# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name P.Bharadwaj E.S.S.Iyer D.Ray _publ_contact_author_name 'P. K. Bharadwaj' _publ_contact_author_email pkb@iitk.ac.in data_1 _database_code_depnum_ccdc_archive 'CCDC 676701' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 Ag F3 N3 O5 S' _chemical_formula_sum 'C15 H22 Ag F3 N3 O5 S' _chemical_formula_weight 521.29 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' Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.762(5) _cell_length_b 10.555(5) _cell_length_c 12.204(5) _cell_angle_alpha 100.934(5) _cell_angle_beta 100.595(5) _cell_angle_gamma 107.276(5) _cell_volume 1022.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 999 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 28.23 _exptl_crystal_description rectangular _exptl_crystal_colour red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.693 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 1.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8562 _exptl_absorpt_correction_T_max 0.9040 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6843 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.33 _reflns_number_total 4883 _reflns_number_gt 3982 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material SHELXL-97 _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^)+(0.0525P)^2^+15.1244P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4883 _refine_ls_number_parameters 253 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0959 _refine_ls_R_factor_gt 0.0650 _refine_ls_wR_factor_ref 0.2081 _refine_ls_wR_factor_gt 0.1414 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.127 _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 0.80379(7) 0.54388(7) -0.17924(5) 0.02600(19) Uani 1 1 d . . . S1 S 0.2612(2) -0.2037(2) -0.37461(18) 0.0294(4) Uani 1 1 d . . . F1 F 0.3004(10) 0.0488(7) -0.2763(7) 0.076(2) Uani 1 1 d . . . F2 F 0.1494(9) -0.0264(9) -0.4511(9) 0.088(3) Uani 1 1 d . . . F3 F 0.4118(8) 0.0290(6) -0.4149(6) 0.0537(16) Uani 1 1 d . . . O1 O 0.5277(7) 0.4253(7) -0.2763(5) 0.0350(14) Uani 1 1 d . . . O2 O 0.4119(9) -0.1878(8) -0.2960(7) 0.054(2) Uani 1 1 d . . . O3 O 0.1129(8) -0.2468(7) -0.3353(6) 0.0447(17) Uani 1 1 d . . . O4 O 0.2430(9) -0.2719(8) -0.4921(6) 0.0504(19) Uani 1 1 d . . . N1 N 0.9148(7) 0.4802(6) -0.0238(6) 0.0228(13) Uani 1 1 d . . . N2 N -0.1538(8) 0.1299(7) -0.0496(6) 0.0268(14) Uani 1 1 d . . . N3 N 0.3281(8) 0.3257(8) -0.4452(6) 0.0308(15) Uani 1 1 d . . . C1 C 0.8216(9) 0.4302(7) 0.0382(7) 0.0214(14) Uani 1 1 d . . . H1 H 0.8703 0.4245 0.1107 0.026 Uiso 1 1 calc R . . C2 C 0.6462(9) 0.3831(8) -0.0001(7) 0.0248(16) Uani 1 1 d D . . H2 H 0.5984 0.3845 -0.0743 0.030 Uiso 1 1 calc RD . . C3 C 0.5448(8) 0.3361(7) 0.0664(6) 0.0179(13) Uani 1 1 d . . . H3 H 0.5961 0.3366 0.1404 0.021 Uiso 1 1 calc RD . . C4 C 0.3665(9) 0.2855(7) 0.0347(6) 0.0197(14) Uani 1 1 d D . . C9 C 0.2823(10) 0.2448(8) 0.1169(7) 0.0254(15) Uani 1 1 d . . . H9 H 0.3423 0.2505 0.1900 0.030 Uiso 1 1 calc R . . C8 C 0.1118(9) 0.1968(7) 0.0903(6) 0.0210(14) Uani 1 1 d . . . H8 H 0.0594 0.1757 0.1476 0.025 Uiso 1 1 calc R . . C7 C 0.0132(9) 0.1783(7) -0.0227(7) 0.0225(15) Uani 1 1 d . . . C6 C 0.1028(9) 0.2165(8) -0.1038(6) 0.0240(15) Uani 1 1 d . . . H6 H 0.0446 0.2052 -0.1790 0.029 Uiso 1 1 calc R . . C5 C 0.2712(9) 0.2692(7) -0.0758(6) 0.0204(14) Uani 1 1 d . . . H5 H 0.3241 0.2951 -0.1316 0.025 Uiso 1 1 calc R . . C10 C -0.2407(9) 0.0863(8) 0.0348(8) 0.0268(16) Uani 1 1 d . . . H10A H -0.3578 0.0554 0.0016 0.040 Uiso 1 1 calc R . . H10B H -0.2107 0.1622 0.1015 0.040 Uiso 1 1 calc R . . H10C H -0.2110 0.0127 0.0572 0.040 Uiso 1 1 calc R . . C11 C -0.2500(10) 0.1062(9) -0.1671(8) 0.035(2) Uani 1 1 d . . . H11A H -0.3657 0.0722 -0.1705 0.053 Uiso 1 1 calc R . . H11B H -0.2235 0.0399 -0.2186 0.053 Uiso 1 1 calc R . . H11C H -0.2241 0.1909 -0.1895 0.053 Uiso 1 1 calc R . . C12 C 0.4816(10) 0.3606(9) -0.3803(7) 0.0308(18) Uani 1 1 d D . . H12 H 0.5586 0.3355 -0.4143 0.037 Uiso 1 1 calc RD . . C13 C 0.2000(11) 0.3618(12) -0.3975(8) 0.044(3) Uani 1 1 d . . . H13A H 0.0982 0.3285 -0.4567 0.066 Uiso 1 1 calc R . . H13B H 0.2338 0.4599 -0.3699 0.066 Uiso 1 1 calc R . . H13C H 0.1844 0.3207 -0.3349 0.066 Uiso 1 1 calc R . . C14 C 0.2815(12) 0.2524(11) -0.5670(7) 0.042(2) Uani 1 1 d . . . H14A H 0.1669 0.2365 -0.5993 0.063 Uiso 1 1 calc R . . H14B H 0.2992 0.1660 -0.5744 0.063 Uiso 1 1 calc R . . H14C H 0.3478 0.3065 -0.6074 0.063 Uiso 1 1 calc R . . C15 C 0.2825(12) -0.0279(11) -0.3797(9) 0.042(2) Uani 1 1 d . . . OW1 O 0.9295(9) 0.4978(7) -0.3272(6) 0.0487(18) Uani 1 1 d . . . H1W1 H 0.9048 0.5334 -0.3787 0.058 Uiso 1 1 d . . . H2W1 H 0.9817 0.5723 -0.2807 0.058 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ag1 