# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'A Cowley' _publ_contact_author_email COWLEY@MAIL.UTEXAS.EDU _publ_section_title ; Facile syntheses of thiophene-substituted 1,4-diazabutadiene (?-diimine) ligands and their conversion to phosphenium triiodide salts ; loop_ _publ_author_name 'A Cowley' 'Jaclyn R. Brown' 'Adam Powell' 'Kalyan Vasudevan' # Attachment 'apap001b.cif' data_apap001b _database_code_depnum_ccdc_archive 'CCDC 707513' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H14 F2 N2 S2' _chemical_formula_sum 'C22 H14 F2 N2 S2' _chemical_formula_weight 408.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M I2/a _symmetry_space_group_name_Hall -I2ya loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 20.280(4) _cell_length_b 8.5334(17) _cell_length_c 22.959(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.53(3) _cell_angle_gamma 90.00 _cell_volume 3809.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 11971 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.308 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7008 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4309 _reflns_number_gt 2522 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4309 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1172 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _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 S2 S 0.66491(4) 0.14678(10) 0.01268(4) 0.0263(2) Uani 1 1 d . . . S1 S 0.57080(4) 0.62939(11) 0.17829(4) 0.0254(2) Uani 1 1 d . . . F1 F 0.97895(10) 0.2567(3) 0.26268(9) 0.0374(5) Uani 1 1 d . . . F2 F 0.91600(11) 0.9473(3) 0.12680(10) 0.0425(6) Uani 1 1 d . . . N1 N 0.71670(14) 0.5097(3) 0.19480(11) 0.0199(6) Uani 1 1 d . . . N2 N 0.74000(13) 0.4405(3) 0.06417(11) 0.0189(6) Uani 1 1 d . . . C7 C 0.65423(16) 0.2610(4) 0.07148(13) 0.0195(7) Uani 1 1 d . . . C11 C 0.78300(16) 0.4391(4) 0.21106(13) 0.0186(7) Uani 1 1 d . . . C1 C 0.67659(16) 0.4954(4) 0.14061(13) 0.0175(7) Uani 1 1 d . . . C17 C 0.78151(16) 0.5755(4) 0.08031(13) 0.0188(7) Uani 1 1 d . . . C12 C 0.83868(17) 0.5323(4) 0.24019(14) 0.0247(8) Uani 1 1 d . . . H12 H 0.8314 0.6365 0.2486 0.030 Uiso 1 1 calc R . . C15 C 0.85984(17) 0.2188(4) 0.21880(14) 0.0234(7) Uani 1 1 d . . . H15 H 0.8674 0.1134 0.2126 0.028 Uiso 1 1 calc R . . C16 C 0.79402(17) 0.2814(4) 0.20127(13) 0.0207(7) Uani 1 1 d . . . H16 H 0.7568 0.2173 0.1828 0.025 Uiso 1 1 calc R . . C19 C 0.80260(19) 0.8501(4) 0.10187(16) 0.0314(8) Uani 1 1 d . . . H19 H 0.7866 0.9506 0.1058 0.038 Uiso 1 1 calc R . . C2 C 0.69385(15) 0.4041(4) 0.08991(13) 0.0168(7) Uani 1 1 d . . . C3 C 0.60855(15) 0.5673(4) 0.12389(13) 0.0170(7) Uani 1 1 d . . . C10 C 0.60837(19) 0.0112(4) 0.02421(16) 0.0310(9) Uani 1 1 d . . . H10 H 0.5965 -0.0790 0.0009 0.037 Uiso 1 1 calc R . . C9 C 0.5826(2) 0.0472(4) 0.07019(16) 0.0329(9) Uani 1 1 d . . . H9 H 0.5514 -0.0157 0.0822 0.040 Uiso 1 1 calc R . . C18 C 0.75737(18) 0.7255(4) 0.08654(15) 0.0250(8) Uani 1 1 d . . . H18 H 0.7105 0.7419 0.0804 0.030 Uiso 1 1 calc R . . C13 C 0.90508(18) 0.4727(4) 0.25703(15) 0.0281(8) Uani 1 1 d . . . H13 H 0.9426 0.5359 0.2754 0.034 Uiso 1 1 calc R . . C20 C 0.87170(19) 0.8230(4) 0.11115(15) 0.0269(8) Uani 1 1 d . . . C5 C 0.50442(17) 0.6718(4) 0.06667(16) 0.0251(8) Uani 1 1 d . . . H5 H 0.4705 0.7019 0.0319 0.030 Uiso 1 1 calc R . . C6 C 0.50008(17) 0.6946(4) 0.12407(16) 0.0263(8) Uani 1 1 d . . . H6 H 0.4625 0.7410 0.1328 0.032 Uiso 1 1 calc R . . C21 C 0.89748(18) 0.6786(4) 0.10419(15) 0.0286(8) Uani 1 1 d . . . H21 H 0.9444 0.6636 0.1107 0.034 Uiso 1 1 calc R . . C14 C 0.91366(17) 0.3176(4) 0.24567(14) 0.0246(8) Uani 1 1 d . . . C4 C 0.56652(16) 0.5969(4) 0.06589(14) 0.0210(7) Uani 1 1 d . . . H4 H 0.5777 0.5707 0.0306 0.025 Uiso 1 1 calc R . . C8 C 0.60801(17) 0.1923(4) 0.09868(14) 0.0223(7) Uani 1 1 d . . . H8 H 0.5954 0.2355 0.1312 0.027 Uiso 1 1 calc R . . C22 C 0.85177(17) 0.5551(4) 0.08722(14) 0.0244(8) Uani 1 1 d . . . H22 H 0.8680 0.4570 0.0803 0.029 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 S2 0.0247(5) 0.0251(5) 0.0290(5) -0.0078(4) 0.0076(3) 0.0001(4) S1 0.0216(5) 0.0269(5) 0.0286(5) -0.0051(4) 0.0088(3) 0.0020(4) F1 0.0214(11) 0.0459(14) 0.0418(12) 0.0046(10) 0.0038(9) 0.0096(10) F2 0.0400(14) 0.0321(13) 0.0533(14) -0.0032(11) 0.0098(11) -0.0187(11) N1 0.0220(15) 0.0195(14) 0.0178(13) -0.0033(11) 0.0048(11) -0.0036(12) N2 0.0166(14) 0.0217(15) 0.0181(13) 0.0002(11) 0.0045(11) -0.0024(12) C7 0.0186(17) 0.0191(17) 0.0189(16) -0.0013(13) 0.0023(13) 0.0008(14) C11 0.0149(16) 0.0253(18) 0.0156(15) 0.0037(13) 0.0045(12) 0.0009(14) C1 0.0195(17) 0.0146(16) 0.0198(16) 0.0011(13) 0.0081(13) -0.0011(13) C17 0.0173(17) 0.0231(17) 0.0150(15) 0.0012(13) 0.0030(12) -0.0027(14) C12 0.0212(19) 0.0234(19) 0.0261(17) -0.0007(14) 0.0013(14) -0.0015(15) C15 0.0245(19) 0.0254(19) 0.0204(16) 0.0036(14) 0.0067(13) 0.0043(15) C16 0.0230(18) 0.0229(18) 0.0153(15) 0.0010(13) 0.0039(13) -0.0032(15) C19 0.033(2) 0.0207(19) 0.040(2) 0.0049(16) 0.0102(16) 0.0015(17) C2 0.0139(16) 0.0177(17) 0.0170(15) 0.0013(13) 0.0016(12) 0.0016(13) C3 0.0143(16) 0.0146(16) 0.0219(16) -0.0039(13) 0.0050(12) -0.0037(13) C10 0.034(2) 0.0198(18) 0.035(2) -0.0081(16) 0.0024(16) -0.0046(16) C9 0.041(2) 0.024(2) 0.035(2) -0.0005(16) 0.0117(17) -0.0128(17) C18 0.0205(18) 0.0209(18) 0.0347(19) 0.0056(15) 0.0095(14) 0.0015(15) C13 0.0215(19) 0.029(2) 0.0303(19) 0.0010(16) 0.0009(14) -0.0044(16) C20 0.029(2) 0.026(2) 0.0249(18) 0.0018(15) 0.0059(14) -0.0093(16) C5 0.0156(17) 0.0209(18) 0.0340(19) 0.0016(15) -0.0005(14) -0.0020(14) C6 0.0154(18) 0.0177(17) 0.046(2) -0.0021(16) 0.0098(15) -0.0015(14) C21 0.0183(18) 0.035(2) 0.0314(19) 0.0036(16) 0.0052(14) -0.0005(16) C14 0.0177(18) 0.037(2) 0.0198(16) 0.0063(15) 0.0057(13) 0.0058(15) C4 0.0192(17) 0.0180(17) 0.0252(17) -0.0019(14) 0.0051(13) -0.0011(14) C8 0.0296(19) 0.0174(17) 0.0214(16) -0.0045(14) 0.0095(14) -0.0105(15) C22 0.0227(19) 0.0227(18) 0.0289(18) -0.0003(15) 0.0090(14) 0.0002(15) _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 S2 C10 1.702(4) . ? S2 C7 1.728(3) . ? S1 C6 1.703(4) . ? S1 C3 1.724(3) . ? F1 C14 1.372(4) . ? F2 C20 1.370(4) . ? N1 C1 1.284(4) . ? N1 C11 1.423(4) . ? N2 C2 1.279(4) . ? N2 C17 1.413(4) . ? C7 C8 1.395(4) . ? C7 C2 1.457(4) . ? C11 C12 1.388(5) . ? C11 C16 1.393(5) . ? C1 C3 1.458(4) . ? C1 C2 1.522(4) . ? C17 C18 1.392(5) . ? C17 C22 1.399(4) . ? C12 C13 1.388(5) . ? C12 H12 0.9300 . ? C15 C14 1.378(5) . ? C15 C16 1.387(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C19 C20 1.376(5) . ? C19 C18 1.383(5) . ? C19 H19 0.9300 . ? C3 C4 1.385(4) . ? C10 C9 1.341(5) . ? C10 H10 0.9300 . ? C9 C8 1.427(5) . ? C9 H9 0.9300 . ? C18 H18 0.9300 . ? C13 C14 1.370(5) . ? C13 H13 0.9300 . ? C20 C21 1.365(5) . ? C5 C6 1.360(5) . ? C5 C4 1.417(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C21 C22 1.384(5) . ? C21 H21 0.9300 . ? C4 H4 0.9300 . ? C8 H8 0.9300 . ? C22 H22 0.9300 . ? 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 C10 S2 C7 91.26(17) . . ? C6 S1 C3 91.50(16) . . ? C1 N1 C11 120.3(3) . . ? C2 N2 C17 122.5(3) . . ? C8 C7 C2 127.4(3) . . ? C8 C7 S2 111.3(2) . . ? C2 C7 S2 121.2(2) . . ? C12 C11 C16 119.1(3) . . ? C12 C11 N1 117.6(3) . . ? C16 C11 N1 123.3(3) . . ? N1 C1 C3 120.4(3) . . ? N1 C1 C2 124.7(3) . . ? C3 C1 C2 114.9(3) . . ? C18 C17 N2 125.2(3) . . ? C18 C17 C22 118.6(3) . . ? N2 C17 C22 116.1(3) . . ? C11 C12 C13 121.1(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C15 C16 117.9(3) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C11 C16 C15 120.7(3) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C20 C19 C18 118.8(3) . . ? C20 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? N2 C2 C7 119.0(3) . . ? N2 C2 C1 125.9(3) . . ? C7 C2 C1 115.0(3) . . ? C4 C3 C1 127.4(3) . . ? C4 C3 S1 111.2(2) . . ? C1 C3 S1 121.4(2) . . ? C9 C10 S2 113.5(3) . . ? C9 C10 H10 123.3 . . ? S2 C10 H10 123.3 . . ? C10 C9 C8 112.9(3) . . ? C10 C9 H9 123.6 . . ? C8 C9 H9 123.6 . . ? C17 C18 C19 120.4(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C13 C12 117.9(3) . . ? C14 C13 H13 121.1 . . ? C12 C13 H13 121.1 . . ? C21 C20 F2 119.0(3) . . ? C21 C20 C19 122.8(3) . . ? F2 C20 C19 118.2(3) . . ? C6 C5 C4 112.3(3) . . ? C6 C5 H5 123.8 . . ? C4 C5 H5 123.8 . . ? C5 C6 S1 112.9(3) . . ? C5 C6 H6 123.6 . . ? S1 C6 H6 123.6 . . ? C20 C21 C22 118.1(3) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? C13 C14 F1 118.5(3) . . ? C13 C14 C15 123.3(3) . . ? F1 C14 C15 118.2(3) . . ? C3 C4 C5 112.1(3) . . ? C3 C4 H4 123.9 . . ? C5 C4 H4 123.9 . . ? C7 C8 C9 111.1(3) . . ? C7 C8 H8 124.4 . . ? C9 C8 H8 124.4 . . ? C21 C22 C17 121.1(3) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? 