Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Parimal K. Bharadwaj' _publ_contact_author_address ; Department of Chemistry Indian Institute of Technology Kanpur Kanpur 208016 INDIA ; _publ_contact_author_email PKB@IITK.AC.IN _publ_section_title ; Reversible binding of HgCl2 by tripodals controlled by AgPF6: receptors for the PF6? anion ; loop_ _publ_author_name 'Parimal Bharadwaj' 'Ashutosh S. Singh' data_Compound1 _database_code_depnum_ccdc_archive 'CCDC 657109' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 Cl2 Hg N4 O3' _chemical_formula_sum 'C27 H24 Cl2 Hg N4 O3' _chemical_formula_weight 723.99 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall -P2yn _symmetry_Int_Tables_number 14 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 7.828(5) _cell_length_b 24.454(5) _cell_length_c 14.274(5) _cell_angle_alpha 90 _cell_angle_beta 102.386(5) _cell_angle_gamma 90 _cell_volume 2669(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min -28.0 _cell_measurement_theta_max +28.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.802 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 6.004 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4662 _exptl_absorpt_correction_T_max 0.6141 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD _diffrn_measurement_method phi-omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17724 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0917 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 28.39 _reflns_number_total 6596 _reflns_number_gt 4824 _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^)+(0.0056P)^2^+37.7152P] 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 6596 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.0895 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.005 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 Hg Hg -0.12997(4) 0.466899(13) 0.86431(2) 0.01700(9) Uani 1 1 d . . . Cl1 Cl -0.4108(3) 0.43205(9) 0.83864(14) 0.0230(4) Uani 1 1 d . . . Cl2 Cl 0.1270(3) 0.51678(9) 0.90569(16) 0.0253(5) Uani 1 1 d . . . O1 O -0.0944(7) 0.4504(2) 0.6620(4) 0.0192(12) Uani 1 1 d . . . O2 O 0.0847(8) 0.3049(2) 1.0228(4) 0.0221(13) Uani 1 1 d . . . O3 O 0.0007(7) 0.2745(2) 0.7058(4) 0.0181(12) Uani 1 1 d . . . N1 N 0.0336(8) 0.3788(3) 0.8356(5) 0.0150(14) Uani 1 1 d . . . N2 N -0.2494(11) 0.5644(3) 0.7474(6) 0.0346(19) Uani 1 1 d . . . N3 N 0.0812(12) 0.1702(3) 0.9713(6) 0.038(2) Uani 1 1 d . . . N4 N 0.0876(11) 0.3195(3) 0.4947(5) 0.0321(19) Uani 1 1 d . . . C1 C 0.1157(10) 0.3899(3) 0.7546(6) 0.0168(16) Uani 1 1 d . . . H1A H 0.1923 0.3586 0.7480 0.020 Uiso 1 1 calc R . . H1B H 0.1921 0.4223 0.7709 0.020 Uiso 1 1 calc R . . C2 C -0.0024(11) 0.3999(3) 0.6586(6) 0.0192(17) Uani 1 1 d . . . H2A H 0.0675 0.4020 0.6085 0.023 Uiso 1 1 calc R . . H2B H -0.0868 0.3695 0.6425 0.023 Uiso 1 1 calc R . . C3 C -0.1727(10) 0.4727(3) 0.5763(5) 0.0185(17) Uani 1 1 d . . . C4 C -0.1791(11) 0.4487(4) 0.4867(6) 0.0220(18) Uani 1 1 d . . . H4 H -0.1258 0.4141 0.4829 0.026 Uiso 1 1 calc R . . C5 C -0.2622(11) 0.4748(4) 0.4038(6) 0.027(2) Uani 1 1 d . . . H5 H -0.2661 0.4582 0.3432 0.033 Uiso 1 1 calc R . . C6 C -0.3403(10) 0.5254(4) 0.4086(6) 0.0230(19) Uani 1 1 d . . . H6 H -0.3967 0.5433 0.3511 0.028 Uiso 1 1 calc R . . C7 C -0.3372(11) 0.5501(4) 0.4956(6) 0.025(2) Uani 1 1 d . . . H7 H -0.3903 0.5848 0.4984 0.030 Uiso 1 1 calc R . . C8 C -0.2549(10) 0.5234(3) 0.5800(6) 0.0187(17) Uani 1 1 d . . . C9 C -0.2517(10) 0.5475(3) 0.6727(6) 0.0208(18) Uani 1 1 d . . . C10 C 0.1745(10) 0.3721(3) 0.9216(5) 0.0156(16) Uani 1 1 d . . . H10A H 0.2486 0.4053 0.9292 0.019 Uiso 1 1 calc R . . H10B H 0.2486 0.3409 0.9109 0.019 Uiso 1 1 calc R . . C11 C 0.1142(10) 0.3624(3) 1.0149(5) 0.0166(16) Uani 1 1 d . . . H11A H 0.2048 0.3751 1.0701 0.020 Uiso 1 1 calc R . . H11B H 0.0050 0.3829 1.0144 0.020 Uiso 1 1 calc R . . C12 C 0.0447(10) 0.2860(4) 1.1057(6) 0.0190(17) Uani 1 1 d . . . C13 C 0.0300(10) 0.2289(3) 1.1118(6) 0.0197(18) Uani 1 1 d . . . C14 C -0.0113(10) 0.2058(4) 1.1926(6) 0.025(2) Uani 1 1 d . . . H14 H -0.0216 0.1672 1.1973 0.030 Uiso 1 1 calc R . . C15 C -0.0375(11) 0.2392(4) 1.2667(6) 0.025(2) Uani 1 1 d . . . H15 H -0.0677 0.2235 1.3218 0.031 Uiso 1 1 calc R . . C16 C -0.0199(11) 0.2947(4) 1.2608(6) 0.028(2) Uani 1 1 d . . . H16 H -0.0371 0.3171 1.3123 0.033 Uiso 1 1 calc R . . C17 C 0.0226(10) 0.3189(4) 1.1805(6) 0.0219(18) Uani 1 1 d . . . H17 H 0.0361 0.3574 1.1774 0.026 Uiso 1 1 calc R . . C18 C 0.0590(12) 0.1957(4) 1.0332(7) 0.027(2) Uani 1 1 d . . . C19 C -0.0927(10) 0.3332(3) 0.8187(5) 0.0161(16) Uani 1 1 d . . . H19A H -0.1861 0.3433 0.7629 0.019 Uiso 1 1 calc R . . H19B H -0.1476 0.3312 0.8749 0.019 Uiso 1 1 calc R . . C20 C -0.0329(11) 0.2763(3) 0.8008(6) 0.0196(17) Uani 1 1 d . . . H20A H 0.0748 0.2671 0.8486 0.023 Uiso 1 1 calc R . . H20B H -0.1245 0.2494 0.8067 0.023 Uiso 1 1 calc R . . C21 C 0.0312(10) 0.2242(4) 0.6687(6) 0.0189(17) Uani 1 1 d . . . C22 C 0.0289(10) 0.1749(3) 0.7151(6) 0.0175(17) Uani 1 1 d . . . H22 H 0.0071 0.1735 0.7780 0.021 Uiso 1 1 calc R . . C23 C 0.0589(11) 0.1275(4) 0.6686(6) 0.0240(19) Uani 1 1 d . . . H23 H 0.0567 0.0934 0.7004 0.029 Uiso 1 1 calc R . . C24 C 0.0922(10) 0.1280(3) 0.5771(6) 0.0200(18) Uani 1 1 d . . . H24 H 0.1098 0.0947 0.5461 0.024 Uiso 1 1 calc R . . C25 C 0.0995(10) 0.1774(4) 0.5316(6) 0.0218(19) Uani 1 1 d . . . H25 H 0.1244 0.1782 0.4694 0.026 Uiso 1 1 calc R . . C26 C 0.0704(10) 0.2266(3) 0.5765(6) 0.0158(16) Uani 1 1 d . . . C27 C 0.0793(11) 0.2788(4) 0.5315(6) 0.0210(19) 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 Hg 0.01652(15) 0.01565(16) 0.01872(15) -0.00149(14) 0.00356(10) -0.00109(14) Cl1 0.0163(9) 0.0302(12) 0.0222(10) -0.0001(9) 0.0034(7) -0.0021(9) Cl2 0.0213(10) 0.0202(11) 0.0354(12) -0.0059(9) 0.0083(9) -0.0056(9) O1 0.026(3) 0.016(3) 0.015(3) -0.003(2) 0.003(2) 0.002(2) O2 0.030(3) 0.013(3) 0.022(3) 0.002(2) 0.005(2) -0.001(3) O3 0.029(3) 0.005(3) 0.021(3) -0.002(2) 0.009(2) 0.003(2) N1 0.007(3) 0.014(3) 0.025(3) 0.001(3) 0.003(2) 0.002(3) N2 0.043(5) 0.029(5) 0.031(4) 0.002(4) 0.004(4) 0.006(4) N3 0.056(6) 0.024(5) 0.041(5) 0.001(4) 0.028(4) 0.010(4) N4 0.048(5) 0.026(5) 0.021(4) 0.001(4) 0.005(3) 0.002(4) C1 0.010(3) 0.008(4) 0.033(4) -0.006(3) 0.006(3) -0.001(3) C2 0.024(4) 0.008(4) 0.027(4) -0.001(3) 0.010(3) 0.003(3) C3 0.018(4) 0.017(4) 0.019(4) 0.000(3) 0.001(3) -0.013(3) C4 0.023(4) 0.018(4) 0.028(4) -0.002(4) 0.013(3) -0.002(4) C5 0.025(4) 0.032(6) 0.022(4) -0.001(4) -0.002(3) -0.003(4) C6 0.018(4) 0.030(5) 0.019(4) 0.010(4) 0.000(3) 0.001(4) C7 0.017(4) 0.024(5) 0.032(5) 0.009(4) -0.002(3) 0.003(4) C8 0.019(4) 0.014(4) 0.027(4) -0.002(3) 0.013(3) -0.002(3) C9 0.017(4) 0.014(4) 0.030(5) 0.003(4) 0.002(3) 0.002(3) C10 0.022(4) 0.013(4) 0.016(4) 0.001(3) 0.011(3) -0.003(3) C11 0.019(4) 0.017(4) 0.015(4) -0.002(3) 0.005(3) 0.000(3) C12 0.012(4) 0.027(5) 0.019(4) 0.003(3) 0.004(3) 0.003(3) C13 0.012(4) 0.016(4) 0.031(5) 0.006(4) 0.004(3) 0.007(3) C14 0.011(4) 0.023(5) 0.035(5) 0.009(4) -0.011(3) -0.006(3) C15 0.025(5) 0.028(5) 0.022(4) 0.010(4) 0.001(3) -0.007(4) C16 0.023(4) 0.045(6) 0.012(4) -0.004(4) -0.003(3) -0.001(4) C17 0.017(4) 0.025(5) 0.021(4) 0.001(4) -0.001(3) -0.004(4) C18 0.026(5) 0.012(4) 0.043(6) 0.015(4) 0.006(4) -0.004(4) C19 0.017(4) 0.021(4) 0.010(3) 0.001(3) 0.004(3) -0.003(3) C20 0.018(4) 0.017(4) 0.025(4) 0.002(3) 0.005(3) -0.007(3) C21 0.015(4) 0.023(5) 0.021(4) -0.002(3) 0.006(3) 0.004(3) C22 0.016(4) 0.019(4) 0.019(4) -0.002(3) 0.008(3) 0.010(3) C23 0.021(4) 0.022(5) 0.027(5) 0.000(4) 0.002(3) 0.004(4) C24 0.014(4) 0.017(4) 0.027(4) -0.010(4) -0.003(3) 0.007(3) C25 0.008(4) 0.027(5) 0.028(4) -0.010(4) -0.002(3) -0.009(3) C26 0.013(4) 0.011(4) 0.022(4) -0.001(3) 0.001(3) -0.005(3) C27 0.019(4) 0.030(5) 0.015(4) -0.008(4) 0.003(3) 0.011(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 Hg Cl1 2.312(2) . ? Hg Cl2 2.318(2) . ? Hg N1 2.583(6) . ? O1 C3 1.360(9) . ? O1 C2 1.436(9) . ? O2 C12 1.367(9) . ? O2 C11 1.434(9) . ? O3 C21 1.380(9) . ? O3 C20 1.436(9) . ? N1 C1 1.465(10) . ? N1 C10 1.473(10) . ? N1 C19 1.475(10) . ? N2 C9 1.140(11) . ? N3 C18 1.125(12) . ? N4 C27 1.132(11) . ? C1 C2 1.499(11) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.404(11) . ? C3 C4 1.398(11) . ? C4 C5 1.379(12) . ? C4 H4 0.9500 . ? C5 C6 1.388(13) . ? C5 H5 0.9500 . ? C6 C7 1.376(12) . ? C6 H6 0.9500 . ? C7 C8 1.399(11) . ? C7 H7 0.9500 . ? C8 C9 1.444(11) . ? C10 C11 1.523(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.378(11) . ? C12 C13 1.403(12) . ? C13 C14 1.385(12) . ? C13 C18 1.443(13) . ? C14 C15 1.385(13) . ? C14 H14 0.9500 . ? C15 C16 1.370(13) . ? C15 H15 0.9500 . ? C16 C17 1.392(12) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C19 C20 1.507(11) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.377(11) . ? C21 C26 1.416(11) . ? C22 C23 1.381(11) . ? C22 H22 0.9500 . ? C23 C24 1.386(12) . ? C23 H23 0.9500 . ? C24 C25 1.379(12) . ? C24 H24 0.9500 . ? C25 C26 1.402(11) . ? C25 H25 0.9500 . ? C26 C27 1.439(12) . ? 