# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1102 data_GLOBAL # 1. SUBMISSION DETAILS _publ_contact_author_name 'Gleiter, Rolf' _publ_contact_author_address ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 D-69120 Heidelberg Germany ; _publ_contact_author_phone '049 6221 54- 8400' _publ_contact_author_fax '049 6221 54- 4205' _publ_contact_author_email 's91@ix.urz.uni-heidelberg.de' _publ_requested_journal 'Chem. Comm.' _publ_requested_coeditor_name ? _publ_contact_letter ; paper submitted for publication in Chem. Comm. ; #========================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; 1,8-Diazabicyclo[6.6.6]eicosa-4,11,17-triyne - a flexible cage for protons, copper(I) and silver(I). ; loop_ _publ_author_name _publ_author_address 'Kunze, Andreas' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Gleiter, Rolf' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; 'Rominger, Frank' ; Organisch-Chemisches Institut Universit\"at Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; #========================================================================== data_3-H+ _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H28 F12 N2 O8' _chemical_formula_weight 724.50 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 16.07440(10) _cell_length_b 10.2190(2) _cell_length_c 18.9058(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.5930(10) _cell_angle_gamma 90.00 _cell_volume 3104.35(8) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron_ _exptl_crystal_colour colorless _exptl_crystal_size_max .39 _exptl_crystal_size_mid .28 _exptl_crystal_size_min .25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method ? _exptl_crystal_F_000 1480 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Siemens SMART CCD' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11183 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.47 _reflns_number_total 2687 _reflns_number_observed 2088 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0558P)^2^+4.5481P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2683 _refine_ls_number_parameters 329 _refine_ls_number_restraints 264 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_obs 0.0461 _refine_ls_wR_factor_all 0.1277 _refine_ls_wR_factor_obs 0.1119 _refine_ls_goodness_of_fit_all 1.041 _refine_ls_goodness_of_fit_obs 1.066 _refine_ls_restrained_S_all 1.202 _refine_ls_restrained_S_obs 1.253 _refine_ls_shift/esd_max -0.082 _refine_ls_shift/esd_mean 0.004 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.62102(13) 0.0518(2) 0.32927(11) 0.0313(5) Uani 1 d . . H1 H 0.5759(16) 0.0504(24) 0.3010(14) 0.031(6) Uiso 1 d . . C1 C 0.6425(2) -0.0896(2) 0.34435(14) 0.0348(6) Uani 1 d . . H1A H 0.7014(17) -0.0911(26) 0.3601(14) 0.038(7) Uiso 1 d . . H1B H 0.6085(15) -0.1203(25) 0.3839(14) 0.033(7) Uiso 1 d . . C2 C 0.6246(2) -0.1743(3) 0.27942(14) 0.0360(6) Uani 1 d . . H2A H 0.6590(17) -0.1476(28) 0.2378(16) 0.045(8) Uiso 1 d . . H2B H 0.6400(17) -0.2629(31) 0.2921(15) 0.045(8) Uiso 1 d . . C3 C 0.53614(15) -0.1721(2) 0.25798(12) 0.0317(6) Uani 1 d . . C4 C 0.6881(2) 0.1209(3) 0.2894(2) 0.0395(6) Uani 1 d . . H4A H 0.7150(17) 0.0554(29) 0.2598(15) 0.043(8) Uiso 1 d . . H4B H 0.7277(17) 0.1509(27) 0.3262(15) 0.044(7) Uiso 1 d . . C5 C 0.6503(2) 0.2309(3) 0.2449(2) 0.0425(7) Uani 1 d . . H5A H 0.6225(17) 0.2937(29) 0.2758(15) 0.044(8) Uiso 1 d . . H5B H 0.6962(19) 0.2801(31) 0.2221(16) 0.056(8) Uiso 1 d . . C6 C 0.5926(2) 0.1809(2) 0.18963(14) 0.0380(6) Uani 1 d . . C7 C 0.5488(2) 0.1398(3) 0.14288(13) 0.0372(6) Uani 1 d . . C8 C 0.5090(2) 0.0968(3) 0.41410(14) 0.0426(7) Uani 1 d . . H8A H 0.5005(17) 0.0028(32) 0.4227(15) 0.047(8) Uiso 1 d . . H8B H 0.4982(18) 0.1480(30) 0.4592(17) 0.052(8) Uiso 1 d . . C9 C 0.5984(2) 0.1245(3) 0.39547(14) 0.0397(6) Uani 1 d . . H9A H 0.6392(17) 0.0956(28) 0.4326(15) 0.047(8) Uiso 1 d . . H9B H 0.6069(17) 0.2208(32) 0.3851(15) 0.051(8) Uiso 1 d . . C10 C 0.2521(2) 0.4225(3) 0.55421(15) 0.0519(8) Uani 1 d DU . F1 F 0.3117(2) 0.4413(3) 0.5108(2) 0.1068(14) Uani 0.926(5) d PDU 1 F2 F 0.1884(2) 0.3699(2) 0.51612(12) 0.0753(10) Uani 0.926(5) d PDU 1 F3 F 0.2747(2) 0.3308(2) 0.59957(11) 0.0711(9) Uani 0.926(5) d PDU 1 F1B F 0.2043(17) 0.3270(55) 0.5776(19) 0.316(48) Uani 0.074(5) d PDU 2 F2B F 0.3290(10) 0.3881(31) 0.5672(11) 0.230(31) Uani 0.074(5) d PDU 2 F3B F 0.2407(10) 0.4184(19) 0.4876(8) 0.041(6) Uani 0.074(5) d PDU 2 C11 C 0.2268(2) 0.5490(3) 0.59086(14) 0.0436(7) Uani 1 d . . O1 O 0.1776(2) 0.6159(2) 0.55301(12) 0.0794(9) Uani 1 d . . O2 O 0.25365(13) 0.5711(2) 0.65035(10) 0.0523(6) Uani 1 d . . C12 C 0.0272(2) 0.9710(3) 0.6274(2) 0.0581(8) Uani 1 d DU . F4 F 0.0288(2) 1.0613(3) 0.57870(15) 0.083(2) Uani 0.863(10) d PDU 1 F5 F 0.0726(2) 1.0074(3) 0.68285(15) 0.0838(15) Uani 0.863(10) d PDU 1 F6 F -0.0500(2) 0.9665(3) 0.6511(2) 0.0915(14) Uani 0.863(10) d PDU 1 F4B F 0.0063(12) 0.9837(32) 0.6899(8) 0.183(19) Uani 0.137(10) d PDU 2 F5B F -0.0373(10) 1.0265(25) 0.5929(12) 0.199(23) Uani 0.137(10) d PDU 2 F6B F 0.0917(10) 1.0566(15) 0.6207(10) 0.158(20) Uani 0.137(10) d PDU 2 C13 