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 C10 S2 C7 C8 0.3(3) . . . . ? C10 S2 C7 C2 176.7(3) . . . . ? C1 N1 C11 C12 130.1(3) . . . . ? C1 N1 C11 C16 -52.5(4) . . . . ? C11 N1 C1 C3 179.8(3) . . . . ? C11 N1 C1 C2 0.7(5) . . . . ? C2 N2 C17 C18 -48.4(4) . . . . ? C2 N2 C17 C22 135.1(3) . . . . ? C16 C11 C12 C13 3.0(5) . . . . ? N1 C11 C12 C13 -179.4(3) . . . . ? C12 C11 C16 C15 -1.8(4) . . . . ? N1 C11 C16 C15 -179.2(3) . . . . ? C14 C15 C16 C11 -0.4(4) . . . . ? C17 N2 C2 C7 -178.7(3) . . . . ? C17 N2 C2 C1 -0.4(5) . . . . ? C8 C7 C2 N2 171.8(3) . . . . ? S2 C7 C2 N2 -3.9(4) . . . . ? C8 C7 C2 C1 -6.7(5) . . . . ? S2 C7 C2 C1 177.6(2) . . . . ? N1 C1 C2 N2 -67.5(4) . . . . ? C3 C1 C2 N2 113.4(3) . . . . ? N1 C1 C2 C7 110.9(3) . . . . ? C3 C1 C2 C7 -68.3(3) . . . . ? N1 C1 C3 C4 162.6(3) . . . . ? C2 C1 C3 C4 -18.2(5) . . . . ? N1 C1 C3 S1 -16.6(4) . . . . ? C2 C1 C3 S1 162.5(2) . . . . ? C6 S1 C3 C4 -0.2(3) . . . . ? C6 S1 C3 C1 179.1(3) . . . . ? C7 S2 C10 C9 -0.5(3) . . . . ? S2 C10 C9 C8 0.6(4) . . . . ? N2 C17 C18 C19 -179.2(3) . . . . ? C22 C17 C18 C19 -2.8(5) . . . . ? C20 C19 C18 C17 -0.4(5) . . . . ? C11 C12 C13 C14 -2.0(5) . . . . ? C18 C19 C20 C21 1.9(5) . . . . ? C18 C19 C20 F2 -179.5(3) . . . . ? C4 C5 C6 S1 0.9(4) . . . . ? C3 S1 C6 C5 -0.4(3) . . . . ? F2 C20 C21 C22 -178.8(3) . . . . ? C19 C20 C21 C22 -0.2(5) . . . . ? C12 C13 C14 F1 -179.3(3) . . . . ? C12 C13 C14 C15 -0.3(5) . . . . ? C16 C15 C14 C13 1.5(5) . . . . ? C16 C15 C14 F1 -179.5(3) . . . . ? C1 C3 C4 C5 -178.6(3) . . . . ? S1 C3 C4 C5 0.8(4) . . . . ? C6 C5 C4 C3 -1.0(4) . . . . ? C2 C7 C8 C9 -176.2(3) . . . . ? S2 C7 C8 C9 -0.1(4) . . . . ? C10 C9 C8 C7 -0.3(5) . . . . ? C20 C21 C22 C17 -3.1(5) . . . . ? C18 C17 C22 C21 4.6(5) . . . . ? N2 C17 C22 C21 -178.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.348 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.073 # Attachment 'apkv091a.cif' data_apkv091a _database_code_depnum_ccdc_archive 'CCDC 707514' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 N2 S2' _chemical_formula_sum 'C26 H24 N2 S2' _chemical_formula_weight 428.59 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' S S 0.1246 0.1234 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0969(18) _cell_length_b 9.3564(19) _cell_length_c 13.810(3) _cell_angle_alpha 81.21(3) _cell_angle_beta 86.96(3) _cell_angle_gamma 73.28(3) _cell_volume 1112.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 12267 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.255 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .992 _exptl_absorpt_correction_T_max .997 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7307 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0904 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 27.43 _reflns_number_total 4990 _reflns_number_gt 3441 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.8714P] 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 4990 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 C1 C 0.3700(3) -0.0486(3) 0.24684(19) 0.0182(6) Uani 1 1 d . . . C2 C 0.4481(3) 0.0715(3) 0.20502(18) 0.0176(6) Uani 1 1 d . . . C3 C 0.4052(3) -0.1808(3) 0.19549(19) 0.0183(6) Uani 1 1 d . . . C4 C 0.4733(3) -0.1981(3) 0.1046(2) 0.0217(6) Uani 1 1 d . . . H4 H 0.5058 -0.1235 0.0645 0.026 Uiso 1 1 calc R . . C5 C 0.4879(3) -0.3439(3) 0.0795(2) 0.0258(6) Uani 1 1 d . . . H5 H 0.5306 -0.3751 0.0209 0.031 Uiso 1 1 calc R . . C6 C 0.4323(3) -0.4321(3) 0.1508(2) 0.0269(7) Uani 1 1 d . . . H6 H 0.4339 -0.5308 0.1467 0.032 Uiso 1 1 calc R . . C7 C 0.6132(3) 0.0349(3) 0.22068(19) 0.0176(6) Uani 1 1 d . . . C8 C 0.7096(3) -0.0885(3) 0.27369(19) 0.0214(6) Uani 1 1 d . . . H8 H 0.6786 -0.1706 0.3049 0.026 Uiso 1 1 calc R . . C9 C 0.8610(3) -0.0783(3) 0.2761(2) 0.0240(6) Uani 1 1 d . . . H9 H 0.9407 -0.1529 0.3090 0.029 Uiso 1 1 calc R . . C10 C 0.8776(3) 0.0519(3) 0.2255(2) 0.0255(6) Uani 1 1 d . . . H10 H 0.9698 0.0770 0.2196 0.031 Uiso 1 1 calc R . . C11 C 0.2486(3) 0.0733(3) 0.38051(18) 0.0183(6) Uani 1 1 d . . . C12 C 0.0975(3) 0.1218(3) 0.41319(19) 0.0200(6) Uani 1 1 d . . . H12 H 0.0263 0.0757 0.3965 0.024 Uiso 1 1 calc R . . C13 C 0.0506(3) 0.2374(3) 0.47015(19) 0.0199(6) Uani 1 1 d . . . C14 C 0.1607(3) 0.3011(3) 0.49649(19) 0.0227(6) Uani 1 1 d . . . H14 H 0.1310 0.3789 0.5344 0.027 Uiso 1 1 calc R . . C15 C 0.3139(3) 0.2520(3) 0.4678(2) 0.0222(6) Uani 1 1 d . . . C16 C 0.3573(3) 0.1368(3) 0.40975(19) 0.0207(6) Uani 1 1 d . . . H16 H 0.4593 0.1021 0.3904 0.025 Uiso 1 1 calc R . . C17 C -0.1139(3) 0.2894(3) 0.5026(2) 0.0297(7) Uani 1 1 d . . . H17A H -0.1264 0.3692 0.5413 0.045 Uiso 1 1 calc R . . H17B H -0.1420 0.2067 0.5412 0.045 Uiso 1 1 calc R . . H17C H -0.1786 0.3256 0.4462 0.045 Uiso 1 1 calc R . . C18 C 0.4330(3) 0.3205(3) 0.4980(2) 0.0321(7) Uani 1 1 d . . . H18A H 0.5313 0.2721 0.4714 0.048 Uiso 1 1 calc R . . H18B H 0.4384 0.3065 0.5682 0.048 Uiso 1 1 calc R . . H18C H 0.4050 0.4263 0.4735 0.048 Uiso 1 1 calc R . . C19 C 0.2203(3) 0.2482(3) 0.1385(2) 0.0198(6) Uani 1 1 d . . . C20 C 0.1223(3) 0.3554(3) 0.1896(2) 0.0232(6) Uani 1 1 d . . . H20 H 0.1595 0.3856 0.2422 0.028 Uiso 1 1 calc R . . C21 C -0.0308(3) 0.4180(3) 0.1632(2) 0.0235(6) Uani 1 1 d . . . C22 C -0.0825(3) 0.3752(3) 0.0822(2) 0.0217(6) Uani 1 1 d . . . H22 H -0.1830 0.4207 0.0616 0.026 Uiso 1 1 calc R . . C23 C 0.0124(3) 0.2661(3) 0.0310(2) 0.0230(6) Uani 1 1 d . . . C24 C 0.1644(3) 0.2025(3) 0.0597(2) 0.0220(6) Uani 1 1 d . . . H24 H 0.2291 0.1293 0.0263 0.026 Uiso 1 1 calc R . . C25 C -0.1384(4) 0.5296(3) 0.2207(2) 0.0367(8) Uani 1 1 d . . . H25A H -0.0839 0.5463 0.2736 0.055 Uiso 1 1 calc R . . H25B H -0.2214 0.4906 0.2467 0.055 Uiso 1 1 calc R . . H25C H -0.1786 0.6232 0.1785 0.055 Uiso 1 1 calc R . . C26 C -0.0475(4) 0.2172(3) -0.0543(2) 0.0338(7) Uani 1 1 d . . . H26A H 0.0332 0.1417 -0.0806 0.051 Uiso 1 1 calc R . . H26B H -0.0829 0.3026 -0.1041 0.051 Uiso 1 1 calc R . . H26C H -0.1310 0.1763 -0.0326 0.051 Uiso 1 1 calc R . . N1 N 0.2824(2) -0.0449(2) 0.32262(16) 0.0189(5) Uani 1 1 d . . . N2 N 0.3799(2) 0.2018(2) 0.15893(16) 0.0204(5) Uani 1 1 d . . . S1 S 0.35913(9) -0.34222(7) 0.24887(5) 0.0260(2) Uani 1 1 d . . . S2 S 0.70934(8) 0.16506(7) 0.17363(6) 0.0264(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 C1 0.0134(14) 0.0174(12) 0.0236(15) -0.0009(11) -0.0040(11) -0.0042(10) C2 0.0192(14) 0.0178(13) 0.0172(14) -0.0055(10) 0.0040(11) -0.0068(11) C3 0.0152(14) 0.0174(12) 0.0231(15) -0.0021(11) -0.0016(11) -0.0063(10) C4 0.0164(14) 0.0212(13) 0.0274(16) -0.0083(11) -0.0010(12) -0.0027(11) C5 0.0215(16) 0.0298(15) 0.0272(16) -0.0119(12) 0.0013(12) -0.0049(12) C6 0.0274(17) 0.0187(13) 0.0359(18) -0.0084(12) -0.0060(13) -0.0051(12) C7 0.0171(14) 0.0184(12) 0.0191(14) -0.0034(11) 0.0027(11) -0.0078(11) C8 0.0194(15) 0.0194(13) 0.0244(15) -0.0002(11) -0.0004(12) -0.0050(11) C9 0.0183(15) 0.0274(14) 0.0229(15) -0.0002(12) -0.0063(12) -0.0016(12) C10 0.0154(15) 0.0325(15) 0.0299(16) -0.0039(13) -0.0014(12) -0.0090(12) C11 0.0222(15) 0.0169(12) 0.0165(14) -0.0011(10) 0.0011(11) -0.0075(11) C12 0.0188(15) 0.0207(13) 0.0228(15) -0.0006(11) -0.0004(11) -0.0108(11) C13 0.0207(15) 0.0184(13) 0.0176(14) 0.0018(10) 0.0038(11) -0.0036(11) C14 0.0294(17) 0.0165(12) 0.0211(15) -0.0025(11) 0.0002(12) -0.0051(11) C15 0.0260(16) 0.0191(13) 0.0225(15) -0.0005(11) -0.0032(12) -0.0089(11) C16 0.0185(15) 0.0225(13) 0.0204(14) -0.0012(11) 0.0011(11) -0.0059(11) C17 0.0271(17) 0.0234(14) 0.0366(18) -0.0033(13) 0.0054(13) -0.0057(12) C18 0.0310(18) 0.0326(16) 0.0377(18) -0.0108(14) -0.0038(14) -0.0133(13) C19 0.0158(14) 0.0136(12) 0.0286(15) 0.0046(11) 0.0002(12) -0.0058(10) C20 0.0233(16) 0.0198(13) 0.0275(16) -0.0007(11) -0.0014(12) -0.0088(12) C21 0.0227(16) 0.0160(13) 0.0309(16) 0.0004(11) 0.0022(12) -0.0062(11) C22 0.0121(14) 0.0198(13) 0.0301(16) 0.0044(11) -0.0008(12) -0.0034(11) C23 0.0234(16) 0.0226(13) 0.0236(15) 0.0024(11) 0.0004(12) -0.0104(12) C24 0.0198(15) 0.0192(13) 0.0256(15) -0.0021(11) 0.0056(12) -0.0051(11) C25 0.0278(18) 0.0331(16) 0.048(2) -0.0140(15) 0.0012(15) -0.0026(14) C26 0.0289(18) 0.0395(17) 0.0328(18) -0.0062(14) -0.0043(14) -0.0082(14) N1 0.0181(12) 0.0189(11) 0.0216(12) -0.0035(9) 0.0021(10) -0.0082(9) N2 0.0140(12) 0.0189(11) 0.0278(13) -0.0013(9) 0.0000(10) -0.0051(9) S1 0.0336(4) 0.0199(3) 0.0278(4) -0.0036(3) 0.0023(3) -0.0129(3) S2 0.0182(4) 0.0238(4) 0.0371(4) 0.0057(3) -0.0032(3) -0.0104(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 C1 N1 1.280(3) . ? C1 C3 1.467(3) . ? C1 C2 1.523(3) . ? C2 N2 1.283(3) . ? C2 C7 1.462(4) . ? C3 C4 1.382(4) . ? C3 S1 1.729(3) . ? C4 C5 1.426(3) . ? C4 H4 0.9300 . ? C5 C6 1.358(4) . ? C5 H5 0.9300 . ? C6 S1 1.707(3) . ? C6 H6 0.9300 . ? C7 C8 1.366(4) . ? C7 S2 1.726(2) . ? C8 C9 1.411(4) . ? C8 H8 0.9300 . ? C9 C10 1.352(4) . ? C9 H9 0.9300 . ? C10 S2 1.712(3) . ? C10 H10 0.9300 . ? C11 C12 1.392(4) . ? C11 C16 1.395(3) . ? C11 N1 1.416(3) . ? C12 C13 1.389(3) . ? C12 H12 0.9300 . ? C13 C14 1.392(4) . ? C13 C17 1.502(4) . ? C14 C15 1.392(4) . ? C14 H14 0.9300 . ? C15 C16 1.395(4) . ? C15 C18 1.513(4) . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.391(4) . ? C19 C24 1.397(4) . ? C19 N2 1.421(3) . ? C20 C21 1.391(4) . ? C20 H20 0.9300 . ? C21 C22 1.391(4) . ? C21 C25 1.504(4) . ? C22 C23 1.391(4) . ? C22 H22 0.9300 . ? C23 C24 1.391(4) . ? C23 C26 1.507(4) . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C3 118.9(2) . . ? N1 C1 C2 125.9(2) . . ? C3 C1 C2 115.2(2) . . ? N2 C2 C7 118.1(2) . . ? N2 C2 C1 125.1(2) . . ? C7 C2 C1 116.8(2) . . ? C4 C3 C1 128.6(2) . . ? C4 C3 S1 111.28(18) . . ? C1 C3 S1 120.1(2) . . ? C3 C4 C5 112.0(2) . . ? C3 C4 H4 124.0 . . ? C5 C4 H4 124.0 . . ? C6 C5 C4 112.5(3) . . ? C6 C5 H5 123.8 . . ? C4 C5 H5 123.8 . . ? C5 C6 S1 112.7(2) . . ? C5 C6 H6 123.6 . . ? S1 C6 H6 123.6 . . ? C8 C7 C2 129.8(2) . . ? C8 C7 S2 111.0(2) . . ? C2 C7 S2 119.12(18) . . ? C7 C8 C9 112.8(2) . . ? C7 C8 H8 123.6 . . ? C9 C8 H8 123.6 . . ? C10 C9 C8 112.6(2) . . ? C10 C9 H9 123.7 . . ? C8 C9 H9 123.7 . . ? C9 C10 S2 112.2(2) . . ? C9 C10 H10 123.9 . . ? S2 C10 H10 123.9 . . ? C12 C11 C16 119.3(2) . . ? C12 C11 N1 116.3(2) . . ? C16 C11 N1 124.4(2) . . ? C13 C12 C11 121.5(2) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C13 C14 118.0(2) . . ? C12 C13 C17 120.3(2) . . ? C14 C13 C17 121.7(2) . . ? C15 C14 C13 122.0(2) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 118.7(2) . . ? C14 C15 C18 121.6(2) . . ? C16 C15 C18 119.7(3) . . ? C11 C16 C15 120.4(3) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 119.6(2) . . ? C20 C19 N2 119.2(2) . . ? C24 C19 N2 120.7(2) . . ? C21 C20 C19 120.9(2) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C22 118.5(2) . . ? C20 C21 C25 120.9(2) . . ? C22 C21 C25 120.6(3) . . ? C23 C22 C21 121.7(2) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C24 C23 C22 118.9(2) . . ? C24 C23 C26 120.2(3) . . ? C22 C23 C26 120.8(3) . . ? C23 C24 C19 120.3(2) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C1 N1 C11 123.2(2) . . ? C2 N2 C19 122.8(2) . . ? C6 S1 C3 91.53(13) . . ? C10 S2 C7 91.39(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 -72.8(4) . . . . ? C3 C1 C2 N2 109.3(3) . . . . ? N1 C1 C2 C7 106.1(3) . . . . ? C3 C1 C2 C7 -71.8(3) . . . . ? N1 C1 C3 C4 167.7(3) . . . . ? C2 C1 C3 C4 -14.2(4) . . . . ? N1 C1 C3 S1 -11.9(3) . . . . ? C2 C1 C3 S1 166.22(18) . . . . ? C1 C3 C4 C5 -179.9(2) . . . . ? S1 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 S1 0.8(3) . . . . ? N2 C2 C7 C8 173.9(3) . . . . ? C1 C2 C7 C8 -5.1(4) . . . . ? N2 C2 C7 S2 -2.0(3) . . . . ? C1 C2 C7 S2 179.07(18) . . . . ? C2 C7 C8 C9 -176.3(2) . . . . ? S2 C7 C8 C9 -0.1(3) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 S2 0.0(3) . . . . ? C16 C11 C12 C13 3.4(4) . . . . ? N1 C11 C12 C13 -179.7(2) . . . . ? C11 C12 C13 C14 -1.9(4) . . . . ? C11 C12 C13 C17 178.8(2) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C17 C13 C14 C15 179.1(2) . . . . ? C13 C14 C15 C16 0.9(4) . . . . ? C13 C14 C15 C18 -179.1(2) . . . . ? C12 C11 C16 C15 -2.6(4) . . . . ? N1 C11 C16 C15 -179.3(2) . . . . ? C14 C15 C16 C11 0.5(4) . . . . ? C18 C15 C16 C11 -179.4(2) . . . . ? C24 C19 C20 C21 -0.1(4) . . . . ? N2 C19 C20 C21 171.6(2) . . . . ? C19 C20 C21 C22 -2.4(4) . . . . ? C19 C20 C21 C25 177.7(2) . . . . ? C20 C21 C22 C23 3.7(4) . . . . ? C25 C21 C22 C23 -176.4(2) . . . . ? C21 C22 C23 C24 -2.4(4) . . . . ? C21 C22 C23 C26 177.7(2) . . . . ? C22 C23 C24 C19 -0.2(4) . . . . ? C26 C23 C24 C19 179.7(2) . . . . ? C20 C19 C24 C23 1.4(4) . . . . ? N2 C19 C24 C23 -170.2(2) . . . . ? C3 C1 N1 C11 176.3(2) . . . . ? C2 C1 N1 C11 -1.6(4) . . . . ? C12 C11 N1 C1 139.3(3) . . . . ? C16 C11 N1 C1 -43.9(4) . . . . ? C7 C2 N2 C19 179.1(2) . . . . ? C1 C2 N2 C19 -2.0(4) . . . . ? C20 C19 N2 C2 108.0(3) . . . . ? C24 C19 N2 C2 -80.3(3) . . . . ? C5 C6 S1 C3 -0.8(2) . . . . ? C4 C3 S1 C6 0.6(2) . . . . ? C1 C3 S1 C6 -179.8(2) . . . . ? C9 C10 S2 C7 0.0(2) . . . . ? C8 C7 S2 C10 0.1(2) . . . . ? C2 C7 S2 C10 176.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.479 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.071 # Attachment 'apkv098a.cif' data_apkv098a _database_code_depnum_ccdc_archive 'CCDC 707515' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H32 N2 S2' _chemical_formula_sum 'C30 H32 N2 S2' _chemical_formula_weight 484.70 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7281(19) _cell_length_b 12.001(2) _cell_length_c 12.295(3) _cell_angle_alpha 110.01(3) _cell_angle_beta 98.25(3) _cell_angle_gamma 96.87(3) _cell_volume 1312.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8618 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.979 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8618 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0874 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5933 _reflns_number_gt 3845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+0.0355P] 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 5933 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 0.966 _refine_ls_restrained_S_all 0.966 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 C1 C 0.6709(2) 0.36017(17) 0.15069(15) 0.0185(4) Uani 1 1 d . . . C2 C 0.8204(2) 0.34724(16) 0.13487(16) 0.0186(4) Uani 1 1 d . . . C3 C 0.5812(2) 0.25465(18) 0.15497(16) 0.0233(5) Uani 1 1 d . . . C4 C 0.6122(3) 0.14280(18) 0.13954(17) 0.0309(6) Uani 1 1 d . . . H4 H 0.6977 0.1208 0.1234 0.037 Uiso 1 1 calc R . . C5 C 0.4992(4) 0.0642(2) 0.1509(2) 0.0508(8) Uani 1 1 d . . . H5 H 0.5021 -0.0153 0.1432 0.061 Uiso 1 1 calc R . . C6 C 0.3866(4) 0.1175(3) 0.1741(2) 0.0569(9) Uani 1 1 d . . . H6 H 0.3031 0.0787 0.1836 0.068 Uiso 1 1 calc R . . C7 C 0.9167(2) 0.34609(16) 0.23679(16) 0.0209(5) Uani 1 1 d . . . C8 C 0.8928(2) 0.36124(18) 0.34795(17) 0.0257(5) Uani 1 1 d . . . H8 H 0.8076 0.3754 0.3710 0.031 Uiso 1 1 calc R . . C9 C 1.0117(3) 0.35296(19) 0.42329(19) 0.0334(6) Uani 1 1 d . . . H9 H 1.0134 0.3612 0.5015 0.040 Uiso 1 1 calc R . . C10 C 1.1225(3) 0.3319(2) 0.3700(2) 0.0368(6) Uani 1 1 d . . . H10 H 1.2089 0.3236 0.4070 0.044 Uiso 1 1 calc R . . C11 C 0.7099(2) 0.56330(17) 0.17194(17) 0.0215(5) Uani 1 1 d . . . C12 C 0.6997(3) 0.60777(19) 0.08181(17) 0.0302(5) Uani 1 1 d . . . H12 H 0.6399 0.5634 0.0096 0.036 Uiso 1 1 calc R . . C13 C 0.7788(3) 0.71875(19) 0.09946(18) 0.0312(6) Uani 1 1 d . . . H13 H 0.7720 0.7464 0.0372 0.037 Uiso 1 1 calc R . . C14 C 0.8681(2) 0.79063(17) 0.20629(17) 0.0235(5) Uani 1 1 d . . . C15 C 0.8767(3) 0.74292(19) 0.29500(17) 0.0291(5) Uani 1 1 d . . . H15 H 0.9358 0.7870 0.3676 0.035 Uiso 1 1 calc R . . C16 C 0.7998(2) 0.63195(19) 0.27817(17) 0.0292(5) Uani 1 1 d . . . H16 H 0.8085 0.6028 0.3394 0.035 Uiso 1 1 calc R . . C17 C 0.9433(3) 0.91789(18) 0.22993(18) 0.0288(5) Uani 1 1 d . . . C18 C 0.8619(3) 1.0067(2) 0.3058(2) 0.0461(7) Uani 1 1 d . . . H18A H 0.7657 0.9914 0.2653 0.069 Uiso 1 1 calc R . . H18B H 0.9050 1.0878 0.3195 0.069 Uiso 1 1 calc R . . H18C H 0.8644 0.9962 0.3800 0.069 Uiso 1 1 calc R . . C19 C 1.0965(3) 0.9424(2) 0.2978(2) 0.0411(6) Uani 1 1 d . . . H19A H 1.0962 0.9336 0.3725 0.062 Uiso 1 1 calc R . . H19B H 1.1408 1.0229 0.3107 0.062 Uiso 1 1 calc R . . H19C H 1.1478 0.8859 0.2526 0.062 Uiso 1 1 calc R . . C20 C 0.9493(3) 0.9419(2) 0.1158(2) 0.0504(8) Uani 1 1 d . . . H20A H 0.9934 0.8826 0.0654 0.076 Uiso 1 1 calc R . . H20B H 1.0030 1.0208 0.1345 0.076 Uiso 1 1 calc R . . H20C H 0.8551 0.9372 0.0760 0.076 Uiso 1 1 calc R . . C21 C 0.7841(2) 0.32604(17) -0.06826(16) 0.0201(5) Uani 1 1 d . . . C22 C 0.6486(2) 0.25913(18) -0.11313(16) 0.0261(5) Uani 1 1 d . . . H22 H 0.6033 0.2258 -0.0668 0.031 Uiso 1 1 calc R . . C23 C 0.5794(2) 0.24128(18) -0.22666(17) 0.0269(5) Uani 1 1 d . . . H23 H 0.4885 0.1960 -0.2549 0.032 Uiso 1 1 calc R . . C24 C 0.6432(2) 0.28975(17) -0.29864(16) 0.0219(5) Uani 1 1 d . . . C25 C 0.7785(2) 0.36016(18) -0.25068(17) 0.0272(5) Uani 1 1 d . . . H25 H 0.8222 0.3970 -0.2953 0.033 Uiso 1 1 calc R . . C26 C 0.8486(2) 0.37627(18) -0.13884(16) 0.0257(5) Uani 1 1 d . . . H26 H 0.9396 0.4211 -0.1106 0.031 Uiso 1 1 calc R . . C27 C 0.5740(3) 0.26683(18) -0.42657(17) 0.0264(5) Uani 1 1 d . . . C28 C 0.6691(3) 0.2050(2) -0.50832(18) 0.0384(6) Uani 1 1 d . . . H28A H 0.7607 0.2554 -0.4867 0.058 Uiso 1 1 calc R . . H28B H 0.6281 0.1919 -0.5885 0.058 Uiso 1 1 calc R . . H28C H 0.6784 