0.0185(3) 0.0331(3) 0.0238(3) 0.0059(2) 0.0041(2) 0.0069(2) S1 0.0201(9) 0.0295(10) 0.0324(10) 0.0012(8) 0.0050(8) 0.0050(8) F1 0.089(6) 0.041(4) 0.093(6) -0.011(4) 0.057(5) 0.013(4) F2 0.046(4) 0.079(6) 0.149(8) 0.060(6) 0.004(5) 0.030(4) F3 0.055(4) 0.044(4) 0.069(4) 0.027(3) 0.028(3) 0.013(3) O1 0.021(3) 0.044(4) 0.028(3) -0.003(3) 0.004(2) 0.004(3) O2 0.037(4) 0.057(5) 0.056(5) 0.028(4) -0.010(3) 0.005(3) O3 0.037(4) 0.045(4) 0.042(4) 0.002(3) 0.019(3) 0.000(3) O4 0.039(4) 0.051(4) 0.045(4) -0.013(3) 0.023(3) 0.001(3) N1 0.020(3) 0.016(3) 0.037(4) 0.006(3) 0.014(3) 0.009(2) N2 0.020(3) 0.028(4) 0.034(4) 0.011(3) 0.010(3) 0.006(3) N3 0.019(3) 0.040(4) 0.030(4) 0.001(3) 0.003(3) 0.014(3) C1 0.022(3) 0.015(3) 0.031(4) 0.010(3) 0.012(3) 0.005(3) C2 0.018(3) 0.017(4) 0.035(4) 0.005(3) -0.003(3) 0.006(3) C3 0.014(3) 0.017(3) 0.022(3) 0.005(3) 0.006(3) 0.004(3) C4 0.017(3) 0.019(3) 0.019(3) 0.004(3) 0.002(3) 0.003(3) C9 0.028(4) 0.021(4) 0.030(4) 0.011(3) 0.007(3) 0.008(3) C8 0.026(4) 0.018(3) 0.024(4) 0.008(3) 0.011(3) 0.011(3) C7 0.021(4) 0.015(3) 0.034(4) 0.005(3) 0.013(3) 0.008(3) C6 0.024(4) 0.022(4) 0.018(3) -0.002(3) -0.002(3) 0.006(3) C5 0.016(3) 0.021(4) 0.022(3) 0.000(3) 0.009(3) 0.005(3) C10 0.014(3) 0.022(4) 0.046(5) 0.012(3) 0.013(3) 0.002(3) C11 0.020(4) 0.033(5) 0.038(5) -0.007(4) -0.007(3) 0.005(3) C12 0.025(4) 0.031(4) 0.030(4) 0.001(3) 0.005(3) 0.007(3) C13 0.022(4) 0.080(8) 0.024(4) 0.002(4) 0.002(3) 0.019(5) C14 0.032(5) 0.063(7) 0.026(4) -0.006(4) 0.007(4) 0.021(5) C15 0.027(5) 0.044(6) 0.055(6) 0.010(5) 0.014(4) 0.012(4) OW1 0.051(4) 0.042(4) 0.046(4) 0.001(3) 0.022(3) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ag1 N1 2.278(7) . ? Ag1 O1 2.326(6) . ? Ag1 OW1 2.330(7) . ? Ag1 C8 2.568(7) 2_665 ? Ag1 C9 2.586(8) 2_665 ? S1 O2 1.425(7) . ? S1 O4 1.434(7) . ? S1 O3 1.444(7) . ? S1 C15 1.823(11) . ? F1 C15 1.318(12) . ? F2 C15 1.327(12) . ? F3 C15 1.305(11) . ? O1 C12 1.249(10) . ? N1 C1 1.281(9) . ? N1 N1 1.400(12) 2_765 ? N2 C7 1.351(10) . ? N2 C10 1.454(10) . ? N2 C11 1.456(11) . ? N3 C12 1.332(10) . ? N3 C14 1.458(11) . ? N3 C13 1.467(11) . ? C1 C2 1.422(10) . ? C2 C3 1.360(10) . ? C3 C4 1.442(9) . ? C4 C5 1.399(10) . ? C4 C9 1.408(10) . ? C9 C8 1.379(11) . ? C9 Ag1 2.586(8) 2_665 ? C8 C7 1.431(11) . ? C8 Ag1 2.568(7) 2_665 ? C7 C6 1.417(11) . ? C6 C5 1.363(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Ag1 O1 118.5(2) . . ? N1 Ag1 OW1 109.6(3) . . ? O1 Ag1 OW1 100.2(2) . . ? N1 Ag1 C8 99.9(2) . 