# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Bernard Mark Heron' _publ_contact_author_email B.M.HERON@LEEDS.AC.UK _publ_section_title ; Ring Contraction During the 6pi-Electrocyclisation of Naphthopyran Valence Tautomers ; loop_ _publ_author_name 'B Mark Heron' 'Simon Coles' 'Christopher D Gabbutt' 'Peter N Horton' 'Mike Hursthouse' ; C.Kilner ; 'Suresh B. Kolla' # Attachment 'ccdc661552.CIF' data_compound_6 _database_code_depnum_ccdc_archive 'CCDC 661552' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H16 O3 S' _chemical_formula_sum 'C25 H16 O3 S' _chemical_formula_weight 396.44 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' O O 0.0106 0.0060 '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 monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.97170(10) _cell_length_b 20.6854(3) _cell_length_c 11.1804(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.1430(7) _cell_angle_gamma 90.00 _cell_volume 1808.87(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 24270 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 34563 _diffrn_reflns_av_R_equivalents 0.0840 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3553 _reflns_number_gt 3006 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 2004)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution ; SIR92 Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Cryst. 1994, 27, 435-436. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; ORTEP-III Version 1.08 (Farrugia, 2005) ; _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; The structure solved in the monoclinic spacegroup P21/n. All hydrogen atoms could be located in the Fourier difference map but, in the final stages of the refinement, they were placed in calculated positions and refined using a riding model. C-H distances: CH, 1.00\A; aromatic, 0.95\A, olefinic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. 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^)+(0.0568P)^2^+0.7477P] 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 3553 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2 C 0.0489(2) 0.13082(8) 0.58869(15) 0.0235(3) Uani 1 1 d . . . C3 C -0.0433(2) 0.07723(8) 0.61410(16) 0.0274(4) Uani 1 1 d . . . H3 H -0.0646 0.0422 0.5582 0.033 Uiso 1 1 calc R . . C4 C -0.1040(2) 0.07560(9) 0.72240(17) 0.0319(4) Uani 1 1 d . . . H4 H -0.1680 0.0395 0.7410 0.038 Uiso 1 1 calc R . . C5 C -0.0707(2) 0.12675(9) 0.80305(17) 0.0332(4) Uani 1 1 d . . . H5 H -0.1121 0.1255 0.8772 0.040 Uiso 1 1 calc R . . C6 C 0.0225(2) 0.17992(9) 0.77695(16) 0.0303(4) Uani 1 1 d . . . H6 H 0.0447 0.2145 0.8337 0.036 Uiso 1 1 calc R . . C7 C 0.0838(2) 0.18307(8) 0.66852(15) 0.0250(4) Uani 1 1 d . . . C8 C 0.1929(2) 0.24046(8) 0.64353(15) 0.0249(4) Uani 1 1 d . . . H8 H 0.2479 0.2582 0.7249 0.030 Uiso 1 1 calc R . . C9 C 0.3376(2) 0.22073(8) 0.58009(15) 0.0247(3) Uani 1 1 d . . . C10 C 0.4977(2) 0.24949(8) 0.61307(16) 0.0290(4) Uani 1 1 d . . . H10 H 0.5144 0.2831 0.6721 0.035 Uiso 1 1 calc R . . C11 C 0.6332(2) 0.22957(9) 0.56053(16) 0.0310(4) Uani 1 1 d . . . H11 H 0.7418 0.2496 0.5843 0.037 Uiso 1 1 calc R . . C12 C 0.6118(2) 0.18074(9) 0.47357(16) 0.0302(4) Uani 1 1 d . . . H12 H 0.7052 0.1676 0.4379 0.036 Uiso 1 1 calc R . . C13 C 0.4538(2) 0.15134(8) 0.43919(15) 0.0269(4) Uani 1 1 d . . . H13 H 0.4377 0.1176 0.3804 0.032 Uiso 1 1 calc R . . C14 C 0.3188(2) 0.17204(8) 0.49231(15) 0.0237(3) Uani 1 1 d . . . C81 C 0.0899(2) 0.29479(8) 0.57579(15) 0.0252(4) Uani 1 1 d . . . C83 C -0.0906(2) 0.37632(8) 0.56695(15) 0.0258(4) Uani 1 1 d . . . C84 C -0.2032(2) 0.42233(8) 0.59899(16) 0.0299(4) Uani 1 1 d . . . H84 H -0.2410 0.4203 0.6744 0.036 Uiso 1 1 calc R . . C85 C -0.2557(2) 0.47026(8) 0.51609(16) 0.0313(4) Uani 1 1 d . . . H85 H -0.3313 0.5025 0.5350 0.038 Uiso 1 1 calc R . . C86 C -0.2008(2) 0.47355(8) 0.40192(16) 0.0292(4) Uani 1 1 d . . . C87 C -0.2518(2) 0.52486(9) 0.31879(17) 0.0340(4) Uani 1 1 d . . . H87 H -0.3241 0.5579 0.3391 0.041 Uiso 1 1 calc R . . C88 C -0.1984(2) 0.52750(9) 0.20985(17) 0.0363(4) Uani 1 1 d . . . H88 H -0.2338 0.5623 0.1554 0.044 Uiso 1 1 calc R . . C89 C -0.0918(2) 0.47918(9) 0.17771(17) 0.0353(4) Uani 1 1 d . . . H89 H -0.0552 0.4816 0.1019 0.042 Uiso 1 1 calc R . . C90 C -0.0399(2) 0.42839(9) 0.25535(16) 0.0310(4) Uani 1 1 d . . . H90 H 0.0307 0.3955 0.2322 0.037 Uiso 1 1 calc R . . C91 C -0.0911(2) 0.42478(8) 0.36944(15) 0.0269(4) Uani 1 1 d . . . C92 C -0.0360(2) 0.37519(8) 0.45706(15) 0.0258(4) Uani 1 1 d . . . C93 C 0.0800(2) 0.32136(8) 0.46433(16) 0.0265(4) Uani 1 1 d . . . H93 H 0.1384 0.3073 0.4026 0.032 Uiso 1 1 calc R . . O1 O 0.00372(15) 0.17374(6) 0.36649(11) 0.0317(3) Uani 1 1 d . . . O2 O 0.14789(16) 0.06870(6) 0.40829(11) 0.0319(3) Uani 1 1 d . . . O82 O -0.01454(14) 0.32724(5) 0.64175(10) 0.0263(3) Uani 1 1 d . . . S1 S 0.11952(5) 0.133079(19) 0.44924(4) 0.02435(14) 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 C2 0.0230(8) 0.0229(8) 0.0245(8) 0.0016(6) 0.0044(6) 0.0022(6) C3 0.0256(8) 0.0229(8) 0.0330(9) 0.0022(7) 0.0043(7) 0.0008(6) C4 0.0324(9) 0.0258(9) 0.0400(10) 0.0072(8) 0.0132(8) 0.0012(7) C5 0.0382(10) 0.0320(10) 0.0328(9) 0.0068(8) 0.0154(8) 0.0064(8) C6 0.0370(10) 0.0254(9) 0.0298(9) 0.0003(7) 0.0096(7) 0.0054(7) C7 0.0253(8) 0.0218(8) 0.0272(8) 0.0027(6) 0.0035(7) 0.0033(6) C8 0.0280(8) 0.0213(8) 0.0249(8) -0.0020(6) 0.0041(7) -0.0003(6) C9 0.0269(8) 0.0213(8) 0.0251(8) 0.0028(6) 0.0027(7) 0.0010(6) C10 0.0301(9) 0.0251(9) 0.0295(9) -0.0016(7) 0.0004(7) -0.0029(7) C11 0.0238(8) 0.0301(9) 0.0370(10) 0.0038(8) 