109(6) 0.105(6) 0.031(3) -0.012(3) 0.015(4) 0.018(5) F3' 0.033(4) 0.39(3) 0.116(12) -0.091(13) -0.016(5) 0.018(8) _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 2.211(3) 2_645 ? Ag1 N1 2.243(3) . ? N1 C5 1.331(5) . ? N1 C1 1.336(5) . ? N2 C7 1.329(5) . ? N2 C11 1.344(5) . ? N2 Ag1 2.211(3) 2_655 ? O1 C6 1.210(5) . ? C1 C2 1.389(6) . ? C2 C3 1.359(7) . ? C3 C4 1.375(6) . ? C4 C5 1.382(5) . ? C5 C6 1.503(5) . ? C6 C8 1.497(5) . ? C7 C8 1.380(5) . ? C8 C9 1.382(5) . ? C9 C10 1.369(6) . ? C10 C11 1.373(6) . ? C12 O2 1.226(5) . ? C12 O3 1.231(5) . ? C12 C13 1.503(6) . ? C13 F3' 1.290(7) . ? C13 F2 1.303(7) . ? C13 F1 1.307(8) . ? C13 F1' 1.317(7) . ? C13 F2' 1.332(7) . ? C13 F3 1.343(7) . ? 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 167.42(12) 2_645 . ? C5 N1 C1 117.8(3) . . ? C5 N1 Ag1 122.2(2) . . ? C1 N1 Ag1 120.0(3) . . ? C7 N2 C11 117.8(3) . . ? C7 N2 Ag1 124.8(2) . 2_655 ? C11 N2 Ag1 117.4(3) . 2_655 ? N1 C1 C2 123.2(4) . . ? C3 C2 C1 118.4(4) . . ? C2 C3 C4 119.1(4) . . ? C3 C4 C5 119.5(4) . . ? N1 C5 C4 122.1(4) . . ? N1 C5 C6 116.4(3) . . ? C4 C5 C6 121.4(3) . . ? O1 C6 C8 119.3(3) . . ? O1 C6 C5 119.8(3) . . ? C8 C6 C5 120.9(3) . . ? N2 C7 C8 123.3(3) . . ? C7 C8 C9 117.9(3) . . ? C7 C8 C6 123.0(3) . . ? C9 C8 C6 118.9(3) . . ? C10 C9 C8 119.5(4) . . ? C9 C10 C11 118.9(4) . . ? N2 C11 C10 122.6(4) . . ? O2 C12 O3 130.1(4) . . ? O2 C12 C13 115.8(4) . . ? O3 C12 C13 114.1(4) . . ? F3' C13 F2 64.2(9) . . ? F3' C13 F1 120.3(12) . . ? F2 C13 F1 105.0(9) . . ? F3' C13 F1' 109.7(9) . . ? F2 C13 F1' 127.8(9) . . ? F1 C13 F1' 29.6(9) . . ? F3' C13 F2' 106.2(7) . . ? F2 C13 F2' 44.1(9) . . ? F1 C13 F2' 72.9(9) . . ? F1' C13 F2' 102.4(6) . . ? F3' C13 F3 38.8(8) . . ? F2 C13 F3 100.7(8) . . ? F1 C13 F3 99.8(9) . . ? F1' C13 F3 77.2(8) . . ? F2' C13 F3 135.3(7) . . ? F3' C13 C12 116.1(8) . . ? F2 C13 C12 118.7(6) . . ? F1 C13 C12 119.2(9) . . ? F1' C13 C12 110.2(6) . . ? F2' C13 C12 111.4(5) . . ? F3 C13 C12 110.4(6) . . ? 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 N2 Ag1 N1 C5 101.6(5) 2_645 . . . ? N2 Ag1 N1 C1 -76.9(6) 2_645 . . . ? C5 N1 C1 C2 -0.2(6) . . . . ? Ag1 N1 C1 C2 178.4(3) . . . . ? N1 C1 C2 C3 -0.3(7) . . . . ? C1 C2 C3 C4 0.2(7) . . . . ? C2 C3 C4 C5 0.3(7) . . . . ? C1 N1 C5 C4 0.8(6) . . . . ? Ag1 N1 C5 C4 -177.8(3) . . . . ? C1 N1 C5 C6 177.1(3) . . . . ? Ag1 N1 C5 C6 -1.5(4) . . . . ? C3 C4 C5 N1 -0.8(6) . . . . ? C3 C4 C5 C6 -176.9(4) . . . . ? N1 C5 C6 O1 -26.2(6) . . . . ? C4 C5 C6 O1 150.1(4) . . . . ? N1 C5 C6 C8 154.9(3) . . . . ? C4 C5 C6 C8 -28.7(5) . . . . ? C11 N2 C7 C8 -0.3(6) . . . . ? Ag1 N2 C7 C8 179.2(3) 2_655 . . . ? N2 C7 C8 C9 0.6(6) . . . . ? N2 C7 C8 C6 -173.7(4) . . . . ? O1 C6 C8 C7 143.0(4) . . . . ? C5 C6 C8 C7 -38.1(6) . . . . ? O1 C6 C8 C9 -31.3(6) . . . . ? C5 C6 C8 C9 147.6(4) . . . . ? C7 C8 C9 C10 -0.5(6) . . . . ? C6 C8 C9 C10 174.2(4) . . . . ? C8 C9 C10 C11 0.0(7) . . . . ? C7 N2 C11 C10 -0.3(6) . . . . ? Ag1 N2 C11 C10 -179.8(3) 2_655 . . . ? C9 C10 C11 N2 0.4(7) . . . . ? O2 C12 C13 F3' 100.0(11) . . . . ? O3 C12 C13 F3' -82.3(11) . . . . ? O2 C12 C13 F2 173.5(12) . . . . ? O3 C12 C13 F2 -8.9(13) . . . . ? O2 C12 C13 F1 -56.5(11) . . . . ? O3 C12 C13 F1 121.1(11) . . . . ? O2 C12 C13 F1' -25.3(8) . . . . ? O3 C12 C13 F1' 152.3(7) . . . . ? O2 C12 C13 F2' -138.3(6) . . . . ? O3 C12 C13 F2' 39.4(7) . . . . ? O2 C12 C13 F3 58.1(8) . . . . ? O3 C12 C13 F3 -124.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.718 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.081 #===END data_Compound(7) _database_code_depnum_ccdc_archive 'CCDC 278826' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Cl2 Cu N3 O10' _chemical_formula_weight 505.70 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.9186(11) _cell_length_b 8.1263(5) _cell_length_c 24.8022(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3813.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.38 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2040 _exptl_absorpt_coefficient_mu 1.485 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.764402 _exptl_absorpt_correction_T_max 1.000000 _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 19358 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3354 _reflns_number_gt 2742 _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^)+(0.0535P)^2^+7.6289P] 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 3354 _refine_ls_number_parameters 318 _refine_ls_number_restraints 372 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1131 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.349 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.43389(3) 0.44595(7) 0.14474(2) 0.0266(2) Uani 1 1 d . . . O1 O 0.50582(16) 0.3415(4) 0.19347(12) 0.0301(7) Uani 1 1 d . . . N1 N 0.49215(19) 0.3272(5) 0.09004(13) 0.0251(8) Uani 1 1 d . . . N2 N 0.61491(19) 0.0297(5) 0.28937(14) 0.0270(8) Uani 1 1 d . . . N3 N 0.3593(2) 0.5280(5) 0.09539(16) 0.0356(10) Uani 1 1 d . . . C1 C 0.4810(3) 0.3188(6) 0.03727(17) 0.0318(11) Uani 1 1 d . . . H1A H 0.4443 0.3794 0.0222 0.038 Uiso 1 1 calc R . . C2 C 0.5230(3) 0.2217(6) 0.00374(19) 0.0365(12) Uani 1 1 d . . . H2A H 0.5154 0.2204 -0.0333 0.044 Uiso 1 1 calc R . . C3 C 0.5757(3) 0.1279(7) 0.02621(19) 0.0375(12) Uani 1 1 d . . . H3A H 0.6033 0.0603 0.0045 0.045 Uiso 1 1 calc R . . C4 C 0.5875(2) 0.1344(6) 0.08107(18) 