C 0.0532(2) 0.8386(3) 0.59821(14) 0.0462(7) Uani 1 d . . O3 O 0.13173(15) 0.8214(2) 0.60481(13) 0.0633(7) Uani 1 d . . O4 O 0.00116(15) 0.7667(2) 0.57257(11) 0.0604(6) Uani 1 d . . H2 H 0.1519(34) 0.7307(62) 0.5784(29) 0.150(19) Uiso 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 N1 0.0336(11) 0.0301(11) 0.0294(11) 0.0000(9) -0.0122(9) 0.0003(9) C1 0.0395(15) 0.0313(14) 0.0329(14) 0.0037(11) -0.0104(11) 0.0043(11) C2 0.0390(14) 0.0323(15) 0.0362(15) -0.0002(11) -0.0072(11) 0.0038(11) C3 0.0437(13) 0.0239(12) 0.0273(13) -0.0001(10) -0.0048(10) 0.0008(10) C4 0.0340(14) 0.040(2) 0.044(2) 0.0020(13) -0.0091(12) -0.0056(12) C5 0.046(2) 0.037(2) 0.043(2) 0.0065(13) -0.0090(13) -0.0111(13) C6 0.0435(14) 0.0322(14) 0.0381(15) 0.0072(11) -0.0022(12) -0.0036(11) C7 0.0449(15) 0.0329(14) 0.0339(14) 0.0068(11) 0.0000(12) -0.0038(11) C8 0.057(2) 0.042(2) 0.0287(14) -0.0019(12) -0.0046(12) 0.0079(13) C9 0.051(2) 0.037(2) 0.0301(13) -0.0057(11) -0.0162(12) 0.0038(12) C10 0.070(2) 0.051(2) 0.0342(15) -0.0005(13) -0.0072(14) 0.0198(15) F1 0.134(3) 0.083(2) 0.108(2) -0.003(2) 0.076(2) 0.022(2) F2 0.104(2) 0.0592(14) 0.0609(15) -0.0246(11) -0.0316(13) 0.0214(13) F3 0.106(2) 0.0492(13) 0.0569(14) 0.0017(10) -0.0224(12) 0.0362(12) F1B 0.385(64) 0.349(82) 0.214(57) 0.188(62) 0.013(62) -0.190(61) F2B 0.100(21) 0.488(78) 0.101(29) -0.193(41) -0.061(21) 0.174(32) F3B 0.040(8) 0.043(7) 0.039(7) -0.003(4) 0.003(4) 0.008(4) C11 0.052(2) 0.044(2) 0.0333(15) -0.0032(12) -0.0067(12) 0.0086(13) O1 0.127(2) 0.0591(15) 0.0498(13) -0.0188(11) -0.0387(14) 0.0506(15) O2 0.0580(12) 0.0618(14) 0.0365(11) -0.0112(9) -0.0110(9) 0.0071(10) C12 0.077(2) 0.044(2) 0.053(2) -0.006(2) -0.003(2) 0.006(2) F4 0.151(4) 0.0337(14) 0.067(2) 0.0081(12) 0.016(2) 0.018(2) F5 0.118(3) 0.061(2) 0.071(2) -0.037(2) -0.020(2) 0.008(2) F6 0.088(2) 0.083(2) 0.104(3) -0.016(2) 0.025(2) 0.017(2) F4B 0.338(56) 0.135(25) 0.080(14) 0.002(18) 0.080(23) 0.002(36) F5B 0.237(32) 0.100(24) 0.254(40) -0.011(28) -0.131(37) 0.090(24) F6B 0.161(19) 0.040(12) 0.278(51) -0.083(21) 0.114(24) -0.025(12) C13 0.072(2) 0.033(2) 0.0332(15) 0.0011(12) -0.0103(13) 0.0009(14) O3 0.069(2) 0.0436(13) 0.076(2) -0.0218(11) -0.0198(12) 0.0118(11) O4 0.081(2) 0.0499(13) 0.0502(13) -0.0054(10) -0.0102(11) -0.0134(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 N1 C9 1.508(3) . ? N1 C4 1.509(3) . ? N1 C1 1.512(3) . ? N1 H1 0.89(3) . ? C1 C2 1.523(4) . ? C1 H1A 0.98(3) . ? C1 H1B 0.99(3) . ? C2 C3 1.468(3) . ? C2 H2A 1.01(3) . ? C2 H2B 0.97(3) . ? C3 C3 1.192(5) 2_655 ? C4 C5 1.521(4) . ? C4 H4A 0.98(3) . ? C4 H4B 0.98(3) . ? C5 C6 1.468(4) . ? C5 H5A 0.98(3) . ? C5 H5B 1.00(3) . ? C6 C7 1.192(4) . ? C7 C8 1.469(4) 2_655 ? C8 C7 1.469(4) 2_655 ? C8 C9 1.516(4) . ? C8 H8A 0.98(3) . ? C8 H8B 1.02(3) . ? C9 H9A 0.99(3) . ? C9 H9B 1.01(3) . ? C10 F3B 1.268(14) . ? C10 F1 1.293(4) . ? C10 F2B 1.30(2) . ? C10 F3 1.314(3) . ? C10 F1B 1.32(2) . ? C10 F2 1.347(4) . ? C10 C11 1.527(4) . ? C11 O2 1.215(3) . ? C11 O1 1.255(3) . ? O1 H2 1.34(6) . ? C12 F4B 1.24(2) . ? C12 F4 1.304(4) . ? C12 F5 1.314(4) . ? C12 F6 1.333(4) . ? C12 F5B 1.336(15) . ? C12 F6B 1.364(14) . ? C12 C13 1.524(4) . ? C13 O4 1.206(3) . ? C13 O3 1.276(4) . ? O3 H2 1.11(6) . ? 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 C9 N1 C4 112.1(2) . . ? C9 N1 C1 111.9(2) . . ? C4 N1 C1 112.3(2) . . ? C9 N1 H1 107.2(16) . . ? C4 N1 H1 106.8(16) . . ? C1 N1 H1 106.1(16) . . ? N1 C1 C2 110.7(2) . . ? N1 C1 H1A 106.6(15) . . ? C2 C1 H1A 113.2(15) . . ? N1 C1 H1B 108.5(15) . . ? C2 C1 H1B 109.5(15) . . ? H1A C1 H1B 108.2(21) . . ? C3 C2 C1 112.0(2) . . ? C3 C2 H2A 109.1(16) . . ? C1 C2 H2A 112.3(16) . . ? C3 C2 H2B 108.8(16) . . ? C1 C2 H2B 106.9(17) . . ? H2A C2 H2B 107.6(23) . . ? C3 C3 C2 178.4(3) 2_655 . ? N1 C4 C5 110.0(2) . . ? N1 C4 H4A 107.3(16) . . ? C5 C4 H4A 111.5(16) . . ? N1 C4 H4B 104.5(16) . . ? C5 C4 H4B 113.8(16) . . ? H4A C4 H4B 109.3(22) . . ? C6 C5 C4 111.8(2) . . ? C6 C5 H5A 111.3(16) . . ? C4 C5 H5A 109.5(16) . . ? C6 C5 H5B 109.1(17) . . ? C4 C5 H5B 108.7(17) . . ? H5A C5 H5B 106.3(24) . . ? C7 C6 C5 177.1(3) . . ? C6 C7 C8 176.1(3) . 2_655 ? C7 C8 C9 111.0(2) 2_655 . ? C7 C8 H8A 109.0(16) 2_655 . ? C9 C8 H8A 110.8(17) . . ? C7 C8 H8B 110.0(17) 2_655 . ? C9 C8 H8B 106.4(16) . . ? H8A C8 H8B 109.6(24) . . ? N1 C9 C8 110.7(2) . . ? N1 C9 H9A 105.7(16) . . ? C8 C9 H9A 113.1(16) . . ? N1 C9 H9B 106.3(17) . . ? C8 C9 H9B 111.1(16) . . ? H9A C9 H9B 109.5(23) . . ? F3B C10 F2B 106.8(12) . . ? F1 C10 F3 108.9(3) . . ? F3B C10 F1B 103.8(18) . . ? F2B C10 F1B 107.1(19) . . ? F1 C10 F2 106.6(3) . . ? F3 C10 F2 104.9(3) . . ? F3B C10 C11 116.4(9) . . ? F1 C10 C11 111.9(3) . . ? F2B C10 C11 113.9(14) . . ? F3 C10 C11 112.3(2) . . ? F1B C10 C11 107.9(29) . . ? F2 C10 C11 111.9(2) . . ? O2 C11 O1 129.0(3) . . ? O2 C11 C10 119.0(2) . . ? O1 C11 C10 111.9(2) . . ? C11 O1 H2 118.0(23) . . ? F4 C12 F5 110.0(3) . . ? F4 C12 F6 107.4(3) . . ? F5 C12 F6 104.0(3) . . ? F4B C12 F5B 101.1(14) . . ? F4B C12 F6B 104.3(12) . . ? F5B C12 F6B 105.4(11) . . ? F4B C12 C13 121.3(15) . . ? F4 C12 C13 111.2(3) . . ? F5 