0.1290 -0.5011 0.058 Uiso 1 1 calc R . . C29 C 0.4296(3) 0.1842(2) -0.46523(19) 0.0377(6) Uani 1 1 d . . . H29A H 0.4396 0.1084 -0.4579 0.056 Uiso 1 1 calc R . . H29B H 0.3916 0.1712 -0.5460 0.056 Uiso 1 1 calc R . . H29C H 0.3669 0.2213 -0.4161 0.056 Uiso 1 1 calc R . . C30 C 0.5558(3) 0.3878(2) -0.4388(2) 0.0467(7) Uani 1 1 d . . . H30A H 0.5002 0.4278 -0.3841 0.070 Uiso 1 1 calc R . . H30B H 0.5090 0.3734 -0.5179 0.070 Uiso 1 1 calc R . . H30C H 0.6469 0.4376 -0.4222 0.070 Uiso 1 1 calc R . . N1 N 0.61999(19) 0.45590(15) 0.16211(13) 0.0231(4) Uani 1 1 d . . . N2 N 0.86872(19) 0.33694(14) 0.04045(13) 0.0213(4) Uani 1 1 d . . . S1 S 1.08621(6) 0.32220(5) 0.22591(5) 0.03333(18) Uani 1 1 d . . . S2 S 0.41443(7) 0.26405(6) 0.18409(5) 0.0435(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 C1 0.0169(11) 0.0233(10) 0.0146(9) 0.0072(8) 0.0016(8) 0.0016(9) C2 0.0183(12) 0.0144(9) 0.0226(10) 0.0064(8) 0.0037(8) 0.0018(8) C3 0.0200(12) 0.0301(11) 0.0170(9) 0.0091(8) 0.0012(8) -0.0047(9) C4 0.0374(15) 0.0253(12) 0.0279(11) 0.0126(9) 0.0018(10) -0.0058(10) C5 0.073(2) 0.0345(14) 0.0324(13) 0.0164(11) -0.0061(14) -0.0286(15) C6 0.051(2) 0.072(2) 0.0355(14) 0.0257(14) -0.0044(13) -0.0376(17) C7 0.0185(12) 0.0152(10) 0.0260(10) 0.0060(8) 0.0000(9) 0.0019(8) C8 0.0247(13) 0.0241(11) 0.0268(11) 0.0105(9) 0.0000(9) 0.0015(9) C9 0.0366(16) 0.0305(12) 0.0274(11) 0.0130(10) -0.0109(10) -0.0017(11) C10 0.0267(15) 0.0309(12) 0.0478(14) 0.0172(11) -0.0141(12) 0.0029(10) C11 0.0180(12) 0.0191(10) 0.0280(10) 0.0078(9) 0.0051(9) 0.0078(9) C12 0.0345(15) 0.0295(12) 0.0224(10) 0.0088(9) -0.0020(10) 0.0017(10) C13 0.0389(16) 0.0301(12) 0.0274(11) 0.0155(10) 0.0032(10) 0.0058(11) C14 0.0261(13) 0.0208(10) 0.0261(10) 0.0089(9) 0.0076(9) 0.0092(9) C15 0.0331(15) 0.0254(11) 0.0240(10) 0.0077(9) -0.0016(9) 0.0004(10) C16 0.0318(15) 0.0295(12) 0.0284(11) 0.0164(10) -0.0002(10) 0.0033(10) C17 0.0347(15) 0.0221(11) 0.0313(11) 0.0109(9) 0.0087(10) 0.0056(10) C18 0.0528(19) 0.0236(12) 0.0629(16) 0.0115(11) 0.0214(14) 0.0111(12) C19 0.0382(17) 0.0316(13) 0.0513(14) 0.0165(11) 0.0051(12) -0.0019(11) C20 0.071(2) 0.0350(14) 0.0439(14) 0.0197(12) 0.0093(14) -0.0071(14) C21 0.0205(12) 0.0205(10) 0.0193(9) 0.0060(8) 0.0061(8) 0.0047(9) C22 0.0305(14) 0.0248(11) 0.0212(10) 0.0085(9) 0.0077(9) -0.0052(9) C23 0.0219(13) 0.0303(12) 0.0231(10) 0.0059(9) 0.0040(9) -0.0028(9) C24 0.0243(13) 0.0193(10) 0.0215(10) 0.0063(8) 0.0050(9) 0.0051(9) C25 0.0306(14) 0.0275(11) 0.0262(11) 0.0138(9) 0.0082(10) 0.0011(10) C26 0.0208(13) 0.0264(11) 0.0260(10) 0.0072(9) 0.0053(9) -0.0044(9) C27 0.0305(14) 0.0262(11) 0.0229(10) 0.0105(9) 0.0027(9) 0.0049(10) C28 0.0389(16) 0.0520(15) 0.0226(11) 0.0115(11) 0.0067(10) 0.0085(12) C29 0.0349(16) 0.0444(14) 0.0281(12) 0.0108(11) -0.0006(10) 0.0017(12) C30 0.061(2) 0.0381(14) 0.0421(13) 0.0227(12) -0.0053(13) 0.0083(13) N1 0.0200(10) 0.0258(9) 0.0225(8) 0.0085(7) 0.0016(7) 0.0047(8) N2 0.0212(10) 0.0190(8) 0.0224(8) 0.0068(7) 0.0043(7) 0.0009(7) S1 0.0200(3) 0.0363(3) 0.0423(3) 0.0135(3) 0.0013(3) 0.0082(3) S2 0.0209(4) 0.0688(5) 0.0404(3) 0.0237(3) 0.0071(3) -0.0058(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 C1 N1 1.277(3) . ? C1 C3 1.471(3) . ? C1 C2 1.514(3) . ? C2 N2 1.287(2) . ? C2 C7 1.458(3) . ? C3 C4 1.367(3) . ? C3 S2 1.719(2) . ? C4 C5 1.416(3) . ? C4 H4 0.9300 . ? C5 C6 1.350(4) . ? C5 H5 0.9300 . ? C6 S2 1.705(3) . ? C6 H6 0.9300 . ? C7 C8 1.373(3) . ? C7 S1 1.724(2) . ? C8 C9 1.411(3) . ? C8 H8 0.9300 . ? C9 C10 1.345(4) . ? C9 H9 0.9300 . ? C10 S1 1.716(2) . ? C10 H10 0.9300 . ? C11 C16 1.383(3) . ? C11 C12 1.381(3) . ? C11 N1 1.426(3) . ? C12 C13 1.387(3) . ? C12 H12 0.9300 . ? C13 C14 1.393(3) . ? C13 H13 0.9300 . ? C14 C15 1.392(3) . ? C14 C17 1.523(3) . ? C15 C16 1.380(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C20 1.534(3) . ? C17 C18 1.538(3) . ? C17 C19 1.540(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C22 1.387(3) . ? C21 C26 1.390(3) . ? C21 N2 1.421(2) . ? C22 C23 1.392(3) . ? C22 H22 0.9300 . ? C23 C24 1.389(3) . ? C23 H23 0.9300 . ? C24 C25 1.402(3) . ? C24 C27 1.536(3) . ? C25 C26 1.382(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.529(3) . ? C27 C29 1.528(3) . ? C27 C30 1.538(3) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C3 118.93(19) . . ? N1 C1 C2 124.49(18) . . ? C3 C1 C2 116.57(17) . . ? N2 C2 C7 117.96(19) . . ? N2 C2 C1 125.96(17) . . ? C7 C2 C1 116.07(16) . . ? C4 C3 C1 128.4(2) . . ? C4 C3 S2 111.50(17) . . ? C1 C3 S2 120.11(17) . . ? C3 C4 C5 112.3(3) . . ? C3 C4 H4 123.9 . . ? C5 C4 H4 123.9 . . ? C6 C5 C4 112.4(2) . . ? C6 C5 H5 123.8 . . ? C4 C5 H5 123.8 . . ? C5 C6 S2 112.6(2) . . ? C5 C6 H6 123.7 . . ? S2 C6 H6 123.7 . . ? C8 C7 C2 128.9(2) . . ? C8 C7 S1 110.98(16) . . ? C2 C7 S1 120.07(15) . . ? C7 C8 C9 112.6(2) . . ? C7 C8 H8 123.7 . . ? C9 C8 H8 123.7 . . ? C10 C9 C8 112.8(2) . . ? C10 C9 H9 123.6 . . ? C8 C9 H9 123.6 . . ? C9 C10 S1 112.29(18) . . ? C9 C10 H10 123.9 . . ? S1 C10 H10 123.9 . . ? C16 C11 C12 118.42(19) . . ? C16 C11 N1 119.59(18) . . ? C12 C11 N1 121.65(18) . . ? C11 C12 C13 119.78(19) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 122.92(19) . . ? C12 C13 H13 118.5 . . ? C14 C13 H13 118.5 . . ? C15 C14 C13 115.85(19) . . ? C15 C14 C17 121.03(18) . . ? C13 C14 C17 122.94(18) . . ? C16 C15 C14 121.82(19) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C11 121.20(19) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C14 C17 C20 112.34(18) . . ? C14 C17 C18 107.69(19) . . ? C20 C17 C18 109.2(2) . . ? C14 C17 C19 111.72(19) . . ? C20 C17 C19 107.3(2) . . ? C18 C17 C19 108.5(2) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 118.36(18) . . ? C22 C21 N2 124.56(18) . . ? C26 C21 N2 116.74(19) . . ? C21 C22 C23 120.85(19) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 121.4(2) . . ? C24 C23 H23 119.3 . . ? C22 C23 H23 119.3 . . ? C23 C24 C25 117.05(19) . . ? C23 C24 C27 123.13(19) . . ? C25 C24 C27 119.80(18) . . ? C26 C25 C24 121.71(19) . . ? C26 C25 H25 119.1 . . ? C24 C25 H25 119.1 . . ? C25 C26 C21 120.6(2) . . ? C25 C26 H26 119.7 . . ? C21 C26 H26 119.7 . . ? C28 C27 C29 107.52(18) . . ? C28 C27 C24 108.65(19) . . ? C29 C27 C24 112.50(18) . . ? C28 C27 C30 110.1(2) . . ? C29 C27 C30 108.7(2) . . ? C24 C27 C30 109.31(17) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C1 N1 C11 119.69(18) . . ? C2 N2 C21 123.94(18) . . ? C10 S1 C7 91.32(12) . . ? C6 S2 C3 91.26(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 N1 C1 C2 N2 -73.7(3) . . . . ? C3 C1 C2 N2 107.4(2) . . . . ? N1 C1 C2 C7 106.5(2) . . . . ? C3 C1 C2 C7 -72.4(2) . . . . ? N1 C1 C3 C4 176.78(19) . . . . ? C2 C1 C3 C4 -4.3(3) . . . . ? N1 C1 C3 S2 -4.0(2) . . . . ? C2 C1 C3 S2 174.96(12) . . . . ? C1 C3 C4 C5 179.60(18) . . . . ? S2 C3 C4 C5 0.3(2) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 S2 -0.5(3) . . . . ? N2 C2 C7 C8 176.58(19) . . . . ? C1 C2 C7 C8 -3.7(3) . . . . ? N2 C2 C7 S1 -3.9(2) . . . . ? C1 C2 C7 S1 175.87(13) . . . . ? C2 C7 C8 C9 179.34(18) . . . . ? S1 C7 C8 C9 -0.2(2) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C8 C9 C10 S1 0.3(2) . . . . ? C16 C11 C12 C13 0.1(3) . . . . ? N1 C11 C12 C13 173.4(2) . . . . ? C11 C12 C13 C14 -1.3(4) . . . . ? C12 C13 C14 C15 1.7(3) . . . . ? C12 C13 C14 C17 -173.5(2) . . . . ? C13 C14 C15 C16 -0.8(3) . . . . ? C17 C14 C15 C16 174.4(2) . . . . ? C14 C15 C16 C11 -0.3(4) . . . . ? C12 C11 C16 C15 0.7(3) . . . . ? N1 C11 C16 C15 -172.7(2) . . . . ? C15 C14 C17 C20 166.7(2) . . . . ? C13 C14 C17 C20 -18.4(3) . . . . ? C15 C14 C17 C18 -73.0(3) . . . . ? C13 C14 C17 C18 101.9(2) . . . . ? C15 C14 C17 C19 46.0(3) . . . . ? C13 C14 C17 C19 -139.1(2) . . . . ? C26 C21 C22 C23 0.9(3) . . . . ? N2 C21 C22 C23 -172.20(18) . . . . ? C21 C22 C23 C24 -0.1(3) . . . . ? C22 C23 C24 C25 -1.8(3) . . . . ? C22 C23 C24 C27 176.67(19) . . . . ? C23 C24 C25 C26 3.0(3) . . . . ? C27 C24 C25 C26 -175.51(19) . . . . ? C24 C25 C26 C21 -2.3(3) . . . . ? C22 C21 C26 C25 0.3(3) . . . . ? N2 C21 C26 C25 173.93(17) . . . . ? C23 C24 C27 C28 -119.7(2) . . . . ? C25 C24 C27 C28 58.7(2) . . . . ? C23 C24 C27 C29 -0.7(3) . . . . ? C25 C24 C27 C29 177.7(2) . . . . ? C23 C24 C27 C30 120.1(2) . . . . ? C25 C24 C27 C30 -61.5(3) . . . . ? C3 C1 N1 C11 172.75(15) . . . . ? C2 C1 N1 C11 -6.1(3) . . . . ? C16 C11 N1 C1 -77.7(2) . . . . ? C12 C11 N1 C1 109.1(2) . . . . ? C7 C2 N2 C21 174.26(16) . . . . ? C1 C2 N2 C21 -5.5(3) . . . . ? C22 C21 N2 C2 -39.3(3) . . . . ? C26 C21 N2 C2 147.58(19) . . . . ? C9 C10 S1 C7 -0.36(18) . . . . ? C8 C7 S1 C10 0.32(16) . . . . ? C2 C7 S1 C10 -179.28(16) . . . . ? C5 C6 S2 C3 0.6(2) . . . . ? C4 C3 S2 C6 -0.51(16) . . . . ? C1 C3 S2 C6 -179.86(16) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.324 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.059 # Attachment 'apkv100a.CIF' data_apkv100 _database_code_depnum_ccdc_archive 'CCDC 707516' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H32 I3 N2 P S2' _chemical_formula_sum 'C30 H32 I3 N2 P S2' _chemical_formula_weight 896.37 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall p2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.682(2) _cell_length_b 16.724(3) _cell_length_c 17.083(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3337.4(11) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4069 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description Rod _exptl_crystal_colour Red _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 3.005 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.777 _exptl_absorpt_correction_T_max 0.835 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7608 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7608 _reflns_number_gt 6444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The thiophene rings were disordered. The disorder was modeled by assigning the variable x to the site occupancy factor for the atoms of one orientation and (1-x) to the site occupancy factor to the atoms of the alternate orientation. A common isotropic displacement parameter was refined for the atoms of both orientations. The geometry of the two different orientations were restrained throughout the refinement. The site occupancy factor for the major component of the ring composed of atoms C3, C4, C5, C6 and S1 refined to 94(2)%. The site occupancy factor for the major component of the ring composed of atoms C7, C8, C9, C10 and S2 refined to 90(2)%. The absolute structure was determined by the method of Flack (1983). ; _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^)+(0.0305P)^2^+3.4126P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(3) _refine_ls_number_reflns 7608 _refine_ls_number_parameters 377 _refine_ls_number_restraints 270 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.370 _refine_ls_shift/su_max 0.003 _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 C1 C 0.8204(4) 0.8791(3) 0.4879(3) 0.0222(14) Uani 1 1 d D A . C2 C 0.8016(4) 0.8510(3) 0.5619(3) 0.0214(13) Uani 1 1 d D A . C11 C 0.9314(5) 0.8420(4) 0.3677(4) 0.0205(14) Uani 1 1 d . . . C12 C 0.8737(5) 0.8045(4) 0.3087(4) 0.0239(14) Uani 1 1 d . . . H12 H 0.8058 0.7755 0.3201 0.029 Uiso 1 1 calc R . . C13 C 0.9128(5) 0.8082(4) 0.2332(4) 0.0254(14) Uani 1 1 d . . . H13 H 0.8711 0.7818 0.1930 0.031 Uiso 1 1 calc R . . C14 C 1.0118(5) 0.8497(4) 0.2140(4) 0.0228(14) Uani 1 1 d . . . C15 C 1.0693(5) 0.8882(4) 0.2740(4) 0.0216(13) Uani 1 1 d . . . H15 H 1.1364 0.9180 0.2622 0.026 Uiso 1 1 calc R . . C16 C 1.0314(5) 0.8843(4) 0.3514(4) 0.0219(14) Uani 1 1 d . . . H16 H 1.0728 0.9100 0.3921 0.026 Uiso 1 1 calc R . . C17 C 1.0578(5) 0.8510(4) 0.1291(4) 0.0257(15) Uani 1 1 d . . . C18 C 0.8931(5) 0.7479(4) 0.6524(4) 0.0205(13) Uani 1 1 d . . . C19 C 0.9383(5) 0.7939(4) 0.7113(4) 0.0259(15) Uani 1 1 d . . . H19 H 0.9472 0.8499 0.7041 0.031 Uiso 1 1 calc R . . C20 C 0.9704(5) 0.7593(4) 0.7804(4) 0.0225(13) Uani 1 1 d . . . H20 H 1.0000 0.7920 0.8211 0.027 Uiso 1 1 calc R . . C21 C 0.9604(5) 0.6753(4) 0.7928(4) 0.0208(14) Uani 1 1 d . . . C22 C 0.9121(5) 0.6311(3) 0.7330(4) 0.0214(13) Uani 1 1 d . . . H22 H 0.9016 0.5753 0.7401 0.026 Uiso 1 1 calc R . . C23 C 0.8783(5) 0.6658(4) 0.6626(4) 0.0237(14) Uani 1 1 d . . . H23 H 0.8458 0.6340 0.6222 0.028 Uiso 1 1 calc R . . C24 C 1.0074(5) 0.6405(4) 0.8692(4) 0.0267(15) Uani 1 1 d . . . C25 C 0.9578(6) 0.8579(5) 0.0703(4) 0.0384(17) Uani 1 1 d . . . H25A H 0.9881 0.8585 0.0169 0.058 Uiso 1 1 calc R . . H25B H 0.9154 0.9074 0.0802 0.058 Uiso 1 1 calc R . . H25C H 0.9064 0.8120 0.0767 0.058 Uiso 1 1 calc R . . C26 C 1.1404(7) 0.9205(5) 0.1153(4) 0.044(2) Uani 1 1 d . . . H26A H 1.1043 0.9706 0.1319 0.067 Uiso 1 1 calc R . . H26B H 1.1593 0.9236 0.0595 0.067 Uiso 1 1 calc R . . H26C H 1.2106 0.9118 0.1456 0.067 Uiso 1 1 calc R . . C27 C 1.1209(7) 0.7711(4) 0.1151(5) 0.0385(18) Uani 1 1 d . . . H27A H 1.1870 0.7676 0.1502 0.058 Uiso 1 1 calc R . . H27B H 1.1469 0.7685 0.0607 0.058 Uiso 1 1 calc R . . H27C H 1.0687 0.7265 0.1256 0.058 Uiso 1 1 calc R . . C28 C 0.9455(6) 0.6767(5) 0.9406(5) 0.0423(19) Uani 1 1 d . . . H28A H 0.8647 0.6610 0.9396 0.063 Uiso 1 1 calc R . . H28B H 0.9513 0.7352 0.9387 0.063 Uiso 1 1 calc R . . H28C H 0.9811 0.6571 0.9888 0.063 Uiso 1 1 calc R . . C29 C 1.1342(6) 0.6594(4) 0.8741(5) 0.0342(17) Uani 1 1 d . . . H29A H 1.1451 0.7175 0.8748 0.051 Uiso 1 1 calc R . . H29B H 1.1735 0.6367 0.8285 0.051 Uiso 1 1 calc R . . H29C H 1.1660 0.6361 0.9221 0.051 Uiso 1 1 calc R . . C30 C 0.9922(6) 0.5492(4) 0.8723(5) 0.0366(18) Uani 1 1 d . . . H30A H 1.0309 0.5248 0.8274 0.055 Uiso 1 1 calc R . . H30B H 0.9104 0.5361 0.8705 0.055 Uiso 1 1 calc R . . H30C H 1.0254 0.5285 0.9209 0.055 Uiso 1 1 calc R . . N1 N 0.8978(4) 0.8313(3) 0.4481(3) 0.0221(11) Uani 1 1 d . . . N2 N 0.8721(4) 0.7828(3) 0.5759(3) 0.0204(11) Uani 1 1 d . . . P1 P 0.95455(15) 0.75735(10) 0.50043(11) 0.0279(4) Uani 1 1 d . . . C6 C 0.7510(3) 0.9372(2) 0.4504(2) 0.0224(13) Uani 1 1 d D . . S1 S 0.60718(18) 0.93520(14) 0.43665(18) 0.0582(6) Uani 0.94 1 d PDU A 1 C3 C 0.6060(5) 1.0242(3) 0.3898(3) 0.0480(14) Uani 0.94 1 d PDU A 1 H3 H 0.5378 1.0479 0.3704 0.058 Uiso 0.94 1 calc PR A 1 C4 C 0.7057(6) 1.0573(3) 0.3824(4) 0.0435(13) Uani 0.94 1 d PDU A 1 H4 H 0.7177 1.1072 0.3571 0.052 Uiso 0.94 1 calc PR A 1 C5 C 0.7988(5) 1.0094(3) 0.4175(3) 0.0379(15) Uani 0.94 1 d PDU A 1 H5 H 0.8775 1.0239 0.4183 0.045 Uiso 0.94 1 calc PR A 1 S1A S 0.7672(13) 1.0273(10) 0.414(2) 0.054 Uiso 0.06 1 d PDU A 2 C3A C 0.6192(15) 1.0278(5) 0.3882(7) 0.054 Uiso 0.06 1 d PDU A 2 H3A H 0.5846 1.0724 0.3631 0.065 Uiso 0.06 1 calc PR A 2 C4A C 0.5641(12) 0.9669(14) 0.405(3) 0.054 Uiso 0.06 1 d PDU A 2 H4A H 0.4850 0.9616 0.3933 0.065 Uiso 0.06 1 calc PR A 2 C5A C 0.6259(11) 0.9073(13) 0.442(3) 0.054 Uiso 0.06 1 d PDU A 2 H5A H 0.5970 0.8571 0.4587 0.065 Uiso 0.06 1 calc PR A 2 C10 C 0.7225(3) 0.8742(3) 0.6203(2) 0.0269(11) Uani 1 1 d DU . . S2 S 0.62560(18) 0.81730(12) 0.66922(13) 0.0389(5) Uani 0.90 1 d PDU B 1 C7 C 0.5757(4) 0.8943(3) 0.7228(3) 0.0377(13) Uani 0.90 1 d PDU B 1 H7 H 0.5164 0.8889 0.7605 0.045 Uiso 0.90 1 calc PR B 1 C8 C 0.6263(5) 0.9618(4) 0.7076(4) 0.0353(13) Uani 0.90 1 d PDU B 1 H8 H 0.6076 1.0105 0.7333 0.042 Uiso 0.90 1 calc PR B 1 C9 C 0.7146(4) 0.9558(3) 0.6473(3) 0.0255(13) Uani 0.90 1 d PDU B 1 H9 H 0.7599 0.9990 0.6287 0.031 Uiso 0.90 1 calc PR B 1 S2A S 0.6864(14) 0.9596(5) 0.6628(10) 0.038 Uiso 0.10 1 d PDU B 2 C7A C 0.5843(11) 0.9047(7) 0.7201(7) 0.038 Uiso 0.10 1 d PDU B 2 H7A H 0.5366 0.9304 0.7574 0.046 Uiso 0.10 1 calc PR B 2 C8A C 0.5789(17) 0.8322(8) 0.7086(12) 0.038 Uiso 0.10 1 d PDU B 2 H8A H 0.5274 0.7986 0.7364 0.046 Uiso 0.10 1 calc PR B 2 C9A C 0.6535(18) 0.8030(6) 0.6521(13) 0.038 Uiso 0.10 1 d PDU B 2 H9A H 0.6605 0.7489 0.6360 0.046 Uiso 0.10 1 calc PR B 2 I1 I 1.19795(4) 0.85659(3) 0.55713(3) 0.04433(15) Uani 1 1 d . . . I2 I 1.22829(3) 0.89558(2) 0.72768(3) 0.02605(10) Uani 1 1 d . . . I3 I 1.25601(5) 0.92969(3) 0.88951(3) 0.04704(15) 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 C1 0.024(3) 0.025(3) 0.018(3) 0.006(3) -0.001(3) -0.003(2) C2 0.018(3) 0.019(3) 0.028(4) 0.004(3) 0.003(3) -0.004(2) C11 0.029(3) 0.019(3) 0.013(3) 0.004(3) 0.001(3) 0.003(3) C12 0.020(3) 0.025(3) 0.027(4) -0.003(3) 0.000(3) -0.007(3) C13 0.026(3) 0.025(3) 0.025(4) -0.002(3) -0.006(3) -0.011(3) C14 0.025(3) 0.021(3) 0.023(4) 0.003(3) -0.001(3) 0.004(3) C15 0.026(3) 0.027(3) 0.012(3) 0.005(3) 0.002(3) -0.001(3) C16 0.027(3) 0.024(3) 0.015(3) 0.001(3) -0.003(2) 0.000(3) C17 0.028(3) 0.033(4) 0.016(4) -0.008(3) 0.004(3) -0.001(3) C18 0.029(3) 0.021(3) 0.012(3) 0.002(3) 0.003(3) 0.002(3) C19 0.032(3) 0.016(3) 0.030(4) 0.002(3) 0.001(3) -0.004(3) C20 0.028(3) 0.024(3) 0.015(4) -0.005(3) -0.001(3) -0.002(2) C21 0.021(3) 0.025(3) 0.016(4) 0.003(3) 0.000(2) 0.001(2) C22 0.026(3) 0.015(3) 0.023(4) 0.008(3) -0.002(3) -0.002(2) C23 0.030(3) 0.022(3) 0.019(4) -0.005(3) 0.000(3) -0.003(3) C24 0.028(3) 0.025(3) 0.027(4) 0.009(3) -0.005(3) -0.004(3) C25 0.042(4) 0.048(4) 0.025(4) -0.002(4) 0.000(3) 0.008(4) C26 0.060(5) 0.056(5) 0.017(4) -0.003(4) 0.013(4) -0.011(4) C27 0.048(4) 0.042(4) 0.025(4) -0.003(3) 0.006(4) 0.007(3) C28 0.050(4) 0.055(5) 0.023(4) 0.005(4) -0.005(4) -0.007(4) C29 0.032(4) 0.032(4) 0.039(5) 0.013(3) -0.011(3) 0.000(3) C30 0.044(4) 0.036(4) 0.030(5) 0.013(3) -0.017(3) -0.011(3) N1 0.026(3) 0.026(3) 0.014(3) 0.000(2) 0.002(2) 