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 Cl1 Hg Cl2 167.91(8) . . ? Cl1 Hg N1 98.86(15) . . ? Cl2 Hg N1 92.68(15) . . ? C3 O1 C2 116.5(6) . . ? C12 O2 C11 118.1(6) . . ? C21 O3 C20 118.1(6) . . ? C1 N1 C10 107.6(6) . . ? C1 N1 C19 113.8(6) . . ? C10 N1 C19 114.1(6) . . ? C1 N1 Hg 106.7(5) . . ? C10 N1 Hg 105.6(5) . . ? C19 N1 Hg 108.6(4) . . ? N1 C1 C2 117.6(6) . . ? N1 C1 H1A 107.9 . . ? C2 C1 H1A 107.9 . . ? N1 C1 H1B 107.9 . . ? C2 C1 H1B 107.9 . . ? H1A C1 H1B 107.2 . . ? O1 C2 C1 109.0(6) . . ? O1 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? O1 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? O1 C3 C8 116.2(7) . . ? O1 C3 C4 125.2(8) . . ? C8 C3 C4 118.6(7) . . ? C5 C4 C3 120.5(8) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.2(8) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.9(8) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 119.2(8) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C7 C8 C3 120.6(8) . . ? C7 C8 C9 120.9(8) . . ? C3 C8 C9 118.5(7) . . ? N2 C9 C8 177.2(9) . . ? N1 C10 C11 115.4(6) . . ? N1 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? N1 C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? O2 C11 C10 107.9(6) . . ? O2 C11 H11A 110.1 . . ? C10 C11 H11A 110.1 . . ? O2 C11 H11B 110.1 . . ? C10 C11 H11B 110.1 . . ? H11A C11 H11B 108.4 . . ? C17 C12 O2 124.2(8) . . ? C17 C12 C13 120.5(8) . . ? O2 C12 C13 115.3(7) . . ? C14 C13 C12 119.7(8) . . ? C14 C13 C18 121.4(8) . . ? C12 C13 C18 118.9(7) . . ? C15 C14 C13 119.6(8) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C14 120.3(8) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 121.2(9) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C12 C17 C16 118.7(9) . . ? C12 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? N3 C18 C13 179.3(10) . . ? N1 C19 C20 120.3(6) . . ? N1 C19 H19A 107.3 . . ? C20 C19 H19A 107.3 . . ? N1 C19 H19B 107.3 . . ? C20 C19 H19B 107.3 . . ? H19A C19 H19B 106.9 . . ? O3 C20 C19 108.3(6) . . ? O3 C20 H20A 110.0 . . ? C19 C20 H20A 110.0 . . ? O3 C20 H20B 110.0 . . ? C19 C20 H20B 110.0 . . ? H20A C20 H20B 108.4 . . ? C22 C21 O3 125.1(7) . . ? C22 C21 C26 120.7(7) . . ? O3 C21 C26 114.2(7) . . ? C21 C22 C23 118.9(8) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C22 C23 C24 122.0(8) . . ? C22 C23 H23 119.0 . . ? C24 C23 H23 119.0 . . ? C25 C24 C23 119.1(8) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C24 C25 C26 120.6(8) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C25 C26 C21 118.6(8) . . ? C25 C26 C27 122.0(7) . . ? C21 C26 C27 119.5(7) . . ? N4 C27 C26 178.6(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 Cl1 Hg N1 C1 119.3(4) . . . . ? Cl2 Hg N1 C1 -64.4(4) . . . . ? Cl1 Hg N1 C10 -126.5(4) . . . . ? Cl2 Hg N1 C10 49.9(4) . . . . ? Cl1 Hg N1 C19 -3.8(5) . . . . ? Cl2 Hg N1 C19 172.6(4) . . . . ? C10 N1 C1 C2 -178.3(7) . . . . ? C19 N1 C1 C2 54.3(9) . . . . ? Hg N1 C1 C2 -65.4(7) . . . . ? C3 O1 C2 C1 164.0(6) . . . . ? N1 C1 C2 O1 67.1(9) . . . . ? C2 O1 C3 C8 -176.9(7) . . . . ? C2 O1 C3 C4 4.1(11) . . . . ? O1 C3 C4 C5 180.0(7) . . . . ? C8 C3 C4 C5 1.0(12) . . . . ? C3 C4 C5 C6 0.1(13) . . . . ? C4 C5 C6 C7 -0.4(13) . . . . ? C5 C6 C7 C8 -0.4(13) . . . . ? C6 C7 C8 C3 1.5(12) . . . . ? C6 C7 C8 C9 -178.8(8) . . . . ? O1 C3 C8 C7 179.1(7) . . . . ? C4 C3 C8 C7 -1.8(12) . . . . ? O1 C3 C8 C9 -0.6(11) . . . . ? C4 C3 C8 C9 178.6(7) . . . . ? C7 C8 C9 N2 147(19) . . . . ? C3 C8 C9 N2 -33(19) . . . . ? C1 N1 C10 C11 177.6(6) . . . . ? C19 N1 C10 C11 -55.1(9) . . . . ? Hg N1 C10 C11 64.0(7) . . . . ? C12 O2 C11 C10 174.2(6) . . . . ? N1 C10 C11 O2 85.9(8) . . . . ? C11 O2 C12 C17 3.3(11) . . . . ? C11 O2 C12 C13 -175.5(7) . . . . ? C17 C12 C13 C14 1.6(12) . . . . ? O2 C12 C13 C14 -179.6(7) . . . . ? C17 C12 C13 C18 -178.2(8) . . . . ? O2 C12 C13 C18 0.6(11) . . . . ? C12 C13 C14 C15 -0.1(12) . . . . ? C18 C13 C14 C15 179.7(8) . . . . ? C13 C14 C15 C16 -1.0(12) . . . . ? C14 C15 C16 C17 0.6(13) . . . . ? O2 C12 C17 C16 179.3(7) . . . . ? C13 C12 C17 C16 -2.0(12) . . . . ? C15 C16 C17 C12 0.9(12) . . . . ? C14 C13 C18 N3 156(85) . . . . ? C12 C13 C18 N3 -24(85) . . . . ? C1 N1 C19 C20 62.0(9) . . . . ? C10 N1 C19 C20 -61.9(9) . . . . ? Hg N1 C19 C20 -179.3(5) . . . . ? C21 O3 C20 C19 -170.3(6) . . . . ? N1 C19 C20 O3 -73.5(8) . . . . ? C20 O3 C21 C22 1.3(11) . . . . ? C20 O3 C21 C26 -177.4(6) . . . . ? O3 C21 C22 C23 178.9(7) . . . . ? C26 C21 C22 C23 -2.5(12) . . . . ? C21 C22 C23 C24 0.4(12) . . . . ? C22 C23 C24 C25 1.4(12) . . . . ? C23 C24 C25 C26 -1.2(11) . . . . ? C24 C25 C26 C21 -0.9(11) . . . . ? C24 C25 C26 C27 179.2(7) . . . . ? C22 C21 C26 C25 2.7(11) . . . . ? O3 C21 C26 C25 -178.5(7) . . . . ? C22 C21 C26 C27 -177.3(7) . . . . ? O3 C21 C26 C27 1.4(10) . . . . ? C25 C26 C27 N4 -10(40) . . . . ? C21 C26 C27 N4 170(40) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 2.207 _refine_diff_density_min -1.730 _refine_diff_density_rms 0.294 # Attachment 'Compound 2, old CCDC no 657110.doc' data_compound2.CIF _database_code_depnum_ccdc_archive 'CCDC 657110' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 Cl2 Hg N4 O3' _chemical_formula_sum 'C27 H24 Cl2 Hg N4 O3' _chemical_formula_weight 723.99 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' Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc _symmetry_Int_Tables_number 14 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 11.6156(9) _cell_length_b 16.1637(13) _cell_length_c 14.9583(12) _cell_angle_alpha 90 _cell_angle_beta 107.491(1) _cell_angle_gamma 90 _cell_volume 2678.7(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min -28.0 _cell_measurement_theta_max +28.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 5.982 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4673 _exptl_absorpt_correction_T_max 0.6151 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method phi-omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17500 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6631 _reflns_number_gt 5311 _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^)+(0.0000P)^2^+67.6994P] 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 6631 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1546 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.266 _refine_ls_restrained_S_all 1.266 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Hg Hg 0.51209(3) 0.30353(2) 0.16784(3) 0.01946(11) Uani 1 1 d . . . Cl1 Cl 0.5704(2) 0.29028(19) 0.03436(19) 0.0307(6) Uani 1 1 d . . . Cl2 Cl 0.4005(2) 0.33384(16) 0.26915(19) 0.0248(5) Uani 1 1 d . . . O1 O 0.8637(6) 0.0741(4) 0.3035(5) 0.0245(16) Uani 1 1 d . . . O2 O 0.7091(6) 0.3993(4) 0.2729(5) 0.0166(14) Uani 1 1 d . . . O3 O 0.4774(6) 0.1313(4) 0.1640(5) 0.0241(16) Uani 1 1 d . . . N1 N 0.6816(7) 0.2225(5) 0.2810(6) 0.0189(17) Uiso 1 1 d . . . N2 N 1.3622(9) 0.0381(7) 0.5599(6) 0.034(2) Uani 1 1 d . . . N3 N 1.0510(10) 0.6690(7) 0.4305(8) 0.042(3) Uani 1 1 d . . . N4 N 0.0728(8) 0.1873(6) -0.1606(7) 0.032(2) Uani 1 1 d . . . C1 C 0.7811(8) 0.2056(6) 0.2424(7) 0.0159(18) Uani 1 1 d . . . H1A H 0.8083 0.2590 0.2231 0.019 Uiso 1 1 calc R . . H1B H 0.7493 0.1719 0.1850 0.019 Uiso 1 1 calc R . . C2 C 0.8916(9) 0.1612(6) 0.3068(7) 0.020(2) Uani 1 1 d . . . H2A H 0.9631 0.1710 0.2851 0.024 Uiso 1 1 calc R . . H2B H 0.9095 0.1822 0.3717 0.024 Uiso 1 1 calc R . . C3 C 0.9556(9) 0.0227(7) 0.3516(7) 0.023(2) Uani 1 1 d . . . C4 C 0.9286(9) -0.0618(7) 0.3394(8) 0.025(2) Uani 1 1 d . . . H4 H 0.8506 -0.0797 0.3032 0.030 Uiso 1 1 calc R . . C5 C 1.0173(10) -0.1188(7) 0.3810(8) 0.027(2) Uani 1 1 d . . . H5 H 1.0005 -0.1762 0.3716 0.032 Uiso 1 1 calc R . . C6 C 1.1302(11) -0.0936(7) 0.4362(7) 0.029(2) Uani 1 1 d . . . H6 H 1.1904 -0.1335 0.4638 0.035 Uiso 1 1 calc R . . C7 C 1.1551(9) -0.0098(7) 0.4511(7) 0.021(2) Uani 1 1 d . . . C8 C 1.0659(9) 0.0495(7) 0.4070(8) 0.024(2) Uani 1 1 d . . . H8 H 1.0824 0.1070 0.4158 0.028 Uiso 1 1 calc R . . C9 C 1.2697(11) 0.0161(7) 0.5111(8) 0.030(3) Uani 1 1 d . . . C10 C 0.7194(9) 0.2764(6) 0.3660(7) 0.019(2) Uani 1 1 d . . . H10A H 0.7738 0.2444 0.4181 0.022 Uiso 1 1 calc R . . H10B H 0.6469 0.2912 0.3843 0.022 Uiso 1 1 calc R . . C11 C 0.7825(9) 0.3546(6) 0.3534(7) 0.018(2) Uani 1 1 d . . . H11A H 0.7973 0.3895 0.4101 0.022 Uiso 1 1 calc R . . H11B H 0.8614 0.3411 0.3444 0.022 Uiso 1 1 calc R . . C12 C 0.7426(10) 0.4809(6) 0.2644(7) 0.021(2) Uani 1 1 d . . . C13 C 0.6671(8) 0.5250(6) 0.1916(8) 0.020(2) Uani 1 1 d . . . H13 H 0.6003 0.4980 0.1489 0.024 Uiso 1 1 calc R . . C14 C 0.6865(9) 0.6077(6) 0.1797(7) 0.019(2) Uiso 1 1 d . . . H14 H 0.6341 0.6374 0.1288 0.023 Uiso 1 1 calc R . . C15 C 0.7844(10) 0.6476(6) 0.2433(8) 0.025(2) Uani 1 1 d . . . H15 H 0.7974 0.7052 0.2379 0.030 Uiso 1 1 calc R . . C16 C 0.8625(9) 0.6008(7) 0.3149(7) 0.023(2) Uani 1 1 d . . . C17 C 0.8436(9) 0.5164(5) 0.3255(7) 0.0175(19) Uani 1 1 d . . . H17 H 0.8984 0.4847 0.3732 0.021 Uiso 1 1 calc R . . C18 C 0.9649(11) 0.6400(7) 0.3788(8) 0.028(2) Uani 1 1 d . . . C19 C 0.6281(9) 0.1464(6) 0.3092(6) 0.018(2) Uani 1 1 d . . . H19A H 0.6919 0.1172 0.3580 0.022 Uiso 1 1 calc R . . H19B H 0.5651 0.1634 0.3377 0.022 Uiso 1 1 calc R . . C20 C 0.5737(8) 0.0874(6) 0.2315(7) 0.021(2) Uani 1 1 d . . . H20A H 0.6350 0.0687 0.2021 0.025 Uiso 1 1 calc R . . H20B H 0.5414 0.0383 0.2555 0.025 Uiso 1 1 calc R . . C21 C 0.4046(8) 0.0878(6) 0.0902(6) 0.0134(17) Uiso 1 1 d . . . C22 C 0.4148(10) 0.0037(6) 0.0737(7) 0.023(2) Uani 1 1 d . . . H22 H 0.4769 -0.0280 0.1154 0.028 Uiso 1 1 calc R . . C23 C 0.3359(10) -0.0333(7) -0.0021(7) 0.023(2) Uani 1 1 d . . . H23 H 0.3423 -0.0911 -0.0111 0.028 Uiso 1 1 calc R . . C24 C 0.2459(10) 0.0118(7) -0.0670(8) 0.027(2) Uani 1 1 d . . . H24 H 0.1933 -0.0142 -0.1208 0.032 Uiso 1 1 calc R . . C25 C 0.2356(9) 0.0965(6) -0.0504(8) 0.022(2) Uani 1 1 d . . . C26 C 0.3144(9) 0.1346(6) 0.0298(7) 0.019(2) Uiso 1 1 d . . . H26 H 0.3055 0.1915 0.0421 0.023 Uiso 1 1 calc R . . C27 C 0.1455(9) 0.1467(6) -0.1114(7) 0.022(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 Hg 0.01923(18) 0.01927(19) 0.01889(18) -0.00045(17) 0.00423(13) -0.00116(16) Cl1 0.0282(13) 0.0387(16) 0.0235(13) 0.0059(11) 0.0054(10) 0.0006(12) Cl2 0.0240(12) 0.0234(12) 0.0299(13) -0.0017(10) 0.0124(11) 0.0011(10) O1 0.022(4) 0.013(3) 0.035(4) 0.000(3) 0.004(3) -0.005(3) O2 0.014(3) 0.011(3) 0.023(4) 0.003(3) 0.002(3) -0.011(3) O3 0.018(4) 0.021(4) 0.030(4) -0.007(3) 0.002(3) -0.004(3) N2 0.027(5) 0.050(6) 0.015(4) 0.018(4) -0.010(4) 0.004(5) N3 0.046(7) 0.028(5) 0.039(6) 0.009(5) -0.008(5) -0.005(5) N4 0.024(5) 0.036(6) 0.036(5) -0.005(5) 0.009(4) 