2_665 ? O1 Ag1 C8 117.3(2) . 2_665 ? OW1 Ag1 C8 111.6(2) . 2_665 ? N1 Ag1 C9 111.5(2) . 2_665 ? O1 Ag1 C9 87.1(2) . 2_665 ? OW1 Ag1 C9 127.9(3) . 2_665 ? C8 Ag1 C9 31.0(2) 2_665 2_665 ? O2 S1 O4 115.0(5) . . ? O2 S1 O3 116.2(5) . . ? O4 S1 O3 113.9(4) . . ? O2 S1 C15 103.2(5) . . ? O4 S1 C15 103.4(5) . . ? O3 S1 C15 102.7(4) . . ? C12 O1 Ag1 123.1(5) . . ? C1 N1 N1 116.0(8) . 2_765 ? C1 N1 Ag1 119.1(5) . . ? N1 N1 Ag1 123.3(6) 2_765 . ? C7 N2 C10 120.5(7) . . ? C7 N2 C11 120.7(7) . . ? C10 N2 C11 118.5(7) . . ? C12 N3 C14 121.3(7) . . ? C12 N3 C13 121.3(7) . . ? C14 N3 C13 117.3(7) . . ? N1 C1 C2 122.2(7) . . ? C3 C2 C1 123.3(7) . . ? C2 C3 C4 127.1(7) . . ? C5 C4 C9 117.6(7) . . ? C5 C4 C3 123.4(7) . . ? C9 C4 C3 119.0(6) . . ? C8 C9 C4 120.8(7) . . ? C8 C9 Ag1 73.7(4) . 2_665 ? C4 C9 Ag1 100.1(5) . 2_665 ? C9 C8 C7 121.9(7) . . ? C9 C8 Ag1 75.2(4) . 2_665 ? C7 C8 Ag1 102.7(4) . 2_665 ? N2 C7 C6 122.4(7) . . ? N2 C7 C8 122.3(7) . . ? C6 C7 C8 115.3(7) . . ? C5 C6 C7 122.4(7) . . ? C6 C5 C4 121.8(7) . . ? O1 C12 N3 123.5(8) . . ? F3 C15 F1 107.2(9) . . ? F3 C15 F2 108.3(9) . . ? F1 C15 F2 108.8(9) . . ? F3 C15 S1 111.7(7) . . ? F1 C15 S1 110.6(8) . . ? F2 C15 S1 110.1(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 N1 Ag1 O1 C12 -119.5(7) . . . . ? OW1 Ag1 O1 C12 -0.5(8) . . . . ? C8 Ag1 O1 C12 120.5(7) 2_665 . . . ? C9 Ag1 O1 C12 127.5(7) 2_665 . . . ? O1 Ag1 N1 C1 -30.6(6) . . . . ? OW1 Ag1 N1 C1 -144.6(6) . . . . ? C8 Ag1 N1 C1 98.1(6) 2_665 . . . ? C9 Ag1 N1 C1 68.1(6) 2_665 . . . ? O1 Ag1 N1 N1 164.1(6) . . . 2_765 ? OW1 Ag1 N1 N1 50.1(8) . . . 2_765 ? C8 Ag1 N1 N1 -67.2(7) 2_665 . . 2_765 ? C9 Ag1 N1 N1 -97.2(7) 2_665 . . 2_765 ? N1 N1 C1 C2 -178.7(7) 2_765 . . . ? Ag1 N1 C1 C2 15.0(10) . . . . ? N1 C1 C2 C3 -176.6(7) . . . . ? C1 C2 C3 C4 -179.5(7) . . . . ? C2 C3 C4 C5 4.6(12) . . . . ? C2 C3 C4 C9 -178.1(7) . . . . ? C5 C4 C9 C8 -2.9(11) . . . . ? C3 C4 C9 C8 179.5(7) . . . . ? C5 C4 C9 Ag1 -79.9(7) . . . 2_665 ? C3 C4 C9 Ag1 102.5(6) . . . 2_665 ? C4 C9 C8 C7 3.7(11) . . . . ? Ag1 C9 C8 C7 95.9(7) 2_665 . . . ? C4 C9 C8 Ag1 -92.2(7) . . . 