C12 C13 112.9(3) . . ? F6 C12 C13 111.0(3) . . ? F5B C12 C13 114.6(13) . . ? F6B C12 C13 108.6(8) . . ? O4 C13 O3 129.0(3) . . ? O4 C13 C12 119.5(3) . . ? O3 C13 C12 111.6(3) . . ? C13 O3 H2 111.9(28) . . ? _refine_diff_density_max 0.384 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.045 #========================================================================== data_3-Ag+ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19.25 H24.50 Ag Cl0.50 F3 N2 O3 S' _chemical_formula_weight 546.56 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' 'Cl' 'Cl' 0.1484 0.1585 '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 13.4273(2) _cell_length_b 13.9115(3) _cell_length_c 14.0299(3) _cell_angle_alpha 65.5820(10) _cell_angle_beta 73.2750(10) _cell_angle_gamma 64.6590(10) _cell_volume 2137.02(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max .24 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1106 _exptl_absorpt_coefficient_mu 1.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.91 _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15934 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 25.49 _reflns_number_total 7079 _reflns_number_gt 6038 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0314P)^2^+4.9533P] 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 7079 _refine_ls_number_parameters 550 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0745 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.420 _refine_ls_shift/su_mean 0.014 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 0.34053(2) 0.46245(2) 0.24981(2) 0.02405(8) Uani 1 1 d . . . Ag2 Ag 0.83449(2) 0.87771(2) 0.17384(2) 0.02394(8) Uani 1 1 d . . . N1 N 0.4053(3) 0.4928(3) 0.3666(2) 0.0283(7) Uani 1 1 d . . . N2 N 0.2736(3) 0.4350(3) 0.1326(2) 0.0282(7) Uani 1 1 d . . . N3 N 0.7379(2) 0.8516(2) 0.0796(2) 0.0263(7) Uani 1 1 d . . . N4 N 0.9350(2) 0.9017(2) 0.2663(2) 0.0273(7) Uani 1 1 d . . . C1 C 0.3269(4) 0.4807(4) 0.4671(3) 0.0423(10) Uani 1 1 d . . . H1A H 0.3449 0.5084 0.5123 0.051 Uiso 1 1 calc R . . H1B H 0.3391 0.3995 0.5047 0.051 Uiso 1 1 calc R . . C2 C 0.2049(3) 0.5432(4) 0.4534(3) 0.0374(9) Uani 1 1 d . . . H2A H 0.1600 0.5279 0.5239 0.045 Uiso 1 1 calc R . . H2B H 0.1908 0.6253 0.4239 0.045 Uiso 1 1 calc R . . C3 C 0.1659(3) 0.5138(3) 0.3846(3) 0.0335(9) Uani 1 1 d . . . C4 C 0.1337(3) 0.4915(3) 0.3281(3) 0.0353(9) Uani 1 1 d . . . C5 C 0.0949(3) 0.4601(4) 0.2607(3) 0.0443(11) Uani 1 1 d . . . H5A H 0.0137 0.5008 0.2613 0.053 Uiso 1 1 calc R . . H5B H 0.1079 0.3783 0.2920 0.053 Uiso 1 1 calc R . . C6 C 0.1504(3) 0.4853(4) 0.1464(4) 0.0444(11) Uani 1 1 d . . . H6A H 0.1219 0.4574 0.1093 0.053 Uiso 1 1 calc R . . H6B H 0.1282 0.5682 0.1120 0.053 Uiso 1 1 calc R . . C7 C 0.3200(4) 0.4913(4) 0.0234(3) 0.0409(10) Uani 1 1 d . . . H7A H 0.2793 0.4943 -0.0270 0.049 Uiso 1 1 calc R . . H7B H 0.3987 0.4437 0.0100 0.049 Uiso 1 1 calc R . . C8 C 0.3148(4) 0.6097(3) 0.0003(3) 0.0390(10) Uani 1 1 d . . . H8A H 0.3514 0.6366 -0.0727 0.047 Uiso 1 1 calc R . . H8B H 0.2359 0.6601 0.0032 0.047 Uiso 1 1 calc R . . C9 C 0.3674(3) 0.6202(3) 0.0727(3) 0.0308(9) Uani 1 1 d . . . C10 C 0.4094(3) 0.6285(3) 0.1323(3) 0.0303(9) Uani 1 1 d . . . C11 C 0.4636(4) 0.6375(4) 0.2049(3) 0.0416(10) Uani 1 1 d . . . H11A H 0.4606 0.7163 0.1809 0.050 Uiso 1 1 calc R . . H11B H 0.5430 0.5885 0.1995 0.050 Uiso 1 1 calc R . . C12 C 0.4130(4) 0.6051(4) 0.3207(3) 0.0446(11) Uani 1 1 d . . . H12A H 0.4582 0.6095 0.3625 0.054 Uiso 1 1 calc R . . H12B H 0.3374 0.6614 0.3277 0.054 Uiso 1 1 calc R . . C13 C 0.5161(4) 0.4036(4) 0.3884(4) 0.0437(11) Uani 1 1 d . . . H13A H 0.5344 0.4028 0.4523 0.052 Uiso 1 1 calc R . . H13B H 0.5722 0.4250 0.3287 0.052 Uiso 1 1 calc R . . C14 C 0.5278(4) 0.2857(4) 0.4048(4) 0.0474(11) Uani 1 1 d . . . H14A H 0.6063 0.2361 0.4128 0.057 Uiso 1 1 calc R . . H14B H 0.4817 0.2588 0.4718 0.057 Uiso 1 1 calc R . . C15 C 0.4957(3) 0.2735(3) 0.3197(3) 0.0360(9) Uani 1 1 d . . . C16 C 0.4669(3) 0.2614(3) 0.2535(3) 0.0345(9) Uani 1 1 d . . . C17 C 0.4332(4) 0.2469(3) 0.1700(4) 0.0419(10) Uani 1 1 d . . . H17A H 0.4479 0.1657 0.1882 0.050 Uiso 1 1 calc R . . H17B H 0.4803 0.2705 0.1026 0.050 Uiso 1 1 calc R . . C18 C 0.3123(4) 0.3126(3) 0.1538(4) 0.0417(10) Uani 1 1 d . . . H18A H 0.2995 0.3010 0.0940 0.050 Uiso 1 1 calc R . . H18B H 0.2658 0.2803 0.2177 0.050 Uiso 1 1 calc R . . C21 C 0.6352(3) 0.9522(3) 0.0566(3) 0.0315(9) Uani 1 1 d . . . H21A H 0.5801 0.9469 0.1213 0.038 Uiso 1 1 calc R . . H21B H 0.6036 0.9510 0.0017 0.038 Uiso 1 1 calc R . . C22 C 0.6515(3) 1.0655(3) 0.0191(3) 0.0315(9) Uani 1 1 d . . . H22A H 0.7008 1.0741 -0.0492 0.038 Uiso 1 1 calc R . . H22B H 0.5786 1.1271 0.0066 0.038 Uiso 1 1 calc R . . C23 C 0.6993(3) 1.0787(3) 0.0931(3) 0.0299(9) Uani 1 1 d . . . C24 C 0.7401(3) 1.0889(3) 0.1527(3) 0.0317(9) Uani 1 1 d . . . C25 C 0.7896(4) 1.0993(3) 0.2274(3) 0.0392(10) Uani 1 1 d . . . H25A H 0.7469 1.0793 0.2986 0.047 Uiso 1 1 calc R . . H25B H 0.7824 1.1790 0.2061 0.047 Uiso 1 1 calc R . . C26 C 0.9122(3) 1.0246(3) 0.2336(3) 0.0368(10) Uani 1 1 d . . . H26A H 0.9554 