0.0008(7) -0.0025(7) C12 0.0271(9) 0.0286(9) 0.0356(9) 0.0045(7) 0.0083(7) 0.0034(7) C13 0.0300(8) 0.0236(8) 0.0279(9) 0.0019(7) 0.0072(7) 0.0014(7) C14 0.0244(8) 0.0215(8) 0.0243(8) 0.0023(6) 0.0025(6) -0.0010(6) C81 0.0252(8) 0.0200(8) 0.0310(9) -0.0040(7) 0.0070(7) -0.0015(6) C83 0.0270(8) 0.0208(8) 0.0289(9) 0.0000(7) 0.0036(7) -0.0026(6) C84 0.0297(9) 0.0293(9) 0.0312(9) -0.0023(7) 0.0069(7) 0.0015(7) C85 0.0279(9) 0.0256(9) 0.0389(10) -0.0029(8) 0.0030(7) 0.0035(7) C86 0.0254(8) 0.0252(9) 0.0339(9) -0.0011(7) -0.0019(7) -0.0031(7) C87 0.0303(9) 0.0248(9) 0.0427(10) 0.0009(8) -0.0032(8) -0.0006(7) C88 0.0369(10) 0.0294(10) 0.0377(10) 0.0083(8) -0.0051(8) -0.0066(8) C89 0.0385(10) 0.0347(10) 0.0308(9) 0.0028(8) 0.0017(8) -0.0101(8) C90 0.0327(9) 0.0278(9) 0.0314(9) -0.0002(7) 0.0031(7) -0.0049(7) C91 0.0259(8) 0.0234(8) 0.0297(9) -0.0019(7) 0.0012(7) -0.0060(7) C92 0.0254(8) 0.0216(8) 0.0294(9) -0.0025(7) 0.0030(7) -0.0039(6) C93 0.0291(8) 0.0214(8) 0.0301(9) -0.0012(7) 0.0083(7) -0.0011(7) O1 0.0302(6) 0.0353(7) 0.0278(6) 0.0037(5) 0.0012(5) -0.0018(5) O2 0.0382(7) 0.0243(6) 0.0351(7) -0.0080(5) 0.0118(5) -0.0057(5) O82 0.0297(6) 0.0215(6) 0.0280(6) -0.0004(5) 0.0066(5) 0.0015(5) S1 0.0260(2) 0.0230(2) 0.0239(2) -0.00149(16) 0.00444(16) -0.00307(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 C2 C3 1.389(2) . ? C2 C7 1.395(2) . ? C2 S1 1.7578(16) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.389(3) . ? C5 H5 0.9500 . ? C6 C7 1.394(2) . ? C6 H6 0.9500 . ? C7 C8 1.529(2) . ? C8 C81 1.507(2) . ? C8 C9 1.522(2) . ? C8 H8 1.0000 . ? C9 C10 1.392(2) . ? C9 C14 1.394(2) . ? C10 C11 1.388(2) . ? C10 H10 0.9500 . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 C13 1.384(2) . ? C12 H12 0.9500 . ? C13 C14 1.393(2) . ? C13 H13 0.9500 . ? C14 S1 1.7635(16) . ? C81 C93 1.350(2) . ? C81 O82 1.3871(19) . ? C83 O82 1.379(2) . ? C83 C92 1.380(2) . ? C83 C84 1.401(2) . ? C84 C85 1.367(2) . ? C84 H84 0.9500 . ? C85 C86 1.429(2) . ? C85 H85 0.9500 . ? C86 C87 1.418(2) . ? C86 C91 1.427(2) . ? C87 C88 1.367(3) . ? C87 H87 0.9500 . ? C88 C89 1.403(3) . ? C88 H88 0.9500 . ? C89 C90 1.375(3) . ? C89 H89 0.9500 . ? C90 C91 1.414(2) . ? C90 H90 0.9500 . ? C91 C92 1.428(2) . ? C92 C93 1.440(2) . ? C93 H93 0.9500 . ? O1 S1 1.4441(12) . ? O2 S1 1.4402(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C2 C7 122.38(15) . . ? C3 C2 S1 118.38(13) . . ? C7 C2 S1 119.22(12) . . ? C4 C3 C2 119.00(16) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 119.68(16) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.79(16) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C7 120.76(17) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C2 117.38(15) . . ? C6 C7 C8 120.19(15) . . ? C2 C7 C8 122.35(14) . . ? C81 C8 C9 110.76(13) . . ? C81 C8 C7 113.38(13) . . ? C9 C8 C7 112.70(13) . . ? C81 C8 H8 106.5 . . ? C9 C8 H8 106.5 . . ? C7 C8 H8 106.5 . . ? C10 C9 C14 117.62(15) . . ? C10 C9 C8 120.04(15) . . ? C14 C9 C8 122.28(15) . . ? C11 C10 C9 120.64(16) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.76(16) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 119.73(16) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 118.86(16) . . ? C12 C13 H13 120.6 . . ? C14 C13 H13 120.6 . . ? C13 C14 C9 122.38(15) . . ? C13 C14 S1 118.20(13) . . ? C9 C14 S1 119.40(12) . . ? C93 C81 O82 111.09(15) . . ? C93 C81 C8 134.12(15) . . ? O82 C81 C8 114.74(13) . . ? O82 C83 C92 110.49(14) . . ? O82 C83 C84 124.97(15) . . ? C92 C83 C84 124.51(16) . . ? C85 C84 C83 116.54(16) . . ? C85 C84 H84 121.7 . . ? C83 C84 H84 121.7 . . ? C84 C85 C86 122.27(16) . . ? C84 C85 H85 118.9 . . ? C86 C85 H85 118.9 . . ? C87 C86 C91 118.33(16) . . ? C87 C86 C85 121.53(16) . . ? C91 C86 C85 120.14(15) . . ? C88 C87 C86 121.01(17) . . ? C88 C87 H87 119.5 . . ? C86 C87 H87 119.5 . . ? C87 C88 C89 120.53(17) . . ? C87 C88 H88 119.7 . . ? C89 C88 H88 119.7 . . ? C90 C89 C88 120.39(17) . . ? C90 C89 H89 119.8 . . ? C88 C89 H89 119.8 . . ? C89 C90 C91 120.39(17) . . ? C89 C90 H90 119.8 . . ? C91 C90 H90 119.8 . . ? C90 C91 C86 119.34(16) . . ? C90 C91 C92 123.54(16) . . ? C86 C91 C92 117.11(15) . . ? C83 C92 C91 119.37(15) . . ? C83 C92 C93 105.80(15) . . ? C91 C92 C93 134.70(16) . . ? C81 C93 C92 106.79(15) . . ? C81 C93 H93 126.6 . . ? C92 C93 H93 126.6 . . ? C83 O82 C81 105.80(12) . . ? O2 S1 O1 117.08(8) . . ? O2 S1 C2 110.75(7) . . ? O1 S1 C2 108.00(7) . . ? O2 S1 C14 108.71(8) . . ? O1 S1 C14 109.84(7) . . ? C2 S1 C14 101.31(8) . . ? 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 C7 C2 C3 C4 0.4(2) . . . . ? S1 C2 C3 C4 -178.25(13) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C3 C4 C5 C6 0.1(3) . . . . ? C4 C5 C6 C7 0.4(3) . . . . ? C5 C6 C7 C2 -0.4(2) . . . . ? C5 C6 C7 C8 -177.28(16) . . . . ? C3 C2 C7 C6 0.1(2) . . . . ? S1 C2 C7 C6 178.71(12) . . . . ? C3 C2 C7 C8 176.84(15) . . . . ? S1 C2 C7 C8 -4.5(2) . . . . ? C6 C7 C8 C81 -91.71(18) . . . . ? C2 C7 C8 C81 91.61(18) . . . . ? C6 C7 C8 C9 141.46(16) . . . . ? C2 C7 C8 C9 -35.2(2) . . . . ? C81 C8 C9 C10 91.41(18) . . . . ? C7 C8 C9 C10 -140.38(16) . . . . ? C81 C8 C9 C14 -91.58(18) . . . . ? C7 C8 C9 C14 36.6(2) . . . . ? C14 C9 C10 C11 -0.5(2) . . . . ? C8 C9 C10 C11 176.60(15) . . . . ? C9 C10 C11 C12 0.3(3) . . . . ? C10 C11 C12 C13 -0.3(3) . . . . ? C11 C12 C13 C14 0.6(2) . . . . ? C12 C13 C14 C9 -0.9(2) . . . . ? C12 C13 C14 S1 -178.95(13) . . . . ? C10 C9 C14 C13 0.8(2) . . . . ? C8 C9 C14 C13 -176.23(15) . . . . ? C10 C9 C14 S1 178.91(12) . . . . ? C8 C9 C14 S1 1.8(2) . . . . ? C9 C8 C81 C93 