0.0306(10) Uani 1 1 d . . . H4A H 0.6226 0.0708 0.0969 0.037 Uiso 1 1 calc R . . C5 C 0.5460(2) 0.2371(5) 0.11169(16) 0.0240(9) Uani 1 1 d . . . C6 C 0.5503(2) 0.2555(5) 0.17083(17) 0.0238(9) Uani 1 1 d . . . C7 C 0.5749(2) 0.1069(6) 0.25284(18) 0.0265(10) Uani 1 1 d . . . H7A H 0.5268 0.1191 0.2597 0.032 Uiso 1 1 calc R . . C8 C 0.6018(2) 0.1693(6) 0.20534(17) 0.0255(9) Uani 1 1 d . . . C9 C 0.6736(3) 0.1526(7) 0.19524(19) 0.0364(12) Uani 1 1 d . . . H9A H 0.6933 0.1934 0.1636 0.044 Uiso 1 1 calc R . . C10 C 0.7152(3) 0.0744(7) 0.2331(2) 0.0410(13) Uani 1 1 d . . . H10A H 0.7634 0.0619 0.2273 0.049 Uiso 1 1 calc R . . C11 C 0.6843(3) 0.0147(6) 0.2797(2) 0.0348(11) Uani 1 1 d . . . H11A H 0.7126 -0.0375 0.3051 0.042 Uiso 1 1 calc R . . C12 C 0.2627(3) 0.6793(8) 0.0413(2) 0.0546(16) Uani 1 1 d . . . H12C H 0.2783 0.7887 0.0328 0.065 Uiso 1 1 calc R . . H12B H 0.2204 0.6850 0.0626 0.065 Uiso 1 1 calc R . . H12A H 0.2533 0.6202 0.0086 0.065 Uiso 1 1 calc R . . C13 C 0.3177(3) 0.5944(6) 0.0717(2) 0.0342(11) Uani 1 1 d . . . Cl1 Cl 0.82887(7) 0.11660(19) 0.08297(6) 0.0481(4) Uani 1 1 d D . . O2 O 0.7562(2) 0.1227(8) 0.07513(19) 0.0837(17) Uani 1 1 d D A . O3 O 0.8460(4) 0.0450(12) 0.1329(2) 0.107(3) Uani 0.865(9) 1 d PDU A 1 O4 O 0.8595(3) 0.0087(7) 0.0433(2) 0.080(2) Uani 0.865(9) 1 d PDU A 1 O5 O 0.8616(4) 0.2666(8) 0.0737(5) 0.150(4) Uani 0.865(9) 1 d PDU A 1 O3' O 0.8443(11) 0.218(4) 0.1278(11) 0.077(11) Uani 0.135(9) 1 d PDU A 2 O4' O 0.8521(13) -0.0426(18) 0.0944(18) 0.130(14) Uani 0.135(9) 1 d PDU A 2 O5' O 0.8641(12) 0.181(5) 0.0381(9) 0.124(14) Uani 0.135(9) 1 d PDU A 2 Cl2 Cl 0.37771(7) 0.01397(16) 0.15051(6) 0.0418(3) Uani 1 1 d DU . . O6 O 0.3585(2) 0.1809(5) 0.1565(2) 0.0642(12) Uani 1 1 d DU B . O7 O 0.3289(4) -0.0988(7) 0.1682(4) 0.093(3) Uani 0.783(10) 1 d PDU B 1 O8 O 0.4459(3) -0.0165(7) 0.1727(3) 0.069(2) Uani 0.783(10) 1 d PDU B 1 O9 O 0.3882(5) -0.0096(10) 0.0936(2) 0.102(3) Uani 0.783(10) 1 d PDU B 1 O7' O 0.3739(16) -0.043(3) 0.2048(5) 0.108(9) Uani 0.217(10) 1 d PDU B 2 O8' O 0.4443(7) -0.013(2) 0.1301(11) 0.070(7) Uani 0.217(10) 1 d PDU B 2 O9' O 0.3245(10) -0.067(2) 0.1216(11) 0.102(9) Uani 0.217(10) 1 d PDU B 2 O1W O 0.5009(2) 0.6746(5) 0.13816(15) 0.0484(10) Uani 1 1 d . . . H1WA H 0.4783 0.7541 0.1490 0.080 Uiso 1 1 d R . . H1WB H 0.5474 0.6684 0.1385 0.080 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0283(3) 0.0326(3) 0.0189(3) -0.0044(2) -0.0042(2) 0.0078(2) O1 0.0332(18) 0.0370(18) 0.0200(15) -0.0009(13) -0.0031(13) 0.0116(15) N1 0.030(2) 0.0280(19) 0.0171(17) 0.0000(15) -0.0016(15) -0.0009(16) N2 0.026(2) 0.033(2) 0.0228(19) 0.0067(16) -0.0037(15) -0.0023(16) N3 0.038(2) 0.042(2) 0.027(2) 0.0000(18) -0.0076(19) 0.011(2) C1 0.038(3) 0.037(3) 0.021(2) -0.001(2) -0.0038(19) -0.001(2) C2 0.049(3) 0.042(3) 0.018(2) -0.005(2) -0.001(2) -0.006(2) C3 0.040(3) 0.045(3) 0.028(3) -0.013(2) 0.011(2) -0.002(2) C4 0.027(2) 0.036(3) 0.030(2) -0.003(2) 0.0016(19) 0.001(2) C5 0.024(2) 0.025(2) 0.022(2) 0.0037(18) -0.0002(17) -0.0011(18) C6 0.023(2) 0.028(2) 0.020(2) 0.0023(18) 0.0012(17) -0.0002(19) C7 0.023(2) 0.033(2) 0.024(2) 0.0015(19) -0.0012(18) 0.0016(19) C8 0.025(2) 0.030(2) 0.021(2) 0.0008(18) -0.0031(18) -0.0005(19) C9 0.030(3) 0.052(3) 0.027(2) 0.010(2) 0.003(2) 0.002(2) C10 0.020(2) 0.062(4) 0.041(3) 0.013(3) 0.004(2) 0.010(2) C11 0.027(3) 0.044(3) 0.034(3) 0.013(2) -0.006(2) 0.004(2) C12 0.043(3) 0.063(4) 0.058(4) 0.015(3) -0.013(3) 0.015(3) C13 0.039(3) 0.033(3) 0.030(3) -0.001(2) -0.001(2) 0.002(2) Cl1 0.0307(7) 0.0624(9) 0.0510(8) -0.0001(7) -0.0016(6) 0.0001(6) O2 0.036(2) 0.139(5) 0.076(3) 0.014(3) 0.001(2) 0.004(3) O3 0.094(5) 0.186(9) 0.043(3) 0.010(4) -0.001(3) 0.052(6) O4 0.084(4) 0.086(5) 0.069(4) -0.001(3) 0.028(3) 0.015(3) O5 0.111(6) 0.063(5) 0.275(14) -0.028(6) 0.028(8) -0.029(5) O3' 0.028(15) 0.13(3) 0.07(2) -0.03(2) 0.004(14) -0.002(18) O4' 0.11(2) 0.15(3) 0.13(3) 0.03(3) -0.03(2) 0.07(2) O5' 0.08(2) 0.14(3) 0.15(3) 0.00(2) 0.08(2) -0.05(2) Cl2 0.0364(7) 0.0327(7) 0.0565(8) -0.0013(6) 0.0063(6) 0.0009(5) O6 0.056(3) 0.039(2) 0.097(3) -0.010(2) 0.007(2) 0.007(2) O7 0.056(4) 0.051(4) 0.171(9) 0.011(5) 0.054(5) -0.009(3) O8 0.053(4) 0.051(3) 0.102(6) -0.010(4) -0.026(4) 0.008(3) O9 0.154(9) 0.105(6) 0.048(4) -0.029(4) 0.005(5) 0.021(6) O7' 0.13(2) 0.099(17) 0.098(17) 0.037(14) 0.010(16) 0.035(16) O8' 0.057(13) 0.049(11) 0.106(18) 0.011(13) 0.039(13) 0.004(10) O9' 0.113(18) 0.044(13) 0.15(2) -0.028(14) -0.017(18) -0.029(13) O1W 0.039(2) 0.042(2) 0.065(3) -0.0057(19) 0.0130(18) 0.0016(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 Cu1 N3 1.983(4) . ? Cu1 N1 1.997(4) . ? Cu1 N2 1.997(4) 3_655 ? Cu1 O1 2.008(3) . ? Cu1 O1W 2.255(4) . ? Cu1 O6 2.599(4) . ? Cu1 C6 2.769(4) . ? Cu1 C5 2.838(4) . ? Cu1 C7 2.862(4) 3_655 ? Cu1 C11 2.971(5) 3_655 ? Cu1 C1 2.995(4) . ? O1 C6 1.230(5) . ? N1 C1 1.327(5) . ? N1 C5 1.365(6) . ? N2 C7 1.338(6) . ? N2 C11 1.341(6) . ? N2 Cu1 1.997(4) 3_645 ? N3 C13 1.121(6) . ? C1 C2 1.395(7) . ? C2 C3 1.372(7) . ? C3 C4 1.380(7) . ? C4 C5 1.374(6) . ? C5 C6 1.477(6) . ? C6 C8 1.474(6) . ? C7 C8 1.380(6) . ? C7 Cu1 2.862(4) 3_645 ? C8 C9 1.387(6) . ? C9 C10 1.380(7) . ? C10 C11 1.383(7) . ? C11 Cu1 2.971(5) 3_645 ? C12 C13 1.459(7) . ? Cl1 O5 1.386(6) . ? Cl1 O2 1.389(4) . ? Cl1 O4' 1.395(9) . ? Cl1 O5' 1.397(9) . ? Cl1 O3 1.407(5) . ? Cl1 O3' 1.416(9) . ? Cl1 O4 1.440(5) . ? Cl2 O7 1.373(5) . ? Cl2 O8' 1.374(8) . ? Cl2 O9' 1.400(8) . ? Cl2 O6 1.412(4) . ? Cl2 O8 1.424(5) . ? Cl2 O7' 1.425(8) . ? Cl2 O9 1.438(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Cu1 N1 97.81(16) . . ? N3 Cu1 N2 93.53(16) . 