1.0482 0.1635 0.044 Uiso 1 1 calc R . . H26B H 0.9391 1.0375 0.2844 0.044 Uiso 1 1 calc R . . C27 C 1.0549(3) 0.8391(3) 0.2405(3) 0.0359(9) Uani 1 1 d . . . H27A H 1.0702 0.7575 0.2789 0.043 Uiso 1 1 calc R . . H27B H 1.0991 0.8625 0.2666 0.043 Uiso 1 1 calc R . . C28 C 1.0944(3) 0.8569(3) 0.1229(3) 0.0376(10) Uani 1 1 d . . . H28A H 1.0833 0.9378 0.0849 0.045 Uiso 1 1 calc R . . H28B H 1.1751 0.8136 0.1133 0.045 Uiso 1 1 calc R . . C29 C 1.0365(3) 0.8223(3) 0.0750(3) 0.0335(9) Uani 1 1 d . . . C30 C 0.9889(3) 0.7932(3) 0.0381(3) 0.0324(9) Uani 1 1 d . . . C31 C 0.9296(3) 0.7573(3) -0.0067(3) 0.0365(9) Uani 1 1 d . . . H31A H 0.9292 0.6812 0.0401 0.044 Uiso 1 1 calc R . . H31B H 0.9706 0.7516 -0.0763 0.044 Uiso 1 1 calc R . . C32 C 0.8094(3) 0.8378(3) -0.0205(3) 0.0311(8) Uani 1 1 d . . . H32A H 0.8103 0.9127 -0.0704 0.037 Uiso 1 1 calc R . . H32B H 0.7758 0.8093 -0.0526 0.037 Uiso 1 1 calc R . . C33 C 0.7103(4) 0.7490(3) 0.1456(3) 0.0355(9) Uani 1 1 d . . . H33A H 0.7775 0.6817 0.1426 0.043 Uiso 1 1 calc R . . H33B H 0.6529 0.7479 0.1152 0.043 Uiso 1 1 calc R . . C34 C 0.6676(4) 0.7403(4) 0.2617(3) 0.0391(10) Uani 1 1 d . . . H34A H 0.5985 0.8058 0.2650 0.047 Uiso 1 1 calc R . . H34B H 0.6489 0.6711 0.2994 0.047 Uiso 1 1 calc R . . C35 C 0.7481(3) 0.7372(3) 0.3164(3) 0.0322(9) Uani 1 1 d . . . C36 C 0.8112(3) 0.7372(3) 0.3618(3) 0.0328(9) Uani 1 1 d . . . C37 C 0.8877(4) 0.7404(3) 0.4174(3) 0.0380(10) Uani 1 1 d . . . H37A H 0.9624 0.6843 0.4061 0.046 Uiso 1 1 calc R . . H37B H 0.8612 0.7177 0.4941 0.046 Uiso 1 1 calc R . . C38 C 0.8978(4) 0.8568(3) 0.3811(3) 0.0371(9) Uani 1 1 d . . . H38A H 0.8246 0.9112 0.3990 0.044 Uiso 1 1 calc R . . H38B H 0.9512 0.8513 0.4209 0.044 Uiso 1 1 calc R . . S1 S -0.16413(10) 0.39431(10) 0.24460(9) 0.0432(3) Uani 1 1 d . . . O1 O -0.2094(5) 0.4865(3) 0.2804(3) 0.117(2) Uani 1 1 d . . . O2 O -0.0602(4) 0.3844(5) 0.1791(3) 0.1081(18) Uani 1 1 d . . . O3 O -0.2400(4) 0.3717(4) 0.2123(3) 0.0838(13) Uani 1 1 d . . . C40 C -0.1294(4) 0.2768(4) 0.3666(4) 0.0504(12) Uani 1 1 d . . . F1 F -0.0510(3) 0.2796(3) 0.4054(2) 0.0754(9) Uani 1 1 d . . . F2 F -0.2181(3) 0.2828(3) 0.4420(2) 0.0756(9) Uani 1 1 d . . . F3 F -0.0952(4) 0.1797(3) 0.3561(3) 0.1190(17) Uani 1 1 d . . . S2 S 0.32748(8) 0.93106(9) 0.28513(8) 0.0353(2) Uani 1 1 d . . . O4 O 0.3838(3) 0.8414(3) 0.3699(3) 0.0700(11) Uani 1 1 d . . . O5 O 0.3845(3) 1.0061(3) 0.2134(3) 0.0658(10) Uani 1 1 d . . . O6 O 0.2754(3) 0.8984(3) 0.2347(3) 0.0594(9) Uani 1 1 d . . . C41 C 0.2089(6) 1.0214(5) 0.3479(5) 0.084(2) Uani 1 1 d . . . F4 F 0.2337(6) 1.0636(6) 0.3977(5) 0.183(3) Uani 1 1 d . . . F5 F 0.1496(4) 1.1106(3) 0.2748(3) 0.1272(19) Uani 1 1 d . . . F6 F 0.1406(3) 0.9693(3) 0.4120(3) 0.1203(18) Uani 1 1 d . . . C42 C 0.4471(8) 1.0078(8) 0.4630(8) 0.062(3) Uani 0.50 1 d PDU . . H42A H 0.4091 0.9547 0.4783 0.074 Uiso 0.50 1 calc PR . . H42B H 0.4157 1.0768 0.4040 0.074 Uiso 0.50 1 calc PR . . Cl1 Cl 0.5924(9) 0.9445(10) 0.4306(10) 0.124(4) Uani 0.50 1 d PDU . . Cl2 Cl 0.4303(8) 1.0427(7) 0.5800(7) 0.0718(16) Uani 0.50 1 d PDU . . 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 0.02916(16) 0.02406(15) 0.02273(15) -0.00764(11) -0.00745(11) -0.01050(12) Ag2 0.02409(15) 0.02328(15) 0.02700(15) -0.00786(11) -0.00739(11) -0.00869(11) N1 0.0351(18) 0.0313(17) 0.0244(16) -0.0089(13) -0.0068(13) -0.0157(14) N2 0.0320(17) 0.0285(16) 0.0289(16) -0.0108(14) -0.0103(13) -0.0100(14) N3 0.0255(16) 0.0263(16) 0.0300(16) -0.0090(13) -0.0061(13) -0.0107(13) N4 0.0286(17) 0.0257(16) 0.0316(17) -0.0094(13) -0.0104(13) -0.0093(13) C1 0.055(3) 0.050(3) 0.029(2) -0.014(2) -0.0093(19) -0.023(2) C2 0.044(2) 0.043(2) 0.029(2) -0.0185(19) 0.0024(18) -0.018(2) C3 0.030(2) 0.034(2) 0.032(2) -0.0126(18) 0.0043(17) -0.0114(17) C4 0.030(2) 0.041(2) 0.036(2) -0.0150(19) 0.0003(17) -0.0146(18) C5 0.030(2) 0.063(3) 0.051(3) -0.024(2) -0.0038(19) -0.022(2) C6 0.037(2) 0.057(3) 0.049(3) -0.023(2) -0.016(2) -0.014(2) C7 0.055(3) 0.042(2) 0.030(2) -0.0127(19) -0.0120(19) -0.017(2) C8 0.047(3) 0.042(2) 0.029(2) -0.0047(18) -0.0115(18) -0.019(2) C9 0.033(2) 0.0241(19) 0.025(2) 0.0004(16) -0.0039(17) -0.0099(17) C10 0.034(2) 0.027(2) 0.026(2) -0.0032(16) -0.0011(17) -0.0152(17) C11 0.058(3) 0.046(2) 0.036(2) -0.012(2) -0.003(2) -0.035(2) C12 0.070(3) 0.043(2) 0.037(2) -0.006(2) -0.018(2) -0.034(2) C13 0.046(3) 0.046(3) 0.046(3) -0.013(2) -0.024(2) -0.013(2) C14 0.048(3) 0.041(2) 0.048(3) -0.012(2) -0.028(2) 0.000(2) C15 0.039(2) 0.0220(19) 0.041(2) -0.0092(18) -0.0161(19) 0.0000(17) C16 0.036(2) 0.0199(19) 0.042(2) -0.0081(17) -0.0112(19) -0.0041(16) C17 0.052(3) 0.026(2) 0.054(3) -0.020(2) -0.014(2) -0.0087(19) C18 0.059(3) 0.034(2) 0.045(3) -0.017(2) -0.018(2) -0.017(2) C21 0.0214(19) 0.039(2) 0.035(2) -0.0128(18) -0.0088(16) -0.0090(16) C22 0.030(2) 0.028(2) 0.034(2) -0.0085(17) -0.0135(17) -0.0031(16) C23 0.027(2) 0.0200(18) 0.034(2) -0.0058(16) -0.0082(17) -0.0012(15) C24 0.031(2) 0.0205(19) 0.039(2) -0.0097(17) -0.0094(18) -0.0022(16) C25 0.051(3) 0.024(2) 0.047(2) -0.0144(18) -0.019(2) -0.0066(18) C26 0.048(3) 0.027(2) 