0.001(2) N2 0.030(3) 0.021(3) 0.010(3) 0.002(2) 0.001(2) 0.000(2) P1 0.0397(10) 0.0258(9) 0.0181(9) 0.0040(7) 0.0044(8) 0.0108(8) C6 0.029(3) 0.023(3) 0.015(3) 0.001(2) 0.002(3) -0.002(3) S1 0.0421(11) 0.0541(12) 0.0783(16) 0.0241(13) -0.0189(11) -0.0040(10) C3 0.045(2) 0.046(2) 0.053(3) 0.010(2) -0.007(2) 0.006(2) C4 0.045(2) 0.040(2) 0.046(3) 0.010(2) 0.001(2) 0.006(2) C5 0.033(3) 0.036(3) 0.045(3) 0.013(3) 0.002(3) 0.022(2) C10 0.025(2) 0.028(2) 0.027(2) 0.0041(19) -0.001(2) -0.0020(19) S2 0.0406(10) 0.0406(10) 0.0354(11) -0.0053(9) 0.0153(9) -0.0153(9) C7 0.034(2) 0.046(2) 0.033(2) 0.001(2) 0.006(2) 0.001(2) C8 0.037(2) 0.037(2) 0.032(2) -0.001(2) 0.009(2) 0.006(2) C9 0.023(2) 0.029(2) 0.024(3) 0.005(2) 0.021(2) -0.002(2) I1 0.0578(3) 0.0514(3) 0.0238(3) -0.0045(2) -0.0081(2) 0.0184(2) I2 0.02703(18) 0.02651(19) 0.0246(2) 0.00387(18) -0.00125(17) 0.00246(16) I3 0.0601(3) 0.0588(3) 0.0222(3) 0.0034(2) -0.0034(2) -0.0111(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 C1 C2 1.365(8) . ? C1 N1 1.386(7) . ? C1 C6 1.419(6) . ? C2 C10 1.414(6) . ? C2 N2 1.428(7) . ? C11 C12 1.365(9) . ? C11 C16 1.394(9) . ? C11 N1 1.441(8) . ? C12 C13 1.369(10) . ? C12 H12 0.9500 . ? C13 C14 1.389(8) . ? C13 H13 0.9500 . ? C14 C15 1.384(9) . ? C14 C17 1.546(9) . ? C15 C16 1.395(9) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C26 1.529(10) . ? C17 C27 1.544(10) . ? C17 C25 1.545(9) . ? C18 C19 1.372(9) . ? C18 C23 1.396(8) . ? C18 N2 1.451(8) . ? C19 C20 1.367(9) . ? C19 H19 0.9500 . ? C20 C21 1.426(9) . ? C20 H20 0.9500 . ? C21 C22 1.382(9) . ? C21 C24 1.530(9) . ? C22 C23 1.391(9) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C29 1.517(9) . ? C24 C30 1.538(10) . ? C24 C28 1.542(11) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? N1 P1 1.663(5) . ? N2 P1 1.665(5) . ? C6 C5 1.444(6) . ? C6 C5A 1.552(7) . ? C6 S1A 1.643(5) . ? C6 S1 1.697(4) . ? S1 C3 1.690(5) . ? C3 C4 1.296(7) . ? C3 H3 0.9500 . ? C4 C5 1.477(7) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? S1A C3A 1.783(18) . ? C3A C4A 1.238(11) . ? C3A H3A 0.9500 . ? C4A C5A 1.382(10) . ? C4A H4A 0.9500 . ? C5A H5A 0.9500 . ? C10 C9 1.444(6) . ? C10 C9A 1.537(7) . ? C10 S2A 1.657(5) . ? C10 S2 1.699(4) . ? S2 C7 1.684(5) . ? C7 C8 1.301(7) . ? C7 H7 0.9500 . ? C8 C9 1.462(7) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? S2A C7A 1.795(18) . ? C7A C8A 1.228(11) . ? C7A H7A 0.9500 . ? C8A C9A 1.389(10) . ? C8A H8A 0.9500 . ? C9A H9A 0.9500 . ? I1 I2 3.0064(9) . ? I2 I3 2.8413(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 111.1(4) . . ? C2 C1 C6 124.2(4) . . ? N1 C1 C6 123.1(4) . . ? C1 C2 C10 131.6(4) . . ? C1 C2 N2 109.8(4) . . ? C10 C2 N2 118.5(4) . . ? C12 C11 C16 120.0(6) . . ? C12 C11 N1 120.8(6) . . ? C16 C11 N1 118.8(6) . . ? C11 C12 C13 120.6(6) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C14 121.5(6) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 117.5(6) . . ? C15 C14 C17 121.3(5) . . ? C13 C14 C17 121.2(6) . . ? C14 C15 C16 121.7(6) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.1 . . ? C11 C16 C15 118.6(6) . . ? C11 C16 H16 120.7 . . ? C15 C16 H16 120.7 . . ? C26 C17 C27 109.4(6) . . ? C26 C17 C25 108.7(6) . . ? C27 C17 C25 108.9(6) . . ? C26 C17 C14 112.0(6) . . ? C27 C17 C14 107.4(6) . . ? C25 C17 C14 110.4(5) . . ? C19 C18 C23 120.5(6) . . ? C19 C18 N2 120.0(5) . . ? C23 C18 N2 119.2(6) . . ? C20 C19 C18 120.1(6) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 121.6(6) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C22 C21 C20 116.7(6) . . ? C22 C21 C24 125.1(5) . . ? C20 C21 C24 118.2(6) . . ? C21 C22 C23 122.2(6) . . ? C21 C22 H22 118.9 . . ? C23 C22 H22 118.9 . . ? C22 C23 C18 118.9(6) . . ? C22 C23 H23 120.6 . . ? C18 C23 H23 120.6 . . ? C29 C24 C21 108.5(5) . . ? C29 C24 C30 108.5(6) . . ? C21 C24 C30 111.4(6) . . ? C29 C24 C28 109.4(6) . . ? C21 C24 C28 110.9(6) . . ? C30 C24 C28 108.0(6) . . ? C17 C25 H25A 109.5 . . ? C17 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C17 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C17 C26 H26A 109.5 . . ? C17 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C17 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C17 C27 H27A 109.5 . . ? C17 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C17 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C24 C30 H30A 109.5 . . ? C24 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C24 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C1 N1 C11 125.0(5) . . ? C1 N1 P1 115.2(4) . . ? C11 N1 P1 119.8(4) . . ? C2 N2 C18 124.8(5) . . ? C2 N2 P1 114.1(4) . . ? C18 N2 P1 119.8(4) . . ? N1 P1 N2 89.8(3) . . ? C1 C6 C5 121.9(4) . . ? C1 C6 C5A 111.1(4) . . ? C5 C6 C5A 126.6(6) . . ? C1 C6 S1A 137.3(5) . . ? C5A C6 S1A 111.6(5) . . ? C1 C6 S1 127.9(3) . . ? C5 C6 S1 110.2(3) . . ? S1A C6 S1 94.6(5) . . ? C3 S1 C6 93.2(3) . . ? C4 C3 S1 114.5(4) . . ? C4 C3 H3 122.7 . . ? S1 C3 H3 122.7 . . ? C3 C4 C5 113.0(5) . . ? C3 C4 H4 123.5 . . ? C5 C4 H4 123.5 . . ? C6 C5 C4 109.0(5) . . ? C6 C5 H5 125.5 . . ? C4 C5 H5 125.5 . . ? C6 S1A C3A 89.2(5) . . ? C4A C3A S1A 116.4(8) . . ? C4A C3A H3A 121.8 . . ? S1A C3A H3A 121.8 . . ? C3A C4A C5A 115.3(9) . . ? C3A C4A H4A 122.4 . . ? C5A C4A H4A 122.4 . . ? C4A C5A C6 107.6(6) . . ? C4A C5A H5A 126.2 . . ? C6 C5A H5A 126.2 . . ? C2 C10 C9 121.8(4) . . ? C2 C10 C9A 112.3(4) . . ? C9 C10 C9A 125.8(5) . . ? C2 C10 S2A 135.4(4) . . ? C9A C10 S2A 112.2(5) . . ? C2 C10 S2 129.0(3) . . ? C9 C10 S2 109.2(3) . . ? S2A C10 S2 95.6(5) . . ? C7 S2 C10 94.0(3) . . ? C8 C7 S2 113.5(4) . . ? C8 C7 H7 123.3 . . ? S2 C7 H7 123.3 . . ? C7 C8 C9 113.7(5) . . ? C7 C8 H8 123.2 . . ? C9 C8 H8 123.2 . . ? C10 C9 C8 109.6(4) . . ? C10 C9 H9 125.2 . . ? C8 C9 H9 125.2 . . ? C10 S2A C7A 88.1(4) . . ? C8A C7A S2A 116.9(8) . . ? C8A C7A H7A 121.6 . . ? S2A C7A H7A 121.6 . . ? C7A C8A C9A 115.2(8) . . ? C7A C8A H8A 122.4 . . ? C9A C8A H8A 122.4 . . ? C8A C9A C10 107.6(6) . . ? C8A C9A H9A 126.2 . . ? C10 C9A H9A 126.2 . . ? I3 I2 I1 179.02(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C10 -172.5(4) . . . . ? C6 C1 C2 C10 -6.4(8) . . . . ? N1 C1 C2 N2 2.5(6) . . . . ? C6 C1 C2 N2 168.7(4) . . . . ? C16 C11 C12 C13 -0.3(10) . . . . ? N1 C11 C12 C13 -173.3(6) . . . . ? C11 C12 C13 C14 0.3(10) . . . . ? C12 C13 C14 C15 -0.8(9) . . . . ? C12 C13 C14 C17 177.7(6) . . . . ? C13 C14 C15 C16 1.5(9) . . . . ? C17 C14 C15 C16 -177.1(6) . . . . ? C12 C11 C16 C15 0.9(9) . . . . ? N1 C11 C16 C15 174.0(5) . . . . ? C14 C15 C16 C11 -1.5(9) . . . . ? C15 C14 C17 C26 -20.9(9) . . . . ? C13 C14 C17 C26 160.6(6) . . . . ? C15 C14 C17 C27 99.2(7) . . . . ? C13 C14 C17 C27 -79.3(7) . . . . ? C15 C14 C17 C25 -142.2(6) . . . . ? C13 C14 C17 C25 39.4(9) . . . . ? C23 C18 C19 C20 0.7(10) . . . . ? N2 C18 C19 C20 -172.5(5) . . . . ? C18 C19 C20 C21 1.3(9) . . . . ? C19 C20 C21 C22 -2.8(9) . . . . ? C19 C20 C21 C24 175.1(6) . . . . ? C20 C21 C22 C23 2.3(9) . . . . ? C24 C21 C22 C23 -175.4(6) . . . . ? C21 C22 C23 C18 -0.4(9) . . . . ? C19 C18 C23 C22 -1.2(9) . . . . ? N2 C18 C23 C22 172.1(5) . . . . ? C22 C21 C24 C29 118.3(7) . . . . ? C20 C21 C24 C29 -59.3(8) . . . . ? C22 C21 C24 C30 -1.1(9) . . . . ? C20 C21 C24 C30 -178.7(6) . . . . ? C22 C21 C24 C28 -121.4(7) . . . . ? C20 C21 C24 C28 60.9(7) . . . . ? C2 C1 N1 C11 176.6(5) . . . . ? C6 C1 N1 C11 10.2(8) . . . . ? C2 C1 N1 P1 -4.1(6) . . . . ? C6 C1 N1 P1 -170.4(3) . . . . ? C12 C11 N1 C1 -90.9(7) . . . . ? C16 C11 N1 C1 96.0(7) . . . . ? C12 C11 N1 P1 89.7(7) . . . . ? C16 C11 N1 P1 -83.3(6) . . . . ? C1 C2 N2 C18 166.2(5) . . . . ? C10 C2 N2 C18 -18.1(7) . . . . ? C1 C2 N2 P1 -0.1(6) . . . . ? C10 C2 N2 P1 175.7(3) . . . . ? C19 C18 N2 C2 -56.9(8) . . . . ? C23 C18 N2 C2 129.8(6) . . . . ? C19 C18 N2 P1 108.7(6) . . . . ? C23 C18 N2 P1 -64.7(7) . . . . ? C1 N1 P1 N2 3.4(4) . . . . ? C11 N1 P1 N2 -177.2(5) . . . . ? C2 N2 P1 N1 -1.8(4) . . . . ? C18 N2 P1 N1 -168.9(5) . . . . ? C2 C1 C6 C5 126.0(5) . . . . ? N1 C1 C6 C5 -69.5(5) . . . . ? C2 C1 C6 C5A -61(2) . . . . ? N1 C1 C6 C5A 104(2) . . . . ? C2 C1 C6 S1A 119(2) . . . . ? N1 C1 C6 S1A -76(2) . . . . ? C2 C1 C6 S1 -54.1(5) . . . . ? N1 C1 C6 S1 110.5(5) . . . . ? C1 C6 S1 C3 -179.9(2) . . . . ? C5 C6 S1 C3 0.08(19) . . . . ? C5A C6 S1 C3 -159(6) . . . . ? S1A C6 S1 C3 4.7(14) . . . . ? C6 S1 C3 C4 0.15(16) . . . . ? S1 C3 C4 C5 -0.3(3) . . . . ? C1 C6 C5 C4 179.7(2) . . . . ? C5A C6 C5 C4 8(2) . . . . ? S1A C6 C5 C4 -17(5) . . . . ? S1 C6 C5 C4 -0.2(3) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C1 C6 S1A C3A -179.8(2) . . . . ? C5 C6 S1A C3A 159(6) . . . . ? C5A C6 S1A C3A 0.2(4) . . . . ? S1 C6 S1A C3A -5.1(16) . . . . ? C6 S1A C3A C4A -0.4(6) . . . . ? S1A