3_655 ? N1 Cu1 N2 167.47(15) . 3_655 ? N3 Cu1 O1 174.62(16) . . ? N1 Cu1 O1 80.25(13) . . ? N2 Cu1 O1 87.98(13) 3_655 . ? N3 Cu1 O1W 94.46(17) . . ? N1 Cu1 O1W 92.23(14) . . ? N2 Cu1 O1W 92.18(15) 3_655 . ? O1 Cu1 O1W 90.64(14) . . ? N3 Cu1 O6 87.57(16) . . ? N1 Cu1 O6 88.78(14) . . ? N2 Cu1 O6 86.39(15) 3_655 . ? O1 Cu1 O6 87.37(14) . . ? O1W Cu1 O6 177.59(15) . . ? N3 Cu1 C6 153.91(15) . . ? N1 Cu1 C6 56.59(13) . . ? N2 Cu1 C6 111.54(14) 3_655 . ? O1 Cu1 C6 23.66(12) . . ? O1W Cu1 C6 91.76(13) . . ? O6 Cu1 C6 86.96(13) . . ? N3 Cu1 C5 123.68(14) . . ? N1 Cu1 C5 26.10(13) . . ? N2 Cu1 C5 141.82(13) 3_655 . ? O1 Cu1 C5 54.16(12) . . ? O1W Cu1 C5 92.99(13) . . ? O6 Cu1 C5 86.95(12) . . ? C6 Cu1 C5 30.51(12) . . ? N3 Cu1 C7 110.67(15) . 3_655 ? N1 Cu1 C7 148.85(14) . 3_655 ? N2 Cu1 C7 24.63(14) 3_655 3_655 ? O1 Cu1 C7 72.43(13) . 3_655 ? O1W Cu1 C7 73.74(13) . 3_655 ? O6 Cu1 C7 104.33(14) . 3_655 ? C6 Cu1 C7 95.40(13) . 3_655 ? C5 Cu1 C7 124.96(12) . 3_655 ? N3 Cu1 C11 77.92(16) . 3_655 ? N1 Cu1 C11 159.25(15) . 3_655 ? N2 Cu1 C11 21.79(14) 3_655 3_655 ? O1 Cu1 C11 102.11(13) . 3_655 ? O1W Cu1 C11 108.27(13) . 3_655 ? O6 Cu1 C11 70.86(13) . 3_655 ? C6 Cu1 C11 123.81(13) . 3_655 ? C5 Cu1 C11 149.02(13) . 3_655 ? C7 Cu1 C11 46.42(13) 3_655 3_655 ? N3 Cu1 C1 77.21(15) . . ? N1 Cu1 C1 20.62(14) . . ? N2 Cu1 C1 169.71(14) 3_655 . ? O1 Cu1 C1 100.84(13) . . ? O1W Cu1 C1 93.01(13) . . ? O6 Cu1 C1 88.71(14) . . ? C6 Cu1 C1 77.18(13) . . ? C5 Cu1 C1 46.67(13) . . ? C7 Cu1 C1 164.77(13) 3_655 . ? C11 Cu1 C1 148.29(13) 3_655 . ? C6 O1 Cu1 115.4(3) . . ? C1 N1 C5 118.6(4) . . ? C1 N1 Cu1 127.4(3) . . ? C5 N1 Cu1 113.8(3) . . ? C7 N2 C11 118.4(4) . . ? C7 N2 Cu1 116.9(3) . 3_645 ? C11 N2 Cu1 124.7(3) . 3_645 ? C13 N3 Cu1 170.1(4) . . ? N1 C1 C2 121.8(4) . . ? N1 C1 Cu1 32.0(2) . . ? C2 C1 Cu1 153.6(3) . . ? C3 C2 C1 119.0(4) . . ? C2 C3 C4 119.8(5) . . ? C5 C4 C3 118.4(5) . . ? N1 C5 C4 122.3(4) . . ? N1 C5 C6 112.2(4) . . ? C4 C5 C6 125.4(4) . . ? N1 C5 Cu1 40.06(19) . . ? C4 C5 Cu1 161.7(3) . . ? C6 C5 Cu1 72.2(2) . . ? O1 C6 C8 117.2(4) . . ? O1 C6 C5 118.2(4) . . ? C8 C6 C5 124.4(4) . . ? O1 C6 Cu1 40.9(2) . . ? C8 C6 Cu1 158.0(3) . . ? C5 C6 Cu1 77.3(2) . . ? N2 C7 C8 122.7(4) . . ? N2 C7 Cu1 38.5(2) . 3_645 ? C8 C7 Cu1 161.2(3) . 3_645 ? C7 C8 C9 118.7(4) . . ? C7 C8 C6 115.2(4) . . ? C9 C8 C6 126.1(4) . . ? C10 C9 C8 118.7(4) . . ? C9 C10 C11 119.3(4) . . ? N2 C11 C10 122.1(4) . . ? N2 C11 Cu1 33.6(2) . 3_645 ? C10 C11 Cu1 155.7(3) . 3_645 ? N3 C13 C12 179.2(6) . . ? O5 Cl1 O2 112.8(5) . . ? O5 Cl1 O4' 135.1(12) . . ? O2 Cl1 O4' 111.9(11) . . ? O5 Cl1 O5' 47.7(16) . . ? O2 Cl1 O5' 110.3(11) . . ? O4' Cl1 O5' 110.9(11) . . ? O5 Cl1 O3 114.0(6) . . ? O2 Cl1 O3 111.5(4) . . ? O4' Cl1 O3 50.6(17) . . ? O5' Cl1 O3 138.2(11) . . ? O5 Cl1 O3' 61.7(15) . . ? O2 Cl1 O3' 107.1(9) . . ? O4' Cl1 O3' 108.5(11) . . ? O5' Cl1 O3' 108.0(11) . . ? O3 Cl1 O3' 60.1(16) . . ? O5 Cl1 O4 104.0(5) . . ? O2 Cl1 O4 109.0(4) . . ? O4' Cl1 O4 56.4(18) . . ? O5' Cl1 O4 59.4(17) . . ? O3 Cl1 O4 104.9(4) . . ? O3' Cl1 O4 144.0(9) . . ? O7 Cl2 O8' 128.9(8) . . ? O7 Cl2 O9' 50.7(11) . . ? O8' Cl2 O9' 113.3(10) . . ? O7 Cl2 O6 115.7(3) . . ? O8' Cl2 O6 115.3(8) . . ? O9' Cl2 O6 108.7(8) . . ? O7 Cl2 O8 111.7(5) . . ? O8' Cl2 O8 44.3(11) . . ? O9' Cl2 O8 140.2(9) . . ? O6 Cl2 O8 111.0(3) . . ? O7 Cl2 O7' 56.5(11) . . ? O8' Cl2 O7' 110.0(10) . . ? O9' Cl2 O7' 107.2(10) . . ? O6 Cl2 O7' 101.5(8) . . ? O8 Cl2 O7' 67.9(11) . . ? O7 Cl2 O9 108.5(5) . . ? O8' Cl2 O9 59.4(11) . . ? O9' Cl2 O9 62.2(12) . . ? O6 Cl2 O9 105.5(4) . . ? O8 Cl2 O9 103.4(5) . . ? O7' Cl2 O9 153.0(9) . . ? Cl2 O6 Cu1 130.0(3) . . ? 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 N3 Cu1 O1 C6 68.5(17) . . . . ? N1 Cu1 O1 C6 -0.8(3) . . . . ? N2 Cu1 O1 C6 174.9(3) 3_655 . . . ? O1W Cu1 O1 C6 -92.9(3) . . . . ? O6 Cu1 O1 C6 88.4(3) . . . . ? C5 Cu1 O1 C6 0.3(3) . . . . ? C7 Cu1 O1 C6 -165.6(3) 3_655 . . . ? C11 Cu1 O1 C6 158.2(3) 3_655 . . . ? C1 Cu1 O1 C6 0.2(3) . . . . ? N3 Cu1 N1 C1 2.2(4) . . . . ? N2 Cu1 N1 C1 156.9(6) 3_655 . . . ? O1 Cu1 N1 C1 177.1(4) . . . . ? O1W Cu1 N1 C1 -92.6(4) . . . . ? O6 Cu1 N1 C1 89.6(4) . . . . ? C6 Cu1 N1 C1 176.7(5) . . . . ? C5 Cu1 N1 C1 175.1(6) . . . . ? C7 Cu1 N1 C1 -154.1(4) 3_655 . . . ? C11 Cu1 N1 C1 78.7(6) 3_655 . . . ? N3 Cu1 N1 C5 -172.9(3) . . . . ? N2 Cu1 N1 C5 -18.3(9) 3_655 . . . ? O1 Cu1 N1 C5 2.0(3) . . . . ? O1W Cu1 N1 C5 92.2(3) . . . . ? O6 Cu1 N1 C5 -85.6(3) . . . . ? C6 Cu1 N1 C5 1.6(3) . . . . ? C7 Cu1 N1 C5 30.7(5) 3_655 . . . ? C11 Cu1 N1 C5 -96.5(5) 3_655 . . . ? C1 Cu1 N1 C5 -175.1(6) . . . . ? N1 Cu1 N3 C13 -140(3) . . . . ? N2 Cu1 N3 C13 45(3) 3_655 . . . ? O1 Cu1 N3 C13 151(2) . . . . ? O1W Cu1 N3 C13 -47(3) . . . . ? O6 Cu1 N3 C13 131(3) . . . . ? C6 Cu1 N3 C13 -151(2) . . . . ? C5 Cu1 N3 C13 -144(3) . . . . ? C7 Cu1 N3 C13 27(3) 3_655 . . . ? C11 Cu1 N3 C13 60(3) 3_655 . . . ? C1 Cu1 N3 C13 -139(3) . . . . ? C5 N1 C1 C2 -0.4(7) . . . . ? Cu1 N1 C1 C2 -175.3(4) . . . . ? C5 N1 C1 Cu1 174.9(6) . . . . ? N3 Cu1 C1 N1 -177.8(4) . . . . ? N2 Cu1 C1 N1 -151.5(8) 3_655 . . . ? O1 Cu1 C1 N1 -2.9(4) . . . . ? O1W Cu1 C1 