0.001(4) C1 0.010(4) 0.016(5) 0.019(5) 0.003(4) 0.001(3) 0.000(4) C2 0.027(5) 0.015(5) 0.018(5) 0.000(4) 0.008(4) -0.006(4) C3 0.022(5) 0.022(5) 0.021(5) 0.004(4) 0.000(4) 0.009(4) C4 0.019(5) 0.023(5) 0.030(6) -0.005(4) 0.006(4) 0.001(4) C5 0.028(6) 0.020(5) 0.032(6) 0.001(5) 0.007(5) 0.006(4) C6 0.041(7) 0.021(5) 0.019(5) -0.004(4) 0.002(5) 0.004(5) C7 0.017(5) 0.031(6) 0.015(5) 0.014(4) 0.004(4) 0.011(4) C8 0.016(5) 0.018(5) 0.036(6) 0.002(4) 0.007(4) 0.007(4) C9 0.030(6) 0.026(6) 0.032(6) 0.013(5) 0.005(5) 0.007(5) C10 0.023(5) 0.016(5) 0.016(5) -0.008(4) 0.005(4) -0.009(4) C11 0.019(5) 0.019(5) 0.014(5) 0.007(4) 0.003(4) 0.015(4) C12 0.028(5) 0.019(5) 0.019(5) 0.010(4) 0.011(4) 0.004(4) C13 0.009(4) 0.014(5) 0.033(6) 0.004(4) -0.001(4) -0.009(4) C15 0.030(6) 0.015(5) 0.030(6) 0.003(4) 0.009(5) 0.000(4) C16 0.014(5) 0.033(6) 0.020(5) 0.002(4) 0.003(4) 0.003(4) C17 0.020(5) 0.006(4) 0.026(5) -0.009(4) 0.005(4) -0.007(4) C18 0.036(6) 0.017(5) 0.026(6) 0.001(4) 0.002(5) -0.004(5) C19 0.023(5) 0.024(5) 0.010(4) -0.007(4) 0.009(4) -0.006(4) C20 0.012(4) 0.020(5) 0.029(5) 0.011(4) 0.006(4) 0.003(4) C22 0.031(6) 0.020(5) 0.016(5) -0.003(4) 0.005(4) -0.010(4) C23 0.032(6) 0.024(5) 0.017(5) 0.001(4) 0.013(4) -0.002(4) C24 0.026(5) 0.022(5) 0.032(6) -0.001(5) 0.009(5) -0.010(4) C25 0.023(5) 0.019(5) 0.029(6) -0.005(4) 0.014(4) -0.006(4) C27 0.012(4) 0.023(5) 0.024(5) -0.006(4) -0.004(4) -0.002(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 Hg Cl1 2.303(3) . ? Hg Cl2 2.323(3) . ? Hg N1 2.540(8) . ? O1 C3 1.372(12) . ? O1 C2 1.443(11) . ? O2 C12 1.393(11) . ? O2 C11 1.442(11) . ? O3 C21 1.367(11) . ? O3 C20 1.447(11) . ? N1 C1 1.465(12) . ? N1 C19 1.494(12) . ? N1 C10 1.494(12) . ? N2 C9 1.158(15) . ? N3 C18 1.164(15) . ? N4 C27 1.145(14) . ? C1 C2 1.532(13) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.370(14) . ? C3 C4 1.402(15) . ? C4 C5 1.383(15) . ? C4 H4 0.9500 . ? C5 C6 1.384(16) . ? C5 H5 0.9500 . ? C6 C7 1.389(15) . ? C6 H6 0.9500 . ? C7 C8 1.420(13) . ? C7 C9 1.426(16) . ? C8 H8 0.9500 . ? C10 C11 1.501(13) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.375(14) . ? C12 C17 1.376(14) . ? C13 C14 1.376(13) . ? C13 H13 0.9500 . ? C14 C15 1.401(14) . ? C14 H14 0.9500 . ? C15 C16 1.400(14) . ? C15 H15 0.9500 . ? C16 C17 1.400(14) . ? C16 C18 1.430(15) . ? C17 H17 0.9500 . ? C19 C20 1.491(14) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C26 1.385(13) . ? C21 C22 1.393(14) . ? C22 C23 1.363(14) . ? C22 H22 0.9500 . ? C23 C24 1.399(15) . ? C23 H23 0.9500 . ? C24 C25 1.403(15) . ? C24 H24 0.9500 . ? C25 C26 1.413(14) . ? C25 C27 1.418(15) . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl1 Hg Cl2 162.22(10) . . ? Cl1 Hg N1 99.1(2) . . ? Cl2 Hg N1 98.4(2) . . ? C3 O1 C2 116.2(8) . . ? C12 O2 C11 116.0(7) . . ? C21 O3 C20 118.2(8) . . ? C1 N1 C19 113.8(8) . . ? C1 N1 C10 112.3(8) . . ? C19 N1 C10 106.3(7) . . ? C1 N1 Hg 112.2(6) . . ? C19 N1 Hg 107.9(6) . . ? C10 N1 Hg 103.7(6) . . ? N1 C1 C2 116.8(8) . . ? N1 C1 H1A 108.1 . . ? C2 C1 H1A 108.1 . . ? N1 C1 H1B 108.1 . . ? C2 C1 H1B 108.1 . . ? H1A C1 H1B 107.3 . . ? O1 C2 C1 107.4(8) . . ? O1 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? C8 C3 O1 124.4(10) . . ? C8 C3 C4 121.2(9) . . ? O1 C3 C4 114.4(9) . . ? C5 C4 C3 118.9(10) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.1(11) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C5 C6 C7 119.8(10) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C6 C7 C8 119.7(10) . . ? C6 C7 C9 119.8(10) . . ? C8 C7 C9 120.5(10) . . ? C3 C8 C7 119.2(10) . . ? C3 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? N2 C9 C7 179.1(13) . . ? N1 C10 C11 114.5(8) . . ? N1 C10 H10A 108.6 . . ? C11 C10 H10A 108.6 . . ? N1 C10 H10B 108.6 . . ? C11 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? O2 C11 C10 109.7(8) . . ? O2 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? O2 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C13 C12 C17 121.6(9) . . ? C13 C12 O2 115.7(9) . . ? C17 C12 O2 122.6(9) . . ? C12 C13 C14 121.0(9) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 119.4(10) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 118.6(10) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C17 121.8(10) . . ? C15 C16 C18 119.4(10) . . ? C17 C16 C18 118.9(9) . . ? C12 C17 C16 117.5(10) . . ? C12 C17 H17 121.3 . . ? C16 C17 H17 121.3 . . ? N3 C18 C16 177.2(13) . . ? C20 C19 N1 114.9(8) . . ? C20 C19 H19A 108.5 . . ? N1 C19 H19A 108.5 . . ? C20 C19 H19B 108.5 . . ? N1 C19 H19B 108.5 . . ? H19A C19 H19B 107.5 . . ? O3 C20 C19 106.7(8) . . ? O3 C20 H20A 110.4 . . ? C19 C20 H20A 110.4 . . ? O3 C20 H20B 110.4 . . ? C19 C20 H20B 110.4 . . ? H20A C20 H20B 108.6 . . ? O3 C21 C26 114.2(8) . . ? O3 C21 C22 125.4(9) . . ? C26 C21 C22 120.4(9) . . ? C23 C22 C21 120.2(10) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 121.6(10) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C23 C24 C25 118.1(10) . . ? C23 C24 H24 120.9 . . ? C25 C24 H24 120.9 . . ? C24 C25 C26 120.5(10) . . ? C24 C25 C27 122.0(10) . . ? C26 C25 C27 117.5(9) . . ? C21 C26 C25 119.1(9) . . ? C21 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? N4 C27 C25 179.9(15) . . ? 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 Cl1 Hg N1 C1 12.6(6) . . . . ? Cl2 Hg N1 C1 -170.2(6) . . . . ? Cl1 Hg N1 C19 -113.5(5) . . . . ? Cl2 Hg N1 C19 63.7(6) . . . . ? Cl1 Hg N1 C10 134.0(5) . . . . ? Cl2 Hg N1 C10 -48.8(6) . . . . ? C19 N1 C1 C2 -60.4(11) . . . . ? C10 N1 C1 C2 60.3(11) . . . . ? Hg N1 C1 C2 176.7(6) . . . . ? C3 O1 C2 C1 175.3(8) . . . . ? N1 C1 C2 O1 80.9(10) . . . . ? C2 O1 C3 C8 5.3(15) . . . . ? C2 O1 C3 C4 -174.2(9) . . . . ? C8 C3 C4 C5 -2.9(17) . . . . ? O1 C3 C4 C5 176.6(10) . . . . ? C3 C4 C5 C6 1.9(17) . . . . ? C4 C5 C6 C7 0.6(17) . . . . ? C5 C6 C7 C8 -2.1(16) . . . . ? C5 C6 C7 C9 177.4(11) . . . . ? O1 C3 C8 C7 -178.1(10) . . . . ? C4 C3 C8 C7 1.4(17) . . . . ? C6 C7 C8 C3 1.1(16) . . . . ? C9 C7 C8 C3 -178.3(10) . . . . ? C6 C7 C9 N2 -167(100) . . . . ? C8 C7 C9 N2 12(86) . . . . ? C1 N1 C10 C11 51.6(11) . . . . ? C19 N1 C10 C11 176.6(8) . . . . ? Hg N1 C10 C11 -69.7(8) . . . . ? C12 O2 C11 C10 166.3(8) . . . . ? N1 C10 C11 O2 53.7(11) . . . . ? C11 O2 C12 C13 -175.3(9) . . . . ? C11 O2 C12 C17 3.6(13) . . . . ? C17 C12 C13 C14 -3.1(16) . . . . ? O2 C12 C13 C14 175.8(9) . . . . ? C12 C13 C14 C15 -0.6(16) . . . . ? C13 C14 C15 C16 2.8(15) . . . . ? C14 C15 C16 C17 -1.6(16) . . . . ? C14 C15 C16 C18 178.2(10) . . . . ? C13 C12 C17 C16 4.2(15) . . . . ? O2 C12 C17 C16 -174.6(9) . . . . ? C15 C16 C17 C12 -1.9(15) . . . . ? C18 C16 C17 C12 178.4(10) . . . . ? C15 C16 C18 N3 -137(26) . . . . ? C17 C16 C18 N3 43(27) . . . . ? C1 N1 C19 C20 -61.5(11) . . . . ? C10 N1 C19 C20 174.5(8) . . . . ? Hg N1 C19 C20 63.8(9) . . . . ? C21 O3 C20 C19 -173.3(8) . . . . ? N1 C19 C20 O3 -60.9(10) . . . . ? C20 O3 C21 C26 179.4(8) . . . . ? C20 O3 C21 C22 0.0(14) . . . . ? O3 C21 C22 C23 179.4(9) . . . . ? C26 C21 C22 C23 0.0(15) . . . . ? C21 C22 C23 C24 2.3(16) . . . . ? C22 C23 C24 C25 -2.3(16) . . . . ? C23 C24 C25 C26 0.0(15) . . . . ? C23 C24 C25 C27 -178.7(10) . . . . ? O3 C21 C26 C25 178.4(8) . . . . ? C22 C21 C26 C25 -2.2(14) . . . . ? C24 C25 C26 C21 2.2(15) . . . . ? C27 C25 C26 C21 -179.1(9) . . . . ? C24 C25 C27 N4 -156(100) . . . . ? C26 C25 C27 N4 25(100) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.905 _refine_diff_density_min -0.983 _refine_diff_density_rms 0.399 # Attachment 'Data3.cif' Data_Compound3.CIF _database_code_depnum_ccdc_archive 'CCDC 657111' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 Cl2 Hg N4 O3' _chemical_formula_sum 'C27 H24 Cl2 Hg N4 O3' _chemical_formula_weight 723.99 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' Hg Hg -2.3894 9.2266 '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' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.338(5) _cell_length_b 8.372(5) _cell_length_c 20.101(5) _cell_angle_alpha 92.608(5) _cell_angle_beta 92.608(5) _cell_angle_gamma 106.888(5) _cell_volume 1338.7(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min -28.0 _cell_measurement_theta_max +28.0 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 5.984 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4672 _exptl_absorpt_correction_T_max 0.6149 _exptl_absorpt_process_details 'BRUKER SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD _diffrn_measurement_method phi-omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8871 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0477 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 28.35 _reflns_number_total 6254 _reflns_number_gt 5703 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0391P)^2^+12.7707P] 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 6254 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 Cl1 Cl 0.5267(2) -0.0241(2) 0.12843(8) 0.0260(3) Uani 1 1 d . . . Cl2 Cl 0.4916(2) 0.5017(2) 0.16256(8) 0.0267(3) Uani 1 1 d . . . Hg Hg 0.46278(3) 0.21832(3) 0.163227(12) 0.01925(9) Uani 1 1 d . . . O1 O 0.1426(5) 0.1392(6) 0.1016(2) 0.0197(9) Uani 1 1 d . . . O2 O 0.5767(5) 0.2095(5) 0.2979(2) 0.0160(8) Uani 1 1 d . . . O3 O -0.0962(5) 0.0692(6) 0.2962(2) 0.0164(9) Uani 1 1 d . . . N1 N 0.2391(6) 0.0958(6) 0.2396(2) 0.0130(9) Uani 1 1 d . . . N2 N -0.0640(8) 0.4951(8) -0.1694(3) 0.0288(13) Uani 1 1 d . . . N3 N 1.1972(7) 0.8482(8) 0.4440(3) 0.0244(12) Uani 1 1 d . . . N4 N -0.6609(8) -0.5467(8) 0.4345(3) 0.0262(13) Uani 1 1 d . . . C1 C 0.1077(8) -0.0286(8) 0.1957(3) 0.0174(12) Uani 1 1 d . . . H1A H 0.0233 -0.0971 0.2240 0.021 Uiso 1 1 calc R . . H1B H 0.1608 -0.1045 0.1720 0.021 Uiso 1 1 calc R . . C2 C 0.0189(8) 0.0486(8) 0.1447(3) 0.0172(12) Uani 1 1 d . . . H2A H -0.0692 -0.0398 0.1184 0.021 Uiso 1 1 calc R . . H2B H -0.0348 0.1254 0.1673 