C3A C4A C5A 0.5(10) . . . . ? C3A C4A C5A C6 -0.3(9) . . . . ? C1 C6 C5A C4A 180.0(5) . . . . ? C5 C6 C5A C4A -7(2) . . . . ? S1A C6 C5A C4A -0.1(6) . . . . ? S1 C6 C5A C4A 18(5) . . . . ? C1 C2 C10 C9 -54.6(6) . . . . ? N2 C2 C10 C9 130.8(4) . . . . ? C1 C2 C10 C9A 127.9(12) . . . . ? N2 C2 C10 C9A -46.7(12) . . . . ? C1 C2 C10 S2A -52.1(12) . . . . ? N2 C2 C10 S2A 133.2(12) . . . . ? C1 C2 C10 S2 125.5(5) . . . . ? N2 C2 C10 S2 -49.2(5) . . . . ? C2 C10 S2 C7 179.9(2) . . . . ? C9 C10 S2 C7 -0.03(19) . . . . ? C9A C10 S2 C7 172(4) . . . . ? S2A C10 S2 C7 -1.8(8) . . . . ? C10 S2 C7 C8 -0.13(16) . . . . ? S2 C7 C8 C9 0.3(3) . . . . ? C2 C10 C9 C8 -179.8(2) . . . . ? C9A C10 C9 C8 -2.7(14) . . . . ? S2A C10 C9 C8 7(4) . . . . ? S2 C10 C9 C8 0.2(3) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? C2 C10 S2A C7A 179.9(2) . . . . ? C9 C10 S2A C7A -171(4) . . . . ? C9A C10 S2A C7A -0.1(4) . . . . ? S2 C10 S2A C7A 1.8(10) . . . . ? C10 S2A C7A C8A 0.2(6) . . . . ? S2A C7A C8A C9A -0.2(10) . . . . ? C7A C8A C9A C10 0.0(9) . . . . ? C2 C10 C9A C8A -179.9(4) . . . . ? C9 C10 C9A C8A 2.7(14) . . . . ? S2A C10 C9A C8A 0.1(6) . . . . ? S2 C10 C9A C8A -7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.147 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.122 # Attachment 'jbkv090b1.cif' data_jbkv090b _database_code_depnum_ccdc_archive 'CCDC 707517' _audit_creation_method ; manual editing of the .cif file created by SHELXTL Ver. 6.10 ; _publ_section_synopsis ; ; _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380-388. Cremer D. & Pople J.A. (1975). J. Am. Chem. Soc. 97, 1358-1367. Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. Sir97. (1999) J. Appl. Cryst. 32, 115-119. Otwinowski, Z. and Minor, W. (1997). Methods in Enzymology, 276, Macromolecular Crystallography, part A, 307-326, C. W. Carter, Jr. and R. M. Sweets, Eds., Academic Press. Sheldrick, G. M. (1998). SHELXTL/PC. Release 5.10. Siemens Analytical X-ray Instruments, Inc., Madison, WI, USA. Sluis, P. v.d. & Spek, A. L. (1990). SQUEEZE. Acta Cryst. A46, 194-201. Spek, A. L. (1998) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; _publ_section_figure_captions ; ; _publ_section_exptl_prep ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H26 Cl2 N2 S2' _chemical_formula_sum 'C35 H26 Cl2 N2 S2' _chemical_formula_weight 609.60 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' S S 0.1246 0.1234 '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 -p1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5726(19) _cell_length_b 10.449(2) _cell_length_c 15.535(3) _cell_angle_alpha 100.09(3) _cell_angle_beta 103.56(3) _cell_angle_gamma 95.64(3) _cell_volume 1471.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 17032 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.969 _exptl_absorpt_process_details 'DENZO and Scalepack (Otwinoski and Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Nonius Kappa CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10484 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.1450 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6669 _reflns_number_gt 3329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect software, Nonius B.V. 1998' _computing_cell_refinement 'Collect software, Nonius B.V. 1998' _computing_data_reduction ; DENZO and Scalepack (Otwinoski and Minor, 1997) ; _computing_structure_solution ; SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. ; _computing_structure_refinement 'XL SHELXTL/PC, Siemens Analytical' _computing_molecular_graphics 'XP SHELXTL/PC, Siemens Analytical' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0560P)^2^+0.8140P] 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 6669 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1750 _refine_ls_R_factor_gt 0.0709 _refine_ls_wR_factor_ref 0.1649 _refine_ls_wR_factor_gt 0.1326 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 C1 C 0.3919(3) 0.3127(3) 0.2168(2) 0.0197(8) Uani 1 1 d . . . C2 C 0.2852(3) 0.4087(3) 0.2274(2) 0.0196(8) Uani 1 1 d . . . C3 C 0.5462(4) 0.3687(3) 0.2280(2) 0.0205(8) Uani 1 1 d . . . C4 C 0.6412(4) 0.2899(4) 0.1979(2) 0.0240(8) Uani 1 1 d . . . H4 H 0.6081 0.2021 0.1708 0.029 Uiso 1 1 calc R . . C5 C 0.7830(4) 0.3402(4) 0.2078(2) 0.0309(9) Uani 1 1 d . . . H5 H 0.8456 0.2865 0.1875 0.037 Uiso 1 1 calc R . . C6 C 0.8330(4) 0.4706(4) 0.2479(2) 0.0339(10) Uani 1 1 d . . . H6 H 0.9289 0.5050 0.2537 0.041 Uiso 1 1 calc R . . C7 C 0.7413(4) 0.5494(4) 0.2790(2) 0.0294(9) Uani 1 1 d . . . H7 H 0.7760 0.6367 0.3070 0.035 Uiso 1 1 calc R . . C8 C 0.5976(4) 0.4998(3) 0.2688(2) 0.0240(8) Uani 1 1 d . . . H8 H 0.5355 0.5539 0.2892 0.029 Uiso 1 1 calc R . . C9 C 0.2503(3) 0.4877(3) 0.1557(2) 0.0196(8) Uani 1 1 d . . . C10 C 0.2808(4) 0.4489(3) 0.0725(2) 0.0233(8) Uani 1 1 d . . . H10 H 0.3296 0.3771 0.0629 0.028 Uiso 1 1 calc R . . C11 C 0.2389(4) 0.5165(3) 0.0038(2) 0.0290(9) Uani 1 1 d . . . H11 H 0.2594 0.4900 -0.0517 0.035 Uiso 1 1 calc R . . C12 C 0.1670(4) 0.6232(4) 0.0178(2) 0.0325(10) Uani 1 1 d . . . H12 H 0.1373 0.6677 -0.0286 0.039 Uiso 1 1 calc R . . C13 C 0.1390(4) 0.6639(4) 0.1004(3) 0.0350(10) Uani 1 1 d . . . H13 H 0.0919 0.7368 0.1102 0.042 Uiso 1 1 calc R . . C14 C 0.1807(4) 0.5967(3) 0.1687(2) 0.0286(9) Uani 1 1 d . . . H14 H 0.1619 0.6251 0.2245 0.034 Uiso 1 1 calc R . . C15 C 0.2133(4) 0.1266(3) 0.1827(2) 0.0227(8) Uani 1 1 d . . . C16 C 0.1824(4) 0.0343(3) 0.2332(2) 0.0285(9) Uani 1 1 d . . . H16 H 0.2551 0.0198 0.2803 0.034 Uiso 1 1 calc R . . C17 C 0.0453(4) -0.0353(3) 0.2137(2) 0.0283(9) Uani 1 1 d . . . H17 H 0.0258 -0.0945 0.2491 0.034 Uiso 1 1 calc R . . C18 C -0.0656(4) -0.0187(3) 0.1415(2) 0.0229(8) Uani 1 1 d . . . C19 C -0.0335(4) 0.0744(3) 0.0922(2) 0.0246(8) Uani 1 1 d . . . H19 H -0.1058 0.0882 0.0445 0.030 Uiso 1 1 calc R . . C20 C 0.1022(4) 0.1462(3) 0.1122(2) 0.0244(8) Uani 1 1 d . . . H20 H 0.1202 0.2084 0.0785 0.029 Uiso 1 1 calc R . . C21 C -0.2087(4) -0.0998(3) 0.1187(2) 0.0245(8) Uani 1 1 d . . . C22 C -0.2497(4) -0.2115(3) 0.1500(2) 0.0311(9) Uani 1 1 d . . . H22 H -0.1867 -0.2496 0.1899 0.037 Uiso 1 1 calc R . . C23 C -0.4001(4) -0.2593(4) 0.1129(3) 0.0387(10) Uani 1 1 d . . . H23 H -0.4463 -0.3330 0.1264 0.046 Uiso 1 1 calc R . . C24 C -0.4689(4) -0.1888(4) 0.0570(3) 0.0393(10) Uani 1 1 d . . . H24 H -0.5673 -0.2076 0.0276 0.047 Uiso 1 1 calc R . . C25 C 0.2515(4) 0.3502(3) 0.3618(2) 0.0229(8) Uani 1 1 d . . . C26 C 0.3897(4) 0.3444(3) 0.4139(2) 0.0290(9) Uani 1 1 d . . . H26 H 0.4706 0.3892 0.4030 0.035 Uiso 1 1 calc R . . C27 C 0.4083(4) 0.2728(3) 0.4815(2) 0.0293(9) Uani 1 1 d . . . H27 H 0.5016 0.2703 0.5155 0.035 Uiso 1 1 calc R . . C28 C 0.2893(4) 0.2039(3) 0.4998(2) 0.0256(8) Uani 1 1 d . . . C29 C 0.1514(4) 0.2134(3) 0.4486(2) 0.0288(9) Uani 1 1 d . . . H29 H 0.0703 0.1693 0.4596 0.035 Uiso 1 1 calc R . . C30 C 0.1324(4) 0.2863(3) 0.3821(2) 0.0261(9) Uani 1 1 d . . . H30 H 0.0390 0.2930 0.3504 0.031 Uiso 1 1 calc R . . C31 C 0.3063(4) 0.1222(3) 0.5692(2) 0.0309(9) Uani 1 1 d . . . C32 C 0.1945(4) 0.0591(3) 0.6012(2) 0.0217(8) Uani 1 1 d . . . H32 H 0.0961 0.0657 0.5835 0.026 Uiso 1 1 calc R . . C33 C 0.2592(5) -0.0156(4) 0.6648(3) 0.0408(11) Uani 1 1 d . . . H33 H 0.2046 -0.0666 0.6920 0.049 Uiso 1 1 calc R . . C34 C 0.4019(5) -0.0070(5) 0.6820(3) 0.0600(14) Uani 1 1 d . . . H34 H 0.4570 -0.0504 0.7222 0.072 Uiso 1 1 calc R . . C35 C 0.1019(4) 0.6349(4) 0.4417(3) 0.0406(10) Uani 1 1 d . . . H35A H 0.0000 0.6284 0.4413 0.049 Uiso 1 1 calc R . . H35B H 0.1130 0.5615 0.3972 0.049 Uiso 1 1 calc R . . N1 N 0.3580(3) 0.1874(3) 0.19979(17) 0.0217(7) Uani 1 1 d . . . N2 N 0.2226(3) 0.4232(3) 0.29169(17) 0.0216(7) Uani 1 1 d . . . S1 S 0.47343(14) 0.09167(18) 0.62293(11) 0.0916(6) Uani 1 1 d . . . S2 S -0.35525(11) -0.06078(11) 0.04587(8) 0.0464(3) Uani 1 1 d . . . Cl1 Cl 0.20299(12) 0.62344(12) 0.54814(7) 0.0516(3) Uani 1 1 d . . . Cl2 Cl 0.15431(14) 0.78190(11) 0.41061(8) 0.0601(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0181(19) 0.029(2) 0.0139(17) 0.0095(15) 0.0027(14) 0.0040(16) C2 0.0116(18) 0.0215(19) 0.0240(19) 0.0059(15) 0.0020(15) -0.0021(15) C3 0.018(2) 0.029(2) 0.0167(17) 0.0125(16) 0.0044(15) 0.0046(16) C4 0.024(2) 0.030(2) 0.0206(18) 0.0083(16) 0.0061(16) 0.0079(17) C5 0.023(2) 0.051(3) 0.025(2) 0.0149(19) 0.0100(16) 0.0128(19) C6 0.017(2) 0.056(3) 0.031(2) 0.020(2) 0.0036(17) -0.003(2) C7 0.025(2) 0.030(2) 0.031(2) 0.0123(17) 0.0019(17) -0.0028(18) C8 0.024(2) 0.026(2) 0.0265(19) 0.0123(17) 0.0079(16) 0.0061(16) C9 0.0125(18) 0.0218(19) 0.0243(19) 0.0088(16) 0.0022(15) 0.0006(15) C10 0.023(2) 0.021(2) 0.029(2) 0.0078(16) 0.0086(16) 0.0053(16) C11 0.030(2) 0.033(2) 0.025(2) 