N1 88.3(4) . . . . ? O6 Cu1 C1 N1 -90.0(4) . . . . ? C6 Cu1 C1 N1 -2.8(4) . . . . ? C5 Cu1 C1 N1 -2.9(4) . . . . ? C7 Cu1 C1 N1 59.3(7) 3_655 . . . ? C11 Cu1 C1 N1 -138.6(4) 3_655 . . . ? N3 Cu1 C1 C2 -168.8(8) . . . . ? N1 Cu1 C1 C2 9.0(7) . . . . ? N2 Cu1 C1 C2 -142.5(9) 3_655 . . . ? O1 Cu1 C1 C2 6.1(8) . . . . ? O1W Cu1 C1 C2 97.3(8) . . . . ? O6 Cu1 C1 C2 -81.0(8) . . . . ? C6 Cu1 C1 C2 6.2(8) . . . . ? C5 Cu1 C1 C2 6.0(7) . . . . ? C7 Cu1 C1 C2 68.2(10) 3_655 . . . ? C11 Cu1 C1 C2 -129.7(7) 3_655 . . . ? N1 C1 C2 C3 2.3(8) . . . . ? Cu1 C1 C2 C3 -3.3(11) . . . . ? C1 C2 C3 C4 -1.7(8) . . . . ? C2 C3 C4 C5 -0.6(7) . . . . ? C1 N1 C5 C4 -2.1(6) . . . . ? Cu1 N1 C5 C4 173.5(4) . . . . ? C1 N1 C5 C6 -178.3(4) . . . . ? Cu1 N1 C5 C6 -2.7(4) . . . . ? C1 N1 C5 Cu1 -175.6(5) . . . . ? C3 C4 C5 N1 2.6(7) . . . . ? C3 C4 C5 C6 178.3(4) . . . . ? C3 C4 C5 Cu1 16.0(13) . . . . ? N3 Cu1 C5 N1 8.4(4) . . . . ? N2 Cu1 C5 N1 173.7(3) 3_655 . . . ? O1 Cu1 C5 N1 -177.6(4) . . . . ? O1W Cu1 C5 N1 -89.0(3) . . . . ? O6 Cu1 C5 N1 93.4(3) . . . . ? C6 Cu1 C5 N1 -177.4(4) . . . . ? C7 Cu1 C5 N1 -161.2(3) 3_655 . . . ? C11 Cu1 C5 N1 136.8(3) 3_655 . . . ? C1 Cu1 C5 N1 2.3(3) . . . . ? N3 Cu1 C5 C4 -9.3(11) . . . . ? N1 Cu1 C5 C4 -17.7(10) . . . . ? N2 Cu1 C5 C4 155.9(10) 3_655 . . . ? O1 Cu1 C5 C4 164.7(11) . . . . ? O1W Cu1 C5 C4 -106.7(10) . . . . ? O6 Cu1 C5 C4 75.7(11) . . . . ? C6 Cu1 C5 C4 164.9(12) . . . . ? C7 Cu1 C5 C4 -178.9(10) 3_655 . . . ? C11 Cu1 C5 C4 119.1(10) 3_655 . . . ? C1 Cu1 C5 C4 -15.4(10) . . . . ? N3 Cu1 C5 C6 -174.2(3) . . . . ? N1 Cu1 C5 C6 177.4(4) . . . . ? N2 Cu1 C5 C6 -9.0(4) 3_655 . . . ? O1 Cu1 C5 C6 -0.2(2) . . . . ? O1W Cu1 C5 C6 88.4(2) . . . . ? O6 Cu1 C5 C6 -89.2(3) . . . . ? C7 Cu1 C5 C6 16.2(3) 3_655 . . . ? C11 Cu1 C5 C6 -45.8(4) 3_655 . . . ? C1 Cu1 C5 C6 179.7(3) . . . . ? Cu1 O1 C6 C8 -176.8(3) . . . . ? Cu1 O1 C6 C5 -0.5(5) . . . . ? N1 C5 C6 O1 2.2(6) . . . . ? C4 C5 C6 O1 -173.9(4) . . . . ? Cu1 C5 C6 O1 0.3(3) . . . . ? N1 C5 C6 C8 178.2(4) . . . . ? C4 C5 C6 C8 2.1(7) . . . . ? Cu1 C5 C6 C8 176.4(4) . . . . ? N1 C5 C6 Cu1 1.8(3) . . . . ? C4 C5 C6 Cu1 -174.2(5) . . . . ? N3 Cu1 C6 O1 -168.6(4) . . . . ? N1 Cu1 C6 O1 179.1(4) . . . . ? N2 Cu1 C6 O1 -5.5(4) 3_655 . . . ? O1W Cu1 C6 O1 87.6(3) . . . . ? O6 Cu1 C6 O1 -90.4(3) . . . . ? C5 Cu1 C6 O1 -179.5(5) . . . . ? C7 Cu1 C6 O1 13.7(3) 3_655 . . . ? C11 Cu1 C6 O1 -25.9(4) 3_655 . . . ? C1 Cu1 C6 O1 -179.7(3) . . . . ? N3 Cu1 C6 C8 -161.0(7) . . . . ? N1 Cu1 C6 C8 -173.4(9) . . . . ? N2 Cu1 C6 C8 2.1(9) 3_655 . . . ? O1 Cu1 C6 C8 7.6(7) . . . . ? O1W Cu1 C6 C8 95.1(8) . . . . ? O6 Cu1 C6 C8 -82.8(8) . . . . ? C5 Cu1 C6 C8 -172.0(10) . . . . ? C7 Cu1 C6 C8 21.3(8) 3_655 . . . ? C11 Cu1 C6 C8 -18.3(9) 3_655 . . . ? C1 Cu1 C6 C8 -172.2(8) . . . . ? N3 Cu1 C6 C5 11.0(5) . . . . ? N1 Cu1 C6 C5 -1.4(2) . . . . ? N2 Cu1 C6 C5 174.1(2) 3_655 . . . ? O1 Cu1 C6 C5 179.5(5) . . . . ? O1W Cu1 C6 C5 -92.9(2) . . . . ? O6 Cu1 C6 C5 89.1(2) . . . . ? C7 Cu1 C6 C5 -166.7(2) 3_655 . . . ? C11 Cu1 C6 C5 153.6(2) 3_655 . . . ? C1 Cu1 C6 C5 -0.2(2) . . . . ? C11 N2 C7 C8 1.0(7) . . . . ? Cu1 N2 C7 C8 -179.4(3) 3_645 . . . ? C11 N2 C7 Cu1 -179.6(6) . . . 3_645 ? N2 C7 C8 C9 -0.6(7) . . . . ? Cu1 C7 C8 C9 -1.8(13) 3_645 . . . ? N2 C7 C8 C6 -178.0(4) . . . . ? Cu1 C7 C8 C6 -179.2(8) 3_645 . . . ? O1 C6 C8 C7 38.6(6) . . . . ? C5 C6 C8 C7 -137.4(4) . . . . ? Cu1 C6 C8 C7 33.1(10) . . . . ? O1 C6 C8 C9 -138.5(5) . . . . ? C5 C6 C8 C9 45.4(7) . . . . ? Cu1 C6 C8 C9 -144.1(7) . . . . ? C7 C8 C9 C10 0.0(8) . . . . ? C6 C8 C9 C10 177.0(5) . . . . ? C8 C9 C10 C11 0.2(8) . . . . ? C7 N2 C11 C10 -0.8(8) . . . . ? Cu1 N2 C11 C10 179.6(4) 3_645 . . . ? C7 N2 C11 Cu1 179.6(6) . . . 3_645 ? C9 C10 C11 N2 0.3(9) . . . . ? C9 C10 C11 Cu1 0.8(13) . . . 3_645 ? Cu1 N3 C13 C12 -106(45) . . . . ? O7 Cl2 O6 Cu1 169.6(6) . . . . ? O8' Cl2 O6 Cu1 -7.4(14) . . . . ? O9' Cl2 O6 Cu1 -135.8(14) . . . . ? O8 Cl2 O6 Cu1 40.8(5) . . . . ? O7' Cl2 O6 Cu1 111.4(13) . . . . ? O9 Cl2 O6 Cu1 -70.5(5) . . . . ? N3 Cu1 O6 Cl2 127.8(4) . . . . ? N1 Cu1 O6 Cl2 29.9(4) . . . . ? N2 Cu1 O6 Cl2 -138.6(4) 3_655 . . . ? O1 Cu1 O6 Cl2 -50.4(4) . . . . ? O1W Cu1 O6 Cl2 -85(3) . . . . ? C6 Cu1 O6 Cl2 -26.7(4) . . . . ? C5 Cu1 O6 Cl2 3.8(4) . . . . ? C7 Cu1 O6 Cl2 -121.5(4) 3_655 . . . ? C11 Cu1 O6 Cl2 -154.2(4) 3_655 . . . ? C1 Cu1 O6 Cl2 50.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.701 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.090 #===END data_Compound(8) _database_code_depnum_ccdc_archive 'CCDC 278827' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H18 Cl2 Co N2 O14' _chemical_formula_weight 532.10 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 '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 13.0805(8) _cell_length_b 11.1580(7) _cell_length_c 13.8114(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.3980(10) _cell_angle_gamma 90.00 _cell_volume 2006.9(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 Block _exptl_crystal_colour Orange _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 1.195 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.618274 _exptl_absorpt_correction_T_max 1.000000 _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 10620 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3535 _reflns_number_gt 2846 _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^)+(0.0748P)^2^+1.9725P] 