0.021 Uiso 1 1 calc R . . C3 C 0.0879(8) 0.2051(8) 0.0475(3) 0.0178(12) Uani 1 1 d . . . C4 C -0.0808(8) 0.1882(8) 0.0300(3) 0.0175(12) Uani 1 1 d . . . H4 H -0.1670 0.1276 0.0563 0.021 Uiso 1 1 calc R . . C5 C -0.1201(9) 0.2616(8) -0.0266(3) 0.0207(13) Uani 1 1 d . . . H5 H -0.2343 0.2490 -0.0395 0.025 Uiso 1 1 calc R . . C6 C 0.0056(9) 0.3530(8) -0.0645(3) 0.0202(13) Uani 1 1 d . . . C7 C 0.1733(9) 0.3694(9) -0.0467(3) 0.0223(13) Uani 1 1 d . . . H7 H 0.2593 0.4316 -0.0728 0.027 Uiso 1 1 calc R . . C8 C 0.2140(8) 0.2953(9) 0.0086(3) 0.0230(14) Uani 1 1 d . . . H8 H 0.3283 0.3054 0.0205 0.028 Uiso 1 1 calc R . . C9 C -0.0357(9) 0.4320(8) -0.1222(3) 0.0227(14) Uani 1 1 d . . . C10 C 0.3143(7) -0.0004(7) 0.2850(3) 0.0131(11) Uani 1 1 d . . . H10A H 0.3653 -0.0724 0.2579 0.016 Uiso 1 1 calc R . . H10B H 0.2239 -0.0745 0.3092 0.016 Uiso 1 1 calc R . . C11 C 0.4464(7) 0.1067(8) 0.3352(3) 0.0152(11) Uani 1 1 d . . . H11A H 0.3975 0.1775 0.3639 0.018 Uiso 1 1 calc R . . H11B H 0.4924 0.0355 0.3640 0.018 Uiso 1 1 calc R . . C12 C 0.7030(7) 0.3302(7) 0.3319(3) 0.0138(11) Uani 1 1 d . . . C13 C 0.7195(7) 0.3555(8) 0.4015(3) 0.0153(11) Uani 1 1 d . . . H13 H 0.6430 0.2832 0.4284 0.018 Uiso 1 1 calc R . . C14 C 0.8494(7) 0.4880(8) 0.4307(3) 0.0151(11) Uani 1 1 d . . . H14 H 0.8599 0.5091 0.4778 0.018 Uiso 1 1 calc R . . C15 C 0.9648(8) 0.5904(7) 0.3906(3) 0.0148(11) Uani 1 1 d . . . C16 C 0.9515(8) 0.5596(8) 0.3218(3) 0.0181(12) Uani 1 1 d . . . H16 H 1.0317 0.6277 0.2949 0.022 Uiso 1 1 calc R . . C17 C 0.8216(8) 0.4302(8) 0.2926(3) 0.0154(11) Uani 1 1 d . . . H17 H 0.8126 0.4088 0.2456 0.019 Uiso 1 1 calc R . . C18 C 1.0948(8) 0.7332(8) 0.4213(3) 0.0188(12) Uani 1 1 d . . . C19 C 0.1808(7) 0.2272(7) 0.2756(3) 0.0127(11) Uani 1 1 d . . . H19A H 0.1265 0.2817 0.2424 0.015 Uiso 1 1 calc R . . H19B H 0.2806 0.3135 0.2964 0.015 Uiso 1 1 calc R . . C20 C 0.0595(7) 0.1665(8) 0.3291(3) 0.0161(12) Uani 1 1 d . . . H20A H 0.1036 0.0975 0.3596 0.019 Uiso 1 1 calc R . . H20B H 0.0434 0.2628 0.3555 0.019 Uiso 1 1 calc R . . C21 C -0.2069(8) -0.0459(7) 0.3302(3) 0.0136(11) Uani 1 1 d . . . C22 C -0.3289(8) -0.1684(8) 0.2905(3) 0.0186(12) Uani 1 1 d . . . H22 H -0.3314 -0.1660 0.2433 0.022 Uiso 1 1 calc R . . C23 C -0.4441(8) -0.2913(8) 0.3200(3) 0.0200(13) Uani 1 1 d . . . H23 H -0.5260 -0.3748 0.2932 0.024 Uiso 1 1 calc R . . C24 C -0.4422(8) -0.2948(8) 0.3897(3) 0.0168(12) Uani 1 1 d . . . C25 C -0.3240(8) -0.1737(8) 0.4294(3) 0.0181(12) Uani 1 1 d . . . H25 H -0.3230 -0.1769 0.4766 0.022 Uiso 1 1 calc R . . C26 C -0.2054(8) -0.0459(8) 0.4000(3) 0.0166(12) Uani 1 1 d . . . H26 H -0.1253 0.0393 0.4269 0.020 Uiso 1 1 calc R . . C27 C -0.5632(8) -0.4308(8) 0.4172(3) 0.0194(13) 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 Cl1 0.0228(8) 0.0334(9) 0.0217(8) 0.0011(7) 0.0000(6) 0.0081(7) Cl2 0.0298(8) 0.0254(8) 0.0206(8) 0.0002(6) 0.0026(6) 0.0012(7) Hg 0.01674(13) 0.02484(14) 0.01280(12) 0.00262(8) -0.00130(8) 0.00088(9) O1 0.016(2) 0.028(2) 0.013(2) 0.0061(18) -0.0020(16) 0.0031(18) O2 0.016(2) 0.020(2) 0.010(2) 0.0049(16) -0.0015(16) 0.0015(17) O3 0.0105(19) 0.024(2) 0.012(2) -0.0006(17) -0.0058(15) 0.0025(17) N1 0.014(2) 0.018(2) 0.005(2) 0.0014(18) -0.0040(17) 0.0028(19) N2 0.037(4) 0.040(4) 0.016(3) 0.011(3) 0.004(2) 0.020(3) N3 0.024(3) 0.029(3) 0.017(3) 0.000(2) -0.004(2) 0.004(2) N4 0.025(3) 0.032(3) 0.018(3) -0.004(2) 0.003(2) 0.003(3) C1 0.018(3) 0.023(3) 0.009(3) 0.000(2) -0.002(2) 0.003(2) C2 0.015(3) 0.023(3) 0.011(3) 0.005(2) -0.005(2) 0.001(2) C3 0.024(3) 0.020(3) 0.008(3) 0.000(2) -0.006(2) 0.006(3) C4 0.020(3) 0.021(3) 0.009(3) 0.002(2) 0.001(2) 0.000(2) C5 0.024(3) 0.028(3) 0.011(3) 0.002(2) -0.003(2) 0.010(3) C6 0.030(3) 0.019(3) 0.010(3) -0.002(2) -0.002(2) 0.004(3) C7 0.024(3) 0.028(3) 0.012(3) 0.005(2) 0.004(2) 0.003(3) C8 0.019(3) 0.031(4) 0.015(3) 0.002(3) 0.000(2) 0.002(3) C9 0.029(4) 0.024(3) 0.012(3) -0.004(2) 0.004(3) 0.005(3) C10 0.012(3) 0.012(3) 0.014(3) 0.004(2) -0.005(2) 0.001(2) C11 0.012(3) 0.019(3) 0.013(3) 0.003(2) -0.002(2) 0.002(2) C12 0.012(3) 0.014(3) 0.015(3) 0.005(2) -0.003(2) 0.004(2) C13 0.011(3) 0.018(3) 0.014(3) 0.004(2) 0.000(2) 0.000(2) C14 0.014(3) 0.019(3) 0.010(3) 0.003(2) 0.001(2) 0.003(2) C15 0.019(3) 0.014(3) 0.012(3) 0.001(2) 0.000(2) 0.006(2) C16 0.022(3) 0.020(3) 0.011(3) 0.004(2) -0.001(2) 0.004(2) C17 0.020(3) 0.020(3) 0.006(3) 0.001(2) -0.005(2) 0.006(2) C18 0.023(3) 0.021(3) 0.010(3) -0.001(2) -0.003(2) 0.003(3) C19 0.011(3) 0.013(3) 0.013(3) -0.001(2) 0.000(2) 0.003(2) C20 0.012(3) 0.021(3) 0.015(3) 0.000(2) -0.002(2) 0.004(2) C21 0.019(3) 0.013(3) 0.008(3) -0.003(2) -0.004(2) 0.004(2) C22 0.018(3) 0.024(3) 0.013(3) -0.001(2) 0.001(2) 0.007(3) C23 0.021(3) 0.021(3) 0.016(3) -0.008(2) -0.003(2) 0.005(3) C24 0.020(3) 0.015(3) 0.018(3) 0.007(2) 0.003(2) 0.009(2) C25 0.022(3) 0.022(3) 0.012(3) 0.004(2) -0.002(2) 0.008(3) C26 0.015(3) 0.022(3) 0.012(3) 0.001(2) 0.000(2) 0.006(2) C27 0.015(3) 0.028(3) 0.018(3) 0.002(3) 0.002(2) 0.011(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 Cl1 Hg 2.329(2) . ? Cl2 Hg 2.315(2) . ? Hg N1 2.486(5) . ? O1 C3 1.359(7) . ? O1 C2 1.442(7) . ? O2 C12 1.361(7) . ? O2 C11 1.441(7) . ? O3 C21 1.358(7) . ? O3 C20 1.430(7) . ? N1 C10 1.476(7) . ? N1 C1 1.494(8) . ? N1 C19 1.496(7) . ? N2 C9 1.155(9) . ? N3 C18 1.145(9) . ? N4 C27 1.151(9) . ? C1 C2 1.512(8) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.398(9) . ? C3 C4 1.400(9) . ? C4 C5 1.387(9) . ? C4 H4 0.9500 . ? C5 C6 1.388(9) . ? C5 H5 0.9500 . ? C6 C7 1.392(10) . ? C6 C9 1.438(9) . ? C7 C8 1.375(9) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C10 C11 1.510(8) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C17 1.398(8) . ? C12 C13 1.400(8) . ? C13 C14 1.390(8) . ? C13 H13 0.9500 . ? C14 C15 1.403(8) . ? C14 H14 0.9500 . ? C15 C16 1.389(8) . ? C15 C18 1.450(9) . ? C16 C17 1.375(9) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C19 C20 1.513(8) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C26 1.403(8) . ? C21 C22 1.402(8) . ? C22 C23 1.366(9) . ? C22 H22 0.9500 . ? C23 C24 1.402(9) . ? C23 H23 0.9500 . ? C24 C25 1.382(9) . ? C24 C27 1.435(9) . ? C25 C26 1.403(9) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Hg Cl1 153.40(6) . . ? Cl2 Hg N1 107.48(12) . . ? Cl1 Hg N1 99.09(13) . . ? C3 O1 C2 117.9(5) . . ? C12 O2 C11 118.2(5) . . ? C21 O3 C20 119.6(5) . . ? C10 N1 C1 106.8(5) . . ? C10 N1 C19 113.1(4) . . ? C1 N1 C19 115.3(5) . . ? C10 N1 Hg 104.8(3) . . ? C1 N1 Hg 104.0(3) . . ? C19 N1 Hg 112.0(3) . . ? N1 C1 C2 114.1(5) . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1B 108.7 . . ? C2 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? O1 C2 C1 107.8(5) . . ? O1 C2 H2A 110.2 . . ? C1 C2 H2A 110.2 . . ? O1 C2 H2B 110.2 . . ? C1 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? O1 C3 C8 115.2(6) . . ? O1 C3 C4 124.6(6) . . ? C8 C3 C4 120.2(6) . . ? C5 C4 C3 118.9(6) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 120.7(6) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C7 120.1(6) . . ? C5 C6 C9 120.4(6) . . ? C7 C6 C9 119.4(6) . . ? C8 C7 C6 119.8(6) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C3 120.3(6) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? N2 C9 C6 177.8(7) . . ? N1 C10 C11 114.1(5) . . ? N1 C10 H10A 108.7 . . ? C11 C10 H10A 108.7 . . ? N1 C10 H10B 108.7 . . ? C11 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? O2 C11 C10 106.8(5) . . ? O2 C11 H11A 110.4 . . ? C10 C11 H11A 110.4 . . ? O2 C11 H11B 110.4 . . ? C10 C11 H11B 110.4 . . ? H11A C11 H11B 108.6 . . ? O2 C12 C17 115.5(5) . . ? O2 C12 C13 124.2(5) . . ? C17 C12 C13 120.4(5) . . ? C14 C13 C12 119.1(5) . . ? C14 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C13 C14 C15 119.9(6) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.5(6) . . ? C16 C15 C18 120.1(6) . . ? C14 C15 C18 119.4(5) . . ? C17 C16 C15 119.8(6) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C12 120.3(5) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.9 . . ? N3 C18 C15 178.1(7) . . ? N1 C19 C20 115.7(5) . . ? N1 C19 H19A 108.3 . . ? C20 C19 H19A 108.3 . . ? N1 C19 H19B 108.3 . . ? C20 C19 H19B 108.3 . . ? H19A C19 H19B 107.4 . . ? O3 C20 C19 107.3(5) . . ? O3 C20 H20A 110.3 . . ? C19 C20 H20A 110.3 . . ? O3 C20 H20B 110.3 . . ? C19 C20 H20B 110.3 . . ? H20A C20 H20B 108.5 . . ? O3 C21 C26 124.1(5) . . ? O3 C21 C22 115.5(5) . . ? C26 C21 C22 120.4(6) . . ? C23 C22 C21 119.8(6) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.4(6) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C25 C24 C23 120.3(6) . . ? C25 C24 C27 122.3(6) . . ? C23 C24 C27 117.4(6) . . ? C24 C25 C26 120.0(6) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C21 C26 C25 118.9(6) . . ? C21 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? N4 C27 C24 174.6(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 Cl2 Hg N1 C10 -129.3(3) . . . . ? Cl1 Hg N1 C10 52.0(3) . . . . ? Cl2 Hg N1 C1 118.8(3) . . . . ? Cl1 Hg N1 C1 -60.0(3) . . . . ? Cl2 Hg N1 C19 -6.3(4) . . . . ? Cl1 Hg N1 C19 174.9(3) . . . . ? C10 N1 C1 C2 -178.9(5) . . . . ? C19 N1 C1 C2 54.6(7) . . . . ? Hg N1 C1 C2 -68.4(5) . . . . ? C3 O1 C2 C1 173.5(5) . . . . ? N1 C1 C2 O1 61.9(7) . . . . ? C2 O1 C3 C8 178.3(6) . . . . ? C2 O1 C3 C4 -1.4(9) . . . . ? O1 C3 C4 C5 -179.9(6) . . . . ? C8 C3 C4 C5 0.3(9) . . . . ? C3 C4 C5 C6 -1.3(10) . . . . ? C4 C5 C6 C7 1.3(10) . . . . ? C4 C5 C6 C9 -178.5(6) . . . . ? C5 C6 C7 C8 -0.3(10) . . . . ? C9 C6 C7 C8 179.5(6) . . . . ? C6 C7 C8 C3 -0.7(10) . . . . ? O1 C3 C8 C7 -179.1(6) . . . . ? C4 C3 C8 C7 0.7(10) . . . . ? C5 C6 C9 N2 -153(19) . . . . ? C7 C6 C9 N2 27(20) . . . . ? C1 N1 C10 C11 -177.7(5) . . . . ? C19 N1 C10 C11 -49.9(6) . . . . ? Hg N1 C10 C11 72.3(5) . . . . ? C12 O2 C11 C10 173.3(5) . . . . ? N1 C10 C11 O2 -59.7(6) . . . . ? C11 