0.0114(17) 0.0051(17) 0.0011(18) C12 0.031(2) 0.035(2) 0.035(2) 0.0230(19) 0.0053(18) 0.0025(19) C13 0.041(3) 0.031(2) 0.044(2) 0.0199(19) 0.018(2) 0.0166(19) C14 0.034(2) 0.028(2) 0.029(2) 0.0118(17) 0.0128(17) 0.0078(18) C15 0.022(2) 0.021(2) 0.0252(19) 0.0024(16) 0.0077(16) 0.0038(16) C16 0.026(2) 0.030(2) 0.028(2) 0.0114(17) -0.0007(16) 0.0029(17) C17 0.026(2) 0.026(2) 0.033(2) 0.0143(17) 0.0063(17) -0.0038(17) C18 0.020(2) 0.021(2) 0.0271(19) 0.0021(16) 0.0069(16) 0.0037(16) C19 0.024(2) 0.022(2) 0.0235(19) 0.0057(16) -0.0020(16) 0.0017(16) C20 0.026(2) 0.0196(19) 0.029(2) 0.0096(16) 0.0069(16) 0.0012(16) C21 0.027(2) 0.021(2) 0.0238(19) 0.0009(16) 0.0067(16) 0.0018(16) C22 0.028(2) 0.022(2) 0.038(2) 0.0088(17) -0.0001(18) -0.0066(17) C23 0.039(3) 0.032(2) 0.042(2) 0.011(2) 0.008(2) -0.010(2) C24 0.025(2) 0.038(2) 0.049(3) 0.010(2) 0.0029(19) -0.0077(19) C25 0.022(2) 0.026(2) 0.0248(19) 0.0080(16) 0.0095(16) 0.0063(16) C26 0.025(2) 0.038(2) 0.027(2) 0.0137(18) 0.0104(17) 0.0003(18) C27 0.020(2) 0.043(2) 0.025(2) 0.0136(18) 0.0027(16) 0.0052(18) C28 0.028(2) 0.030(2) 0.0221(19) 0.0102(16) 0.0091(16) 0.0072(17) C29 0.023(2) 0.032(2) 0.034(2) 0.0107(18) 0.0122(17) 0.0007(17) C30 0.020(2) 0.033(2) 0.0292(19) 0.0127(17) 0.0063(16) 0.0093(17) C31 0.036(2) 0.031(2) 0.030(2) 0.0093(18) 0.0101(18) 0.0129(18) C32 0.030(2) 0.0145(18) 0.0173(17) 0.0106(15) -0.0017(15) -0.0047(16) C33 0.052(3) 0.039(2) 0.038(2) 0.017(2) 0.021(2) 0.004(2) C34 0.053(3) 0.089(4) 0.067(3) 0.060(3) 0.028(3) 0.037(3) C35 0.037(3) 0.046(3) 0.040(2) 0.011(2) 0.0089(19) 0.011(2) N1 0.0208(17) 0.0221(17) 0.0234(15) 0.0081(13) 0.0055(13) 0.0035(13) N2 0.0190(16) 0.0256(17) 0.0228(15) 0.0093(13) 0.0076(13) 0.0018(13) S1 0.0463(8) 0.1578(15) 0.1173(12) 0.1128(12) 0.0377(8) 0.0434(9) S2 0.0252(6) 0.0447(7) 0.0666(8) 0.0272(6) -0.0018(5) -0.0040(5) Cl1 0.0426(7) 0.0778(9) 0.0372(6) 0.0230(6) 0.0066(5) 0.0105(6) Cl2 0.0836(10) 0.0530(7) 0.0544(7) 0.0244(6) 0.0273(7) 0.0135(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.282(4) . ? C1 C3 1.493(4) . ? C1 C2 1.516(5) . ? C2 N2 1.275(4) . ? C2 C9 1.494(4) . ? C3 C8 1.391(5) . ? C3 C4 1.392(5) . ? C4 C5 1.369(5) . ? C4 H4 0.9300 . ? C5 C6 1.381(5) . ? C5 H5 0.9300 . ? C6 C7 1.373(5) . ? C6 H6 0.9300 . ? C7 C8 1.384(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C14 1.383(5) . ? C9 C10 1.392(5) . ? C10 C11 1.384(4) . ? C10 H10 0.9300 . ? C11 C12 1.379(5) . ? C11 H11 0.9300 . ? C12 C13 1.376(5) . ? C12 H12 0.9300 . ? C13 C14 1.377(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.396(4) . ? C15 C20 1.396(4) . ? C15 N1 1.410(4) . ? C16 C17 1.376(5) . ? C16 H16 0.9300 . ? C17 C18 1.400(5) . ? C17 H17 0.9300 . ? C18 C19 1.393(4) . ? C18 C21 1.469(5) . ? C19 C20 1.373(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.396(4) . ? C21 S2 1.716(3) . ? C22 C23 1.423(5) . ? C22 H22 0.9300 . ? C23 C24 1.335(5) . ? C23 H23 0.9300 . ? C24 S2 1.699(4) . ? C24 H24 0.9300 . ? C25 C30 1.392(4) . ? C25 C26 1.393(5) . ? C25 N2 1.426(4) . ? C26 C27 1.382(4) . ? C26 H26 0.9300 . ? C27 C28 1.399(5) . ? C27 H27 0.9300 . ? C28 C29 1.395(5) . ? C28 C31 1.478(4) . ? C29 C30 1.377(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C31 C32 1.432(5) . ? C31 S1 1.711(4) . ? C32 C33 1.431(5) . ? C32 H32 0.9300 . ? C33 C34 1.320(6) . ? C33 H33 0.9300 . ? C34 S1 1.692(4) . ? C34 H34 0.9300 . ? C35 Cl1 1.740(4) . ? C35 Cl2 1.751(4) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C3 118.4(3) . . ? N1 C1 C2 124.1(3) . . ? C3 C1 C2 117.4(3) . . ? N2 C2 C9 119.1(3) . . ? N2 C2 C1 124.1(3) . . ? C9 C2 C1 116.8(3) . . ? C8 C3 C4 118.9(3) . . ? C8 C3 C1 120.9(3) . . ? C4 C3 C1 120.2(3) . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 120.1(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.4(4) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C7 C8 C3 119.9(3) . . ? C7 C8 H8 120.1 . . ? C3 C8 H8 120.1 . . ? C14 C9 C10 118.5(3) . . ? C14 C9 C2 121.0(3) . . ? C10 C9 C2 120.4(3) . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.1(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 119.9(4) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C9 121.1(3) . . ? C13 C14 H14 119.5 . . ? C9 C14 H14 119.5 . . ? C16 C15 C20 118.5(3) . . ? C16 C15 N1 118.7(3) . . ? C20 C15 N1 122.6(3) . . ? C17 C16 C15 120.5(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 121.2(3) . . ? C16 C17 H17 119.4 . . ? C18 C17 H17 119.4 . . ? C19 C18 C17 117.6(3) . . ? C19 C18 C21 122.2(3) . . ? C17 C18 C21 120.2(3) . . ? C20 C19 C18 121.7(3) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C19 C20 C15 120.5(3) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? C22 C21 C18 128.9(3) . . ? C22 C21 S2 110.3(3) . . ? C18 C21 S2 120.8(2) . . ? C21 C22 C23 111.3(3) . . ? C21 C22 H22 124.4 . . ? C23 C22 H22 124.4 . . ? C24 C23 C22 113.8(3) . . ? C24 C23 H23 123.1 . . ? C22 C23 H23 123.1 . . ? C23 C24 S2 112.0(3) . . ? C23 C24 H24 124.0 . . ? S2 C24 H24 124.0 . . ? C30 C25 C26 118.2(3) . . ? C30 C25 N2 117.3(3) . . ? C26 C25 N2 124.5(3) . . ? C27 C26 C25 120.8(3) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 121.2(3) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C29 C28 C27 117.2(3) . . ? C29 C28 C31 120.4(3) . . ? C27 C28 C31 122.4(3) . . ? C30 C29 C28 121.7(3) . . ? C30 C29 H29 119.2 . . ? C28 C29 H29 119.2 . . ? C29 C30 C25 120.7(3) . . ? C29 C30 H30 119.6 . . ? C25 C30 H30 119.6 . . ? C32 C31 C28 127.7(3) . . ? C32 C31 S1 110.8(2) . . ? C28 C31 S1 121.5(3) . . ? C31 C32 C33 108.8(3) . . ? C31 C32 H32 125.6 . . ? C33 C32 H32 125.6 . . ? C34 C33 C32 115.2(3) . . ? C34 C33 H33 122.4 . . ? C32 C33 H33 122.4 . . ? C33 C34 S1 112.5(3) . . ? C33 C34 H34 123.7 . . ? S1 C34 H34 123.7 . . ? Cl1 C35 Cl2 112.7(2) . . ? Cl1 C35 H35A 109.1 . . ? Cl2 C35 H35A 109.1 . . ? Cl1 C35 H35B 109.1 . . ? Cl2 C35 H35B 109.1 . . ? H35A C35 H35B 107.8 . . ? C1 N1 C15 122.0(3) . . ? C2 N2 C25 121.5(3) . . ? C34 S1 C31 92.6(2) . . ? C24 S2 C21 92.65(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 N2 66.3(4) . . . . ? C3 C1 C2 N2 -113.0(3) . . . . ? N1 C1 C2 C9 -112.0(3) . . . . ? C3 C1 C2 C9 68.6(4) . . . . ? N1 C1 C3 C8 -163.3(3) . . . . ? C2 C1 C3 C8 16.1(4) . . . . ? N1 C1 C3 C4 16.5(4) . . . . ? C2 C1 C3 C4 -164.1(3) . . . . ? C8 C3 C4 C5 -0.3(4) . . . . ? C1 C3 C4 C5 180.0(3) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? C4 C5 C6 C7 0.9(5) . . . . ? C5 C6 C7 C8 -1.3(5) . . . . ? C6 C7 C8 C3 1.0(5) . . . . ? C4 C3 C8 C7 -0.2(4) . . . . ? C1 C3 C8 C7 179.6(3) . . . . ? N2 C2 C9 C14 15.9(5) . . . . ? C1 C2 C9 C14 -165.7(3) . . . . ? N2 C2 C9 C10 -160.9(3) . . . . ? C1 C2 C9 C10 17.6(4) . . . . ? C14 C9 C10 C11 -1.6(5) . . . . ? C2 C9 C10 C11 175.3(3) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C10 C11 C12 C13 1.2(5) . . . . ? C11 C12 C13 C14 -1.1(6) . . . . ? C12 C13 C14 C9 -0.3(6) . . . . ? C10 C9 C14 C13 1.6(5) . . . . ? C2 C9 C14 C13 -175.2(3) . . . . ? C20 C15 C16 C17 -0.1(5) . . . . ? N1 C15 C16 C17 -174.6(3) . . . . ? C15 C16 C17 C18 1.9(6) . . . . ? C16 C17 C18 C19 -2.3(5) . . . . ? C16 C17 C18 C21 176.4(3) . . . . ? C17 C18 C19 C20 1.0(5) . . . . ? C21 C18 C19 C20 -177.6(3) . . . . ? C18 C19 C20 C15 0.7(5) . . . . ? C16 C15 C20 C19 -1.2(5) . . . . ? N1 C15 C20 C19 173.0(3) . . . . ? C19 C18 C21 C22 167.2(4) . . . . ? C17 C18 C21 C22 -11.4(6) . . . . ? C19 C18 C21 S2 -14.1(5) . . . . ? C17 C18 C21 S2 167.3(3) . . . . ? C18 C21 C22 C23 178.5(4) . . . . ? S2 C21 C22 C23 -0.3(4) . . . . ? C21 C22 C23 C24 0.1(5) . . . . ? C22 C23 C24 S2 0.1(5) . . . . ? C30 C25 C26 C27 2.5(5) . . . . ? N2 C25 C26 C27 179.0(3) . . . . ? C25 C26 C27 C28 0.1(6) . . . . ? C26 C27 C28 C29 -1.6(5) . . . . ? C26 C27 C28 C31 177.4(3) . . . . ? C27 C28 C29 C30 0.6(5) . . . . ? C31 C28 C29 C30 -178.5(3) . . . . ? C28 C29 C30 C25 2.0(5) . . . . ? C26 C25 C30 C29 -3.5(5) . . . . ? N2 C25 C30 C29 179.7(3) . . . . ? C29 C28 C31 C32 -8.4(6) . . . . ? C27 C28 C31 C32 172.5(4) . . . . ? C29 C28 C31 S1 171.6(3) . . . . ? C27 C28 C31 S1 -7.5(5) . . . . ? C28 C31 C32 C33 176.8(3) . . . . ? S1 C31 C32 C33 -3.2(4) . . . . ? C31 C32 C33 C34 2.2(5) . . . . ? C32 C33 C34 S1 -0.3(5) . . . . ? C3 C1 N1 C15 -176.0(3) . . . . ? C2 C1 N1 C15 4.6(5) . . . . ? C16 C15 N1 C1 -127.1(3) . . . . ? C20 C15 N1 C1 58.7(5) . . . . ? C9 C2 N2 C25 179.9(3) . . . . ? C1 C2 N2 C25 1.5(5) . . . . ? C30 C25 N2 C2 -130.3(3) . . . . ? C26 C25 N2 C2 53.1(5) . . . . ? C33 C34 S1 C31 -1.4(4) . . . . ? C32 C31 S1 C34 2.7(3) . . . . ? C28 C31 S1 C34 -177.3(3) . . . . ? C23 C24 S2 C21 -0.3(3) . . . . ? C22 C21 S2 C24 0.4(3) . . . . ? C18 C21 S2 C24 -178.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.427 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.073