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 3535 _refine_ls_number_parameters 340 _refine_ls_number_restraints 174 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1299 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.321 _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 Co1 Co 0.02121(4) 0.60252(5) 0.26604(4) 0.0343(2) Uani 1 1 d . . . O1 O 0.3201(2) 0.1473(3) 0.2221(3) 0.0444(8) Uani 1 1 d . . . N1 N 0.4740(3) 0.2849(3) 0.1904(3) 0.0394(9) Uani 1 1 d . . . N2 N 0.0549(3) 0.4250(3) 0.2238(3) 0.0366(8) Uani 1 1 d . . . C1 C 0.5545(4) 0.3507(5) 0.1718(4) 0.0519(13) Uani 1 1 d . . . H1A H 0.6197 0.3172 0.1817 0.062 Uiso 1 1 calc R . . C2 C 0.5447(4) 0.4682(5) 0.1379(4) 0.0613(15) Uani 1 1 d . . . H2A H 0.6025 0.5123 0.1260 0.074 Uiso 1 1 calc R . . C3 C 0.4491(5) 0.5177(5) 0.1225(4) 0.0598(15) Uani 1 1 d . . . H3A H 0.4411 0.5960 0.0998 0.072 Uiso 1 1 calc R . . C4 C 0.3636(4) 0.4495(4) 0.1410(4) 0.0488(12) Uani 1 1 d . . . H4A H 0.2976 0.4806 0.1294 0.059 Uiso 1 1 calc R . . C5 C 0.3791(3) 0.3350(4) 0.1769(3) 0.0365(10) Uani 1 1 d . . . C6 C 0.2961(3) 0.2507(4) 0.1992(3) 0.0371(10) Uani 1 1 d . . . C7 C 0.1542(3) 0.3931(4) 0.2255(3) 0.0386(10) Uani 1 1 d . . . H7A H 0.2038 0.4480 0.2496 0.046 Uiso 1 1 calc R . . C8 C 0.1865(3) 0.2836(4) 0.1935(3) 0.0362(10) Uani 1 1 d . . . C9 C 0.1119(4) 0.1995(4) 0.1619(4) 0.0462(12) Uani 1 1 d . . . H9A H 0.1306 0.1236 0.1419 0.055 Uiso 1 1 calc R . . C10 C 0.0106(4) 0.2308(5) 0.1606(4) 0.0531(13) Uani 1 1 d . . . H10A H -0.0406 0.1764 0.1395 0.064 Uiso 1 1 calc R . . C11 C -0.0150(4) 0.3431(5) 0.1908(4) 0.0463(12) Uani 1 1 d . . . H11A H -0.0841 0.3635 0.1883 0.056 Uiso 1 1 calc R . . O1W O -0.1355(3) 0.5736(3) 0.2657(3) 0.0553(9) Uani 1 1 d . . . H1WA H -0.1906 0.5934 0.2162 0.12(3) Uiso 1 1 d R . . H1WB H -0.1612 0.5436 0.3247 0.14(3) Uiso 1 1 d R . . O2W O 0.0013(4) 0.6577(4) 0.1196(3) 0.0672(11) Uani 1 1 d . . . H2WA H -0.0045 0.7432 0.1080 0.14(3) Uiso 1 1 d R . . H2WB H 0.0498 0.6117 0.0857 0.34(10) Uiso 1 1 d R . . O3W O 0.0413(3) 0.5445(4) 0.4105(2) 0.0543(9) Uani 1 1 d . . . H3WA H 0.0534 0.6096 0.4567 0.10(3) Uiso 1 1 d R . . H3WB H 0.0820 0.4718 0.4182 0.12(3) Uiso 1 1 d R . . Cl1 Cl 0.24502(11) 0.30094(14) 0.48685(12) 0.0672(4) Uani 1 1 d D . . O2 O 0.1412(3) 0.3159(5) 0.4520(4) 0.0964(16) Uani 1 1 d D A . O3 O 0.2684(13) 0.3824(14) 0.5643(9) 0.120(7) Uani 0.50 1 d PD A 1 O4 O 0.3141(10) 0.3191(16) 0.4193(9) 0.125(8) Uani 0.50 1 d PD A 1 O5 O 0.2528(10) 0.1866(10) 0.5324(14) 0.147(7) Uani 0.50 1 d PD A 1 O3' O 0.2658(10) 0.3216(16) 0.5851(6) 0.103(6) Uani 0.50 1 d PD A 2 O4' O 0.3020(11) 0.3838(13) 0.4350(11) 0.121(6) Uani 0.50 1 d PD A 2 O5' O 0.2790(10) 0.1870(9) 0.4587(12) 0.126(5) Uani 0.50 1 d PD A 2 Cl2 Cl 0.20221(10) 0.72316(12) 0.59394(10) 0.0549(4) Uani 1 1 d D . . O6 O 0.0964(3) 0.7234(6) 0.5657(5) 0.121(2) Uani 1 1 d D B . O7 O 0.2337(8) 0.8422(6) 0.6079(11) 0.099(4) Uani 0.50 1 d PD B 1 O8 O 0.2345(10) 0.6536(11) 0.6723(7) 0.101(4) Uani 0.50 1 d PD B 1 O9 O 0.2442(9) 0.6786(12) 0.5098(6) 0.109(4) Uani 0.50 1 d PD B 1 O7' O 0.2354(11) 0.6056(8) 0.6064(15) 0.154(7) Uani 0.50 1 d PD B 2 O8' O 0.2622(9) 0.7875(16) 0.5365(10) 0.146(6) Uani 0.50 1 d PD B 2 O9' O 0.2106(7) 0.7742(13) 0.6882(6) 0.097(4) Uani 0.50 1 d PD B 2 O4W O -0.0369(11) 0.8978(10) 0.0924(10) 0.077(3) Uani 0.50 1 d P C 1 O4W' O -0.0351(11) 0.9509(11) 0.0630(10) 0.085(3) Uani 0.50 1 d P D 2 O5W O 0.1170(8) 0.4968(9) 0.0028(6) 0.178(4) 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 Co1 0.0299(3) 0.0347(4) 0.0388(4) -0.0017(2) 0.0054(2) 0.0013(2) O1 0.0343(17) 0.0297(17) 0.070(2) 0.0036(15) 0.0127(15) 0.0004(13) N1 0.036(2) 0.038(2) 0.044(2) 0.0031(17) 0.0050(16) -0.0064(16) N2 0.033(2) 0.0333(19) 0.044(2) -0.0020(16) 0.0055(16) 0.0009(16) C1 0.036(3) 0.056(3) 0.064(3) 0.013(3) 0.004(2) -0.010(2) C2 0.054(3) 0.056(3) 0.074(4) 0.016(3) 0.012(3) -0.019(3) C3 0.069(4) 0.040(3) 0.071(4) 0.013(3) 0.016(3) -0.007(3) C4 0.050(3) 0.038(3) 0.059(3) 0.006(2) 0.012(2) 0.005(2) C5 0.039(2) 0.032(2) 0.039(2) -0.0024(18) 0.0044(19) -0.0025(19) C6 0.039(2) 0.031(2) 0.043(3) -0.0066(19) 0.008(2) -0.0010(19) C7 0.032(2) 0.034(2) 0.049(3) -0.005(2) 0.0020(19) -0.0011(19) C8 0.036(2) 0.033(2) 0.040(2) -0.0007(18) 0.0040(19) -0.0002(18) C9 0.045(3) 0.034(2) 0.060(3) -0.009(2) 0.003(2) -0.002(2) C10 0.039(3) 0.047(3) 0.072(4) -0.011(3) -0.003(2) -0.009(2) C11 0.034(2) 0.048(3) 0.057(3) 0.000(2) 0.003(2) 0.000(2) O1W 0.0301(17) 0.070(2) 0.065(2) 0.0028(19) 0.0011(17) 0.0031(17) O2W 0.092(3) 0.065(3) 0.044(2) 0.0041(19) 0.008(2) 0.012(2) O3W 0.065(2) 0.060(2) 0.0380(19) 0.0027(17) 0.0015(16) -0.0050(19) Cl1 0.0540(9) 0.0690(10) 0.0757(11) -0.0040(8) -0.0085(7) 0.0076(7) O2 0.057(3) 0.107(4) 0.120(4) 0.020(3) -0.018(3) 0.002(3) O3 0.125(13) 0.150(15) 0.083(10) -0.027(10) 0.003(9) -0.021(11) O4 0.063(7) 0.23(2) 0.081(8) -0.044(12) 0.017(6) 0.025(11) O5 0.098(10) 0.107(11) 0.24(2) 0.077(13) 0.035(12) 0.045(8) O3' 0.059(7) 0.187(19) 0.061(7) 0.015(9) -0.001(5) 0.015(9) O4' 0.086(11) 0.161(15) 0.119(13) -0.008(11) 0.028(8) -0.044(10) O5' 0.128(12) 0.085(9) 0.175(15) -0.030(9) 0.062(10) 0.009(8) Cl2 0.0510(8) 0.0584(8) 0.0548(8) -0.0111(6) 0.0017(6) 0.0004(6) O6 0.055(3) 0.158(6) 0.145(5) -0.051(4) -0.019(3) -0.004(3) O7 0.072(7) 0.063(6) 0.154(12) -0.019(7) -0.029(8) 0.006(5) O8 