13.2(3) . . . . ? C7 C8 C81 C93 -114.6(2) . . . . ? C9 C8 C81 O82 -163.87(13) . . . . ? C7 C8 C81 O82 68.28(18) . . . . ? O82 C83 C84 C85 175.23(15) . . . . ? C92 C83 C84 C85 -2.6(3) . . . . ? C83 C84 C85 C86 0.5(3) . . . . ? C84 C85 C86 C87 -177.77(16) . . . . ? C84 C85 C86 C91 1.8(3) . . . . ? C91 C86 C87 C88 0.4(2) . . . . ? C85 C86 C87 C88 179.99(16) . . . . ? C86 C87 C88 C89 0.1(3) . . . . ? C87 C88 C89 C90 0.2(3) . . . . ? C88 C89 C90 C91 -1.1(3) . . . . ? C89 C90 C91 C86 1.6(2) . . . . ? C89 C90 C91 C92 -177.00(16) . . . . ? C87 C86 C91 C90 -1.3(2) . . . . ? C85 C86 C91 C90 179.17(15) . . . . ? C87 C86 C91 C92 177.42(15) . . . . ? C85 C86 C91 C92 -2.2(2) . . . . ? O82 C83 C92 C91 -175.90(14) . . . . ? C84 C83 C92 C91 2.2(3) . . . . ? O82 C83 C92 C93 0.63(18) . . . . ? C84 C83 C92 C93 178.69(16) . . . . ? C90 C91 C92 C83 178.90(15) . . . . ? C86 C91 C92 C83 0.3(2) . . . . ? C90 C91 C92 C93 3.6(3) . . . . ? C86 C91 C92 C93 -175.02(17) . . . . ? O82 C81 C93 C92 0.89(19) . . . . ? C8 C81 C93 C92 -176.26(17) . . . . ? C83 C92 C93 C81 -0.91(18) . . . . ? C91 C92 C93 C81 174.83(18) . . . . ? C92 C83 O82 C81 -0.11(17) . . . . ? C84 C83 O82 C81 -178.16(16) . . . . ? C93 C81 O82 C83 -0.50(18) . . . . ? C8 C81 O82 C83 177.24(13) . . . . ? C3 C2 S1 O2 -29.02(15) . . . . ? C7 C2 S1 O2 152.29(13) . . . . ? C3 C2 S1 O1 100.39(14) . . . . ? C7 C2 S1 O1 -78.30(14) . . . . ? C3 C2 S1 C14 -144.21(13) . . . . ? C7 C2 S1 C14 37.10(14) . . . . ? C13 C14 S1 O2 25.58(15) . . . . ? C9 C14 S1 O2 -152.56(13) . . . . ? C13 C14 S1 O1 -103.70(14) . . . . ? C9 C14 S1 O1 78.16(14) . . . . ? C13 C14 S1 C2 142.28(13) . . . . ? C9 C14 S1 C2 -35.86(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.298 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.067 # Attachment 'ccdc663292.CIF' data_sk-1-64 _database_code_depnum_ccdc_archive 'CCDC 663292' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H16 O2 S' _chemical_formula_sum 'C25 H16 O2 S' _chemical_formula_weight 380.44 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' O O 0.0106 0.0060 '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 monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.3719(8) _cell_length_b 11.5100(5) _cell_length_c 16.4409(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.926(2) _cell_angle_gamma 90.00 _cell_volume 3611.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8165 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 28.16 _exptl_crystal_description fragment _exptl_crystal_colour 'pale brown' _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type none _exptl_special_details ; The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source ; Bruker Nonius FR591 rotating anode generator ; _diffrn_radiation_monochromator ; graphite model mounted in "parallel" mode ; _diffrn_measurement_device_type ; Mach3 kappa-type 4-circle goniostat. ; _diffrn_radiation_detector 'ApexII camera' _diffrn_measurement_method 'rotation images' _diffrn_detector_area_resol_mean ; 120 microns ; _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29976 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0300 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4465 _reflns_number_gt 3671 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; APEX 2 software, Bruker Nonius 2004 ; _computing_cell_refinement ; APEX 2 software, Bruker Nonius 2004 ; _computing_data_reduction ; SAINT - Bruker Integration program embedded in APEX 2 software, Bruker Nonius 2004 ; _computing_structure_solution ; SHELXS-97 (Sheldrick, 1990) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_structure_refinement ; SHELXL-97 (Sheldrick, 1997) XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.) ; _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material ; enCIFer: A program for viewing, editing and visualising CIFs. F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler, J. Applied Cryst., 37, 331-334, 2004 ; _refine_special_details ; The structure solved in the monoclinic spacegroup C2/c. All hydrogen atoms could be located in the Fourier difference map but, in the final stages of the refinement, they were placed in calculated positions and refined using a riding model. C-H distances: aromatic, 0.95\A. All Uiso(H) values were constrained to be 1.2 times Ueq of the parent atom. C.Kilner 9 October 2007 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^)+(0.0389P)^2^+3.4008P] 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 4465 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 S1 S 0.401114(18) 0.63846(3) 0.14996(2) 0.02078(10) Uani 1 1 d . . . O1 O 0.39697(6) 0.76173(9) 0.12188(7) 0.0332(3) Uani 1 1 d . . . C2 C 0.38939(7) 0.63744(12) 0.25552(8) 0.0205(3) Uani 1 1 d . . . C3 C 0.41629(8) 0.73144(13) 0.30391(9) 0.0267(3) Uani 1 1 d . . . H3 H 0.4379 0.7942 0.2804 0.032 Uiso 1 1 calc R . . C4 C 0.41113(9) 0.73225(15) 0.38698(10) 0.0333(4) Uani 1 1 d . . . H4 H 0.4301 0.7952 0.4210 0.040 Uiso 1 1 calc R . . C5 C 0.37853(9) 0.64183(16) 0.42012(10) 0.0360(4) Uani 1 1 d . . . H5 H 0.3741 0.6437 0.4767 0.043 Uiso 1 1 calc R . . C6 C 0.35218(8) 0.54808(14) 0.37137(9) 0.0297(3) Uani 1 1 d . . . H6 H 0.3300 0.4862 0.3951 0.036 Uiso 1 1 calc R . . C7 C 0.35791(7) 0.54362(12) 0.28826(8) 0.0205(3) Uani 1 1 d . . . C8 C 0.33418(7) 0.43876(11) 0.23385(8) 0.0197(3) Uani 1 1 d . . . C9 C 0.29334(7) 0.47862(11) 0.15067(8) 0.0190(3) Uani 1 1 d . . . C10 C 0.23252(7) 0.42396(13) 0.11221(9) 0.0258(3) Uani 1 1 d . . . H10 H 0.2144 0.3598 0.1382 0.031 Uiso 1 1 calc R . . C11 C 0.19785(8) 