O2 C12 C17 -177.4(5) . . . . ? C11 O2 C12 C13 3.5(8) . . . . ? O2 C12 C13 C14 -177.0(5) . . . . ? C17 C12 C13 C14 4.0(9) . . . . ? C12 C13 C14 C15 -2.2(9) . . . . ? C13 C14 C15 C16 -0.6(9) . . . . ? C13 C14 C15 C18 177.0(6) . . . . ? C14 C15 C16 C17 1.6(9) . . . . ? C18 C15 C16 C17 -176.0(6) . . . . ? C15 C16 C17 C12 0.2(9) . . . . ? O2 C12 C17 C16 177.8(5) . . . . ? C13 C12 C17 C16 -3.0(9) . . . . ? C16 C15 C18 N3 32(23) . . . . ? C14 C15 C18 N3 -146(23) . . . . ? C10 N1 C19 C20 -55.0(6) . . . . ? C1 N1 C19 C20 68.2(6) . . . . ? Hg N1 C19 C20 -173.1(4) . . . . ? C21 O3 C20 C19 157.4(5) . . . . ? N1 C19 C20 O3 -69.9(6) . . . . ? C20 O3 C21 C26 19.5(8) . . . . ? C20 O3 C21 C22 -161.3(5) . . . . ? O3 C21 C22 C23 178.9(6) . . . . ? C26 C21 C22 C23 -1.9(9) . . . . ? C21 C22 C23 C24 0.6(10) . . . . ? C22 C23 C24 C25 0.2(10) . . . . ? C22 C23 C24 C27 -177.9(6) . . . . ? C23 C24 C25 C26 0.3(9) . . . . ? C27 C24 C25 C26 178.2(6) . . . . ? O3 C21 C26 C25 -178.6(6) . . . . ? C22 C21 C26 C25 2.3(9) . . . . ? C24 C25 C26 C21 -1.5(9) . . . . ? C25 C24 C27 N4 -155(7) . . . . ? C23 C24 C27 N4 23(8) . . . . ? _diffrn_measured_fraction_theta_max 0.99 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.99 _refine_diff_density_max 3.125 _refine_diff_density_min -2.184 _refine_diff_density_rms 0.222 # Attachment 'Compound 4, old CCDC no 657112.doc' data_Compound4 _database_code_depnum_ccdc_archive 'CCDC 657112' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 Cl2 Hg N4 O9' _chemical_formula_sum 'C24 H24 Cl2 Hg N4 O9' _chemical_formula_weight 783.96 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' Hg Hg -2.3894 9.2266 '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 _symmetry_space_group_name_Hall -P1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.190(5) _cell_length_b 8.396(5) _cell_length_c 20.920(5) _cell_angle_alpha 80.781(1) _cell_angle_beta 88.390(1) _cell_angle_gamma 73.641(1) _cell_volume 1362.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min -28.0 _cell_measurement_theta_max +28.0 _exptl_crystal_description block _exptl_crystal_colour colourless _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 1.911 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 5.905 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4920 _exptl_absorpt_correction_T_max 0.6186 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 CCD _diffrn_measurement_method phi-omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9141 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 28.35 _reflns_number_total 6441 _reflns_number_gt 5856 _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^)+(0.0000P)^2^+46.2900P] 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 6441 _refine_ls_number_parameters 354 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1638 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.243 _refine_ls_restrained_S_all 1.243 _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 Hg1 Hg 0.43814(5) 0.23124(5) 0.156085(18) 0.01634(12) Uani 1 1 d . . . Cl1 Cl 0.5083(3) 0.4792(3) 0.12068(13) 0.0241(5) Uani 1 1 d . . . Cl2 Cl 0.4497(3) -0.0483(3) 0.16224(13) 0.0234(5) Uani 1 1 d . . . O1 O 0.5100(8) 0.1970(9) 0.2904(3) 0.0150(13) Uani 1 1 d . . . O2 O 1.0259(12) -0.3179(12) 0.4916(4) 0.035(2) Uani 1 1 d . . . O3 O 1.1245(10) -0.4046(10) 0.4028(4) 0.0269(17) Uani 1 1 d . . . O4 O 0.1249(8) 0.3250(10) 0.0906(3) 0.0203(15) Uani 1 1 d . . . O5 O 0.1466(11) -0.0533(10) -0.1415(4) 0.0265(17) Uani 1 1 d . . . O6 O -0.0957(11) 0.1344(10) -0.1643(4) 0.0282(17) Uani 1 1 d . . . O7 O -0.1634(8) 0.3619(9) 0.2798(3) 0.0176(14) Uani 1 1 d . . . O8 O -0.7271(10) 0.9210(10) 0.3865(4) 0.0256(17) Uani 1 1 d . . . O9 O -0.6032(11) 0.7833(10) 0.4764(4) 0.0283(18) Uani 1 1 d . . . N1 N 0.1894(10) 0.3390(10) 0.2238(4) 0.0136(15) Uani 1 1 d . . . N2 N 1.0209(11) -0.3069(11) 0.4331(4) 0.0210(18) Uani 1 1 d . . . N3 N 0.0296(11) 0.0685(10) -0.1292(4) 0.0167(16) Uani 1 1 d . . . N4 N -0.6172(10) 0.8045(10) 0.4181(4) 0.0160(16) Uani 1 1 d . . . C1 C 0.2551(12) 0.4220(11) 0.2701(5) 0.0175(19) Uani 1 1 d . . . H1A H 0.1577 0.4916 0.2916 0.021 Uiso 1 1 calc R . . H1B H 0.3164 0.4983 0.2460 0.021 Uiso 1 1 calc R . . C2 C 0.3733(12) 0.3012(12) 0.3214(5) 0.0153(18) Uani 1 1 d . . . H2A H 0.4181 0.3643 0.3494 0.018 Uiso 1 1 calc R . . H2B H 0.3109 0.2312 0.3488 0.018 Uiso 1 1 calc R . . C3 C 0.6302(11) 0.0769(11) 0.3278(5) 0.0136(17) Uani 1 1 d . . . C4 C 0.6378(12) 0.0600(12) 0.3958(5) 0.0152(18) Uani 1 1 d . . . H4 H 0.5542 0.1327 0.4184 0.018 Uiso 1 1 calc R . . C5 C 0.7690(13) -0.0642(12) 0.4291(5) 0.0173(19) Uani 1 1 d . . . H5 H 0.7800 -0.0740 0.4747 0.021 Uiso 1 1 calc R . . C6 C 0.8846(12) -0.1743(13) 0.3957(5) 0.0166(19) Uani 1 1 d . . . C7 C 0.8791(13) -0.1574(12) 0.3294(5) 0.018(2) Uani 1 1 d . . . H7 H 0.9632 -0.2305 0.3072 0.022 Uiso 1 1 calc R . . C8 C 0.7500(13) -0.0330(12) 0.2955(5) 0.0183(19) Uani 1 1 d . . . H8 H 0.7429 -0.0224 0.2497 0.022 Uiso 1 1 calc R . . C9 C 0.0670(13) 0.4745(13) 0.1794(7) 0.0309(17) Uani 1 1 d . . . H9A H 0.1275 0.5548 0.1581 0.037 Uiso 1 1 calc R . . H9B H -0.0242 0.5363 0.2057 0.037 Uiso 1 1 calc R . . C10 C -0.0152(14) 0.4130(15) 0.1271(7) 0.0351(8) Uani 1 1 d . . . H10A H -0.0817 0.3365 0.1469 0.042 Uiso 1 1 calc R . . H10B H -0.0919 0.5091 0.0987 0.042 Uiso 1 1 calc R . . C11 C 0.0886(12) 0.2676(12) 0.0374(4) 0.0147(18) Uani 1 1 d . . . C12 C -0.0745(13) 0.2943(11) 0.0119(5) 0.019(2) Uani 1 1 d . . . H12 H -0.1715 0.3576 0.0318 0.022 Uiso 1 1 calc R . . C13 C -0.0924(13) 0.2276(13) -0.0425(5) 0.020(2) Uani 1 1 d . . . H13 H -0.2027 0.2436 -0.0600 0.023 Uiso 1 1 calc R . . C14 C 0.0499(13) 0.1371(12) -0.0719(5) 0.0177(19) Uani 1 1 d . . . C15 C 0.2143(14) 0.1124(14) -0.0483(5) 0.022(2) Uani 1 1 d . . . H15 H 0.3111 0.0523 -0.0693 0.026 Uiso 1 1 calc R . . C16 C 0.2315(13) 0.1792(13) 0.0074(5) 0.019(2) Uani 1 1 d . . . H16 H 0.3417 0.1641 0.0249 0.023 Uiso 1 1 calc R . . C17 C 0.1165(11) 0.2020(11) 0.2577(5) 0.0145(18) Uani 1 1 d . . . H17A H 0.0624 0.1603 0.2246 0.017 Uiso 1 1 calc R . . H17B H 0.2117 0.1073 0.2778 0.017 Uiso 1 1 calc R . . C18 C -0.0111(12) 0.2507(12) 0.3086(5) 0.0162(18) Uani 1 1 d . . . H18A H -0.0349 0.1489 0.3331 0.019 Uiso 1 1 calc R . . H18B H 0.0354 0.3059 0.3393 0.019 Uiso 1 1 calc R . . C19 C -0.2715(13) 0.4643(14) 0.3167(8) 0.0358(7) Uani 1 1 d . . . C20 C -0.3993(13) 0.5924(13) 0.2821(5) 0.0171(19) Uani 1 1 d . . . H20 H -0.4082 0.6035 0.2363 0.020 Uiso 1 1 calc R . . C21 C -0.5158(13) 0.7057(12) 0.3164(5) 0.0165(19) Uani 1 1 d . . . H21 H -0.6031 0.7956 0.2940 0.020 Uiso 1 1 calc R . . C22 C -0.5008(13) 0.6839(13) 0.3818(5) 0.0163(19) Uani 1 1 d . . . C23 C -0.3750(12) 0.5539(12) 0.4173(5) 0.0157(18) Uani 1 1 d . . . H23 H -0.3673 0.5427 0.4631 0.019 Uiso 1 1 calc R . . C24 C -0.2615(13) 0.4414(13) 0.3837(5) 0.020(2) Uani 1 1 d . . . H24 H -0.1775 0.3491 0.4065 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Hg1 0.01413(18) 0.01838(19) 0.01506(19) -0.00529(13) 0.00140(12) -0.00086(13) Cl1 0.0204(12) 0.0263(13) 0.0242(13) -0.0028(10) 0.0024(10) -0.0051(10) Cl2 0.0278(13) 0.0181(11) 0.0227(12) -0.0046(9) 0.0033(10) -0.0032(10) O1 0.011(3) 0.024(3) 0.010(3) -0.007(3) 0.004(2) -0.002(3) O2 0.036(5) 0.042(5) 0.017(4) -0.009(4) -0.004(3) 0.008(4) O3 0.021(4) 0.028(4) 0.026(4) -0.008(3) -0.005(3) 0.003(3) O4 0.007(3) 0.038(4) 0.015(3) -0.013(3) 0.001(3) -0.001(3) O5 0.043(5) 0.024(4) 0.015(4) -0.009(3) 0.013(3) -0.011(4) O6 0.033(4) 0.029(4) 0.025(4) -0.009(3) -0.002(3) -0.010(4) O7 0.010(3) 0.024(4) 0.018(3) -0.006(3) -0.004(3) -0.002(3) O8 0.025(4) 0.021(4) 0.029(4) -0.005(3) 0.009(3) -0.004(3) O9 0.038(5) 0.033(4) 0.010(3) -0.010(3) 0.001(3) 0.001(4) N1 0.014(4) 0.009(3) 0.016(4) -0.001(3) -0.001(3) -0.002(3) N2 0.019(4) 0.019(4) 0.023(5) -0.004(4) 0.001(3) -0.002(3) N3 0.024(4) 0.013(4) 0.013(4) -0.004(3) 0.006(3) -0.003(3) N4 0.016(4) 0.009(3) 0.021(4) -0.003(3) -0.004(3) 0.001(3) C1 0.013(4) 0.009(4) 0.028(5) 0.004(4) 0.004(4) -0.002(3) C2 0.012(4) 0.022(5) 0.013(4) -0.007(4) -0.002(3) -0.005(4) C3 0.009(4) 0.011(4) 0.020(5) -0.006(4) 0.002(3) -0.001(3) C4 0.017(4) 0.018(4) 0.013(4) -0.004(4) 0.003(3) -0.009(4) C5 0.022(5) 0.015(4) 0.015(5) -0.001(4) -0.002(4) -0.005(4) C6 0.012(4) 0.020(5) 0.018(5) -0.007(4) 0.007(4) -0.002(4) C7 0.022(5) 0.012(4) 0.022(5) -0.011(4) -0.005(4) 0.000(4) C8 0.024(5) 0.013(4) 0.019(5) -0.004(4) 0.003(4) -0.007(4) C9 0.008(4) 0.016(5) 0.072 -0.021(5) 0.012(5) -0.003(4) C10 0.020 0.030 0.050 0.020(5) -0.029(4) -0.010(4) C11 0.019(5) 0.018(4) 0.007(4) 0.006(3) -0.006(3) -0.009(4) C12 0.019(5) 0.005(4) 0.024(5) -0.001(4) -0.008(4) 0.008(3) C13 0.020(5) 0.026(5) 0.014(5) -0.005(4) -0.008(4) -0.007(4) C14 0.022(5) 0.016(4) 0.015(5) -0.003(4) 0.006(4) -0.008(4) C15 0.024(5) 0.026(5) 0.015(5) -0.010(4) -0.006(4) -0.002(4) C16 0.022(5) 0.022(5) 0.007(4) -0.005(4) -0.005(4) 0.004(4) C17 0.011(4) 0.006(4) 0.025(5) -0.009(3) -0.009(4) 0.003(3) C18 0.015(4) 0.016(4) 0.016(5) -0.007(4) 0.000(4) 0.000(4) C19 0.008 0.025 0.089 -0.042(4) 0.013(5) -0.011(3) C20 0.018(5) 0.024(5) 0.011(4) -0.007(4) 0.005(3) -0.006(4) C21 0.025(5) 0.010(4) 0.015(5) -0.002(3) -0.003(4) -0.006(4) C22 0.017(4) 0.022(5) 0.009(4) -0.005(4) 0.011(3) -0.004(4) C23 0.019(5) 0.016(4) 0.013(4) -0.004(4) -0.003(4) -0.004(4) C24 0.014(4) 0.021(5) 0.022(5) 0.003(4) 0.004(4) -0.007(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 Hg1 Cl2 2.305(3) . ? Hg1 Cl1 2.317(3) . ? Hg1 N1 2.487(8) . ? O1 C3 1.353(11) . ? O1 C2 1.425(11) . ? O2 N2 1.213(12) . ? O3 N2 1.241(12) . ? O4 C11 1.353(11) . ? O4 C10 1.449(16) . ? O5 N3 1.244(11) . ? O6 N3 1.222(12) . ? O7 C19 1.366(13) . ? O7 C18 1.413(11) . ? O8 N4 1.238(11) . ? O9 N4 1.208(11) . ? N1 C1 1.474(13) . ? N1 C9 1.494(15) . ? N1 C17 1.511(12) . ? N2 C6 1.472(13) . ? N3 C14 1.443(13) . ? N4 