0.133(11) 0.116(11) 0.051(6) 0.020(6) -0.008(6) -0.005(9) O9 0.151(12) 0.115(10) 0.065(6) -0.015(7) 0.036(7) 0.031(9) O7' 0.141(13) 0.077(9) 0.25(2) 0.011(12) 0.059(15) 0.034(8) O8' 0.110(11) 0.202(19) 0.126(13) 0.070(13) 0.024(10) -0.025(12) O9' 0.076(7) 0.147(11) 0.069(7) -0.040(7) 0.005(5) -0.038(7) O4W 0.086(7) 0.055(7) 0.091(8) 0.025(5) 0.017(6) -0.004(6) O4W' 0.103(8) 0.064(8) 0.088(9) -0.004(6) 0.008(7) -0.011(7) O5W 0.203(9) 0.206(9) 0.122(6) 0.029(6) 0.002(6) -0.020(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 Co1 O1W 2.075(3) . ? Co1 O3W 2.090(3) . ? Co1 O2W 2.106(4) . ? Co1 N1 2.121(4) 2 ? Co1 N2 2.123(4) . ? Co1 O1 2.127(3) 2 ? O1 C6 1.229(5) . ? O1 Co1 2.127(3) 2_545 ? N1 C1 1.328(6) . ? N1 C5 1.359(6) . ? N1 Co1 2.121(4) 2_545 ? N2 C11 1.341(6) . ? N2 C7 1.345(6) . ? C1 C2 1.394(8) . ? C2 C3 1.365(8) . ? C3 C4 1.397(7) . ? C4 C5 1.378(7) . ? C5 C6 1.489(6) . ? C6 C8 1.475(6) . ? C7 C8 1.380(6) . ? C8 C9 1.394(6) . ? C9 C10 1.370(7) . ? C10 C11 1.372(7) . ? Cl1 O4 1.373(8) . ? Cl1 O3' 1.378(7) . ? Cl1 O2 1.408(4) . ? Cl1 O5' 1.413(7) . ? Cl1 O3 1.416(8) . ? Cl1 O5 1.422(7) . ? Cl1 O4' 1.422(8) . ? Cl2 O8 1.366(7) . ? Cl2 O8' 1.370(7) . ? Cl2 O7' 1.387(7) . ? Cl2 O7 1.398(7) . ? Cl2 O6 1.402(4) . ? Cl2 O9' 1.416(6) . ? Cl2 O9 1.421(7) . ? 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 O1W Co1 O3W 89.43(15) . . ? O1W Co1 O2W 90.58(17) . . ? O3W Co1 O2W 178.93(16) . . ? O1W Co1 N1 98.78(15) . 2 ? O3W Co1 N1 91.66(15) . 2 ? O2W Co1 N1 89.40(16) . 2 ? O1W Co1 N2 94.86(15) . . ? O3W Co1 N2 87.86(15) . . ? O2W Co1 N2 91.07(16) . . ? N1 Co1 N2 166.35(14) 2 . ? O1W Co1 O1 173.68(14) . 2 ? O3W Co1 O1 87.98(14) . 2 ? O2W Co1 O1 92.11(16) . 2 ? N1 Co1 O1 75.54(13) 2 2 ? N2 Co1 O1 90.81(13) . 2 ? C6 O1 Co1 117.6(3) . 2_545 ? C1 N1 C5 118.4(4) . . ? C1 N1 Co1 125.7(3) . 2_545 ? C5 N1 Co1 115.8(3) . 2_545 ? C11 N2 C7 116.9(4) . . ? C11 N2 Co1 125.2(3) . . ? C7 N2 Co1 117.8(3) . . ? N1 C1 C2 122.4(5) . . ? C3 C2 C1 119.1(5) . . ? C2 C3 C4 119.2(5) . . ? C5 C4 C3 118.6(5) . . ? N1 C5 C4 122.1(4) . . ? N1 C5 C6 112.7(4) . . ? C4 C5 C6 125.1(4) . . ? O1 C6 C8 118.0(4) . . ? O1 C6 C5 118.2(4) . . ? C8 C6 C5 123.8(4) . . ? N2 C7 C8 123.5(4) . . ? C7 C8 C9 118.1(4) . . ? C7 C8 C6 121.9(4) . . ? C9 C8 C6 119.8(4) . . ? C10 C9 C8 118.7(4) . . ? C9 C10 C11 119.5(5) . . ? N2 C11 C10 123.2(4) . . ? O4 Cl1 O3' 124.2(10) . . ? O4 Cl1 O2 115.2(7) . . ? O3' Cl1 O2 114.3(6) . . ? O4 Cl1 O5' 72.7(8) . . ? O3' Cl1 O5' 112.5(8) . . ? O2 Cl1 O5' 109.3(6) . . ? O4 Cl1 O3 108.0(8) . . ? O3' Cl1 O3 30.6(9) . . ? O2 Cl1 O3 108.4(8) . . ? O5' Cl1 O3 137.2(9) . . ? O4 Cl1 O5 114.1(8) . . ? O3' Cl1 O5 73.4(10) . . ? O2 Cl1 O5 106.5(6) . . ? O5' Cl1 O5 45.8(8) . . ? O3 Cl1 O5 103.9(8) . . ? O4 Cl1 O4' 32.1(8) . . ? O3' Cl1 O4' 108.8(8) . . ? O2 Cl1 O4' 106.6(7) . . ? O5' Cl1 O4' 104.7(7) . . ? O3 Cl1 O4' 82.9(10) . . ? O5 Cl1 O4' 141.9(8) . . ? O8 Cl2 O8' 127.3(8) . . ? O8 Cl2 O7' 45.1(7) . . ? O8' Cl2 O7' 112.2(9) . . ? O8 Cl2 O7 111.4(6) . . ? O8' Cl2 O7 53.5(8) . . ? O7' Cl2 O7 142.7(8) . . ? O8 Cl2 O6 116.4(6) . . ? O8' Cl2 O6 116.2(6) . . ? O7' Cl2 O6 109.0(7) . . ? O7 Cl2 O6 107.9(5) . . ? O8 Cl2 O9' 60.6(6) . . ? O8' Cl2 O9' 108.8(8) . . ? O7' Cl2 O9' 105.7(8) . . ? O7 Cl2 O9' 59.6(7) . . ? O6 Cl2 O9' 104.1(5) . . ? O8 Cl2 O9 109.5(7) . . ? O8' Cl2 O9 54.8(8) . . ? O7' Cl2 O9 68.3(8) . . ? O7 Cl2 O9 108.3(8) . . ? O6 Cl2 O9 102.8(5) . . ? O9' Cl2 O9 152.9(7) . . ? 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 O1W Co1 N2 C11 11.7(4) . . . . ? O3W Co1 N2 C11 101.0(4) . . . . ? O2W Co1 N2 C11 -79.0(4) . . . . ? N1 Co1 N2 C11 -170.8(6) 2 . . . ? O1 Co1 N2 C11 -171.1(4) 2 . . . ? O1W Co1 N2 C7 -171.7(3) . . . . ? O3W Co1 N2 C7 -82.4(3) . . . . ? O2W Co1 N2 C7 97.6(4) . . . . ? N1 Co1 N2 C7 5.8(8) 2 . . . ? O1 Co1 N2 C7 5.5(3) 2 . . . ? C5 N1 C1 C2 -0.8(8) . . . . ? Co1 N1 C1 C2 176.1(4) 2_545 . . . ? N1 C1 C2 C3 -0.5(9) . . . . ? C1 C2 C3 C4 0.0(9) . . . . ? C2 C3 C4 C5 1.7(8) . . . . ? C1 N1 C5 C4 2.7(7) . . . . ? Co1 N1 C5 C4 -174.5(4) 2_545 . . . ? C1 N1 C5 C6 179.1(4) . . . . ? Co1 N1 C5 C6 1.9(5) 2_545 . . . ? C3 C4 C5 N1 -3.1(7) . . . . ? C3 C4 C5 C6 -179.2(5) . . . . ? Co1 O1 C6 C8 -178.3(3) 2_545 . . . ? Co1 O1 C6 C5 2.8(6) 2_545 . . . ? N1 C5 C6 O1 -3.2(6) . . . . ? C4 C5 C6 O1 173.2(5) . . . . ? N1 C5 C6 C8 178.0(4) . . . . ? C4 C5 C6 C8 -5.7(7) . . . . ? C11 N2 C7 C8 1.5(7) . . . . ? Co1 N2 C7 C8 -175.4(4) . . . . ? N2 C7 C8 C9 -3.0(7) . . . . ? N2 C7 C8 C6 -178.3(4) . . . . ? O1 C6 C8 C7 140.6(5) . . . . ? C5 C6 C8 C7 -40.5(7) . . . . ? O1 C6 C8 C9 -34.6(7) . . . . ? C5 C6 C8 C9 144.3(5) . . . . ? C7 C8 C9 C10 2.3(7) . . . . ? C6 C8 C9 C10 177.7(5) . . . . ? C8 C9 C10 C11 -0.3(8) . . . . ? C7 N2 C11 C10 0.7(7) . . . . ? Co1 N2 C11 C10 177.3(4) . . . . ? C9 C10 C11 N2 -1.3(9) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.672 _refine_diff_density_min -0.581 _refine_diff_density_rms 0.087 #===END data_Compound(9) _database_code_depnum_ccdc_archive 'CCDC 278828' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H16 F6 N2 O11 S2 Zn' _chemical_formula_weight 619.