0.047(2) -0.0119(18) -0.018(2) -0.0161(18) C27 0.029(2) 0.033(2) 0.048(2) -0.0096(19) -0.0154(18) -0.0107(17) C28 0.024(2) 0.038(2) 0.050(3) -0.012(2) -0.0060(18) -0.0126(17) C29 0.023(2) 0.032(2) 0.037(2) -0.0093(18) -0.0006(17) -0.0061(17) C30 0.024(2) 0.033(2) 0.031(2) -0.0117(18) 0.0006(16) -0.0034(17) C31 0.034(2) 0.039(2) 0.040(2) -0.0233(19) -0.0038(18) -0.0062(18) C32 0.034(2) 0.036(2) 0.029(2) -0.0152(17) -0.0079(16) -0.0107(17) C33 0.043(2) 0.035(2) 0.038(2) -0.0084(18) -0.0085(18) -0.0230(19) C34 0.042(2) 0.044(2) 0.036(2) -0.0063(19) -0.0040(19) -0.027(2) C35 0.038(2) 0.028(2) 0.026(2) -0.0031(16) 0.0026(17) -0.0170(17) C36 0.037(2) 0.029(2) 0.029(2) -0.0063(17) -0.0021(17) -0.0128(17) C37 0.045(2) 0.039(2) 0.028(2) -0.0033(18) -0.0115(18) -0.0163(19) C38 0.044(2) 0.041(2) 0.032(2) -0.0115(18) -0.0150(18) -0.0155(19) S1 0.0528(7) 0.0472(6) 0.0357(6) -0.0137(5) -0.0039(5) -0.0244(5) O1 0.209(6) 0.034(2) 0.070(3) -0.011(2) -0.031(3) -0.008(3) O2 0.092(3) 0.221(6) 0.052(2) -0.061(3) 0.024(2) -0.098(4) O3 0.090(3) 0.113(3) 0.061(2) 0.002(2) -0.041(2) -0.059(3) C40 0.054(3) 0.044(3) 0.063(3) -0.034(2) -0.026(3) 0.001(2) F1 0.0594(19) 0.110(3) 0.070(2) -0.0381(19) -0.0282(16) -0.0217(18) F2 0.075(2) 0.086(2) 0.0569(19) 0.0002(17) -0.0106(16) -0.0423(18) F3 0.188(5) 0.0478(19) 0.121(3) -0.039(2) -0.079(3) 0.005(2) S2 0.0346(5) 0.0434(6) 0.0321(5) -0.0152(5) -0.0049(4) -0.0149(5) O4 0.059(2) 0.082(3) 0.053(2) -0.0037(19) -0.0275(18) -0.017(2) O5 0.056(2) 0.083(3) 0.065(2) -0.020(2) 0.0059(18) -0.045(2) O6 0.073(2) 0.068(2) 0.057(2) -0.0197(18) -0.0229(18) -0.0347(19) C41 0.107(5) 0.062(4) 0.054(3) -0.023(3) 0.029(4) -0.026(4) F4 0.252(7) 0.216(6) 0.159(5) -0.161(5) 0.042(5) -0.102(6) F5 0.121(3) 0.060(2) 0.094(3) -0.009(2) 0.037(3) 0.014(2) F6 0.097(3) 0.081(2) 0.086(3) 0.000(2) 0.052(2) -0.013(2) C42 0.061(6) 0.045(6) 0.084(7) -0.017(5) -0.012(6) -0.026(5) Cl1 0.057(3) 0.129(6) 0.168(9) -0.079(6) 0.050(5) -0.029(3) Cl2 0.083(5) 0.063(3) 0.077(3) -0.034(2) 0.014(3) -0.038(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 N2 2.306(3) . ? Ag1 N1 2.308(3) . ? Ag1 C15 2.563(4) . ? Ag1 C16 2.564(4) . ? Ag1 C10 2.591(4) . ? Ag1 C3 2.592(4) . ? Ag1 C4 2.595(4) . ? Ag1 C9 2.602(3) . ? Ag2 N3 2.313(3) . ? Ag2 N4 2.317(3) . ? Ag2 C35 2.557(4) . ? Ag2 C23 2.573(3) . ? Ag2 C24 2.576(4) . ? Ag2 C36 2.580(4) . ? Ag2 C30 2.608(4) . ? Ag2 C29 2.608(4) . ? N1 C12 1.460(5) . ? N1 C13 1.489(5) . ? N1 C1 1.492(5) . ? N2 C18 1.473(5) . ? N2 C6 1.484(5) . ? N2 C7 1.491(5) . ? N3 C21 1.481(5) . ? N3 C33 1.482(5) . ? N3 C32 1.490(5) . ? N4 C38 1.485(5) . ? N4 C27 1.485(5) . ? N4 C26 1.487(5) . ? C1 C2 1.517(6) . ? C2 C3 1.475(6) . ? C3 C4 1.194(6) . ? C4 C5 1.475(6) . ? C5 C6 1.524(6) . ? C7 C8 1.516(6) . ? C8 C9 1.474(6) . ? C9 C10 1.199(5) . ? C10 C11 1.481(6) . ? C11 C12 1.526(6) . ? C13 C14 1.502(6) . ? C14 C15 1.472(6) . ? C15 C16 1.197(6) . ? C16 C17 1.481(6) . ? C17 C18 1.514(6) . ? C21 C22 1.535(5) . ? C22 C23 1.470(5) . ? C23 C24 1.204(5) . ? C24 C25 1.473(6) . ? C25 C26 1.530(6) . ? C27 C28 1.528(6) . ? C28 C29 1.475(6) . ? C29 C30 1.195(6) . ? C30 C31 1.472(6) . ? C31 C32 1.533(5) . ? C33 C34 1.535(6) . ? C34 C35 1.473(6) . ? C35 C36 1.197(6) . ? C36 C37 1.480(6) . ? C37 C38 1.539(6) . ? S1 O1 1.399(4) . ? S1 O3 1.415(4) . ? S1 O2 1.418(4) . ? S1 C40 1.820(5) . ? C40 F3 1.285(5) . ? C40 F1 1.337(5) . ? C40 F2 1.344(6) . ? S2 O6 1.421(3) . ? S2 O4 1.423(3) . ? S2 O5 1.436(3) . ? S2 C41 1.812(6) . ? C41 F4 1.259(8) . ? C41 F6 1.317(7) . ? C41 F5 1.341(8) . ? C42 Cl1 1.772(12) . ? C42 Cl2 1.826(12) . ? Cl1 Cl2 0.32(2) 2_676 ? Cl1 C42 1.736(16) 2_676 ? Cl2 Cl1 0.32(2) 2_676 ? Cl2 C42 1.536(14) 2_676 ? 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 179.06(11) . . ? N2 Ag1 C15 103.87(12) . . ? N1 Ag1 C15 77.07(12) . . ? N2 Ag1 C16 76.95(12) . . ? N1 Ag1 C16 103.99(12) . . ? C15 Ag1 C16 27.01(13) . . ? N2 Ag1 C10 103.17(12) . . ? N1 Ag1 C10 76.39(12) . . ? C15 Ag1 C10 114.39(13) . . ? C16 Ag1 C10 119.23(13) . . ? N2 Ag1 C3 102.85(12) . . ? N1 Ag1 C3 76.63(12) . . ? C15 Ag1 C3 116.17(13) . . ? C16 Ag1 C3 125.27(13) . . ? C10 Ag1 C3 114.05(12) . . ? N2 Ag1 C4 76.33(12) . . ? N1 Ag1 C4 103.18(12) . . ? C15 Ag1 C4 121.17(13) . . ? C16 Ag1 C4 116.16(13) . . ? C10 Ag1 C4 122.86(12) . . ? C3 Ag1 C4 26.61(12) . . ? N2 Ag1 C9 76.57(12) . . ? N1 Ag1 C9 102.96(12) . . ? C15 Ag1 C9 123.70(13) . . ? C16 Ag1 C9 114.63(13) . . ? C10 Ag1 C9 26.70(12) . . ? C3 Ag1 C9 118.45(12) . . ? C4 Ag1 C9 113.64(12) . . ? N3 Ag2 N4 178.69(11) . . ? N3 Ag2 C35 77.35(12) . . ? N4 Ag2 C35 103.13(12) . . ? N3 Ag2 C23 77.13(12) . . ? N4 Ag2 C23 103.66(12) . . ? C35 Ag2 C23 116.49(12) . . ? N3 Ag2 C24 103.90(12) . . ? N4 Ag2 C24 76.96(12) . . ? C35 Ag2 C24 119.32(12) . . ? C23 Ag2 C24 27.04(12) . . ? N3 Ag2 C36 103.88(12) . . ? N4 Ag2 C36 76.50(12) . . ? C35 Ag2 C36 26.95(12) . . ? C23 Ag2 C36 127.63(12) . . ? C24 Ag2 C36 116.39(12) . . ? N3 Ag2 C30 76.22(12) . . ? N4 Ag2 C30 102.48(12) . . ? C35 Ag2 C30 113.61(12) . . ? C23 Ag2 C30 114.97(12) . . ? C24 Ag2 C30 125.74(12) . . ? C36 Ag2 C30 115.97(12) . . ? N3 Ag2 C29 