2_665 ? C10 N2 C7 C6 177.3(7) . . . . ? C11 N2 C7 C6 4.0(11) . . . . ? C10 N2 C7 C8 -3.7(11) . . . . ? C11 N2 C7 C8 -177.0(7) . . . . ? C9 C8 C7 N2 179.3(7) . . . . ? Ag1 C8 C7 N2 -100.4(7) 2_665 . . . ? C9 C8 C7 C6 -1.7(10) . . . . ? Ag1 C8 C7 C6 78.6(6) 2_665 . . . ? N2 C7 C6 C5 178.0(7) . . . . ? C8 C7 C6 C5 -1.0(11) . . . . ? C7 C6 C5 C4 1.8(12) . . . . ? C9 C4 C5 C6 0.2(11) . . . . ? C3 C4 C5 C6 177.6(7) . . . . ? Ag1 O1 C12 N3 -160.4(7) . . . . ? C14 N3 C12 O1 178.8(9) . . . . ? C13 N3 C12 O1 0.0(14) . . . . ? O2 S1 C15 F3 59.3(9) . . . . ? O4 S1 C15 F3 -60.8(8) . . . . ? O3 S1 C15 F3 -179.5(7) . . . . ? O2 S1 C15 F1 -60.0(8) . . . . ? O4 S1 C15 F1 179.9(7) . . . . ? O3 S1 C15 F1 61.2(8) . . . . ? O2 S1 C15 F2 179.7(8) . . . . ? O4 S1 C15 F2 59.6(8) . . . . ? O3 S1 C15 F2 -59.1(9) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.280 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.273 data_LLHPF6 _database_code_depnum_ccdc_archive 'CCDC 676702' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C18 H23 N4) 2(F6 P) C2 O' _chemical_formula_sum 'C38 H46 F12 N8 O1 P2' _chemical_formula_weight 920.77 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.634(5) _cell_length_b 11.077(5) _cell_length_c 11.728(5) _cell_angle_alpha 64.345(5) _cell_angle_beta 79.578(5) _cell_angle_gamma 66.542(5) _cell_volume 1034.9(8) _cell_formula_units_Z 1 _cell_measurement_temperature 100 _cell_measurement_reflns_used 999 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 28.23 _exptl_crystal_description rectangular _exptl_crystal_colour 'orange red' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9645 _exptl_absorpt_correction_T_max 0.9781 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6919 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0867 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4928 _reflns_number_gt 2640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material SHELXL-97 _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^)+(0.1617P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4928 _refine_ls_number_parameters 284 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1465 _refine_ls_R_factor_gt 0.0813 _refine_ls_wR_factor_ref 0.3057 _refine_ls_wR_factor_gt 0.2122 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.64008(13) 0.99160(12) 0.27830(11) 0.0284(3) Uani 1 1 d . . . N1 N -0.2345(4) 1.5648(4) 0.0628(3) 0.0256(8) Uani 1 1 d . . . N2 N 0.1855(4) 0.9328(4) 0.4250(3) 0.0263(8) Uani 1 1 d . . . N3 