C22 1.473(12) . ? C1 C2 1.507(13) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C8 1.387(13) . ? C3 C4 1.409(13) . ? C4 C5 1.380(14) . ? C4 H4 0.9500 . ? C5 C6 1.383(14) . ? C5 H5 0.9500 . ? C6 C7 1.373(14) . ? C7 C8 1.376(14) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.528(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.391(14) . ? C11 C12 1.398(13) . ? C12 C13 1.375(14) . ? C12 H12 0.9500 . ? C13 C14 1.387(14) . ? C13 H13 0.9500 . ? C14 C15 1.396(14) . ? C15 C16 1.397(13) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.494(14) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.385(19) . ? C19 C20 1.391(17) . ? C20 C21 1.414(14) . ? C20 H20 0.9500 . ? C21 C22 1.355(13) . ? C21 H21 0.9500 . ? C22 C23 1.398(14) . ? C23 C24 1.390(14) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cl2 Hg1 Cl1 157.38(10) . . ? Cl2 Hg1 N1 102.92(19) . . ? Cl1 Hg1 N1 99.52(19) . . ? C3 O1 C2 118.4(7) . . ? C11 O4 C10 118.4(8) . . ? C19 O7 C18 118.7(9) . . ? C1 N1 C9 106.9(7) . . ? C1 N1 C17 112.0(7) . . ? C9 N1 C17 114.5(7) . . ? C1 N1 Hg1 104.4(6) . . ? C9 N1 Hg1 105.4(6) . . ? C17 N1 Hg1 112.9(5) . . ? O2 N2 O3 123.0(9) . . ? O2 N2 C6 119.3(9) . . ? O3 N2 C6 117.7(9) . . ? O6 N3 O5 123.1(9) . . ? O6 N3 C14 119.7(8) . . ? O5 N3 C14 117.2(9) . . ? O9 N4 O8 123.6(9) . . ? O9 N4 C22 119.0(8) . . ? O8 N4 C22 117.4(8) . . ? N1 C1 C2 113.7(8) . . ? N1 C1 H1A 108.8 . . ? C2 C1 H1A 108.8 . . ? N1 C1 H1B 108.8 . . ? C2 C1 H1B 108.8 . . ? H1A C1 H1B 107.7 . . ? O1 C2 C1 108.7(8) . . ? O1 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? O1 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.3 . . ? O1 C3 C8 116.2(9) . . ? O1 C3 C4 123.6(8) . . ? C8 C3 C4 120.2(9) . . ? C5 C4 C3 118.7(9) . . ? C5 C4 H4 120.6 . . ? C3 C4 H4 120.6 . . ? C4 C5 C6 119.8(9) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 121.7(9) . . ? C7 C6 N2 120.2(9) . . ? C5 C6 N2 118.1(9) . . ? C6 C7 C8 119.1(9) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C7 C8 C3 120.4(10) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? N1 C9 C10 114.9(8) . . ? N1 C9 H9A 108.6 . . ? C10 C9 H9A 108.6 . . ? N1 C9 H9B 108.6 . . ? C10 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? O4 C10 C9 105.5(8) . . ? O4 C10 H10A 110.6 . . ? C9 C10 H10A 110.6 . . ? O4 C10 H10B 110.6 . . ? C9 C10 H10B 110.6 . . ? H10A C10 H10B 108.8 . . ? O4 C11 C16 113.9(8) . . ? O4 C11 C12 125.3(9) . . ? C16 C11 C12 120.7(9) . . ? C13 C12 C11 119.0(10) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 120.3(9) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 121.8(9) . . ? C13 C14 N3 119.8(9) . . ? C15 C14 N3 118.4(9) . . ? C14 C15 C16 117.7(10) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? C11 C16 C15 120.5(9) . . ? C11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C18 C17 N1 116.0(7) . . ? C18 C17 H17A 108.3 . . ? N1 C17 H17A 108.3 . . ? C18 C17 H17B 108.3 . . ? N1 C17 H17B 108.3 . . ? H17A C17 H17B 107.4 . . ? O7 C18 C17 110.1(8) . . ? O7 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? O7 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.2 . . ? O7 C19 C24 123.7(11) . . ? O7 C19 C20 114.8(12) . . ? C24 C19 C20 121.4(10) . . ? C19 C20 C21 118.7(10) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C22 C21 C20 118.9(9) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C21 C22 C23 123.0(9) . . ? C21 C22 N4 119.6(9) . . ? C23 C22 N4 117.4(8) . . ? C24 C23 C22 118.1(9) . . ? C24 C23 H23 120.9 . . ? C22 C23 H23 120.9 . . ? C19 C24 C23 119.8(10) . . ? C19 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl2 Hg1 N1 C1 127.5(5) . . . . ? Cl1 Hg1 N1 C1 -55.3(5) . . . . ? Cl2 Hg1 N1 C9 -120.0(5) . . . . ? Cl1 Hg1 N1 C9 57.1(6) . . . . ? Cl2 Hg1 N1 C17 5.7(6) . . . . ? Cl1 Hg1 N1 C17 -177.2(5) . . . . ? C9 N1 C1 C2 176.4(8) . . . . ? C17 N1 C1 C2 50.2(10) . . . . ? Hg1 N1 C1 C2 -72.2(8) . . . . ? C3 O1 C2 C1 -179.0(8) . . . . ? N1 C1 C2 O1 56.4(10) . . . . ? C2 O1 C3 C8 173.2(8) . . . . ? C2 O1 C3 C4 -6.8(13) . . . . ? O1 C3 C4 C5 -178.1(9) . . . . ? C8 C3 C4 C5 1.9(14) . . . . ? C3 C4 C5 C6 -3.3(14) . . . . ? C4 C5 C6 C7 4.2(15) . . . . ? C4 C5 C6 N2 -178.9(9) . . . . ? O2 N2 C6 C7 178.5(10) . . . . ? O3 N2 C6 C7 -2.6(14) . . . . ? O2 N2 C6 C5 1.5(15) . . . . ? O3 N2 C6 C5 -179.6(9) . . . . ? C5 C6 C7 C8 -3.4(15) . . . . ? N2 C6 C7 C8 179.7(9) . . . . ? C6 C7 C8 C3 2.0(15) . . . . ? O1 C3 C8 C7 178.8(9) . . . . ? C4 C3 C8 C7 -1.2(14) . . . . ? C1 N1 C9 C10 179.8(9) . . . . ? C17 N1 C9 C10 -55.6(12) . . . . ? Hg1 N1 C9 C10 69.1(10) . . . . ? C11 O4 C10 C9 -174.9(9) . . . . ? N1 C9 C10 O4 -58.6(12) . . . . ? C10 O4 C11 C16 -177.5(9) . . . . ? C10 O4 C11 C12 3.9(14) . . . . ? O4 C11 C12 C13 -179.7(9) . . . . ? C16 C11 C12 C13 1.8(15) . . . . ? C11 C12 C13 C14 -0.8(15) . . . . ? C12 C13 C14 C15 -0.8(16) . . . . ? C12 C13 C14 N3 -179.6(9) . . . . ? O6 N3 C14 C13 25.6(14) . . . . ? O5 N3 C14 C13 -157.0(9) . . . . ? O6 N3 C14 C15 -153.2(10) . . . . ? O5 N3 C14 C15 24.2(13) . . . . ? C13 C14 C15 C16 1.4(16) . . . . ? N3 C14 C15 C16 -179.8(9) . . . . ? O4 C11 C16 C15 -179.9(9) . . . . ? C12 C11 C16 C15 -1.3(15) . . . . ? C14 C15 C16 C11 -0.3(16) . . . . ? C1 N1 C17 C18 51.5(10) . . . . ? C9 N1 C17 C18 -70.4(11) . . . . ? Hg1 N1 C17 C18 168.9(6) . . . . ? C19 O7 C18 C17 -157.9(8) . . . . ? N1 C17 C18 O7 69.6(10) . . . . ? C18 O7 C19 C24 -14.9(14) . . . . ? C18 O7 C19 C20 167.4(9) . . . . ? O7 C19 C20 C21 -179.2(9) . . . . ? C24 C19 C20 C21 3.1(15) . . . . ? C19 C20 C21 C22 -1.2(14) . . . . ? C20 C21 C22 C23 0.0(15) . . . . ? C20 C21 C22 N4 177.8(9) . . . . ? O9 N4 C22 C21 179.6(10) . . . . ? O8 N4 C22 C21 1.1(14) . . . . ? O9 N4 C22 C23 -2.5(14) . . . . ? O8 N4 C22 C23 179.0(9) . . . . ? C21 C22 C23 C24 -0.6(15) . . . . ? N4 C22 C23 C24 -178.5(9) . . . . ? O7 C19 C24 C23 178.7(9) . . . . ? C20 C19 C24 C23 -3.8(15) . . . . ? C22 C23 C24 C19 2.5(14) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 3.764 _refine_diff_density_min -5.049 _refine_diff_density_rms 0.443 # Attachment 'Data5, old CCDC no 657113.doc' data_Compound5.CIF _database_code_depnum_ccdc_archive 'CCDC 657113' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C27 H25 N4 O3), C2 H3 N, 2(F6 P)' _chemical_formula_sum 'C56 H53 F12 N9 O6 P2' _chemical_formula_weight 1238.01 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_HALL '-C 2yc' 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 29.780(4) _cell_length_b 10.3967(11) _cell_length_c 21.165(3) _cell_angle_alpha 90.00 _cell_angle_beta 120.922(4) _cell_angle_gamma 90.00 _cell_volume 5621.6(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(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 0.26 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.463 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2552 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9554 _exptl_absorpt_correction_T_max 0.9672 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 18407 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.32 _reflns_number_total 6929 _reflns_number_gt 4473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _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^)+(0.0475P)^2^+12.1510P] 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 6929 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1106 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1614 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.17050(3) 0.36675(7) 0.34355(4) 0.02341(19) Uani 1 1 d . . . F1 F 0.21493(8) 0.36536(19) 0.42837(10) 0.0452(6) Uani 1 1 d . . . F2 F 0.14053(8) 0.25287(17) 0.35807(10) 0.0334(5) Uani 1 1 d . . . F3 F 0.20165(7) 0.26098(18) 0.32584(11) 0.0360(5) Uani 1 1 d . . . F4 F 0.12557(7) 0.36796(18) 0.25847(10) 0.0354(5) Uani 1 1 d . . . F5 F 0.20025(8) 0.47900(18) 0.32836(11) 0.0389(5) Uani 1 1 d . . . F6 F 0.13868(8) 0.47131(17) 0.36044(10) 0.0345(5) Uani 1 1 d . . . N1 N 0.14405(9) 0.8921(2) 0.30039(12) 0.0198(5) Uani 1 1 d . . . H1N H 0.1583 0.9034 0.2681 0.030 Uiso 1 1 d . . . N2 N 0.04156(12) 0.9107(3) -0.13657(17) 0.0429(8) Uani 1 1 d . . . N3 N 0.00045(11) 0.5254(3) -0.09167(14) 0.0337(7) Uani 1 1 d . . . N4 N 0.20397(11) 0.9901(3) 0.73449(14) 0.0300(6) Uani 1 1 d . . . N5 N 0.0000 0.3132(6) 0.7500 0.0715(16) Uani 1 2 d S . . O1 O 0.07732(8) 0.99456(19) 0.15481(11) 0.0260(5) Uani 1 1 d . . . O2 O 0.15140(8) 0.72461(19) 0.20536(11) 0.0241(5) Uani 1 1 d . . . O3 O 0.18165(9) 0.80942(19) 0.45395(11) 0.0271(5) Uani 1 1 d . . . C1 C 0.09412(12) 0.9672(3) 0.27436(16) 0.0260(7) Uani 1 1 d . . . H1A H 0.0640 0.9074 0.2524 0.031 Uiso 1 1 calc R . . H1B H 0.0953 1.0099 0.3170 0.031 Uiso 1 1 calc R . . C2 C 0.08680(12) 1.0660(3) 0.21873(16) 0.0280(7) Uani 1 1 d . . . H2A H 0.0567 1.1223 0.2069 0.034 Uiso 1 1 calc R . . H2B H 0.1186 1.1199 0.2374 0.034 Uiso 1 1 calc R . . C3 C 0.06919(11) 1.0633(3) 0.09481(16) 0.0243(7) Uani 1 1 d . . . C4 C 0.06418(11) 0.9904(3) 0.03669(16) 0.0243(7) Uani 1 1 d . . . H4 H 0.0679 0.8995 0.0409 0.029 Uiso 1 1 calc R . . C5 C 0.05367(12) 1.0519(3) -0.02794(17) 0.0290(7) Uani 1 1 d . . . C6 C 0.04890(12) 1.1850(3) -0.03464(19) 0.0347(8) Uani 1 1 d . . . H6 H 0.0418 1.2265 -0.0788 0.042 Uiso 1 1 calc R . . C7 C 0.05466(13) 1.2548(3) 0.02409(19) 0.0363(8) Uani 1 1 d . . . H7 H 0.0517 1.3458 0.0202 0.044 Uiso 1 1 calc R . . C8 C 0.06470(12) 1.1962(3) 0.08889(18) 0.0311(8) Uani 1 1 d . . . H8 H 0.0685 1.2465 0.1288 0.037 Uiso 1 1 calc R . . C9 C 0.04716(12) 0.9735(4) -0.08843(18) 0.0326(8) Uani 1 1 d . . . C10 C 0.13648(12) 0.7485(3) 0.30218(16) 0.0245(7) Uani 1 1 d . . . H10A H 0.1130 0.7307 0.3214 0.029 Uiso 1 1 calc R . . H10B H 0.1706 0.7065 0.3351 0.029 Uiso 1 1 calc R . . C11 C 0.11274(11) 0.6960(3) 0.22471(15) 0.0212(6) Uani 1 1 d . . . H11A H 0.1067 0.6022 0.2236 0.025 Uiso 1 1 calc R . . H11B H 0.0791 0.7391 0.1907 0.025 Uiso 1 1 calc