102.29(12) . . ? N4 Ag2 C29 76.43(12) . . ? C35 Ag2 C29 124.66(12) . . ? C23 Ag2 C29 117.18(12) . . ? C24 Ag2 C29 114.41(12) . . ? C36 Ag2 C29 113.66(12) . . ? C30 Ag2 C29 26.48(12) . . ? C12 N1 C13 111.0(3) . . ? C12 N1 C1 111.5(3) . . ? C13 N1 C1 108.6(3) . . ? C12 N1 Ag1 109.6(2) . . ? C13 N1 Ag1 108.1(2) . . ? C1 N1 Ag1 107.9(2) . . ? C18 N2 C6 111.3(3) . . ? C18 N2 C7 109.9(3) . . ? C6 N2 C7 110.2(3) . . ? C18 N2 Ag1 108.0(2) . . ? C6 N2 Ag1 109.2(2) . . ? C7 N2 Ag1 108.1(2) . . ? C21 N3 C33 110.6(3) . . ? C21 N3 C32 110.5(3) . . ? C33 N3 C32 110.6(3) . . ? C21 N3 Ag2 108.3(2) . . ? C33 N3 Ag2 108.0(2) . . ? C32 N3 Ag2 108.8(2) . . ? C38 N4 C27 110.6(3) . . ? C38 N4 C26 110.0(3) . . ? C27 N4 C26 111.1(3) . . ? C38 N4 Ag2 108.7(2) . . ? C27 N4 Ag2 108.4(2) . . ? C26 N4 Ag2 108.1(2) . . ? N1 C1 C2 114.7(3) . . ? C3 C2 C1 115.1(3) . . ? C4 C3 C2 179.1(5) . . ? C4 C3 Ag1 76.9(3) . . ? C2 C3 Ag1 103.3(2) . . ? C3 C4 C5 178.1(5) . . ? C3 C4 Ag1 76.5(3) . . ? C5 C4 Ag1 103.5(3) . . ? C4 C5 C6 114.9(3) . . ? N2 C6 C5 115.0(3) . . ? N2 C7 C8 115.8(3) . . ? C9 C8 C7 114.9(3) . . ? C10 C9 C8 179.5(4) . . ? C10 C9 Ag1 76.1(2) . . ? C8 C9 Ag1 103.5(2) . . ? C9 C10 C11 178.8(4) . . ? C9 C10 Ag1 77.2(2) . . ? C11 C10 Ag1 103.0(2) . . ? C10 C11 C12 115.2(3) . . ? N1 C12 C11 115.3(4) . . ? N1 C13 C14 116.6(3) . . ? C15 C14 C13 115.1(3) . . ? C16 C15 C14 177.4(5) . . ? C16 C15 Ag1 76.6(3) . . ? C14 C15 Ag1 103.8(2) . . ? C15 C16 C17 178.8(5) . . ? C15 C16 Ag1 76.4(3) . . ? C17 C16 Ag1 103.8(2) . . ? C16 C17 C18 114.6(3) . . ? N2 C18 C17 116.1(3) . . ? N3 C21 C22 114.6(3) . . ? C23 C22 C21 114.6(3) . . ? C24 C23 C22 178.9(4) . . ? C24 C23 Ag2 76.6(2) . . ? C22 C23 Ag2 102.8(2) . . ? C23 C24 C25 178.8(4) . . ? C23 C24 Ag2 76.3(2) . . ? C25 C24 Ag2 102.9(2) . . ? C24 C25 C26 113.8(3) . . ? N4 C26 C25 114.6(3) . . ? N4 C27 C28 114.6(3) . . ? C29 C28 C27 113.9(3) . . ? C30 C29 C28 178.7(4) . . ? C30 C29 Ag2 76.7(3) . . ? C28 C29 Ag2 102.5(3) . . ? C29 C30 C31 179.6(4) . . ? C29 C30 Ag2 76.8(3) . . ? C31 C30 Ag2 102.8(2) . . ? C30 C31 C32 113.4(3) . . ? N3 C32 C31 114.2(3) . . ? N3 C33 C34 114.1(3) . . ? C35 C34 C33 113.6(3) . . ? C36 C35 C34 178.1(4) . . ? C36 C35 Ag2 77.6(3) . . ? C34 C35 Ag2 102.3(2) . . ? C35 C36 C37 178.5(4) . . ? C35 C36 Ag2 75.4(2) . . ? C37 C36 Ag2 103.8(2) . . ? C36 C37 C38 113.8(3) . . ? N4 C38 C37 114.2(3) . . ? O1 S1 O3 115.9(3) . . ? O1 S1 O2 114.9(4) . . ? O3 S1 O2 115.3(3) . . ? O1 S1 C40 101.4(2) . . ? O3 S1 C40 102.7(2) . . ? O2 S1 C40 103.8(3) . . ? F3 C40 F1 108.0(4) . . ? F3 C40 F2 107.4(5) . . ? F1 C40 F2 105.7(4) . . ? F3 C40 S1 113.3(4) . . ? F1 C40 S1 111.2(4) . . ? F2 C40 S1 110.8(3) . . ? O6 S2 O4 114.2(2) . . ? O6 S2 O5 114.0(2) . . ? O4 S2 O5 116.6(2) . . ? O6 S2 C41 102.0(3) . . ? O4 S2 C41 104.7(3) . . ? O5 S2 C41 102.9(3) . . ? F4 C41 F6 108.5(6) . . ? F4 C41 F5 104.7(6) . . ? F6 C41 F5 106.4(6) . . ? F4 C41 S2 114.5(6) . . ? F6 C41 S2 112.1(4) . . ? F5 C41 S2 110.1(4) . . ? Cl1 C42 Cl2 105.4(8) . . ? Cl2 Cl1 C42 101(3) 2_676 2_676 ? Cl2 Cl1 C42 39(3) 2_676 . ? C42 Cl1 C42 64.9(7) 2_676 . ? Cl1 Cl2 C42 133(3) 2_676 2_676 ? Cl1 Cl2 C42 69(3) 2_676 . ? C42 Cl2 C42 67.5(7) 2_676 . ? _diffrn_measured_fraction_theta_max 0.893 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.893 _refine_diff_density_max 0.962 _refine_diff_density_min -0.710 _refine_diff_density_rms 0.076 #========================================================================== data_3-Cu+ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 Cu F3 N2 O3 S' _chemical_formula_weight 481.00 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.7163(4) _cell_length_b 7.4458(3) _cell_length_c 23.4107(8) _cell_angle_alpha 90.00 _cell_angle_beta 99.8520(10) _cell_angle_gamma 90.00 _cell_volume 2012.17(13) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description platy _exptl_crystal_colour colorless _exptl_crystal_size_max .50 _exptl_crystal_size_mid .27 _exptl_crystal_size_min .04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 1.240 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14503 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.47 _reflns_number_total 3478 _reflns_number_gt 2832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The copper atom in this structure is refined with a free site occupancy factor, it refines to a partial site occupancy of 0.8. Then the structure was refined again with the copper site occupancy factor fixed to 0.81 to prevent correlation with the thermal parameters. The reason for doing so were hints from mass-spectra and NMR-spectra, that the copper position could be partially occupied by protons. Although the displacement parameters for a fully occupied copper site were not unreasonable, the refinement of a free occupancy factor reduces wR2 from more than 18% to below 7% (similary improvements can be observed for R1). The refinement of the proton-position (only 20% occupancy distributed over two positions near the two nitrogen-atoms) was clearly not seriously possible. ; _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^)+(0.0399P)^2^+0.4057P] 