0.46257(14) 0.03570(10) 0.0301(3) Uani 1 1 d . . . H11 H 0.1566 0.4238 0.0096 0.036 Uiso 1 1 calc R . . C12 C 0.22276(8) 0.55646(13) -0.00261(9) 0.0268(3) Uani 1 1 d . . . H12 H 0.1980 0.5836 -0.0540 0.032 Uiso 1 1 calc R . . C13 C 0.28409(7) 0.61113(12) 0.03411(9) 0.0223(3) Uani 1 1 d . . . H13 H 0.3020 0.6752 0.0078 0.027 Uiso 1 1 calc R . . C14 C 0.31891(7) 0.57117(11) 0.10960(8) 0.0183(3) Uani 1 1 d . . . O15 O 0.40050(5) 0.39201(8) 0.21656(6) 0.0189(2) Uani 1 1 d . . . C16 C 0.40353(7) 0.27615(11) 0.19756(8) 0.0184(3) Uani 1 1 d . . . C17 C 0.45482(7) 0.24407(11) 0.15004(8) 0.0197(3) Uani 1 1 d . . . C18 C 0.49577(7) 0.32629(12) 0.11557(9) 0.0221(3) Uani 1 1 d . . . H18 H 0.4905 0.4068 0.1256 0.027 Uiso 1 1 calc R . . C19 C 0.54298(8) 0.29004(14) 0.06784(9) 0.0284(3) Uani 1 1 d . . . H19 H 0.5692 0.3458 0.0434 0.034 Uiso 1 1 calc R . . C20 C 0.55291(9) 0.17107(15) 0.05468(10) 0.0347(4) Uani 1 1 d . . . H20 H 0.5861 0.1469 0.0218 0.042 Uiso 1 1 calc R . . C21 C 0.51530(9) 0.09032(14) 0.08865(10) 0.0339(4) Uani 1 1 d . . . H21 H 0.5236 0.0102 0.0804 0.041 Uiso 1 1 calc R . . C22 C 0.46405(8) 0.12325(12) 0.13615(9) 0.0258(3) Uani 1 1 d . . . C23 C 0.42216(9) 0.04093(12) 0.16907(10) 0.0319(4) Uani 1 1 d . . . H23 H 0.4289 -0.0397 0.1607 0.038 Uiso 1 1 calc R . . C24 C 0.37233(9) 0.07643(13) 0.21263(10) 0.0315(4) Uani 1 1 d . . . H24 H 0.3441 0.0200 0.2335 0.038 Uiso 1 1 calc R . . C25 C 0.36162(7) 0.19587(12) 0.22749(9) 0.0244(3) Uani 1 1 d . . . C26 C 0.30882(8) 0.23829(13) 0.27307(10) 0.0284(3) Uani 1 1 d . . . H26 H 0.2838 0.1847 0.3010 0.034 Uiso 1 1 calc R . . C27 C 0.29510(7) 0.35077(13) 0.27616(9) 0.0260(3) Uani 1 1 d . . . H27 H 0.2599 0.3764 0.3057 0.031 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 S1 0.02370(18) 0.01895(16) 0.02062(18) 0.00058(13) 0.00645(13) -0.00345(13) O1 0.0482(7) 0.0211(5) 0.0296(6) 0.0053(4) 0.0044(5) -0.0092(5) C2 0.0198(6) 0.0216(6) 0.0202(7) -0.0013(5) 0.0034(5) 0.0051(5) C3 0.0251(7) 0.0245(7) 0.0291(8) -0.0055(6) 0.0003(6) 0.0032(6) C4 0.0340(8) 0.0358(8) 0.0273(8) -0.0125(7) -0.0026(6) 0.0080(7) C5 0.0399(9) 0.0494(10) 0.0180(7) -0.0046(7) 0.0031(6) 0.0123(8) C6 0.0312(8) 0.0383(9) 0.0206(7) 0.0044(6) 0.0069(6) 0.0055(6) C7 0.0200(6) 0.0233(7) 0.0185(7) 0.0008(5) 0.0040(5) 0.0055(5) C8 0.0178(6) 0.0205(6) 0.0218(7) 0.0038(5) 0.0067(5) 0.0016(5) C9 0.0184(6) 0.0191(6) 0.0207(7) 0.0003(5) 0.0063(5) 0.0029(5) C10 0.0212(7) 0.0279(7) 0.0287(8) 0.0028(6) 0.0054(6) -0.0026(6) C11 0.0218(7) 0.0380(9) 0.0288(8) -0.0011(7) -0.0002(6) -0.0028(6) C12 0.0255(7) 0.0350(8) 0.0193(7) 0.0009(6) 0.0018(6) 0.0058(6) C13 0.0264(7) 0.0226(7) 0.0194(7) 0.0015(5) 0.0085(5) 0.0045(5) C14 0.0190(6) 0.0182(6) 0.0189(6) -0.0024(5) 0.0067(5) 0.0019(5) O15 0.0167(4) 0.0151(4) 0.0260(5) 0.0015(4) 0.0066(4) 0.0008(3) C16 0.0206(6) 0.0155(6) 0.0172(6) 0.0022(5) -0.0021(5) -0.0001(5) C17 0.0218(6) 0.0181(6) 0.0169(6) -0.0016(5) -0.0034(5) 0.0014(5) C18 0.0214(7) 0.0232(6) 0.0211(7) -0.0030(5) 0.0019(5) 0.0011(5) C19 0.0268(7) 0.0361(8) 0.0225(7) -0.0035(6) 0.0048(6) 0.0035(6) C20 0.0382(9) 0.0424(9) 0.0228(8) -0.0074(7) 0.0037(7) 0.0153(7) C21 0.0485(10) 0.0276(8) 0.0220(8) -0.0088(6) -0.0037(7) 0.0141(7) C22 0.0340(8) 0.0206(7) 0.0183(7) -0.0047(5) -0.0078(6) 0.0042(6) C23 0.0465(9) 0.0154(6) 0.0286(8) -0.0028(6) -0.0085(7) -0.0013(6) C24 0.0383(9) 0.0196(7) 0.0324(8) 0.0062(6) -0.0059(7) -0.0103(6) C25 0.0250(7) 0.0213(7) 0.0246(7) 0.0055(6) -0.0022(6) -0.0056(5) C26 0.0239(7) 0.0312(8) 0.0295(8) 0.0128(6) 0.0032(6) -0.0085(6) C27 0.0199(7) 0.0321(8) 0.0274(8) 0.0094(6) 0.0079(6) -0.0014(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4900(11) . ? S1 C2 1.7887(14) . ? S1 C14 1.7922(14) . ? C2 C3 1.3900(19) . ? C2 C7 1.393(2) . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.377(3) . ? C4 H4 0.9500 . ? C5 C6 1.388(2) . ? C5 H5 0.9500 . ? C6 C7 1.391(2) . ? C6 H6 0.9500 . ? C7 C8 1.5253(19) . ? C8 O15 1.4652(16) . ? C8 C27 1.5049(19) . ? C8 C9 1.5276(18) . ? C9 C10 1.3881(19) . ? C9 C14 1.3969(19) . ? C10 C11 1.393(2) . ? C10 H10 0.9500 . ? C11 C12 1.379(2) . ? C11 H11 0.9500 . ? C12 C13 1.387(2) . ? C12 H12 0.9500 . ? C13 C14 1.3851(19) . ? C13 H13 0.9500 . ? O15 C16 1.3731(15) . ? C16 C25 1.3758(19) . ? C16 C17 1.415(2) . ? C17 C18 1.415(2) . ? C17 C22 1.4255(18) . ? C18 C19 1.369(2) . ? C18 H18 0.9500 . ? C19 C20 1.405(2) . ? C19 H19 0.9500 . ? C20 C21 1.359(3) . ? C20 H20 0.9500 . ? C21 C22 1.416(2) . ? C21 H21 0.9500 . ? C22 C23 1.415(2) . ? C23 C24 1.360(3) . ? C23 H23 0.9500 . ? C24 C25 1.418(2) . ? C24 H24 0.9500 . ? C25 C26 1.453(2) . ? C26 C27 1.324(2) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 C2 107.33(6) . . ? O1 S1 C14 107.45(6) . . ? C2 S1 C14 95.92(6) . . ? C3 C2 C7 121.88(14) . . ? C3 C2 S1 116.90(11) . . ? C7 C2 S1 121.14(10) . . ? C4 C3 C2 119.03(15) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 120.03(15) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.47(15) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C7 120.81(15) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C2 117.74(13) . . ? C6 C7 C8 122.57(13) . . ? C2 C7 C8 119.63(12) . . ? O15 C8 C27 111.74(11) . . ? O15 C8 C7 102.64(10) . . ? C27 C8 C7 112.72(12) . . ? O15 C8 C9 105.83(10) . . ? C27 C8 C9 113.06(11) . . ? C7 C8 C9 110.16(11) . . ? C10 C9 C14 117.99(12) . . ? C10 C9 C8 122.66(12) . . ? C14 C9 C8 119.31(12) . . ? C9 C10 C11 120.41(14) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.68(14) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.84(13) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 