R . . C12 C 0.13879(12) 0.7066(3) 0.13397(16) 0.0220(6) Uani 1 1 d . . . C13 C 0.09306(11) 0.6480(3) 0.08102(15) 0.0207(6) Uani 1 1 d . . . H13 H 0.0681 0.6164 0.0925 0.025 Uiso 1 1 calc R . . C14 C 0.08476(12) 0.6369(3) 0.00912(16) 0.0230(6) Uani 1 1 d . . . C15 C 0.12062(12) 0.6820(3) -0.00815(16) 0.0261(7) Uani 1 1 d . . . H15 H 0.1139 0.6753 -0.0570 0.031 Uiso 1 1 calc R . . C16 C 0.16698(13) 0.7377(3) 0.04698(17) 0.0270(7) Uani 1 1 d . . . H16 H 0.1924 0.7676 0.0360 0.032 Uiso 1 1 calc R . . C17 C 0.17593(12) 0.7494(3) 0.11764(16) 0.0233(6) Uani 1 1 d . . . H17 H 0.2076 0.7869 0.1552 0.028 Uiso 1 1 calc R . . C18 C 0.03714(12) 0.5758(3) -0.04709(16) 0.0258(7) Uani 1 1 d . . . C19 C 0.18955(11) 0.9451(3) 0.37023(15) 0.0222(6) Uani 1 1 d . . . H19A H 0.2213 0.8968 0.3808 0.027 Uiso 1 1 calc R . . H19B H 0.1949 1.0357 0.3611 0.027 Uiso 1 1 calc R . . C20 C 0.18532(12) 0.9415(3) 0.43804(15) 0.0236(6) Uani 1 1 d . . . H20A H 0.2165 0.9819 0.4800 0.028 Uiso 1 1 calc R . . H20B H 0.1539 0.9893 0.4293 0.028 Uiso 1 1 calc R . . C21 C 0.18476(11) 0.7802(3) 0.51928(15) 0.0207(6) Uani 1 1 d . . . C22 C 0.19321(11) 0.8695(3) 0.57262(15) 0.0221(6) Uani 1 1 d . . . H22 H 0.1966 0.9584 0.5655 0.027 Uiso 1 1 calc R . . C23 C 0.19661(11) 0.8256(3) 0.63743(16) 0.0221(6) Uani 1 1 d . . . C24 C 0.19179(12) 0.6962(3) 0.64893(16) 0.0243(6) Uani 1 1 d . . . H24 H 0.1947 0.6680 0.6936 0.029 Uiso 1 1 calc R . . C25 C 0.18266(12) 0.6090(3) 0.59431(17) 0.0245(7) Uani 1 1 d . . . H25 H 0.1791 0.5202 0.6013 0.029 Uiso 1 1 calc R . . C26 C 0.17866(11) 0.6502(3) 0.52970(16) 0.0228(6) Uani 1 1 d . . . H26 H 0.1717 0.5898 0.4921 0.027 Uiso 1 1 calc R . . C27 C 0.20207(12) 0.9183(3) 0.69193(16) 0.0244(7) Uani 1 1 d . . . C28 C 0.0000 0.4229(7) 0.7500 0.0499(14) Uani 1 2 d S . . C29 C 0.0000 0.5639(5) 0.7500 0.0459(13) Uani 1 2 d S . . H29A H -0.0003 0.5953 0.7061 0.069 Uiso 0.50 1 calc PR . . H29B H 0.0315 0.5953 0.7943 0.069 Uiso 0.50 1 calc PR . . H29C H -0.0312 0.5953 0.7496 0.069 Uiso 0.50 1 calc PR . . 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 0.0260(4) 0.0221(4) 0.0222(4) -0.0042(3) 0.0125(3) -0.0032(3) F1 0.0477(13) 0.0373(11) 0.0270(10) -0.0033(9) 0.0025(9) 0.0005(9) F2 0.0511(12) 0.0238(9) 0.0408(11) -0.0077(8) 0.0347(10) -0.0073(8) F3 0.0370(11) 0.0317(10) 0.0477(12) -0.0040(9) 0.0278(10) 0.0020(8) F4 0.0376(11) 0.0350(11) 0.0255(10) -0.0030(8) 0.0104(9) -0.0014(9) F5 0.0412(11) 0.0288(10) 0.0530(13) -0.0051(9) 0.0286(10) -0.0102(8) F6 0.0486(12) 0.0249(10) 0.0390(11) -0.0050(8) 0.0289(10) 0.0026(8) N1 0.0228(13) 0.0207(12) 0.0158(12) 0.0012(9) 0.0099(10) 0.0011(10) N2 0.0355(17) 0.064(2) 0.0323(17) 0.0047(16) 0.0194(14) -0.0002(15) N3 0.0360(16) 0.0378(16) 0.0227(14) -0.0004(12) 0.0118(13) -0.0074(13) N4 0.0418(17) 0.0295(15) 0.0214(14) -0.0034(11) 0.0181(12) -0.0042(12) N5 0.058(4) 0.061(4) 0.098(5) 0.000 0.042(3) 0.000 O1 0.0333(12) 0.0203(11) 0.0177(10) 0.0003(8) 0.0084(9) 0.0012(9) O2 0.0291(12) 0.0262(11) 0.0192(10) -0.0041(8) 0.0140(9) -0.0016(9) O3 0.0436(13) 0.0212(11) 0.0175(10) 0.0003(8) 0.0166(10) -0.0024(9) C1 0.0234(16) 0.0307(17) 0.0248(16) -0.0054(13) 0.0130(13) 0.0025(13) C2 0.0276(17) 0.0223(16) 0.0259(16) -0.0040(13) 0.0078(13) 0.0035(13) C3 0.0196(15) 0.0230(15) 0.0225(15) 0.0005(12) 0.0053(12) -0.0021(12) C4 0.0173(14) 0.0237(15) 0.0278(16) 0.0056(12) 0.0086(12) -0.0034(12) C5 0.0187(15) 0.0363(18) 0.0292(17) 0.0060(14) 0.0103(13) -0.0018(13) C6 0.0255(17) 0.0373(19) 0.0374(19) 0.0182(16) 0.0135(15) 0.0016(14) C7 0.0293(18) 0.0249(17) 0.045(2) 0.0097(15) 0.0125(16) 0.0031(14) C8 0.0263(17) 0.0248(16) 0.0292(17) -0.0011(13) 0.0051(14) 0.0012(13) C9 0.0238(17) 0.050(2) 0.0251(17) 0.0113(16) 0.0131(14) 0.0024(15) C10 0.0315(17) 0.0206(15) 0.0218(15) -0.0010(12) 0.0140(13) -0.0030(12) C11 0.0269(16) 0.0230(15) 0.0162(14) -0.0001(11) 0.0128(12) -0.0026(12) C12 0.0314(16) 0.0163(14) 0.0223(15) -0.0026(11) 0.0167(13) 0.0026(12) C13 0.0244(15) 0.0169(14) 0.0220(15) 0.0004(11) 0.0127(12) 0.0019(11) C14 0.0304(16) 0.0184(14) 0.0189(15) 0.0010(11) 0.0118(13) 0.0003(12) C15 0.0389(18) 0.0210(15) 0.0203(15) 0.0012(12) 0.0166(14) 0.0023(13) C16 0.0339(18) 0.0220(16) 0.0342(18) -0.0001(13) 0.0240(15) -0.0021(13) C17 0.0263(16) 0.0198(15) 0.0239(16) -0.0039(12) 0.0130(13) -0.0013(12) C18 0.0324(18) 0.0273(16) 0.0171(15) 0.0039(12) 0.0123(14) 0.0008(13) C19 0.0249(15) 0.0195(15) 0.0213(15) -0.0022(11) 0.0111(12) -0.0007(11) C20 0.0303(16) 0.0212(15) 0.0183(14) 0.0016(11) 0.0118(13) -0.0013(12) C21 0.0225(15) 0.0225(15) 0.0175(14) 0.0032(11) 0.0105(12) -0.0003(11) C22 0.0225(15) 0.0204(15) 0.0229(15) 0.0021(12) 0.0113(12) -0.0003(12) C23 0.0226(15) 0.0251(15) 0.0209(15) -0.0013(12) 0.0128(12) -0.0024(12) C24 0.0271(16) 0.0268(16) 0.0216(15) 0.0060(12) 0.0143(13) 0.0015(13) C25 0.0265(16) 0.0199(15) 0.0311(17) 0.0031(12) 0.0177(14) -0.0015(12) C26 0.0235(15) 0.0215(15) 0.0219(15) -0.0036(12) 0.0108(12) -0.0018(12) C27 0.0285(16) 0.0264(16) 0.0205(15) 0.0029(13) 0.0141(13) -0.0013(13) C28 0.041(3) 0.061(4) 0.053(4) 0.000 0.028(3) 0.000 C29 0.051(3) 0.055(4) 0.033(3) 0.000 0.023(3) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F1 1.591(2) . ? P1 F5 1.595(2) . ? P1 F6 1.5986(19) . ? P1 F4 1.5990(19) . ? P1 F3 1.602(2) . ? P1 F2 1.6045(19) . ? N1 C19 1.506(4) . ? N1 C1 1.510(4) . ? N1 C10 1.513(4) . ? N1 H1N 0.9794 . ? N2 C9 1.148(4) . ? N3 C18 1.140(4) . ? N4 C27 1.148(4) . ? N5 C28 1.140(8) . ? O1 C3 1.366(3) . ? O1 C2 1.438(3) . ? O2 C12 1.369(3) . ? O2 C11 1.437(3) . ? O3 C21 1.372(3) . ? O3 C20 1.432(3) . ? C1 C2 1.492(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.386(4) . ? C3 C8 1.388(4) . ? C4 C5 1.392(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(5) . ? C5 C9 1.444(5) . ? C6 C7 1.372(5) . ? C6 H6 0.9500 . ? C7 C8 1.386(5) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C10 C11 1.515(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.383(4) . ? C12 C17 1.391(4) . ? C13 C14 1.416(4) . ? C13 H13 0.9500 . ? C14 C15 1.376(4) . ? C14 C18 1.448(4) . ? C15 C16 1.396(4) . ? C15 H15 0.9500 . ? C16 C17 1.383(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C19 C20 1.504(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.381(4) . ? C21 C26 1.396(4) . ? C22 C23 1.399(4) . ? C22 H22 0.9500 . ? C23 C24 1.388(4) . ? C23 C27 1.446(4) . ? C24 C25 1.382(4) . ? C24 H24 0.9500 . ? C25 C26 1.378(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C28 C29 1.466(8) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 F1 P1 F5 90.46(12) . . ? F1 P1 F6 89.93(11) . . ? F5 P1 F6 90.12(11) . . ? F1 P1 F4 179.61(13) . . ? F5 P1 F4 89.85(11) . . ? F6 P1 F4 89.84(11) . . ? F1 P1 F3 90.69(11) . . ? F5 P1 F3 90.38(11) . . ? F6 P1 F3 179.20(12) . . ? F4 P1 F3 89.54(10) . . ? F1 P1 F2 89.95(11) . . ? F5 P1 F2 179.33(11) . . ? F6 P1 F2 90.40(10) . . ? F4 P1 F2 89.74(10) . . ? F3 P1 F2 89.09(10) . . ? C19 N1 C1 112.9(2) . . ? C19 N1 C10 114.0(2) . . ? C1 N1 C10 112.8(2) . . ? C19 N1 H1N 98.4 . . ? C1 N1 H1N 112.4 . . ? C10 N1 H1N 105.0 . . ? C3 O1 C2 117.4(2) . . ? C12 O2 C11 118.7(2) . . ? C21 O3 C20 118.4(2) . . ? C2 C1 N1 111.2(2) . . ? C2 C1 H1A 109.4 . . ? N1 C1 H1A 109.4 . . ? C2 C1 H1B 109.4 . . ? N1 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? O1 C2 C1 105.4(2) . . ? O1 C2 H2A 110.7 . . ? C1 C2 H2A 110.7 . . ? O1 C2 H2B 110.7 . . ? C1 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? O1 C3 C4 115.2(3) . . ? O1 C3 C8 124.6(3) . . ? C4 C3 C8 120.2(3) . . ? C3 C4 C5 119.2(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 121.1(3) . . ? C6 C5 C9 120.7(3) . . ? C4 C5 C9 118.1(3) . . ? C7 C6 C5 118.4(3) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C6 C7 C8 121.8(3) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C7 C8 C3 119.3(3) . . ? C7 C8 H8 120.4 . . ? C3 C8 H8 120.4 . . ? N2 C9 C5 179.4(4) . . ? N1 C10 C11 108.7(2) . . ? N1 C10 H10A 109.9 . . ? C11 C10 H10A 109.9 . . ? N1 C10 H10B 109.9 . . ? C11 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? O2 C11 C10 103.7(2) . . ? O2 C11 H11A 111.0 . . ? C10 C11 H11A 111.0 . . ? O2 C11 H11B 111.0 . . ? C10 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? O2 C12 C13 123.5(3) . . ? O2 C12 C17 115.4(3) . . ? C13 C12 C17 121.1(3) . . ? C12 C13 C14 117.5(3) . . ? C12 C13 H13 121.2 . . ? C14 C13 H13 121.2 . . ? C15 C14 C13 121.8(3) . . ? C15 C14 C18 119.8(3) . . ? C13 C14 C18 118.4(3) . . ? C14 C15 C16 119.2(3) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C17 C16 C15 119.9(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C12 120.3(3) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? N3 C18 C14 178.1(4) . . ? C20 C19 N1 116.9(2) . . ? C20 C19 H19A 108.1 . . ? N1 C19 H19A 108.1 . . ? C20 C19 H19B 108.1 . . ? N1 C19 H19B 108.1 . . ? H19A C19 H19B 107.3 . . ? O3 C20 C19 107.6(2) . . ? O3 C20 H20A 110.2 . . ? C19 C20 H20A 110.2 . . ? O3 C20 H20B 110.2 . . ? C19 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? O3 C21 C22 124.4(3) . . ? O3 C21 C26 115.3(3) . . ? C22 C21 C26 120.4(3) . . ? C21 C22 C23 118.2(3) . . ? C21 C22 H22 120.9 . . ? C23 C22 H22 120.9 . . ? C24 C23 C22 121.7(3) . . ? C24 C23 C27 119.0(3) . . ? C22 C23 C27 119.1(3) . . ? C25 C24 C23 118.9(3) . . ? C25 C24 H24 120.6 . . ? C23 C24 H24 120.6 . . ? C26 C25 C24 120.4(3) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C21 120.4(3) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? N4 C27 C23 176.6(3) . . ? N5 C28 C29 180.000(5) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? 