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 3478 _refine_ls_number_parameters 291 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0734 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.179 _refine_ls_shift/su_mean 0.009 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 0.70238(2) -0.00290(4) 0.111492(13) 0.03005(11) Uani 0.81 1 d PD A . N1 N 0.55023(13) 0.0682(2) 0.14303(6) 0.0245(3) Uani 1 1 d DU . . N2 N 0.86076(13) -0.0666(2) 0.08411(6) 0.0250(3) Uani 1 1 d . . . C1 C 0.5744(2) 0.0889(4) 0.20732(10) 0.0377(6) Uani 0.876(3) 1 d PD A 1 H1A H 0.5915 -0.0308 0.2251 0.045 Uiso 0.876(3) 1 calc PR A 1 H1B H 0.5039 0.1352 0.2203 0.045 Uiso 0.876(3) 1 calc PR A 1 C2 C 0.6744(2) 0.2136(3) 0.22911(10) 0.0490(6) Uani 1 1 d DU . . H2A H 0.6536 0.3370 0.2155 0.059 Uiso 0.876(3) 1 calc PR A 1 H2B H 0.6878 0.2148 0.2720 0.059 Uiso 0.876(3) 1 calc PR A 1 H2C H 0.6870 0.3311 0.2490 0.059 Uiso 0.124(3) 1 d PR A 2 H2D H 0.6571 0.1247 0.2579 0.059 Uiso 0.124(3) 1 d PR A 2 C3 C 0.7819(2) 0.1601(3) 0.20929(9) 0.0386(5) Uani 1 1 d D A . C4 C 0.87005(19) 0.1124(3) 0.19532(9) 0.0377(5) Uani 1 1 d . . . C5 C 0.97610(19) 0.0478(4) 0.17759(10) 0.0533(7) Uani 1 1 d . A . H5A H 1.0302 0.0064 0.2123 0.064 Uiso 1 1 calc R . . H5B H 1.0135 0.1483 0.1602 0.064 Uiso 1 1 calc R . . C6 C 0.95409(17) -0.1052(3) 0.13411(9) 0.0422(6) Uani 1 1 d . A . H6A H 1.0267 -0.1313 0.1194 0.051 Uiso 1 1 calc R . . H6B H 0.9330 -0.2142 0.1542 0.051 Uiso 1 1 calc R . . C7 C 0.89748(17) 0.0889(3) 0.05143(8) 0.0297(4) Uani 1 1 d . A . H7A H 0.9703 0.0574 0.0377 0.036 Uiso 1 1 calc R . . H7B H 0.9139 0.1925 0.0781 0.036 Uiso 1 1 calc R . . C8 C 0.80729(18) 0.1445(3) -0.00037(9) 0.0361(5) Uani 1 1 d . . . H8A H 0.8334 0.2551 -0.0177 0.043 Uiso 1 1 calc R A . H8B H 0.7994 0.0486 -0.0301 0.043 Uiso 1 1 calc R . . C9 C 0.69447(18) 0.1769(3) 0.01690(8) 0.0312(5) Uani 1 1 d . A . C10 C 0.60421(18) 0.2073(3) 0.03226(8) 0.0315(5) Uani 1 1 d D . . C11 C 0.49358(17) 0.2478(3) 0.05110(9) 0.0372(5) Uani 1 1 d DU A . H11A H 0.4344 0.1601 0.0334 0.045 Uiso 0.876(3) 1 calc PR A 1 H11B H 0.4673 0.3689 0.0372 0.045 Uiso 0.876(3) 1 calc PR A 1 H11C H 0.4323 0.2588 0.0165 0.045 Uiso 0.124(3) 1 d PR A 2 H11D H 0.5001 0.3649 0.0714 0.045 Uiso 0.124(3) 1 d PR A 2 C12 C 0.5038(2) 0.2408(3) 0.11691(10) 0.0340(6) Uani 0.876(3) 1 d PD A 1 H12A H 0.5550 0.3397 0.1341 0.041 Uiso 0.876(3) 1 calc PR A 1 H12B H 0.4262 0.2615 0.1271 0.041 Uiso 0.876(3) 1 calc PR A 1 C13 C 0.46057(19) -0.0727(3) 0.12791(11) 0.0328(6) Uani 0.876(3) 1 d PD A 1 H13A H 0.4307 -0.0669 0.0857 0.039 Uiso 0.876(3) 1 calc PR A 1 H13B H 0.3951 -0.0468 0.1484 0.039 Uiso 0.876(3) 1 calc PR A 1 C14 C 0.50401(18) -0.2630(3) 0.14325(10) 0.0363(5) Uani 1 1 d DU . . H14A H 0.5200 -0.2764 0.1859 0.044 Uiso 0.876(3) 1 calc PR A 1 H14B H 0.4427 -0.3500 0.1276 0.044 Uiso 0.876(3) 1 calc PR A 1 H14C H 0.4909 -0.3589 0.1707 0.044 Uiso 0.124(3) 1 d PR A 2 H14D H 0.4371 -0.2627 0.1111 0.044 Uiso 0.124(3) 1 d PR A 2 C15 C 0.60978(17) -0.3046(3) 0.11982(9) 0.0309(5) Uani 1 1 d D A . C16 C 0.69294(17) -0.3428(3) 0.09947(9) 0.0335(5) Uani 1 1 d . . . C17 C 0.79494(19) -0.3895(3) 0.07357(11) 0.0449(6) Uani 1 1 d . A . H17A H 0.7732 -0.4835 0.0438 0.054 Uiso 1 1 calc R . . H17B H 0.8557 -0.4397 0.1040 0.054 Uiso 1 1 calc R . . C18 C 0.84390(18) -0.2278(3) 0.04576(9) 0.0348(5) Uani 1 1 d . A . H18A H 0.9193 -0.2616 0.0351 0.042 Uiso 1 1 calc R . . H18B H 0.7906 -0.1964 0.0096 0.042 Uiso 1 1 calc R . . S1 S 0.17561(4) 0.40713(7) 0.10568(2) 0.03199(14) Uani 1 1 d . . . O1 O 0.18590(13) 0.2159(2) 0.11226(7) 0.0453(4) Uani 1 1 d . . . O2 O 0.06038(14) 0.4708(2) 0.08593(9) 0.0631(5) Uani 1 1 d . . . O3 O 0.26407(14) 0.4889(2) 0.07860(7) 0.0461(4) Uani 1 1 d . . . C20 C 0.2085(2) 0.4895(3) 0.17957(11) 0.0516(6) Uani 1 1 d . . . F1 F 0.13190(17) 0.4350(3) 0.21120(8) 0.1044(7) Uani 1 1 d . . . F2 F 0.31223(14) 0.4375(3) 0.20612(6) 0.0768(5) Uani 1 1 d . . . F3 F 0.20947(16) 0.6690(2) 0.18093(8) 0.0926(6) Uani 1 1 d . . . C1B C 0.5696(12) 0.2284(18) 0.1808(6) 0.036(3) Uani 0.124(3) 1 d PDU A 2 H1B1 H 0.4997 0.2493 0.1984 0.043 Uiso 0.124(3) 1 calc PR A 2 H1B2 H 0.5799 0.3343 0.1566 0.043 Uiso 0.124(3) 1 calc PR A 2 C12B C 0.4583(10) 0.1072(19) 0.0906(5) 0.028(3) Uani 0.124(3) 1 d PDU A 2 H12C H 0.4400 -0.0053 0.0684 0.034 Uiso 0.124(3) 1 calc PR A 2 H12D H 0.3868 0.1474 0.1041 0.034 Uiso 0.124(3) 1 calc PR A 2 C13B C 0.5092(14) -0.0848(15) 0.1740(6) 0.032(3) Uani 0.124(3) 1 d PDU A 2 H13C H 0.4308 -0.0562 0.1817 0.039 Uiso 0.124(3) 1 calc PR A 2 H13D H 0.5608 -0.0974 0.2120 0.039 Uiso 0.124(3) 1 calc PR 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 Cu1 0.02364(17) 0.03228(18) 0.03619(18) -0.00128(13) 0.01065(13) 0.00371(12) N1 0.0254(8) 0.0198(7) 0.0281(8) -0.0018(6) 0.0038(7) 0.0017(6) N2 0.0248(8) 0.0235(8) 0.0266(9) 0.0010(7) 0.0040(7) -0.0007(7) C1 0.0391(14) 0.0464(16) 0.0295(13) -0.0050(12) 0.0112(11) 0.0071(12) C2 0.0523(15) 0.0508(15) 0.0401(13) -0.0213(11) -0.0028(10) 0.0071(11) C3 0.0486(14) 0.0324(12) 0.0303(12) -0.0050(9) -0.0064(10) -0.0114(11) C4 0.0417(13) 