119.18(13) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C9 121.86(13) . . ? C13 C14 S1 116.92(10) . . ? C9 C14 S1 121.14(10) . . ? C16 O15 C8 118.30(10) . . ? O15 C16 C25 121.33(13) . . ? O15 C16 C17 116.15(11) . . ? C25 C16 C17 122.42(13) . . ? C16 C17 C18 122.84(12) . . ? C16 C17 C22 117.56(13) . . ? C18 C17 C22 119.60(13) . . ? C19 C18 C17 120.13(14) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 120.54(15) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 120.40(15) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 121.32(14) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C23 C22 C21 122.32(14) . . ? C23 C22 C17 119.74(14) . . ? C21 C22 C17 117.95(14) . . ? C24 C23 C22 120.42(13) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 121.35(14) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C16 C25 C24 118.47(15) . . ? C16 C25 C26 118.04(13) . . ? C24 C25 C26 123.49(14) . . ? C27 C26 C25 120.81(13) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C8 121.32(14) . . ? C26 C27 H27 119.3 . . ? C8 C27 H27 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C2 C3 -34.24(12) . . . . ? C14 S1 C2 C3 -144.62(11) . . . . ? O1 S1 C2 C7 148.95(11) . . . . ? C14 S1 C2 C7 38.58(12) . . . . ? C7 C2 C3 C4 -0.5(2) . . . . ? S1 C2 C3 C4 -177.30(11) . . . . ? C2 C3 C4 C5 -1.2(2) . . . . ? C3 C4 C5 C6 1.6(2) . . . . ? C4 C5 C6 C7 -0.2(2) . . . . ? C5 C6 C7 C2 -1.5(2) . . . . ? C5 C6 C7 C8 175.76(14) . . . . ? C3 C2 C7 C6 1.9(2) . . . . ? S1 C2 C7 C6 178.50(10) . . . . ? C3 C2 C7 C8 -175.47(12) . . . . ? S1 C2 C7 C8 1.17(17) . . . . ? C6 C7 C8 O15 -111.96(14) . . . . ? C2 C7 C8 O15 65.23(14) . . . . ? C6 C7 C8 C27 8.39(18) . . . . ? C2 C7 C8 C27 -174.41(12) . . . . ? C6 C7 C8 C9 135.69(13) . . . . ? C2 C7 C8 C9 -47.11(16) . . . . ? O15 C8 C9 C10 111.86(14) . . . . ? C27 C8 C9 C10 -10.76(19) . . . . ? C7 C8 C9 C10 -137.87(13) . . . . ? O15 C8 C9 C14 -65.85(15) . . . . ? C27 C8 C9 C14 171.53(12) . . . . ? C7 C8 C9 C14 44.41(16) . . . . ? C14 C9 C10 C11 -1.2(2) . . . . ? C8 C9 C10 C11 -178.95(13) . . . . ? C9 C10 C11 C12 -0.8(2) . . . . ? C10 C11 C12 C13 1.9(2) . . . . ? C11 C12 C13 C14 -0.9(2) . . . . ? C12 C13 C14 C9 -1.2(2) . . . . ? C12 C13 C14 S1 175.47(10) . . . . ? C10 C9 C14 C13 2.3(2) . . . . ? C8 C9 C14 C13 -179.92(12) . . . . ? C10 C9 C14 S1 -174.31(10) . . . . ? C8 C9 C14 S1 3.51(17) . . . . ? O1 S1 C14 C13 31.97(12) . . . . ? C2 S1 C14 C13 142.25(11) . . . . ? O1 S1 C14 C9 -151.30(11) . . . . ? C2 S1 C14 C9 -41.03(12) . . . . ? C27 C8 O15 C16 33.83(16) . . . . ? C7 C8 O15 C16 154.86(10) . . . . ? C9 C8 O15 C16 -89.63(13) . . . . ? C8 O15 C16 C25 -28.59(17) . . . . ? C8 O15 C16 C17 155.09(11) . . . . ? O15 C16 C17 C18 -6.94(18) . . . . ? C25 C16 C17 C18 176.79(13) . . . . ? O15 C16 C17 C22 173.95(11) . . . . ? C25 C16 C17 C22 -2.32(19) . . . . ? C16 C17 C18 C19 -177.82(13) . . . . ? C22 C17 C18 C19 1.3(2) . . . . ? C17 C18 C19 C20 -2.0(2) . . . . ? C18 C19 C20 C21 0.6(2) . . . . ? C19 C20 C21 C22 1.7(2) . . . . ? C20 C21 C22 C23 177.18(14) . . . . ? C20 C21 C22 C17 -2.3(2) . . . . ? C16 C17 C22 C23 0.47(19) . . . . ? C18 C17 C22 C23 -178.67(12) . . . . ? C16 C17 C22 C21 -179.99(12) . . . . ? C18 C17 C22 C21 0.87(19) . . . . ? C21 C22 C23 C24 -178.36(14) . . . . ? C17 C22 C23 C24 1.2(2) . . . . ? C22 C23 C24 C25 -1.0(2) . . . . ? O15 C16 C25 C24 -173.61(12) . . . . ? C17 C16 C25 C24 2.5(2) . . . . ? O15 C16 C25 C26 6.13(19) . . . . ? C17 C16 C25 C26 -177.78(12) . . . . ? C23 C24 C25 C16 -0.7(2) . . . . ? C23 C24 C25 C26 179.52(14) . . . . ? C16 C25 C26 C27 8.9(2) . . . . ? C24 C25 C26 C27 -171.36(14) . . . . ? C25 C26 C27 C8 -0.9(2) . . . . ? O15 C8 C27 C26 -19.60(19) . . . . ? C7 C8 C27 C26 -134.58(14) . . . . ? C9 C8 C27 C26 99.67(16) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.309 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.049 # Attachment 'ccdc670085.cif' data_2006src0408 _database_code_depnum_ccdc_archive 'CCDC 670085' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Dr. B. M.Heron ; _chemical_name_common 'Dr. B. M.Heron' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 O2 S' _chemical_formula_weight 380.44 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' O O 0.0106 0.0060 '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 monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1939(5) _cell_length_b 14.0344(4) _cell_length_c 11.7187(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.498(2) _cell_angle_gamma 90.00 _cell_volume 1804.06(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4256 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 _exptl_crystal_description Shard _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.401 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9843 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21913 _diffrn_reflns_av_R_equivalents 0.0999 _diffrn_reflns_av_sigmaI/netI 0.0894 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4135 _reflns_number_gt 2928 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997a)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997b)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _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^)+(0.0291P)^2^+1.8406P] 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 4135 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1094 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.4114(2) 0.24667(17) 0.6498(2) 0.0198(6) Uani 1 1 d . . . C2 C 0.5268(2) 0.27530(17) 0.6096(2) 0.0209(6) Uani 1 1 d . . . H2 