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1623(5) _cell_length_b 11.5785(5) _cell_length_c 19.8500(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.0170(10) _cell_angle_gamma 90.00 _cell_volume 2318.14(18) _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 Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 1.344 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.545444 _exptl_absorpt_correction_T_max 1.000000 _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 12107 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0261 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4087 _reflns_number_gt 3625 _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^)+(0.0774P)^2^+1.8783P] 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 4087 _refine_ls_number_parameters 324 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1322 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.121 _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 0.78083(3) 0.38715(3) 0.131317(17) 0.03216(16) Uani 1 1 d . . . S1 S 0.77338(11) 0.18900(9) 0.36438(5) 0.0528(3) Uani 1 1 d . . . S2 S 0.35703(10) 0.18719(9) 0.08567(6) 0.0571(3) Uani 1 1 d D . . N1 N 1.2527(3) 0.0667(2) 0.35194(13) 0.0347(6) Uani 1 1 d . . . N2 N 0.8657(3) 0.2177(2) 0.13607(13) 0.0366(6) Uani 1 1 d . . . C1 C 1.3416(4) 0.1299(3) 0.39100(18) 0.0437(8) Uani 1 1 d . . . H1A H 1.3812 0.0986 0.4316 0.052 Uiso 1 1 calc R . . C2 C 1.3769(4) 0.2399(3) 0.3734(2) 0.0536(10) Uani 1 1 d . . . H2A H 1.4373 0.2827 0.4023 0.064 Uiso 1 1 calc R . . C3 C 1.3219(4) 0.2851(3) 0.3130(2) 0.0556(10) Uani 1 1 d . . . H3A H 1.3472 0.3578 0.2993 0.067 Uiso 1 1 calc R . . C4 C 1.2273(4) 0.2213(3) 0.27210(18) 0.0441(8) Uani 1 1 d . . . H4A H 1.1876 0.2508 0.2310 0.053 Uiso 1 1 calc R . . C5 C 1.1940(3) 0.1132(3) 0.29388(16) 0.0323(7) Uani 1 1 d . . . C6 C 1.0954(3) 0.0345(3) 0.25480(15) 0.0329(7) Uani 1 1 d . . . C7 C 0.9476(3) 0.1824(3) 0.19023(16) 0.0335(7) Uani 1 1 d . . . H7A H 0.9655 0.2326 0.2268 0.040 Uiso 1 1 calc R . . C8 C 1.0070(3) 0.0742(3) 0.19428(16) 0.0336(7) Uani 1 1 d . . . C9 C 0.9770(4) -0.0023(3) 0.14045(19) 0.0480(9) Uani 1 1 d . . . H9A H 1.0126 -0.0764 0.1422 0.058 Uiso 1 1 calc R . . C10 C 0.8934(5) 0.0341(3) 0.0847(2) 0.0584(11) Uani 1 1 d . . . H10A H 0.8722 -0.0151 0.0479 0.070 Uiso 1 1 calc R . . C11 C 0.8415(4) 0.1440(3) 0.08376(18) 0.0503(9) Uani 1 1 d . . . H11A H 0.7872 0.1683 0.0452 0.060 Uiso 1 1 calc R . . C12 C 0.7293(4) 0.0431(5) 0.3456(3) 0.0862(17) Uani 1 1 d D . . C13 C 0.4004(7) 0.0403(5) 0.1066(3) 0.0881(16) Uani 1 1 d . . . O1 O 1.0898(2) -0.06621(19) 0.27273(12) 0.0411(5) Uani 1 1 d . . . O2 O 0.7385(4) 0.2049(3) 0.43055(16) 0.0836(11) Uani 1 1 d . . . O3 O 0.9110(4) 0.1971(4) 0.35863(19) 0.0955(13) Uani 1 1 d . . . O4 O 0.6896(6) 0.2550(4) 0.3161(2) 0.1139(16) Uani 1 1 d . . . O5 O 0.3901(4) 0.2491(3) 0.1470(2) 0.0870(11) Uani 1 1 d D . . O6 O 0.4360(5) 0.2201(4) 0.03523(18) 0.1121(17) Uani 1 1 d D . . O7 O 0.2195(4) 0.1783(4) 0.0644(3) 0.139(2) Uani 1 1 d D . . O1W O 0.6406(3) 0.3707(2) 0.04615(12) 0.0457(6) Uani 1 1 d . . . H1WA H 0.6648 0.3645 0.0026 0.12(2) Uiso 1 1 d R . . H1WB H 0.5730 0.3161 0.0433 0.11(2) Uiso 1 1 d R . . O2W O 0.9147(3) 0.4391(2) 0.06719(15) 0.0595(7) Uani 1 1 d . . . H2WA H 0.9651 0.3946 0.0409 0.066(14) Uiso 1 1 d R . . H2WB H 0.9071 0.5121 0.0475 0.094(18) Uiso 1 1 d R . . O3W O 0.6356(3) 0.3448(3) 0.19189(13) 0.0520(6) Uani 1 1 d . . . H3WA H 0.6558 0.3151 0.2355 0.065(13) Uiso 1 1 d R . . H3WB H 0.5485 0.3207 0.1804 0.072(14) Uiso 1 1 d R . . O4W O 1.0674(3) 0.3348(3) -0.01762(19) 0.0721(9) Uani 1 1 d . . . H4WA H 1.0390 0.2616 -0.0005 0.052(11) Uiso 1 1 d R . . H4WB H 1.0301 0.2981 -0.0596 0.22(5) Uiso 1 1 d R . . F1 F 0.6045(3) 0.0218(3) 0.3429(3) 0.1330(17) Uani 1 1 d D . . F2 F 0.7896(5) -0.0250(4) 0.3921(4) 0.195(3) Uani 1 1 d D . . F3 F 0.7644(6) 0.0109(5) 0.2882(3) 0.229(4) Uani 1 1 d D . . F4 F 0.3764(6) -0.0306(4) 0.0575(3) 0.158(2) Uani 1 1 d . . . F5 F 0.5262(6) 0.0329(5) 0.1265(4) 0.191(3) Uani 1 1 d . . . F6 F 0.3385(7) 0.0061(4) 0.1574(3) 0.170(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.0381(2) 0.0242(2) 0.0325(2) 0.00066(13) -0.00245(15) -0.00053(13) S1 0.0719(7) 0.0497(6) 0.0360(5) 0.0074(4) 0.0035(4) -0.0140(5) S2 0.0531(6) 0.0424(5) 0.0722(7) 0.0115(5) -0.0065(5) -0.0089(4) N1 0.0402(14) 0.0278(14) 0.0348(13) -0.0009(11) -0.0008(11) -0.0022(11) N2 0.0447(15) 0.0275(14) 0.0357(14) 0.0006(11) -0.0029(11) 0.0027(12) C1 0.051(2) 0.0388(19) 0.0387(18) -0.0001(14) -0.0067(15) -0.0071(15) C2 0.058(2) 0.042(2) 0.056(2) -0.0024(17) -0.0098(18) -0.0164(18) C3 0.068(3) 0.034(2) 0.061(2) 0.0094(17) -0.0053(19) -0.0198(18) C4 0.050(2) 0.0342(18) 0.0463(19) 0.0085(15) -0.0022(15) -0.0076(15) C5 0.0353(16) 0.0281(16) 0.0333(16) 0.0003(12) 0.0031(12) 0.0012(12) C6 0.0371(16) 0.0268(16) 0.0341(15) -0.0002(12) 0.0014(12) 0.0033(13) C7 0.0412(17) 0.0237(15) 0.0339(16) -0.0012(12) -0.0018(13) -0.0010(12) C8 0.0384(16) 0.0258(15) 0.0354(16) 0.0013(13) -0.0009(13) -0.0007(13) C9 0.062(2) 0.0283(17) 0.051(2) -0.0070(15) -0.0081(17) 0.0079(16) C10 0.082(3) 0.038(2) 0.047(2) -0.0144(17) -0.0214(19) 0.0109(19) C11 0.066(2) 0.0362(19) 0.0424(19) -0.0037(15) -0.0171(17) 0.0079(17) C12 0.054(3) 0.056(3) 0.149(5) -0.026(3) 0.016(3) -0.002(2) C13 0.103(4) 0.055(3) 0.103(4) 0.004(3) 0.000(3) 0.010(3) O1 0.0492(13) 0.0238(12) 0.0461(13) 0.0040(10) -0.0109(10) -0.0010(10) O2 0.112(3) 0.089(3) 0.0517(18) 0.0029(17) 0.0163(18) -0.012(2) O3 0.083(2) 0.123(4) 0.082(2) -0.015(2) 0.0174(19) -0.048(2) O4 0.173(5) 0.088(3) 0.074(2) 0.038(2) -0.010(3) 0.008(3) O5 0.090(3) 0.074(2) 0.103(3) -0.017(2) 