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 C19 N1 C1 C2 95.0(3) . . . . ? C10 N1 C1 C2 -133.9(2) . . . . ? C3 O1 C2 C1 180.0(2) . . . . ? N1 C1 C2 O1 67.9(3) . . . . ? C2 O1 C3 C4 175.3(3) . . . . ? C2 O1 C3 C8 -6.2(4) . . . . ? O1 C3 C4 C5 177.4(3) . . . . ? C8 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? C3 C4 C5 C9 -178.3(3) . . . . ? C4 C5 C6 C7 -0.2(5) . . . . ? C9 C5 C6 C7 179.0(3) . . . . ? C5 C6 C7 C8 -0.4(5) . . . . ? C6 C7 C8 C3 0.2(5) . . . . ? O1 C3 C8 C7 -177.8(3) . . . . ? C4 C3 C8 C7 0.6(5) . . . . ? C6 C5 C9 N2 -110(100) . . . . ? C4 C5 C9 N2 69(59) . . . . ? C19 N1 C10 C11 -149.8(2) . . . . ? C1 N1 C10 C11 79.6(3) . . . . ? C12 O2 C11 C10 -170.4(2) . . . . ? N1 C10 C11 O2 61.5(3) . . . . ? C11 O2 C12 C13 -8.0(4) . . . . ? C11 O2 C12 C17 173.2(2) . . . . ? O2 C12 C13 C14 179.4(3) . . . . ? C17 C12 C13 C14 -1.9(4) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C12 C13 C14 C18 180.0(3) . . . . ? C13 C14 C15 C16 1.4(4) . . . . ? C18 C14 C15 C16 -178.4(3) . . . . ? C14 C15 C16 C17 -1.3(4) . . . . ? C15 C16 C17 C12 -0.4(4) . . . . ? O2 C12 C17 C16 -179.1(3) . . . . ? C13 C12 C17 C16 2.1(4) . . . . ? C15 C14 C18 N3 57(11) . . . . ? C13 C14 C18 N3 -123(11) . . . . ? C1 N1 C19 C20 63.6(3) . . . . ? C10 N1 C19 C20 -66.9(3) . . . . ? C21 O3 C20 C19 171.0(2) . . . . ? N1 C19 C20 O3 62.2(3) . . . . ? C20 O3 C21 C22 -2.5(4) . . . . ? C20 O3 C21 C26 177.4(3) . . . . ? O3 C21 C22 C23 -178.7(3) . . . . ? C26 C21 C22 C23 1.4(4) . . . . ? C21 C22 C23 C24 0.1(4) . . . . ? C21 C22 C23 C27 -176.0(3) . . . . ? C22 C23 C24 C25 -0.9(4) . . . . ? C27 C23 C24 C25 175.2(3) . . . . ? C23 C24 C25 C26 0.3(4) . . . . ? C24 C25 C26 C21 1.2(4) . . . . ? O3 C21 C26 C25 178.0(3) . . . . ? C22 C21 C26 C25 -2.1(4) . . . . ? C24 C23 C27 N4 -62(6) . . . . ? C22 C23 C27 N4 114(5) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.451 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.086 # Attachment 'Compound 6, old CCDC no 657114.doc' data_Compound6.CIF _database_code_depnum_ccdc_archive 'CCDC 657114' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C27 H25 N4 O3), F8 P, F6 P' _chemical_formula_sum 'C54 H50 F14 N8 O6 P2 ' _chemical_formula_weight 1234.96 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' P P 0.1023 0.0942 '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' 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' _symmetry_Int_Tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 13.3330(17) _cell_length_b 13.3330(17) _cell_length_c 26.773(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 4121.8(10) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 600 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max +28.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1902 _exptl_absorpt_coefficient_mu 0.185 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9586 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed-tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method phi-omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6983 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 24.71 _reflns_number_total 1564 _reflns_number_gt 1344 _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^)+(0.0701P)^2^+15.5923P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0006(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1564 _refine_ls_number_parameters 129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1548 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.6667 0.3333 0.8333 0.0141(5) Uani 1 6 d S . . P2 P 0.0000 0.0000 0.0000 0.0487(7) Uani 1 6 d S . . F1 F 0.55617(14) 0.25736(15) 0.86784(6) 0.0260(5) Uani 1 1 d . . . F2 F 0.0000 0.0000 -0.05923(15) 0.0677(13) Uani 1 3 d S . . F3 F -0.049(5) 0.080(4) 0.0012(3) 0.245(7) Uani 1 1 d . . . O1 O 0.06667(17) 0.17328(17) 0.74760(7) 0.0200(5) Uani 1 1 d . . . N1 N 0.0000 0.0000 0.68028(14) 0.0154(9) Uani 1 3 d S . . H1N H 0.0000 0.0000 0.7138 0.020 Uiso 1 3 d S . . N2 N -0.0235(2) 0.4288(2) 0.94441(10) 0.0272(7) Uani 1 1 d . . . C1 C 0.0776(2) 0.1237(2) 0.66464(10) 0.0176(7) Uani 1 1 d . . . H1A H 0.0624 0.1334 0.6293 0.021 Uiso 1 1 calc R . . H1B H 0.1596 0.1438 0.6676 0.021 Uiso 1 1 calc R . . C2 C 0.0561(3) 0.2035(3) 0.69725(10) 0.0192(7) Uani 1 1 d . . . H2B H 0.1139 0.2855 0.6904 0.023 Uiso 1 1 calc R . . H2A H -0.0223 0.1918 0.6912 0.023 Uiso 1 1 calc R . . C3 C 0.0398(2) 0.2249(2) 0.78550(10) 0.0170(6) Uani 1 1 d . . . C4 C 0.0124(2) 0.3117(3) 0.77835(11) 0.0206(7) Uani 1 1 d . . . H4 H 0.0079 0.3365 0.7456 0.025 Uiso 1 1 calc R . . C5 C -0.0082(2) 0.3616(3) 0.81957(11) 0.0207(7) Uani 1 1 d . . . H5 H -0.0266 0.4212 0.8152 0.025 Uiso 1 1 calc R . . C6 C -0.0020(2) 0.3244(2) 0.86733(10) 0.0192(7) Uani 1 1 d . . . C7 C 0.0230(2) 0.2354(2) 0.87419(11) 0.0193(7) Uani 1 1 d . . . H7 H 0.0259 0.2092 0.9069 0.023 Uiso 1 1 calc R . . C8 C 0.0434(2) 0.1859(2) 0.83325(10) 0.0183(7) Uani 1 1 d . . . H8 H 0.0599 0.1249 0.8376 0.022 Uiso 1 1 calc R . . C9 C -0.0156(2) 0.3817(3) 0.91012(12) 0.0207(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0137(6) 0.0137(6) 0.0149(9) 0.000 0.000 0.0068(3) P2 0.0581(11) 0.0581(11) 0.0300(13) 0.000 0.000 0.0290(5) F1 0.0195(9) 0.0266(10) 0.0261(10) 0.0048(8) 0.0068(7) 0.0072(8) F2 0.085(2) 0.085(2) 0.033(2) 0.000 0.000 0.0425(11) F3 0.447(19) 0.375(18) 0.113(3) 0.010(5) 0.017(5) 0.355(17) O1 0.0251(11) 0.0248(11) 0.0154(10) -0.0051(8) -0.0039(8) 0.0164(9) N1 0.0194(14) 0.0194(14) 0.0074(18) 0.000 0.000 0.0097(7) N2 0.0241(14) 0.0268(15) 0.0243(15) -0.0035(12) 0.0042(11) 0.0080(12) C1 0.0174(14) 0.0164(15) 0.0156(14) 0.0019(11) 0.0015(11) 0.0059(12) C2 0.0213(15) 0.0214(15) 0.0143(14) -0.0002(12) -0.0013(12) 0.0103(13) C3 0.0115(14) 0.0192(15) 0.0179(14) -0.0045(12) -0.0023(11) 0.0059(12) C4 0.0194(15) 0.0234(16) 0.0201(15) -0.0017(12) -0.0028(12) 0.0115(13) C5 0.0143(14) 0.0204(15) 0.0280(17) -0.0025(13) -0.0014(12) 0.0091(12) C6 0.0122(14) 0.0205(15) 0.0205(16) -0.0046(12) 0.0005(11) 0.0048(12) C7 0.0148(14) 0.0198(15) 0.0178(15) -0.0008(12) -0.0005(11) 0.0046(12) C8 0.0150(14) 0.0149(14) 0.0228(15) -0.0026(12) -0.0023(12) 0.0059(12) C9 0.0130(14) 0.0206(15) 0.0241(16) -0.0014(13) 0.0009(12) 0.0050(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 P1 F1 1.5993(16) 17_556 ? P1 F1 1.5993(16) 2_655 ? P1 F1 1.5993(17) . ? P1 F1 1.5993(16) 3_665 ? P1 F1 1.5993(17) 16_656 ? P1 F1 1.5994(16) 18_546 ? P2 F3 1.504(7) 3 ? P2 F3 1.504(7) 2 ? P2 F3 1.504(7) 11 ? P2 F3 1.504(7) . ? P2 F3 1.504(7) 10 ? P2 F3 1.504(7) 12 ? P2 F2 1.586(4) . ? P2 F2 1.586(4) 10 ? F3 F3 1.506(7) 11 ? F3 F3 1.506(7) 12 ? O1 C3 1.370(3) . ? O1 C2 1.434(3) . ? N1 C1 1.503(3) 2 ? N1 C1 1.503(3) . ? N1 C1 1.503(3) 3 ? N1 H1N 0.8975 . ? N2 C9 1.146(4) . ? C1 C2 1.511(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C3 C8 1.390(4) . ? C3 C4 1.390(4) . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.389(4) . ? C5 H5 0.9500 . ? C6 C7 1.397(4) . ? C6 C9 1.438(4) . ? C7 C8 1.375(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 P1 F1 180.00(11) 17_556 2_655 ? F1 P1 F1 90.04(9) 17_556 . ? F1 P1 F1 89.96(9) 2_655 . ? F1 P1 F1 90.04(9) 17_556 3_665 ? F1 P1 F1 89.96(9) 2_655 3_665 ? F1 P1 F1 89.96(9) . 3_665 ? F1 P1 F1 89.96(9) 17_556 16_656 ? F1 P1 F1 90.04(9) 2_655 16_656 ? F1 P1 F1 180.00(10) . 16_656 ? F1 P1 F1 90.04(9) 3_665 16_656 ? F1 P1 F1 89.96(9) 17_556 18_546 ? F1 P1 F1 90.04(9) 2_655 18_546 ? F1 P1 F1 90.04(9) . 18_546 ? F1 P1 F1 180.00(9) 3_665 18_546 ? F1 P1 F1 89.96(9) 16_656 18_546 ? F3 P2 F3 119.95(3) 3 2 ? F3 P2 F3 60.05(3) 3 11 ? F3 P2 F3 180.0(5) 2 11 ? F3 P2 F3 119.95(3) 3 . ? F3 P2 F3 119.95(3) 2 . ? F3 P2 F3 60.05(3) 11 . ? F3 P2 F3 60.05(3) 3 10 ? F3 P2 F3 60.05(3) 2 10 ? F3 P2 F3 119.95(3) 11 10 ? F3 P2 F3 180.0(13) . 10 ? F3 P2 F3 180(4) 3 12 ? F3 P2 F3 60.05(3) 2 12 ? F3 P2 F3 119.95(3) 11 12 ? F3 P2 F3 60.05(3) . 12 ? F3 P2 F3 119.95(3) 10 12 ? F3 P2 F2 91.3(3) 3 . ? F3 P2 F2 91.3(3) 2 . ? F3 P2 F2 88.7(3) 11 . ? F3 P2 F2 91.3(3) . . ? F3 P2 F2 88.7(3) 10 . ? F3 P2 F2 88.7(3) 12 . ? F3 P2 F2 88.7(3) 3 10 ? F3 P2 F2 88.7(3) 2 10 ? F3 P2 F2 91.3(3) 11 10 ? F3 P2 F2 88.7(3) . 10 ? F3 P2 F2 91.3(3) 10 10 ? F3 P2 F2 91.3(3) 12 10 ? F2 P2 F2 180.0 . 10 ? P2 F3 F3 59.976(14) . 11 ? P2 F3 F3 59.976(14) . 12 ? F3 F3 F3 119.81(11) 11 12 ? C3 O1 C2 117.9(2) . . ? C1 N1 C1 112.56(15) 2 . ? C1 N1 C1 112.56(15) 2 3 ? C1 N1 C1 112.56(15) . 3 ? C1 N1 H1N 106.2 2 . ? C1 N1 H1N 106.2 . . ? C1 N1 H1N 106.2 3 . ? N1 C1 C2 110.1(2) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.2 . . ? O1 C2 C1 105.4(2) . . ? O1 C2 H2B 110.7 . . ? C1 C2 H2B 110.7 . . ? O1 C2 H2A 110.7 . . ? C1 C2 H2A 110.7 . . ? H2B C2 H2A 108.8 . . ? O1 C3 C8 115.3(2) . . ? O1 C3 C4 124.0(3) . . ? C8 C3 C4 120.7(3) . . ? C5 C4 C3 119.2(3) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.1(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C7 120.4(3) . . ? C5 C6 C9 119.9(3) . . ? C7 C6 C9 119.6(3) . . ? C8 C7 C6 119.5(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C3 120.1(3) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? N2 C9 C6 178.3(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 F3 P2 F3 F3 4.4(12) 3 . . 11 ? F3 P2 F3 F3 180.0 2 . . 11 ? F3 P2 F3 F3 101(19) 10 . . 11 ? F3 P2 F3 F3 -175.6(12) 12 . . 11 ? F2 P2 F3 F3 -87.8(6) . . . 11 ? F2 P2 F3 F3 92.2(6) 10 . . 11 ? F3 P2 F3 F3 180.0 3 . . 12 ? F3 P2 F3 F3 -4.4(12) 2 . . 12 ? F3 P2 F3 F3 175.6(12) 11 . . 12 ? F3 P2 F3 F3 -84(19) 10 . . 12 ? F2 P2 F3 F3 87.8(6) . . . 12 ? F2 P2 F3 F3 -92.2(6) 10 . . 12 ? C1 N1 C1 C2 74.0(4) 2 . . . ? C1 N1 C1 C2 -157.5(2) 3 . . . ? C3 O1 C2 C1 -173.7(2) . . . . ? N1 C1 C2 O1 52.6(3) . . . . ? C2 O1 C3 C8 175.4(2) . . . . ? C2 O1 C3 C4 -5.6(4) . . . . ? O1 C3 C4 C5 -177.1(3) . . . . ? C8 C3 C4 C5 1.8(4) . . . . ? C3 C4 C5 C6 -0.3(4) . . . . ? C4 C5 C6 C7 -1.1(4) . . . . ? C4 C5 C6 C9 175.7(3) . . . . ? C5 C6 C7 C8 1.1(4) . . . . ? C9 C6 C7 C8 -175.8(3) . . . . ? C6 C7 C8 C3 0.5(4) . . . . ? O1 C3 C8 C7 177.1(2) . . . . ? C4 C3 C8 C7 -1.9(4) . . . . ? C5 C6 C9 N2 -103(11) . . . . ? C7 C6 C9 N2 74(11) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.326 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.084