H 0.5754 0.2279 0.5831 0.025 Uiso 1 1 calc R . . C3 C 0.5607(2) 0.36610(17) 0.6108(2) 0.0206(6) Uani 1 1 d . . . H3 H 0.6362 0.3828 0.5908 0.025 Uiso 1 1 calc R . . C4 C 0.4823(2) 0.43997(17) 0.6429(2) 0.0189(5) Uani 1 1 d . . . C5 C 0.3648(2) 0.41431(17) 0.6477(2) 0.0195(6) Uani 1 1 d . . . C6 C 0.2779(2) 0.48000(17) 0.6691(2) 0.0228(6) Uani 1 1 d . . . H6 H 0.1974 0.4598 0.6711 0.027 Uiso 1 1 calc R . . C7 C 0.3101(3) 0.57378(18) 0.6871(2) 0.0247(6) Uani 1 1 d . . . H7 H 0.2511 0.6185 0.7013 0.030 Uiso 1 1 calc R . . C8 C 0.4296(2) 0.60513(17) 0.6851(2) 0.0215(6) Uani 1 1 d . . . C9 C 0.4636(3) 0.70210(18) 0.7044(2) 0.0230(6) Uani 1 1 d . . . H9 H 0.4051 0.7468 0.7198 0.028 Uiso 1 1 calc R . . C10 C 0.5781(3) 0.73203(18) 0.7014(2) 0.0253(6) Uani 1 1 d . . . H10 H 0.5994 0.7973 0.7136 0.030 Uiso 1 1 calc R . . C11 C 0.6651(2) 0.66554(18) 0.6798(2) 0.0237(6) Uani 1 1 d . . . H11 H 0.7455 0.6864 0.6782 0.028 Uiso 1 1 calc R . . C12 C 0.6361(2) 0.57130(17) 0.6612(2) 0.0207(6) Uani 1 1 d . . . H12 H 0.6964 0.5278 0.6469 0.025 Uiso 1 1 calc R . . C13 C 0.5173(2) 0.53797(17) 0.6632(2) 0.0191(6) Uani 1 1 d . . . C14 C 0.3514(2) 0.15947(17) 0.5840(2) 0.0194(6) Uani 1 1 d . . . C15 C 0.4061(2) 0.07025(18) 0.6082(2) 0.0204(6) Uani 1 1 d . . . C16 C 0.3557(3) -0.01178(18) 0.5534(2) 0.0253(6) Uani 1 1 d . . . H16 H 0.3946 -0.0716 0.5714 0.030 Uiso 1 1 calc R . . C17 C 0.2478(3) -0.00577(19) 0.4719(2) 0.0279(7) Uani 1 1 d . . . H17 H 0.2125 -0.0614 0.4328 0.033 Uiso 1 1 calc R . . C18 C 0.1918(3) 0.08193(19) 0.4477(2) 0.0285(7) Uani 1 1 d . . . H18 H 0.1176 0.0861 0.3919 0.034 Uiso 1 1 calc R . . C19 C 0.2423(3) 0.16390(19) 0.5037(2) 0.0244(6) Uani 1 1 d . . . H19 H 0.2020 0.2233 0.4870 0.029 Uiso 1 1 calc R . . C20 C 0.4408(2) 0.22228(17) 0.7804(2) 0.0182(5) Uani 1 1 d . . . C21 C 0.5012(2) 0.13744(17) 0.8158(2) 0.0190(6) Uani 1 1 d . . . C22 C 0.5271(2) 0.10876(18) 0.9312(2) 0.0228(6) Uani 1 1 d . . . H22 H 0.5699 0.0510 0.9530 0.027 Uiso 1 1 calc R . . C23 C 0.4896(3) 0.16573(18) 1.0145(2) 0.0250(6) Uani 1 1 d . . . H23 H 0.5055 0.1468 1.0939 0.030 Uiso 1 1 calc R . . C24 C 0.4288(3) 0.25006(19) 0.9811(2) 0.0257(6) Uani 1 1 d . . . H24 H 0.4036 0.2891 1.0382 0.031 Uiso 1 1 calc R . . C25 C 0.4041(2) 0.27860(18) 0.8648(2) 0.0224(6) Uani 1 1 d . . . H25 H 0.3620 0.3367 0.8431 0.027 Uiso 1 1 calc R . . O1 O 0.32327(16) 0.32181(11) 0.62904(15) 0.0211(4) Uani 1 1 d . . . O11 O 0.55634(18) -0.03835(12) 0.75931(16) 0.0297(5) Uani 1 1 d . . . S1 S 0.54759(6) 0.05989(4) 0.71052(6) 0.02161(17) 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 0.0213(14) 0.0168(12) 0.0210(13) -0.0015(10) 0.0031(11) 0.0011(10) C2 0.0252(15) 0.0190(12) 0.0188(13) 0.0013(10) 0.0048(11) 0.0037(11) C3 0.0206(14) 0.0210(12) 0.0196(13) 0.0016(10) 0.0030(11) 0.0006(11) C4 0.0222(14) 0.0203(12) 0.0136(12) 0.0017(10) 0.0019(10) 0.0005(11) C5 0.0259(15) 0.0180(12) 0.0131(12) -0.0002(10) 0.0001(11) -0.0006(11) C6 0.0209(14) 0.0247(13) 0.0219(14) 0.0013(11) 0.0022(11) -0.0003(11) C7 0.0269(16) 0.0225(13) 0.0251(14) 0.0012(11) 0.0059(12) 0.0067(11) C8 0.0275(15) 0.0210(13) 0.0157(13) 0.0015(10) 0.0039(11) 0.0011(11) C9 0.0293(16) 0.0201(12) 0.0205(14) -0.0020(11) 0.0069(12) 0.0027(11) C10 0.0341(17) 0.0182(12) 0.0223(14) -0.0024(11) 0.0024(12) -0.0022(12) C11 0.0217(15) 0.0251(13) 0.0234(14) 0.0034(11) 0.0025(11) -0.0031(12) C12 0.0203(14) 0.0205(12) 0.0207(13) 0.0030(10) 0.0027(11) 0.0019(11) C13 0.0266(15) 0.0186(12) 0.0113(12) 0.0017(10) 0.0023(11) 0.0010(10) C14 0.0218(14) 0.0191(12) 0.0188(13) 0.0010(10) 0.0075(11) -0.0004(11) C15 0.0208(14) 0.0233(13) 0.0182(13) -0.0008(11) 0.0065(11) -0.0007(11) C16 0.0308(16) 0.0225(13) 0.0248(15) -0.0007(11) 0.0110(13) -0.0006(12) C17 0.0318(17) 0.0258(14) 0.0269(15) -0.0096(12) 0.0079(13) -0.0072(12) C18 0.0270(16) 0.0325(15) 0.0244(15) -0.0055(12) 0.0007(12) -0.0039(12) C19 0.0261(16) 0.0244(13) 0.0226(14) 0.0001(11) 0.0045(12) 0.0014(12) C20 0.0156(13) 0.0201(12) 0.0189(13) -0.0002(10) 0.0032(10) -0.0036(10) C21 0.0168(14) 0.0195(12) 0.0209(13) -0.0038(10) 0.0042(11) -0.0031(10) C22 0.0224(15) 0.0217(13) 0.0232(14) 0.0007(11) 0.0015(12) -0.0019(11) C23 0.0309(16) 0.0249(13) 0.0187(13) 0.0012(11) 0.0035(12) -0.0010(12) C24 0.0307(17) 0.0268(14) 0.0206(14) -0.0045(11) 0.0077(12) -0.0021(12) C25 0.0227(15) 0.0212(13) 0.0228(14) 0.0010(11) 0.0034(11) 0.0002(11) O1 0.0205(10) 0.0174(9) 0.0250(10) -0.0005(7) 0.0033(8) 0.0005(7) O11 0.0414(13) 0.0197(9) 0.0272(10) 0.0010(8) 0.0045(9) 0.0062(8) S1 0.0238(4) 0.0195(3) 0.0215(3) -0.0012(3) 0.0043(3) 0.0024(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 O1 1.432(3) . ? C1 C2 1.515(4) . ? C1 C14 1.529(3) . ? C1 C20 1.538(3) . ? C2 C3 1.329(3) . ? C2 H2 0.9500 . ? C3 C4 1.455(4) . ? C3 H3 0.9500 . ? C4 C5 1.376(4) . ? C4 C13 1.437(3) . ? C5 O1 1.382(3) . ? C5 C6 1.399(4) . ? C6 C7 1.370(4) . ? C6 H6 0.9500 . ? C7 C8 1.413(4) . ? C7 H7 0.9500 . ? C8 C9 1.419(3) . ? C8 C13 1.421(4) . ? C9 C10 1.356(4) . ? C9 H9 0.9500 . ? C10 C11 1.408(4) . ? C10 H10 0.9500 . ? C11 C12 1.369(3) . ? C11 H11 0.9500 . ? C12 C13 1.413(4) . ? C12 H12 0.9500 . ? C14 C19 1.386(4) . ? C14 C15 1.398(3) . ? C15 C16 1.383(4) . ? C15 S1 1.792(3) . ? C16 C17 1.385(4) . ? C16 H16 0.9500 . ? C17 C18 1.385(4) . ? C17 H17 0.9500 . ? C18 C19 1.388(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C25 1.390(4) . ? C20 C21 1.391(3) . ? C21 C22 1.385(4) . ? C21 S1 1.798(3) . ? C22 C23 1.390(4) . ? C22 H22 0.9500 . ? C23 C24 1.382(4) . ? C23 H23 0.9500 . ? C24 C25 1.395(4) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? O11 S1 1.4884(18) . ? 