0.0425(13) 0.0263(11) -0.0006(9) -0.0018(10) -0.0172(11) C5 0.0323(12) 0.093(2) 0.0330(12) -0.0004(13) 0.0002(10) -0.0184(13) C6 0.0250(11) 0.0658(16) 0.0354(12) 0.0098(11) 0.0043(9) 0.0086(11) C7 0.0317(11) 0.0275(11) 0.0327(11) 0.0006(9) 0.0136(9) -0.0039(9) C8 0.0491(13) 0.0326(11) 0.0299(11) 0.0049(9) 0.0162(10) 0.0064(10) C9 0.0420(12) 0.0242(10) 0.0262(10) 0.0005(8) 0.0020(9) 0.0015(9) C10 0.0388(12) 0.0251(11) 0.0285(11) 0.0026(8) 0.0002(9) -0.0005(9) C11 0.0310(11) 0.0356(12) 0.0432(12) 0.0115(9) 0.0014(10) 0.0044(9) C12 0.0326(13) 0.0257(12) 0.0453(15) 0.0024(11) 0.0112(11) 0.0072(10) C13 0.0222(12) 0.0299(13) 0.0474(16) 0.0008(11) 0.0091(11) -0.0028(10) C14 0.0373(12) 0.0245(10) 0.0504(13) -0.0006(9) 0.0173(10) -0.0059(9) C15 0.0317(11) 0.0202(10) 0.0402(12) 0.0005(9) 0.0045(9) -0.0036(8) C16 0.0346(12) 0.0190(10) 0.0470(13) -0.0001(9) 0.0076(10) -0.0037(9) C17 0.0405(12) 0.0229(11) 0.0757(17) -0.0028(11) 0.0222(12) 0.0033(9) C18 0.0358(12) 0.0248(11) 0.0474(13) -0.0064(9) 0.0169(10) 0.0014(9) S1 0.0247(3) 0.0304(3) 0.0402(3) -0.0014(2) 0.0033(2) 0.0012(2) O1 0.0515(10) 0.0303(8) 0.0570(10) -0.0001(7) 0.0178(8) -0.0022(7) O2 0.0300(9) 0.0663(12) 0.0861(14) -0.0163(10) -0.0102(9) 0.0119(8) O3 0.0433(9) 0.0459(10) 0.0495(9) 0.0124(7) 0.0088(7) -0.0071(7) C20 0.0427(14) 0.0576(17) 0.0559(16) -0.0165(13) 0.0122(12) -0.0035(12) F1 0.0973(14) 0.1547(19) 0.0755(12) -0.0480(13) 0.0554(11) -0.0382(13) F2 0.0670(11) 0.1092(14) 0.0462(9) -0.0079(9) -0.0132(8) 0.0071(9) F3 0.0988(14) 0.0615(12) 0.1100(15) -0.0470(10) -0.0034(11) 0.0037(9) C1B 0.045(9) 0.027(5) 0.034(8) -0.009(5) 0.004(4) -0.002(7) C12B 0.019(7) 0.036(9) 0.029(6) 0.000(4) 0.004(4) 0.001(5) C13B 0.038(9) 0.028(5) 0.032(8) 0.001(3) 0.011(6) -0.003(6) _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 N1 2.1104(15) . ? Cu1 N2 2.1182(15) . ? Cu1 C15 2.5164(19) . ? Cu1 C10 2.5459(19) . ? Cu1 C16 2.5464(19) . ? N1 C13B 1.474(12) . ? N1 C1B 1.479(12) . ? N1 C13 1.484(3) . ? N1 C12 1.486(3) . ? N1 C1 1.491(3) . ? N1 C12B 1.516(11) . ? N2 C6 1.487(2) . ? N2 C7 1.491(2) . ? N2 C18 1.492(2) . ? C1 C2 1.513(3) . ? C2 C3 1.470(3) . ? C2 C1B 1.524(12) . ? C3 C4 1.189(3) . ? C4 C5 1.457(3) . ? C5 C6 1.520(3) . ? C7 C8 1.523(3) . ? C8 C9 1.467(3) . ? C9 C10 1.195(3) . ? C10 C11 1.470(3) . ? C11 C12B 1.501(12) . ? C11 C12 1.526(3) . ? C13 C14 1.527(3) . ? C14 C15 1.471(3) . ? C14 C13B 1.505(12) . ? C15 C16 1.190(3) . ? C16 C17 1.471(3) . ? C17 C18 1.526(3) . ? S1 O2 1.4311(16) . ? S1 O1 1.4348(16) . ? S1 O3 1.4392(16) . ? S1 C20 1.814(3) . ? C20 F1 1.321(3) . ? C20 F2 1.325(3) . ? C20 F3 1.337(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 N1 Cu1 N2 176.64(6) . . ? N1 Cu1 C15 78.21(6) . . ? N2 Cu1 C15 103.60(6) . . ? N1 Cu1 C10 78.31(6) . . ? N2 Cu1 C10 103.13(6) . . ? C15 Cu1 C10 117.26(7) . . ? N1 Cu1 C16 105.35(6) . . ? N2 Cu1 C16 76.57(6) . . ? C15 Cu1 C16 27.18(6) . . ? C10 Cu1 C16 121.64(6) . . ? C13B N1 C1B 111.1(8) . . ? C13B N1 C13 45.1(6) . . ? C1B N1 C13 138.0(6) . . ? C13B N1 C12 138.0(6) . . ? C1B N1 C12 63.7(6) . . ? C13 N1 C12 108.59(16) . . ? C13B N1 C1 66.8(6) . . ? C1B N1 C1 47.9(6) . . ? C13 N1 C1 108.57(17) . . ? C12 N1 C1 108.60(17) . . ? C13B N1 C12B 107.4(8) . . ? C1B N1 C12B 110.1(8) . . ? C13 N1 C12B 64.3(5) . . ? C12 N1 C12B 48.8(6) . . ? C1 N1 C12B 141.5(6) . . ? C13B N1 Cu1 110.1(6) . . ? C1B N1 Cu1 111.0(6) . . ? C13 N1 Cu1 110.17(12) . . ? C12 N1 Cu1 110.18(12) . . ? C1 N1 Cu1 110.68(12) . . ? C12B N1 Cu1 106.9(5) . . ? C6 N2 C7 108.43(15) . . ? C6 N2 C18 108.79(16) . . ? C7 N2 C18 109.65(15) . . ? C6 N2 Cu1 111.68(12) . . ? C7 N2 Cu1 109.02(11) . . ? C18 N2 Cu1 109.25(11) . . ? N1 C1 C2 113.97(19) . . ? C3 C2 C1 112.54(18) . . ? C3 C2 C1B 114.2(6) . . ? C1 C2 C1B 46.8(6) . . ? C4 C3 C2 177.2(2) . . ? C3 C4 C5 178.0(2) . . ? C4 C5 C6 112.50(18) . . ? N2 C6 C5 113.57(19) . . ? N2 C7 C8 113.44(16) . . ? C9 C8 C7 111.11(16) . . ? C10 C9 C8 177.9(2) . . ? C9 C10 C11 179.1(2) . . ? C9 C10 Cu1 77.89(13) . . ? C11 C10 Cu1 102.66(12) . . ? C10 C11 C12B 113.1(5) . . ? C10 C11 C12 112.05(17) . . ? C12B C11 C12 48.4(5) . . ? N1 C12 C11 113.87(18) . . ? N1 C13 C14 113.95(18) . . ? C15 C14 C13B 113.3(6) . . ? C15 C14 C13 112.05(17) . . ? C13B C14 C13 43.9(6) . . ? C16 C15 C14 177.5(2) . . ? C16 C15 Cu1 77.81(13) . . ? C14 C15 Cu1 104.05(12) . . ? C15 C16 C17 179.3(2) . . ? C15 C16 Cu1 75.01(13) . . ? C17 C16 Cu1 104.94(12) . . ? C16 C17 C18 112.34(17) . . ? N2 C18 C17 113.50(17) . . ? O2 S1 O1 114.89(10) . . ? O2 S1 O3 115.35(11) . . ? O1 S1 O3 114.42(9) . . ? O2 S1 C20 103.33(11) . . ? O1 S1 C20 103.46(11) . . ? O3 S1 C20 103.04(11) . . ? F1 C20 F2 107.7(2) . . ? F1 C20 F3 107.3(2) . . ? F2 C20 F3 106.1(2) . . ? F1 C20 S1 112.14(17) . . ? F2 C20 S1 112.13(17) . . ? F3 C20 S1 111.1(2) . . ? N1 C1B C2 114.0(9) . . ? C11 C12B N1 113.6(8) . . ? N1 C13B C14 115.9(9) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.47 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.310 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.042 #==========================================================================