N 0.3047(4) 0.8228(4) 0.5003(3) 0.0259(8) Uani 1 1 d . . . N4 N 0.7666(4) 0.1893(4) 0.8359(4) 0.0299(9) Uani 1 1 d . . . F1 F 0.4907(3) 1.0337(3) 0.2082(3) 0.0421(7) Uani 1 1 d . . . F2 F 0.7251(3) 0.8665(3) 0.2299(3) 0.0408(7) Uani 1 1 d . . . F3 F 0.5858(3) 0.8821(3) 0.4031(3) 0.0418(7) Uani 1 1 d . . . F4 F 0.7887(3) 0.9483(3) 0.3510(2) 0.0393(7) Uani 1 1 d . . . F5 F 0.5535(3) 1.1165(3) 0.3291(3) 0.0476(8) Uani 1 1 d . . . F6 F 0.6944(3) 1.1011(3) 0.1557(3) 0.0459(8) Uani 1 1 d . . . C1 C -0.3584(5) 1.5602(5) 0.0114(4) 0.0340(11) Uani 1 1 d . . . H1A H -0.4201 1.6560 -0.0410 0.051 Uiso 1 1 calc R . . H1B H -0.4188 1.5178 0.0795 0.051 Uiso 1 1 calc R . . H1C H -0.3179 1.5038 -0.0383 0.051 Uiso 1 1 calc R . . C2 C -0.2251(5) 1.7038(4) 0.0286(4) 0.0309(10) Uani 1 1 d . . . H2A H -0.3071 1.7774 -0.0265 0.046 Uiso 1 1 calc R . . H2B H -0.1306 1.7057 -0.0140 0.046 Uiso 1 1 calc R . . H2C H -0.2315 1.7202 0.1036 0.046 Uiso 1 1 calc R . . C3 C -0.1318(5) 1.4434(4) 0.1401(4) 0.0229(9) Uani 1 1 d . . . C4 C -0.1421(5) 1.3058(4) 0.1789(4) 0.0239(9) Uani 1 1 d . . . H4 H -0.2218 1.3000 0.1497 0.029 Uiso 1 1 calc R . . C5 C -0.0396(5) 1.1839(4) 0.2567(4) 0.0246(9) Uani 1 1 d . . . H5 H -0.0503 1.0966 0.2791 0.030 Uiso 1 1 calc R . . C6 C 0.0827(5) 1.1861(4) 0.3045(4) 0.0246(9) Uani 1 1 d . . . C7 C 0.0955(5) 1.3204(5) 0.2659(4) 0.0284(10) Uani 1 1 d . . . H7 H 0.1766 1.3254 0.2941 0.034 Uiso 1 1 calc R . . C8 C -0.0087(5) 1.4441(5) 0.1877(4) 0.0282(10) Uani 1 1 d . . . H8 H 0.0025 1.5312 0.1655 0.034 Uiso 1 1 calc R . . C9 C 0.1941(5) 1.0577(5) 0.3867(4) 0.0268(9) Uani 1 1 d . . . H9 H 0.2747 1.0651 0.4130 0.032 Uiso 1 1 calc R . . C10 C 0.3092(5) 0.6900(5) 0.5479(4) 0.0272(10) Uani 1 1 d . . . H10 H 0.2271 0.6755 0.5322 0.033 Uiso 1 1 calc R . . C11 C 0.4276(5) 0.5675(4) 0.6206(4) 0.0251(9) Uani 1 1 d . . . C12 C 0.4127(5) 0.4330(4) 0.6661(4) 0.0256(9) Uani 1 1 d . . . H12 H 0.3255 0.4279 0.6481 0.031 Uiso 1 1 calc R . . C13 C 0.5251(5) 0.3082(5) 0.7370(4) 0.0277(10) Uani 1 1 d . . . H13 H 0.5124 0.2207 0.7654 0.033 Uiso 1 1 calc R . . C14 C 0.6563(5) 0.3115(4) 0.7663(4) 0.0235(9) Uani 1 1 d . . . C15 C 0.6721(5) 0.4463(5) 0.7199(4) 0.0308(10) Uani 1 1 d . . . H15 H 0.7600 0.4512 0.7366 0.037 Uiso 1 1 calc R . . C16 C 0.5605(5) 0.5694(5) 0.6509(4) 0.0276(10) Uani 1 1 d . . . H16 H 0.5731 0.6568 0.6234 0.033 Uiso 1 1 calc R . . C17 C 0.7437(5) 0.0533(5) 0.8919(4) 0.0327(11) Uani 1 1 d . . . H17A H 0.8324 -0.0213 0.9378 0.049 Uiso 1 1 calc R . . H17B H 0.7254 0.0317 0.8263 0.049 Uiso 1 1 calc R . . H17C H 0.6582 0.0594 0.9486 0.049 Uiso 1 1 calc R . . C2S C 1.0491(6) 0.4220(5) 0.5415(5) 0.0406(12) Uani 1 1 d . . . O2S O 0.9714(8) 0.3281(8) 0.5548(6) 0.0424(17) Uani 0.50 1 d P . . C18 C 0.9069(5) 0.1881(5) 0.8652(5) 0.0390(12) Uani 1 1 d . . . H18A H 0.9687 0.0915 0.9156 0.058 Uiso 1 1 calc R . . H18B H 0.8853 0.2471 0.9114 0.058 Uiso 1 1 calc R . . H18C H 0.9596 0.2249 0.7881 0.058 Uiso 1 1 calc R . . HN3 H 0.381(6) 0.830(6) 0.513(5) 0.044(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0335(7) 0.0275(7) 0.0292(6) -0.0129(5) 0.0018(5) -0.0149(5) N1 0.029(2) 0.0170(17) 0.0284(19) -0.0065(15) -0.0011(15) -0.0083(15) N2 0.029(2) 0.0199(18) 0.0215(18) -0.0040(15) 0.0001(15) -0.0056(15) N3 0.024(2) 0.026(2) 0.0244(19) -0.0073(16) -0.0018(15) -0.0086(16) N4 0.032(2) 0.0234(19) 0.034(2) -0.0081(17) -0.0048(17) -0.0112(16) F1 0.0409(16) 0.0406(17) 0.0472(17) -0.0154(14) -0.0110(13) -0.0149(14) F2 0.0424(17) 0.0407(17) 0.0490(17) -0.0286(14) 0.0054(13) -0.0150(13) F3 0.0415(16) 0.0423(17) 0.0435(16) -0.0160(14) 0.0096(13) -0.0225(14) F4 0.0387(16) 0.0486(18) 0.0389(16) -0.0174(14) -0.0012(13) -0.0235(14) F5 0.060(2) 0.0394(17) 0.0516(18) -0.0288(15) -0.0003(15) -0.0139(15) F6 0.063(2) 0.0460(18) 0.0368(16) -0.0117(14) 0.0037(14) -0.0344(16) C1 0.035(3) 0.031(3) 0.036(3) -0.012(2) -0.003(2) -0.012(2) C2 0.038(3) 0.020(2) 0.033(2) -0.0081(19) 0.005(2) -0.0134(19) C3 0.031(2) 0.020(2) 0.0187(19) -0.0070(17) 0.0078(17) -0.0137(18) C4 0.025(2) 0.023(2) 0.026(2) -0.0110(18) 0.0026(17) -0.0109(18) C5 0.028(2) 0.020(2) 0.027(2) -0.0084(18) 0.0030(18) -0.0128(18) C6 0.029(2) 0.017(2) 0.025(2) -0.0086(17) 0.0057(18) -0.0088(17) C7 0.032(2) 0.028(2) 0.031(2) -0.015(2) -0.0002(19) -0.0118(19) C8 0.036(2) 0.022(2) 0.030(2) -0.0109(19) 0.0011(19) -0.0138(19) C9 0.029(2) 0.025(2) 0.026(2) -0.0115(18) 0.0030(18) -0.0096(19) C10 0.028(2) 0.025(2) 0.029(2) -0.0114(19) 0.0037(18) -0.0104(18) C11 0.028(2) 0.024(2) 0.027(2) -0.0129(18) 0.0042(18) -0.0118(18) C12 0.028(2) 0.023(2) 0.029(2) -0.0110(19) 0.0032(18) -0.0137(18) C13 0.033(2) 0.023(2) 0.029(2) -0.0082(18) 0.0017(19) -0.0151(19) C14 0.029(2) 0.019(2) 0.023(2) -0.0088(17) 0.0023(17) -0.0106(18) C15 