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 O1 C1 C2 110.7(2) . . ? O1 C1 C14 106.6(2) . . ? C2 C1 C14 111.8(2) . . ? O1 C1 C20 109.7(2) . . ? C2 C1 C20 110.0(2) . . ? C14 C1 C20 108.02(19) . . ? C3 C2 C1 120.7(2) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C2 C3 C4 120.0(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C13 118.4(2) . . ? C5 C4 C3 117.1(2) . . ? C13 C4 C3 124.5(2) . . ? C4 C5 O1 122.3(2) . . ? C4 C5 C6 122.6(2) . . ? O1 C5 C6 115.1(2) . . ? C7 C6 C5 119.3(3) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 121.2(2) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C9 121.4(2) . . ? C7 C8 C13 119.2(2) . . ? C9 C8 C13 119.5(2) . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.4(2) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C12 C11 C10 121.2(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 118.0(2) . . ? C12 C13 C4 122.7(2) . . ? C8 C13 C4 119.3(2) . . ? C19 C14 C15 117.9(2) . . ? C19 C14 C1 123.1(2) . . ? C15 C14 C1 119.0(2) . . ? C16 C15 C14 122.0(2) . . ? C16 C15 S1 117.9(2) . . ? C14 C15 S1 120.09(19) . . ? C15 C16 C17 119.3(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C18 119.5(2) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C19 121.0(3) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C14 C19 C18 120.3(2) . . ? C14 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C25 C20 C21 118.0(2) . . ? C25 C20 C1 123.1(2) . . ? C21 C20 C1 118.8(2) . . ? C22 C21 C20 122.3(2) . . ? C22 C21 S1 117.45(19) . . ? C20 C21 S1 120.24(19) . . ? C21 C22 C23 119.0(2) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C24 C23 C22 119.6(2) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 120.9(3) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C20 C25 C24 120.2(2) . . ? C20 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C5 O1 C1 117.80(19) . . ? O11 S1 C15 108.29(12) . . ? O11 S1 C21 107.64(11) . . ? C15 S1 C21 94.15(12) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.369 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.066 # Attachment 'ccdc670086.cif' data_2006src0544 _database_code_depnum_ccdc_archive 'CCDC 670086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H16 O2 S' _chemical_formula_weight 380.44 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' O O 0.0106 0.0060 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.3454(2) _cell_length_b 13.4896(2) _cell_length_c 11.5736(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.3650(10) _cell_angle_gamma 90.00 _cell_volume 1760.36(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4147 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9415 _exptl_absorpt_correction_T_max 0.9605 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22230 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4007 _reflns_number_gt 3750 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _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^)+(0.0397P)^2^+1.1620P] 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 4007 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0943 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 0.65268(11) 0.26316(9) 0.84179(11) 0.0148(3) Uani 1 1 d . . . C2 C 0.73376(11) 0.35149(10) 0.85435(11) 0.0168(3) Uani 1 1 d . . . H2 H 0.8172 0.3422 0.8613 0.020 Uiso 1 1 calc R . . C3 C 0.68926(11) 0.44292(10) 0.85588(11) 0.0166(3) Uani 1 1 d . . . H3 H 0.7411 0.4984 0.8603 0.020 Uiso 1 1 calc R . . C4 C 0.56124(11) 0.45838(10) 0.85078(11) 0.0148(3) Uani 1 1 d . . . C5 C 0.49235(11) 0.37637(9) 0.86797(11) 0.0142(2) Uani 1 1 d . . . C6 C 0.36890(11) 0.38296(10) 0.87151(11) 0.0167(3) Uani 1 1 d . . . H6 H 0.3240 0.3253 0.8839 0.020 Uiso 1 1 calc R . . C7 C 0.31429(12) 0.47313(10) 0.85691(12) 0.0181(3) Uani 1 1 d . . . H7 H 0.2309 0.4775 0.8587 0.022 Uiso 1 1 calc R . . C8 C 0.37986(11) 0.56023(10) 0.83910(11) 0.0161(3) Uani 1 1 d . . . C9 C 0.32440(12) 0.65467(10) 0.82652(12) 0.0198(3) Uani 1 1 d . . . H9 H 0.2410 0.6596 0.8276 0.024 Uiso 1 1 calc R . . C10 C 0.38910(13) 0.73874(10) 0.81285(12) 0.0206(3) Uani 1 1 d . . . H10 H 0.3508 0.8014 0.8053 0.025 Uiso 1 1 calc R . . C11 C 0.51257(13) 0.73201(10) 0.81006(12) 0.0207(3) Uani 1 1 d . . . H11 H 0.5574 0.7905 0.8011 0.025 Uiso 1 1 calc R . . C12 C 0.56891(12) 0.64178(10) 0.82013(12) 0.0189(3) Uani 1 1 d . . . H12 H 0.6521 0.6386 0.8166 0.023 Uiso 1 1 calc R . . C13 C 0.50519(11) 0.55333(10) 0.83570(11) 0.0153(2) Uani 1 1 d . . . C20 C 0.61990(11) 0.23266(9) 0.71463(11) 0.0145(2) Uani 1 1 d . . . C21 C 0.55130(11) 0.14752(9) 0.69095(11) 0.0148(2) Uani 1 1 d . . . C22 C 0.52095(11) 0.11349(10) 0.57840(12) 0.0177(3) Uani 1 1 d . . . H22 H 0.4732 0.0559 0.5647 0.021 Uiso 1 1 calc R . . C23 C 0.56112(12) 0.16458(10) 0.48589(12) 0.0193(3) Uani 1 1 d . . . H23 H 0.5437 0.1407 0.4087 0.023 Uiso 1 1 calc R . . C24 C 0.62674(12) 0.25061(11) 0.50738(12) 0.0204(3) Uani 1 1 d . . . H24 H 0.6521 0.2867 0.4441 0.024 Uiso 1 1 calc R . . C25 C 0.65603(12) 0.28488(10) 0.62069(12) 0.0181(3) Uani 1 1 d . . . H25 H 0.7008 0.3441 0.6339 0.022 Uiso 1 1 calc R . . C14 C 0.69893(11) 0.17222(10) 0.91101(11) 0.0159(3) Uani 1 1 d . . . C15 C 0.63225(12) 0.08511(10) 0.90130(11) 0.0161(3) Uani 1 1 d . . . C16 C 0.66449(13) 0.00130(10) 0.96700(12) 0.0206(3) Uani 1 1 d . . . H16 H 0.6169 -0.0568 0.9596 0.025 Uiso 1 1 calc R . . C17 C 0.76797(14) 0.00407(11) 1.04387(12) 0.0247(3) Uani 1 1 d . . . H17 H 0.7909 -0.0522 1.0904 0.030 Uiso 1 1 calc R . . C18 C 0.83752(13) 0.08861(11) 1.05268(13) 0.0244(3) Uani 1 1 d . . . H18 H 0.9091 0.0895 1.1037 0.029 Uiso 1 1 calc R . . C19 C 0.80319(12) 0.17253(11) 0.98705(12) 0.0208(3) Uani 1 1 d . . . H19 H 0.8512 0.2304 0.9942 0.025 Uiso 1 1 calc R . . O1 O 0.54141(8) 0.28424(7) 0.88993(8) 0.0155(2) Uani 1 1 d . . . O11 O 0.48233(9) -0.02654(7) 0.76461(9) 0.0235(2) Uani 1 1 d . . . S1 S 0.49657(3) 0.07808(2) 0.80589(3) 0.01641(10) 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 0.0135(6) 0.0158(6) 0.0155(6) -0.0005(5) 0.0028(5) 0.0007(5) C2 0.0135(6) 0.0194(6) 0.0175(6) -0.0013(5) 0.0017(5) -0.0016(5) C3 0.0146(6) 0.0185(6) 0.0168(6) -0.0020(5) 0.0021(5) -0.0033(5) C4 0.0148(6) 0.0172(6) 0.0121(6) -0.0012(5) 0.0006(4) -0.0014(5) C5 0.0164(6) 0.0155(6) 0.0107(5) -0.0017(5) 0.0010(4) 0.0004(5) C6 0.0158(6) 0.0190(6) 0.0154(6) -0.0014(5) 0.0024(5) -0.0035(5) C7 0.0139(6) 0.0223(7) 0.0179(6) -0.0019(5) 0.0016(5) -0.0004(5) C8 0.0170(6) 0.0189(6) 0.0121(6) -0.0013(5) 0.0002(5) 0.0007(5) C9 0.0197(6) 0.0224(7) 0.0169(6) -0.0010(5) 0.0006(5) 0.0036(5) C10 0.0278(7) 0.0183(6) 0.0156(6) 0.0010(5) 0.0010(5) 0.0049(5) C11 0.0276(7) 0.0170(6) 0.0176(6) 0.0013(5) 0.0033(5) -0.0024(5) C12 0.0195(6) 0.0192(6) 0.0183(6) -0.0001(5) 0.0034(5) -0.0019(5) C13 0.0170(6) 0.0170(6) 0.0118(6) -0.0012(5) 0.0017(4) -0.0008(5) C20 0.0135(6) 0.0154(6) 0.0146(6) -0.0005(5) 0.0015(4) 0.0023(5) C21 0.0132(6) 0.0164(6) 0.0149(6) 0.0013(5) 0.0017(4) 0.0022(5) C22 0.0172(6) 0.0170(6) 0.0185(6) -0.0014(5) 0.0001(5) 0.0017(5) C23 0.0211(6) 0.0220(7) 0.0146(6) -0.0010(5) 0.0011(5) 0.0051(5) C24 0.0226(7) 0.0222(7) 0.0171(6) 0.0037(5) 0.0057(5) 0.0033(5) C25 0.0186(6) 0.0173(6) 0.0188(6) 0.0014(5) 0.0044(5) 0.0004(5) C14 0.0174(6) 0.0173(6) 0.0132(6) -0.0015(5) 0.0023(5) 0.0024(5) C15 0.0179(6) 0.0180(6) 0.0125(6) -0.0009(5) 0.0019(5) 0.0022(5) C16 0.0290(7) 0.0182(6) 0.0148(6) 0.0003(5) 0.0033(5) 0.0032(5) C17 0.0344(8) 0.0225(7) 0.0165(6) 0.0020(5) -0.0002(6) 0.0093(6) C18 0.0244(7) 0.0296(8) 0.0178(7) -0.0019(6) -0.0041(5) 0.0067(6) C19 0.0201(6) 0.0236(7) 0.0183(6) -0.0033(5) 0.0000(5) 0.0012(5) O1 0.0147(4) 0.0147(4) 0.0176(4) -0.0001(3) 0.0043(3) 0.0005(3) O11 0.0300(5) 0.0167(5) 0.0230(5) 0.0007(4) -0.0014(4) -0.0066(4) S1 0.01672(17) 0.01689(17) 0.01556(17) 0.00162(11) 0.00150(12) -0.00257(11) _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 O1 1.4632(14) . ? C1 C2 1.5024(17) . ? C1 C14 1.5260(18) . ? C1 C20 1.5337(17) . ? C2 C3 1.3335(19) . ? C2 H2 0.9500 . ? C3 C4 1.4620(17) . ? C3 H3 0.9500 . ? C4 C5 1.3817(18) . ? C4 C13 1.4320(18) . ? C5 O1 1.3739(15) . ? C5 C6 1.4085(17) . ? C6 C7 1.3670(19) . ? C6 H6 0.9500 . ? C7 C8 1.4179(19) . ? C7 H7 0.9500 . ? C8 C9 1.4212(18) . ? C8 C13 1.4298(18) . ? C9 C10 1.370(2) . ? C9 H9 0.9500 . ? C10 C11 1.408(2) . ? C10 H10 0.9500 . ? C11 C12 1.3737(19) . ? C11 H11 0.9500 . ? C12 C13 1.4169(18) . ? C12 H12 0.9500 . ? C20 C25 1.3947(18) . ? C20 C21 1.3974(18) . ? C21 C22 1.3880(18) . ? C21 S1 1.7932(13) . ? C22 C23 1.3919(19) . ? C22 H22 0.9500 . ? C23 C24 1.386(2) . ? C23 H23 0.9500 . ? C24 C25 1.3954(19) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C14 C19 1.3938(18) . ? C14 C15 1.3954(18) . ? C15 C16 1.3887(18) . ? C15 S1 1.7947(13) . ? C16 C17 1.393(2) . ? C16 H16 0.9500 . ? C17 C18 1.384(2) . ? C17 H17 0.9500 . ? C18 C19 1.395(2) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? O11 S1 1.4930(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 110.73(10) . . ? O1 C1 C14 102.55(10) . . ? C2 C1 C14 114.56(11) . . ? O1 C1 C20 106.85(10) . . ? C2 C1 C20 112.73(10) . . ? C14 C1 C20 108.71(10) . . ? C3 C2 C1 120.41(11) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.48(12) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C13 118.88(12) . . ? C5 C4 C3 117.08(12) . . ? C13 C4 C3 123.94(12) . . ? O1 C5 C4 121.80(11) . . ? O1 C5 C6 115.82(11) . . ? C4 C5 C6 122.27(12) . . ? C7 C6 C5 119.41(12) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 121.16(12) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C7 C8 C9 121.62(12) . . ? C7 C8 C13 119.30(12) . . ? C9 C8 C13 119.07(12) . . ? C10 C9 C8 121.15(12) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 119.78(13) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 C10 120.67(13) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.18(12) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C8 118.14(12) . . ? C12 C13 C4 122.87(12) . . ? C8 C13 C4 118.98(12) . . ? C25 C20 C21 117.88(12) . . ? C25 C20 C1 123.48(12) . . ? C21 C20 C1 118.64(11) . . ? C22 C21 C20 122.06(12) . . ? C22 C21 S1 116.94(10) . . ? C20 C21 S1 120.99(10) . . ? C21 C22 C23 119.33(12) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C24 C23 C22 119.44(12) . . ? C24 C23 H23 120.3 . . ? C22 C23 H23 120.3 . . ? C23 C24 C25 120.87(12) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C20 C25 C24 120.36(12) . . ? C20 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C19 C14 C15 117.90(12) . . ? C19 C14 C1 123.19(12) . . ? C15 C14 C1 118.88(11) . . ? C16 C15 C14 122.28(12) . . ? C16 C15 S1 116.73(10) . . ? C14 C15 S1 120.96(10) . . ? C15 C16 C17 118.70(13) . . ? C15 C16 H16 120.7 . . ? C17 C16 H16 120.7 . . ? C18 C17 C16 120.16(13) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 120.41(13) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C19 C18 120.51(13) . . ? C14 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C5 O1 C1 117.02(10) . . ? O11 S1 C21 106.89(6) . . ? O11 S1 C15 107.57(6) . . ? C21 S1 C15 94.87(6) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.360 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.074