0.034(2) -0.0155(19) O6 0.145(4) 0.125(4) 0.064(2) 0.006(2) 0.005(2) -0.073(3) O7 0.069(3) 0.088(3) 0.243(6) 0.044(4) -0.050(3) -0.017(2) O1W 0.0506(14) 0.0507(15) 0.0334(12) -0.0007(10) -0.0043(10) -0.0049(12) O2W 0.0701(18) 0.0397(15) 0.0752(19) 0.0013(14) 0.0345(15) -0.0055(13) O3W 0.0504(15) 0.0629(17) 0.0426(14) 0.0123(12) 0.0055(11) -0.0076(13) O4W 0.072(2) 0.058(2) 0.086(2) -0.0004(17) 0.0110(17) 0.0096(16) F1 0.066(2) 0.087(3) 0.246(5) -0.029(3) 0.021(3) -0.0283(18) F2 0.148(4) 0.053(2) 0.365(9) 0.030(4) -0.053(5) 0.005(2) F3 0.198(5) 0.215(6) 0.300(8) -0.207(7) 0.137(6) -0.104(5) F4 0.205(5) 0.071(3) 0.197(5) -0.049(3) 0.025(4) -0.011(3) F5 0.140(4) 0.125(4) 0.289(7) 0.014(4) -0.050(4) 0.071(3) F6 0.266(7) 0.083(3) 0.172(4) 0.058(3) 0.076(5) -0.013(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 O2W 2.063(3) . ? Zn1 O3W 2.073(3) . ? Zn1 O1W 2.082(2) . ? Zn1 N1 2.139(3) 2_755 ? Zn1 N2 2.141(3) . ? Zn1 O1 2.244(2) 2_755 ? S1 O2 1.414(3) . ? S1 O3 1.420(4) . ? S1 O4 1.424(4) . ? S1 C12 1.776(5) . ? S2 O6 1.410(4) . ? S2 O7 1.414(4) . ? S2 O5 1.417(4) . ? S2 C13 1.793(6) . ? N1 C1 1.335(4) . ? N1 C5 1.344(4) . ? N1 Zn1 2.139(3) 2_745 ? N2 C7 1.340(4) . ? N2 C11 1.343(4) . ? C1 C2 1.380(5) . ? C2 C3 1.363(6) . ? C3 C4 1.392(5) . ? C4 C5 1.379(5) . ? C5 C6 1.499(4) . ? C6 O1 1.222(4) . ? C6 C8 1.483(4) . ? C7 C8 1.389(4) . ? C8 C9 1.393(5) . ? C9 C10 1.376(5) . ? C10 C11 1.377(5) . ? C12 F1 1.287(5) . ? C12 F3 1.289(5) . ? C12 F2 1.308(6) . ? C13 F4 1.274(7) . ? C13 F5 1.293(8) . ? C13 F6 1.313(8) . ? O1 Zn1 2.244(2) 2_745 ? 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 O2W Zn1 O3W 175.30(11) . . ? O2W Zn1 O1W 87.90(11) . . ? O3W Zn1 O1W 89.09(10) . . ? O2W Zn1 N1 86.68(11) . 2_755 ? O3W Zn1 N1 90.07(11) . 2_755 ? O1W Zn1 N1 96.24(10) . 2_755 ? O2W Zn1 N2 90.11(11) . . ? O3W Zn1 N2 93.98(11) . . ? O1W Zn1 N2 100.62(10) . . ? N1 Zn1 N2 162.72(10) 2_755 . ? O2W Zn1 O1 95.23(11) . 2_755 ? O3W Zn1 O1 87.11(10) . 2_755 ? O1W Zn1 O1 169.38(9) . 2_755 ? N1 Zn1 O1 73.87(9) 2_755 2_755 ? N2 Zn1 O1 89.54(9) . 2_755 ? O2 S1 O3 115.3(2) . . ? O2 S1 O4 111.0(3) . . ? O3 S1 O4 115.1(3) . . ? O2 S1 C12 103.5(2) . . ? O3 S1 C12 105.8(2) . . ? O4 S1 C12 104.8(3) . . ? O6 S2 O7 115.8(3) . . ? O6 S2 O5 112.2(2) . . ? O7 S2 O5 114.6(3) . . ? O6 S2 C13 106.0(3) . . ? O7 S2 C13 101.9(3) . . ? O5 S2 C13 104.7(3) . . ? C1 N1 C5 118.4(3) . . ? C1 N1 Zn1 123.5(2) . 2_745 ? C5 N1 Zn1 117.4(2) . 2_745 ? C7 N2 C11 117.6(3) . . ? C7 N2 Zn1 121.5(2) . . ? C11 N2 Zn1 120.9(2) . . ? N1 C1 C2 122.5(3) . . ? C3 C2 C1 119.0(3) . . ? C2 C3 C4 119.3(3) . . ? C5 C4 C3 118.5(3) . . ? N1 C5 C4 122.2(3) . . ? N1 C5 C6 113.5(3) . . ? C4 C5 C6 124.3(3) . . ? O1 C6 C8 119.1(3) . . ? O1 C6 C5 118.8(3) . . ? C8 C6 C5 122.1(3) . . ? N2 C7 C8 123.0(3) . . ? C7 C8 C9 118.5(3) . . ? C7 C8 C6 122.9(3) . . ? C9 C8 C6 118.6(3) . . ? C10 C9 C8 118.5(3) . . ? C9 C10 C11 119.5(3) . . ? N2 C11 C10 122.9(3) . . ? F1 C12 F3 106.6(5) . . ? F1 C12 F2 106.8(5) . . ? F3 C12 F2 107.0(5) . . ? F1 C12 S1 114.4(4) . . ? F3 C12 S1 111.8(4) . . ? F2 C12 S1 109.9(4) . . ? F4 C13 F5 106.3(6) . . ? F4 C13 F6 109.1(6) . . ? F5 C13 F6 107.1(6) . . ? F4 C13 S2 114.5(5) . . ? F5 C13 S2 109.9(5) . . ? F6 C13 S2 109.7(5) . . ? C6 O1 Zn1 115.7(2) . 2_745 ? 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 O2W Zn1 N2 C7 102.9(3) . . . . ? O3W Zn1 N2 C7 -79.4(3) . . . . ? O1W Zn1 N2 C7 -169.2(2) . . . . ? N1 Zn1 N2 C7 23.8(5) 2_755 . . . ? O1 Zn1 N2 C7 7.7(3) 2_755 . . . ? O2W Zn1 N2 C11 -75.1(3) . . . . ? O3W Zn1 N2 C11 102.6(3) . . . . ? O1W Zn1 N2 C11 12.7(3) . . . . ? N1 Zn1 N2 C11 -154.3(3) 2_755 . . . ? O1 Zn1 N2 C11 -170.4(3) 2_755 . . . ? C5 N1 C1 C2 -1.2(6) . . . . ? Zn1 N1 C1 C2 169.4(3) 2_745 . . . ? N1 C1 C2 C3 -1.8(7) . . . . ? C1 C2 C3 C4 2.8(7) . . . . ? C2 C3 C4 C5 -0.9(6) . . . . ? C1 N1 C5 C4 3.2(5) . . . . ? Zn1 N1 C5 C4 -167.9(3) 2_745 . . . ? C1 N1 C5 C6 -179.5(3) . . . . ? Zn1 N1 C5 C6 9.4(3) 2_745 . . . ? C3 C4 C5 N1 -2.2(5) . . . . ? C3 C4 C5 C6 -179.2(3) . . . . ? N1 C5 C6 O1 -9.7(4) . . . . ? C4 C5 C6 O1 167.6(3) . . . . ? N1 C5 C6 C8 171.8(3) . . . . ? C4 C5 C6 C8 -11.0(5) . . . . ? C11 N2 C7 C8 -0.2(5) . . . . ? Zn1 N2 C7 C8 -178.3(2) . . . . ? N2 C7 C8 C9 -2.0(5) . . . . ? N2 C7 C8 C6 -178.8(3) . . . . ? O1 C6 C8 C7 141.9(3) . . . . ? C5 C6 C8 C7 -39.5(5) . . . . ? O1 C6 C8 C9 -34.8(5) . . . . ? C5 C6 C8 C9 143.7(3) . . . . ? C7 C8 C9 C10 2.2(6) . . . . ? C6 C8 C9 C10 179.1(4) . . . . ? C8 C9 C10 C11 -0.4(7) . . . . ? C7 N2 C11 C10 2.1(6) . . . . ? Zn1 N2 C11 C10 -179.7(3) . . . . ? C9 C10 C11 N2 -1.8(7) . . . . ? O2 S1 C12 F1 63.8(5) . . . . ? O3 S1 C12 F1 -174.5(4) . . . . ? O4 S1 C12 F1 -52.5(5) . . . . ? O2 S1 C12 F3 -174.9(4) . . . . ? O3 S1 C12 F3 -53.3(5) . . . . ? O4 S1 C12 F3 68.7(5) . . . . ? O2 S1 C12 F2 -56.2(4) . . . . ? O3 S1 C12 F2 65.4(4) . . . . ? O4 S1 C12 F2 -172.6(4) . . . . ? O6 S2 C13 F4 -62.0(6) . . . . ? O7 S2 C13 F4 59.5(7) . . . . ? O5 S2 C13 F4 179.2(5) . . . . ? O6 S2 C13 F5 57.5(6) . . . . ? O7 S2 C13 F5 179.0(6) . . . . ? O5 S2 C13 F5 -61.3(6) . . . . ? O6 S2 C13 F6 175.0(5) . . . . ? O7 S2 C13 F6 -63.5(6) . . . . ? O5 S2 C13 F6 56.2(6) . . . . ? C8 C6 O1 Zn1 -176.3(2) . . . 2_745 ? C5 C6 O1 Zn1 5.1(4) . . . 2_745 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.638 _refine_diff_density_min -0.849 _refine_diff_density_rms 0.091 #===END