0.031(2) 0.027(2) 0.037(3) -0.013(2) -0.005(2) -0.011(2) C16 0.031(2) 0.021(2) 0.029(2) -0.0057(18) 0.0029(19) -0.0136(19) C17 0.042(3) 0.018(2) 0.032(2) -0.0052(19) -0.005(2) -0.0070(19) C2S 0.046(3) 0.036(3) 0.041(3) -0.011(2) 0.001(2) -0.020(2) O2S 0.040(4) 0.055(5) 0.039(4) -0.021(4) 0.000(3) -0.022(4) C18 0.034(3) 0.025(3) 0.050(3) -0.007(2) -0.007(2) -0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F2 1.589(3) . ? P1 F1 1.589(3) . ? P1 F6 1.592(3) . ? P1 F4 1.596(3) . ? P1 F3 1.605(3) . ? P1 F5 1.606(3) . ? N1 C3 1.348(5) . ? N1 C2 1.449(5) . ? N1 C1 1.459(5) . ? N2 C9 1.289(5) . ? N2 N3 1.380(5) . ? N3 C10 1.313(5) . ? N4 C14 1.356(5) . ? N4 C18 1.447(6) . ? N4 C17 1.451(6) . ? C3 C8 1.404(6) . ? C3 C4 1.429(5) . ? C4 C5 1.353(6) . ? C5 C6 1.405(6) . ? C6 C7 1.407(6) . ? C6 C9 1.441(6) . ? C7 C8 1.370(6) . ? C10 C11 1.410(6) . ? C11 C16 1.400(6) . ? C11 C12 1.406(6) . ? C12 C13 1.383(6) . ? C13 C14 1.386(6) . ? C14 C15 1.413(6) . ? C15 C16 1.364(6) . ? C2S O2S 1.450(9) . ? C2S C2S 1.550(10) 2_766 ? 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 F2 P1 F1 90.18(15) . . ? F2 P1 F6 90.69(17) . . ? F1 P1 F6 90.62(16) . . ? F2 P1 F4 90.15(15) . . ? F1 P1 F4 179.01(16) . . ? F6 P1 F4 90.31(16) . . ? F2 P1 F3 89.89(16) . . ? F1 P1 F3 89.90(16) . . ? F6 P1 F3 179.22(16) . . ? F4 P1 F3 89.16(16) . . ? F2 P1 F5 179.17(17) . . ? F1 P1 F5 89.88(16) . . ? F6 P1 F5 90.14(17) . . ? F4 P1 F5 89.77(16) . . ? F3 P1 F5 89.28(16) . . ? C3 N1 C2 121.0(4) . . ? C3 N1 C1 121.0(4) . . ? C2 N1 C1 118.0(4) . . ? C9 N2 N3 113.5(4) . . ? C10 N3 N2 120.1(4) . . ? C14 N4 C18 122.7(4) . . ? C14 N4 C17 120.5(4) . . ? C18 N4 C17 116.7(4) . . ? N1 C3 C8 122.2(4) . . ? N1 C3 C4 122.0(4) . . ? C8 C3 C4 115.9(4) . . ? C5 C4 C3 122.1(4) . . ? C4 C5 C6 121.6(4) . . ? C5 C6 C7 117.1(4) . . ? C5 C6 C9 122.7(4) . . ? C7 C6 C9 120.3(4) . . ? C8 C7 C6 121.5(4) . . ? C7 C8 C3 122.0(4) . . ? N2 C9 C6 122.1(4) . . ? N3 C10 C11 125.8(4) . . ? C16 C11 C12 117.1(4) . . ? C16 C11 C10 124.6(4) . . ? C12 C11 C10 118.3(4) . . ? C13 C12 C11 121.3(4) . . ? C12 C13 C14 121.0(4) . . ? N4 C14 C13 121.2(4) . . ? N4 C14 C15 121.1(4) . . ? C13 C14 C15 117.7(4) . . ? C16 C15 C14 121.1(4) . . ? C15 C16 C11 121.6(4) . . ? O2S C2S C2S 108.3(6) . 2_766 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.850 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.141